Herbicidal compositions and methods for controlling weeds

Abstract

The present application relates to a protoporphyrinogen IX oxidase (PPO) herbicidal composition comprising a cyclic nuclear 2H-benzo [b] [1, 4] oxazine-3 (4H)-one compound of formula (I) substituted at the 6-position with a suitably substituted phenyl moiety and at least one compound selected from the group consisting of a second herbicide compound and a herbicide safener.

Description

[0001] Cross-references to related applications

[0002] This application claims priority to U.S. Provisional Patent Application No. 63 / 452,033, filed March 14, 2023, which is incorporated herein by reference in its entirety. Technical Field

[0003] This invention relates to a protoporphyrinogen IX oxidase (PPO) herbicidal composition comprising benzoxazinone having formula (I) and a second herbicide. Background Technology

[0004] Since the 1960s, herbicides that inhibit protoporphyrinogen oxidase (hereinafter referred to as Protox or PPO; EC: 1.3.3.4) (a key enzyme in the biosynthesis of protoporphyrin IX) have been used for selective weed control. PPO catalyzes the final common step in the biosynthesis of chlorophyll and heme, namely the oxidation of protoporphyrinogen IX to protoporphyrin IX [Matringe M. et al., Protop orphyrinogen oxidase as a molecular target for diphenyl ether herbicides, Biochemistry Journal (1989) 260: 231-235]. The application of PPO-inhibiting herbicides leads to the accumulation of protoporphyrinogen IX in chloroplasts and mitochondria, which is thought to leak into the cytosol, where it is oxidized by peroxidase. When exposed to light, protoporphyrin IX leads to the formation of singlet oxygen and other reactive oxygen species in the cytosol, which can cause lipid peroxidation and membrane damage, resulting in rapid cell death [Lee HJ et al., Cellular localization of protoporphyrinogen-oxidizing activities of etiolated barley leaves, Plant Physiology (1993) 102:881].

[0005] To date, thousands of PPO inhibitors have been reported in the literature, of which about 30 are currently used as herbicides to eliminate weeds in the field [Hao, GF et al., Protoporphyrinogen oxidase inhibitor: an ideal target for herbicide discovery, Chimia (2011) 65, 961-969]. Herbicides that inhibit PPO include molecules of many different structural classes, including diphenyl ethers (e.g., lactoferrin, acifluorfen, methyl acifluorfen, or oxyfluorfen); oxadiazoles (e.g., oxadiazon); cyclic imides [e.g., S-23142, N-(4-chloro-2-fluoro-5-propynyloxyphenyl)-3,4,5,6-tetrahydrophthalimide, chlorophthalimide, N-(4-chlorophenyl)-3,4,5,6-tetrahydrophthalimide]; phenylpyrazoles (e.g., TNPP-ethyl, ethyl 2-[1-(2,3,4-trichlorophenyl)-4-nitropyrazolyl-5-oxy]propionate, M&B39279); and pyridine derivatives (e.g., LS). 82-556); and phenopylate and its O-phenylpyrrolidine-piperidine carbamate analogs ( W. (ed.), Modern Crop Protection Compounds, 2nd ed., Vol. 1: Herbicides, (2012) Wiley-VCH, Weinheim, Germany. Many of these compounds competitively inhibit normal enzyme-catalyzed reactions, apparently acting as substrate analogs.

[0006] However, the weed-control properties of these known compounds against harmful plants are not always entirely satisfactory. Herbicide-resistant weeds pose a serious problem for effective weed control, as they become increasingly prevalent and therefore weed control by herbicide application is no longer effective, causing significant problems for farmers. The development of resistance to PPO herbicides has been slow (approximately forty years since their initial commercialization) and has so far been confirmed in 13 weed species [HeapI, The International Survey of Herbicide Resistant Weeds. Available online: http: / / www.weedscience.org / (October 2019)]. The first weed to evolve resistance to PPO herbicides was waterhemp (Amaranthus tuberculatus) in 2001 [Shoup DE et al., Common waterhemp (Amaranthus rudis) resistance to protoporphyrinogen oxidase-inhibiting herbicides Weed Sci. (2003) 51:145-150]. Resistance to PPO herbicides in this weed species is attributed to target site mutations in the PPX2 gene. For example, a unique target site amino acid deletion (Gly... 210 ) and Arg 98 Leu substitution confers PPO resistance in water hemp [Patzoldt WL et al., Acodon deletion confers resistance to herbicides inhibiting protoporphyrinogen oxidase. Proc. Natl. Acad. Sci. USA (2006) 103: 12329–12334] and common ragweed [Rousonelos et al., Characterization of a common ragweed (Ambrosia artemisiifolia) population resistant to ALS-and PPO-inhibiting herbicides, Weed Sci. (2012) 60: 335-344].

[0007] Therefore, there is a need for new methods to effectively control weeds, including herbicide-resistant weeds, particularly PPO-resistant weeds, which are also resistant to the beneficial plants (crops) discussed. The object of this invention is to provide herbicidal compositions and methods for controlling weeds that exhibit excellent weed control effects. Summary of the Invention

[0008] This invention relates to a herbicidal composition comprising a compound of formula (I), such as 7-fluoro-6-(perfluorophenyl)-4-(prop-2-yn-1-yl)-2H-benzo[b][1,4]oxazine-3(4H)-one, and at least one compound selected from the group consisting of herbicide compounds B and safener group C, wherein the weight ratio of the compound of formula (I) to at least one compound selected from the group consisting of herbicide compounds B and safener group C is from 1:0.1 to 1:50. The compound of formula (I) is as follows:

[0009]

[0010] Or its salt, wherein:

[0011] R 1 R 2 R 3 R 4 R 5 R 6 R 7 and R 8 As described elsewhere in this article.

[0012] In one embodiment, the compound of formula (I) is 7-fluoro-6-(perfluorophenyl)-4-(prop-2-yn-1-yl)-2H-benzo[b][1,4]oxazine-3(4H)-one (compound 1), with the following structure:

[0013]

[0014] definition

[0015] As used herein, the terms “comprises / comprising,” “includes / including,” “has / having,” “contains / containing,” “characterized in,” or any other variation thereof are intended to cover non-exclusive inclusion, subject to any expressly indicated limitations. For example, a composition, mixture, process, or method that includes or contains a list of elements is not necessarily limited to those elements, but may include other elements not expressly listed or inherent to such composition, mixture, process, or method.

[0016] The transitional phrase "composed of..." excludes any unspecified element, step, or ingredient. If in a claim, this would exclude materials other than impurities typically associated with them. When the phrase "composed of..." appears in a clause of the body of a claim rather than immediately following the preamble, it limits only the elements set forth in that clause; as a whole, other elements are not excluded from the claim.

[0017] Furthermore, unless explicitly stated to the contrary, "or" refers to an inclusive "or" rather than an exclusive "or". For example, condition A or condition B is satisfied by any of the following: A is true (or exists) and B is false (or does not exist), A is false (or does not exist) and B is true (or exists), and both A and B are true (or exist).

[0018] Furthermore, the indefinite article "a / an" preceding an element or component of the invention is intended not to limit the number of instances (i.e., the number of times) of that element or component. Therefore, "a / an" should be understood to include one or at least one, and the singular form of an element or component also includes the plural, unless the number clearly implies singularity.

[0019] As described in this article, the term “seedling” used alone or in combination refers to a young plant that develops from the embryo of a seed.

[0020] As described herein, the term "broadleaf" used alone or in terms such as "broadleaf weeds" refers to dicotyledonous or dicotyledonous plants, a term used to describe a group of angiosperms characterized by an embryo with two cotyledons.

[0021] When referring to compounds of the present invention, the term "acceptable salt" or "salt" includes cations or anions. Preferred cations are alkali metal ions, preferably lithium, sodium, and potassium ions; alkaline earth metal ions, preferably calcium and magnesium ions; and transition metal ions, preferably manganese, copper, zinc, and iron ions; additional ammonium and substituted ammonium, wherein one to four hydrogen atoms are replaced by C1-C4-alkyl, hydroxy-C1-C4-alkyl, C1-C4-alkoxy-C1-C4-alkyl, hydroxy-C1-C4-alkoxy-C1-C4-alkyl, phenyl, or benzyl, preferably ammonium, methylammonium, isopropylammonium, dimethylammonium, diethylammonium, diisopropylammonium, trimethylammonium, triethylammonium, tri(isopropyl), heptylammonium, dodecylammonium, tetradecylammonium, and tetramethylammonium. Tetraethylammonium, tetrabutylammonium, 2-hydroxyethylammonium (ethanolamine salt), 2-(2-hydroxyethyl-1-oxy)ethyl-1-ylammonium (diethylene glycolamine salt), di(2-hydroxyethyl-1-yl)ammonium (diethanolamine salt), tri(2-hydroxyethyl)ammonium (triethanolamine salt), tri(2-hydroxypropyl)ammonium, benzyltrimethylammonium, benzyltriethylammonium, N,N,N-trimethylethanolammonium (choline salt), in addition, phosphate ions, sulfonium ions, preferably tri(C1-C4-alkyl)sulfonium, such as trimethylsulfonium, and sulfonium oxide ions, preferably tri(C1-C4-alkyl)sulfonium oxide, and finally, salts of polyamines, such as N,N-bis-(3-aminopropyl)methylamine and diethylenetriamine.

[0022] The useful anions of acid addition salts are mainly chloride, bromide, fluoride, iodide, hydrogen sulfate, methyl sulfate, sulfate, dihydrogen phosphate, hydrogen phosphate, nitrate, bicarbonate, carbonate, hexafluorosilicate, hexafluorophosphate, benzoate, and anions of C1-C4-alkanes (preferably formate, acetate, propionate, and butyrate).

[0023] As used in this article, the terms “undesirable vegetation” and “harmful plants” are synonyms.

[0024] The abbreviations for weed species are as follows: AMATU for Amaranthus rudis, CHEAL for Lambsquarters (Chenopodium album), ABUTH for Velvetleaf (Abutilon theophrasti), SETFA for Giant Foxtail (Setariafaberi), AMAPA for Palmer amaranth (Amaranthus palmeri), AMARE for Redroot Pigweed (Amaranthus retroflexus), KCHSC for Kochia (Bassia scoparia), ALOMY for Blackgrass (Alopecurus myosuroides), and ECHCG for Barnyard Grass (Echinochloa). crus-galli), and DIGSA is large crabgrass (Digitaria sanguinalis). Detailed Implementation

[0025] In one aspect, a herbicidal composition is provided comprising a compound of formula (I):

[0026]

[0027] Or its salt, wherein:

[0028] R 1 Is H or optionally R 1a C substituted with phenyl or benzyl 1-4 Alkyl group, wherein each of the alkyl, phenyl, or benzyl groups is optionally surrounded by at most three F atoms, one OH group, or one OC group. 1-4 Alkyl group substitution;

[0029] R 1a yes

[0030] Each R 1b H and C independently 1-4 Alkyl or cyclopropyl;

[0031] R 2 and R 3 Each of them independently is H, Cl, F, CH3, or R. 2 and R3 Together with the carbon in the middle, it is cyclopropyl;

[0032] R 4 It is H, Cl, or F;

[0033] R 5 It is H or F;

[0034] R 6 and R 7 Each is independently F, H, or C that is optionally replaced by OH. 1-2 Alkyl, alkenyl, OH, OC 1-2 Alkyl, O-cyclopropyl, OCH2CCH, NHCH2Ph, N(R) x )2 or SCH3;

[0035] R 8 It is H or F;

[0036] Each R x It is independently H, CH3, or C(O)CH3; and

[0037] Ring A contains at least four F-atom substituents.

[0038] It further comprises at least one compound from herbicide group B and optionally a safener from group C, wherein the weight ratio of the compound of formula (I) to at least one compound selected from the group consisting of herbicide compounds group B is from 1:0.1 to 1:50, and wherein the herbicide from group B is selected from groups B-1 to B-12: B-1, acetolactate synthase inhibitor; B-2, acetyl-CoA carboxylase inhibitor; B-3, protoporphyrinogen IX oxidase inhibitor; B-4, 4-hydrophenylpyruvate dioxygenase inhibitor; B-5, phytopenic acid desaturase inhibitor; B-6, photosystem II inhibitor; B-7, long-chain fatty acid synthesis inhibitor; B-8, microtubule formation inhibitor; B-9, auxin herbicide; B-10, enolpyruvylshikimate 3-phosphate synthase inhibitor; B-11, glutamine synthase inhibitor; and B-12, other herbicides comprising their agriculturally acceptable salts or derivatives.

[0039] In one embodiment, the compound of formula (I) is 7-fluoro-6-(perfluorophenyl)-4-(prop-2-yn-1-yl)-2H-benzo[b][1,4]oxazine-3(4H)-one (compound 1), with the following structure:

[0040]

[0041] In another embodiment, group B-1 comprises herbicides selected from group B: pyrithiobac, pyrithiobac-sodium salt, pyriminobac, pyriminobac-methyl, bispyribac, bispyribac-sodiumsalt, pyribenzoxim, pyrimisulfan, pyriftalid, triafamone, amidosulfuron, azimsulfuron, bensulfuron, bensulfuron-methyl, chlorimuron, chlorimuron-ethyl, and cyclosulfuron. ethoxysulfuron, flazasulfuron, flucetosulfuron, flupyrsulfuron, flupyrsulfuron-methyl-sodium, foramsulfuron, halosulfuron, halosulfuron-methyl, imazosulfuron, mesosulfuron, mesosulfuron-methyl, metazosulfuron, nicosulfuron, ortho-sulfamuron, oxasulfuron, primisulfuron, primisulfuron-methyl, promethazinesulfuron pyrisulfuron, pyrazosulfuron, pyrazosulfuron-ethyl, rimsulfuron, sulfometuron, sulfometuron-methyl, sulfosulfuron, trifluridinesulfuronfloxysulfuron, trifloxysulfuron-sodium salt, chlorsulfuron, cinosulfuron, ethametsulfuron, ethametsulfuron-methyl, iodosulfuron, iodosulfuron-methyl-sodium, iofensulfuron, iofensulfuron-sodium, metsulfuron, metsulfuron-methyl, prosulfuron, thifensulfuron, thifensulfuron-methyl, triasulfuron, trisulfuron enuron, tribenuron-methyl, trifle-sulfuron, triflusulfuron-methyl, tritosulfuron, bencarbazone, flucarbazone, flucarbazone-sodium salt, propoxycarbazone, propoxycarbazone-sodium salt, thiencarbazone, thiencarba-zone-methyl, cloransulam, cloransulam-methyl, diclosulam, and florasulam. m), flumetsulam, metosulam, penoxsulam, pyroxsulam, imazamethabenz, imazamethabenz-methyl, imazamox, imazamox-ammonium salt, imazapic, imazapic-ammoniumsalt), imidazolium salt, imidazolium-isopropylammonium salt, imidazolium-quinoline acid, imidazolium-ammonium, imazethapyr, imazethapyrammonium, and their agriculturally acceptable salts and derivatives.

[0042] In another embodiment, group B-2 includes herbicides selected from group B: clodinafop, clodinafop-propargyl, cyhalofop, cyhalofop-butyl, diclofop, diclofop-methyl, fenoxaprop, fenoxaprop-ethyl, fenoxaprop-P, fenoxaprop-P-ethyl, fluazifop, fluazifop-butyl, fluazifop-P, fluazifop-P-butyl, and pyrazosulfuron-methyl. Haloxyfop, haloxyfop-methyl, haloxyfop-P, haloxyfop-P-methyl, metamifop, propaquizafop, quizalofop, quizalofop-ethyl, quizalofop-P, quizalofop-P-ethyl, alloxydim, clethodim, sethoxydim, tepraloxydim, tralkoxydim, pinoxaden, flufenoximacil, and their agriculturally acceptable salts and derivatives.

[0043] In another embodiment, group B-3 includes herbicides selected from group B: azafenidin, oxadiazon, oxadiargyl, carfentrazone, carfentrazone-ethyl, saflufenacil, cinidon, cinidon-ethyl, sulfentrazone, pyraclonil, piraflufen, piraflufen-ethyl, and butafe. nacil), fluazolate, fluthiacet, fluthiacet-methyl, flufenpyr, flufenpyr-ethyl, flumiclorac, flumiclorac-pentyl, flumioxazin, trifludimoxazin, pentoxazone, oxyfluorfen, acifluorfen, acifluorfen-sodium Herbicides including salts, aclofen, chlormethoxynil, chlornitrofen, nitrofen, bifenox, fluoroglycofen, fluoroglycofen-ethyl, fomesafen, fomesafen-sodium salt, lactofen, tiafenacil, epyrifenacil, and their agriculturally acceptable salts and derivatives.

[0044] In another embodiment, group B-4 includes herbicides selected from group B: benzobicyclon, bicyclopyrone, mesotrione, sulcotrione, tefuryltrione, tembotrione, isoxachlortole, isoxaflutole, benzofenap, pyrasulfotole, pyrazolynate, pyrazoxyfen, fenquinotrione, toramezone, tolpyralate, lancotrione, and lancotrione-sodium. Salt), flusulfinam, bipyrazone, fenpyrazone, cypyrafluone, tripyrasulfone, 2-methyl-N-(5-methyl-1,3,4-oxadiazol-2-yl)-3-(methylsulfonyl)-4-(trifluoromethyl)benzamide (CAS Registry No.: 1400904-50) -8), 2-chloro-N-(1-methyl-1H-triazol-5-yl)-3-(methylthio)-4-(trifluoromethyl)benzamide (CAS Registry No.: 1361139-71-0), 4-(4-fluorophenyl)-6-[(2-hydroxy-6-oxo-1-cyclohexen-1-yl)carbonyl]-2-methyl-1,2,4-triazine-3,5(2H,4H)-dione (CAS Registry No.: 1353870-34-4), and their agriculturally acceptable salts and derivatives.

[0045] In another embodiment, group B-5 includes herbicides selected from group B: diflufenican, picolinafen, beflubutamid, norflurazon, fluridone, flurochloridone, flurtamone, and their agriculturally acceptable salts and derivatives.

[0046] In another embodiment, group B-6 includes herbicides selected from group B: ioxynil, ioxynil-octanoate, bentazone, pyridate, bromoxynil, bromoxynil-octanoate, chlorotoluron, dimefuron, diuron, linuron, fluometuron, isoproturon, isouron, tebuthiuron, benzthiazuron, methabenzthiazuron, propanil, metobromuron, metoxuron, and monolinuron. Silduron, simazine, atrazine, propazine, cyanazine, ametryn, simetryn, dimethametryn, prometryn, terbumeton, terbuthylazine, terbutryn, trietazine, hexazinone, metamitron, metribuzin, amicarabazone, bromacil, lenacil, terbacil, chloridazon, desmedipham, phenmedipham, and their agriculturally acceptable salts and derivatives.

[0047] In another embodiment, group B-7 includes herbicides selected from group B: propachlor, metazachlor, alachlor, acetochlor, metolachlor, butachlor, pretilachlor, thenylchlor, indanofa n, cafenstrole, fentrazamide, dimethenamid, dimethenamid-P, mefenacet, pyroxasulfone, fenoxasulfone, naproanilide, napropamide, anilofos, flufenacet, ipfencarbazone, and their agriculturally acceptable salts and derivatives.

[0048] In another embodiment, group B-8 includes herbicides selected from group B: trifluralin, pendimethalin, ethalfluralin, benfluralin, oryzalin, prodiamine, butamifos, dithiopyr, thiazopyr, and their agriculturally acceptable salts and derivatives.

[0049] In another embodiment, group B-9 comprises herbicides selected from group B: 2,4-dichlorophenoxyacetic acid (2,4-D) and its salts and esters, 4-(2,4-dichlorophenoxy)butyric acid (2,4-DB) and its salts or esters (dimethylammonium salt, isooctyl ester and choline salt), 3,6-dichloro-2-methoxybenzoic acid (Dicamba) and its salts (dicholine or N,N-bis-(3-aminopropyl)methylamine salt), 2-methyl-4-chlorophenoxyacetic acid (MCPA) and its salts or esters (dimethylammonium salt, 2-ethylhexyl ester, isooctyl ester, sodium salt and choline salt), 4-(4-chloro-o-tolyloxy) Butyric acid (MCPB), mecoprop and its salts or esters (dimethylammonium salt, diethanolamine salt, ethylene glycol bis(trichloroacetate), 2-ethylhexyl ester, isooctyl ester, methyl ester, potassium salt, sodium salt, triethanolamine salt and choline salt), mecoprop-P and its salts or esters (dimethylammonium salt, 2-ethylhexyl ester, isooctyl ester, potassium salt and choline salt), dichlorprop and its salts or esters (butoxy ester, dimethylammonium salt, 2-ethylhexyl ester, isooctyl ester, methyl ester, potassium salt, sodium salt and choline salt), dichlorprop-P, and other dichlorprop compounds. Dichlorprop-Pdimethylammonium, trichloropyr and its salts or esters (butoxy ester and triethylammonium salt), fluroxypyr, fluroxypyr-meptyl, picloram and its salts (potassium salt, tris(2-hydroxypropyl)ammonium salt and choline salt), quinclorac, quinmerac, and aminopyralid. It and its salts (potassium salt, tri(2-hydroxypropyl)ammonium salt and choline salt), clopyralid and its salts (ethanolamine salt, potassium salt, triethylammonium salt and choline salt), clonateprop, aminocyclopyrachlor, halauxifen, halauxifen-methyl, florpyrauxifen and florpyrauxifenben, as well as their agriculturally acceptable salts and derivatives.

[0050] In another embodiment, Group B-10 includes herbicides selected from Group B: glyphosate, glyphosate-isopropylammonium salt, glyphosate-trimesium salt, glyphosate-ammonium salt, glyphosate-diammonium salt, glyphosate-dimethylammonium salt, glyphosate-monoethanolamine salt, glyphosate-sodium salt, glyphosate-potassium salt, glyphosate-guanidine salt, and other agriculturally acceptable salts and derivatives thereof.

[0051] In another embodiment, Group B-11 includes herbicides selected from Group B: glufosinate, glufosinate-ammonium salt, glufosinate-P, glufosinate-P-sodium salt, and bialaphos, as well as their agriculturally acceptable salts and derivatives.

[0052] In another embodiment, group B-12 includes herbicides selected from group B: isoxaben, dichlobenil, methioz olin, diallate, butylate, triallate, chlorpropham, asulam, phenisopham, benthiocarb, molinate, esprocarb, pyributicarb, prosulfocarb, orbencarb, ethylthioalkyl-N,N-dipropylformamide (EPTC), dimepiperate, swep, and difenoxyl. ron), methyldymron, bromobutide, daimuron, cumyluron, diflufenzopyr, diflufenzopyr-sodium salt, etobenzanid, tridiphane, amitrol, clonazol, broclo zone, 2-[(2,4-dichlorophenyl)methyl]-4,4-dimethylisoxazoline-3-one (CAS Registry No.: 81777-95-9), (3S,4S)-N-(2-fluorophenyl)-1-methyl-2-oxo-4-[3-(trifluoromethyl)phenyl]-3-pyrrolidinecarboxamide (CAS Registry No.: 2053901-33-8), maleic hydantoin. drazide, oxaziclomefone, cinmethylin, benfuresate, dalapon, chlorthiamid, flup oxam, bensulide, paraquat, paraquat-dichloride, diquat, diquat-dibromide, monosodium methanesulfonate (MSMA), indaziflam, and triaziflam, as well as their agriculturally acceptable salts and derivatives.

[0053] In another embodiment, the herbicidal composition comprises a safener selected from group C: benoxacor, cloquintocet, cyometrinil, cyprosulfamide, dichlormid, dicyclonone, dietholate, fenchlorazole, fenclorim, flurazole, fluxofenim, furilazole, isoxadifen, mefenpyr, mephenate, and naphthalic anhydride. anhydride), oxabetrinil, 4-(dichloroacetyl)-l-oxa-4-azaspiro[4.5]decane, 2,2,5-trimethyl-3-(dichloroacetyl)-l,3-oxazolidine and N-(2-methoxybenzoyl)-4-[(methylaminocarbonyl)amino]benzenesulfonamide.

[0054] On the other hand, a method for controlling weeds is provided, comprising applying a composition comprising a compound of formula (I), a herbicide compound from group B, and optionally a safener from group C, to a location where weeds are growing or will grow in crop fields, vegetable fields, land under perennial crops, non-crop land, etc. In crop fields and vegetable fields, the composition of the present invention can be applied before, simultaneously with, and / or after sowing crop seeds.

[0055] In one embodiment, the composition of the present invention relates to a method for controlling 'voluntary' crops. Such 'voluntary' crops are defined as undesirable seedlings and plants derived from seeds, tubers, roots, or other plant parts and organs, which remain in the field from previous tillage and planting practices. For example, in one embodiment, the present invention relates to controlling voluntary maize (Zea mays) in areas where maize growth is undesirable. An example of undesirable voluntary maize growth is in soybean-grown fields.Other examples include methods for controlling voluntary crops such as sorghum (Sorghum bicolor), wheat (Triticum aestivum), durum wheat (Triticum turgidum spp. durum), rye (Secalecereale), triticale (Triticosecale Wittmack), barley (Hordeum vulgare), oats (Avena sativa), millet (Setariaitalica), carinata (Brassica carinata), flaxseed (Camelina sativa), and rapeseed (Canola). The following are listed: napus, flax, soybean, cotton, industrial hemp, dragon bone mustard, sugarcane, potato, rice, alfalfa, thlaspi arvense, clover, sunflower, and peanut.

[0056] In another embodiment, the composition is a formulation prepared by mixing a compound of formula (I) and at least one compound selected from the herbicide compound group B and optionally the safener group C with a carrier (such as a solid or liquid carrier) and adding, as needed, adjuvants (such as surfactants) for formulation. Preferred formulation types of such formulations are aqueous liquid suspension concentrates, wettable powders, water-dispersible particles, granules, and emulsifiable concentrates. The compositions of the present invention can be used in combination with formulations containing another herbicide as an active ingredient.

[0057] In another embodiment, the total content of the compound of formula (I) and at least one compound selected from herbicide group B and safener group C in the composition of the present invention is generally in the range of 0.01% by weight to 90% by weight. In another embodiment, the total content of the compound of formula (I) is 1% by weight to 80% by weight. When at least one compound selected from herbicide group B is a salt (e.g., glyphosate-potassium salt), the weight of at least one compound is expressed in acid equivalent.

[0058] In some embodiments, the mixing ratio of the compound of formula (I) with at least one compound selected from group B of herbicides includes, by weight, about 1:0.1, about 1:0.2, about 1:0.3, about 1:0.5, about 1:0.6, about 1:0.7, about 1:0.8, about 1:1, about 1:1.2, about 1:1.4, about 1:1.6, about 1:1.8, about 1:2, about 1:2.2, about 1:2.4, about 1:2.6, about 1:2.8, about 1:3, about 1:5, about 1:7, about 1:10, about 1:15, about 1:20, about 1:30, and about 1:50. The term “about” means that the specified ratio includes ratios within the range of 10% by weight increase or decrease relative to the specified ratio. For example, a ratio of about 1:2 includes the range of 1:1.8 to 1:2.2.

[0059] In some embodiments, the combination of compound (I) and a herbicide selected from herbicide group B includes: a combination of compound (I) and pyrimethanil (1:0.1 to 1:20); a combination of compound (I) and pyrimethanil sodium salt (1:0.1 to 1:20); a combination of compound (I) and chlorpyrifos-ethyl (1:0.1 to 1:20); a combination of compound (I) and formamidesulfuron (1:0.1 to 1:20); a combination of compound (I) and chlorpyrifos-methyl (1:0.1 to 1:20); a combination of compound (I) and nicosulfuron (1:0.1 to 1:20); a combination of compound (I) and fluchlorosulfuron-methyl (1:0.1 to 1:20); a combination of compound (I) and... Combinations of compound (I) and sulfadiazine (1:0.1 to 1:20); combinations of compound (I) and triflusulfonyl-sodium (1:0.1 to 1:20); combinations of compound (I) and trifluralin (1:0.1 to 1:20); combinations of compound (I) and chlorsulfuron (1:0.1 to 1:20); combinations of compound (I) and iodosulfuron-methyl-sodium (1:0.1 to 1:20); combinations of compound (I) and iodosulfuron-sodium (1:0.1 to 1:20); combinations of compound (I) and mesosulfuron-methyl (1:0.1 to 1:20); combinations of compound (I) and flusulfuron (1:0.1 to 1:20); combinations of compound (I) and thiasulfuron-methyl (1:0.1 to 1:20). Combinations of formula (I) and bensulfuron-methyl (1:0.1 to 1:20); combinations of formula (I) and thiamethoxam-methyl (1:0.1 to 1:20); combinations of formula (I) and chlorpyrifos-methyl (1:0.1 to 1:20); combinations of formula (I) and flusulfanilamide (1:0.1 to 1:20); combinations of formula (I) and imidacloprid-methyl (1:0.1 to 1:20); combinations of formula (I) and methoxyfenozide-ammonium salt (1:0.1 to 1:20); combinations of formula (I) and imidacloprid-ammonium salt (1:0.1 to 1:20); combinations of formula (I) and imidacloprid-ammonium salt (1:0.1 to 1:20); combinations of formula (I) and imidacloprid-isopropylammonium salt (1:0.1 to 1:20). Combinations of formula (I) and imidazoline ammonium salt (1:0.1 to 1:20); combinations of formula (I) and imidazoline ammonium salt (1:0.1 to 1:20); combinations of formula (I) and oxazolin-ethyl (1:0.1 to 1:20); combinations of formula (I) and quizalofop-P-ethyl (1:0.1 to 1:20); combinations of formula (I) and fluroxypyr-butyl (1:0.1 to 1:20); combinations of formula (I) and quizalofop-P-ethyl (1:0.1 to 1:20); combinations of formula (I) and quizalofop-P-ethyl (1:0.1 to 1:20); combinations of formula (I) and quizalofop-P-ethyl (1:0.1 to 1:20).Combinations of formula (I) and clethodim (1:0.1 to 1:20); combinations of formula (I) and clethodim (1:0.1 to 1:20); combinations of formula (I) and clethodim (1:0.1 to 1:20); combinations of formula (I) and triadimefon-ethyl (1:0.1 to 1:20); combinations of formula (I) and pyrimethanil (1:0.1 to 1:20); combinations of formula (I) and methanesulfonamide (1:0.1 to 1:20); combinations of formula (I) and basilyl-ethyl (1:0.1 to 1:20); combinations of formula (I) and methyl methacrylate-methyl (1:0.1 to 1:20); combinations of formula (I) and flupyridaben-ethyl (1:0.1 to 1:20). Combinations of (I) and flufenoxuron-pentyl (1:0.1 to 1:20); Combinations of (I) and propyzoxystrobin (1:0.1 to 1:20); Combinations of (I) and ethoxyflufenoxuron (1:0.1 to 1:30); Combinations of (I) and trifluralin-sodium salt (1:0.1 to 1:30); Combinations of (I) and flusulfanilamide-sodium salt (1:0.1 to 1:30); Combinations of (I) and haloxyfop-methyl (1:0.1 to 1:30); Combinations of (I) and flufenoxuron-methyl (1:0.1 to 1:30); Combinations of (I) and flupyrimisulfuron (1:0.1 to 1:20); Combinations of (I) and flupyrimisulfuron (1:0.1 to 1:20); Combinations of compound (I) and flupyradifon (1:0.1 to 1:20); combinations of compound (I) and cyclosulfonone (1:0.1 to 1:20); combinations of compound (I) and mesotrione (1:0.1 to 1:20); combinations of compound (I) and isoxaflutole (1:0.1 to 1:20); combinations of compound (I) and benzoxazolone (1:0.1 to 1:20); combinations of compound (I) and pyrazosulfuron (1:0.1 to 1:20); combinations of compound (I) and fenquinotrione (1:0.1 to 1:20); combinations of compound (I) and oxyphenazolone sodium salt (1:0.1 to 1:20); Combinations of (I) with 2-methyl-N-(5-methyl-1,3,4-oxadiazol-2-yl)-3-(methylsulfonyl)-4-(trifluoromethyl)benzamide (1:0.1 to 1:20); combinations of (I) with 2-chloro-N-(1-methyl-1H-tetrazol-5-yl)-3-(methylthio)-4-(trifluoromethyl)benzamide (1:0.1 to 1:20); combinations of (I) with 4-(4-fluorophenyl)-6-[(2-hydroxy-6-oxo-1-cyclohexen-1-yl)carbonyl]-2-methyl-1,2,4-triazine-3,5(2H,4H)-dione (1:0.1 to 1:20); and combinations of (I) with pyrazosulfuron (1:0.1 to 1:20).Combinations of formula (I) and fluazinam (1:0.1 to 1:20); combinations of formula (I) and bentazon (1:1 to 1:50); combinations of formula (I) and bromobenzonitrile octanoate (1:1 to 1:50); combinations of formula (I) and diuron (1:1 to 1:50); combinations of formula (I) and linuron (1:1 to 1:50); combinations of formula (I) and fusulin (1:1 to 1:50); combinations of formula (I) and simazine (1:1 to 1:50); combinations of formula (I) and atrazine (1:1 to 1:50); combinations of formula (I) and simazine (1:1 to 1:50). Combinations of compound (I) and atrazine (1:1 to 1:50); combinations of compound (I) and acetochlor (1:1 to 1:50); combinations of compound (I) and metolachlor (1:1 to 1:50); combinations of compound (I) and metolachlor (1:1 to 1:50); combinations of compound (I) and acetochlor (1:1 to 1:50); combinations of compound (I) and metolachlor (1:1 to 1:50); combinations of compound (I) and metolachlor (1:1 to 1:50); combinations of compound (I) and dimethyl phenoxychlor (1:1 to 1:50); combinations of compound (I) and dimethyl phenoxychlor (1:1 to 1:50). Combinations of formula (I) and sulfonylpyrazine (1:0.1 to 1:20); combinations of formula (I) and fluthiamethoxam (1:0.1 to 1:20); combinations of formula (I) and trifluralin (1:1 to 1:50); combinations of formula (I) and pendimethalin (1:1 to 1:50); combinations of formula (I) and butyric acid (1:1 to 1:50); combinations of formula (I) and 2,4-DB (1:1 to 1:50); combinations of formula (I) and clopyralid (1:1 to 1:50); combinations of formula (I) and isooctyl clopyralid (1:1 to 1:50). Combinations of formula (I) and potassium dichloropyridinic acid (1:1 to 1:50); combinations of formula (I) and dichloropyridinic acid-ethanolamine salt (1:1 to 1:50); combinations of formula (I) and dichloropyridinic acid-triethylammonium salt (1:1 to 1:50); combinations of formula (I) and fluorochloropyridinic acid (1:0.1 to 1:20); combinations of formula (I) and fluorochloropyridinic acid-methyl (1:0.1 to 1:20); combinations of formula (I) and chlorofluoropyroxyacetic acid (1:0.1 to 1:20); combinations of formula (I) and chlorofluoropyroxyacetic acid-benzyl (1:0.1 to 1:20).Combinations of formula (I) and glyphosate (1:1 to 1:50); combinations of formula (I) and glyphosate-isopropylammonium salt (1:1 to 1:50); combinations of formula (I) and glyphosate-ammonium salt (1:1 to 1:50); combinations of formula (I) and glyphosate-dimethylamine salt (1:1 to 1:50); combinations of formula (I) and glyphosate-monoethanolamine salt (1:1 to 1:50); combinations of formula (I) and glyphosate-potassium salt (1:1 to 1:50); combinations of formula (I) and glyphosate-dimethylamine salt (1:1 to 1:50). Combinations of guanidine salts (1:1 to 1:50); combinations of compound (I) and glufosinate (1:1 to 1:50); combinations of compound (I) and glufosinate-sodium salt (1:1 to 1:50); combinations of compound (I) and EPTC (1:1 to 1:50); combinations of compound (I) and flupyridine hydrazone (1:1 to 1:50); combinations of compound (I) and flupyridine hydrazone-sodium salt (1:1 to 1:50); combinations of compound (I) and isoxaflutole (1:1 to 1:50). Combinations of formula (I) and 2-[(2,4-dichlorophenyl)methyl]-4,4-dimethylisoxazolidin-3-one (1:1 to 1:50); combinations of formula (I) and (3S,4S)-N-(2-fluorophenyl)-1-methyl-2-oxo-4-[3-(trifluoromethyl)phenyl]-3-pyrrolidinecarboxamide (1:1 to 1:50); combinations of formula (I) and cycloheptaquiloether (1:1 to 1:50); combinations of formula (I) and MSMA (1:1 to 1:50); combinations of formula (I) and MSMA (1:1 to 1:50). Combinations of compound (I) with paraquat (1:1 to 1:50); combinations of compound (I) with paraquat-dichloride (1:1 to 1:50); combinations of compound (I) with diquat (1:1 to 1:50); combinations of compound (I) with diquat-dibromide (1:0.1 to 1:20); combinations of compound (I) with cyclopropanesulfonamide (1:0.1 to 1:20); and combinations of compound (I) with bis(oxazolyl)-ethyl (1:0.1 to 1:20).

[0060] In one embodiment, the herbicide selected from herbicide group B is glyphosate, and the weight ratio of compound 1 to glyphosate is from about 30:60 to 1000:1120.

[0061] In another embodiment, the herbicide selected from herbicide group B is sulfopyrazine, and the weight ratio of compound 1 to sulfopyrazine is about 15:60 to 90.

[0062] In another embodiment, the herbicide selected from herbicide group B is mesotrione, and the weight ratio of compound 1 to mesotrione is about 30:60 to 105:210.

[0063] In another embodiment, the herbicide selected from herbicide group B is glufosinate, and the weight ratio of compound 1 to glufosinate is about 30:60 to 450.

[0064] In another embodiment, the herbicide selected from herbicide group B is dicamba, and the weight ratio of compound 1 to dicamba is about 30:60 to 280.

[0065] In another embodiment, the herbicide selected from herbicide group B is 2,4-D acid, and the weight ratio of compound 1 to 2,4-D acid is from about 30:60 to 280.

[0066] In another embodiment, the herbicide selected from herbicide group B is a 2,4-D ester, and the weight ratio of compound 1 to the 2,4-D ester is from about 30:60 to 280.

[0067] In another embodiment, the herbicide selected from herbicide group B is S-metolachlor, and the weight ratio of compound 1 to S-metolachlor is about 30 to 1000.

[0068] In yet another embodiment, the herbicide selected from herbicide group B is metribuzin, and the weight ratio of compound 1 to metribuzin is about 30 to 210.

[0069] In one embodiment, the undesirable vegetation treated with the composition of the present invention comprises protoporphyrinogen IX oxidase (PPO) inhibitor-resistant weeds. In another embodiment, the PPO inhibitor-resistant weeds have the dG210 mutation.

[0070] Before, during, and / or after sowing crop seeds treated with one or more compounds selected from the group consisting of insecticides, nematicides, fungicides, etc., a composition containing a compound of formula (I) may be applied to a field containing crop seeds that have been sown or will be sown. Such compounds include neonicotinoids, diamides, carbamates, organophosphates, bionematicides, azoles, strobilurin compounds, metalaxyl compounds, and SDHI compounds.

[0071] Examples of crop fields treated with compositions containing compounds of formula (I) include food crop fields, such as peanut fields, soybean fields, corn fields and wheat fields; forage crop fields, such as sorghum fields and oat fields; industrial crop fields, such as cotton fields and rapeseed fields; and sugar crop fields, such as sugarcane fields and sugar beet fields.

[0072] Examples of vegetable fields treated with the composition include fields for cultivating solanaceous vegetables (eggplant, tomato, bell pepper, chili pepper, potato, etc.), fields for cultivating cucurbitaceous vegetables (cucumber, pumpkin, zucchini, watermelon, cantaloupe, etc.), and fields for cultivating cruciferous vegetables (radish, turnip, horseradish, cabbage, Chinese cabbage). Fields for cultivating cabbage, mustard greens, broccoli, cauliflower, etc.; fields for cultivating chrysanthemum vegetables (burdock, garland chrysanthemum, artichoke, lettuce, etc.); fields for cultivating lily vegetables (leeks, onions, garlic, and asparagus); fields for cultivating umbelliferous vegetables (carrots, parsley, celery, parsnip, etc.); fields for cultivating chenopodiaceae vegetables (spinach, Swiss chard, etc.); fields for cultivating mint vegetables (perilla, mint, basil, and lavender); strawberry fields; sweet potato fields; yam fields; and taro fields.

[0073] Examples of land under perennial crops treated with compositions containing compounds of formula (I) include orchards, tea plantations, mulberry fields, coffee fields, banana fields, palm fields, flowering tree companies, flowering tree fields, cultivated plant fields, nursery fields, woodlands, and gardens. Examples of orchard trees include pome fruits (apples, pears, Japanese pears, Chinese quince, etc.), stone fruits (peaches, plums, nectarines, Japanese apricots, cherries, apricots, plums, etc.), citrus fruits (citrus unshiu, oranges, lemons, limes, grapefruits, etc.), nut trees (chestnuts, walnuts, hazelnuts, almonds, pistachios, cashews, macadamia trees, etc.), berries (grapes, blueberries, cranberries, blackberries, raspberries, etc.), Japanese persimmons, olives, loquats, etc.

[0074] Examples of non-crop land treated by compositions containing compounds of formula (I) include sports fields, open spaces, railway edges, parks, parking lots, road edges, dried-up riverbeds, land under power lines, residential land, and factory sites.

[0075] The crop cultivated in crop fields treated with the composition containing compound (I) is unrestricted, provided that the crop is a variety normally cultivated as a crop. It can be a plant that can be produced through natural hybridization, a plant that can be produced through mutation, an F1 hybrid, or a transgenic plant (also known as a genetically modified plant). The plant typically possesses characteristics such as: acquiring tolerance to herbicides, accumulating toxic substances to pests, suppressing susceptibility to diseases, increasing yield potential, improving tolerance to biotic and abiotic stresses, accumulating substances, and improving preservation and processing properties.

[0076] Examples of plants conferred herbicide tolerance through genetic engineering include those conditioned with: 4-hydroxyphenylpyruvate dioxygenase (HPPD) inhibitors, such as isoxaflutole and mesotrione; acetyllactone synthase (ALS) inhibitors, such as imidazolinone herbicides containing imazalil and sulfonylurea herbicides containing thifensulfuron-methyl; 5-enolpyruvate-3-phosphate synthase (EPSP) inhibitors, such as glyphosate; glutamine synthase inhibitors, such as glufosinate; auxin herbicides, such as 2,4-D and dicamba; and oxadiazine herbicides containing bromobenzonitrile. Herbicide-tolerant genetically modified plants include cereals such as wheat, barley, rye and oats, canola, sorghum, soybeans, rice, rapeseed, sugar beets, sugarcane, grapes, lentils, sunflowers, alfalfa, pome fruits, stone fruits, coffee, tea, strawberries, turfgrass, tomatoes, potatoes, cucumbers, and vegetables such as lettuce, with herbicide-tolerant genetically modified plants being more preferably cereals such as wheat, barley, rye and oats, soybeans, rice, grapes, tomatoes, potatoes, and pome fruits.

[0077] Specific herbicide-tolerant plants treated with compositions containing compounds of formula (I) include glyphosate-tolerant plants. To obtain glyphosate-tolerant plants, one or more genes are introduced into the following: a glyphosate-tolerant EPSPS gene (CP4 epsps) from Agrobacterium tumefaciens strain CP4; a glyphosate-metabolizing enzyme gene (glyphosate N-acetyltransferase) from Bacillus Ucheniformis with enhanced metabolic activity via shuffling technology (gat4601, gat4621); a glyphosate-metabolizing enzyme gene (glyphosate oxidase gene, goxv247) from Ochrobacter umanthropi strain LBAA; and a glyphosate-tolerant mutant EPSPS gene (mepsps, 2mepsps) from maize. Key examples of such modified plants include alfalfa (Medicago sativa), Argentine canola (Brassica napus), cotton (Gossypium hirsutum L.), creeping bentgrass (Agrostis stolonifera), corn (Zea mays L.), Polish canola (Brassica rapa), potato (Solanumtuberosum L.), soybean (Glycine max L.), sugar beet (Betavulgaris), and wheat (Triticum aestivum). Some glyphosate-tolerant transgenic plants are commercially available. For example, genetically modified plants expressing glyphosate-tolerant EPSPS from Agrobacterium can be used in applications such as "Roundup". The product name is "[Brand Name]", which is commercially available. Genetically modified plants expressing glyphosate-metabolizing enzymes from Bacillus and possessing enhanced metabolic activity through shuffling technology can be produced using products such as "[Brand Name]". GAT TM "or" Commercially available under the trade name "Gly Canola," and genetically modified plants expressing glyphosate-tolerant mutant EPSPS from maize can be sold under the trade name "GlyTol." TM "Acquired through commercial purchase."

[0078] Other herbicide-tolerant plants treated with compositions containing compounds of formula (I) include glufosinate-tolerant herbicide plants. To obtain glufosinate-tolerant plants, one or more genes are introduced as glufosinate-metabolizing enzymes: the phosphinic acid N-acetyltransferase (PAT) gene (bar) from *Streptomyces hygroscopicus*, the phosphinic acid N-acetyltransferase (PAT) gene (pat) from *Streptomyces viridochromogenes*, and the synthetic pat gene (pat syn) from *Streptomyces viridochromogenes* strain Tu494. Major examples of this plant include Argentine rapeseed (Brassica napus), chicory (Cichorium intybus), cotton (Gossypium hirsutum L.), corn (Zeamays L.), Polish rapeseed (Brassica rapa), rice (Oryza sativa L.), soybean (Glycine max L.), and sugar beet (Beta vulgaris). Some genetically modified plants with glufosinate tolerance are commercially available. Genetically modified plants with glufosinate-metabolizing enzymes (bar) from *Streptomyces hygroscopicus* and *Streptomyces viridans* can be produced using products such as "LibertyLink". TM “InVigor” TM "or WideStrike" TM The product name was obtained through a merchant purchase.

[0079] Herbicide-tolerant plants treated with compositions containing compounds of formula (I) also include plants tolerant to benzonitrile herbicides (e.g., bromobenzonitrile-tolerant). Transgenic bromobenzonitrile-tolerant plants incorporating a nitrile hydrolase gene (bx n) include those possessing benzonitrile herbicide-metabolizing enzymes from *Klebsiella pneumoniae* subsp. *ozaenae*. Examples of this include Argentine rapeseed (*Brassica napus*), cotton (*Gossypium hirsutum* L.), and tobacco (*Nicotiana tabacum* L.). Such plants can be used as "Navigator" TM canola or BXN TM The product name was obtained through a merchant purchase.

[0080] Herbicide-tolerant plants treated with compositions containing compounds of formula (I) also include ALS herbicide-tolerant plants, such as carnations (Dianthus caryophyllus), in which the ALS herbicide-tolerant ALS gene (surB) from tobacco (Nicotiana tabacum) is introduced as a selection marker, and can be marketed under the trade name "Moondust". TM "Moonshadow" TM "Moonshade" TM "Moonlite" TM "Moonaqua" TM "Moonvista" TM "Moonique" TM "Moonpearl" TM "Moonberry" TM "and Moonvelvet" TM "Commercially available; Flax (Linum usitatissumum L.) with the introduction of the ALS herbicide-resistant ALS gene (als) from Arabidopsis thaliana, and commercially available under the trade name "CDCTriffid Flax"; Sulfonylurea- and imidazolinone-resistant maize (Zea mays L.) with the introduction of the ALS herbicide-resistant ALS gene (zm-hra) from maize, and commercially available under the trade name "Optimum"." TM GAT TM "Commercially acquired; imidazolinone-tolerant soybeans, in which the ALS herbicide-tolerant ALS gene (csrl-2) from Arabidopsis thaliana has been introduced, and can be marketed under the trade name "Cultivance" TM "Commercially acquired; sulfonylurea herbicide-tolerant soybeans, incorporating the ALS herbicide-tolerant ALS gene (gm-hra) from soybean (Glycine max) and available under the trade name 'Treus'." TM "Plenish" TM "and Optimum GAT" TM"Commercially acquired; and cotton, in which the ALS herbicide-resistant ALS gene (S4-FlrA) from tobacco (Agrobacterium tabacumcv.Xanthi) was introduced."

[0081] Herbicide-tolerant plants treated with compositions containing compounds of formula (I) also include HP PD herbicide-tolerant plants, such as soybeans, wherein the nicosulfuron-tolerant HPPD gene (avhppd03) and the benzyladenin N-acetyltransferase (PAT) enzyme gene (pat) from oat (Avena sativa) are introduced simultaneously, and nicosulfuron-tolerant soybeans have glufosinate-metabolizing enzymes from Streptomyces viride and are commercially available under the trade name "Herbicide-tolerant Soybean line".

[0082] Herbicide-tolerant plants treated with compositions containing compounds of formula (I) also include 2,4-dichlorophenoxyacetic acid (2,4-D)-tolerant plants, such as maize, wherein the aryloxyalkylanoic acid dioxygenase gene (aad-1) as a 2,4-D metabolic enzyme from the herbicide *Sphingobium herbicidovorans* is introduced, and can be marketed under the trade name "Enlist". TM Commercially available under the brand name "Maize"; as well as soybeans and cotton, which incorporate the aryloxyalkylane dioxygenase gene (aad-12) as a 2,4-D metabolic enzyme from *Delftia acidovorans*, and are available under the trade name "Enlist". TM Purchased from Soybean.

[0083] Herbicide-tolerant plants treated with compositions containing compounds of formula (I) also include dicamba-tolerant plants such as soybeans and cotton, wherein the dicamba monooxygenase gene (dmo) as a dicamba metabolic enzyme from the Stenotrophomonas maltophilia strain DI-6 is introduced; soybean (Glycine max L.) wherein the glyphosate-tolerant EPSPS gene (CP4 epsps) from the Agrobacterium tumefaciens strain CP4 is introduced simultaneously with the above gene, and can be marketed under the trade name "Genuity". TM Roundup Ready TM 2 Xtend TM "Acquired through commercial purchase."

[0084] Examples of commercially available transgenic plants that have been conferred herbicide tolerance and can be treated with compositions containing compounds of formula (I) include glyphosate-tolerant maize “Roundup Ready Com”, “Roundup Ready2”, “Agrisure GT”, “Agrisure GT / CB / LL”, “Agrisure GT / RW”, “Agrisure 3000GT”, “YieldGard VT Rootworm / RR2”, and “YieldGard VT Triple”; glyphosate-tolerant soybeans “Roundup Ready Soybean” and “Optimum GAT”; glyphosate-tolerant cottons “Roundup Ready Cotton” and “Roundup Ready Flex”; glyphosate-tolerant rapeseed “Roundup Ready Canola”; glyphosate-tolerant alfalfa “Roundup Ready Alfalfa”; glyphosate-tolerant rice “Roundup Ready Rice”; and glufosinate-tolerant maizes “Roundup Ready2”, “Liberty Link”, “Eierculex 1”, and “Eierculex”. RW, EierculexXtra, Agrisure GT / CB / LL, Agrisure CB / LL / RW and Bt10; glufosinate-tolerant cotton FiberMax Liberty Link; glufosinate-tolerant rice Liberty Link Rice; glufosinate-tolerant rapeseed in Vigor; glufosinate-tolerant rice Liberty Link Rice; bromobenzonitrile-tolerant cotton BXN; bromobenzonitrile-tolerant rapeseed Navigator and Compass; and glufosinate-tolerant rapeseed InVigor.

[0085] Other plants that can be modified against herbicides are widely known and can be treated with compositions containing compounds of formula (I). Examples include glyphosate-tolerant alfalfa, apple, barley, eucalyptus, flax, grape, lentil, rapeseed, pea, potato, rice, sugar beet, sunflower, tobacco, tomato, turfgrass, and wheat (see, for example, U.S. Patent Nos. 5,188,642, 4,940,835, 5,633,435, 5,804,425, and 5,627,061); and dicamba-tolerant legumes, cotton, soybean, pea, potato, sunflower, tomato, tobacco, corn, sorghum, and sugarcane (see, for example, WO2008051633, U.S. Patent Nos. 5,188,642, 4,940,835, 5,633,435, 5,804,425, and 5,627,061). U.S. Patents 7,105,724 and 5,670,454); soybeans, sugar beets, potatoes, tomatoes, and tobacco tolerant to glufosinate (see, for example, U.S. Patents 6,376,754, 5,646,024, and 5,561,236); cotton, peppers, apples, tomatoes, sunflowers, tobacco, potatoes, corn, cucumbers, wheat, soybeans, sorghum, and cereals tolerant to 2,4-D (see, for example, U.S. Patents 6,153,401, 6,100,446, WO2005107437, U.S. Patents 5,608,147, and 5,670,454); and herbicides tolerant to acetyllactate synthase (ALS) inhibitors (e.g., Rapeseed, corn, millet, barley, cotton, mustard, lettuce, lentils, melon, millet, oats, sword beans, potatoes, rice, rye, sorghum, soybeans, sugar beets, sunflowers, tobacco, tomatoes, and wheat resistant to sulfonylurea and imidazolinone herbicides (see, for example, U.S. Patent Nos. 5,013,659, WO2006060634, 4,761,373, 5,304,732, 6,211,438, 6,211,439, and 6,222,100); rice resistant to imidazolinone herbicides, examples including rice with specific mutations (e.g., S653N) in the acetolactate synthase gene (acetylhydroxy acid synthase gene). Rice containing S654K, A122T, S653(At)N, S654(At)K, and A122(At)T (see, for example, US2003 / 0217381 and WO200520673); and barley, sugarcane, rice, corn, tobacco, soybean, cotton, rapeseed, sugar beet, wheat, and potato resistant to HPPD inhibitor herbicides (e.g., isoxazole herbicides (such as isoxaflutole), triketone herbicides (such as sulfadiazine or mesotrione), pyrazole herbicides (such as pyrazosulfuron-methyl), or as a decomposition product of isoxaflutole, diketone nitrile) (see, for example, WO2004 / 055191, WO199638567, WO1997049816, and US 6,791,014).

[0086] Examples of plants that can be conferred herbicide tolerance through classical techniques or genomic breeding techniques involving the treatment of compositions containing compounds of formula (I) include rice tolerant to imidazolinone-based ALS inhibitor herbicides such as imidacloprid or methoxyfenozide.

[0087] Rice", wheat" Wheat, sunflower Sunflower, lentils lentils and rapeseed "canola" (manufactured by BASF SE); soybeans resistant to sulfonyl-based ALS inhibitor herbicides (such as thiamethoxam-methyl). "soybean"; maize tolerant to acetyl-CoA carboxylase inhibitors (such as triketone oxime herbicides or aryloxyphenoxypropionic acid herbicides); oxadiazine-tolerant corn. "corn" and "Poast" "corn"; sunflowers tolerant to sulfonylurea herbicides (such as bensulfuron-methyl). Provisia rice, resistant to acetyl-CoA carboxylase inhibitors (such as quizalofop-p-ethyl) TM "Rice"; and "Triazine Tolerant Canola", a rapeseed variety resistant to PSII inhibitors.

[0088] Examples of plants that can be conferred herbicide tolerance through genome editing techniques involving compositions containing compounds of formula (I) include rapeseed 'SU', which is tolerant to sulfonylurea herbicides. This involved the use of rapid varietal development technology (rapid trait development system). ). Oligonucleotide-directed mutagenesis, corresponding to genome editing technologies, and through RTDS, it is possible to introduce mutations into plant DNA via gene repair oligonucleotides (GRONs) (i.e., chimeric oligonucleotides of DNA and RNA without cutting the DNA). Furthermore, examples in plants include maize, which has reduced herbicide tolerance and phytic acid content by using zinc finger nucleases that lack the endogenous gene IPK1 (see, for example, Nature 459, 437-441 2009); and rice, which has been conferred herbicide tolerance using CRISPR-Cas9.

[0089] Examples of crops resistant to specific PPO inhibitors that can be treated with compositions containing compounds of formula (I) include crops conferred with PPOs having a reduced affinity for the inhibitors through genetic engineering. Alternatively, the crop may contain substances, alone or in combination with the aforementioned PPOs, that detoxify and break down PPO inhibitors via cytochrome P450 monooxygenases. Tolerant crops are described, for example, in patent literature such as WO2011085221, WO2012080975, WO2014030090, WO2015022640, WO2015022636, WO2015022639, WO2015092706, WO2016203377, WO2017198859, WO2018019860, WO2018022777, WO2017112589, WO2017087672, WO2017039969 and WO2017023778, and in non-patent literature Li & Nicholl, Pest Management Science (2005), Vol. 61, pp. 277-285.

[0090] Examples of plants that can be treated with compositions containing compounds of formula (I) include those plants in which herbicide tolerance is conferred through novel breeding techniques, wherein the characteristics of GM rhizomes are conferred on scions through grafting breeding techniques, including glyphosate-tolerant soybean Roundup. As rootstock, non-GMO soybean scions that confer glyphosate tolerance to the rhizomes were used (see Jiang et al., Weed Technology (2013), Vol. 27, pp. 412-416).

[0091] The aforementioned plants include strains that have been endowed with two or more traits in abiotic stress tolerance, disease resistance, herbicide tolerance, pest resistance, growth traits, yield traits, nutrient uptake, product quality, and fertility traits through genetic engineering, classical breeding, genome breeding, new breeding, and genome editing technologies, as well as strains that have been endowed with two or more traits of the parent strain by hybridizing plants with the same or different characteristics.

[0092] Examples of commercially available plants that have acquired tolerance to two or more herbicides through treatment with compositions containing compounds of formula (I) include cotton "GlyTol" tolerant to glyphosate and glufosinate. TM LibertyLink TM "and GlyTol" TM LibertyLink TM "; Corn tolerant to glyphosate and glufosinate "Roundup Ready"TM LibertyLink TM Maize; Enlist soybean, tolerant to glufosinate and 2,4-D. TM Soybean; soybeans tolerant to glyphosate and dicamba. Roundup Ready (trademark) 2Xtend (trademark); Corn and soybean OptimumGAT resistant to glyphosate and ALS inhibitors. TM "; Genetically modified soybean "Enlist E3" resistant to three herbicides: glyphosate, glufosinate, and 2,4-D TM "and "Enlist TM Roundup 2 Yield”; genetically modified maize “Enlist” resistant to glyphosate, 2,4-D and aryloxyphenoxypropionate (FOP) herbicides. TM Roundup Corn 2”; a genetically modified corn variety resistant to glyphosate, 2,4-D, and aryloxyphenoxypropionate (FOP) herbicides. TM Roundup Corn 2”; a genetically modified cotton variety resistant to dicamba, glyphosate, and glufosinate, named “Bollgard”. XtendFlex TM "Cotton"; and "Enlist" – a genetically modified cotton variety resistant to three herbicides: glyphosate, glufosinate, and 2,4-D. TM "Cotton". In addition, genetically modified cotton tolerant to glufosinate and 2,4-D, cotton tolerant to both glufosinate and dicamba, maize tolerant to both glyphosate and 2,4-D, soybean tolerant to both glyphosate and HPPD herbicides, and genetically modified maize tolerant to glyphosate, glufosinate, 2,4-D, aryloxyphenoxypropionate (FOP) herbicides and cyclohexanedione (DIM) herbicides have been developed.

[0093] Examples of commercially available plants conferred herbicide tolerance and pest resistance that can be treated with compositions containing compounds of formula (I) include glyphosate-tolerant and corn borer-resistant corn "YieldGard Roundup". "and YieldGard Roundup" 2”; Corn tolerant to glufosinate and resistant to corn borer” CB / LL”; glyphosate-tolerant and resistant to maize rootworms, maize “Yield” VT Rootworm / RR2”; a corn variety resistant to glyphosate and resistant to corn rootworm and corn borer. "VTTriple"; a corn crop resistant to glufosinate and resistant to lepidopteran corn pests (Cry1F) (e.g., resistant to soybean white-edged rootworm, corn borer, black rootworm, and fall armyworm). I”; Corn resistant to glyphosate and resistant to corn rootworms” Corn Rootworm / Roundup 2”; Corn tolerant to glufosinate and resistant to coleopteran corn pests (Cry3A) (e.g., resistant to western corn rootworm, northern corn rootworm, and Mexican corn rootworm) "GT / RW"; maize tolerant to glufosinate and resistant to coleopteran maize pests (Cry34 / 35Abl) (e.g., resistant to western maize rootworm, northern maize rootworm, and Mexican maize rootworm). RW”; a glyphosate-tolerant and resistant corn rootworm “Yield” VT Rootworm / RR2”; and the cotton variety “Bollgard”, which is tolerant to dicamba, glyphosate, and glufosinate and resistant to lepidopteran cotton pests (e.g., resistant to bollworm, tobacco budworm, and armyworm). ".

[0094] Compositions containing compound (I) can be applied to areas where weeds grow or may grow. Examples include methods of spraying the compositions of the invention onto soil and methods of spraying the compositions of the invention onto weeds.

[0095] In some variants, the application rate of the composition containing compound (I) is typically 1 to 10,000 g / 10,000 m³, based on the total amount of the compound of formula (I) or its salts (including those suitable for agricultural use). 2 2 to 5,000g / 10,000m 2 5 to 2,000g / 10,000m 2 1 to 1000g / 10,000m 2 1 to 500g / 10,000m 2 1 to 100g / 10,000m 2 1 to 75g / 10,000m 2 15 to 1000g / 10,000m 2 15 to 100g / 10,000m 2 15 to 75g / 10,000m 2 Or 15 to 60g / 10,000m 2.

[0096] In one variant, the application rate of the composition of the present invention is typically 1 to 10,000 g / 10,000 m³, based on the total amount of the compound of formula (I) and at least one compound selected from the group consisting of herbicide compounds B and safener group C. 2 2 to 5,000g / 10,000m 2 5 to 2,000g / 10,000m 2 1 to 1000g / 10,000m 2 1 to 500g / 10,000m 2 1 to 100g / 10,000m 2 1 to 75g / 10,000m 2 15 to 1000g / 10,000m 2 15 to 100g / 10,000m 2 15 to 75g / 10,000m 2 Or 15 to 60g / 10,000m 2 .

[0097] In the method of the present invention, an adjuvant may be mixed into the composition of the present invention and then administered. There are no particular limitations on the type of adjuvant, and examples of adjuvants include oil-based adjuvants, such as... And methylated seed oil (MSO); nonionic (esters or ethers of polyoxyethylene), such as Induce; anionic (substituted sulfonates), such as Gramine S; cationic (polyoxyethylene amines), such as T 200BM; and organosilicon, such as L77.

[0098] There are no particular limitations on the pH and hardness of the spray liquid prepared when applying the compositions of the present invention, and the pH is generally in the range of 5 to 9, and the hardness is generally in the range of 0 to 500.

[0099] There are no particular limitations on the time period for applying the composition of the present invention, and it is generally in the range of 5:00 AM to 9:00 PM, and the photon flux density is generally 10 to 2,500 μmol / m². 2 / s.

[0100] When the compositions of the present invention are applied to crop fields, they may be applied before, simultaneously with, and / or after sowing crop seeds. That is, the frequency of application of the compositions of the present invention may be once before, simultaneously with, or after sowing crop seeds; twice before sowing; simultaneously with sowing; or after sowing; or three times at all times.

[0101] When the composition of the present invention is applied before sowing crop seeds, it is applied from 50 days to just before sowing, preferably from 30 days to just before sowing, more preferably from 20 days to just before sowing, and even more preferably from 10 days to just before sowing.

[0102] When the composition of the present invention is applied after sowing crop seeds, it is typically applied immediately after sowing until before flowering. More preferably, the composition is applied immediately after sowing until before emergence, or at the 1- to 6-leaf stage of the crop. Simultaneous application of the composition of the present invention with sowing crop seeds occurs when the seeder and sprayer are integrated.

[0103] In the step of applying the composition of the present invention to the cultivation area, the compound of formula (I) or the compound and at least one other compound selected from the group consisting of herbicide compounds B and safener group C are typically mixed with a carrier (such as a solid or liquid carrier), and adjuvants (such as surfactants) for formulation are added as needed to prepare the formulation. Preferred formulation types are aqueous liquid suspensions, oil-based suspensions, wettable powders, water-dispersible particles, granules, water-based emulsions, oil-based emulsions, and emulsifiable concentrates, with emulsifiable concentrates being a more preferred type. Furthermore, formulations containing a single compound of formula I as an active ingredient and formulations containing at least one compound selected from the group consisting of herbicide compounds B and safener group C as active ingredients can be used in combination. Additionally, formulations containing the composition of the present invention as an active ingredient and formulations containing another herbicide as an active ingredient can be used in combination.

[0104] Examples of methods for applying the compositions of the invention in a cultivation area include spraying them onto the soil in the cultivation area and spraying the compositions of the invention onto growing weeds. The compositions are typically diluted with water and then sprayed. The spray volume is not particularly limited and is typically 50 to 1,000 L / ha, preferably 100 to 500 L / ha, and more preferably 140 to 300 L / ha.

[0105] Specific examples of weed species controlled by the compositions of the present invention include, but are not limited to, the weed species described below.

[0106] The Urticaceae weeds to be controlled include European nettle (Urtica urens).

[0107] The Polygonaceae weeds to be controlled include Polygonum convol vulus, Polygonum lapathifolium, Polygonum pens ylvanicum, Polygonum umpersicaria, Polygonum longiset um, Polygonum aviculare, Polygonum arenastrum, Polygonum cuspidatum, Rumex japonicus, Rumex crispus, Rumex obtusifolius, and Rumex acetosa.

[0108] The Portulacaceae weeds to be controlled include purslane (Portulaca oleracea).

[0109] The Caryophyllaceae weeds to be controlled include Stellaria media, Stellaria aquatica, Celestium holosteoides, Celestium glomeratum, Spergula arvensis, and Silene gallica.

[0110] The weeds to be controlled in the Molluginaceae family include Mollugoverticillate.

[0111] The Chenopodiaceae weeds to be controlled include Chenopodium album, Chenopodium ambrosioides, Kochia scoparia, Salsola kali, and species of the genus Atriplex spp.

[0112] The Amaranthaceae weeds to be controlled include *Amaranthus retro flexus*, *Amaranthus viridis*, *Amaranthus lividus*, *Amaranthus spinosus*, *Amaranthus hybridus*, *Am aranthus palmeri*, *Amaranthus patulus*, *Amaranthus tuberculatus*, *Amaranthus rudis*, or *Amaranthus ta mariscinus*, *Amaranthus blitoides*, *Amaranthus defl exus*, *Amaranthus quitensis*, and *Alternantheraphila*. oxeroides, lotus seed grass (Alternanthera sessilis), and tender amaranth (Alternanthera tenella).

[0113] The poppy family (Papaveraceae) weeds to be controlled include Papaver rhoeas, Papaver dubium, and Argemone Mexicana.

[0114] The cruciferous weeds to be controlled include wild radish (Raphanus raph anistrum), radish (Raphanus sativus), wild mustard (Sinapis arvensis), sand ginseng (Capsella bursa-pastoris), mustard (Brassica juncea), rapeseed (Brassica napus), descurainia pinnata, water sedge (Rorippa islandica), European watercress (Rorippa sylvestris), thlaspiarvense, wrinkled shepherd's purse (Myagrum rugosum), American shepherd's purse (Lepidium virginicum), and stinking shepherd's purse (Coronopus didy mus).

[0115] The Capparaceae weeds to be controlled include related species of the genus Cleome affinis.

[0116] The legume weeds to be controlled include Aeschynomene indica, Aeschynomenerudis, Sesbania exaltata, Cassia obtus ifolia, Cassiaoccidentalis, Desmodium tortuos um, Desmodium adscendens, Desmodium illi noense, Trifolium repens, Pueraria lobata, Vicia angustifolia, Indigofera hirsuta, Indigofera truxi llensis, and Vigna sinensis.

[0117] The Oxalidaceae weeds to be controlled include Oxalis corniculata, Oxalis strica, and Oxalis oxyptera.

[0118] The Geraniaceae weeds to be controlled include Geranium carolinense and Erodium cicutarium.

[0119] The Euphorbiaceae weeds to be controlled include Euphorbia heliosc opia, Euphorbia maculata, Euphorbia humistrata, Euphorbia esula, Euphorbia heterophylla, Euphorbia brasiliensis, Acalypha australis, Croton on glandulosus, Croton lobatus, Phyllanthus corcovadensis, and Ricinus communis.

[0120] The Malvaceae weeds to be controlled include Abutilon theophrasti, Sida rhombiforia, Sida cordifolia, Sida spinosa, Sida glaziovii, Sida santaremnensis, Hibiscus trionum, Anoda cristata, and Mal vastrum coromandelianum.

[0121] The Onagraceae weeds to be controlled include Ludwigia epilobioides, Ludwigia octovalvis, Ludwigia decurre, Oenothera biennis, and Oenothera laciniata.

[0122] Weeds in the Sterculiaceae family that need to be controlled include Waltheria indica.

[0123] The Violaceae weeds to be controlled include wild violet (Viola arvensis) and pansy (Viola tricolor).

[0124] The Cucurbitaceae weeds to be controlled include Sicyos angulatu s., Echinocystis lobata and Momordica charantia.

[0125] The Lythraceae weeds to be controlled include Ammannia mu ltiflora, Ammannia auriculata, Ammannia coccinea, Lythrum salicaria, and Rotala indica.

[0126] The Elatinaceae weeds to be controlled include Elatine triandra and Elatine californica.

[0127] The Apiaceae weeds to be controlled include wild celery (Oenanthe javanica), wild carrot (Daucus carota), and poisonous sea cucumber (Conium maculatum).

[0128] The Ceratophyllaceae weeds to be controlled include Ceratophyllum lumdemersum.

[0129] The Cabombaceae weeds to be controlled include water shield grass (Cabomba caroli niana).

[0130] The Haloragaceae weeds to be controlled include Myriop hyllumaquaticum, Myriophyllum verticillatum, Myriophyllum spicatum, and Myriophyllum heterophyllum.

[0131] Weeds to be controlled in the Sapindaceae family include Cardiospermum halicacabum.

[0132] The Primulaceae weeds to be controlled include Anagallis arvensis.

[0133] The weeds in the Asclepiadaceae subfamily that need to be controlled include Syrian milkweed (Ascle piassyriaca) and Ampelamus albidus.

[0134] The Rubiaceae weeds to be controlled include Galium aparine, Galium spurium var. echinospermon, Spermacocelatifolia, Richardia brasiliensis, and Borrelia alata.

[0135] The Convolvulaceae weeds to be controlled include: *Ipomoea nil*, *Ipomoea hederacea*, *Ipomoea purpurea*, *Ipomoea hederacea var. integriuscula*, *Ipomoea lacunosa*, *Ipomoea triloba*, *Ipomoea acuminata*, *Ipomoea hederifolia*, *Ipomoea coccinea*, *Ipomoea quamoclit*, *Ipomoea grandifolia*, *Ipomoea aristolochiafolia*, *Ipomoea cairica*, *Convolvulus arvensis*, *Calystegia hederacea*, and *Calystegia japonica*. The species include *Japonica*, *Merremia hedeacea*, *Merremia aegyptia*, *Merremia cissoides*, and *Jacquemontia tamnifolia*.

[0136] The Boraginaceae weeds to be controlled include wild forget-me-not (Myosotis arve nsis).

[0137] The Lamiaceae weeds to be controlled include *Lamium purpureum*, *Lamium amplexicaule*, *Leonotis nepetaefolia*, *Hyptis suaveolens*, *Hyptis lophanta*, *Leonurus sib iricus*, and *Stachys arvensis*.

[0138] The Solanaceae weeds to be controlled include Datura stramonium, Solanum nigrum, Solanum americanum, Solanum ptycanthum, Solanum sarrachoides, Solanum rostratum, Solanumaculeatissimum, Solanum sisymbriifolium, Solanum carolinense, Physalis angulata, Physalis subglabrata, and Nicandra physaloides.

[0139] The Scrophulariaceae weeds to be controlled include Veronica hederaefolia, Veronica persica, Veronica arvensis, Lindernia procumbens, Lindernia dubia, Lindernia angustifolia, Bacopa rotundifolia, Dopatrium junceum, and Gratiola japonica.

[0140] The plantaginaceae weeds to be controlled include Plantago asiatica, Plantago lanceolata, Plantago major, and Callitrichepalustris.

[0141] The Asteraceae weeds to be controlled include Pennsylvania cocklebur (Xanthium pensylva nicum), Western cocklebur (Xanthium occidentale), Italian cocklebur (Xanthium italicum), wild sunflower (Helianthus annuus), German chamomile (Matricaria cham omilla), flavorless chamomile (Matricaria perforata), southern garland chrysanthemum (Chrysanthemum seg etum), same-flowered chamomile (Matricaria matricarioides), sagebrush (Artemisia princeps), northern wormwood (Artemisia vulgaris), southern wormwood (Artemisia verlotorum), American goldenrod (Solidago altissima), western dandelion (Taraxacum officinale), coarse-haired hyssop (Galinsoga ciliata), hyssop (Galinsoga parviflora), European senecio vulgaris, and Brazilian senecio (Senecio vulgaris). brasiliensis, Senecio gris ebachii, Conyza bonariensis, Conyza smatrensis, Conyza canadensis, Ambrosia artemisiaefolia, Amb rosia trifida, Bidens tripartita, Bidens pilosa, Bidens frondosa, Bidens subalternans, Cirsium arvens e, Cirsium vulgare, Silybummarianum, Carduus nutans, Lactuca serriola, Sonchus oleraceus, Sonchus asper, Wedelia glauca, Melampodium perfoliatum, Emilia sonchifolia, Tagetesminuta, Blainvillea latifolia, Tridax procunetummbens), Porophyllum ruderale, Acanthospermum au strale, Acanthospermum hispidum, Cardiosperm um halicacabum, Ageratum conyzoides, Eupatori um perfoliatum, Eclipta alba, Erechtites hieracifolia, Gamochaeta spicata, Gnaphalium spicatum, Jaeger ia hirta, Parthenium hysterophorus, Siegesbeckia orien talis, Soliva sessilis, Eclipta prostrata, Eclipta alba, and Centipeda minima.

[0142] The Alismataceae weeds to be controlled include Sagittaria pygmaea, Sagittaria trifolia, Sagittaria sagittifolia, Sagittaria montevidensis, Sagittaria aginashi, Alismata canaliculatum, and Alismata plantago-aquatica.

[0143] The Limnocharitaceae weeds to be controlled include Limnocharisflava.

[0144] The Hydrocharitaceae weeds to be controlled include Limnobium spongia, Hydrilla verticillata, and Najas guadalupensis.

[0145] The Araceae weeds to be controlled include Pistia stratiotes.

[0146] The Lemnaceae weeds to be controlled include Lemna aoukikusa, Spirodelapolyrhiza, and species of the genus Wolffia spp.

[0147] The Potamogetonaceae family to be controlled includes Potamogeton distinctus, Potamogeton crispus, Potamogeton illinoensis, and Stuckenia pectinata.

[0148] The Liliaceae weeds to be controlled include Canadian garlic (Allium canadens e), wild onion (Allium vineale), and wild garlic (Allium macrostemon).

[0149] The Pontederiaceae weeds to be controlled include water hyacinth (Eichhornia crassipes), marshland heterosperm (Heteranthera limosa), rain hyacinth (Monochoria korsakowii), and duck tongue grass (Monochoria vaginalis).

[0150] The Commelinaceae weeds to be controlled include Commelina communis, Commelina bengharensis, Commelina erecta, and Murdanniakeisak.

[0151] The Poaceae weeds to be controlled include barnyard grass (Echinochloa crus-galli), rice barnyard grass (Echinochloa oryzicola), wild barnyard grass (Echinochloa crus-galli var. formosensis), paddy field barnyard grass (Echinochloa oryzoides), bald barnyard grass (Echinochloa colona), peacock barnyard grass (Echinochloa crus-pavonis), foxtail grass (Setaria viridis), large foxtail grass (Setaria faberi), golden foxtail grass (Setaria glauca), purslane foxtail grass (Setaria geni culata), climbing crabgrass (Digitaria ciliaris), crabgrass (Digitaria sanguinalis), horizontal crabgrass (Digitaria horizontalis), two-ear grass (Digitaria inularis), goosegrass (Eleusine indica), and annual bluegrass (Poa annua). annua), common Kentucky bluegrass (Poatrivialis), Kentucky bluegrass (Poa pratensis), wild oat (Alospecurus aequalis), large-spike wild oat (Alopecurus myosuroides), wild oat (Avena fatua), rock grass (Sorghum halepe nse), sorghum (Sorghum vulgare), creeping icegrass (Agropyron repens), multiflora ryegrass (Lolium multiflorum), perennial ryegrass (Lolium perenne), rigid ryegrass (Lolium rigidum), flat bromegrass (Bromus catharticus), sterile bromegrass (Bromus sterilis), bromegrass (Bromus japonicus), ryegrass-like bromegrass (Bromus secalinus), silky bromegrass (Bromus tectorum), awned barley grass (Hordeum jubatum), cylindrical goatgrass (Aegilops cylindrica), pheasantgrass (Phalaris) arundinacea, Phalari s minor, Apera spica-venti, Panicum dichotomifl orum, Panicum texanum, Panicum maximum, Brachiariaplatyphylla, Brachiaria ruziziensi s, Brachiaria plantaginea, Brachiaria decumbens, Brachiaria brizantha, Brachiaria hu midicola, Cenchrus echinatus, Cenchrus paucif lorus, Eriochloa villosa, Pennisetum setosum, Chlorisgayana, Chlorisvirgata, Eragrosti s pilosa, Rhynchelitrum repens, Dactyloctenium aegyptium, Ischaemumrugosum, Isachne globosa, Oryza *Paspalum sativa*, *Paspalum notatum*, *Paspalum maritimum*, *Paspalum distichum*, *Pennisetum clandestinum*, *Pennisetum setosum*, *Rottboel liacochinchinensis*, *Leptochloa chinensis*, *Leptochloa fascicularis*, *Leptochloa filiformis*, *Leptochloapanicoides*, *Leersia japonica*, *Leersia sayanuka*, *Leersia oryzoides*, *Glyceria leptorrhiza*, *Glyceria acutiflora*, *Glyceria maxima*, *Agrosti s...* gigantea, Agrostisstolonifera, Cynodon dactylon, Dactylis glomerata, Eremochloa ophiuroides, FestucaThe species include *Arundinacea*, *Festuca rubra*, *Imperata cylindrica*, *Miscanthus sinensis*, *Panicum virgatum*, and *Zoysia*.

[0152] The Cyperaceae weeds to be controlled include *Cyperus mi croiria*, *Cyperus iria*, *Cyperus compressus*, *Cyperus difformis*, *Cyperus flaccidus*, *Cyperus globosus*, *Cyperus nipponics*, *Cyperus od oratus*, *Cyperus serotinus*, *Cyperus rotundus*, *Cyperus esculentus*, *Kyllingagracillima*, *Kyllinga brevifolia*, *Fimbristylis miliacea*, *Fim bristylis dichotoma*, and *Eleocharis*. acicularis), Eleoch aris kuroguwai, Schoenoplectiella hotarui, Schoenoplectiella juncoides, Schoenoplectiella wallichii, Schoenoplectiella mucronatus, Schoenoplectiella triangulatus, Schoenoplectiella nipponicus, Schoenoplectiella triqu eter, Bolboschoenus koshevnikovii, and Bolboschoenus fluviatilis.

[0153] The Equisetaceae weeds to be controlled include Equisetum arvense and Equisetum palustre.

[0154] The Salviniaceae weeds to be controlled include Salvinia natans.

[0155] The Azollaceae weeds to be controlled include Japanese Azolla (Azolla japo nica) and Azolla imbricata.

[0156] The Marsileaceae weeds to be controlled include Marsilea quadrifolia.

[0157] Other weeds to be controlled include *Pithophora*, *Cladophora*, *Bryophyta*, *Marchantiophyta*, *Anthoc erotophyta*, cyanobacteria, ferns, and haustoria of perennial crops (pomelos, nuts, citrus fruits, hops (Humulus lupulus), grapes, etc.).

[0158] In the aforementioned weeds to be controlled, intraspecific mutations are not particularly limited. That is, weeds include those with reduced sensitivity to a particular herbicide. Reduced sensitivity can be attributed to mutations at the target site (target site mutation) or to any factor other than the target site mutation (non-target site mutation). Examples of factors causing reduced sensitivity due to non-target site mutations include increased metabolism, malabsorption, translocation dysfunction, and excretion outside the system. Examples of factors increasing metabolism include enhanced activity of metabolic enzymes such as cytochrome P450 monooxygenases, arylamidinases, esterases, or glutathione S-transferases. Examples of excretion outside the system include transport to vacuoles via ABC transporters. Examples of weeds with reduced sensitivity due to target site mutations include weeds with one or more of the following amino acid substitutions in the ALS gene: Ala122Thr, Ala122Val, Ala122Tyr, Pro197Ser, Pro197His, Pro197Thr, Pro197Arg, Pro197Leu, Pro197Gln, Pro197Ala, Pro197Ile, Ala205Val, Ala205Phe, Asp376Glu, Arg377His, Trp574Leu, Trp574Gly, Trp574Met, Ser653Thr, Ser653Thr, Ser653Asn, Ser635Ile, Gly654Glu, and Gly645Asp. Similarly, examples of weeds with reduced sensitivity due to target site mutations include weeds with one or more of the following amino acid substitutions in the ACCase gene: Ile1781Leu, Ile1781Val, Ile1781Thr, Trp1999Cys, Trp1999Leu, Ala2004Val, Trp2027Cys, Ile2041Asn, Ile2041Val, Asp2078Gly, Cys2088Arg, Gly2096Ala, and Gly2096Ser.

[0159] Similarly, as an example of a weed with reduced sensitivity due to target site mutations, PPO inhibitor-resistant weeds have one or more mutations selected from Arg128Leu, Arg128Met, Arg128Gly, Arg128His, Gly210 deletion, and Gly399Ala in PPO. The word "PPO" refers to protoporphyrinogen oxidase. Weeds typically have PPO1 and PPO2 in PPO, and the aforementioned mutations can be present in PPO1 or PPO2, or both. The presence of a PPO2 mutation in the weed is preferred. For example, the word "Arg128Met" indicates a mutation present at amino acid 128 (this number is normalized using PPO2 in Amaranthus longifolia). In ragweed PPO2, the mutation corresponds to a mutation at amino acid 98 (Rousonelos et al., Weed Science (2012) Vol. 60, pp. 335-344), and is known as Arg98Leu. In this case, according to the invention, Arg98 is equivalent to Arg128. The Arg128Met and Arg128Gly mutations in the PPO of the weeds to be controlled in this invention are known in Amaranthus longicornis (Giacomini et al., Pest Management Science (2017) Vol. 73, pp. 1559-1563), the Arg128His mutation is known in Straight Ryegrass (Fernandez-Moreno et al., Weed Science Society of America (WSSA) annual meeting, 2018), and the Gly399Ala mutation is known in Amaranthus longicornis (Rangani et al., WSSA annual meeting, 2018). In this invention, the aforementioned resistant weeds are particularly effectively controlled, but the weeds that are particularly effectively controlled are not limited to these. That is, other weeds with amino acid mutations are also similarly controlled. Not only is long-awned amaranth with Arg128Leu mutation, Arg128Met mutation, Arg128Gly mutation, Arg128His mutation, Gly210 deletion mutation, or Gly399Ala mutation effectively controlled, for example, water hemp with the aforementioned mutations, ragweed with the aforementioned mutations, stiff ryegrass with the aforementioned mutations, multiflora ryegrass with the aforementioned mutations, and white-bracted gorgon grass with the aforementioned mutations.

[0160] Similarly, weeds with reduced susceptibility due to target site mutations include those with amino acid substitutions in the EPSP gene such as Thr102Ile, Pro106Ser, Pro106Ala, or Pro106Leu. In particular, they are effectively controlled in weeds resistant to glyphosate and possessing one or both of these mutations, such as goosegrass, ryegrass, stiff ryegrass, sedge, water hemp, and barnyard grass. Similarly, weeds with reduced susceptibility due to target sites include those with increased copies of the EPSP gene, and are particularly effective in controlling glyphosate-resistant and mutated weeds such as long awned amaranth, water hemp, and kochia. They are also effectively controlled in weeds resistant to glyphosate involving the ABC transporter, such as smatrensis, conyza, and sage.

[0161] In the cultivation of crops according to the present invention, plant nutrient management as in general crop cultivation can be performed. The fertilization system can be based on precision agriculture or can be a conventional uniform fertilization system. Additionally, nitrogen-fixing bacteria or mycorrhizal fungi can be inoculated in combination with seed treatment.

[0162] Preparation of compound (I)

[0163] In a general example, the compound of formula (I) can be prepared as shown in scheme 1a.

[0164]

[0165] Therefore, compound c can be prepared by reacting compound (a) (where X is Br or I) with a substituted phenyl group of formula (b) under cross-coupling reaction conditions with the aid of a metal catalyst as shown in step 1 of scheme 1a. Suitable catalysts include palladium catalysts, such as Pd(OAc)2 in combination with 2-dicyclohexylphosphino-2',6'-dimethoxybiphenyl (SPhos). As shown in step 2 of scheme 1a, compound (d) can be prepared by demethylating the aryl methyl ether of compound (c) under acidic conditions. In one example, a Lewis acid, such as boron tribromide, can be used. As shown in step 3 of scheme 1a, compound (e) can be prepared by reducing the nitro group of compound (d). Several methods for this are known to those skilled in the art, including the use of catalytic hydrogenation, sodium sulfide, or sodium hyposulfite. As shown in step 4 of scheme 1a, compound (g) can be prepared by condensing the amino group of compound (e) with a suitable haloacetic acid ester of formula (f) under alkaline conditions in an organic solvent. In one example, the base is a trialkylamine, such as triethylamine or diisopropylethylamine. As shown in step 5 of scheme 1a, the benzoxazinone of formula (h) (a compound of formula (I), wherein R...) 1Compound (I) can be prepared in a suitable polar organic solvent (such as DMF or DMSO) via an intramolecular ring closure between the phenolic hydroxyl group and the N-acyl halide of compound (g). As shown in step 6 of scheme 1a, compound (I) (where R) 1 For example, the C that can be arbitrarily substituted. 1-4 Alkyl groups can be formed by reacting the benzoxazinone amino group of compound (h) with an alkyl or aryl halide of compound (i) under suitable bonding conditions. Alternatively, compound (h) can be formed by a Chan-Lam type coupling reaction with boric acid of compound (j) to form compound (I).

[0166] In another general example, the compound of formula (I) can be prepared as shown in scheme 1b.

[0167]

[0168] Therefore, the phenylboronic acid (where R = H) or phenylboronic ester (e.g., where B(OR)2 represents pinacol ester) of formula (j) can be coupled with a suitably substituted phenyl bromide or iodide using a suitable catalyst in a Suzuki-Miyaura type reaction to produce compound (c) (step 1). This can also be achieved under similar conditions by reacting compound (k) with compound (m) (step 2). Compound (c) can then be converted to compound (I) using steps similar to steps 2 to 6 described in scheme 1a. Alternatively, compound (n) can be reacted with compound (o) (step 3) or compound (p) can be reacted with compound (q) under Suzuki conditions (step 4) to produce compound (I).

[0169] preparation

[0170] In some respects, at least a portion of the compositions disclosed herein, or of the compositions described herein (including those comprising agriculturally suitable salts), may include at least one additional component selected from the group consisting of surfactants, solid diluents, and liquid diluents, which serves as a carrier. The formulation components are selected to be consistent with the physical properties of the active ingredient, the method of application, and environmental factors such as soil type, moisture, and temperature.

[0171] Liquid formulations include solutions (including emulsifiable concentrates), suspensions, emulsions (including microemulsions, oil-in-water emulsions, flowable concentrates, and / or suspension emulsions), which may optionally be thickened into gels. Common types of aqueous liquid formulations include soluble concentrates, suspension concentrates, capsule suspensions, concentrated emulsions, microemulsions, oil-in-water emulsions, flowable concentrates, and suspension emulsions. Common types of non-aqueous liquid formulations include emulsifiable concentrates, microemulsion concentrates, dispersible concentrates, and oil dispersions.

[0172] Solid dosage forms are generally available in the form of dust, powder, granules, pellets, pellets, lozenges, tablets, and filler films (including seed coatings), and can be water-dispersible (“wettable”) or water-soluble. Films and coatings formed from film-forming solutions or flowable suspensions are particularly suitable for seed treatment. Active ingredients can be (micro)encapsulated and further formed into suspensions or solid dosage forms. Alternatively, the entire formulation of the active ingredient can be encapsulated (or “coated”). Encapsulation can control or delay the release of the active ingredient. Emulsifiable granules combine the advantages of emulsifiable concentrate formulations and dry granule formulations. High-strength formulations are primarily used as intermediates for further formulation.

[0173] Sprayable formulations are typically prepared in a suitable medium before spraying. These liquid and solid formulations are formulated to be easily diluted in a spraying medium, usually water, but occasionally another suitable medium such as aromatic or alkanes or vegetable oils. Spray volumes can range from about one liter to several thousand liters per hectare, but more typically from about ten liters to several hundred liters per hectare. Sprayable formulations can be mixed with water or another suitable medium for foliar application via air or ground application, or for application to the plant's growing medium.

[0174] Liquid and dry formulations can be metered directly into the drip irrigation system or into the furrows during the growing season.

[0175] The formulation typically contains effective amounts of the active ingredient, diluent, and surfactant, within the approximate range shown in Table 2, totaling 100% by weight.

[0176] Table 2. Formulation Ratio

[0177]

[0178] Solid diluents include, for example, clays (such as bentonite, montmorillonite, palygorskite, and kaolin), gypsum, cellulose, titanium dioxide, zinc oxide, starch, dextrin, sugars (e.g., lactose, sucrose), silica, talc, mica, diatomaceous earth, urea, calcium carbonate, sodium carbonate, and bicarbonates, as well as sodium sulfate. Typical solid diluents are described in Watkins et al., Handbook of Insecticide Dust Diluents and Carriers, 2nd ed., Dorland Books, Caldwell, New Jersey.

[0179] Liquid diluents include, for example, water; N,N-dimethylalkanamide (e.g., N,N-dimethylformamide); limonene; dimethyl sulfoxide; N-alkylpyrrolidone (e.g., N-methylpyrrolidone); alkyl phosphates (e.g., triethyl phosphate); ethylene glycol; triethylene glycol; propylene glycol; dipropylene glycol; polypropylene glycol; propylene carbonate; butene carbonate; alkanes (e.g., white mineral oil, n-alkanes, isoalkanes); alkylbenzenes; alkylnaphthalenes; glycerol; triacetylglycerol; sorbitol; aromatic hydrocarbons; dearomatized aliphatic hydrocarbons; alkylbenzenes; alkylnaphthalenes; ketones, such as cyclohexanone, 2-heptanone, isophorone, and 4- Hydroxy-4-methyl-2-pentanone; acetate esters, such as isoamyl acetate, hexyl acetate, heptyl acetate, octyl acetate, nonyl acetate, tridecyl acetate, and isobornyl acetate; other esters, such as alkyl lactates, diesters, alkyl benzoates, aryl benzoates, and γ-butyrolactone; and alcohols, which may be straight-chain, branched, saturated, or unsaturated, such as methanol, ethanol, n-propanol, isopropanol, n-butanol, isobutanol, n-hexanol, 2-ethylhexanol, n-octanol, decanol, isodecanol, isoctadecanol, isooctadecanol, hexadecyl alcohol, lauryl alcohol, tridecyl alcohol, oleyl alcohol, cyclohexanol, tetrahydrofurfuryl alcohol, diacetone alcohol, cresol, and benzyl alcohol. Liquid diluents also include saturated and unsaturated fatty acids (typically C6-C). 22 Triglycerides of plant seeds and fruits (e.g., olive oil, castor oil, flaxseed oil, sesame oil, corn oil, peanut oil, sunflower oil, grapeseed oil, safflower oil, cottonseed oil, soybean oil, rapeseed oil, coconut oil, and palm kernel oil), animal fats (e.g., beef tallow, lard, cod liver oil, fish oil), and mixtures thereof. Liquid diluents also include alkylated fatty acids (e.g., methylated, ethylated, butylated), wherein the fatty acids can be obtained by hydrolyzing glycerides from plant and animal sources and can be purified by distillation. Typical liquid diluents are described in C. Marsden & S. Mann, Solvents Guide, Cleaver-Hume Press, London, 1963.

[0180] Surfactants can be classified as nonionic, anionic, or cationic. Nonionic surfactants that can be used in the formulations of this invention include, but are not limited to: alcohol alkoxylates, such as alcohol alkoxylates based on natural and synthetic alcohols (which may be branched or linear) and prepared from alcohols and ethylene oxide, propylene oxide, butyl oxide, or mixtures thereof; amine ethoxylates, alkanolamides, and ethoxylated alkanolamides; alkoxylated triglycerides, such as ethoxylated soybean oil, castor oil, and rapeseed oil; alkylphenol alkoxylates, such as octylphenol ethoxylates, nonylphenol ethoxylates, dinonylphenol ethoxylates, and dodecylphenol ethoxylates (prepared from phenols and ethylene oxide, propylene oxide, butyl oxide, or mixtures thereof); block polymers prepared from ethylene oxide or propylene oxide and reverse block polymers wherein the terminal blocks are prepared from propylene oxide; ethoxylated esters... Fatty acids; ethoxylated fatty esters and oils; ethoxylated methyl esters; ethoxylated tristyrylphenols (including those prepared from ethylene oxide, propylene oxide, butane oxide, or mixtures thereof); fatty acid esters, glycerides, lanolin-based derivatives, polyethoxylated esters, such as polyethoxylated sorbitol fatty acid esters, polyethoxylated sorbitol fatty acid esters, and polyethoxylated glycerol fatty acid esters; other sorbitol derivatives, such as sorbitol esters; polymer surfactants, such as random copolymers, block copolymers, alkyd PEG (polyethylene glycol) resins, grafted or comb-like polymers, and star polymers; polyethylene glycol (PEG); polyethylene glycol fatty acid esters; organosilicon-based surfactants; and sugar derivatives, such as sucrose esters, alkyl polyglycosides, and alkyl polysaccharides.

[0181] Useful anionic surfactants include, but are not limited to: alkylaryl sulfonic acids and their salts; carboxylated alcohols or alkylphenol ethoxylates; diphenyl sulfonate derivatives; lignin and lignin derivatives, such as lignin sulfonates; maleic acid or succinic acid or their anhydrides; olefin sulfonates; phosphate esters, such as phosphate esters of alcohol alkoxylates, phosphate esters of alkylphenol alkoxylates and phosphate esters of styrylphenol ethoxylates; protein-based surfactants; sarcosine derivatives; styrylphenol ether sulfates; sulfates and sulfonates of oils and fatty acids; sulfates and sulfonates of ethoxylated alkylphenols; sulfates of alcohols; sulfates of ethoxylated alcohols; sulfonates of amines and amides, such as N,N-alkyl taurate; sulfonates of benzene, cumene, toluene, xylene and dodecyl and tridecylbenzene; sulfonates of condensed naphthalene; sulfonates of naphthalene and alkylnaphthalene; sulfonates of fractionated petroleum; sulfosuccinates; and sulfosuccinates and their derivatives, such as dialkyl sulfosuccinates.

[0182] Useful cationic surfactants include, but are not limited to: amides and ethoxylated amides; amines, such as N-alkylpropylenediamine, tripropylenetriamine and diallyltetraamine, and ethoxylated amines, ethoxylated diamines and propoxylated amines (prepared from amines and ethylene oxide, propylene oxide, butyl oxide or mixtures thereof); amine salts, such as amine acetates and diamine salts; quaternary ammonium salts, such as quaternary salts, ethoxylated quaternary salts and diquaternary salts; and amine oxides, such as alkyl dimethylamine oxides and bis-(2-hydroxyethyl)-alkylamine oxides.

[0183] Also useful to the formulations of the present invention are mixtures of nonionic and anionic surfactants or mixtures of nonionic and cationic surfactants. Nonionic surfactants, anionic surfactants, and cationic surfactants, and their recommended uses, are disclosed in various published references, including McCutcheon's *Emulsifiers and Detergents*, annual American and International Editions published by McCutcheon's Division, The Manufacturing Confectioner Publishing Co.; Sisley and Wood, *Encyclopedia of Surface Active Agents*, Chemical Publ. Co., Inc., New York, 1964; and A.S. Davidson and B. Milwidsky, *Synthetic Detergents*, seventh edition, John Wiley and Sons, New York, 1987.

[0184] The formulations of this invention may also contain formulation adjuvants and additives known to those skilled in the art (some of which may also be considered as solid diluents, liquid diluents, or surfactants). Such formulation adjuvants and additives can control the following: pH (buffers), foaming during processing (defoamers, such as polysiloxanes), sedimentation of active ingredients (suspending agents), viscosity (thixotropic thickeners), microbial growth within the container (antimicrobial agents), product freezing (antifreeze agents), color (dye / pigment dispersions), elution (film-forming agents or adhesives), evaporation (evaporation inhibitors), and other formulation properties. Film-forming agents include, for example, polyvinyl acetate, polyvinyl acetate copolymers, polyvinylpyrrolidone-vinyl acetate copolymers, polyvinyl alcohol, polyvinyl alcohol copolymers, and waxes. Examples of formulation adjuvants and additives are listed in McCutcheon Volume 2: Functional Materials, Annual International and North American Edition, published by McCutcheon's division, The Manufacturing Confectioner Publishing Co., and PCT Publication WO 03 / 024222.

[0185] The compounds and any other active ingredients of this invention are typically incorporated into formulations of this invention by dissolving the active ingredient in a solvent or by milling in a liquid or dry diluent. Solutions (including emulsifiable concentrates) can be prepared by simply mixing the ingredients. If the solvent intended for use as an emulsifiable concentrate in a liquid formulation is water-immiscible, an emulsifier is typically added to emulsify the solvent containing the active substance after dilution with water. Active ingredient slurries with particle sizes up to 2,000 micrometers can be wet-milled using a media mill to obtain particles with an average diameter of less than 3 micrometers. Aqueous slurries can be made into a final suspension concentrate (see, for example, U.S. Patent No. 3,060,084) or further processed by spray drying to form water-dispersible particles. Dry formulations typically require a dry milling process, which produces an average particle size in the range of 2 to 10 micrometers. Dust and powders can be prepared by mixing and typically by milling (such as using a hammer mill or a fluid energy mill). Particles and pellets can be prepared by spraying the active material onto a pre-formed particle carrier or by agglomeration techniques. See “Agglomeration,” Chemical Engineer, December 4, 1967, pp. 147-48; Perry’s Chemical Engineer’s Handbook, 4th edition, McGraw-Hill, New York, 1963, pp. 8-57 ff.; and PCT Publication WO 91 / 13546. Granules may be prepared as described in U.S. Patent No. 4,172,714. Water-dispersible and water-soluble particles may be prepared as taught in U.S. Patent Nos. 4,144,050 and 3,920,442 and German Patent No. 3,246,493. Tablets may be prepared as taught in U.S. Patent Nos. 5,180,587, 5,232,701, and 5,208,030. Films may be prepared as taught in British Patent No. 2,095,558 and U.S. Patent No. 3,299,566.

[0186] For further information on formulation technology, see T.S. Woods, “The Formulator's Toolbox - Product Forms for Modern Agriculture”, Pesticide Chemistry and Bioscience, The Food-Environment Challenge, edited by T. Brooks and TR. Roberts, Proceedings of the 9th International Congress on Pesticide Chemistry, The Royal Society of Chemistry, Cambridge, 1999, pp. 120-133. See also U.S. Patent No. 3,235,361, column 6, line 16 through column 7, line 19, and Examples 10-41; U.S. Patent No. 3,309,192, column 5, line 43 through column 7, line 62, and Examples 8, 12, 15, 39, 41, 52, 53, 58, 132, 138-140, 162-164, 166, 167, and 169-182; U.S. Patent No. 2,891,855, column 3, line 66 through column 5, line 17, and Examples 1-4; Klingman, Weed Control as a Science, John Wiley and Sons, Inc., New York, 1961, pp. 81-96; Hance et al., Weed Control Handbook, 8th Edition, Blackwell Scientific Publications, Oxford, 1989; and Developments in Formulation Technology, PJB. Publications, Richmond, UK, 2000.

[0187] Example

[0188] The subject matter disclosed herein will be better understood by referring to the following embodiments, which are provided as examples of the invention and not as limitations.

[0189] For each herbicide combination, the expected response value (E) of mortality or growth inhibition was determined using the Colby equation E = (X + Y) - (XY) / 100 (Colby, Calculating Synergistic and Antagonistic Responses of Herbicide Combinations. Weeds (1967), Vol. 15, pp. 20-22), where X is the percentage of weed control from compound (I) and Y is the percentage of weed control from the herbicide in group B. When the observed response is greater than E, the combination is synergistic.

[0190] Example 1. Weed control when various weeds are sown and a combination of sulfonylpyrazole-containing herbicides is applied to the soil 7 days before soybean sowing.

[0191] Weeds (long-sprout, water hemp, ragweed, three-lobed ragweed, small tuft of grass, lambsquarters, kochia, barnyard grass, and large foxtail) were sown in plastic pots. On the same day, a mixture of compound (I) and ZIDUA was applied to the soil surface at a spray volume of 200 L / ha. The application rate of compound (I) could be 25 g / ha, 50 g / ha, 100 g / ha, or 200 g / ha, and the application rate of ZIDUA (sulfonylpyrazol 85% water-dispersible granules, manufactured by BASF SE) could be 70 g / ha, 140 g / ha, or 280 g / ha (1 oz / acre, 2 oz / acre, or 4 oz / acre). The weeds were then cultured in a greenhouse, and soybeans were sown 7 days after application. The effects on the weeds and crop damage to soybeans were studied 14 days after soybean sowing. Synergistic effects were observed when the Colby formula was met.

[0192] Example 2. Weed control when weeds are sown and a combination containing pyrimethanil is applied to the soil 7 days before soybean sowing.

[0193] Weeds (Amaranthus longifolius, Hemp, Ragweed, Ragweed trifleae, Erigeron candelilla, Lamb's quarters, Kochia scoparia, Barnyardgrass, and Setaria viridis) and soybeans were sown in plastic pots. On the same day, a mixture of compound (I) and Sharpen was applied to the soil surface at a spray volume of 200 L / ha. The application rate of compound (I) could be 25 g / ha, 50 g / ha, 100 g / ha, or 200 g / ha, and the application rate of Sharpen (29.7% wettable powder of pyrimisulfuron-methyl, manufactured by BASF SE) could be 73 ml / ha (1 fluid ounce / acre). The weeds and soybeans were then grown in a greenhouse, and the effects on the weeds and crop damage to the soybeans were studied 21 days after application. Synergistic effects were observed when the Colby formula was met.

[0194] Example 3. Weed control when weeds and soybeans are sown and a combination containing propyzamide is applied to the soil on the same day as the weeds and soybeans are sown.

[0195] Weeds (Amaranthus longifolius, Hemp, Ragweed, Ragweed trifleae, Erigeron candelilla, Lamb's quarters, Kochia scoparia, Barnyardgrass, and Setaria viridis) and soybeans were sown in plastic pots. On the same day, a mixture of compound (I) and Valor SX was applied to the soil surface at a spray volume of 200 L / ha. The application rate of compound (I) could be 25 g / ha, 50 g / ha, 100 g / ha, or 200 g / ha, and the application rate of Valor SX (51% wettable powder of propyzamide, manufactured by Valent USALLC) could be 140 g / ha (2 fluid ounces / acre). The weeds and soybeans were cultivated in a greenhouse, and the effects on the weeds and crop damage to the soybeans were studied 21 days after application. Synergistic effects were observed when the Colby formula was met.

[0196] Examples 4 to 6

[0197] The tests were conducted in the same manner as in Examples 1 to 3, except that corn or cotton was used instead of soybeans.

[0198] Example 7. Weed control when various combinations of glyphosate-containing herbs are applied to the leaves 21 days after weed sowing.

[0199] Weeds (long-sprout grass, water hemp, ragweed, three-lobed ragweed, small tuft of grass, lambsquarters, kochia, barnyard grass, and large foxtail grass) were sown in plastic pots. The weeds were then cultured in a greenhouse, and 21 days after sowing, a mixture of compound (I) and Roundup was sprayed onto the leaves at a spray volume of 200 L / ha. The application rate of compound (I) could be 25 g / ha, 50 g / ha, 100 g / ha, or 200 g / ha, and the application rate of Roundup WeatherMax (660 g / L glyphosate-potassium salt, manufactured by Monsanto Company) could be 2.338 L / ha (32 fluid ounces / acre). The weeds were further cultured in a greenhouse, and the effects on the weeds were studied at 7 and 14 days after treatment. Synergistic effects were observed when the Colby formula was met.

[0200] Example 8. Weed control when weeds are sown and compound (I) is applied to the soil 7 days before soybean sowing and sulfonylpyrazole application.

[0201] Weeds (long-sprout, water hemp, ragweed, three-lobed ragweed, small tuft of grass, lambsquarters, kochia, barnyard grass, and large foxtail) were sown in plastic pots. On the same day, a spray liquid was prepared such that the compound of formula (I) was applied to the soil surface at a spray volume of 200 L / ha. The application rate could be 25 g / ha, 50 g / ha, 100 g / ha, or 200 g / ha. The weeds were then cultivated in a greenhouse, and soybeans were sown 7 days after application, with a spray liquid of ZIDUA applied at a spray volume of 200 L / ha. The application rate of ZIDUA (sulfonylpyrazol 85% water-dispersible granules, manufactured by BASF SE) could be 70 g / ha, 140 g / ha, or 280 g / ha (1 oz / acre, 2 oz / acre, or 4 oz / acre). Fourteen days after soybean sowing, the effects on weeds and crop damage to soybeans were studied. Synergistic effects were observed when the Colby formula was met.

[0202] Example 9. Weed control when weeds are sown and compound (I) is applied to the soil 7 days before soybean sowing and application of pyrimethanil.

[0203] Weeds (Amaranthus longifolius, Hemp, Ragweed, Ragweed trifleae, Erigeron candelilla, Lamb's quarters, Kochia scoparia, Barnyardgrass, and Setaria viridis) were sown in plastic pots. On the same day, a spray liquid was prepared such that the compound of formula (I) was applied to the soil surface at a spray volume of 200 L / ha. The application rate could be 25 g / ha, 50 g / ha, 100 g / ha, or 200 g / ha. The weeds were then cultivated in a greenhouse, and soybeans were sown 7 days after application, with a spray liquid of Sharpen applied at a spray volume of 200 L / ha. Sharpen (29.7% wettable powder of pyrimisulfuron-methyl, manufactured by BASF SE) could be 73 ml / ha (1 fluid ounce / acre). Fourteen days after soybean sowing, the effects on weeds and crop damage to soybeans were studied. Synergistic effects were observed when the Colby formula was met.

[0204] Example 10. Weed control when weeds are sown and compound (I) is applied to the soil 7 days before soybean sowing and propyzamide application.

[0205] Weeds (long-sprouted amaranth, water hemp, ragweed, three-lobed ragweed, small tuft of grass, lambsquarters, kochia, barnyard grass, and large foxtail grass) were sown in plastic pots. On the same day, a spray liquid was prepared such that the compound of formula (I) was applied to the soil surface at a spray volume of 200 L / ha. The application rate could be 25 g / ha, 50 g / ha, 100 g / ha, or 200 g / ha. The weeds were cultured in a greenhouse, and soybeans were sown 7 days after application, with a spray liquid of Valor SX applied at a volume of 200 L / ha. The application rate of Valor SX (51% wettable powder of propyzamide, manufactured by Valent USALLC) could be 140 g / ha (2 fluid ounces / acre). Fourteen days after soybean sowing, the effects on weeds and crop damage to soybeans were studied. Synergistic effects were observed when the Colby formula was met.

[0206] Examples 11 to 13

[0207] The tests were conducted in the same manner as in Examples 8 to 10, except that RoundupPowerMax (660 g / L glyphosate-potassium salt, manufactured by Monsanto Company) was used in addition to the application of compound (I), so that the application rate of RoundupPowerMax could be 2.338 L / ha (32 fluid ounces / acre, glyphosate-potassium salt 1,543 g / ha).

[0208] Example 14. Weed control when weeds are sown and compound of formula (I) is applied to the soil 7 days before soybean sowing and 14 days before glyphosate application.

[0209] Weeds (long-sprout grass, water hemp, ragweed, three-lobed ragweed, small tuft of grass, lambsquarters, kochia, barnyard grass, and large foxtail grass) were sown in plastic pots. On the same day, a spray of compound (I) was applied to the soil surface at a spray volume of 200 L / ha. Compound (I) can be prepared such that the application rate can be 25 g / ha, 50 g / ha, 100 g / ha, or 200 g / ha. The weeds were then cultivated in a greenhouse, and soybeans were sown 7 days after application. Fourteen days after the initial sowing, a spray of RoundupWeatherMax was applied at a spray volume of 200 L / ha. The application rate of RoundupWeatherMax (660 g / L glyphosate-potassium salt, manufactured by Monsanto Company) can be 2.338 L / ha (32 fluid ounces / acre). The effects on the weeds and crop damage to soybeans were studied 14 days later (28 days after the initial sowing). When the synergistic effect satisfies the Colby formula, a synergistic effect is observed.

[0210] Example 15

[0211] The test was conducted in the same manner as in Example 14, except that RoundupPowerMax (660 g / L glyphosate-potassium salt, manufactured by Monsanto Company) was used in addition to the application of the compound of formula (I), so that the application rate of RoundupPowerMax could be 2.338 L / ha (32 fluid ounces / acre, glyphosate-potassium salt 1,543 g / ha).

[0212] Examples 16 to 23

[0213] The tests were conducted in the same manner as in Examples 8 to 15, except that corn or cotton was used instead of soybeans.

[0214] In the case of using any crop in Examples 1 to 23, the tests were conducted in the same manner as in the examples, except that the crops used in the examples were replaced with crops having the Roundup Ready 2Xtend trait.

[0215] Examples 24 to 46

[0216] In the case of using any crop in Examples 1 to 23, the tests were conducted in the same manner as in the examples, except that the crops used in the examples were replaced by crops with Roundup Ready2Xtend traits and PPO inhibitor tolerance traits through genetic engineering, because exogenous PPO has a lower affinity for PPO inhibitors than the crop's endogenous PPO.

[0217] Examples 47 to 69

[0218] In the case of using any crop in Examples 1 to 23, the tests were conducted in the same manner as in the examples, except that the crops used in the examples were replaced by crops with Roundup Ready2Xtend traits and PPO inhibitor tolerance traits through genetic engineering, because exogenous PPO has a lower affinity for PPO inhibitors than the crop's endogenous PPO.

[0219] Example 70. Field testing of compound 1-glyphosate mixture

[0220] Compound 1 and its mixture with glyphosate were tested at different field locations to evaluate herbicide efficacy for weed control via post-emergence foliar application. All herbicide treatments were applied using a backpack CO2 pressurized sprayer at a volume of 190 L / ha. Application was performed after weeds appeared and reached a size range of 5 to 12 cm. Herbicide treatments included Compound 1 formulated as a 10% emulsion concentrate, glyphosate as a commercial formulation (RoundUp Power Max, Monsanto), or a mixture of Compound 1 and glyphosate product prepared as a “tank-mix” prior to field application. All herbicide field spray solutions included ammonium sulfate and concentrated crop oil adjuvants at final solution concentrations of 2% and 1%, respectively. Different weed species were evaluated at different field locations. For each species, herbicide efficacy for weed control was assessed 2 weeks after application, evaluated as a percentage of dead plants relative to untreated control plots, to indicate weed regrowth. The results reported in Table 1 show that the mixture of ENK-3171 and glyphosate provides a better weed spectrum for controlling glyphosate-resistant biotypes (e.g., AMAPA and AMATU at positions 13 and 15, respectively) and a wider spectrum of species types (e.g., coexisting species AMATU and SETFA at position 15).

[0221] Table 1.

[0222]

[0223]

[0224] Example 71. Field testing of a mixture of compound 1-sulfonylpyrazole

[0225] Compound 1 and its mixture with sulfonylpyrazole were tested at different field locations to assess herbicide efficacy for weed control by soil residual activity. All herbicide treatments were applied using a backpack CO2 pressurized sprayer at a volume of 190 L / ha. Herbicides were applied to bare soils without any vegetation to evaluate the efficacy of different herbicides in inhibiting weed germination and development. Herbicide treatments included Compound 1 formulated as a 10% emulsion concentrate, sulfonylpyrazole (ZIDUASC, BASF) as a commercial formulation, or a mixture of Compound 1 and sulfonylpyrazole products prepared as a “can mix” prior to field application. All herbicide field spray solutions included ammonium sulfate, with a final solution concentration of 2%. Different weed species were evaluated at different field locations. For each species, herbicide efficacy for weed control was assessed 6 weeks after herbicide application, evaluated as a percentage of weed suppression relative to the untreated control plot. The results of field tests reported in Table 2 show that the mixture of ENK-3171 and sulfonylpyrazole provides a better weed spectrum and a significant improvement in weed control, because the mixture of compound 1 and sulfonylpyrazole provides more consistent and robust herbicide efficacy across soil types, improved weed control when different types of weeds coexist in the same field, and more sustained efficacy when applied as a single herbicide.

[0226] Table 2.

[0227]

[0228] Table 2. (Continued)

[0229]

[0230] Example 72. Post-emergence mixture comprising compound 1

[0231] The efficacy of compound 1, alone or in combination with other herbicides, in controlling foliar weeds was tested at several doses. The following commercially available herbicides were used in a tank mixture with a 10% active emulsifiable concentrate formulation of compound 1: glyphosate (Roundup). Bayer), nicosulfuron ( Syngenta), 2,4-D dimethylamine salt ( 64, Nufarm), 2,4-D ester ( LV4, Nufarm), Clash miltiorrhiza TM Nufarm), glufosinate ( BASF).

[0232] Weed seeds were sown in 10”×20” trays and propagated to the transplanting stage, i.e., 1-2 leaves. Each plant was then transplanted into a 7×7×8cm pot and sprayed with the compound when the plant reached the 3-4 true leaf stage (for herbaceous species) or 10-15cm (for broadleaf species). Plants were propagated in a greenhouse with a daytime temperature of 26-28°C, a nighttime temperature of 20-22°C, and a relative humidity of 50%-60%, supplemented with high-pressure sodium grow lights as needed. Three weeks after sowing, plants were sprayed with a test compound solution in a laboratory spraying chamber equipped with 8003 units calibrated to deliver 187L ha at 269kPa. -1 Uniform fan-shaped nozzles. All treatments include the following inert components in the final formulation: 1% crop oil concentrate (v / v) Helena Agri), 2.5% ammonium sulfate (w / v) and 0.1% Tween-20 (v / v). At 14 days post-treatment (DAT), the percentage of visual growth inhibition in plants was assessed compared with the treated control.

[0233] The post-emergence herbicidal activity of Compound 1 and other herbicides, either in tank mixtures or as a single application, against AMATU (western amaranth) and ECHCG (wild barnyard grass) is shown in Tables 3.1 and 3.2.

[0234] Table 3.1. Percentage of post-emergence weed growth inhibition by Compound 1 when mixed with other herbicides

[0235]

[0236]

[0237] Table 3.2. Percentage of post-emergence weed growth inhibition by Compound 1 when mixed with other herbicides

[0238]

[0239]

[0240] Example 73. Pre-emergence mixture comprising compound 1

[0241] The residual weed control efficacy of Compound 1, alone or in combination with commercially available herbicides, was tested at several doses. The following commercially available products were used in a can mixture with a 10% active emulsifiable concentrate formulation of Compound 1: Dual-methyl (Dual-methyl)

[0242] Syngenta, nicosulfuron ( Syngenta), Sulfonazole ( SC, BASF), Tricor DF TM United Phosphorus, Inc.

[0243] Therefore, weed seeds were planted in 2-inch pots containing a custom field soil mixture (sandy loam containing 3.3% organic matter, pH 7.0) and covered with a fine layer of the same soil. Three replicate pots were used for each compound treatment. Treatments consisting of the above formulations excluding the active compound served as treatment controls (TC). Pots were prepared with 8003 calibrated for delivery at 269 kPa at 187–200 L / min. -1 Pots were treated with a solution of the test compound in a laboratory spray chamber using a uniform fan-shaped nozzle. All treatments included the following inert components in the final formulation: 1% crop oil concentrate (v / v) (AGRI-DEX, Helena Agri) and 2.5% ammonium sulfate (w / v). Compound 1 was incorporated into the soil using the same tracked sprayer to simulate a rainfall equivalent to 0.2 mm. Pots were then irrigated from the bottom until weed control was assessed. The pots were returned to the greenhouse, and the percentage of visual growth and germination inhibition was assessed compared to TC at 17–21 days post-treatment (DAT). Complete growth inhibition is expressed as 100%.

[0244] Table 4. Percentage of pre-emergence weed growth and germination inhibition of Compound 1 when mixed with other herbicides.

[0245]

Claims

1. A herbicidal composition comprising a compound of formula (I): Or its salt, wherein: R 1 Is H or optionally R 1a C substituted with phenyl or benzyl 1-4 Alkyl group, wherein each of the alkyl, phenyl, or benzyl groups is optionally surrounded by at most three F atoms, one OH group, or one OC group. 1-4 Alkyl group substitution; R 1a yes Each R 1b H and C independently 1-4 Alkyl or cyclopropyl; R 2 and R 3 Each of them independently is H, Cl, F, CH3, or R. 2 and R 3 Together with the carbon in the middle, it is cyclopropyl; R 4 It is H, Cl, or F; R 5 It is H or F; R 6 and R 7 Each is independently F, H, or C that is optionally replaced by OH. 1-2 Alkyl, alkenyl, OH, OC 1-2 Alkyl, O-cyclopropyl, OCH2CCH, NHCH2Ph, N(R) x )2 or SCH3; R 8 It is H or F; Each R x It is independently H, CH3, or C(O)CH3; and Ring A contains at least four F-atom substituents. And at least one second herbicide selected from glyphosate, sulfonylpyrazole, mesotrione, glufosinate, dicamba, 2,4-D acid, 2,4-D ester, metolachlor, and S-metolachlor. The weight ratio of the compound of formula (I) to the second herbicide is about 1:0.1 to 1:

50.

2. The herbicidal composition according to claim 1, wherein the compound of formula (I) is compound 1:

3. The herbicidal composition according to claim 2, wherein the second herbicide is glyphosate and the weight ratio of compound 1 to glyphosate is about 30:60 to 1000:1120.

4. The herbicidal composition according to claim 2, wherein the second herbicide is sulfonylpyrazole, and the weight ratio of compound 1 to sulfonylpyrazole is about 15:60 to 90.

5. The herbicidal composition according to claim 2, wherein the second herbicide is nicosulfuron, and the weight ratio of compound 1 to nicosulfuron is about 30:60 to 105:

210.

6. The herbicidal composition according to claim 2, wherein the second herbicide is glufosinate, and the weight ratio of compound 1 to glufosinate is about 30:60 to 450.

7. The herbicidal composition according to claim 2, wherein the second herbicide is dicamba, and the weight ratio of compound 1 to dicamba is about 30:60 to 280.

8. The herbicidal composition according to claim 2, wherein the second herbicide is 2,4-D acid, and the weight ratio of compound 1 to 2,4-D acid is from about 30:60 to 280.

9. The herbicidal composition according to claim 2, wherein the second herbicide is a 2,4-D ester, and the weight ratio of compound 1 to the 2,4-D ester is from about 30:60 to 280.

10. The herbicidal composition according to claim 2, wherein the second herbicide is metribuzin, and the weight ratio of compound 1 to metribuzin is about 30 to 210.

11. The herbicidal composition according to claim 2, wherein the second herbicide is metolachlor, and the weight ratio of compound 1 to metolachlor is about 30 to 1000.

12. A method for controlling unwanted vegetation, the method comprising contacting the vegetation or its environment with a herbicidal amount of the composition according to any one of claims 1 to 11.

13. The method of claim 12, wherein the undesirable vegetation comprises weeds.

14. The method of claim 12, wherein the undesirable vegetation comprises protoporphyrinogen IX oxidase (PPO) inhibitor-resistant weeds.

15. The method of claim 14, wherein the PPO inhibitor-resistant weed has the dG210 mutation.

16. The method of claim 12, wherein contacting the undesirable vegetation or its environment with the compound or composition results in post-emergence control of the undesirable vegetation.

17. The method of claim 12, wherein contacting the undesirable vegetation or its environment with the compound or composition results in pre-emergence control of the undesirable vegetation.

18. The method of claim 12, wherein the undesirable vegetation is at least 60% controlled.

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