Weeding composition

Abstract

The present invention relates to a herbicidal composition comprising (A) a herbicidally effective amount of a compound of formula (I) or an agrochemically acceptable ester or salt thereof; and (B) glufosinate-ammonium or L-glufosinate-ammonium.

Description

[0001] The present invention relates to novel herbicidal compositions comprising a combination of herbicidally active ingredients, which provide control of weeds in crops of useful plants. The invention further provides methods for controlling weeds in crops of useful plants, and the use of the herbicidal compositions for controlling weeds.

[0002] Compounds having formula (I)

[0003]

[0004] Known from WO 2016 / 095768 and provide effective control of problematic weeds in crops. WO 2020 / 063613 provides methods for further preparing such compounds.

[0005] Combinations of herbicidal active ingredients are commonly used in agriculture to increase and / or expand the control of problem plants (weeds) in crops of useful plants. In some cases, the combination can produce valuable effects greater than additive (synergistic), for example, effective weed control can be achieved at lower application rates. The present invention is based on novel compositions comprising compounds of formula (I).

[0006] Therefore, according to the present invention, there is provided a herbicidal composition comprising (A) a herbicidally effective amount of a compound having the formula (I):

[0007]

[0008] in

[0009] R 1 is selected from hydrogen, chlorine and fluorine;

[0010] R 2 selected from chlorine and bromine;

[0011] R 3 Selected from CO2R 5 and CH2OR 6 ;

[0012] R 4 is selected from H, CH3- and CH3CH2-;

[0013] R 5 Selected from H, CH3-, CH3CH2-, CH3CH2CH2-, CH3CH2CH2CH2-, (CH3)2CH-, (CH3)2CHCH2-, (CH3)3C-, CF3CH2-, allyl, propargyl, CH3OCH2CH2-, C2H5OCH2CH2-, CH3CO2CH2CH2- and tetrahydrofurylmethyl;

[0014] R6 is selected from C1-C4 alkylcarbonyl, cyclopropylcarbonyl and C1-C2 alkylsulfonyl;

[0015] or an agrochemically acceptable salt thereof; and

[0016] Component (B) is glufosinate or L-glufosinate, or an agrochemically acceptable ester or salt thereof.

[0017] US 4168963 and US 4216226 describe the use of glufosinate or L-glufosinate, respectively.

[0018] The object of the present invention is to provide alternative and / or improved herbicidal mixtures which are highly effective against a variety of weed species, in particular at low doses, and are based on the finding that compounds of formula (I) in combination with glufosinate or L-glufosinate are particularly effective in controlling weeds.

[0019] In a preferred embodiment of the present invention, component (A) is a compound having formula (I), wherein

[0020] R 1 Selected from chlorine and fluorine; preferably R 1 It is fluorine;

[0021] R 2 Selected from chlorine and bromine; preferably R 2 It is chlorine;

[0022] R 3 It is CO2R 5 ;

[0023] R 4 is selected from H, CH3 and CH3CH2-; preferably R 4 It is CH3-;

[0024] R 5 is selected from H, CH3, CH3CH2-, CH3CH2CH2-, CH3CH2CH2CH2-, (CH3)2CH-, (CH3)2CHCH2-, and (CH3)3C-; preferably R 5 It is CH3CH2-.

[0025] In a more preferred embodiment of the present invention, the compound of formula (I) is a compound of formula (Ia).

[0026]

[0027] In a preferred embodiment of the present invention, component (B) is glufosinate-ammonium.

[0028] In another preferred embodiment of the present invention, component (B) is L-glufosinate.

[0029] In preferred compositions according to the invention, the weight ratio of component (A) to component (B) is from 1:1 to 1:50.

[0030] In more preferred compositions according to the invention, the weight ratio of component (A) to component (B) is from 1:3 to 1:50.

[0031] In even more preferred compositions according to the invention, the weight ratio of component (A) to component (B) is from 1 :4 to 1 :32.

[0032] In a second aspect of the present invention, there is provided a herbicidal composition according to the present invention, further comprising at least one additional pesticide.

[0033] In preferred compositions according to the second aspect of the invention, the additional pesticide is a herbicide or a herbicide safener.

[0034] 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, trifludimoxazin, tiafenacil, pyroxasulfone, S-metolachlor, bicyclopyrone, glyphosate, mesotrione, metribuzin and methyl [3-(2-methoxy-4-prop-1-ynyl-phenyl)-4-oxo-2-bicyclo[3.2.1]oct-2-enyl]carbonate.

[0035] 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 chlorpyrifos, cloquintocet, cyprosulfamide, dichlormid, fenoxadone, fenclorim, fluxofenim, furilazole, isoxadifen, mefenpyr, metcamifen and chlorpyrifos.

[0036] In a third aspect of the present invention, there is provided a method of controlling weeds at a locus, the method comprising applying to the locus a weed-controlling amount of a composition of the present invention.

[0037] In a fourth aspect of the present invention, there is provided a method for selectively controlling weeds at a site comprising crop plants and weeds, the method comprising applying a weed-controlling amount of a composition according to the present invention to the site. In a preferred method according to the fourth aspect of the present invention, the crop plants are oil palm, corn, cereals or soybeans.

[0038] In preferred methods according to the fourth aspect of the present invention, the weeds include species selected from the group consisting of: Amaranth species, Ipomoea species, Erigeron species, Kochia species, Floribunda species, Commelina species, Portulaca species, Chenopodium species, Abutilon species, Chickweed species, Eleutherodactyla species, Brachiaria species, Digitaria species, Echinochloa species, Setaria species, Sorghum species, and Lolium species.

[0039] In another aspect, there is provided a method for controlling the growth of PPO-resistant weeds, the method comprising applying to the weeds, a part of the weeds, the weed propagation material, or the locus of the weeds an effective amount of a composition according to the 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 98, amino acid 210, amino acid 361 and / or amino acid 399 in a gene encoding protoporphyrinogen oxidase.

[0040] In another aspect, there is provided a method for controlling the growth of PPO-resistant weeds, the method comprising applying to the weeds, a part of the weeds, the weed propagation material, or the locus of the weeds an effective amount of a composition according to the present invention, wherein the PPO-resistant weeds have a mutation at amino acid 98, amino acid 210 and / or amino acid 399 in the gene encoding protoporphyrinogen oxidase.

[0041] In another aspect, the present invention also relates to the use of a composition according to the invention for controlling weeds that are resistant to PPO herbicides other than compounds of formula (I), such as fluazifop-butyl, fomesafen, and / or lactofop-butyl. These weeds may have developed tolerance to PPO herbicides through evolution, conventional breeding methods, or genetic engineering. Examples include Amaranthus palmeri and Amaranthus tuberculatus, which have evolved resistance to PPO herbicides.

[0042] In another aspect, there is provided the use of a composition according to the invention in crop tops that are tolerant to PPO inhibitors. As known PPO inhibitors, it is clear that compounds of formula (Ia) can be used in methods for controlling undesirable vegetation in crop plants that are tolerant to protoporphyrinogen oxidase (PPO) inhibitors. Such plants can be obtained, for example, by transforming crop plants with a nucleic acid encoding a suitable protoporphyrinogen oxidase, which nucleic acid may contain a mutation to render them more resistant to PPO inhibitors. Examples of such nucleic acids and crop plants are disclosed 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 2016 / 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 plants tolerant to PPO inhibitors comprise a gene encoding the HemG enzyme H_N90, as disclosed in WO 2017 / 023778 and WO 2024 / 015950. In another preferred embodiment, the crop plants tolerant to PPO inhibitors are cotton, corn and soybean.

[0043] When active ingredients are combined, for any given combination of active ingredients the expected effect (E) obeys the so-called Colby formula and can be calculated as follows (Colby, SR, Calculating synergistic and antagonistic responses of herbicide combination, Weeds, Vol. 15, pp. 20-22; 1967):

[0044] ppm = milligrams of active ingredient (ai) per liter

[0045] X = % effect based on first active ingredient using p ppm of active ingredient

[0046] Y = % effect based on the second active ingredient using q ppm of active ingredient.

[0047] According to Colby, using p+q ppm of active ingredient, the expected effect of active ingredient A+B is represented by the following formula:

[0048]

[0049] If the actual observed effect (O) is greater than the expected effect E, then the effect of the combination is superadditive, i.e., there is a synergistic effect. Mathematically, synergism corresponds to a positive value of the difference (OE). In the case of purely complementary additions of active substances (expected activity), the difference (OE) is zero. Negative values ​​of the difference (OE) indicate a loss of activity compared to the expected activity.

[0050] Surprisingly, the combinations of the present invention exhibit additive herbicidal activity, and certain embodiments even exhibit synergistic effects. Synergism exists whenever the effect of the active ingredient combination is greater than the sum of the effects of the individual components.

[0051] The combinations of the present invention may also provide a broadened spectrum of activity compared to the activity achieved with each individual component and / or permit the use of lower ratios of the individual components when used in combination compared to when used individually in order to modulate effective herbicidal activity.

[0052] Furthermore, it is also possible that the compositions according to the invention may show increased crop tolerance when compared with the action of the individual compound A. This occurs when the action of the active ingredient combination is less damaging to useful crops than the action of one of the individual active ingredients.

[0053] When component (A) is a compound having formula (Ia), formula (Ia) is referred to as compound 6 in WO 2016 / 095768. It can be prepared according to Example 1 of WO 2016 / 095768.

[0054] 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 one to four carbon atoms, and attached to the remainder of the molecule by a single bond. 1-4 Examples of alkyl groups include, but are not limited to, methyl (eg, CH3-), ethyl (eg, CH3CH2-), n-propyl, n-butyl, and isomers thereof, such as isopropyl, isobutyl, sec-butyl, or tert-butyl.

[0055] As used herein, the term "C1-C4 alkylcarbonyl" refers to a group having the formula -C(O)R a A group in which R a is a C1-C4 alkyl group as generally defined above. Examples of C1-C4 alkylcarbonyl groups include, but are not limited to, acetyl.

[0056] As used herein, the term "C1-C2 alkylsulfonyl" refers to a group having the formula -S(O)2R a A group in which R a is a C1-C2 alkyl group as generally defined above. Examples of C1-C2 alkylsulfonyl groups include, but are not limited to, methylsulfonyl.

[0057] Throughout this document, the expression "composition" should be interpreted as meaning different mixtures or combinations of components (A) and (B), for example in a single "ready-to-use" form, in a combined spray mixture (which consists of separate formulations of the single active ingredient components, such as a "tank mix"), and in combination when applied in a sequential manner (i.e., one after the other, over a reasonably short period of time, such as a few hours or days). For the implementation of the present invention, the order in which components (A) and (B) are applied is not important. Preferably, they are in a single, ready-to-use form.

[0058] As used herein, the term "herbicide" means a compound that controls or modifies the growth of plants. The term "herbicidally effective amount" means an amount of such a compound or combination of such compounds that produces a controlling or modifying effect on plant growth. Controlling or modifying effects include all deviations from natural development, for example, killing, retardation, leaf burn, albinism, stunting, and the like.

[0059] As used herein, the term "locus" means a place in or on which plants grow, or where seeds of cultivated plants are sown, or where seeds are to be placed in the soil. It includes soil, seeds, and seedlings, as well as established vegetation.

[0060] The term "plant" refers to all physical parts of a plant, including seeds, seedlings, saplings, roots, tubers, stems, stalks, leaves and fruit.

[0061] The term "plant propagation material" means all reproductive parts of a plant, for example seeds or vegetative parts such as cuttings and tubers of a plant. It includes seeds in the strict sense, as well as roots, fruits, tubers, bulbs, rhizomes and parts of plants.

[0062] 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, e.g., a safener protects crops from damage by resistant herbicides but does not prevent the herbicide from killing weeds.

[0063] Crops of useful plants in which the compositions according to the invention can be used include perennial and annual crops, such as berry plants, for example blackberries, blueberries, cranberries, raspberries and strawberries; cereals, for example barley, maize (corn), millet, oats, rice, rye, sorghum, triticale and wheat; fiber plants, for example cotton, flax, hemp, jute and sisal; field crops, for example sugar beets and fodder beets, coffee beans, hops, mustard, rapeseed (canola), poppies, sugar cane, sunflower, tea and tobacco; fruit trees, for example apples, apricots, avocados, bananas, cherries, citrus, nectarines, peaches, pears and plums; grasses, for example Bermuda grass, bluegrass, bentgrass, centipede grass, fescue, ryegrass, St. Augustine grass and zoysia grass; herbs such as basil, borage, chives, cilantro, lavender, lovage, mint, oregano, parsley, rosemary, sage, and thyme; legumes such as beans, lentils, peas, and soybeans; tree nuts such as almonds, cashews, groundnuts, hazelnuts, peanuts, pecans, pistachios, and walnuts; palms such as oil palms; ornamental plants such as flowers, shrubs, and trees; other trees such as cocoa, coconut, olive, and rubber trees; vegetables such as asparagus, eggplant, broccoli, cabbage, carrots, cucumbers, garlic, lettuce, zucchini, melon, okra, onions, peppers, potatoes, pumpkins, rhubarb, spinach, and tomatoes; and vines such as grapes.

[0064] Preferably, the composition of the present invention is used to control weeds in oil palm, corn, cereals or soybeans.

[0065] Crops are to be understood as meaning those which occur naturally, are obtained by conventional breeding methods or are obtained by genetic engineering. These include crops with so-called output traits, such as improved storage stability, higher nutritional value and improved flavour.

[0066] Crops are to be understood as also including those crops which 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 methods of breeding or by genetic engineering. Examples of crops which have been rendered tolerant to imidazolinones (e.g. imazamox) by conventional methods of breeding are Examples of crops that have been rendered tolerant to herbicides by genetic engineering methods include, for example, maize varieties resistant to glyphosate and glufosinate, which are now and It is commercially available under the trademark GLUTAM®.

[0067] Crops are also to be understood as meaning those crops which have been rendered resistant to harmful insects by genetic engineering methods, such as Bt maize (resistant to the European corn borer), Bt cotton (resistant to the boll weevil) and also Bt potatoes (resistant to the Colorado beetle). Examples of Bt maize are Bt 176 corn hybrid (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-A-451 878, EP-A-374 753, WO 93 / 07278, WO 95 / 34656, WO 03 / 052073 and EP-A-427 529. Examples of transgenic plants comprising one or more genes encoding insecticide resistance and expressing one or more toxins are (Corn), Yield (corn), (cotton), (cotton), (potato), as well as Plant crops or their seed material can be both herbicide-resistant and simultaneously resistant to insect feeding ("stacked" transgenic events). For example, a seed can have the ability to express an insecticidal Cry3 protein while being tolerant to glyphosate.

[0068] Examples of crops rendered tolerant to PPO-inhibiting herbicides by genetic engineering are known in the art, for example, as described in WO 95 / 34659. Examples of crops rendered tolerant to HPPD-inhibiting herbicides by genetic engineering 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.

[0069] The compositions of the present invention can typically be used to control a 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., Echinochloa crus-galli), Millet species (e.g., Eleusine indica), Lolium species (e.g., Lolium perenne, Lolium multiflorum), Panicum species (e.g., Panicum spp.), and sp.) (e.g., Panicum miliaceum), Poa sp. (e.g., Poa annua), Setaria species (e.g., Setaria viridis, Setaria faberi), and Sorghum species (e.g., Sorghum bicolor).Examples of dicotyledonous species that can be controlled include Abutilon species (e.g., Abutilon theophrasti), Amaranth species (e.g., Amaranthus retroflexus, Amaranthus longifolia), Bidens species (e.g., Bidens Pilosa), Chenopodium species (e.g., Chenopodium album), White wine grass species (e.g., Conyza canadensis), Euphorbia species (e.g., Euphorbia heterophylla), Galium species (e.g., Galium aparine), Ipomoea species (e.g., Ipomoea hederacea), Kochia species (e.g., Kochia scoparia), Polygonum species (e.g., 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. (e.g., Veronica persica), and Xanthium sp. (e.g., Xanthium strumarium).

[0070] Preferably, the composition of the present invention is used to control Amaranthus species, Ipomoea species, Erigeron species, Kochia species, Floribunda species, Commelina species, Portulaca species, Chenopodium species, Abutilon species, Chickweed species, Millettia species, Brachiaria species, Digitaria species, Echinochloa species, Setaria species, Sorghum species, Phalaenopsis species, Sorghum species, Euphorbia species, Polygonum species, and Lolium species.

[0071] More preferably, the composition of the present invention is used to control Amaranthus species, Ipomoea species, Erigeron species, Kochia species, Floribunda species, Commelina species, Portulaca species, Chenopodium species, Abutilon species, Chickweed species, Eleutherococcus species, Brachiaria species, Digitaria species, Echinochloa species, Setaria species, Sorghum species, and Lolium species.

[0072] Even more preferably, the composition of the present invention is used to control Amaranthus spp., Ipomoea spp., Chenopodium spp., Abutilon spp., Chickweed spp., Digitaria spp., Echinochloa spp., Setaria spp.

[0073] In one aspect, the compositions of the invention are used to control Digitaria species, Echinochloa species, Setaria species, Chickweed species, Amaranth species, Chenopodium species, Abutilon species, Ipomoea species, Phalaris species, Sorghum species, Euphorbia species, Polygonum species, and Goosegrass.

[0074] In another aspect, the compositions of the invention are used to control crabgrass, barnyard grass, foxtail grass, chickweed, red snapper, pigweed, velvet, sedge, Phalaris minor, sorghum, spurge, polygonum convolvulus, and goosegrass.

[0075] In all aspects of the invention, in any particular embodiment, the weeds to be controlled and / or growth inhibited can be monocotyledonous or dicotyledonous weeds that are tolerant or resistant to one or more other herbicides, such as, 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.

[0076] The compositions of the present invention may also be mixed with one or more additional pesticides including herbicides [typically different from herbicides (A) and (B)], fungicides, insecticides, nematicides, bactericides, acaricides, growth regulators, chemosterilants, semiochemicals, repellents, attractants, pheromones, feeding stimulants or other biologically active compounds to form multi-component pesticides giving broader spectrum agricultural protection.

[0077] Preferred herbicides (as additional mixing partners) are selected from one or more of the following: acetochlor, acifluorfen (including acifluorfen-sodium), clonifen-sodium, ametryn, amicarbazone, aminopyralid, cypermethrin, atrazine, fluazifop-M, benquitrione, bensulfuron-methyl (including bensulfuron-methyl), bentazone, bicyclpyrone, bialaphos, bispyribac-sodium, bixlozone, broclozone, herbicide, bromoxynil, butachlor, fluazifop-butyl, mesotrione (including mesotrione-ethyl), chlorsulfuron (including chlorsulfuron-methyl), chlorsulfuron (including chlorsulfuron-ethyl), Chlorotoluron, chlorsulfuron, cyproconazole, clacyfos, clethodim, clodinafop-butyl (including clodinafop-butyl), clomazone, clopyralid, cyclopyranil, cyclopyrimorate, cyprosulfuron, cyhalofop-butyl (including cyhalofop-butyl-butyl), 2,4-D (including its choline salt and 2-ethylhexyl ester), 2,4-DB, betaine, dicamba (including its aluminum, aminopropyl, bis-aminopropylmethyl, choline, dichloropropane, diglycolamine, dimethylamine, dimethylammonium, potassium and sodium salts), diclosulam, diflufenican, fluazifop-butyl, dimethachlor, dimethofuram, dioxopyrithione (including its aluminum, aminopropyl, bis-aminopropylmethyl, choline, dichloropropane, diglycolamine, dimethylamine, dimethylammonium, potassium and sodium salts), diclosulam, diflufenican ... ritrione), dibromodiquat, diuron, epyrifenacil, ethofluanid, ethoxyfuroxan, oxadiazol (including oxadiazol-ethyl), fenoxasulfone, fenpyrasulfone, fenquinotrione, tetrazolam, flazasulfuron, bispyribac, florpyrauxifen (including florpyrauxifen-benzyl), fluazifop (including fluazifop-butyl), fluchloraminopyr (including fluchloraminopyr) sodium, fluchloramin (including fluchloramin minopyr-tefuryl), flufenoximacil, flufenoximacil, fluazifop, fluazifop-butyl, fluometuron, fomesafen, flupyralid (including fluroxypyr-meptyl), flufenacet, fomesafen, foramsulfuron, glufosinate (including L-glufosinate and both ammonium salts), glyphosate (including its hydrazine, isopropyl ammonium and potassium salts), halauxifen (including halauxifen-methyl), haloxalopropyl (including haloxalopropyl-methyl), hexazinone, hydantocidin,Icafolin (including icafolin-methyl), imazamox (including R-imazamox), imazapic, imazapic, imazamox, indolepyr (including indolauxipyr-cyanomethyl), iodosulfuron (including iodosulfuron-methyl-sodium), iofensulfuron (including iofensulfuron-sodium), ioxynil, iptriazopyrid, isoproturon, isoxathiapiprolin, lancotrione, MCPA, MCPB, tetrachloroethylene (DMT), acid (mecoprop-P), mesosulfuron (including mesosulfuron-methyl), mesotrione, metamitron, metazachlor, isothiozolin, isopropylamine, sulfamethoxazole, metribuzin, metribuzin, metsulfuron-methyl, propamide, nicosulfuron, norfadazole, oxadiazon, oxasulfuron, oxyfluorfen, paraquat dichloride, pendimethalin, penoxsulam, benzylpyridinium, picloram, pinoxaden, pretilachlor, primisulfuron-methyl, prometryn, propanil, cypermethrin, propyrisulfuron, propyrisulfuron, pentylpyridinium, prosulfuron, pyraflufen (including pyraflufen-ethyl), pyraflufen-butyl (p pyraquinate), pyrasulfuron, pyridaquat, pyriflubenzoxim, pyrimisulfan, pyroxosulfuron, pyrazosulfuron, quinclorac, quinclorac, quizalofop-ethyl (including quizalofop-P-tefuryl), rimisoxafen, sulfasulfuron, pyriflubenzoxim, sethoxydim, simazine, S-isopropylamine, sulfentrazone, sulfentrazone, thiosulfuron, tethiosulfuron, tethiosulfuron, tetflupyrolimet, thiefonsulfuron, tetflupyrolimet, thiefonsulfuron, tetflupyrolimet, tetiosulfuron ... ncarbazone), thifensulfuron-methyl, tiafenacil, tolpyralate, benzylpyrazone, triafamone, triafamone, wild wheat chlorpyrifos, bensulfuron-methyl, bensulfuron-methyl (including bensulfuron-methyl), triclopyr, trifloxysulfuron (including trifloxysulfuron-sodium), trifludimoxazin, trifluralin, trifloxysulfuron, triazosulfuron, 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-one 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-yl methyl carbonate, ethyl-2-[[3-[[3-chloro-5-fluoro-6-[3-methyl-2,6-dioxo-4-(trifluoromethyl)pyrimidin-1-yl]-2-pyridyl]oxy]acetate, 2-[2-[2-bromo-4- Methyl 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, 6-amino-5-chloro-2-(4-chloro-2-fluoro-3-methoxy-phenyl)pyrimidine-4-carboxylate (2-fluorophenyl)methyl, 6-amino-5-chloro-2-(4-chloro-2-fluoro-3-methoxy-phenyl)pyrimidine-4-carboxylate, 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-carboxylic acid methyl ester, 2-[(2-bromo-6-fluoro-phenyl)methoxy]-4-isopropyl-1-methyl-7-oxabicyclo[2.2.1]heptane and 6-amino-2-(4-chloro-2-fluoro-3-methoxy-phenyl)-5-methoxy-pyrimidine-4-carboxylic acid (isopropylideneamino) ester.

[0078] More preferred herbicides (as additional mixing partners) are ametryn, atrazine, fluazifop-butyl, 2,4-D (including its choline salt and 2-ethylhexyl ester), clorac-sulam, diclosulam, diuron, flazasulfuron, fluazifop-butyl (including fluazifop-butyl-P), fluazifop-butyl, fluazifop-butyl, fomesafen, bicyclopyrone, glyphosate, indazine fluazifop-butyl, isoxaflutole, metribuzin, mesosulfuron, mesotrione, S-isopropylamine, pendimethalin , prometryn, pyrifos, pyrimidine oxadiazine, simazine, sulfentrazone, fluazifop-butyl, terbuthylazine, trifluralin, ethyl 2-[[3-[2-chloro-4-fluoro-5-[3-methyl-2,6-dioxo-4-(trifluoromethyl)pyrimidin-1-yl]phenoxy]-2-pyridinyl]oxy]acetate and methyl [3-(2-methoxy-4-prop-1-ynyl-phenyl)-4-oxo-2-bicyclo[3.2.1]oct-2-enyl]carbonate. Even more preferred herbicides are selected from one or more of the following: atrazine, clethodim, 2,4-D (including its choline salt and 2-ethylhexyl ester), dicamba (including its aluminum, aminopropyl, bis-aminopropylmethyl, choline, dichloropropane, diglycolamine, dimethylamine, dimethylammonium, potassium and sodium salts), diquat dibromide, flazasulfuron, fluazifop-butyl (including fluazifop-butyl-P), fluazifop-butyl, fomesafen, bicyclopyrone, glyphosate, isoxathiapiprolin, metribuzin, methyl disulfuron, mesotrione, S-isopropylamine, paraquat dibromide, pyroxsulfuron, pyrimidine oxime, sulfentrazone, fluazifop-butyl, trifluoperazine, ethyl 2-[[3-[2-chloro-4-fluoro-5-[3-methyl-2,6-dioxo-4-(trifluoromethyl)pyrimidin-1-yl]phenoxy]-2-pyridinyl]oxy]acetate and methyl [3-(2-methoxy-4-prop-1-ynyl-phenyl)-4-oxo-2-bicyclo[3.2.1]oct-2-enyl]carbonate. The most preferred herbicides are selected from the group consisting of paraquat dibromide, diquat dibromide, pyrifos-butyl, trifluoperazine, fluazifop-butyl, pyroxazole, S-isopropylamine, 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.

[0079] Similarly, compositions of the present invention (including those comprising one or more additional pesticides as described in the preceding paragraph) may further comprise one or more safeners. In particular, the following safeners are particularly preferred: AD 67 (MON 4660), fenoxaline, clofonate-mexyl (including clofonate-mexyl-methyl), clofonate-mexyl, cyclopropylsulfonamide, dichloropropane, dicyclonon, dietholate, fenoxadone (including fenoxadone-ethyl), fenoxadone, flurazole, fluazifop, fenoxadone, furilazome, isoxadifen (including isoxadifen-ethyl), pyrazoline oxalate (including pyrazoline oxalate-diethyl), mephenate, mecarphen, oxalocyanate, naphthalic anhydride (CAS RN 81-84-5), TI-35, N-isopropyl-4-(2-methoxy-benzoylsulfamoyl)-benzamide (CAS RN 221668-34-4) and N-(2-methoxybenzoyl)-4-[(benzamide)amino]benzenesulfonamide, and more preferably fenoxadone, clofonet-mexyl, cyclopropylsulfonamide, dichloropropane, fenoxadone, fenoxadil, fluazifop, fenoxadone, isoxadiazole, pyrazoline oxalate, mecarphen and fenoxonitrile. Such safeners may also be in the form of esters or salts, as mentioned in The Pesticide Manual, 15th edition (BCPC), 2009. Therefore, the reference to clofonet-mexyl-methyl also applies to clofonet-mexyl and its lithium, sodium, potassium, calcium, magnesium, aluminum, iron, ammonium, quaternary ammonium, sulfonium or phosphonium salts (as disclosed in WO 02 / 34048), and the reference to fenoxadone-ethyl also applies to fenoxadone, etc.

[0080] The composition of the present invention can be applied before or after crop planting, 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, it is preferred that the mixing ratio of compound (A) to safener is from 100:1 to 1:10, preferably from 20:1 to 1:1.

[0081] The safeners and compositions of the present invention may be applied simultaneously. For example, the safeners and compositions of the present invention may be applied to the site before emergence or to the crop after emergence. The safeners and compositions of the present invention may also be applied sequentially. For example, the safener may be applied prior to sowing the seeds as a seed treatment, and the composition of the present invention may be applied to the site before emergence or to the crop after emergence.

[0082] However, those skilled in the art will appreciate that the compositions of the present invention are particularly useful in non-selective burn-down applications and therefore may also be used to control volunteer or escape crop plants. In such cases, it is clearly not necessary to include a safener in the compositions of the present invention.

[0083] The mass ratio of any two ingredients in each combination is selected to give a desired, e.g., synergistic, effect. In general, the mass ratio will vary depending on the specific ingredients and how many ingredients are present in the combination. In general, the mass ratio between any two ingredients in any combination of the present invention is independently from one another in the range of 100:1 to 1:100, including from 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, 80:2 0, 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, 55:45, 54:4 6、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, 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 to 1:99. Preferred mass ratios between any two components of the present invention are from 75:1 to 1:75, more preferably from 1:1 to 1:50, especially from 1:3 to 1:50, advantageously from 1:3 to 1:32, such as from 1:4 to 1:32, for example from 1:4 to 1:24 or from 1:8 to 1:16. Mixing ratios are understood to include, on the one hand, ratios by mass and, on the other hand, molar ratios.

[0084] In a preferred composition according to the present invention, component (A) is a compound having formula (Ia) or a salt, tautomer or N-oxide thereof, and component (B) is glufosinate-ammonium, wherein the weight ratio of component (A) to component (B) is 1:1 to 1:50.

[0085] In a more preferred composition according to the present invention, component (A) is a compound having formula (Ia) or a salt, tautomer or N-oxide thereof, and component (B) is glufosinate-ammonium, wherein the weight ratio of component (A) to component (B) is 1:3 to 1:50.

[0086] In the most preferred composition according to the present invention, component (A) is a compound having formula (Ia) or a salt, tautomer or N-oxide thereof, and component (B) is glufosinate-ammonium, wherein the weight ratio of component (A) to component (B) is 1:4 to 1:32.

[0087] In a preferred composition according to the present invention, component (A) is a compound having formula (Ia) or a salt, tautomer or N-oxide thereof, and component (B) is L-glufosinate, wherein the weight ratio of component (A) to component (B) is 1:1 to 1:50.

[0088] In a more preferred composition according to the present invention, component (A) is a compound having formula (Ia) or a salt, tautomer or N-oxide thereof, and component (B) is L-glufosinate, wherein the weight ratio of component (A) to component (B) is 1:3 to 1:50.

[0089] In the most preferred composition according to the present invention, component (A) is a compound having formula (Ia) or a salt, tautomer or N-oxide thereof, and component (B) is L-glufosinate, wherein the weight ratio of component (A) to component (B) is 1:4 to 1:32.

[0090] In another embodiment, a composition of components (A) and (B) is provided, wherein component (A) is a compound having formula (Ia), and component (B) is glufosinate-ammonium, and wherein the weight ratio of components (A) to (B) is 1:4 to 1:16.

[0091] In another embodiment, a composition of components (A) and (B) is provided, wherein component (A) is a compound having formula (Ia), and component (B) is glufosinate-ammonium, and wherein the weight ratio of components (A) to (B) is 1:4.

[0092] In another embodiment, a composition of components (A) and (B) is provided, wherein component (A) is a compound having formula (Ia), and component (B) is glufosinate-ammonium, and wherein the weight ratio of components (A) to (B) is 1:8.

[0093] In another embodiment, a composition of components (A) and (B) is provided, wherein component (A) is a compound having formula (Ia), and component (B) is glufosinate-ammonium, and wherein the weight ratio of components (A) to (B) is 1:16.

[0094] In another embodiment, a composition of components (A) and (B) is provided, wherein component (A) is a compound having formula (Ia), and component (B) is glufosinate, and wherein the weight ratio of components (A) to (B) is 1:4 to 1:16, and the species to be controlled is PHAMI, SORVU, EPHHL, POLCO, DIGSA, ECHCG, SETTA, STEME, AMARE, CHEAL, IPOHE, or ABUTH.

[0095] In another embodiment, a composition of components (A) and (B) is provided, wherein component (A) is a compound having formula (Ia), and component (B) is glufosinate, and wherein the weight ratio of components (A) to (B) is 1:4, and the species to be controlled is Phalaenopsis tenuis (PHAMI), Sorghum bicolor (SORVU), Euphorbia pulex (EPHHL), or Polygonum convolvulus (POLCO).

[0096] In another embodiment, a composition of components (A) and (B) is provided, wherein component (A) is a compound having formula (Ia), and component (B) is glufosinate, and wherein the weight ratio of components (A) to (B) is 1:8, and the species to be controlled is crabgrass (DIGSA), barnyard grass (ECHCG), giant foxtail grass (SETFA), chickweed (STEME), amaranth (AMARE), (CHEAL), or velvetleaf (ABUTH).

[0097] In another embodiment, a composition of components (A) and (B) is provided, wherein component (A) is a compound having formula (Ia), and component (B) is glufosinate, and wherein the weight ratio of components (A) to (B) is 1:16, and the species to be controlled is Echinochloa crus-galli (ECHCG), Stemella sylvestris (STEME), Amaranthus retroflexus (AMARE), Abuthus velvetleaf (ABUTH), or Ipohea chinensis (IPOHE).

[0098] In another embodiment, a composition of components (A) and (B) is provided, wherein component (A) is a compound having formula (Ia), and component (B) is L-glufosinate, and wherein the weight ratio of components (A) to (B) is 1:4 to 1:16.

[0099] In another embodiment, a composition of components (A) and (B) is provided, wherein component (A) is a compound having formula (Ia), and component (B) is L-glufosinate, and wherein the weight ratio of components (A) to (B) is 1:4.

[0100] In another embodiment, a composition of components (A) and (B) is provided, wherein component (A) is a compound having formula (Ia), and component (B) is L-glufosinate, and wherein the weight ratio of components (A) to (B) is 1:8.

[0101] In another embodiment, a composition of components (A) and (B) is provided, wherein component (A) is a compound having formula (Ia), and component (B) is L-glufosinate, and wherein the weight ratio of components (A) to (B) is 1:16.

[0102] In another embodiment, a composition of components (A) and (B) is provided, wherein component (A) is a compound having formula (Ia), and component (B) is L-glufosinate, and wherein the weight ratio of components (A) to (B) is 1:4 to 1:16, and the species to be controlled is ELEIN, POLCO, Echinochloa crus-galli, STEME, AMARE, or IPOHE.

[0103] In another embodiment, a composition of components (A) and (B) is provided, wherein component (A) is a compound having formula (Ia), and component (B) is L-glufosinate, and wherein the weight ratio of components (A) to (B) is 1:4, and the species to be controlled is ELEIN or POLCO.

[0104] In another embodiment, a composition of components (A) and (B) is provided, wherein component (A) is a compound having formula (Ia), and component (B) is L-glufosinate, and wherein the weight ratio of components (A) to (B) is 1:8, and the species to be controlled is barnyardgrass (ECHCG), Amaranthus retroflexus (AMARE), or Ipohea chinensis (IPOHE).

[0105] In another embodiment, a composition of components (A) and (B) is provided, wherein component (A) is a compound having formula (Ia), and component (B) is L-glufosinate, and wherein the weight ratio of components (A) to (B) is 1:16, and the species to be controlled is barnyardgrass (ECHCG), chickweed (STEME), amaranth (AMARE), or iris (IPOHE).

[0106] When used in the composition of the present invention, component (A) is typically applied at a rate of 25 to 2000 g / ha, more particularly 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 used in combination with component (B) of 5 to 2000 g / ha, and more particularly 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.

[0107] The examples described herein illustrate but do not limit the range of ratios of components (A) and (B) that can be used in the present invention.

[0108] The amount of the composition according to the invention to be applied will depend on various factors, such as the compound used; the object of treatment, such as plants, soil or seeds; the type of treatment, such as 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 in the range of 35 to 4000 g of total composition per hectare, and more commonly between 35 and 2000 g / ha. Application is usually carried out by spraying the composition, typically with a tractor-mounted sprayer for large areas, but other methods such as dusting (for powders), dripping or drenching may also be used.

[0109] The compositions according to the invention can advantageously be used in the formulations described below (in this case, "active ingredient" relates to the respective mixture of compound (A) with compound (B) or, when a safener is also used, to the respective mixture of compound (A) with compound (B) and a safener).

[0110] The individual components of the compositions of the present invention can be used as the technical active ingredients produced. However, more typically, the compositions according to the present invention can be formulated in a variety of ways using formulation adjuvants such as carriers, solvents, and surfactants. These formulations can be in different physical forms, for example, in the form of dusts, gels, wettable powders, water-dispersible granules, water-dispersible tablets, effervescent compressed tablets, emulsifiable concentrates, microemulsifiable concentrates, oil-in-water emulsions, flowable oils, aqueous dispersions, oily dispersions, suspoemulsions, capsule suspensions, emulsifiable granules, soluble liquids, water-soluble concentrates (with water or water-miscible organic solvents as carriers), impregnated polymer films, or in other known forms, for example, from the Manual on Development and Use of FAO and WHO Specifications for Pesticides, United Nations, 1st edition, second revision (2010). Such formulations can be used directly or can be diluted before use. Dilution can be performed with, for example, water, liquid fertilizers, micronutrients, biological organisms, oils or solvents.

[0111] These formulations can be prepared, for example, by mixing the active ingredient with formulation adjuvants in order to obtain compositions in the form of finely divided solids, granules, solutions, dispersions or emulsions. The active ingredients 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, surface-active substances or combinations thereof.

[0112] These active ingredients can also be contained in very fine microcapsules. Microcapsules contain active ingredients in porous carriers. This allows the active ingredient to be released (e.g., slowly released) into the environment in a controlled amount. Microcapsules typically have a diameter of 0.1 to 500 microns. The amount of active ingredient they contain is about 25% to 95% of the capsule weight by weight. These active ingredients can be in the form of a holistic solid, in the form of fine particles in a solid or liquid dispersion, or in the form of a suitable solution. The encapsulated membrane can include, 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 a solid matrix of a base material in the form of finely dispersed particles, but these microcapsules themselves are not wrapped.

[0113] Formulation adjuvants suitable for preparing the compositions according to the invention are known per se. As liquid carriers, 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 acetates, diacetone alcohol, 1,2-dichloropropane, diethanolamine, p-diethylbenzene, diethylene glycol, diethylene glycol rosinate, diethylene glycol butyl ether, diethylene glycol ethyl ether, diethylene glycol methyl ether, N,N-dimethyl Formamide, dimethyl sulfoxide, 1,4-dioxane, dipropylene glycol, dipropylene glycol methyl ether, dipropylene glycol dibenzoate, dipropylene glycol, alkyl pyrrolidone, 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, γ-butyrolactone, glycerol, acetic acid glyceryl, diacetic acid glyceryl, triacetic acid glyceryl, decaglycerol Hexadecane, Hexanediol, Isoamyl Acetate, Isobornyl Acetate, Isooctane, Isophorone, Cumene, Isopropyl Myristate, Lactic Acid, Lauramine, Mesityl Oxide, Methoxypropanol, Methyl Isoamyl Ketone, Methyl Isobutyl Ketone, Methyl Laurate, Methyl Caprylate, 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, xylenesulfonic acid, paraffin, mineral oil, trichloroethylene, perchloroethylene, ethyl acetate, amyl acetate, butyl acetate, propylene glycol methyl ether, diethylene glycol methyl ether, methanol, ethanol, isopropanol and higher molecular weight alcohols such as amyl alcohol, tetrahydrofuranol, hexanol, octanol, ethylene glycol, propylene glycol, glycerol, N-methyl-2-pyrrolidone, etc.

[0114] 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, soy flour, pumice, wood flour, ground walnut shells, lignin, and similar substances.

[0115] Many surface-active substances can be used advantageously in both solid and liquid formulations, especially those which can be diluted with a carrier before use. Surface-active substances can be anionic, cationic, nonionic or polymeric and they can act as emulsifiers, wetting agents or suspending agents or for other purposes. Typical surface-active substances include, for example, salts of alkyl sulfates, such as diethanolammonium lauryl sulfate; salts of alkylarylsulfonates, such as calcium dodecylbenzenesulfonate; alkylphenol / alkylene oxide addition products, such as ethoxylated nonylphenol; alcohol / alkylene oxide addition products, such as ethoxylated tridecanol; soaps, such as sodium stearate; salts of alkylnaphthalenesulfonates, such as sodium dibutylnaphthalenesulfonate; salts of dialkylsulfosuccinates, such as sodium di(2-ethylhexyl)sulfosuccinate; sorbitol esters, such as sorbitol oleate; quaternary amines, such as dodecyltrimethylammonium 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 phosphates; as well as other substances, such as described in: McCutcheon's Detergents and Emulsifiers Annual, MC Publishing Company (MC Publishing Company). Corp., Ridgewood New Jersey (1981).

[0116] Additional adjuvants that can be used in pesticidal formulations include crystallization inhibitors, viscosity regulators, suspending agents, dyes, antioxidants, foaming agents, light absorbers, mixing aids, defoamers, complexing agents, substances and buffers that neutralize or vary the pH, corrosion inhibitors, fragrances, wetting agents, absorption enhancers, micronutrients, plasticizers, glidants, lubricants, dispersants, thickeners, antifreeze agents, microbicides, and liquid and solid fertilizers.

[0117] The formulations according to the invention may comprise additives comprising oils of plant or animal origin, mineral oils, alkyl esters of such oils or mixtures of such oils with oil derivatives. The amount of oil additive in the composition according to the invention is generally from 0.01% to 10% based on the mixture to be applied. For example, the oil additive can be added to the spray tank in the desired concentration after the spray mixture has been prepared. Preferred oil additives include mineral oil or oils of plant origin, such as rapeseed oil, olive oil or sunflower oil; emulsified vegetable oils; alkyl esters of oils of plant origin, such as methyl derivatives; or oils of animal origin, such as fish oil or tallow. Preferred oil additives include C8C 22 Alkyl esters of fatty acids, especially C 12 -C 18Methyl derivatives of fatty acids, such as the methyl esters of lauric acid, palmitic acid, and oleic acid (methyl laurate, methyl palmitate, and methyl oleate, respectively). Many oil derivatives are known from the Compendium of Herbicide Adjuvants, 10th edition, Southern Illinois University, 2010.

[0118] These 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, which preferably include 0 to 25% by weight of surface-active substances. While commercial products may preferably be formulated as concentrates, the end user will generally employ dilute formulations.

[0119] The application rate varies within wide limits and depends on the nature of the soil, the application method, the crop plants, the pests to be controlled, the prevailing climatic conditions, and other factors dictated by the application method, the time of application, and the target crop. In general, the composition can be applied at a rate of 1 to 2000 l / ha, in particular 10 to 1000 l / ha.

[0120] A preferred formulation may have the following composition (wt %), wherein the term "active ingredient" refers to the total wt % of the combination of all active ingredients in the composition:

[0121] Emulsifiable concentrates :

[0122] Active ingredient: 1% to 95%, preferably 60% to 90%

[0123] Surfactant: 1% to 30%, preferably 5% to 20%

[0124] Liquid carrier: 1% to 80%, preferably 1% to 35%

[0125] Dust agent :

[0126] Active ingredient: 0.1% to 10%, preferably 0.1% to 5%

[0127] Solid carrier: 99.9% to 90%, preferably 99.9% to 99%

[0128] Suspension concentrate:

[0129] Active ingredient: 5% to 75%, preferably 10% to 50%

[0130] Water: 94% to 24%, preferably 88% to 30%

[0131] Surfactant: 1% to 40%, preferably 2% to 30%

[0132] wettable powder :

[0133] Active ingredient: 0.5% to 90%, preferably 1% to 80%

[0134] Surfactants: 0.5% to 20%, preferably 1% to 15%

[0135] Solid carrier: 5% to 95%, preferably 15% to 90%

[0136] Granules:

[0137] Active ingredient: 0.1% to 30%, preferably 0.1% to 15%

[0138] Solid carrier: 99.5% to 70%, preferably 97% to 85%

[0139] Various aspects and embodiments of the present invention will now be described in more detail by way of example. It will be appreciated that modifications of detail may be made without departing from the scope of the invention.

[0140] Examples

[0141] Preparation Examples

[0142]

[0143]

[0144] The combination is thoroughly mixed with the adjuvants and the mixture is thoroughly ground in a suitable grinder to obtain wettable powders which can be diluted with water to give a suspension of the desired concentration.

[0145]

[0146] The combination is thoroughly mixed with adjuvants and the mixture is thoroughly ground in a suitable grinder to obtain a powder that can be used directly for seed treatment.

[0147] Emulsifiable concentrates

[0148]

[0149] Emulsions of any desired dilution which can be used in plant protection can be obtained from these concentrates by dilution with water.

[0150]

[0151] A ready-to-use dust is obtained by mixing the combination with a carrier and grinding the mixture in a suitable grinder. Such dusts can also be used for dry seed dressing.

[0152] Extruded granules

[0153]

[0154] The combination is mixed with the adjuvants and ground, and the mixture is moistened with water. The mixture is extruded and then dried in a stream of air.

[0155] Coated granules

[0156] Active ingredient 8%

[0157] Polyethylene glycol (molecular weight 200) 3%

[0158] Kaolin 89%

[0159] This finely ground combination is applied uniformly in a mixer to the kaolin moistened with polyethylene glycol. In this way, dust-free coated granules are obtained.

[0160] Suspension concentrates

[0161]

[0162] The finely ground combination is intimately mixed with adjuvants to give a suspension concentrate from which suspensions of any desired dilution can be obtained by dilution with water. Using such dilutions, living plants and plant propagation materials can be treated and protected against microbial infestation by spraying, pouring or immersion.

[0163] Flowable concentrate for seed treatment

[0164]

[0165]

[0166] The finely ground combination is intimately mixed with adjuvants to give a suspension concentrate from which suspensions of any desired dilution can be obtained by dilution with water. Using such dilutions, living plants and plant propagation materials can be treated and protected against microbial infestation by spraying, pouring or immersion.

[0167] Extended-release capsule suspension

[0168] 28 parts of the combination are mixed with 2 parts of an aromatic solvent and 7 parts of a toluene diisocyanate / polymethylene-polyphenyl isocyanate mixture (8:1). This mixture is emulsified in a mixture of 1.2 parts of polyvinyl alcohol, 0.05 parts of a defoamer, and 51.6 parts of water until the desired particle size is reached. To this emulsion, 2.8 parts of a mixture of 1,6-hexanediamine in 5.3 parts of water are added. The mixture is stirred until polymerization is complete. The resulting capsule suspension is stabilized by adding 0.25 parts of a thickener and 3 parts of a dispersant. This capsule suspension formulation contains 28% active ingredient. The diameter of the medium capsules is 8-15 microns. The resulting formulation is applied to the seeds as an aqueous suspension in an apparatus suitable for this purpose.

[0169] Bioefficacy Testing

[0170] Seeds of various test species (Digital grass (DIGSA), Echinochloa crusgalli (ECHCG), Setaria officinalis (SETFA), Chickweed (STEME), Amaranthus retroflexus (AMARE), Chenopogon quinoa (CHEAL), Abuth, IPOHE, PHAMI, ELEIN, Sorghum bicolor (SORVU), EPHHL, POLCO) were sown in standard soil in pots and cultivated under controlled conditions in a greenhouse (at 24° / 16°, day / night; 14 h light; 65% humidity) with component (A) dissolved in acetone and IF50 (11.12% Emulsogen EL360™ + 44.44% N-methylpyrrolidone + 44.44% Dowanol DPM glycol ether) and component (B) were neutralized with 0.2% Genapol in water. The plants were sprayed with an aqueous spray solution diluted to the desired concentration using XO80 (CAS No. 9043-30-5) as a diluent. The test compound or composition was applied at the prescribed rate. The test plants were then grown in a greenhouse under controlled conditions (24° / 16° day / night; 14 hours of light; 65% humidity) and watered twice daily. After 14 days, the test was evaluated for the percentage of damage inflicted on the plants (100 = complete damage to the plant; 0 = no damage to the plant). The results are shown in Tables B1 to B18 below.

[0171] Table B1: Post-emergence efficacy of a composition of a compound of formula (Ia) and glufosinate against Digitaria sanguinalis (DIGSA)

[0172]

[0173] Table B2: Post-emergence efficacy of a composition of a compound of formula (Ia) and glufosinate against barnyardgrass (ECHCG): 4 true leaf growth stage

[0174]

[0175] Table B3: Post-emergence efficacy of a composition of a compound of formula (Ia) and glufosinate against Setaria viridis (SETFA)

[0176]

[0177] Table B4: Post-emergence efficacy of a composition of a compound of formula (Ia) and glufosinate against Stemella ovata (STEME)

[0178]

[0179] Table B5: Post-emergence efficacy of a composition of a compound of formula (Ia) and glufosinate against Amaranthus retroflexus (AMARE)

[0180]

[0181] Table B6: Post-emergence efficacy of the composition of the compound of formula (Ia) and glufosinate on Chenopodium album (CHEAL)

[0182]

[0183] Table B7: Post-emergence efficacy of a composition of a compound of formula (Ia) and glufosinate on Abuthida velutipes

[0184]

[0185] Table B8: Post-emergence efficacy of the composition of the compound of formula (Ia) and glufosinate on IPHOE

[0186]

[0187] Table B9: Post-emergence efficacy of a composition of a compound of formula (Ia) and glufosinate against Phalaris tenuissima (PHAMI)

[0188]

[0189] Table B10: Post-emergence efficacy of a composition of a compound of formula (Ia) and glufosinate on sorghum (SORVU)

[0190]

[0191] Table B11: Post-emergence efficacy of a composition of a compound of formula (Ia) and glufosinate against Euphorbia salicifolia (EPHHL)

[0192]

[0193] Table B12: Post-emergence efficacy of compositions of a compound of formula (Ia) and glufosinate against Polygonum convolvulus (POLCO)

[0194]

[0195] Table B13: Post-emergence efficacy of a composition of a compound of formula (Ia) and L-phosphinothricin against barnyardgrass (ECHCG): 4 true leaf growth stage

[0196]

[0197] Table B14: Post-emergence efficacy of compositions of a compound of formula (Ia) and L-phosphinothricin against Stemella ovata (STEME)

[0198]

[0199] Table B15: Post-emergence efficacy of a composition of a compound of formula (Ia) and L-phosphinothricin against Amaranthus retroflexus (AMARE)

[0200]

[0201] Table B16: Post-emergence efficacy of the composition of the compound of formula (Ia) and L-phosphinothricin on IPHOE

[0202]

[0203] Table B17: Post-emergence efficacy of a composition of a compound of formula (Ia) and L-phosphine ammonium against Eleutherodactylus oleraceus (ELEIN)

[0204]

[0205] Table B18: Post-emergence efficacy of compositions of a compound of formula (Ia) and L-phosphine against Polygonum convolvulus (POLCO)

[0206]

Claims

1. A herbicidal composition comprising (A) a herbicidally effective amount of a compound of formula (I): in R 1 is selected from hydrogen, chlorine and fluorine; R 2 selected from chlorine and bromine; R 3 Selected from CO2R 5 and CH2OR 6 ; R 4 is selected from H, CH3- and CH3CH2-; R 5 Selected from H, CH3-, CH3CH2-, CH3CH2CH2-, CH3CH2CH2CH2-, (CH3)2CH-, (CH3)2CHCH2-, (CH3)3C-, CF3CH2-, allyl, propargyl, CH3OCH2CH2-, C2H5OCH2CH2-, CH3CO2CH2CH2- and tetrahydrofurylmethyl; R 6 is selected from C1-C4 alkylcarbonyl, cyclopropylcarbonyl and C1-C2 alkylsulfonyl; or an agrochemically acceptable salt thereof; and Component (B) is glufosinate or L-glufosinate, or an agrochemically acceptable ester or salt thereof.

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

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

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

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

50.

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

16.

7. The herbicidal composition according to any one of the preceding claims, further comprising at least one additional pesticide.

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

9. The herbicidal composition according to claim 8, wherein The herbicide is selected from the group consisting of paraquat dibromide, diquat dibromide, pyrimidine oxime, trifluoperazine, fluazifop-butyl, pyroxazole, S-isopropylamine, 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. The herbicidal composition according to claim 8, wherein The herbicide safener is selected from the group consisting of fenoxaline, cloquintocet-mexyl, cyproconazole, dichloropropane, fenthiocarb, fenoxadone, fluazifop, fenoxadone, isoxadiazole, pyrazodipine, mecarphen and oxalocyanate.

11. A method of controlling weeds at a locus, the method comprising applying to the locus a weed-controlling amount of the herbicidal composition of any one of claims 1 to 10.

12. A method of selectively controlling weeds at a locus comprising crop plants and weeds, the method comprising applying to the locus a weed-controlling amount of a herbicidal composition according to any one of claims 1 to 10.

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

14. The method according to claim 13, wherein These PPO-resistant weeds have mutations at amino acid 98, amino acid 210, amino acid 361 and / or amino acid 399 in the gene encoding protoporphyrinogen oxidase.

15. Use of a composition according to any one of claims 1 to 10 on crops tolerant to PPO inhibitor herbicides.

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