WO2013133287A1 - 除草組成物 - Google Patents
除草組成物 Download PDFInfo
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- WO2013133287A1 WO2013133287A1 PCT/JP2013/056032 JP2013056032W WO2013133287A1 WO 2013133287 A1 WO2013133287 A1 WO 2013133287A1 JP 2013056032 W JP2013056032 W JP 2013056032W WO 2013133287 A1 WO2013133287 A1 WO 2013133287A1
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- Prior art keywords
- compound
- himekugu
- salt
- sodium
- herbicidal
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Classifications
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- 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
- A01N43/48—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with two nitrogen atoms as the only ring hetero atoms
- A01N43/58—1,2-Diazines; Hydrogenated 1,2-diazines
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- 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
- A01N47/08—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 one or more single bonds to nitrogen atoms
- A01N47/28—Ureas or thioureas containing the groups >N—CO—N< or >N—CS—N<
- A01N47/36—Ureas or thioureas containing the groups >N—CO—N< or >N—CS—N< containing the group >N—CO—N< directly attached to at least one heterocyclic ring; Thio analogues thereof
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- 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
Definitions
- the present invention relates to a herbicidal composition and a method for controlling undesirable plants.
- Patent Document 1 discloses a herbicidal composition containing nicosulfuron and a certain known herbicide, and describes pyridate as an example of the known herbicide. However, at least one selected from the group consisting of (A) pyridate or a salt thereof and (B) flazasulfuron, nicosulfuron, trifloxysulfuron, chlorimuron and an alkyl ester thereof, halosulfuron and an alkyl ester thereof and a salt thereof. It is not known that a herbicidal composition containing a synergistically effective amount of a kind of sulfonylurea compound exhibits a synergistic herbicidal effect.
- An object of the present invention is to provide a herbicidal composition having a broader herbicidal spectrum and a high activity, and to provide a method for controlling undesirable plants using them or suppressing their growth. Another object of the present invention is to provide a method for controlling undesirable plants with reduced sensitivity to herbicides.
- (A) pyridate or a salt thereof, and (B) flazasulfuron, nicosulfuron, trifloxysulfuron, chlorimuron and its alkyl ester, halosulfuron And an alkyl ester thereof, and at least one sulfonylurea compound selected from the group consisting of salts thereof and salts thereof, can provide a herbicidal composition having a broad herbicidal spectrum and having high activity.
- the present invention relates to (A) pyridate or a salt thereof (hereinafter abbreviated as compound A), (B) flazasulfuron, nicosulfuron, trifloxysulfuron, chlorimuron and its alkyl ester, halosulfuron and its alkyl ester and their And a herbicidal composition containing a synergistically effective amount with at least one sulfonylurea compound (hereinafter abbreviated as Compound B) selected from the group consisting of these salts.
- the present invention also relates to a method of controlling the herbicidal composition or controlling its growth by applying the herbicidal composition to an undesired plant or a place where they grow so as to have a synergistically effective amount. Furthermore, the present invention relates to a method for applying a herbicidally effective amount of Compound A to Himekugu or a place where Himekugu grows to control or suppress the growth of Himekugu.
- the present invention can provide a synergistic herbicidal composition having a broad herbicidal spectrum and high activity.
- the herbicidal composition of the present invention can control a wide range of undesired plants occurring on cultivated land or non-cultivated land.
- the herbicidal activity has an effect that is more than that in which each single herbicidal activity is added additively, that is, a synergistic effect. Since such a herbicidal composition of the present invention can be applied at a lower dose than when each agent is applied alone, it is also effective in reducing the environmental load on the application area or its surroundings.
- pyridate (generic name) is O-6-chloro-3-phenylpyridazin-4-yl S-octylthiocarbonate.
- flazasulfuron is 1- (4,6-dimethoxypyrimidin-2-yl) -3- (3-trifluoromethyl-2-pyridylsulfonyl) urea and nicosulfuron (generic name) )
- trifloxysulfuron is 1- (4,6-dimethoxypyrimidine- 2-yl) -3- [3- (2,2,2) -trifluoroethoxy) -2-pyridylsulfonyl] urea
- chlorimuron is 2- (4-chloro-6-methoxypyrimidine- 2-ylcarbamoylsulfamoyl) benzoic acid
- halosulfuron is 2- (4-chloro-6-methoxypyrimidine- 2-ylcarbamoy
- the salt contained in Compound A or Compound B may be any salt as long as it is agriculturally acceptable.
- an alkali metal salt such as sodium salt or potassium salt
- an alkali such as magnesium salt or calcium salt Earth metal salts
- ammonium salts such as monomethylammonium salt, dimethylammonium salt and triethylammonium salt
- inorganic acid salts such as hydrochloride, perchlorate, sulfate and nitrate; acetate and methanesulfonate Organic acid salts; and the like.
- the mixing ratio of Compound A and Compound B must be appropriately adjusted according to the formulation form, weather conditions, the type of weeds to be controlled and the growth situation, etc., and cannot be determined unconditionally. It is preferable that the mixing ratio is an effective amount (synergistic effective amount) in which each effect is manifested.
- the weight ratio is 500: 1 to 1: 2.5, preferably 200: 1 to 0.75: 1. is there.
- the mixing ratio of compound A and compound B is, for example, 500: 1 to 1.3: 1 by weight, desirably 150: 1 to 6: 1.
- the mixing ratio of Compound A and Compound B is, for example, 500: 1 to 2: 1, preferably 200: 1 to 3: 1, particularly preferably 50: by weight. 1 to 3: 1.
- the mixing ratio of Compound A and Compound B is, for example, 500: 1 to 2: 1, preferably 150: 1 to 3: 1 by weight.
- the mixing ratio of Compound A and Compound B is, for example, 500: 1 to 1.3: 1 by weight, desirably 60: 1 to 3: 1.
- the mixing ratio of Compound A and Compound B is, for example, 50: 1 to 1: 2.5 by weight, preferably 20: 1 to 0.8: 1. is there.
- the application rates of Compound A and Compound B need to be adjusted as appropriate according to the mixing ratio of Compound A and Compound B, formulation form, weather conditions, type of weeds to be controlled, growth conditions, etc. It is preferable to use an application amount that provides each effective amount (synergistic effective amount) at which a synergistic effect is expressed.
- Compound A is 200 to 5000 g / ha, desirably 300 to 3000 g / ha
- Compound B is 10 to 500 g / ha, desirably 15 to 400 g / ha.
- compound A is 200 to 5000 g / ha, desirably 300 to 3000 g / ha, and compound B is 10 to 150 g / ha, desirably 20 to 50 g / ha.
- Compound B is nicosulfuron or a salt thereof
- Compound A is 200 to 5000 g / ha, desirably 300 to 3000 g / ha
- Compound B is 10 to 100 g / ha, desirably 15 to 100 g / ha.
- Compound B is trifloxysulfuron or a salt thereof
- Compound A is 200 to 5000 g / ha, desirably 300 to 3000 g / ha
- Compound B is 10 to 100 g / ha, desirably 20 to 100 g / ha. is there.
- Compound B is chlorimuron or an alkyl ester thereof
- Compound A is 200 to 5000 g / ha, desirably 300 to 3000 g / ha
- Compound B is 10 to 150 g / ha, desirably 50 to 100 g / ha.
- Compound B is halosulfuron or an alkyl ester thereof
- Compound A is 200 to 5000 g / ha, desirably 300 to 3000 g / ha
- Compound B is 100 to 500 g / ha, desirably 150 to 400 g / ha. .
- the application of the herbicidal composition of the present invention may be applied to an undesired plant or to a place where they grow. Moreover, you may apply at any time before and after generation
- the herbicidal composition of the present invention can control a wide range of weeds such as annual weeds and perennial weeds.
- cyperids such as green kyllinga ( Kyllinga brevifolia Rottb. Var. Leiolepis ), yellow nutsedge ( Cyperus rotundus L.), and cyperus (amur cyperus ( Cyperus microiria Steud.)).
- cyperaceae kyllinga
- Kyllinga brevifolia Rottb. Var. Leiolepis yellow nutsedge
- Cyperus rotundus L. yellow nutsedge
- cyperus amur cyperus ( Cyperus microiria Steud.)
- (cyperaceae) .. barnyardgrass (.
- barnyardgrass Echinochloa crus-galli L., Echinochloa oryzicola vasing
- crabgrass summer grass, Digitaria ciliaris (Retz ) Koeler, crabgrass (Digitaria sanguinalis (L.) Scop, Digitaria ischaemum Muhl. , Digitaria adscendens Henr., Digitaria microbachne Henr., Digitaria horizontalis Willd.)
- green foxtail green foxtail (Setaria viridis L.)
- goosegrass goosegrass (Eleusine indica L.))
- Johnson grass johnsongrass (sorghum halepense L.
- Veronica persica . persian speedwell (Veronica persica Poir )
- Veronica arvensis corn speedwell (Veronica arvensis L.)
- Murasakisagigoke .
- Mazus miquelii Makino Scrophulariaceae weeds (Scrophulariaceae), such as; (.
- Gnaphalium spicatum Lam Senecio vulgaris (Senecio vulgaris L.), Carduus (Sonchus oleraceus L.), Mallotus Chichikogusa, Gnaphalium affine (Gnaphalium affine D.Don), Giant crocodile ( Conyza sumatrensis Walker), butana ( Hypochoeris radicata L.), mugwort ( Artemisia indica var.
- Umbelliferae weeds such as; violet (violet (Viola mandshurica W . Becker)) violaceae weeds (violaceae) such as; such as the United States Fuuro (carolina geranium (Geranium carolinianum L.) ); Niwazekishou (blue-eyedgrass (Sisyrinchium rosulatum Bicknell )) Iridaceae weeds such as (iridaceae) geraniaceae weeds (geraniaceae); Lamium purpureum (purple deadnettle (Lamium purpureum L.) ), such as henbit of (henbit (Lamium amplexicaule L.)) sheet Family weed (labiatae); velvetleaf (velvetleaf (Abutilon theophrasti MEDIC).
- Malvaceae weeds such as; Ipomoea purpurea (tall morningglory (Ipomoea purpurea L.
- Convolvulaceae weeds such as; Chenopodium album (common lambsquarters (Chenopodium album L.) ) Chenopodiaceae weeds such as (chenopodiaceae); purslane (common purslane (portulaca oleracea L.)) Portulacaceae weeds such as the; (black nightshade (black nightshade (Solanum nigrum L.
- Solanaceae weeds such as (solanaceae); Ooinutade (spotted knotweed (Polygonum lapathifolium L.) ), Sanaetade (green smartweed (Polygonum scabrum MOENCH) Polygonaceae
- the herbicidal composition of the present invention is very useful in practical use.
- the herbicidal composition of the present invention has a remarkable synergistic effect, and even if the application amount of each of compound A and compound B is small, the herbicidal activity is exerted, so that the influence on the surrounding environment can be suppressed.
- the herbicidal composition of the present invention may reduce phytotoxicity to useful crops as compared to when each agent is applied alone. Further, there may be a case where a herbicidal composition having a long duration of herbicidal effect, that is, having a residual effect, can be provided as compared with the case where each of compound A and compound B is applied alone.
- the herbicidal composition of the present invention has advantages such as high control effect on cyperaceae weeds, high control effect on broad-leaved weeds, or suppression of perennial grass weed growth. .
- the herbicidal composition of the present invention has an excellent effect in controlling or suppressing undesirable plants having reduced sensitivity to herbicides (hereinafter also referred to simply as weeds having reduced sensitivity).
- the herbicide include ALS (acetolactic acid synthase) inhibitors including sulfonylurea compounds.
- An example of weeds with reduced sensitivity is Himekugu.
- the herbicidal composition of the present invention may have an excellent effect in controlling or suppressing the growth of not only Himekugu with reduced sensitivity but also other weeds with reduced sensitivity.
- the herbicidal composition of the present invention can be further mixed with other herbicidal compounds, which may improve the range of applicable grass species, the timing of chemical treatment, the herbicidal activity, etc. in a more preferable direction.
- herbicidal active ingredients include the following, but even if not specifically stated, these compounds include salts, alkyl esters, hydrates, different crystal forms, and various structures. If isomers are present, they are naturally included.
- Quaternary ammonium salt systems such as paraquat and diquat, which are said to themselves be free radicals in the plant body, generating active oxygen and exhibiting rapid herbicidal efficacy.
- pyridazinones such as norflurazon, chloridazon, metflurazon; pyrazolynate, pyrazoloxyfen, benzofenap, topramezone, pyrasul photole pyrazoles such as pyrasulfotole; other amitrole, fluridone, flurtamone, diflufenican, methoxyphenone, clomazone, sulcotrione, mesotrione , Tembotrione, tefuryltrione (AVH-301), bicyclopyrone, isoxaflutole, difenzoquat, difenzoquat methyl Difenzoquat-metilsulfate, isoxachlorotole, benzobicyclon, picolinafen, biflubutamide (beflubutamid), compounds described in the claims of International Publication WO2003016286 (SW-065, H-965), compounds described in claims of International Publication WO20090
- MSMA, DSMA, CMA endothal (endothall), endothal dipotassium, endothal sodium (endothall-sodium), endtal mono (N, N-dimethylalkylammonium) (endothall-mono ( N, N-dimethylalkylammonium)), etofumesate, sodium chlorate, pelargonic acid, nonanoic acid, phosamine, fosamine-ammonium, pinoxaden ( pinoxaden, ipfencarbazone, HOK-201, aclolein, ammonium sulfamate, borax, chloroacetic acid, sodium chloroacete, cyanamide ( cyanamide), methylal Acid (methylarsonic acid), dimethylarsinic acid, sodium dimethylarsinate, dinoterb, dinoterb-ammonium, dinoterb-diolamine, dinotab Acetate (dinoterb-acetate), DNOC, ferrous
- Xanthomonas campestris Xanthomonas campestris
- epi heart Sils Nematosorusu Epicoccosirus nematosorus
- epi heart Sils Nematosuperasu Epicoccosirus nematosperus
- Ekiserohiramu monoceras Exserohilum monoseras
- parasitic plants such as Drechslera monoceras (Drechsrela monoceras) It is supposed to show herbicidal efficacy by doing.
- compound A or compound B which is an active ingredient
- various adjuvants in accordance with a conventional method for preparing agricultural chemicals, and powder, granule, granule wettable powder, wettable powder, tablet , Pills, capsules (including forms wrapped in water-soluble films), aqueous suspensions, oily suspensions, microemulsions, suspoemulsions, aqueous solvents, emulsions, solutions, pastes, etc.
- the preparation can be prepared and applied in a form, but any form used in the ordinary art can be used as long as it meets the purpose of the present invention.
- Compound A and Compound B may be mixed together to prepare the preparation, or they may be prepared separately and mixed at the time of application.
- Adjuvants used in the formulation include solid carriers such as kaolinite, sericite, diatomaceous earth, slaked lime, calcium carbonate, talc, white carbon, kaolin, bentonite, clay, sodium carbonate, sodium bicarbonate, sodium sulfate, zeolite, starch; water Solvent such as toluene, xylene, solvent naphtha, dioxane, dimethyl sulfoxide, N, N-dimethylformamide, dimethylacetamide, N-methyl-2-pyrrolidone, alcohol; fatty acid salt, benzoate, polycarboxylate, alkyl Sulfate ester, alkyl sulfate, alkyl aryl sulfate, alkyl diglycol ether sulfate, alcohol sulfate ester, alkyl sulfonate, alkyl aryl sulfonate, aryl sulfonate, lignin sul
- each component of these adjuvants can be used by appropriately selecting one or two or more types without departing from the object of the present invention.
- auxiliary agents they can be appropriately selected from those known in the art.
- various commonly used adjuvants such as extenders, thickeners, anti-settling agents, antifreeze agents, dispersion stabilizers, safeners, antifungal agents, foaming agents, disintegrants, binders may be used. it can.
- the blending ratio of the active ingredient and various adjuvants is 0.001: 99.999 to 95: 5, preferably about 0.005: 99.995 to 90:10, in terms of weight percentage. be able to.
- Various methods can be adopted as the application method of the herbicidal composition of the present invention, and it can be properly used depending on various conditions such as application place, formulation form, type of plant to be controlled and growth situation, for example, as follows: The method is mentioned. 1. Compound A and Compound B are mixed together, and the preparation prepared is applied as it is. 2. Compound A and Compound B are mixed together, and the preparation prepared is diluted to a prescribed concentration with water, etc., and applied with various spreading agents (surfactant, vegetable oil, mineral oil, etc.) as necessary. To do. 3. Compound A and compound B are prepared separately and applied as they are. 4).
- composition according to (1) wherein (B) is at least one sulfonylurea compound selected from the group consisting of flazasulfuron, nicosulfuron, trifloxysulfuron, and salts thereof.
- (B) is chlorimuron, an alkyl ester thereof, or a salt thereof.
- (B) is halosulfuron, an alkyl ester thereof, or a salt thereof.
- (B) is at least one sulfonylurea compound selected from the group consisting of flazasulfuron, trifloxysulfuron, chlorimuron and alkyl esters thereof, halosulfuron and alkyl esters thereof, and salts thereof
- (B) is nicosulfuron or a salt thereof.
- the composition according to (1), wherein the herbicidal active ingredients are only (A) and (B).
- the composition according to (1), wherein the herbicidal active ingredients are only pyridate and nicosulfuron.
- (9) The composition according to (1), wherein (B) is flazasulfuron or a salt thereof.
- (12) at least selected from the group consisting of (A) pyridate or a salt thereof, and (B) flazasulfuron, nicosulfuron, trifloxysulfuron, chlorimuron and an alkyl ester thereof, halosulfuron and an alkyl ester thereof and a salt thereof
- a method for controlling or inhibiting the growth of undesirable plants by applying a herbicidally effective amount of a herbicidal composition containing a synergistically effective amount with one sulfonylurea compound to an undesirable plant or a place where they grow.
- (13) at least selected from the group consisting of (A) pyridate or a salt thereof, and (B) flazasulfuron, nicosulfuron, trifloxysulfuron, chlorimuron and its alkyl ester, halosulfuron and its alkyl ester, and salts thereof
- a method of controlling or inhibiting the growth of an undesired plant by applying a single sulfonylurea compound to an undesired plant or a place where they grow in a synergistically effective amount.
- the method according to (12) or (13), wherein the undesirable plant of (12) or (13) is a plant having reduced sensitivity to a herbicide.
- Test example 1 Field crop soil was packed in a 1 / 1,000,000 ha pot, and a rhizome of green kyllinga ( Kyllinga brevifolia Rottb. Var. Leiolepis ) was planted. 59 days later, EC agent with pyridate as active ingredient (trade name: Pyridate 600EC, manufactured by BCP) and WG agent with flazasulfuron as active ingredient (trade name: Shivagen DF, Ishihara Sangyo Co., Ltd.) ), WG agent containing Trifloxysulfuron Na salt as an active ingredient (trade name: Monument Granule Wettable Powder, manufactured by Syngenta Japan), SC agent containing Nicosulfuron as an active ingredient (trade name: One Hope Emulsion, Ishihara Sangyo) WG) containing halosulfuron methyl as an active ingredient (trade name: INPOOL DF, manufactured by Nissan Chemical Industries), WG agent containing chlorimuron ethyl as an active ingredient (trade name: attractive, Mar
- Test example 2 Field crop soil was packed in a 1 / 1,000,000 ha pot, and seeds of American deer (prickly sida, Sida spinosa L.) were sown.
- American King Deer reaches 5.5-5.8 leaf stage
- the prescribed amount of wettable powder (trade name: Lentagran WP, manufactured by BCP) containing pyridate as an active ingredient and one-hop emulsion (trade name) is 1 It was diluted with water equivalent to 1,000,000 L / ha and treated with a small spray.
- the growth state of American deer was visually observed and the growth inhibition rate (%) calculated in the same manner as in Test Example 1 is shown in Table 2.
- Test example 3 A 1 / 1,000,000 ha pot was filled with upland field soil, and rhizoles of green kyllinga ( Kyllinga brevifolia Rottb. Var. Leiolepis ) were planted. When Himekugu reached the fifth leaf stage, a predetermined amount of EC agent containing pyridate as an active ingredient was diluted in water (equivalent to 2,000 L / ha), and the foliage was treated with a small spray. Table 3 shows the growth inhibition rate (%) obtained by observation of the growth state of Himekugu with the naked eye on the 21st day after the chemical treatment.
- Test example 4 A 1 / 1,000,000 ha pot was filled with upland field soil, and rhizoles of green kyllinga ( Kyllinga brevifolia Rottb. Var. Leiolepis ) were planted. When the Himekug plant height reached 5-7 cm, a predetermined amount of EC agent containing pyridate as an active ingredient was diluted in water (equivalent to 2,000 L / ha) and foliage treated with a small spray. Further, seven days later, a second drug treatment was similarly performed on some Himekugu. Table 4 shows the growth inhibition rate (%) obtained by visual observation of the growth state of Himekugu on the 21st day after the first chemical treatment.
- Test Example 5 A 1 / 300,000 ha pot was filled with upland field soil, and a rhizole of green kyllinga ( Kyllinga brevifolia Rottb. Var. Leiolepis ) was planted. In the fall of the following year, a predetermined amount of EC agent containing pyridate as an active ingredient was diluted in water (equivalent to 2,000 L / ha) and treated with a small spray. Table 5 shows the growth inhibition rate (%) obtained by observing the growth state of Himekugu with the naked eye on the 220th day after the chemical treatment.
- Test Example 6 A 1 / 1,000,000 ha pot was filled with upland field soil and seeds of persian speedwell ( Veronica persica Poir.) Were sown. When the giant red corn reached 4.3-5.2 leaf stage, a predetermined amount of EC agent, One Hope Emulsion (trade name) containing pyridate as an active ingredient was diluted in water (equivalent to 300 L / ha) and treated with a small spray. On the 14th day after the chemical treatment, the growth state of Giant pufferfish was observed with the naked eye, and the growth inhibition rate (%) calculated in the same manner as in Test Example 1 is shown in Table 6.
- persian speedwell Veronica persica Poir.
- Test Example 7 A 1 / 1,000,000 ha pot was filled with upland field soil and seeds of summer grass, Digitaria ciliaris (Retz.) Koeler were sown. When Mehishiba reaches the 4.0-5.0 leaf stage, dilute the prescribed amount of EC preparation and monument granule wettable powder (trade name) containing pyridate as active ingredients in water (equivalent to 300 L / ha), and treat the foliage with a small spray. did. On the 7th day after the chemical treatment, the growth state of barnyard was observed with the naked eye, and the growth inhibition rate (%) calculated in the same manner as in Test Example 1 is shown in Table 7.
- Test Example 8 A 1 / 1,000,000 ha pot was filled with upland field soil and seeds of summer grass, Digitaria ciliaris (Retz.) Koeler were sown. When Meishishiba reached the 4.0-5.0 leaf stage, a predetermined amount of EC agent, Inpool DF (trade name) containing pyridate as an active ingredient was diluted in water (equivalent to 300 L / ha), and the foliage was treated with a small spray. On the 14th day after the chemical treatment, the growth state of the barnyard beet was observed with the naked eye, and the growth inhibition rate (%) calculated in the same manner as in Test Example 1 is shown in Table 8.
- Inpool DF trade name
- Test Example 9 Fill 1 / 1,000,000 ha pot with field soil and sow broad-leaved weeds or cyperaceae weeds.
- sowing weeds reached 4-6 leaf age
- Lentagran WP (trade name) 1000-3000gai / ha
- Shivagen DF (trade name) 20-40gai / ha water (equivalent to 300L / ha) Dilute to small and spray with a small spray.
- the growth inhibition rate (%) was calculated in the same manner as in Test Example 1, whereby the composition of the present application was the same as in Test Example 1. Similar remarkable growth inhibition rate and remarkable synergistic effect can be obtained.
- Test Example 10 A 1 / 1,000,000 ha pot was filled with upland field soil, and rhizoles of green kyllinga ( Kyllinga brevifolia Rottb. Var. Leiolepis ) were planted. When Himekugu reaches 6-7 cm in height, Lentagran WP (trade name), prescribed amount of WG agent (trade name: Dinamic, manufactured by Arista Life Sciences) containing amicarbazone having the same mechanism of action as pyridate was diluted in water (equivalent to 2,000 L / ha) and treated with a small spray.
- Lentagran WP trade name
- WG agent trade name: Dinamic, manufactured by Arista Life Sciences
- amicarbazone which has the same mechanism of action as pyridate (both doses are practical doses), indicates that it is not possible to achieve both a sufficient growth suppression rate for himekug and safety for turf. ing. Under these circumstances, surprisingly, pyridate (both doses are practical) is highly active against Himekugu and highly safe against turf. Sufficient growth inhibition of Himekugu and turf safety. It was found that both can be achieved.
- a herbicidal composition having a broad herbicidal spectrum and high activity can be provided.
- the entire contents of the specification, claims, and abstract of Japanese Patent Application No. 2012-052663 filed on March 9, 2012 are incorporated herein as the disclosure of the specification of the present invention. Is.
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Abstract
Description
しかしながら、(A)ピリデート又はその塩と、(B)フラザスルフロン、ニコスルフロン、トリフロキシスルフロン、クロリムロン及びそのアルキルエステル、ハロスルフロン及びそのアルキルエステル並びにそれらの塩からなる群より選ばれる少なくとも1種のスルホニルウレア系化合物の相乗有効量を含有する除草組成物が相乗的な除草効果を発揮することは知られていない。
即ち本発明は、(A)ピリデート又はその塩(以下化合物Aと略す)と、(B)フラザスルフロン、ニコスルフロン、トリフロキシスルフロン、クロリムロン及びそのアルキルエステル、ハロスルフロン及びそのアルキルエステル及びそれらの塩からなる群より選ばれる少なくとも1種のスルホニルウレア系化合物(以下化合物Bと略す)との相乗有効量を含有する除草組成物に関する。また本発明は、前記除草組成物を望ましくない植物又はそれらが生育する場所に相乗有効量となるように施用し、望ましくない植物を防除又はその生育を抑制する方法に関する。さらに本発明は、化合物Aの除草有効量をヒメクグ又はヒメクグが生育する場所に施用し、ヒメクグを防除又はその生育を抑制する方法に関する。
本発明の除草組成物は、農耕地又は非農耕地に発生する広範囲の望ましくない植物を防除できる。その除草活性は、意外にも、それぞれ単独の除草活性が単に相加的に加えられる以上の効果、即ち相乗効果を奏する。このような本発明の除草組成物は、各薬剤を単独で施用する場合に比し低薬量で施用できるため、施用地域又はその周辺への環境負荷の軽減にも有効である。
2種の有効成分を組み合わせた場合の除草活性が、その2種の有効成分各々の除草活性の単純な合計(期待される活性)よりも大きくなる場合、これを相乗効果という。2種の有効成分の組合せにより期待される活性は、次のようにして計算することができる(Colby S.R.、「Weed」15巻、20~22頁、1967年を参照)。
E=(α+β)-(αβ)/100
ただし式中、
α=除草剤X をx g/haの量で処理した時の生育抑制率
β=除草剤Y をy g/haの量で処理した時の生育抑制率
E=除草剤X をx g/ha及び除草剤Y をy g/haの量で処理した時に期待される生育抑制率
すなわち、実際の生育抑制率(実測値)が上記計算による生育抑制率(計算値)より大きい場合には、組合せによる活性は相乗効果を示すということができる。本発明の除草組成物は、上記式で計算した場合、相乗効果を示す。
化合物Bがフラザスルフロン又はその塩である場合、化合物Aと化合物Bとの混合比率は、例えば重量比で500:1~1.3:1、望ましくは150:1~6:1である。
化合物Bがニコスルフロン又はその塩である場合、化合物Aと化合物Bとの混合比率は、例えば重量比で500:1~2:1、望ましくは200:1~3:1、特に望ましくは50:1~3:1である。
化合物Bがトリフロキシスルフロン又はその塩である場合、化合物Aと化合物Bとの混合比率は、例えば重量比で500:1~2:1、望ましくは150:1~3:1である。
化合物Bがクロリムロン又はそのアルキルエステルである場合、化合物Aと化合物Bとの混合比率は、例えば重量比で500:1~1.3:1、望ましくは60:1~3:1である。
化合物Bがハロスルフロン又はそのアルキルエステルである場合、化合物Aと化合物Bとの混合比率は、例えば重量比で50:1~1:2.5、望ましくは20:1~0.8:1である。
化合物Bがフラザスルフロン又はその塩である場合、化合物Aは200~5000g/ha、望ましくは300~3000g/haであり、化合物Bは10~150g/ha、望ましくは20~50g/haである。
化合物Bがニコスルフロン又はその塩である場合、化合物Aは200~5000g/ha、望ましくは300~3000g/haであり、化合物Bは10~100g/ha、望ましくは15~100g/haである。
化合物Bがトリフロキシスルフロン又はその塩である場合、化合物Aは200~5000g/ha、望ましくは300~3000g/haであり、化合物Bは10~100g/ha、望ましくは20~100g/haである。
化合物Bがクロリムロン又はそのアルキルエステルである場合、化合物Aは200~5000g/ha、望ましくは300~3000g/haであり、化合物Bは10~150g/ha、望ましくは50~100g/haである。
化合物Bがハロスルフロン又はそのアルキルエステルである場合、化合物Aは200~5000g/ha、望ましくは300~3000g/haであり、化合物Bは100~500g/ha、望ましくは150~400g/haである。
さらに、本発明の除草組成物は、例えばカヤツリグサ科雑草に高い防除効果を示したり、広葉雑草に高い防除効果を示したり、或は多年生イネ科雑草の生育を抑制したりするなどの利点を有する。
その上、本発明の除草組成物は、除草剤に対する感受性が低下した望ましくない植物(以下単に感受性が低下した雑草ともいう)を防除又はその生育を抑制する上でも優れた効果を奏する。該除草剤としては、例えばスルホニルウレア系化合物を始めとするALS(アセト乳酸合成酵素)阻害剤などが挙げられる。この感受性が低下した雑草の一例としては、ヒメクグなどが挙げられる。また本発明の除草組成物は、前述の感受性が低下したヒメクグのみならず、それ以外の感受性が低下した雑草を防除又はその生育を抑制する上で優れた効果を奏することもある。
1.化合物Aと化合物Bとを一緒に混合し、製剤調製したものをそのまま施用する。
2.化合物Aと化合物Bとを一緒に混合し、製剤調製したものを水等で所定濃度に希釈し、必要に応じて各種展着剤(界面活性剤、植物油、鉱物油など)を添加して施用する。
3.化合物Aと化合物Bとを別々に製剤調製し、各々をそのまま施用する。
4.化合物Aと化合物Bとを別々に製剤調製し、必要に応じて各々を水等で所定濃度に希釈し、必要に応じて各種展着剤(界面活性剤、植物油、鉱物油など)を添加して、各々施用する。
5.化合物Aと化合物Bとを別々に製剤調製したものを水等で所定濃度に希釈する時に混合し、必要に応じて各種展着剤(界面活性剤、植物油、鉱物油など)を添加して施用する。
(1)(A)ピリデート又はその塩と、(B)フラザスルフロン、ニコスルフロン、トリフロキシスルフロン、クロリムロン及びそのアルキルエステル、ハロスルフロン及びそのアルキルエステル並びにそれらの塩からなる群より選ばれる少なくとも1種のスルホニルウレア系化合物との相乗有効量を含有する除草組成物。
(2)(B)がフラザスルフロン、ニコスルフロン、トリフロキシスルフロン及びそれらの塩からなる群より選ばれる少なくとも1種のスルホニルウレア系化合物である、前記(1)に記載の組成物。
(3)(B)がクロリムロン、そのアルキルエステル又はその塩である、前記(1)に記載の組成物。
(4)(B)がハロスルフロン、そのアルキルエステル又はその塩である、前記(1)に記載の組成物。
(5)(B)がフラザスルフロン、トリフロキシスルフロン、クロリムロン及びそのアルキルエステル、ハロスルフロン及びそのアルキルエステル並びにそれらの塩からなる群より選ばれる少なくとも1種のスルホニルウレア系化合物である、前記(1)に記載の組成物。
(6)(B)がニコスルフロン又はその塩である、前記(1)に記載の組成物。
(7)除草有効成分が、(A)及び(B)のみである、前記(1)に記載の組成物。
(8)除草有効成分が、ピリデート及びニコスルフロンのみである、前記(1)に記載の組成物。
(9)(B)がフラザスルフロン又はその塩である、前記(1)に記載の組成物。
(10)(A)と(B)とを除草相乗効果を奏する量(除草相乗有効量)で含有する、前記(1)~(9)に記載の組成物。
(11)(A)と(B)との混合比率が重量比で500:1~1:2.5である、前記(1)~(9)に記載の組成物。
(12)(A)ピリデート又はその塩と、(B)フラザスルフロン、ニコスルフロン、トリフロキシスルフロン、クロリムロン及びそのアルキルエステル、ハロスルフロン及びそのアルキルエステル並びにそれらの塩からなる群より選ばれる少なくとも1種のスルホニルウレア系化合物との相乗有効量を含有する除草組成物の除草有効量を望ましくない植物又はそれらが生育する場所に施用し、望ましくない植物を防除又はその生育を抑制する方法。
(13)(A)ピリデート又はその塩と、(B)フラザスルフロン、ニコスルフロン、トリフロキシスルフロン、クロリムロン及びそのアルキルエステル、ハロスルフロン及びそのアルキルエステル並びにそれらの塩からなる群より選ばれる少なくとも1種のスルホニルウレア系化合物とを、望ましくない植物又はそれらが生育する場所に相乗有効量となるように施用し、望ましくない植物を防除又はその生育を抑制する方法。
(14)前記(12)又は(13)の望ましくない植物が除草剤に対する感受性が低下した植物である、前記(12)又は(13)に記載の方法。
(15)前記(12)又は(13)の望ましくない植物がALS阻害剤に対する感受性が低下した植物である、前記(12)又は(13)に記載の方法。
(16)前記(12)又は(13)の望ましくない植物がヒメクグである、前記(12)又は(13)に記載の方法。
(17)前記(12)又は(13)の望ましくない植物がALS阻害剤に対する感受性が低下したヒメクグである、前記(12)又は(13)に記載の方法。
(18)(A)の除草相乗効果を奏する量(除草相乗有効量)と(B)の除草相乗効果を奏する量(除草相乗有効量)とを施用する、前記(12)又は(13)に記載の方法。
(19)(A)を200~5000g/ha、(B)を10~500g/ha施用する、前記(12)又は(13)に記載の方法。
(20)(A)ピリデート又はその塩の除草有効量をヒメクグ又はヒメクグが生育する場所に施用し、ヒメクグを防除又はその生育を抑制する方法。
(21)(A)を200~5000g/ha施用する、前記(20)に記載の方法。
(22)ヒメクグが除草剤に対する感受性が低下したヒメクグである、前記(20)に記載の方法。
(23)ヒメクグがALS阻害剤に対する感受性が低下したヒメクグである、前記(20)に記載の方法。
(24)ALS阻害剤がスルホニルウレア系化合物である、前記(15)、(17)又は(23)に記載の方法。
(25)ピリデート又はその塩の除草有効量を、コウライシバが生育する場所に施用し、ヒメクグを防除又はその生育を抑制する、前記(20)の方法。
1/1,000,000haポットに畑作土壌をつめ、ヒメクグ(green kyllinga, Kyllinga brevifolia Rottb. var. leiolepis)の地下茎を植えつけた。その59日後、出穂期のヒメクグに、ピリデートを有効成分とするEC剤(商品名:Pyridate 600EC、BCP社製)、フラザスルフロンを有効成分とするWG剤(商品名:シバゲンDF、石原産業社製)、トリフロキシスルフロンNa塩を有効成分とするWG剤(商品名:モニュメント顆粒水和剤、シンジェンタジャパン社製)、ニコスルフロンを有効成分とするSC剤(商品名:ワンホープ乳剤、石原産業社製)、ハロスルフロンメチルを有効成分とするWG剤(商品名:インプールDF、日産化学工業社製)、クロリムロンエチルを有効成分とするWG剤(商品名:アトラクティブ、丸和バイオケミカル社製)の所定量を2,000L/ha相当の水で希釈して小型スプレーで茎葉処理した。
薬剤処理後、14日目にヒメクグの生育状態を肉眼で観察調査し、下記評価基準に従って評価した。生育抑制率(%)〔実測値〕及びコルビー(Colby)の方法により算出した生育抑制率(%)〔計算値〕を第1表に示す。
生育抑制率(%)=0(無処理区同等)~100(完全枯殺)の抑草率(%)
1/1,000,000haポットに畑作土壌をつめ、アメリカキンゴジカ(prickly sida, Sida spinosa L.)の種子を播種した。アメリカキンゴジカが5.5-5.8葉期に達したとき、ピリデートを有効成分とする水和剤(商品名:Lentagran WP、BCP社製)とワンホープ乳剤(商品名)の所定量を1,000L/ha相当の水で希釈して小型スプレーで茎葉処理した。
薬剤処理後、14日目にアメリカキンゴジカの生育状態を肉眼で観察調査し、前記試験例1と同様に算出した生育抑制率(%)を第2表に示す。
1/1,000,000haポットに畑作土壌をつめ、ヒメクグ(green kyllinga, Kyllinga brevifolia Rottb. Var. leiolepis)の地下茎を植えつけた。ヒメクグが5葉期に達したとき、ピリデートを有効成分とするEC剤の所定量を水(2,000L/ha相当)に希釈し、小型スプレーで茎葉処理した。
薬剤処理後、21日目にヒメクグの生育状態を肉眼で観察調査した生育抑制率(%)を第3表に示す。
1/1,000,000haポットに畑作土壌をつめ、ヒメクグ(green kyllinga, Kyllinga brevifolia Rottb. Var. leiolepis)の地下茎を植えつけた。ヒメクグの草高が5-7cmに達したとき、ピリデートを有効成分とするEC剤の所定量を水(2,000L/ha相当)に希釈し、小型スプレーで茎葉処理した。さらに、その7日後、一部のヒメクグに対し2回目の薬剤処理を同様に行った。
1回目の薬剤処理後、21日目にヒメクグの生育状態を肉眼で観察調査した生育抑制率(%)を第4表に示す。
1/300,000haポットに畑作土壌をつめ、ヒメクグ(green kyllinga, Kyllinga brevifolia Rottb. Var. leiolepis)の地下茎を植えつけた。その翌年の秋に、ピリデートを有効成分とするEC剤の所定量を水(2,000L/ha相当)に希釈し、小型スプレーで茎葉処理した。
薬剤処理後、220日目にヒメクグの生育状態を肉眼で観察調査した生育抑制率(%)を第5表に示す。
1/1,000,000haポットに畑作土壌をつめ、オオイヌノフグリ(persian speedwell (Veronica persica Poir.))の種子を播種した。オオイヌノフグリが4.3-5.2葉期に達したとき、ピリデートを有効成分とするEC剤、ワンホープ乳剤(商品名)の所定量を水(300L/ha相当)に希釈し、小型スプレーで茎葉処理した。
薬剤処理後、14日目にオオイヌノフグリの生育状態を肉眼で観察調査し、前記試験例1と同様に算出した生育抑制率(%)を第6表に示す。
1/1,000,000haポットに畑作土壌をつめ、メヒシバ(summer grass, Digitaria ciliaris (Retz.) Koeler)の種子を播種した。メヒシバが4.0-5.0葉期に達したとき、ピリデートを有効成分とするEC剤、モニュメント顆粒水和剤(商品名)の所定量を水(300L/ha相当)に希釈し、小型スプレーで茎葉処理した。
薬剤処理後、7日目にメヒシバの生育状態を肉眼で観察調査し、前記試験例1と同様に算出した生育抑制率(%)を第7表に示す。
1/1,000,000haポットに畑作土壌をつめ、メヒシバ(summer grass, Digitaria ciliaris (Retz.) Koeler)の種子を播種した。メヒシバが4.0-5.0葉期に達したとき、ピリデートを有効成分とするEC剤、インプールDF(商品名)の所定量を水(300L/ha相当)に希釈し、小型スプレーで茎葉処理した。
薬剤処理後、14日目にメヒシバの生育状態を肉眼で観察調査し、前記試験例1と同様に算出した生育抑制率(%)を第8表に示す。
1/1,000,000haポットに畑作土壌をつめ、広葉雑草あるいはカヤツリグサ科雑草の種子を播種する。播種した雑草の葉令が4-6葉期に達したとき、Lentagran WP(商品名)の1000~3000gai/ha、シバゲンDF(商品名)の20~40gai/haを水(300L/ha相当)に希釈し、小型スプレーで茎葉処理する。
薬剤処理後、14~28日目に雑草の生育状態を肉眼で観察調査し、前記試験例1と同様に生育抑制率(%)を算出することで、本願組成物は、前記試験例1と同様の顕著な生育抑制率及び顕著な相乗効果を得ることができる。
1/1,000,000haポットに畑作土壌をつめ、ヒメクグ(green kyllinga, Kyllinga brevifolia Rottb. Var. leiolepis)の地下茎を植えつけた。ヒメクグが草丈6-7cmに達したとき、Lentagran WP(商品名)、ピリデートと同一の作用機序を有するアミカルバゾンを有効成分とするWG剤(商品名:Dinamic、アリスタライフサイエンス社製)の所定量を水(2,000L/ha相当)に希釈し、小型スプレーで茎葉処理した。一方、1/300,000haポットに畑作土壌をつめ、ターフ状のコウライシバ(manilagrass, Zoysia matrella (L.) Merr.)を張りつけた。コウライシバが活着した後、Lentagran WP(商品名)、Dinamic(商品名)の所定量を水(2,000L/ha相当)に希釈し、小型スプレーで茎葉処理した。
薬剤処理後、27日目にヒメクグの生育状態を、28日目にコウライシバの生育状態を肉眼で観察調査した生育抑制率(%)を第9表に示す。
なお、2012年3月9日に出願された日本特許出願2012-052563号の明細書、特許請求の範囲、及び要約書の全内容をここに引用し、本発明の明細書の開示として、取り入れるものである。
Claims (9)
- (A)ピリデート又はその塩と、(B)フラザスルフロン、ニコスルフロン、トリフロキシスルフロン、クロリムロン及びそのアルキルエステル、ハロスルフロン及びそのアルキルエステル並びにそれらの塩からなる群より選ばれる少なくとも1種のスルホニルウレア系化合物との相乗有効量を含有する除草組成物。
- (A)と(B)との混合比率が重量比で500:1~1:2.5である、請求項1に記載の組成物。
- 請求項1に記載の除草組成物を、望ましくない植物又はそれらが生育する場所に相乗有効量となるように施用し、望ましくない植物を防除又はその生育を抑制する方法。
- (A)を200~5000g/ha、(B)を10~500g/ha施用する、請求項3に記載の方法。
- 望ましくない植物がヒメクグである、請求項3に記載の方法。
- 望ましくない植物が除草剤に対する感受性が低下したヒメクグである、請求項3に記載の方法。
- (A)ピリデート又はその塩の除草有効量をヒメクグ又はヒメクグが生育する場所に施用し、ヒメクグを防除又はその生育を抑制する方法。
- ヒメクグが除草剤に対する感受性が低下したヒメクグである、請求項7に記載の方法。
- (A)ピリデート又はその塩を200~5000g/ha施用する、請求項7に記載の方法。
Priority Applications (10)
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US14/382,620 US9339038B2 (en) | 2012-03-09 | 2013-03-05 | Herbicidal composition |
AU2013228414A AU2013228414B2 (en) | 2012-03-09 | 2013-03-05 | Herbicidal composition |
MX2014010781A MX362345B (es) | 2012-03-09 | 2013-03-05 | Composicion herbicida. |
EP13758587.3A EP2823707B1 (en) | 2012-03-09 | 2013-03-05 | Herbicidal composition |
BR112014020948-0A BR112014020948B1 (pt) | 2012-03-09 | 2013-03-05 | Composição herbicida que compreende piridato e um composto de sulfenilureia, método para controlar plantas indesejáveis ou inibir seu crescimento e método para controlar killinga verde ou inibir seu crescimento |
CN201380013099.2A CN104159448B (zh) | 2012-03-09 | 2013-03-05 | 除草组合物 |
IN7418DEN2014 IN2014DN07418A (ja) | 2012-03-09 | 2013-03-05 | |
ES13758587.3T ES2682893T3 (es) | 2012-03-09 | 2013-03-05 | Composición herbicida |
PH12014501811A PH12014501811A1 (en) | 2012-03-09 | 2014-08-11 | Herbicidal composition |
ZA2014/06878A ZA201406878B (en) | 2012-03-09 | 2014-09-19 | Herbicidal composition |
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JP2012052563 | 2012-03-09 | ||
JP2012-052563 | 2012-03-09 |
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WO2013133287A1 true WO2013133287A1 (ja) | 2013-09-12 |
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PCT/JP2013/056032 WO2013133287A1 (ja) | 2012-03-09 | 2013-03-05 | 除草組成物 |
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US (1) | US9339038B2 (ja) |
EP (1) | EP2823707B1 (ja) |
JP (1) | JPWO2013133287A1 (ja) |
CN (1) | CN104159448B (ja) |
AU (1) | AU2013228414B2 (ja) |
BR (1) | BR112014020948B1 (ja) |
CL (1) | CL2014002357A1 (ja) |
ES (1) | ES2682893T3 (ja) |
HU (1) | HUE039429T2 (ja) |
IN (1) | IN2014DN07418A (ja) |
MX (1) | MX362345B (ja) |
PH (1) | PH12014501811A1 (ja) |
PT (1) | PT2823707T (ja) |
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ZA (1) | ZA201406878B (ja) |
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CN104719315A (zh) * | 2015-02-12 | 2015-06-24 | 海利尔药业集团股份有限公司 | 一种含有三氟啶磺隆与硝磺草酮的除草组合物 |
CN106172458A (zh) * | 2015-06-01 | 2016-12-07 | 四川利尔作物科学有限公司 | 除草组合物及其应用 |
CN105409994A (zh) * | 2015-11-18 | 2016-03-23 | 广东中迅农科股份有限公司 | 一种玉米田除草剂 |
CN105724414A (zh) * | 2016-03-14 | 2016-07-06 | 南京华洲药业有限公司 | 一种含三氟啶磺隆与氯吡嘧磺隆的除草组合物及其应用 |
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2013
- 2013-03-05 ES ES13758587.3T patent/ES2682893T3/es active Active
- 2013-03-05 JP JP2014503864A patent/JPWO2013133287A1/ja active Pending
- 2013-03-05 BR BR112014020948-0A patent/BR112014020948B1/pt not_active IP Right Cessation
- 2013-03-05 IN IN7418DEN2014 patent/IN2014DN07418A/en unknown
- 2013-03-05 US US14/382,620 patent/US9339038B2/en active Active
- 2013-03-05 WO PCT/JP2013/056032 patent/WO2013133287A1/ja active Application Filing
- 2013-03-05 HU HUE13758587A patent/HUE039429T2/hu unknown
- 2013-03-05 CN CN201380013099.2A patent/CN104159448B/zh not_active Expired - Fee Related
- 2013-03-05 MX MX2014010781A patent/MX362345B/es active IP Right Grant
- 2013-03-05 EP EP13758587.3A patent/EP2823707B1/en active Active
- 2013-03-05 PT PT13758587T patent/PT2823707T/pt unknown
- 2013-03-05 AU AU2013228414A patent/AU2013228414B2/en not_active Ceased
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2014
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Also Published As
Publication number | Publication date |
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US20150018214A1 (en) | 2015-01-15 |
PT2823707T (pt) | 2018-10-12 |
ZA201406878B (en) | 2016-07-27 |
ES2682893T3 (es) | 2018-09-24 |
AU2013228414A1 (en) | 2014-09-25 |
CN104159448A (zh) | 2014-11-19 |
US9339038B2 (en) | 2016-05-17 |
BR112014020948B1 (pt) | 2020-08-11 |
IN2014DN07418A (ja) | 2015-04-24 |
EP2823707A1 (en) | 2015-01-14 |
PH12014501811B1 (en) | 2014-11-24 |
EP2823707B1 (en) | 2018-05-30 |
MX362345B (es) | 2019-01-11 |
EP2823707A4 (en) | 2015-06-03 |
JPWO2013133287A1 (ja) | 2015-07-30 |
AU2013228414B2 (en) | 2015-08-06 |
MX2014010781A (es) | 2014-10-14 |
CL2014002357A1 (es) | 2014-11-14 |
HUE039429T2 (hu) | 2018-12-28 |
PH12014501811A1 (en) | 2014-11-24 |
CN104159448B (zh) | 2016-03-30 |
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