Classifications

• • A—HUMAN NECESSITIES
  • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
  • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
  • A01N47/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid
  • A01N47/02—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid the carbon atom having no bond to a nitrogen atom
  • A01N47/06—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid the carbon atom having no bond to a nitrogen atom containing —O—CO—O— groups; Thio analogues thereof
• • A—HUMAN NECESSITIES
  • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
  • A01P—BIOCIDAL, PEST REPELLANT, PEST ATTRACTANT OR PLANT GROWTH REGULATORY ACTIVITY OF CHEMICAL COMPOUNDS OR PREPARATIONS
  • A01P13/00—Herbicides; Algicides
  • A01P13/02—Herbicides; Algicides selective
• • A—HUMAN NECESSITIES
  • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
  • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
  • A01N35/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having two bonds to hetero atoms with at the most one bond to halogen, e.g. aldehyde radical
  • A01N35/08—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having two bonds to hetero atoms with at the most one bond to halogen, e.g. aldehyde radical at least one of the bonds to hetero atoms is to nitrogen
  • A01N35/10—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having two bonds to hetero atoms with at the most one bond to halogen, e.g. aldehyde radical at least one of the bonds to hetero atoms is to nitrogen containing a carbon-to-nitrogen double bond
• • A—HUMAN NECESSITIES
  • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
  • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
  • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
  • A01N43/34—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom
  • A01N43/40—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom six-membered rings
• • A—HUMAN NECESSITIES
  • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
  • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
  • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
  • A01N43/90—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having two or more relevant hetero rings, condensed among themselves or with a common carbocyclic ring system

Definitions

• the present invention relates to novel herbicidal compositions comprising a combination of herbicidal active ingredients which provides control of weeds in crops of useful plants.
• the invention further provides methods of controlling weeds in crops of useful plants, and to the use of the herbicidal composition to control weeds.
• Compounds of Formula (I) are known from WO2015/197468 and provide effective control of problematic weeds in crops.
• Combinations of herbicidal active ingredients are often used in agriculture to increase and/or broaden the control of problematic plants (weeds) in crops of useful plants. In some instances, the combination can give rise to a valuable greater-than-additive (synergistic) effect which can, for example, enable efficient weed control through lower application rates.
• the present invention is based upon novel compositions comprising compounds of Formula (I).
• a herbicidal composition comprising (A) a herbicidally effective amount of a compound of Formula (I) wherein G is selected from the group consisting of hydrogen, -C(0)CH 3 and -C(0)0CH 3 ; and
• the compound of Formula (I) is selected from the group consisting of Formula (la), (lb) and (lc). (la) (lb) (lc)
• the compound of Formula (I) is a compound of Formula (la) - including agrochemically acceptable salts thereof.
• the compound of Formula (I) is a compound of Formula (lb).
• the compound of Formula (I) is a compound of Formula (lc).
• the ACCase-inhibiting herbicide (B) is selected from the group consisting of clethodim (B1), clodinafop (B2) fenoxaprop (B3), fluazifop (B4), haloxyfop (B5) pinoxaden (B6) and propaquizafop (B7) or an agrochemically acceptable ester or salt of any component (B).
• Component (B) may also exist as different enantiomers, and therefore the component (B) may be present as a racemic mixture, single enantiomer or enantiomer enriched form.
• the ACCase-inhibiting herbicide (B) is selected from the group consisting of clethodim (B1), clodinafop (B2) (including clodinafop-propargyl (B2a)), fenoxaprop (B3) (including fenoxaprop-P-ethyl (B3b)), fluazifop (B4) (including fluazifop-P-butyl (B4a), haloxyfop (B5) (including haloxyfop-P-methyl (B5a)) pinoxaden (B6) and propaquizafop (B7).
• component (B) is clethodim (B1).
• component (B) is clodinafop (B2) or clodinafop-propargyl (B2a).
• component (B) is fenoxaprop (B3) or fenoxaprop-P-ethyl (B3a).
• component (B) is fluazifop (B4) or fluazifop-P-butyl (B4a).
• component (B) is haloxyfop (B5) or haloxyfop-P-methyl (B5a).
• component (B) is pinoxaden (B6).
• component (B) is propaquizafop
• the compound of Formula (I) is a compound of Formula (lc) and component B is selected from the group consisting of clethodim (B1 , fluazifop (B4), haloxyfop (B5) and pinoxaden (B6) including agrochemically acceptable salts and/or esters of all of the previously mentioned compounds.
• the herbicidal composition comprises a mixture of components (A) and (B) as disclosed in Table 1 below.
• the mixing ratio (by weight) of the compound of Formula (I) to the compound of component B is from 0.01 :1 to 100:1, more preferably from 0.025:1 to 20:1 , even more preferably from 1:30 to 20:1.
• the preferred ratio ranges for preferred compositions of the invention are given in Tables 2 to 4 below. * Where component (B) exists in alternative forms (e.g salt / ester) then it should be understood that these can be substituted.
• ratio range of A:B for any one of composition numbers M1.001 to M1.011, M2.001 to M2.011 and M3.001 to M3.011 described in Tables 2, 3 and 4 above is likely to be from 1:30 to 16:1, and that each ratio can be optimised depending on the mixture partners.
• approximate ratios of 1:30, 1 :20, 1:10, 1 :5, 1 :4, 1:3, 1:2, 1 :1, 2:1, 3:1 , 4:1 , 5:1, 10:1 , 20:1 30:1 are also envisaged.
• the ACCase-inhibiting herbicide (B) is selected from the group consisting of clethodim (B1), clodinafop (B2) fenoxaprop (B3), fluazifop (B4), haloxyfop (B5) pinoxaden (B6) and propaquizafop (B7) or an agrochemically acceptable ester or salt of any component (B).
• Component (B) may also exist as different enantiomers, and therefore the component (B) may be present as a racemic mixture, single enantiomer or enantiomer enriched form.
• the ACCase-inhibiting herbicide (B) is selected from the group consisting of clethodim (B1), clodinafop (B2) (including clodinafop-propargyl (B2a)), fenoxaprop (B3) (including fenoxaprop-P-ethyl (B3b)), fluazifop (B4) (including fluazifop-P-butyl (B4a), haloxyfop (B5) (including haloxyfop-P-methyl (B5a)) pinoxaden (B6) and propaquizafop (B7).
• compositions of the present invention may further comprise one or more additional herbicidal active ingredient(s), thus providing 3-way, 4-way or even 5-way or more mixes.
• the composition of the present invention may contain more than one (B) component, for example two, three or four (B) components.
• the herbicidal composition further comprises one or more additional herbicidal component(s) (C).
• Component (C) can, for example, include glyphosate (or an acceptable salt thereof), glufosinate (or L-glufosinate) or acceptable salts thereof, an auxin herbicide (e.g 2,4-D or dicamba including acceptable salts thereof), an HPPD-inhibiting herbicide or a VLCFA herbicide, especially those selected from the group consisting of acetochlor, metolachlor and S-metolachlor and pyroxasulfone, preferably S-metolachlor.
• glyphosate or an acceptable salt thereof
• glufosinate or L-glufosinate
• an auxin herbicide e.g 2,4-D or dicamba including acceptable salts thereof
• HPPD-inhibiting herbicide or a VLCFA herbicide especially those selected from the group consisting of acetochlor, metolachlor and S-metolachlor and pyroxasulfone, preferably S-metolachlor.
• a method of controlling weeds at a locus comprising applying to the locus of a weed controlling amount of a composition of the present invention.
• a method of selectively controlling weeds at a locus comprising crop plants and weeds, said method comprising applying to the locus a weed controlling amount of a composition according to the invention.
• the crop plant is soybean.
• weeds could include, for example, volunteer maize (corn), including genetically-modified maize.
• component (A) When applied in a composition of the 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 applied typically in association with 5 to 2000g/ha of component B, and more specifically in association with 5, 10, 15, 20, 25, 50, 75, 100, 120, 125, 140, 150, 200, 240, 250, 300, 400, 480, 500, 750, 1000, 1250, 1500, 1800, or 2000g/ha of component (B).
• the Examples described herein illustrate but do not limit the range of rates of components A and B that may be employed in the invention.
• the amount of a composition according to the invention to be applied will depend on various factors, such as the compounds employed; the subject of the treatment, such as, for example plants, soil or seeds; the type of treatment, such as, for example spraying, dusting or seed dressing; or the application time.
• the application rates of the composition according to the invention depend on the type of effect desired, and typically range from 30 to 4000 g of total composition per hectare, and more commonly between 30 and 2000g/ha.
• the application is generally made by spraying the composition, typically by tractor mounted sprayer for large areas, but other methods such as dusting (for powders), drip or drench can also be used.
• X % action by first active ingredient using p ppm of the active ingredient
• Y % action by second active ingredient using q ppm of the active ingredient.
• synergism corresponds to a positive value for the difference of (O-E).
• expected activity said difference (O-E) is zero.
• a negative value of said difference (O-E) signals a loss of activity compared to the expected activity.
• the combination of the present invention takes advantage of any additive herbicidal activity, and certain embodiments may even exhibit a synergistic effect. This occurs whenever the action of an active ingredient combination is greater than the sum of the actions of the individual components.
• Combinations of the invention may also provide for an extended spectrum of activity in comparison to that obtained by each individual component, and/or permit the use of lower rates of the individual components when used in combination to that when used alone, in order to mediate effective herbicidal activity.
• composition of the invention may show increased crop tolerance, when compared with the effect of the compound A alone. This occurs when the action of an active ingredient combination is less damaging to a useful crop than the action of one of the active ingredients alone.
• composition should be interpreted as meaning the various mixtures or combinations of components (A) and (B), for example in a single “ready-mix” form, in a combined spray mixture composed from separate formulations of the single active ingredient components, such as a “tank-mix”, and in a combined use of the single active ingredients when applied in a sequential manner, i.e. one after the other with a reasonably short period, such as a few hours or days.
• the order of applying the components (A) and (B) is not essential for working the present invention.
• herbicide as used herein means a compound that controls or modifies the growth of plants.
• herbicidally effective amount means the quantity of such a compound or combination of such compounds that is capable of producing a controlling or modifying effect on the growth of plants. Controlling or modifying effects include all deviation from natural development, for example killing, retardation, leaf burn, albinism, dwarfing and the like.
• locus means fields in or on which plants are growing, or where seeds of cultivated plants are sown, or where seed will be placed into the soil. It includes soil, seeds, and seedlings, as well as established vegetation.
• plants refers to all physical parts of a plant, including seeds, seedlings, saplings, roots, tubers, stems, stalks, foliage, and fruits.
• plant propagation material denotes all generative parts of a plant, for example seeds or vegetative parts of plants such as cuttings and tubers. It includes seeds in the strict sense, as well as roots, fruits, tubers, bulbs, rhizomes, and parts of plants.
• 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, a safener protects crops from injury by herbicides but does not prevent the herbicide from killing the weeds.
• Crops of useful plants in which the composition 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; fibre plants for example cotton, flax, hemp, jute and sisal; field crops for example sugar and fodder beet, coffee, hops, mustard, oilseed rape (canola), poppy, sugar cane, sunflower, tea and tobacco; fruit trees for example apple, apricot, avocado, banana, cherry, citrus, nectarine, peach, pear and plum; grasses for example Bermuda grass, bluegrass, bentgrass, centipede grass, fescue, ryegrass, St.
• perennial and annual crops such as berry plants for example blackberries, blueberries, cranberries, raspberries and strawberries
• cereals for example barley, maize (corn), mille
• Augustine grass and Zoysia grass herbs such as basil, borage, chives, coriander, lavender, lovage, mint, oregano, parsley, rosemary, sage and thyme; legumes for example beans, lentils, peas and soya beans; nuts for example almond, cashew, ground nut, hazelnut, peanut, pecan, pistachio and walnut; palms for example oil palm; ornamentals for example flowers, shrubs and trees; other trees, for example cacao, coconut, olive and rubber; vegetables for example asparagus, aubergine, broccoli, cabbage, carrot, cucumber, garlic, lettuce, marrow, melon, okra, onion, pepper, potato, pumpkin, rhubarb, spinach and tomato; and vines for example grapes.
• the compositions of the present invention are particularly useful in controlling weeds in cotton or soybean crops, especially soybean crops.
• Crops are to be understood as being those which are naturally occurring, obtained by conventional methods of breeding, or obtained by genetic engineering. They include crops which contain so-called output traits (e.g. improved storage stability, higher nutritional value and improved flavour).
• output traits e.g. improved storage stability, higher nutritional value and improved flavour.
• Crops are to be understood as also including those crops which have been rendered tolerant to herbicides or classes of herbicides (e.g. ALS-, GS-, EPSPS-, PPO-, ACCase- and HPPD-inhibitors) by conventional methods of breeding or by genetic engineering.
• herbicides or classes of herbicides e.g. ALS-, GS-, EPSPS-, PPO-, ACCase- and HPPD-inhibitors
• An example of a crop that has been rendered tolerant to imidazolinones, e.g. imazamox, by conventional methods of breeding is Clearfield® summer rape (canola).
• crops that have been rendered tolerant to herbicides by genetic engineering methods include e.g. glyphosate- and glufosinate-resistant varieties commercially available under the trade names RoundupReady® and LibertyLink®.
• compositions of the present invention especially any comprising 2,4-D (or an agrochemically acceptable ester or salt thereof), have potential utility in crops which are have been engineered to tolerate 2,4-D herbicides, for example EnlistTM crops, especially EnlistE3TM Soybeans.
• compositions of the present invention especially any comprising dicamba (or an agrochemically acceptable ester or salt thereof) have potential utility in crops which are have been engineered to tolerate dicamba herbicides, for example Roundup Ready 2 XtendTM Soybeans.
• compositions of the invention can typically be used to control a wide variety of monocotyledonous and dicotyledonous weed species in the crop.
• the compositions of the present invention provide particular good control of Alopecurus sp. (e.g Alopecurus myosuroides (ALOMY)), Avena sp. Digitaria sp. (e.g Digitaria sanguinalis (DIGSA), Digitaria insularis (TRCIN)), Echinochloa sp. (e.g Echinochloa crus-galli (ECHCG)), Eleusine sp. (e.g Eleusine indica (ELEIN)), Lolium sp., Setaria sp.
• Alopecurus sp. e.g Alopecurus myosuroides (ALOMY)
• Avena sp. Digitaria sp. e.g Digitaria sanguinalis (DIGSA), Digitaria insularis (TRCIN
• the weeds e.g. to be controlled and/or growth-inhibited, may be monocotyledonous or dicotyledonous weeds, which are tolerant or resistant to one or more herbicides for example, HPPD inhibitor herbicides such as mesotrione, PSII inhibitor herbicides such as atrazine or EPSPS inhibitors such as glyphosate.
• compositions of the invention (which includes those comprising one or more additional pesticide(s)) can further include one or more safeners.
• safeners are especially preferred: benoxacor, cloquintocet (including cloquintocet-mexyl), cyprosulfamide, dichlormid, fenchlorazole (including fenchlorazole-ethyl), fenclorim, fluxofenim, furilazole, isoxadifen (including isoxadifen-ethyl), mefenpyr (including mefenpyr-diethyl), metcamifen and oxabetrinil.
• compositions of the invention can be applied before or after planting of the crops, before weeds emerge (pre-emergence application) or after weeds emerge (post-emergence application).
• a safener is combined with mixtures of the invention, it is preferred that the mixing ratio of compound of Formula (I) to safener is from 100:1 to 1:10, especially from 20:1 to 1:1.
• the safener and the compositions of the invention are applied simultaneously.
• the safener and the composition of the invention might be applied to the locus pre-emergence or might be applied to the crop post-emergence.
• the safener and the composition of the invention are applied sequentially.
• the safener might be applied before sowing the seeds as a seed treatment and the composition of the invention might be applied to the locus pre-emergence or might be applied to the crop post-emergence.
• the compositions of the invention can advantageously be used in formulations as described, for example, in WO2015/197468.
• compositions of the present invention were tested against plants including the following species: Echinochloa crus-gali (ECHCG), Lolium multiflorum (LOLMU), Setaria faberi (SETFA) and Digitaria insularis (TRCIN).
• EHCG Echinochloa crus-gali
• LMU Lolium multiflorum
• SETFA Setaria faberi
• TRCIN Digitaria insularis
• Table B1 Combination of Compound of Formula lc and B1 (clethodim).
• Table B2 Combination of Compound of Formula lc and B4a (fluazifop-P-butyl).

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• Life Sciences & Earth Sciences (AREA)
• Zoology (AREA)
• Wood Science & Technology (AREA)
• Plant Pathology (AREA)
• Environmental Sciences (AREA)
• Engineering & Computer Science (AREA)
• Dentistry (AREA)
• General Health & Medical Sciences (AREA)
• Pest Control & Pesticides (AREA)
• Agronomy & Crop Science (AREA)
• Health & Medical Sciences (AREA)
• Chemical & Material Sciences (AREA)
• Chemical Kinetics & Catalysis (AREA)
• General Chemical & Material Sciences (AREA)
• Agricultural Chemicals And Associated Chemicals (AREA)

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Citations (10)

• 2022
  • 2022-06-29 PY PY202202254929A patent/PY2254929A/es unknown
  • 2022-07-01 WO PCT/EP2022/068244 patent/WO2023280701A1/en not_active Ceased
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  • 2022-07-01 CA CA3222087A patent/CA3222087A1/en active Pending
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  • 2022-07-01 EP EP22743472.7A patent/EP4366527A1/en active Pending
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