Herbicide composition

Abstract

The present invention provides (A) a herbicidally effective amount of a compound of formula (I): [Formula 1] The present invention relates to a herbicide composition comprising the compound of formula (I) JPEG2026507058000029.jpg43161 or an agrochemically acceptable ester or salt thereof, and (B) glufosinate or L-glufosinate.

Description

[Technical Field]

[0001] The present invention relates to novel herbicidal compositions comprising a combination of herbicidal active ingredients that provide weed control in crops of useful plants. The present invention further provides a method for controlling weeds in crops of useful plants and the use of the herbicidal compositions for controlling weeds. [Background technology]

[0002] Formula (I) [ka] are known from WO 2016 / 095768 and provide effective control of problematic weeds in crops. WO 2020 / 063613 provides further methods for producing such compounds.

[0003] Combinations of herbicidal active ingredients are often used in agriculture to increase and / or broaden the control effect of problem plants (weeds) in crops of useful plants. In some instances, the combination can produce a valuable (synergistic) effect that is more than additive, which can, for example, allow for efficient weed control at lower application rates. The present invention is based on novel compositions comprising compounds of formula (I). Summary of the Invention [Means for solving the problem]

[0004] Thus, in accordance with the present invention, (A) a herbicidally effective amount of a compound of formula (I): [ka] (In the formula, R 1 is selected from hydrogen, chloro and fluoro; R 2 is selected from chloro and bromo; R 3 is CO2R 5 and CH2OR6 is selected from R 4 is selected from H, CH3- and CH3CH2-; R 5 is selected from H, CH3-, CH3CH2-, CH3CH2CH2-, CH3CH2CH2CH2-, (CH3)2CH-, (CH3)2CHCH2-, (CH3)3C-, CF3CH2-, allyl, propargyl, CH3OCH2CH2-, C2H5OCH2CH2-, CH3CO2CH2CH2- and tetrahydrofuranmethyl; R 6 is selected from C1-C4 alkylcarbonyl, cyclopropylcarbonyl, and C1-C2 alkylsulfonyl or an agrochemically acceptable salt thereof, A herbicidal composition is provided in which component (B) is glufosinate or L-glufosinate, or an agrochemically acceptable ester or salt thereof.

[0005] US Pat. No. 4,168,963 and US Pat. No. 4,216,226 describe the use of glufosinate or L-glufosinate, respectively.

[0006] It is an object of the present invention to provide alternative and / or improved herbicidal mixtures which are highly effective against a variety of weed species (especially at low doses) and which are based on the finding that compounds of formula (I) in combination with glufosinate or L-glufosinate are particularly effective in controlling weeds. DETAILED DESCRIPTION OF THE INVENTION

[0007] In a preferred embodiment of the present invention, component (A) is a compound of formula (I), wherein: R 1 is selected from chloro and fluoro, preferably R 1 is fluoro, R 2 is selected from chloro and bromo, preferably R 2 is chloro, R 3is CO2R 5 and R 4 is selected from H, CH3 and CH3CH2-, preferably R 4 is CH3-, R 5 is selected from H, CH3, CH3CH2-, CH3CH2CH2-, CH3CH2CH2CH2-, (CH3)2CH-, (CH3)2CHCH2-, and (CH3)3C-, preferably R 5 is CH3CH2-.

[0008] In a more preferred embodiment of the invention, the compound of formula (I) is a compound of formula (Ia). [ka]

[0009] In a preferred embodiment of the present invention, component (B) is glufosinate.

[0010] In another preferred embodiment of the present invention, component (B) is L-glufosinate.

[0011] In preferred compositions according to the present invention, the weight ratio of component (A) to component (B) is from 1:1 to 1:50.

[0012] In more preferred compositions according to the present invention, the weight ratio of component (A) to component (B) is from 1:3 to 1:50.

[0013] In even more preferred compositions according to the present invention, the weight ratio of component (A) to component (B) is from 1:4 to 1:32.

[0014] In a second aspect of the invention, there is provided a herbicidal composition according to the invention further comprising at least one additional pesticide.

[0015] In preferred compositions according to the second aspect of the invention, the additional pesticide is a herbicide or a herbicide safener.

[0016] In more preferred compositions according to the second aspect of the invention, the additional pesticide is a herbicide selected from the group consisting of paraquat dibromide, diquat dibromide, saflufenacil, trifludimoxadine, thiafenacil, pyroxasulfone, S-metolachlor, bicyclopyrone, glyphosate, mesotrione, metribuzin, and [3-(2-methoxy-4-prop-1-ynyl-phenyl)-4-oxo-2-bicyclo[3.2.1]oct-2-enyl]methyl carbonate.

[0017] In more preferred compositions according to the second aspect of the invention, the additional pesticide is a herbicide safener selected from the group consisting of benoxacor, cloquintocet, cyprosulfamide, dichlormid, fenchlorazole, fenclorim, fluxofenim, furilazole, isoxadifen, mefenpyr, metcamifen and oxabetrinil.

[0018] In a third aspect of the invention there is provided a method of controlling weeds in a locus, the method comprising the step of applying to the locus of the weeds a control amount of a composition of the invention.

[0019] In a fourth aspect of the invention there is provided a method for selectively controlling weeds in a locus comprising crop plants and weeds, the method comprising applying to the weeds in the locus a control amount of a composition according to the invention. In a preferred method according to the fourth aspect of the invention the crop plants are oil palm, maize, cereals or soybeans.

[0020] In a preferred method according to the fourth aspect of the invention, the weeds are selected from the group consisting of Amaranthus sp., Ipomoea sp., Erigeron sp., Kochia sp., Borrelia sp., Commelina sp., Portulaca sp., Chenopodium sp., Abutilon sp., Stellaria sp., Eleusine sp., Brachiaria sp., Digitaria sp., Echinochloa sp., Setaria sp., Sorghum sp. sp.), and Lolium sp.

[0021] In another aspect, there is provided a method for controlling the growth of PPO-resistant weeds, the method comprising applying to weeds, parts of weeds, weed propagation material, or a habitat of the weeds an effective amount of a composition according to the present invention, wherein the PPO-resistant weeds are weeds that are resistant to at least one PPO-inhibiting herbicide other than a compound of Formula (I) and have a mutation at amino acid position 98, amino acid position 210, amino acid position 361, and / or amino acid position 399 in a gene encoding the protoporphyrinogen oxidase enzyme.

[0022] In another aspect, a method for controlling the growth of PPO-resistant weeds is provided, the method comprising applying to weeds, parts of weeds, weed propagation material, or a locus of the weeds an effective amount of a composition according to the invention, wherein the PPO-resistant weeds have a mutation at amino acid position 98, amino acid position 210, and / or amino acid position 399 in a gene encoding the protoporphyrinogen oxidase enzyme.

[0023] In another aspect, the present invention also relates to the use of the compositions according to the present invention for controlling weeds that are resistant to other PPO herbicides, excluding the compounds of formula (I), such as flumioxazin, fomesafen, and / or lactofen. Weeds may acquire resistance to PPO herbicides by evolution, traditional breeding methods, or genetic engineering. Examples include palm weed (Amaranthus palmeri) and water chestnut (Amaranthus tuberculatus), which have evolved tolerance to PPO herbicides.

[0024] In another aspect, the use of the composition according to the present invention is provided by applying it to the top of a crop that is resistant to a PPO inhibitor.As a known PPO inhibitor, it is clear that the compound of formula (Ia) can be used in a method for controlling undesirable vegetation in a crop plant that is resistant to a protoporphyrinogen oxidase (PPO) inhibitor.Such a plant can be obtained, for example, by transforming the crop plant with a nucleic acid encoding a suitable protoporphyrinogen oxidase, and this nucleic acid may contain a mutation that confers greater resistance to a PPO inhibitor. Examples of such nucleic acids and crop plants are described in WO 95 / 34659, WO 97 / 32011, WO 2007 / 024739, WO 2012 / 080975, WO 2013 / 189984, WO 2015 / 022636, WO 2015 / 022640, WO 2015 / 092706, WO 201 These are disclosed in International Publication Nos. 6 / 099153, WO 2017 / 023778, WO 2017 / 039969, WO 2017 / 217793, WO 2017 / 217794, WO 2018 / 114759, WO 2019 / 117578, WO 2019 / 117579, and WO 2019 / 118726. In a preferred embodiment, the crop plant resistant to a PPO inhibitor comprises a gene encoding the HemG enzyme H_N90, as disclosed in WO 2017 / 023778 and WO 2024 / 015950. In another preferred embodiment, the crop plant resistant to a PPO inhibitor is cotton, corn, or soybean.

[0025] When active ingredients are combined, the expected activity (E) for any given active ingredient combination can be calculated according to the so-called Colby formula as follows (Colby, S.R., Calculating synergistic and antagonistic responses of herbicide combinations, Weeds, Vol. 15, pages 20-22; 1967): ppm = milligrams of active ingredient per liter (ai) X = % effect of the first active ingredient using p ppm of active ingredient Y = % effect of the second active ingredient with q ppm of active ingredient. According to Colby, the expected effect of active ingredients A+B using p+q ppm of active ingredients is expressed by the following formula:

number

[0026] If the actual observed effect (O) is greater than the expected effect E, the effect of the combination is superadditive, i.e., synergy exists. Mathematically, synergy corresponds to a positive value for the difference (OE). In the case of a purely complementary addition of activity (expected activity), the difference (OE) is zero. A negative value for the difference (OE) indicates a loss of activity compared to the expected activity.

[0027] Surprisingly, the combinations of the present invention exhibit additive herbicidal activity, and certain embodiments may even exhibit synergistic effects. A synergistic effect occurs whenever the action of the combination of active ingredients is greater than the sum of the actions of the individual ingredients.

[0028] The combinations of the present invention may also provide a broader range of activity compared to the activity provided by each of the individual components and / or may allow the use of lower amounts of the individual components when used in combination than when used alone to mediate effective herbicidal activity.

[0029] It is also possible that the compositions of the invention may exhibit increased crop resistance when compared to the effect of compound A alone. This occurs when the action of the combination of active ingredients is less damaging to useful crops than the action of one of the active ingredients alone.

[0030] When component (A) is a compound of formula (Ia), formula (Ia) is referred to in WO 2016 / 095768 as compound 6. This can be prepared according to Example 1 of WO 2016 / 095768.

[0031] As used herein, the term "C1-C4 alkyl" refers to a straight or branched hydrocarbon chain radical consisting solely of carbon and hydrogen atoms, containing no unsaturation, having from 1 to 4 carbon atoms, and attached to the rest of the molecule by a single bond. 1-4 Examples of alkyl include, but are not limited to, methyl (e.g., CH3-), ethyl (e.g., CH3CH2-), n-propyl, n-butyl, and their isomers such as iso-propyl, iso-butyl, sec-butyl, or tert-butyl.

[0032] As used herein, "C 1- The term "C4 alkylcarbonyl" refers to a is a C1-C4 alkyl group as generally defined above, a Examples of C1-C4 alkylcarbonyl include, but are not limited to, acetyl.

[0033] As used herein, the term "C1-C2 alkylsulfonyl" refers to a group of the formula -S(O)R a where R a is a C1-C2 alkyl group as generally defined above. Examples of C1-C2 alkylsulfonyl include, but are not limited to, methylsulfonyl.

[0034] Throughout this specification, the term "composition" should be interpreted to mean various mixtures or combinations of components (A) and (B), for example, in a single "ready-mix" form, in a combined spray mixture such as a "tank mix" composed of separate formulations of a single active ingredient, and in combination with a single active ingredient when applied in a sequential manner, i.e., within a reasonably short period of time, such as a few hours or days. The order in which components (A) and (B) are applied is not critical to the practice of the invention. Preferably, they are in a single ready-mix form.

[0035] As used herein, the term "herbicide" refers to a compound that controls or modifies plant growth. The term "herbicidally effective amount" refers to the amount of such a compound or combination of such compounds that is capable of producing a controlling or modifying effect on plant growth. A controlling or modifying effect includes any deviation from natural development, such as killing, retardation, leaf scorch, bleaching, dwarfing, etc.

[0036] As used herein, the term "habitat" means the soil in which plants are growing or in which seeds of cultivated plants are sown or in which seeds will be sown in the soil. It includes the soil, seeds and seedlings, and established vegetation.

[0037] The term "plant" refers to all physical parts of a plant, including seeds, seedlings, saplings, roots, tubers, stems, stalks, leaves, and fruits.

[0038] The term "plant propagation material" means all reproductive parts of a plant, for example seeds or cuttings and growing parts of a plant such as tubers, etc. This includes not only seeds in the strict sense, but also roots, fruits, tubers, bulbs, rhizomes and plant parts.

[0039] As used herein, the term "safener" means a chemical that, when used in combination with a herbicide, reduces the undesirable effects of the herbicide on non-target organisms; for example, the safener protects a crop from herbicide injury but does not prevent the herbicide from killing weeds.

[0040] Crops of useful plants in which the compositions according to the invention can be used include berry plants, such as blackberries, blueberries, cranberries, raspberries and strawberries; cereals, such as barley, maize (corn), millet, oats, rice, rye, sorghum, triticale and wheat; fiber plants, such as cotton, flax, hemp, jute and sisal; field crops, such as sugar and fodder beet, coffee, hops, mustard, rapeseed (canola), poppy, sugarcane, sunflower, tea and tobacco; fruit trees, such as apple, apricot, avocado, banana, cherry, citrus fruit, nectarine, peach, pear and plum; grasses, such as bermudagrass, bluegrass, bentgrass, centipedegrass, fescue, ryegrass, St. Augustine grass and zoysiagrass; nuts such as almonds, cashews, groundnuts, hazelnuts, peanuts, pecans, pistachios and walnuts; palms such as oil palm; ornamental plants such as flowers, shrubs and trees; other trees such as cocoa, coconut, olives and rubber; vegetables such as asparagus, eggplant, broccoli, cabbage, carrots, cucumber, garlic, lettuce, marrow, melon, okra, onion, pepper, potato, pumpkin, rhubarb, spinach and tomato; and perennial and annual crops such as vines.

[0041] Preferably, the compositions of the present invention are used to control weeds in oil palm, corn, cereals or soybeans.

[0042] Crops are to be understood as those occurring naturally, obtained by conventional breeding methods, or obtained by genetic engineering, including crops with so-called output traits (e.g., improved storage stability, high nutritional value, and improved flavor).

[0043] Crops should also be understood to include crops that have been rendered tolerant to herbicides or classes of herbicides (e.g., ALS inhibitors, GS inhibitors, EPSPS inhibitors, PPO inhibitors, ACCase inhibitors, and HPPD inhibitors) by conventional breeding methods or genetic engineering. An example of a crop that has been rendered tolerant to imidazolinones (e.g., imazamox) by conventional breeding methods is Clearfield® summer rapeseed (canola). Examples of crops that have been rendered tolerant to herbicides by genetic engineering methods include corn varieties that are resistant to glyphosate and glufosinate, such as those commercially available under the trade names RoundupReady® and LibertyLink®.

[0044] It should also be understood that crops may be genetically engineered to resist pests, such as Bt corn (resistant to the European corn borer), Bt cotton (resistant to the cotton weevil), and Bt potato (resistant to the Colorado potato beetle). An example of Bt corn is the Bt 176 corn hybrid from NK® (Syngenta Seeds). Bt toxins are proteins naturally produced by the soil bacterium Bacillus thuringiensis. Examples of toxins or genetically engineered plants capable of synthesizing such toxins are described in EP 451 878, EP 374 753, WO 93 / 07278, WO 95 / 34656, WO 03 / 052073, and EP 427 529. Examples of transgenic plants containing one or more genes encoding insecticide resistance and expressing one or more toxins are KnockOut® (corn), Yield Gard® (corn), NuCOTIN33B® (cotton), Bollgard® (cotton), NewLeaf® (potato), NatureGard®, and Protexcta®. Plant crops or their seed materials can be resistant to herbicides and insect feeding at the same time ("stacked" transgenic events). For example, seeds can be capable of expressing the insecticidal Cry3 protein and also be tolerant to glyphosate.

[0045] Examples of crops that have been genetically engineered to be tolerant to PPO-inhibiting herbicides are known in the art, for example, as described in WO 95 / 34659. Examples of crops that have been genetically engineered to be tolerant to HPPD-inhibiting herbicides are known in the art, for example, as described in WO 2011 / 063411, WO 2011 / 063413, WO 2012 / 082542, WO 2012 / 082548, WO 2010 / 085705, and WO 2011 / 068567.

[0046] The compositions of the present invention can typically be used to control a wide variety of monocotyledonous and dicotyledonous weed species. Examples of monocotyledonous species that can typically be controlled include Alopecurus species (e.g. Alopecurus myosuroides), Avena species (e.g. Avena fatua), Brachiaria species (e.g. Brachiaria plantaginea), Bromus species (e.g. Bromus tectorum), Cyperus species (e.g. Cyperus esculentus), Digitaria species (e.g. Digitaria sanguinalis), Echinochloa species (e.g. sp. (e.g., Echinochloa crus-galli), Eleusine sp. (e.g., Eleusine indica), Lolium sp. (e.g., Lolium perenne, Lolium multiflorum), Panicum sp. (e.g., Panicum miliaceum), Poa sp. (e.g., Poa annua), Setaria sp. (e.g., Setaria viridis, Setaria faberi), and Sorghum sp. (e.g., Sorghum bicolor).Examples of dicotyledonous species that can be controlled include Abutilon species (e.g. Abutilon theophrasti), Amaranthus species (e.g. Amaranthus retroflexus, Amaranthus palmeri), Bidens species (e.g. Bidens pilosa), Chenopodium species (e.g. Chenopodium album), Conyza species (e.g. Conyza canadensis), Euphorbia species (e.g. Euphorbia heterophylla), Galium species. (e.g., Galium aparine), Ipomoea sp. (e.g., Ipomoea hederacea), Kochia sp. (e.g., Kochia scoparia), Polygonum sp. (e.g., Polygonum convolvulus), Sida sp. (e.g., Sida spinosa), Sinapis sp. (e.g., Sinapis arvensis), Solanum sp. (e.g., Solanum nigrum), Stellaria sp. (e.g., Stellaria media), Veronica sp. (for example, Veronica persica) and Xanthium sp. (for example, Xanthium strumarium).

[0047] Preferably, the composition of the present invention is effective against Amaranthus sp., Ipomoea sp., Erigeron sp., Kochia sp., Borrelia sp., Commelina sp., Portulaca sp., Chenopodium sp., Abutilon sp., Stellaria sp., Eleusine sp., Brachiaria sp., Digitaria sp., Echinochloa sp., Setaria sp., Sorghum sp., Phalaris sp. It is used to control Sorghum sp., Sorghum sp., Euphorbia sp., Fallopia sp., and Lolium sp.

[0048] More preferably, the composition of the present invention is effective against Amaranthus sp., Ipomoea sp., Erigeron sp., Kochia sp., Borrelia sp., Commelina sp., Portulaca sp., Chenopodium sp., Abutilon sp., Stellaria sp., Eleusine sp., Brachiaria sp., Digitaria sp., Echinochloa sp., Setaria sp., Sorghum sp., and Lolium sp. It is used to control (sp.).

[0049] Even more preferably, the compositions of the invention are used to control Amaranthus sp., Ipomoea sp., Chenopodium sp., Abutilon sp., Stellaria sp., Digitaria sp., Echinochloa sp. and Setaria sp.

[0050] In one aspect, the compositions of the invention are used to control Digitaria sp., Echinochloa sp., Setaria sp., Amaranthus sp., Chenopodium sp., Abutilon sp., Ipomoea sp., Phalaris sp., Sorghum sp., Euphorbia sp., Fallopia sp., and Eleusine indica.

[0051] In another aspect, the compositions of the invention are used to control Digitalia sanguinalis, barnyard grass (Echinochloa crus-galli), foxtail (Setaria faberi), chickweed (Stellaria media), redroot pigweed (Amaranthus retroflexus), lamb's quarter (Chenopodium album), Abutilon theophrasti, Ipomoea hederacea, Phalaris minor, velvetleaf (Sorghum bicolor), false heartworm (Euphorbia heterophylla), bindweed (Fallopia convolvulus), and goosegrass (Eleusine indica).

[0052] In all aspects of the invention, in any particular embodiment, for example, the weeds to be controlled and / or inhibited may be monocotyledonous or dicotyledonous weeds that are tolerant or resistant to one or more other herbicides, for example, HPPD-inhibiting herbicides such as mesotrione, PSII-inhibiting herbicides such as atrazine, or EPSPS inhibitors such as glyphosate. Such weeds include, but are not limited to, resistant Amaranthus biotypes.

[0053] The compositions of the present invention can also be mixed with one or more additional pesticides, including herbicides (typically different from herbicides (A) and (B)), fungicides, insecticides, nematicides, bactericides, miticides, growth regulators, sterilizers, signal chemicals, repellents, attractants, pheromones, feeding stimulants or other biologically active compounds, to form multi-component pesticides that provide an even broader range of agricultural protection.

[0054] Preferred herbicides as additional mixing partners are acetochlor, acifluorofen (including acifluorofen sodium), aclonifen, ametryn, amicarbazone, aminopyralid, aminotriazole, atrazine, beflubutamid-M, benquitrione, bensulfuron (including bensulfuron methyl), bentazone, bicyclopyrone, vilafos, bipyrazone, bispyribac-sodium, biclozone, broclozone, bromacil, bromoxynil, butachlor, butafenacil, carfentrazone (carfentrazone ethyl). chloransulam (including cloransulam methyl), chlorimuron (including chlorimuron ethyl), chlorotoluron, chlorsulfuron, cinmethylin, clasifos, clethodim, clodinafop (including clodinafop propargyl), clomazone, clopyralid, cyclopyranyl, cyclopirimorate, cyclosulfamuron, cyhalofop (including cyhalofop butyl), 2,4-D (including choline salts and their 2-ethylhexyl esters), 2,4-DB, desmedipham, dicamba (aluminum, aminopropyl, bis-aminopropyl) Propylmethyl, choline, dichloroprop, diglycolamine, dimethylamine, dimethylammonium, potassium and their sodium salts) diclosulam, diflufenican, diflufenopyr, dimethachlor, dimethenamid-P, dioxopyritrion, diquat dibromide, diuron, epirifenacil, ethalfluralin, ethofumesate, fenoxaprop (including fenoxaprop-P-ethyl), fenoxasulfone, fenoxapyrazon, fenquinotrione, fentrazamide, flazasulfuron, florasulam, Florpiraxifen (including florpiraxifen-benzyl), fluazifop (including fluazifop-p-butyl), flucarbazone (including flucarbazone sodium), fluchloroaminopyr (including fluchloroaminopyr tefuril), flufenacet, flufenoximacil, flumetsulam, flumioxazin, fluometuron, fomesafen, flupyrsulfuron (including flupyrsulfuron methyl sodium), fluroxypyr (including fluroxypyr meptyl), flusulfinam, fomesafen, folamsulfuron,Glufosinate (including L-glufosinate and ammonium salts of both), glyphosate (including diammonium, isopropylammonium and their potassium salts), haloxifen (including haloxifen methyl), haloxyfop (including haloxyfop methyl), hexazinone, hydantocidin, icaforin (including icaforin methyl), imazamox (including R-imazamox), imazapic, imazapyr, imazethapyr, indaziflam, indorauxipyr (including indorauxipyr cyanomethyl), iodosulfuron (iodosulfuron) Iofensulfuron (including iofensulfuron sodium), ioxynil, iptriazopiride, isoproturon, isoxaflutole, lancotrione, MCPA, MCPB, mecoprop-P, mesosulfuron (including mesosulfuron methyl), mesotrione, metamitron, metazachlor, methiozoline, metolachlor, metosulam, metribuzin, metsulfuron, napropamide, nicosulfuron, norflurazon, oxadiazon, oxasulfuron, oxyfluorfen, paraquat Attodichloride, pendimethalin, penoxulam, phenmedipham, picloram, pinoxaden, pretilachlor, primisulfuron methyl, prometryn, propanil, propaquizafop, propyrisulfuron, propyzamide, prosulfocarb, prosulfuron, pyraclonil, pyraflufen (including pyraflufen-ethyl), pyraquinate, pyrasulfotole, pyridate, pyriftalid, pyriflubenzoxim, pyrimisulfan, pyroxasulfone, pyroxsulam, quinclorac, quinmerac, quizalofop (quizalofop) Quizalofop-P-tefuron (including tribenuron-P-ethyl and quizalofop-P-tefuryl), rimisoxafen, rimsulfuron, saflufenacil, sethoxydim, simazine, S-metallochlor, sulfentrazone, sulfosulfuron, tebuthiuron, tefuryltrione, tembotrione, terbuthylazine, terbutryn, tetolpyrrolimet, thiencarbazone, thifensulfuron, thiafenacil, tolpyralate, topramezone, tralkoxydim, triafamone, triallal, triasulfuron, tribenuron (including tribenuron methyl), triclopyr,Trifloxysulfuron (including trifloxysulfuron sodium), trifludimoxadine, trifluralin, triflusulfuron, tripyrasulfone, 3-(2-chloro-4-fluoro-5-(3-methyl-2,6-dioxo-4-trifluoromethyl-3,6-dihydropyrimidin-1(2H)-yl)phenyl)-5-methyl-4,5-dihydroisoxazole-5-carboxylic acid ethyl ester, 4-hydroxy-1-methoxy-5-methyl-3-[4-(trifluoromethyl)-2-pyridyl]imidazolidin-2-one , 4-hydroxy-1,5-dimethyl-3-[4-(trifluoromethyl)-2-pyridyl]imidazolidin-2-one, 5-ethoxy-4-hydroxy-1-methyl-3-[4-(trifluoromethyl)-2-pyridyl]imidazolidin-2-one, 4-hydroxy-1-methyl-3-[4-(trifluoromethyl)-2-pyridyl]imidazolidin-2-one, 4-hydroxy-1,5-dimethyl-3-[1-methyl-5-(trifluoromethyl)pyrazol-3-yl]imidazolidin-2-one, (4R)1-(5-tert-butyl) ethylisoxazol-3-yl)-4-ethoxy-5-hydroxy-3-methyl-imidazolidin-2-one, (1RS,5SR)-3-[2-methoxy-4-(prop-1-yn-1-yl)phenyl]-4-oxobicyclo[3.2.1]oct-2-en-2-ylmethyl carbonate, ethyl-2-[[3-[[3-chloro-5-fluoro-6-[3-methyl-2,6-dioxo-4-(trifluoromethyl)pyrimidin-1-yl]-2-pyridyl]oxy]acetate, methyl 2-[2-[2-bromo-4-fluoro-5-[ 3-methyl-2,6-dioxo-4-(trifluoromethyl)pyrimidin-1-yl]phenoxy]phenoxy]-2-methoxy-acetate, 6-chloro-4-(2,7-dimethyl-1-naphthyl)-5-hydroxy-2-methyl-pyridazin-3-one, (2-fluorophenyl)methyl 6-amino-5-chloro-2-(4-chloro-2-fluoro-3-methoxy-phenyl)pyrimidine-4-carboxylate, 6-amino-5-chloro-2-(4-chloro-2-fluoro-3-methoxy-phenyl)pyrimidine-4-carboxylic acid,methyl 3-[2-chloro-5-[3,6-dihydro-3-methyl-2,6-dioxo-4-(trifluoromethyl)-1(2H)-pyrimidinyl]-4-fluorophenyl]-3a,4,5,6-tetrahydro-6-methyl-6aH-cyclopento[d]isoxazole-6a-carboxylate, 2-[(2-bromo-6-fluoro-phenyl)methoxy]-4-isopropyl-1-methyl-7-oxabicyclo[2.2.1]heptane, and (isopropylideneamino)6-amino-2-(4-chloro-2-fluoro-3-methoxy-phenyl)-5-methoxy-pyrimidine-4-carboxylate.

[0055] Preferred herbicides as additional mixing partners include ametryn, atrazine, butafenacil, 2,4-D (including the choline salt and its 2-ethylhexyl ester), cloransulam, diclosulam, diuron, flazasulfuron, fluazifop (including fluazifop-p-butyl), flumioxazin, fluometuron, fomesafen, bicyclopyrone, glyphosate, indaziflam, isoxaflutole, metribuzin, mesosulfuron, mesotrione, S-metolachlor, pendimethalin, and prometryl. The following are benzodiazepines: pyroxasulfone, saflufenacil, simazine, sulfentrazone, thiafenacil, terbuthylazine, trifludimoxazine, trifluralin, ethyl 2-[[3-[2-chloro-4-fluoro-5-[3-methyl-2,6-dioxo-4-(trifluoromethyl)pyrimidin-1-yl]phenoxy]-2-pyridyl]oxy]acetate, and [3-(2-methoxy-4-prop-1-ynyl-phenyl)-4-oxo-2-bicyclo[3.2.1]oct-2-enyl]methyl carbonate. Even more preferred herbicides include atrazine, clethodim, 2,4-D (including the choline salt and its 2-ethylhexyl ester), dicamba (including aluminum, aminopropyl, bis-aminopropylmethyl, choline, dichloroprop, diglycolamine, dimethylamine, dimethylammonium, and its potassium and sodium salts), diquat dibromide, flazasulfuron, fluazifop (including fluazifop-p-butyl), flumioxazin, fomesafen, bicyclopyrone, glyphosate, isoxaflutole, metribuzin, mesohexyl benzoate, benzophenone, benzophenone-4, benzophenone-5, benzophenone-6, benzophenone-7, benzophenone-8, benzophenone-9, benzophenone-10, benzophenone-11, benzophenone-12, benzophenone-13, benzophenone-14, benzophenone-15, benzophenone-16, benzophenone-17, benzophenone-18, benzophenone-19, benzophenone-20, benzophenone-21, benzophenone-22, benzophenone-23, benzophenone-24, benzophenone-25, benzophenone-26, benzophenone-27, benzophenone-28, benzophenone-29, benzophenone-30, benzophenone-31, benzophenone-32, benzophenone-33, benzophenone-34, benzophenone-35, benzophenone-36, benzophenone-37, benzophenone-38, benzophenone-39, benzophenone-40, benzophenone-41, benzophenone-42, benzophenone-43, benzophenone-44, benzophenone-45, benzophenone-46, benzophenone-4 and / or selected from one or more of sulfuron, mesotrione, S-metolachlor, paraquat dibromide, pyroxasulfone, saflufenacil, sulfentrazone, thiafenacil, trifludimoxadine, ethyl 2-[[3-[2-chloro-4-fluoro-5-[3-methyl-2,6-dioxo-4-(trifluoromethyl)pyrimidin-1-yl]phenoxy]-2-pyridyl]oxy]acetate, and [3-(2-methoxy-4-prop-1-ynyl-phenyl)-4-oxo-2-bicyclo[3.2.1]oct-2-enyl]methyl carbonate.The most preferred herbicides are selected from the group consisting of paraquat dibromide, diquat dibromide, saflufenacil, trifludimoxadine, thiafenacil, pyroxasulfone, S-metolachlor, bicyclopyrone, glyphosate, mesotrione, metribuzin, and [3-(2-methoxy-4-prop-1-ynyl-phenyl)-4-oxo-2-bicyclo[3.2.1]oct-2-enyl]methyl carbonate.

[0056] Similarly, compositions of the present invention (including those containing one or more additional pesticides as described in the previous paragraph) can further comprise one or more safeners. In particular, the following safeners are particularly preferred: AD 67 (MON 4660), benoxacor, cloquintocet (including cloquintocet-mexyl), cyometrinil, cyprosulfamide, dichlormid, dicyclonone, diethrate, fenchlorazole (including fenchlorazole-ethyl), fenclorim, flurazole, fluxofenim, furilazole, furilasome, isoxadifen (including isoxadifen-ethyl), mefenpyr (including mefenpyr-diethyl), mefenate, metcamifen, oxabetrinil, naphthalic anhydride (CAS RN 81-84-5), TI-35, N-isopropyl-4-(2-methoxy-benzoylsulfamoyl)-benzamide (CAS RN 81-84-5), CI ... 221668-34-4) and N-(2-methoxybenzoyl)-4-[(methylaminocarbonyl)amino]benzenesulfonamide, and more preferably benoxacor, cloquintocet, cyprosulfamide, dichlormid, fenchlorazole, fenclorim, fluxofenim, furilazole, isoxadifen, mefenpyr, metcamifen, and oxabetrinil. Such safeners may also be used in the form of esters or salts, as described, for example, in The Pesticide Manual, 15th Ed. (BCPC), 2009. Thus, for example, a reference to cloquintocet-mexyl also applies to cloquintocet and its lithium, sodium, potassium, calcium, magnesium, aluminum, iron, ammonium, quaternary ammonium, sulfonium, or phosphonium salts, as disclosed in WO 02 / 34048; a reference to fenchlorazole-ethyl also applies to fenchlorazole, etc.

[0057] The composition of the present invention can be applied before or after planting of crops, before weed emergence (pre-emergence application) or after weed emergence (post-emergence application). When a safener is combined with the mixture of the present invention, the mixing ratio of compound (A) to safener is preferably 100:1 to 1:10, more preferably 20:1 to 1:1.

[0058] The safener and the composition of the present invention can be applied simultaneously. For example, the safener and the composition of the present invention can be applied to the habitat before emergence or to the crop after emergence. The safener and the composition of the present invention can also be applied sequentially. For example, the safener can be applied as a seed treatment before sowing the seeds. Also, the composition of the present invention can be applied to the habitat before emergence or to the crop after emergence.

[0059] However, those skilled in the art will recognize that the compositions of the present invention are particularly useful in non-selective burn-down applications and may therefore also be used to control volunteer vegetation or to retreat crop plants, in which situation there is clearly no need to include a safener in the compositions of the present invention.

[0060] The weight ratio of any two materials in each combination is selected to achieve a desired, e.g., synergistic, effect. Generally, the weight ratio will vary depending on the specific materials and the number of materials present in the combination. Generally, the weight ratio between any two materials in any combination of the present invention, independently of one another, can be 99:1, 98:2, 97:3, 96:4, 95:5, 94:6, 93:7, 92:8, 91:9, 90:10, 89:11, 88:12, 87:13, 86:14, 85:15, 84:16, 83:17, 82:18, 81:19, 80:20, 79:2 1, 78:22, 77:23, 76:24, 75:25, 74:26, 73:27, 72:28, 71:29, 70:30, 69:31, 68:32, 67:33, 66:34, 65:45, 64:46, 63:47, 62:48, 61:49, 60:40, 59:41, 58:42, 57:43, 56:44, 55:45, 54:46, 53:47, 52:49, 53:52 :48, 51:49, 50:50, 49:51, 48:52, 47:53, 46:54, 45:55, 44:56, 43:57, 42:58, 41:59, 40:60, 39:61, 38:62, 37:63, 36:64, 35:65, 34:66, 33:67, 32:68, 31:69, 30:70, 29:71, 28:72, 27:73, 26:74, The preferred weight ratio between any two components of the present invention is 100:1 to 1:100, including 25:75, 24:76, 23:77, 22:78, 21:79, 20:80, 19:81, 18:82, 17:83, 16:84, 15:85, 14:86, 13:87, 12:88, 11:89, 10:90, 9:91, 8:92, 7:93, 6:94, 5:95, 4:96, 3:97, 2:98, to 1:99. The preferred weight ratio between any two components of the present invention is 75:1 to 1:75, more preferably 1:1 to 1:50, especially 1:3 to 1:50, advantageously 1:3 to 1:32, for example 1:4 to 1:32, such as 1:4 to 1:24 or 1:8 to 1:16. Mixing ratios are understood to include, on the one hand, mass ratios and, on the other hand, molar ratios.

[0061] In a preferred composition according to the present invention, component (A) is a compound of formula (Ia) or a salt, tautomer or N-oxide thereof, component (B) is glufosinate, and the weight ratio of component (A) to component (B) is from 1:1 to 1:50.

[0062] In a more preferred composition according to the present invention, component (A) is a compound of formula (Ia) or a salt, tautomer or N-oxide thereof, component (B) is glufosinate, and the weight ratio of component (A) to component (B) is 1:3 to 1:50.

[0063] In the most preferred compositions according to the present invention, component (A) is a compound of formula (Ia) or a salt, tautomer or N-oxide thereof, component (B) is glufosinate, and the weight ratio of component (A) to component (B) is from 1:4 to 1:32.

[0064] In a preferred composition according to the present invention, component (A) is a compound of formula (Ia) or a salt, tautomer or N-oxide thereof, component (B) is L-glufosinate, and the weight ratio of component (A) to component (B) is from 1:1 to 1:50.

[0065] In a more preferred composition according to the present invention, component (A) is a compound of formula (Ia) or a salt, tautomer or N-oxide thereof, component (B) is L-glufosinate, and the weight ratio of component (A) to component (B) is 1:3 to 1:50.

[0066] In the most preferred compositions according to the present invention, component (A) is a compound of formula (Ia) or a salt, tautomer or N-oxide thereof, component (B) is L-glufosinate, and the weight ratio of component (A) to component (B) is 1:4 to 1:32.

[0067] In another embodiment, there is provided a composition of components (A) and (B), wherein component (A) is a compound of formula (Ia) and component (B) is glufosinate, and the weight ratio of components (A) to (B) is from 1:4 to 1:16.

[0068] In another embodiment, there is provided a composition of components (A) and (B), wherein component (A) is a compound of formula (Ia) and component (B) is glufosinate, and the weight ratio of components (A) to (B) is 1:4.

[0069] In another embodiment, there is provided a composition of components (A) and (B), wherein component (A) is a compound of formula (Ia) and component (B) is glufosinate, and the weight ratio of components (A) to (B) is 1:8.

[0070] In another embodiment, there is provided a composition of components (A) and (B), wherein component (A) is a compound of formula (Ia) and component (B) is glufosinate, and the weight ratio of components (A) to (B) is 1:16.

[0071] In another embodiment, there is provided a composition of components (A) and (B), wherein component (A) is a compound of formula (Ia) and component (B) is glufosinate, wherein the weight ratio of components (A) to (B) is from 1:4 to 1:16, and the species to be controlled are Phalaris minor (PHAMI), Sorghum bicolor (SORVU), Euphorbia heterophylla (EPHHL), Fallopia convolvulus (POLCO), Digitalia sanguinalis (DIGSA), Echinochloa crus-galli (ECHCG), Setaria faberi (SETTA), Stellaria media (STEME), Amaranthus retroflexus (Amaranthus retroflexus) (AMARE), (CHEAL), American morning glory (Ipomoea hederacea) (IPOHE) or velvetleaf (Abutilon theophrasti) (ABUTH).

[0072] In another embodiment, there is provided a composition of components (A) and (B), wherein component (A) is a compound of formula (Ia) and component (B) is glufosinate, wherein the weight ratio of components (A) to (B) is 1:4, and the species to be controlled is Phalaris minor (PHAMI), Sorghum bicolor (SORVU), Euphorbia heterophylla (EPHHL), or Fallopia convolvulus (POLCO).

[0073] In another embodiment, there is provided a composition of components (A) and (B), wherein component (A) is a compound of formula (Ia) and component (B) is glufosinate, the weight ratio of components (A) to (B) is 1:8, and the species to be controlled is Digitalia sanguinalis (DIGSA), Echinochloa crus-galli (ECHCG), Setaria faberi (SETFA), Stellaria media (STEME), Amaranthus retroflexus (AMARE), (CHEAL), or Abutilon theophrasti (ABUTH).

[0074] In another embodiment, there is provided a composition of components (A) and (B), wherein component (A) is a compound of formula (Ia) and component (B) is glufosinate, the weight ratio of components (A) to (B) is 1:16, and the species to be controlled is barnyardgrass (Echinochloa crus-galli) (ECHCG), Setaria faberi (SETTA), common chickweed (Stellia media) (STEME), redroot pigweed (Amaranthus retroflexus) (AMARE), velvetleaf (Abutilon theophrasti) (ABUTH), or American morning glory (Ipomoea hederacea) (IPOHE).

[0075] In another embodiment, there is provided a composition of components (A) and (B), wherein component (A) is a compound of formula (Ia) and component (B) is L-glufosinate, and the weight ratio of components (A) to (B) is from 1:4 to 1:16.

[0076] In another embodiment, there is provided a composition of components (A) and (B), wherein component (A) is a compound of formula (Ia) and component (B) is L-glufosinate, and the weight ratio of components (A) to (B) is 1:4.

[0077] In another embodiment, there is provided a composition of components (A) and (B), wherein component (A) is a compound of formula (Ia) and component (B) is L-glufosinate, and the weight ratio of components (A) to (B) is 1:8.

[0078] In another embodiment, there is provided a composition of components (A) and (B), wherein component (A) is a compound of formula (Ia) and component (B) is L-glufosinate, and the weight ratio of components (A) to (B) is 1:16.

[0079] In another embodiment, there is provided a composition of components (A) and (B), wherein component (A) is a compound of formula (Ia) and component (B) is L-glufosinate, the weight ratio of components (A) to (B) is from 1:4 to 1:16, and the species to be controlled is (ELEIN), Fallopia convolvulus (POLCO), Echinochloa crus-galli (ECHCG), Stellaria media (STEME), Amaranthus retroflexus (AMARE), or Ipomoea hederacea (IPOHE).

[0080] In another embodiment, there is provided a composition of components (A) and (B), wherein component (A) is a compound of formula (Ia) and component (B) is L-glufosinate, wherein the weight ratio of components (A) to (B) is 1:4, and the species controlled is (ELEIN), or Fallopia convolvulus (POLCO).

[0081] In another embodiment, there is provided a composition of components (A) and (B), wherein component (A) is a compound of formula (Ia) and component (B) is L-glufosinate, wherein the weight ratio of components (A) to (B) is 1:8, and the species to be controlled is barnyardgrass (Echinochloa crus-galli) (ECHCG), redroot pigweed (Amaranthus retroflexus) (AMARE), or American morning glory (Ipomoea hederacea) (IPOHE).

[0082] In another embodiment, there is provided a composition of components (A) and (B), wherein component (A) is a compound of formula (Ia) and component (B) is glufosinate, wherein the weight ratio of components (A) to (B) is 1:16, and the species to be controlled is barnyardgrass (Echinochloa crus-galli) (ECHCG), chickweed (Stellaria media) (STEME), redroot pigweed (Amaranthus retroflexus) (AMARE), or morning glory (Ipomoea hederacea) (IPOHE).

[0083] When applied in the compositions of the present invention, component (A) is typically applied at a rate of 25 to 2000 g / ha, more specifically 25, 50, 75, 100, 125, 150, 200, 250, 300, 400, 500, 750, 800, 1000, 1250, 1500, 1800 or 2000 g / ha. Such rates of component (A) are typically applied in conjunction with component (B) at a rate of 5 to 2000 g / ha, and more specifically with component (B) at a rate of 10, 15, 25, 30, 60, 75, 100, 125, 200, 250, 300, 350, 375, 400, 450, 500, 750 or 1000 g / ha.

[0084] The examples provided herein illustrate, but do not limit, the ranges of proportions of components (A) and (B) that may be employed in the present invention.

[0085] The amount of the composition according to the invention to be applied can depend on various factors, such as the compound used; the target of treatment, e.g., plants, soil, or seeds; the type of treatment, e.g., spraying, dusting, or seed dressing; or the time of application. In agricultural practice, the application rate of the composition according to the invention depends on the type of effect desired and is usually in the range of 35 to 4000 g of total composition per hectare, more usually 35 to 2000 g / ha. Application is generally carried out by spreading the composition, typically with a tractor-mounted broad-area sprayer, although other methods, such as dusting (in the case of dusts), drip irrigation, or drench, can also be used.

[0086] The compositions of the present invention can be advantageously used in the following formulations (in which "active ingredient" refers to a mixture of compound (A) and compound (B), respectively, or, if a safener is also used, a mixture of compound (A) and compound (B) and the safener, respectively):

[0087] The individual components of the compositions of the present invention can be used as technical active ingredients as they are prepared. However, more generally, the compositions of the present invention can be formulated in various ways using formulation auxiliaries such as carriers, solvents, and surfactants. The formulations can be in various physical forms, such as dusts, gels, wettable powders, water-dispersible granules, water-dispersible tablets, effervescent pellets, emulsifiable concentrates, microemulsifiable concentrates, oil-in-water emulsions, oil flowables, aqueous dispersions, oil dispersions, suspoemulsions, capsule suspensions, emulsifiable granules, soluble liquids, water-soluble concentrates (with water or a water-miscible organic solvent as a carrier), impregnated polymer films, or other forms known, for example, from the Manual on Development and Use of FAO and WHO Specifications for Pesticides, United Nations, First Edition, Second Revision (2010). Such formulations can be used directly or diluted before use. Dilution can be carried out, for example, with water, liquid fertilizers, micronutrients, biological materials, oils, or solvents.

[0088] The formulations can be prepared by mixing the active ingredient with formulation adjuvants to obtain compositions in the form of, for example, finely divided solids, granules, solutions, dispersions or emulsions. The active ingredient can also be formulated with other adjuvants, such as finely divided solids, mineral oils, oils of vegetable or animal origin, modified oils of vegetable or animal origin, organic solvents, water, surfactants or combinations thereof.

[0089] The active ingredient can also be contained in very fine microcapsules. Microcapsules contain the active ingredient in a porous carrier, allowing the active ingredient to be released into the environment in controlled amounts (e.g., sustained release). Microcapsules typically have diameters of 0.1 to 500 micrometers. They contain the active ingredient in an amount of about 25 to 95% by weight of the capsule. The active ingredient can be in the form of a monolithic solid, in the form of fine particles in a solid or liquid dispersion, or in the form of a suitable solution. The encapsulating membrane can comprise, for example, natural or synthetic rubber, cellulose, styrene / butadiene copolymer, polyacrylonitrile, polyacrylate, polyester, polyamide, polyurea, polyurethane, or chemically modified polymers and starch xanthate, or other polymers known to those skilled in the art. Alternatively, very fine microcapsules can be formed in which the active ingredient is contained in the form of fine particles in a solid matrix of a substrate material, but the microcapsules themselves are not encapsulated.

[0090] Suitable formulation adjuvants for preparing the compositions according to the invention are known per se. Liquid carriers that can be used include: water, toluene, xylene, petroleum ether, vegetable oils, acetone, methyl ethyl ketone, cyclohexanone, acid anhydrides, acetonitrile, acetophenone, amyl acetate, 2-butanone, butylene carbonate, chlorobenzene, cyclohexane, cyclohexanol, alkyl esters of acetic acid, diacetone alcohol, 1,2-dichloropropane, diethanolamine, p-diethylbenzene, diethylene glycol, diethylene glycol abiet, diethylene glycol butyl ether, diethylene glycol ethyl ether, diethylene glycol methyl ether, N,N-dimethylformamide, dimethyl sulfoxide, 1,4-dioxane, dipropylene glycol, dipropylene glycol methyl ether, dipropylene glycol dibenzoate, diproxitol, alkylpyrrolidone, ethyl acetate, 2-ethylhexanol, ethylene carbonate, 1,1,1-Trichloroethane, 2-heptanone, α-pinene, d-limonene, ethyl lactate, ethylene glycol, ethylene glycol butyl ether, ethylene glycol methyl ether, gamma-butyrolactone, glycerol, glycerol acetate, glycerol diacetate, glycerol triacetate, hexadecane, hexylene glycol, isoamyl acetate, isobornyl acetate, isooctane, isophorone, isopropyl benzene, isopropyl myristate, lactic acid, laurylamine, mesityl oxide, methoxypropanol, methyl isoamyl ketone, methyl isobutyl ketone, methyl laurate, methyl octanoate, methyl oleate, methylene chloride, m-xylene, n-hexane, n-octylamine, octadecanoic acid, octylamine acetate , oleic acid, oleylamine, o-xylene, phenol, polyethylene glycol, propionic acid, propyl lactate, propylene carbonate, propylene glycol, propylene glycol methyl ether, p-xylene, toluene, triethyl phosphate, triethylene glycol, xylene sulfonic acid, paraffin, mineral oil, trichloroethylene, perchloroethylene, ethyl acetate, amyl acetate, butyl acetate, propylene glycol methyl ether, diethylene glycol methyl ether, methanol, ethanol, isopropanol, and high molecular weight alcohols such as amyl alcohol, tetrahydrofurfuryl alcohol, hexanol, octanol, ethylene glycol, propylene glycol, glycerol, and N-methyl-2-pyrrolidone.

[0091] Suitable solid carriers are, for example, talc, titanium dioxide, pyroferritic clays, silica, attapulgite clays, diatomaceous earth, limestone, calcium carbonate, bentonite, calcium montmorillonite, cottonseed hulls, wheat flour, soybean flour, pumice, wood flour, walnut shell flour, lignin and similar substances.

[0092] Many surface-active substances can be advantageously used in both solid and liquid formulations, especially those that can be diluted with a carrier before use. The surface-active substances can be anionic, cationic, nonionic or polymeric and can also be used as emulsifying agents, wetting agents or suspending agents, or for other purposes. Typical surface-active substances are, for example, salts of alkyl sulfates, such as diethanolammonium lauryl sulfate; salts of alkylarylsulfonates, such as calcium dodecylbenzenesulfonate; alkylphenol / alkylene oxide adducts, such as nonylphenol ethoxylate; alcohol / alkylene oxide adducts, such as tridecyl alcohol ethoxylate; soaps, such as sodium stearate; salts of alkylnaphthalenesulfonates, such as sodium dibutylnaphthalenesulfonate; dialkyl esters of sulfosuccinate salts, such as sodium di(2-ethylhexyl)sulfosuccinate; sorbitol esters, such as sorbitol oleate; quaternary amines, such as lauryltrimethylammonium chloride, polyethylene glycol esters of fatty acids, such as polyethylene glycol stearate; block copolymers of ethylene oxide and propylene oxide; and salts of mono- and dialkyl phosphate esters; and also those disclosed, for example, in McCutcheon's Detergents and Emulsifiers Annual, MC Publishing. Corp., Ridgewood, New Jersey (1981).

[0093] Further adjuvants that can be used in pesticide formulations include crystallization control agents, viscosity modifiers, suspending agents, dyes, antioxidants, foaming agents, light absorbers, mixing aids, antifoaming agents, complexing agents, neutralizing or pH adjusting substances and buffers, corrosion inhibitors, fragrances, wetting agents, penetration aids, micronutrients, plasticizers, flow regulators, lubricants, dispersants, thickeners, antifreeze agents, fungicides and liquid and solid fertilizers.

[0094] The formulations according to the present invention may contain additives including oils of vegetable or animal origin, mineral oils, alkyl esters of such oils, or mixtures of such oils and oil derivatives. The amount of additive oil in the compositions according to the present invention is generally 0.01 to 10% based on the mixture to be applied. For example, the oil additive can be added to the spray tank at the desired concentration after the spray mixture has been prepared. Preferred additive oils include mineral oils or oils of vegetable origin, such as rapeseed oil, olive oil, or sunflower oil, emulsified vegetable oils, alkyl esters of vegetable-derived oils, such as methyl derivatives, or oils of animal origin, such as fish oil or beef tallow. Preferred oil additives are C8C 22 Alkyl esters of fatty acids, especially C 12 ~C 18 Methyl derivatives of fatty acids include, for example, the methyl esters of lauric acid, palmitic acid, and oleic acid (methyl laurate, methyl palmitate, and methyl oleate, respectively). Many oil derivatives are listed in the Compendium of Herbicide Adjuvants, 10 th Edition, Southern Illinois University, 2010.

[0095] The formulations generally contain 0.1 to 99% by weight, in particular 0.1 to 95% by weight, of compounds (A) and (B) and preferably 1 to 99.9% by weight of formulation adjuvants, including 0 to 25% by weight of surfactants. Commercial products may preferably be formulated as concentrates, but end users will usually use diluted formulations.

[0096] The application rates vary within wide limits and depend on the nature of the soil, the method of application, the crop plant, the pests to be controlled, the prevailing weather conditions and other factors which depend on the method, time of application and target crop. As a general guide, the compound should be applied at a rate of 1-2000 l / ha (1 x 10 -7 ~2×10 -4 m 3 / m 2 ), especially 10 to 1000 l / ha (1 × 10 -6 ~1×10 -4 m 3 / m2 ) may be applied.

[0097] A preferred formulation may have the following composition (% by weight): where the term "active ingredients" refers to the total weight % of the combination of all active ingredients in the composition.

[0098] Emulsifiable concentrate: Active ingredient: 1-95%, preferably 60-90% Surfactant: 1 to 30%, preferably 5 to 20% Liquid carrier: 1 to 80%, preferably 1 to 35%

[0099] Dust: Active ingredient: 0.1 to 10%, preferably 0.1 to 5% Solid carrier: 99.9 to 90%, preferably 99.9 to 99%

[0100] Suspension concentrate: Active ingredient: 5-75%, preferably 10-50% Water: 94-24%, preferably 88-30% Surfactant: 1 to 40%, preferably 2 to 30%

[0101] Wettable powder: Active ingredient: 0.5 to 90%, preferably 1 to 80% Surfactant: 0.5 to 20%, preferably 1 to 15% Solid carrier: 5 to 95%, preferably 15 to 90%

[0102] Granules: Active ingredient: 0.1 to 30%, preferably 0.1 to 15% Solid carrier: 99.5 to 70%, preferably 97 to 85%

[0103] Various aspects and embodiments of the invention will now be illustrated in more detail by way of example, it being understood that modifications of detail can be made without departing from the scope of the invention. [Example]

[0104] Formulation Examples

[0105] [Table 1]

[0106] The combination is thoroughly mixed with adjuvants and the mixture is thoroughly ground in a suitable mill to obtain a wettable powder that can be diluted with water to obtain a suspension of the desired concentration.

[0107] [Table 2]

[0108] The combination is thoroughly mixed with the adjuvant and the mixture is thoroughly ground in a suitable mill to obtain a powder that can be directly used for seed treatment.

[0109] emulsifiable concentrate Active ingredient 10% Octylphenol polyethylene glycol ether (ethylene oxide 4-5 mol) 3% Calcium dodecylbenzenesulfonate 3% Castor oil polyglycol ether (ethylene oxide 35 mol) 4% Cyclohexanone 30% Xylene mixture 50%

[0110] Emulsions of any required dilution that can be used for plant protection can be obtained from this concentrate by dilution with water.

[0111] [Table 3]

[0112] A ready-to-use dust is obtained by mixing the combination with a carrier and grinding the mixture in a suitable mill. Such dusts can also be used for dry dressing of seeds.

[0113] Extruded Granules Active ingredient 15% Sodium lignosulfonate 2% Carboxymethylcellulose 1% Kaolin 82%

[0114] The combination is mixed and ground with the adjuvant, the mixture is moistened with water, the mixture is extruded and then dried in a stream of air.

[0115] Coated granules Active ingredient 8% Polyethylene glycol (molecular weight 200) 3% Kaolin 89%

[0116] The finely ground combination is applied uniformly in a mixer to kaolin moistened with polyethylene glycol. Non-dusting coated granules are thus obtained.

[0117] Suspension concentrate Active ingredient 40% Propylene glycol 10% Nonylphenol polyethylene glycol ether (ethylene oxide 15 mol) 6% Sodium lignosulfonate 10% Carboxymethylcellulose 1% Silicone oil (in the form of a 75% emulsion in water) 1% water 32%

[0118] The finely divided combination is thoroughly mixed with adjuvants to obtain a suspension concentrate, from which suspensions of any desired dilution can be obtained by dilution with water, which can be used to treat and protect living plants and plant propagation material against microbial infestation by spraying, pouring, or dipping.

[0119] Flowable seed treatment Active ingredient 40% Propylene glycol 5% Copolymer butanol PO / EO 2% Tristyrene phenol + 10-20 moles EO 2% 1,2-Benzisothiazolin-3-one (in the form of a 20% aqueous solution) 0.5% Monoazo pigment calcium salt 5% Silicone oil (in the form of a 75% emulsion in water) 0.2% Water 45.3%

[0120] The finely divided combination is thoroughly mixed with adjuvants to obtain a suspension concentrate, from which suspensions of any desired dilution can be obtained by dilution with water, which can be used to treat and protect living plants and plant propagation material against microbial infestation by spraying, pouring, or dipping.

[0121] Sustained-release capsule suspension 28 parts of the combination are mixed with 2 parts of an aromatic solvent and 7 parts of a diisocyanate toluene / polymethylene-polyphenylisocyanate mixture (8:1). This mixture is emulsified in a mixture of 1.2 parts of polyvinyl alcohol, 0.05 parts of an antifoaming agent, and 51.6 parts of water until the desired particle size is reached. To this emulsion, a mixture of 2.8 parts of 1,6-diaminohexane in 5.3 parts of water is added. The mixture is stirred until the polymerization reaction is complete. The resulting capsule suspension is stabilized by the addition of 0.25 parts of a thickener and 3 parts of a dispersing agent. The capsule suspension formulation contains 28% active ingredient. The media capsule diameter is 8-15 micrometers. The resulting formulation is applied to seeds as an aqueous suspension in a device suitable for the purpose.

[0122] Biological Efficacy Testing Seeds of various test species were placed in pots (Digitaria sanguinalis (DIGSA), Echinochloa crus-galli (ECHCG), Setaria faberi (SETFA), Stellaria media (STEME), Amaranthus retroflexus (AMARE), Chenopodium album (CHEAL), Abutilon theophrasti (ABUTH), Ipomoea hederacea (IPOHE), Phalaris minor (PHAMI), Eleusine indica (ELEIN), Sorghum bicolor (SORVU), and Euphorbia japonica (EUPHORB)). Plants were sown in standard soil in a glasshouse (24 / 16°C, day / night; 14-hour light; 65% humidity) and grown under controlled conditions. The plants were sprayed with an aqueous spray solution derived from dissolving component (A) in acetone and IF50 (11.12% Emulsogen EL360™ + 44.44% N-methylpyrrolidone + 44.44% Dowanol DPM glycol ether), followed by dilution of component (B) to the required concentration using 0.2% Genapol XO80 (CAS No. 9043-30-5) in water. The test compounds or compositions were applied at the specified rate. The test plants were then grown in the greenhouse under controlled conditions (24 / 16°C, day / night; 14-hour light; 65% humidity) with watering twice daily. After 14 days the tests were rated for the percentage of damage caused to the plants (100 = total damage to the plants; 0 = no damage to the plants) and the results are shown in Tables B1 to B18 below.

[0123] [Table 4]

[0124] Table 5

[0125] Table 6

[0126] Table 7

[0127] Table 8

[0128] Table 9

[0129] Table 10

[0130] Table 11

[0131] Table 12

[0132] Table 13

[0133] Table 14

[0134] Table 15

[0135] Table 16

[0136] Table 17

[0137] Table 18

[0138] Table 19

[0139] Table 20

[0140] Table 21

Claims

1. (A) a herbicidally effective amount of a compound of formula (I): 【Chemistry 1】 (In the formula, R 1 is selected from hydrogen, chloro and fluoro; R 2 is selected from chloro and bromo; R 3 is CO 2 R 5 and CH 2 OR 6 is selected from R 4 is H, CH 3 - and CH 3 CH 2 - is selected from, R 5 is H, CH 3 -, CH 3 CH 2 -, CH 3 CH 2 CH 2 -, CH 3 CH 2 CH 2 CH 2 -, (CH 3 ) 2 CH-, (CH 3 ) 2 CHCH 2 -, (CH 3 ) 3 C-, CF 3 CH 2 -, allyl, propargyl, CH 3 OCH 2 CH 2 -, C 2 H 5 OCH 2 CH 2 -, CH 3 CO 2 CH 2 CH 2 - and tetrahydrofuranmethyl, R 6 is C 1 ~C 4 Alkylcarbonyl, cyclopropylcarbonyl and C 1 ~C 2 alkylsulfonyl) or an agrochemically acceptable salt thereof, Component (B) is glufosinate or L-glufosinate, or an agrochemically acceptable ester or salt thereof; Herbicidal compositions.

2. The compound of formula (I) has the formula (Ia): 【Chemistry 2】 2. The herbicidal composition of claim 1, wherein the compound is

3. 3. The herbicidal composition according to claim 1 or 2, wherein component (B) is glufosinate.

4. 3. The herbicidal composition according to claim 1 or 2, wherein the component (B) is L-glufosinate.

5. 5. The herbicidal composition according to any one of claims 1 to 4, wherein the weight ratio of component (A) to component (B) is from 1:1 to 1:

50.

6. 6. The herbicidal composition according to any one of claims 1 to 5, wherein the weight ratio of component (A) to component (B) is from 1:4 to 1:

16.

7. 7. The herbicidal composition of any one of claims 1 to 6, further comprising at least one additional pesticide.

8. 8. The herbicidal composition of claim 7, wherein the additional pesticide is a herbicide or a herbicide safener.

9. 9. The herbicide composition of claim 8, wherein the herbicide is selected from the group consisting of paraquat dibromide, diquat dibromide, saflufenacil, trifludimoxazine thiafenacil, pyroxasulfone, S-metolachlor, glufosinate, L-glufosinate, glyphosate, mesotrione, metribuzin, and [3-(2-methoxy-4-prop-1-ynyl-phenyl)-4-oxo-2-bicyclo[3.2.1]oct-2-enyl]methyl carbonate.

10. 9. The herbicide composition of claim 8, wherein the herbicide safener is selected from the group consisting of benoxacor, cloquintocet, cyprosulfamide, dichlormid, fenchlorazole, fenclorim, fluxofenim, furilazole, isoxadifen, mefenpyr, metcamifen, and oxabetrinil.

11. 11. A method for controlling weeds in a locus, the method comprising the step of applying to said locus of weeds a controlling amount of a herbicidal composition according to any one of claims 1 to 10.

12. 11. A method for selectively controlling weeds in a habitat containing crop plants and weeds, the method comprising the step of applying to the weeds in the habitat a control amount of a herbicide composition according to any one of claims 1 to 10.

13. 13. The method according to claim 12, wherein the weeds are PPO-resistant weeds that are resistant to at least one PPO-inhibiting herbicide other than the compound of formula (I).

14. 14. The method of claim 13, wherein the PPO-resistant weed has a mutation at amino acid position 98, amino acid position 210, amino acid position 361, and / or amino acid position 399 in a gene encoding the protoporphyrinogen oxidase enzyme.

15. Use of a composition according to any one of claims 1 to 10 on crops which are tolerant to PPO-inhibiting herbicides.

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