Herbicidal components

Abstract

The present invention relates to a herbicidal composition comprising as active ingredients a mixture of components (A) and (B), wherein component (A) is a compound of formula (I): [Case 1] JPEG2026502851000020.jpg38161, and component (B) is bicyclopyrone or an agrochemically acceptable ester or salt thereof.

Description

[Technical Field]

[0001] The present invention relates to novel herbicidal combinations and their use in controlling plants or inhibiting plant growth. In particular, the herbicidal combinations of the present invention comprise as active ingredients a mixture of components (A) and (B), wherein component (A) is a compound of formula (I) and component (B) is bicyclopyrone. [Background technology]

[0002] WO 2016 / 095768 discloses herbicide compounds of formula (I) and processes for their preparation. Furthermore, WO 2020 / 063613 provides further processes for the preparation of such compounds. WO 2001 / 094339 describes bicyclopyrone and processes for its preparation. Summary of the Invention [Problem to be solved by the invention]

[0003] The present invention aims to provide alternative and / or improved herbicidal mixtures that are highly effective (especially at low doses) against a variety of weed species, and is based on the finding that compound (A) in combination with bicyclopyrone is particularly effective in controlling weeds. [Means for solving the problem]

[0004] In a first aspect of the present invention there is provided a herbicidal composition comprising as active ingredients a mixture of components (A) and (B), wherein component (A) is 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 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; and component (B) is bicyclopyrone or an agrochemically acceptable ester or salt thereof.

[0005] 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 3 is CO2R 5 and; R 4 is selected from H, CH— and CHCH—; preferably R 4 is CH3-; R 5 is H, CH3-, CH2CH3-, CH3CH2CH2-, CH3CH2CH2CH2-, (CH3)2CH - , (CH3)2CHCH2- and (CH3)3C-; preferably R 5 is CH2CH3-.

[0006] In a more preferred embodiment of the present invention, component (A) is of formula (Ia) [ka] is a compound of

[0007] In a preferred composition according to the present invention, the weight ratio of component (A) to component (B) is 20:1 to 1:20.

[0008] In more preferred compositions according to the present invention, the weight ratio of component (A) to component (B) is from 6:1 to 1:10.

[0009] In the most preferred compositions according to the present invention, the weight ratio of component (A) to component (B) is from 4:1 to 1:8.

[0010] In a second aspect of the invention there is provided a herbicidal composition according to the invention further comprising at least one additional pesticide.

[0011] In preferred compositions according to the second aspect of the invention, the additional pesticide is a herbicide or a herbicide safener.

[0012] 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, 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.

[0013] 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.

[0014] In a third aspect of the invention there is provided a method of controlling weeds in a locus which comprises applying to the locus of the weeds a control amount of a composition of the invention.

[0015] In a fourth aspect of the present invention there is provided a method for selectively controlling weeds in a habitat comprising crop plants and weeds, the method comprising the step of applying to the weeds in the habitat a control amount of a composition according to the present invention.

[0016] In another aspect, there is provided a method for controlling the growth of protoporphyrinogen IX oxidase (PPO) inhibitor herbicide-resistant weeds, the method comprising the step of applying to the weeds, parts of the weeds, weed propagation material, or locus of the weeds an effective amount of a composition of 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).

[0017] In another aspect, there is provided a method for controlling the growth of PPO-resistant weeds, the method comprising the step of applying to weeds, parts of weeds, weed propagation material, or a habitat of the weeds an effective amount of a composition of 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.

[0018] In another aspect, there is provided a method for controlling the growth of PPO-resistant weeds, the method comprising the step of applying to weeds, parts of weeds, weed propagation material, or a locus of the weeds an effective amount of a composition of the present 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.

[0019] In a preferred method according to the fourth aspect of the present invention, the weeds are selected from the group consisting of Alopecurus sp., 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. The species includes species selected from the group consisting of Sorghum sp., Sorghum sp., Conyza sp., and Lolium sp.

[0020] In a more preferred method according to the fourth aspect of the present 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.), Conyza sp., and Lolium sp.

[0021] Preferably, the weeds include species selected from Alopecurus sp., Amaranthus sp., Conyza sp., Echinochloa sp., Lolium sp. and Setaria sp. DETAILED DESCRIPTION OF THE INVENTION

[0022] 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, pp. 20-22; 1967): ppm = mg / L of active ingredient (ai) X = % effect of the first active ingredient using p ppm of active ingredient Y = % effect of the second active ingredient using q ppm of active ingredient.

[0023] According to Colby, the predicted effect of active ingredients A+B using p+q ppm of active ingredients is given by the following formula:

number

[0024] If the actual observed effect (O) is greater than the predicted effect E, the effect of the combination is supra-additive, i.e., synergistic. Mathematically, synergy corresponds to a positive value of the difference (OE). In the case of a purely complementary addition of activity (predicted activity), the difference (OE) is 0. A negative value of the difference (OE) indicates a loss of activity compared to the predicted activity.

[0025] 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.

[0026] The combinations of the present invention may also provide an expanded spectrum of activity compared to the activity provided by each individual component to mediate effective herbicidal activity and / or may allow the use of lower rates of the individual components when used in combination than when used alone.

[0027] Furthermore, the compositions of the present invention may potentially exhibit increased crop resistance when compared to the effect of compound A alone. This occurs when the action of the combination of active ingredients causes less damage to useful crops than the action of one of the active ingredients alone.

[0028] Compound (A) of formula (Ia) is referred to in WO 2016 / 095768 as compound 6. It can be prepared according to Example 1 of WO 2016 / 095768.

[0029] 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. "C1-C3 alkyl" and "C1-C2 alkyl" should be construed accordingly.

[0030] As used herein, the term "C1-C4 alkylcarbonyl" refers to a group of the formula -C(O)R a where R a refers to a C1-C4 alkyl group as generally defined above. Examples of C1-C4 alkylcarbonyl include, but are not limited to, acetyl.

[0031] As used herein, the term "C1-C4 alkylsulfonyl" refers to a group of the formula -S(O)R a where R a is a C1-C4 alkyl group as generally defined above). The terms "C1-C3 alkylsulfonyl" and "C1-C2 alkylsulfonyl" should be construed accordingly. Examples of C1-C4 alkylsulfonyl include, but are not limited to, methylsulfonyl.

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

[0033] As used herein, the term "herbicide" refers to a compound that inhibits 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 an inhibiting or modifying effect on plant growth. Inhibiting or modifying effects include any deviation from natural occurrence, such as death, delay, leaf scorch, chlorosis, dwarfism, etc.

[0034] The term "control" means to kill, reduce or retard growth, or prevent or reduce germination. Generally, the plants to be controlled are unwanted plants (weeds).

[0035] As used herein, the term "site" means the field in which plants are growing or where seeds of cultivated plants are sown or where seeds will be placed in the soil, including the soil, seeds and seedlings, and established vegetation.

[0036] The term "plant" refers to all physical parts of a plant, including seeds, seedlings, saplings, roots, tubers, stems, stalks, leaves and fruits.

[0037] The term "plant propagation material" refers to all reproductive parts of plants, such as seeds or vegetative parts of plants, such as cuttings and tubers. This includes seeds in the strict sense as well as roots, fruits, tubers, bulbs, rhizomes and plant parts.

[0038] 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 crops from herbicide injury but does not prevent the herbicide from killing weeds.

[0039] Crops of useful plants in which the compositions according to the invention can be used include perennial and annual crops, for example berry plants, such as blackberries, blueberries, cranberries, raspberries and strawberries; cereals, such as barley, 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. herbs such as basil, borage, chives, coriander, lavender, lovage, mint, oregano, parsley, rosemary, sage, thyme; legumes such as beans, lentils, peas and soybeans; nuts such as almonds, cashews, crushed nuts, hazelnuts, peanuts, pecans, pistachios and walnuts; palms such as oil 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, mallow, melon, okra, onion, pepper, potato, pumpkin, rhubarb, spinach and tomato; grapes such as grapes.

[0040] Preferably, the compositions of the present invention are used to control weeds in oil palm, corn, cereals or soybeans.

[0041] Crops are understood to be those occurring in nature, those obtained by traditional breeding methods or those obtained by genetic engineering, including crops that contain so-called output traits (e.g. improved storage stability, higher nutritional value and improved flavor).

[0042] Crops should also be understood to include crops that have been made resistant to herbicides or classes of herbicides (e.g., ALS inhibitors, GS inhibitors, EPSPS inhibitors, PPO inhibitors, ACCase inhibitors, and HPPD inhibitors) by conventional breeding methods or genetic engineering. An example of a crop that has been made resistant to imidazolinones, such as imazamox, by conventional breeding methods is Clearfield® summer rapeseed (canola). Examples of crops that have been made resistant to herbicides by genetic engineering methods include, for example, glyphosate-resistant and glufosinate-resistant corn varieties commercially available under the trade names RoundupReady® and LibertyLink®.

[0043] Crops also include those that have been genetically engineered to resist harmful insects, such as Bt corn (resistant to the European corn borer), Bt cotton (resistant to the boll weevil), and Bt potato (resistant to the Colorado 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 transgenic 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 insecticidal resistance and expressing one or more toxins include 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 tolerant to glyphosate and capable of expressing an insecticidal Cry3 protein.

[0044] Thus, crop plants can be made tolerant to PPO-inhibitors by genetic engineering. Examples of crops that have been made tolerant to PPO-inhibiting herbicides by genetic engineering are known in the art, for example, as described in WO 95 / 34659. Thus, in an even more preferred embodiment, the crop plant has been genetically modified with a polynucleotide comprising a DNA sequence encoding a PPO-inhibitor-resistant enzyme.

[0045] Examples of crops 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] In another embodiment, there is provided the use of the composition of claim 1 on crop plants that are resistant to PPO-inhibiting herbicides.

[0047] In another embodiment, there is provided the use of the composition of claim 1 on crop plants that are resistant to compounds of formula (I).

[0048] For the avoidance of doubt, the use of a composition according to claim 1 on crop plants refers to the application of the composition both pre- and / or post-emergence of the crop plants.

[0049] In another embodiment, there is provided a method for controlling unwanted vegetation in the vicinity of a crop plant resistant to a PPO-inhibiting herbicide, the method comprising applying to the unwanted vegetation and plants or their habitat an effective amount of the composition of claim 1. In such an embodiment, the crop plant is preferably selected from oil palm, corn, cereals, or soybeans.

[0050] 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. (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).

[0051] 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., Conyza sp. It is used to control Lolium sp. and Lolium sp.

[0052] More preferably, the compositions of the present invention are used to control Echinochloa sp., Conyza sp. and Amaranthus sp.

[0053] In all aspects of the invention, in any particular embodiment, for example, the weeds to be controlled and / or stunted may be monocotyledonous or dicotyledonous weeds that are tolerant or resistant to one or more other herbicides, for example, HPPD inhibitor herbicides such as mesotrione, PSII inhibitor herbicides such as atrazine, or EPSPS inhibitors such as glyphosate. Such weeds include, but are not limited to, resistant Amaranthus biotypes.

[0054] The compositions of the present invention can also be mixed with one or more additional pesticides including herbicides (typically different from the herbicides / components (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 which provide an even broader range of agricultural protection.

[0055] Preferred herbicides as additional mixing partners are acetochlor, acifluorfen (including acifluorfen-sodium), aclonifen, ametryn, aminocarbazone, aminopyralid, aminotriazole, atrazine, beflubutamid-M, benquitrione, bensulfuron (including bensulfuron-methyl), bentazon, bicyclopyrone, vilanaphos, bipyrazone, bispyribac-sodium, bixlozone, broclozone, bromacil, bromoxynil, butachlor, butafenacil, carfentrazone (carfentrazone-e), chlorantil), cloransulam (including cloransulam-methyl), chlorimuron (including chlorimuron-ethyl), chlorotoluron, chlorsulfuron, cinmethylin, clasifos, clethodim, clodinafop (including clodinafop-propargyl), clomazone, clopyralid, cyclopyranyl, cyclopyrimorate, cyclosulfamuron, cyhalofop (including cyhalofop-butyl), 2,4-D (including choline salts and their 2-ethylhexyl esters), 2,4-DB, desmedipham, dicamba (aluminum, aminopropyl, bi s-aminopropylmethyl, choline, dichloroprop, diglycolamine, dimethylamine, dimethylammonium, and their potassium and sodium salts) diclosulam, difluhenican, diflufenzopyr, dimethachlor, dimethenamid-P, dioxopyritrio, diquat dibromide, diuron, epirifenacil, ethalfluralin, ethofumesate, fenoxaprop (including fenoxaprop-P-ethyl), fenoxasulfone, fenpyrazone, fenquinotrione, fentrazamide, flazasulfuron, florasulam, Florpyrauxifen (including florpyrauxifen-benzyl), fluazifop (including fluazifop-p-butyl), flucarbazone (including flucarbazone-sodium), fluchloraminopyr (including fluchloraminopyr-tefuryl), flufenacet, flufenoximacil, flumetsulam, flumioxazin, fluometuron, fomesafen, flupyrsulfuron (including flupyrsulfuron-methyl-sodium), fluroxypyr (including fluroxypyr-meptyl), flusulfinam, fomesafen, foramsulfuron,Glufosinate (including L-glufosinate and ammonium salts of both), glyphosate (including diammonium, isopropylammonium and their potassium salts), halaxifen (including haloxyfop-methyl), haloxyfop (including haloxyfop-methyl), hexazinone, hydantocidin, icaforin (including icaforin-methyl), imazamox (including R-imazamox), imazapic, imazapyr, imazethapyr, indaziflam, indoloxypyr (including indoloxypyr-cyanomethyl), iodosul Furoin (including iodosulfuron-methyl-sodium), 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, oxy Fluorfen, paraquat dichloride, pendimethalin, penoxsulam, phenmedipham, picloram, pinoxaden, pretilachlor, primisulfuron-methyl, prometryn, propanil, propaquizafop, propysulfuron, propyzamide, prosulfocarb, prosulfuron, pyraclonil, pyraflufen (including pyraflufen-ethyl), pyraquinate, pyrasulfotole, pyridate, pyriftalid, pyriflubenzoxim, pyrimisulfan, pyroxasulfone, pyroxsulam, quinclorac, quinme Lac, quizalofop (including quizalofop-P-ethyl and quizalofop-P-tefuryl), rimisoxafen, rimsulfuron, saflufenacil, sethoxydim, simazine, S-metalochlor, sulfentrazone, sulfosulfuron, tebuthiuron, tefuryltrione, tembotrione, terbuthylazine, terbutryn, tetflupyrrolimet, thiencarbazone, thifensulfuron, thiafenacil, tolpyralate, topramezone, tralkoxydim, triafamone, triallate, 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-butylisoxazol-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-fu 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-cyclopenta[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.

[0056] Herbicides more preferred 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, glufosinate, L-glufosinate, glyphosate, indaziflam, isoxaflutole, metribuzin, mesosulfuron, mesotrione, S-metolachlor, pendimethalin, prometryne, 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, glufosinate, L-glufosinate, glyphosate, isoxaflutole, metribuzin, benzophenone, benzophenone-1, benzophenone-2, benzophenone-3, benzophenone-4, benzophenone-5, benzophenone-6, benzophenone-7, benzophenone-8, benzophenone-9, 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, and thiafenacil, ...The most preferred herbicides are selected from the group consisting of paraquat dibromide, diquat dibromide, saflufenacil, trifludimoxadine, 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.

[0057] 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, dietholate, fenchlorazole (including fenchlorazole-ethyl), fenclorim, flurazole, fluxofenim, furilazole, furilasome, isoxadifen (including isoxadifen-ethyl), mefenpyr (including mefenpyr-diethyl), mephenate, metcamifenoxabetrinil, 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, 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, and a reference to fenchlorazole-ethyl also applies to fenchlorazole, etc.

[0058] The compositions of the present invention can be applied before or after planting of the crop, before weeds appear (pre-emergence application) or after weeds appear (post-emergence application).When a safener is combined with the mixture of the present invention, the mixing ratio of component (A) to safener is preferably 100:1 to 1:10, preferably 20:1 to 1:1.

[0059] The safener and the composition of the present invention can be applied simultaneously. For example, the safener and the composition of the present invention can be applied to the pre-emergence site or to the crop after emergence. The safener and the composition of the present invention can also be applied sequentially. For example, the safener can be applied before sowing the seeds as a seed treatment, or the composition of the present invention can be applied to the pre-emergence site or to the crop after emergence.

[0060] However, those skilled in the art will appreciate that the compositions of the present invention are particularly useful in non-selective burndown applications and therefore may also be used to control volunteer plants or avoid crop plants, and in such situations it will be apparent that the inclusion of a safener in the compositions of the present invention is not necessary.

[0061] The weight ratio of any two components in each combination is selected to achieve a desired, e.g., synergistic, effect. Typically, the weight ratio will vary depending on the specific components and the number of components present in the combination. Generally, the weight ratio between any two components in any combination of the present invention, independently of one another, is between 100:1 and 1:100, and is preferably between 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, 84:19, 85:20, 85:21, 85:22, 85:23, 85:24, 85:25, 85:26, 85:27, 85:28, 85:29, 86:30, 86:31, 86:32, 86:33, 86:34, 86:35, 86:36, 86:37, 86:38, 86:39, 86:40, 86:41, 86:42, 86:43, 86:44, 86:45, 86:46, 86:47, 86:48, 86:49, 86:50, 86:51, 86:52, 86:53, 86:54, 86:55, 86:56, 86:57, 86:58, 86:59, 86:59, 86:59, , 81:19, 80:20, 79:21, 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, 55:4 5, 54:46, 53:47, 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 1:72, 27:73, 26:74, 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, up to 1:99. Preferred weight ratios between any two components of the present invention are from 75:1 to 1:75, more preferably from 50:1 to 1:50, in particular from 20:1 to 1:20, advantageously from 10:1 to 1:10, such as from 6:1 to 1:10, for example from 4:1 to 1:8 or from 1:2 to 1:8. Mixing ratios are understood to include, on the one hand, mass ratios and, on the other hand, molar ratios.

[0062] In a preferred composition of the present invention, component (A) is a compound of formula (Ia) or an agrochemically acceptable salt thereof, and component (B) is bicyclopyrone, wherein the weight ratio of component (A) to component (B) is 20:1 to 1:20.

[0063] In a more preferred composition of the present invention, component (A) is a compound of formula (Ia) or an agrochemically acceptable salt thereof, and component (B) is bicyclopyrone, wherein the weight ratio of component (A) to component (B) is 6:1 to 1:10.

[0064] In the most preferred compositions of the present invention, component (A) is a compound of formula (Ia) or an agrochemically acceptable salt thereof, and component (B) is bicyclopyrone, wherein the weight ratio of component (A) to component (B) is 4:1 to 1:8.

[0065] In another embodiment, there is provided a composition wherein component (A) is a compound of formula (Ia) or an agronomically acceptable salt thereof, and component (B) is bicyclopyrone, wherein the weight ratio of component (A) to component (B) is from 4:1 to 1:8, and the weeds to be treated are selected from barnyard grass (Echinochloa crus-galli), artemisia kamchatka (Conyza canadensis), palmatum (Amaranthus palmeri), Alopecurus myosuroides, ryegrass (Lolium perenne), and foxtail (Setaria faberi).

[0066] In another embodiment, there is provided a composition wherein component (A) is a compound of formula (Ia) or an agronomically acceptable salt thereof, and component (B) is bicyclopyrone, wherein the weight ratio of component (A) to component (B) is 1:2 to 1:8 (particularly, the weight ratio of component (A) to component (B) is 1:2, 1:4, or 1:8), and the weeds to be treated are barnyardgrass (Echinochloa crus-galli) or palmatum (Amaranthus palmeri).

[0067] In another embodiment, there is provided a composition wherein component (A) is a compound of formula (Ia) or an agrochemically acceptable salt thereof, and component (B) is bicyclopyrone, wherein the weight ratio of component (A) to component (B) is 1:4 to 1:8, and the weed to be treated is Conyza canadensis.

[0068] In another embodiment, there is provided a composition wherein component (A) is a compound of formula (Ia) or an agrochemically acceptable salt thereof, and component (B) is bicyclopyrone, wherein the weight ratio of component (A) to component (B) is 4:1 to 1:1 (particularly, the weight ratio of component (A) to component (B) is 4:1, 2:1 or 1:1), and the weeds to be treated are Alopecurus myosuroides or Lolium perenne.

[0069] In another embodiment, there is provided a composition wherein component (A) is a compound of formula (Ia) or an agronomically acceptable salt thereof, and component (B) is bicyclopyrone, wherein the weight ratio of component (A) to component (B) is 1:1, and the weed to be treated is foxtail (Setaria faberi).

[0070] 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.

[0071] 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.

[0072] The amount of the composition according to the invention to be applied depends on various factors, such as the compound used, the object of treatment, e.g., plants, soil or seeds, the type of treatment, e.g., spraying, dusting or seed dressing, or the time of application. In agricultural practice, the application rate of the composition according to the invention depends on the type of effect desired and is typically about 1 hectare (10,000 m 2 The range is 35 to 4000 g of total composition per hectare, more usually 35 to 2000 g / ha. Application is generally by spraying the composition, typically over a wide area with a tractor-mounted sprayer, although other methods such as dusting (for dusts), dripping or drench can also be used.

[0073] The compositions of the present invention can be advantageously used in the following formulations (where "active ingredient" refers to the respective mixture of the compounds of component (A) and component (B) or, if a safener is also used, the respective mixture of the compounds of component (A) and component (B) and the safener):

[0074] The individual components of the compositions of the present invention may be utilized as technical active ingredients during production. However, more typically, compositions according to the present invention may be formulated in various ways using formulation auxiliaries such as carriers, solvents, and surfactants. The formulations may be in various physical forms, such as powders, gels, wettable powders, water-dispersible granules, water-dispersible tablets, effervescent pellets, emulsifiable concentrates, microemulsions, oil-in-water emulsions, oil flowables, water dispersions, oil dispersions, suspoemulsions, capsule suspensions, emulsifiable granules, soluble liquids, water-soluble concentrates (using water or a water-miscible organic solvent as a carrier), impregnated polymer film forms, or other forms known from, for example, the Manual on Development and Use of FAO and WHO Specifications for Pesticides, United Nations, First Edition, Second Revision (2010). Such formulations may be used directly or diluted before use. Dilution may be carried out, for example, with water, liquid fertilizers, micronutrients, biological materials, oils, or solvents.

[0075] 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.

[0076] The active ingredient can also be contained in very fine microcapsules. Microcapsules contain the active ingredient in a porous carrier, allowing for controlled (e.g., sustained) release of the active ingredient into the environment. Microcapsules typically have diameters of 0.1 to 500 microns. They contain the active ingredient in an amount of approximately 25 to 95% by weight of the capsule. The active ingredient can be in the form of a monolithic solid, in the form of microparticles 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, including 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 finely divided particles in a solid matrix of a base material, but the microcapsules themselves are not encapsulated.

[0077] Formulation adjuvants suitable for preparing the compositions according to the invention are known per se. Liquid carriers 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, 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 ... Leic 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 may be used.

[0078] Suitable solid carriers are, for example, talc, titanium dioxide, pyrophyllite clay, silica, attapulgite clay, diatomaceous earth, limestone, calcium carbonate, bentonite, calcium montmorillonite, cottonseed hulls, wheat flour, soybean flour, pumice, wood flour, ground walnut shells, lignin and similar materials.

[0079] Many surfactants can be advantageously used in both solid and liquid formulations, especially those that can be diluted with a carrier before use. The surfactants can be anionic, cationic, nonionic or polymeric and can be used as emulsifying agents, wetting agents or suspending agents, or for other purposes. Typical surfactants include, for example, salts of alkyl sulfates, such as diethanolammonium lauryl sulfate; alkylaryl sulfonates, such as calcium dodecylbenzene sulfonate; alkylphenol / alkylene oxide adducts, such as nonylphenol ethoxylate; alcohol / alkylene oxide adducts, such as tridecyl alcohol ethoxylate; soaps, such as sodium stearate; alkylnaphthalene sulfonates, such as sodium dibutylnaphthalene sulfonate; dialkyl esters of sulfosuccinates, 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 di-alkyl phosphate esters; and salts of mono- and di-alkyl phosphate esters, as well as ... Further substances are mentioned in Jersey (1981).

[0080] Further adjuvants that may be used in pesticide formulations include crystallization inhibitors, 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, uptake promoters, micronutrients, plasticizers, glidants, lubricants, dispersants, thickeners, antifreeze agents, fungicides and liquid and solid fertilizers.

[0081] The formulations according to the present invention may contain additives including vegetable or animal-derived oils, mineral oils, alkyl esters of such oils, or mixtures of such oils with oil derivatives. The amount of oil additive 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 is prepared. Preferred oil additives include mineral oils or oils of vegetable origin, such as rapeseed oil, olive oil, or sunflower oil, emulsified vegetable oils, alkyl esters of vegetable oils, such as methyl derivatives, or oils of animal origin, such as fish oil or beef tallow. Preferred oil additives include 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.

[0082] The formulations generally contain 0.1 to 99% by weight, in particular 0.1 to 95% by weight, of compounds (A) and (B) and 1 to 99.9% by weight of formulation adjuvants, preferably including 0 to 25% by weight of surfactants. Commercial products may preferably be formulated as concentrates, but end users usually use diluted formulations.

[0083] 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 climatic conditions and other factors governed by the method, time of application and target crop. As a general guideline, 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 / m 2) can be applied at a rate of

[0084] 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.

[0085] emulsion: Active ingredient: 1-95%, preferably 60-90% Surfactant: 1 to 30%, preferably 5 to 20% Liquid carrier: 1 to 80%, preferably 1 to 35%

[0086] Powder: Active ingredient: 0.1 to 10%, preferably 0.1 to 5% Solid carrier: 99.9 to 90%, preferably 99.9 to 99%

[0087] Suspension concentrate: Active ingredient: 5-75%, preferably 10-50% Water: 94-24%, preferably 88-30% Surfactant: 1 to 40%, preferably 2 to 30%

[0088] 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%

[0089] Granules: Active ingredient: 0.1 to 30%, preferably 0.1 to 15% Solid carrier: 99.5 to 70%, preferably 97 to 85%

[0090] Various aspects and embodiments of the invention will now be described in more detail by way of example, it being understood that modifications of detail may be made without departing from the scope of the invention. [Example]

[0091] Combination example [Table 1]

[0092] 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.

[0093] [Table 2]

[0094] 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.

[0095] [Table 3]

[0096] Emulsions of any required dilution that can be used for plant protection can be obtained from this concentrate by dilution with water.

[0097] [Table 4]

[0098] A ready-to-use dust is obtained by mixing the combination with a carrier and grinding the mixture in a suitable mill. Such a dust can also be used for dry seed dressing.

[0099] [Table 5]

[0100] The combination is mixed and ground with the adjuvants, the mixture is moistened with water, the mixture is extruded and then dried in a stream of air.

[0101] [Table 6]

[0102] The finely ground combination is applied uniformly in a mixer to kaolin moistened with polyethylene glycol, thereby obtaining coated granules that do not generate dust.

[0103] [Table 7]

[0104] 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 diluting with water, and such dilutions can be used to treat and protect living plants and plant propagation material against microbial infestation by spraying, pouring, or dipping.

[0105] [Table 8]

[0106] The finely ground combination can be thoroughly mixed with an adjuvant to give a suspension concentrate from which suspensions of any desired dilution can be obtained by dilution with water. Such dilutions can be used to treat living plants and plant propagation material by spraying, pouring, or immersion to protect them from microbial infestation.

[0107] Sustained-release capsule suspension 28 parts of the combination are mixed with 2 parts aromatic solvent and 7 parts toluene diisocyanate / polymethylene-polyphenylisocyanate (8:1) mixture. This mixture is emulsified in a mixture of 1.2 parts polyvinyl alcohol, 0.05 parts antifoaming agent, and 51.6 parts water until the desired particle size is achieved. A mixture of 2.8 parts 1,6-diaminohexane in 5.3 parts water is added to this emulsion. The mixture is stirred until the polymerization reaction is complete. The resulting capsule suspension is stabilized with the addition of 0.25 parts thickener and 3 parts dispersant. The capsule suspension formulation contains 28% active ingredient. The media capsule diameter is 8-15 microns. The resulting formulation is applied to seeds as an aqueous suspension in a device suitable for that purpose.

[0108] Biological Potency Testing Seeds of various test species (Echinochloa crus-galli (ECHCG), Conyza canadensis (ERICA), Amaranthus palmeri (AMAPA), Alopecurus myosuroides (ALOMY), Lolium perenne (LOLPE), and Setaria faberi (SETFA)) were sown in standard soil in pots and grown under controlled conditions in a greenhouse (24 / 16°C, day / night; 14 hours light; 65% humidity) using a mixture of acetone and IF50 (11.12% Emulsogen EL360™ + 44.44% N-methylpyrrolidone + 44.44% Dowanol). The plants are sprayed with an aqueous spray solution obtained by dissolving the test compound or composition in 0.2% Genapol XO80 (CAS No. 9043-30-5) in water as a diluent and then diluting to the required concentration using 0.2% Genapol XO80 (CAS No. 9043-30-5) in water as a diluent. The test compound or composition is applied at the specified rate. The test plants are then grown in a greenhouse under controlled conditions (24 / 16°C, day / night; 14 hours of light; 65% humidity) and watered twice daily. After 14 days, the test is evaluated 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 B6 below.

[0109] [Table 9]

[0110] [Table 10]

[0111] [Table 11]

[0112] [Table 12]

[0113] Table 13

[0114] Table 14

Claims

1. A herbicidal composition comprising a mixture of components (A) and (B) as active ingredients, wherein component (A) is 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 Selected from: R 4 is H, CH 3 - and CH 3 CH 2 - 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; and component (B) is bicyclopyrone or an agrochemically acceptable ester or salt thereof.

2. R 1 is fluoro; R 2 is chloro; R 3 is CO 2 R 5 and R 4 is CH 3 - and R 5 is CH 3 CH 2 -is, The herbicidal composition according to claim 1.

3. 3. The herbicidal composition according to claim 1 or claim 2, wherein the weight ratio of component (A) to component (B) is from 20:1 to 1:

20.

4. 4. The herbicidal composition according to any one of claims 1 to 3, wherein the weight ratio of component (A) to component (B) is from 6:1 to 1:

10.

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 4:1 to 1:

8.

6. 6. The herbicidal composition of any one of claims 1 to 5, further comprising at least one additional pesticide.

7. 7. The herbicidal composition of claim 6, wherein the additional pesticide is a herbicide or a herbicide safener.

8. 8. The herbicidal composition according to claim 7, 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.

9. 8. The herbicidal composition of claim 7, wherein the herbicide safener is selected from the group consisting of benoxacor, cloquintocet, cyprosulfamide, dichlormid, fenchlorazole, fenclorim, fluxofenim, furilazole, isoxadifen, mefenpyr, metcamifen, and oxabetrinil.

10. 10. 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 9.

11. 10. A method for selectively controlling weeds in a habitat comprising crop plants and weeds, the method comprising the step of applying to the habitat weeds a control amount of a herbicidal composition according to any one of claims 1 to 9.

12. 12. The method according to claim 11, wherein the weeds are PPO-resistant weeds that are resistant to at least one PPO-inhibiting herbicide other than the compound of formula (I).

13. 13. The method of claim 12, 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.

14. 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., and Digitalia sp. sp.), Echinochloa sp., Setaria sp., Sorghum sp., Conyza sp., and Lolium sp.

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