CN101102671B - Synergistic herbicidal compositions - Google Patents
Synergistic herbicidal compositions Download PDFInfo
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- CN101102671B CN101102671B CN2005800469352A CN200580046935A CN101102671B CN 101102671 B CN101102671 B CN 101102671B CN 2005800469352 A CN2005800469352 A CN 2005800469352A CN 200580046935 A CN200580046935 A CN 200580046935A CN 101102671 B CN101102671 B CN 101102671B
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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
- A01N41/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a sulfur atom bound to a hetero atom
- A01N41/02—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a sulfur atom bound to a hetero atom containing a sulfur-to-oxygen double bond
- A01N41/04—Sulfonic acids; Derivatives thereof
- A01N41/06—Sulfonic acid amides
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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
- 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
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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
- A01N43/54—1,3-Diazines; Hydrogenated 1,3-diazines
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- Pest Control & Pesticides (AREA)
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- General Health & Medical Sciences (AREA)
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Abstract
The present invention relates to a synergistic herbicidal composition comprising N- [ [(4,6-dimethoxy-2-pyrimidinyl)amino]carbonyl] -2- [2-fluoro- 1 -(methoxymethylcarbony loxy)propyl] -3 -pyridine sulfonamide or N-[[(4,6-dimethoxy-2-pyrimidinyl)amino] carbonyl]-2-[2-fluoro-l-(hydroxy)propyl]-3-pyridine sulfonamide and other herbicidal active materials as active ingredient. The herbicidal composition of the present invention can increase the herbicidal efficacy against major weeds, and can reduce the use amount of active ingredients per unit area, due to the synergistic effect by mixing two herbicidal active ingredient having different physiological functions or different herbicidal activities.
Description
The present invention relates to a kind of Synergistic herbicide compositions, contain following formula (1) compound N-[[(4,6-dimethoxy-2-pyrimidine radicals) amino] carbonyl]-2-[2-fluoro-1-(methoxy carbonyl oxygen base) propyl group]-3-pyridine sulfonamide or following formula (2) compound N-[[(4,6-dimethoxy-2-pyrimidine radicals) amino] carbonyl]-2-[2-fluoro-1-(hydroxyl) propyl group]-3-pyridine sulfonamide and other herbicidal active compoundses with the physiological function different or different activity of weeding with formula (1) or (2) compound, it is characterized in that comparing with single agents, activity of weeding increases, herbicidal spectrum is widened, and has saved absorption of active ingredient.Particularly, the present invention relates to a kind of Herbicidal combinations, contain formula (1) or (2) compound, be selected from other active components of light compositing inhibitor bentazone, protoporphyrinogen IX oxidase inhibitor carfentrazoneethyl and growth hormone type weed killer herbicide with one or more, it is characterized in that strengthening to the activity of weeding of perennial weed and sulfonylurea herbicide-resistant weed is collaborative, avoid to grassy weed particularly Echinochloa control antagonism or make it to reduce to minimum, and improved safety to the rice foliar spray.
Background technology
The present invention relates to a kind of Synergistic herbicide compositions, contain N-[[(4,6-dimethoxy-2-pyrimidine radicals) amino] carbonyl]-2-[2-fluoro-1-(methoxy carbonyl oxygen base) propyl group]-3-pyridine sulfonamide or N-[[(4,6-dimethoxy-2-pyrimidine radicals) amino] carbonyl]-2-[2-fluoro-1-(hydroxyl) propyl group]-3-pyridine sulfonamide and other herbicidal active compoundses are as active component.
In plant husbandry, weeds and cover crop that control suppresses plant growth and causes output to reduce are very important.Because the loss that causes of weeds in the crop genetics, as grow difference or crop yield reduce in order to reduce, and developed some and can effectively prevent and treat described weeds and to the herbicidal active component of crop safety.Up to the present, there is the weed killer herbicide of developing in a large number registered and be used to prevent and treat the weeds of some crop.The weed killer herbicide that is used for preventing and treating the weeds of specific crop genetics should have sufficiently high activity of weeding and broad herbicidal spectrum, and response environment and crop safe enough.Yet not every weed killer herbicide can both satisfy above-mentioned requirements fully.
The increase activity of weeding of normal use and the method for widening the herbicidal spectrum of existing weed killer herbicide are that two or more herbicidal active compoundses with different activity of weeding are mixed.If mix two or more herbicidal active compoundses, may demonstrate than the outstanding herbicide action of independent herbicide application (singly executing).So, when the effectiveness of two or more mixture of ingredients during greater than the expection effort levels of each composition, we are referred to as " synergistic effect ".Yet, the synergistic effect that exists in the Herbicidal mixture of described two or more herbicidal active compoundses only under the part situation as seen.Because the difference of aspects such as herbicidal performance, absorption ratio, transfer, metabolism, the activity of weeding of most of mixtures is lower than singly executing of each composition.The such situation of " antagonism " expression is that the herbicide action of the mixture of two or more herbicidal active compoundses is lower than singly executing of each composition.The such situation of " addition " expression is that the herbicide action of mixture of two or more herbicidal active compoundses is identical with singly executing of each composition.
Simultaneously, Korean Patent KR10-0399366 (application number 10-2000-0059990) discloses a kind of herbicidal active compounds of sulfonylurea herbicide, following formula (1) compound [ISO advises name: fluorine pyrrole sulphur is grand].
Known described fluorine pyrrole sulphur swell soil execute or foliar spray in to rice, wheat, barley (optimum amount: 10-40g active ingredient/ha) and gramineous plants (optimum amount: the safety of 50-200g active ingredient/ha), and multiple weeds kind such as broad leaved weed, grassy weed (Gramineae), sedge weed (Cyperaceae), annual and perennial weed etc. had outstanding control of weeds effect.
Korean Patent KR10-0107924 (application number 10-1993-0006915) discloses another kind of sulfonylurea herbicide herbicidal active compounds, following formula (2) compound N-[[(4,6-dimethoxy-2-pyrimidine radicals) amino] carbonyl]-2-[2-fluoro-1-(hydroxyl) propyl group]-the 3-pyridine sulfonamide:
Known above-claimed cpd can effectively prevent unifacial leaf or broadleaf weed such as barnyard grass (Echinochloa crus-galli), Monochoria vaginalis (Monochoria vaginalis) or short arrowhead (Sagittaria pygmaea), and to rice safety.
Yet, the existing N-[[(4 that reports and formula (2) grand when the fluorine pyrrole sulphur of formula (1), 6-dimethoxy-2-pyrimidine radicals) amino] carbonyl]-2-[2-fluoro-1-(hydroxyl) propyl group]-when the 3-pyridine sulfonamide was applied to the rice field by foliar spray and soil, they were to some grassy weeds; Develop the sulfonylurea herbicide-resistance ecotype in the Monochoria vaginalis, firefly Lin (Scirpus juncoides), Vandellia and the difformed galingale herb (Cyperus difformis) that owing to long-term continuous administration sulfonylurea herbicide; Low with the herbicide action of some perennial weeds such as Eleocharis kuroguwai, Herba Cyperi Glomerati, wild arrowhead (Sagittariatrifolia) etc.And, when being used for wheat or barley field by foliar spray, they belong to etc. with broad leaved weed such as Arabic Veronica (Veronica persica) and the herbicide action of arable land violet low to some grassy weeds such as big fringe amur foxtail (Alopecurs myosuroides), annual bluegrass.In addition, in the control of weeds of turf, they are low to the herbicide action of Arabic Veronica and annual bluegrass (Poa annua).
The light compositing inhibitor be a kind of by disturb or the blocking-up photosynthesis of plants in the electronics transmission to suppress the weed killer herbicide that photosynthesis shows its activity of weeding, mainly absorb by processed leaf.This weed killer herbicide shows quick-acting in processed zone, because it is safer to gramineous crop, through being usually used in rice, wheat and barley.Bentazone, a kind of representational light compositing inhibitor weed killer herbicide mainly is widely used in wheat, barley and rice by foliar spray, and soil is executed and only is used for rice.Bentazone can not be prevented and treated grassy weed in singly executing, therefore only be used to prevent and treat broad leaved weed.Yet, in order to prevent and treat grassy weed, barnyard grass particularly, bentazone often mixes use with grass family agent extremely, described grass family agent extremely is for effective especially weed killer herbicide of control grassy weed such as the acetyl-CoA carboxylase inhibitor (weed killer herbicide that suppresses acetyl-CoA carboxylase, acetyl coenzyme A is the important enzyme during a kind of fatty acid biological synthesizes, be also referred to as the ACC enzyme inhibitor, chemically be divided into aryloxy group phenoxy propionic acid and cyclohexanedione, wherein cyhalofop-butyl etc. belongs to the former, and methoxyphenone belongs to the latter).Its representative example is the mixture of bentazone and cyhalofop-butyl.When grass family agent such as cyhalofop-butyl used in singly executing extremely, it had the good preventing effect to grassy weed.Yet, kill grass family agent such as cyhalofop-butyl and mix with bentazone when using, because antagonism, its herbicide action significantly is lower than singly usually executes (Weed Technol.9,741 (1995)).Therefore, directly mixing often is restricted, and the expection that perhaps can not fully obtain described mixture is renderd a service.
The example of the mixture of the demonstration antagonism of another report is [PesticideBiochemistry and Physiology when light compositing inhibitor Stam F-34 uses with the inhibitor of acetolactate synthetase pyribenzoxim, Volume 67, Number 1, May 2000, pp46-53 (8)].Usually, often the representative example of the described antagonism of report is to comprise bentazone or Stam F-34 when contact-type weed killer herbicide such as light compositing inhibitor, or protoporphyrinogen IX oxidase inhibitor comprises carfentrazoneethyl, comprise cyhalofop-butyl or the inhibitor of acetolactate synthetase [weed killer herbicide that suppresses acetolactate synthestase (ALS) with systemic herbicide such as acetyl-CoA carboxylase inhibitor, acetolactate synthestase is a kind of important enzyme in the biosynthesis of branched-chain amino acid, chemically be divided into sulfonylurea, imidazolone type, triazolo pyrimidine class and pyrimidine radicals (sulfo-) benzoates, the grand sulfonylureas that belongs to of fluorine pyrrole sulphur wherein] comprise that fluorine pyrrole sulphur swells (Weed Science, 1989, Vol.37, No.3, pp.400-404) mix when using, this is the major limitation of splitting the clouding compound.
The weed killer herbicide that belongs to protoporphyrinogen IX oxidase inhibitor shows its activity of weeding by suppressing to relate to the biosynthetic protoporphyrinogen IX of chloroplast oxidase, mainly absorbs by processed leaf, brings into play its herbicide effect.This weed killer herbicide shows quick-acting, but may cause damage to crop (phytotoxicity) when spraying by foliar spray, so it is restricted as the development that leaf portion can use weed killer herbicide.Particularly, the carfentrazoneethyl leaf portion that is used for rice owing to above-mentioned infringement is difficult to develop into can use weed killer herbicide.In addition, particularly the effectiveness of barnyard grass is low especially to grassy weed for carfentrazoneethyl, therefore need mix use with other weed killer herbicides.Yet, when mixing use with other weed killer herbicides, because antagonism, the herbicide action of carfentrazoneethyl often is lower than it and singly executes (Arkansas AgriculturalExperiment Station, B.R.Wells Rice Research Studies 2001, pp.65-69), thus its develop into mixture and be restricted.
The auximone weed killer herbicide have similar physiological function to the plant hormone growth, can disturb the physiological function of plant but surpass certain concentration, thereby show its activity of weeding.The auximone weed killer herbicide has been widely used in controlling weeds, particularly broad leaved weed.Yet, when this auximone weed killer herbicide particularly 2, when 4-D, MCPA, MCPB etc. are applied to rice by foliar spray or soil,, notified rice is caused serious harm if spraying time is incorrect or consumption surpasses optimum amount, be enough to cause output to reduce.For example, for 2,4-D, suggestion optimum amount with 280g active ingredient/ha during productive tiller stage to panicle begins to form use (Korean Crop ProtectionAssociation, 2004, Pesticide Use Manual, 741p).Because described rice infringement, although the auximone weed killer herbicide uses for a long time, it is restricted as the development and the use of rice with weed killer herbicide.In addition, when this weed killer herbicide mixed use with other weed killer herbicides, because antagonism, its herbicide action reduced, so its development as mixture is restricted.
Summary of the invention
The N-[[(4 of and formula (2) grand for the fluorine pyrrole sulphur of increase formula (1), 6-dimethoxy-2-pyrimidine radicals) amino] carbonyl]-2-[2-fluoro-1-(hydroxyl) propyl group]-activity of weeding of 3-pyridine sulfonamide and expand its herbicidal spectrum, the inventor is according to the activity of weeding of individuality, selected to have the herbicidal active component of complementary performance, and verified by biologic test.Selection with herbicidal active component of complementary performance be by, be divided into it grand or formula (2) compound has the class of different biochemical functions and has the class of different herbicidal spectrums, further it be divided into grassy weed, broad leaved weed or sulfonylureas-resistant weed and the specific class of perennial weed with fluorine pyrrole sulphur.The result, find when the composition that contains described herbicidal active component with complementary performance and fluorine pyrrole sulphur swells or during formula (2) compound, compositions display goes out to be enough to show clearly the synergistic effect that activity of weeding increases and herbicidal spectrum is expanded, some mixtures show lower infringement and to the synergistic effect of grassy weed, thereby have finished the present invention.
Therefore, an object of the present invention is to provide a kind of Herbicidal combinations, it is characterized in that because the N-[[(4 of or formula (2) grand with the fluorine pyrrole sulphur of formula (1), 6-dimethoxy-2-pyrimidine radicals) amino] carbonyl]-2-[2-fluoro-1-(hydroxyl) propyl group]-3-pyridine sulfonamide or select to compare that activity of weeding increases and the herbicidal spectrum expansion as singly executing of the herbicidal active compounds of the blending constituent of mixture, therefore can use more a spot of herbicidal constituents, and contained other herbicidal active compoundses can reduce the used labour of herbicide application in the compound of or formula (2) grand by the fluorine pyrrole sulphur of co-administered formula (1) and the Herbicidal combinations, thereby save the cost of control of weeds.Another object of the present invention provides a kind of Herbicidal combinations, in the compound that it is characterized in that the grand or formula (2) of fluorine pyrrole sulphur by co-administered formula (1) and the existing weed killer herbicide when mixing with other weed killer herbicides when using since antagonism to the remarkable reduction of the effect of specific weeds or when singly executing, limit some herbicidal active compoundses of use owing to crop damage, by using as mixture rather than individual singly executing can solve problem to the activity of weeding reduction of specific weeds, activity of weeding can be increased, crop safety can be increased Eleocharis kuroguwai or the resistant weed that is difficult to prevent and treat.
Disclosure of the Invention
For achieving the above object, the invention provides a kind of Herbicidal combinations, the N-[[(4 that contains above-mentioned formula (1), 6-dimethoxy-2-pyrimidine radicals) amino] carbonyl]-2-[2-fluoro-1-(methoxy carbonyl oxygen base) propyl group]-the 3-pyridine sulfonamide is the N-[[(4 of fluorine pyrrole sulphur grand [herbicidal active component hereinafter (A1)] or above-mentioned formula (2), 6-dimethoxy-2-pyrimidine radicals) amino] carbonyl]-2-[2-fluoro-1-(hydroxyl) propyl group]-3-pyridine sulfonamide [herbicidal active component hereinafter (A2)] and other herbicidal active components [herbicidal active component hereinafter (B)].
Therefore, the present invention relates to a kind of Herbicidal combinations, mainly contain herbicidal active component (A1) or (A2), and herbicidal active component (B), wherein (A1) is grand (N-[[(4, the 6-dimethoxy-2-pyrimidine radicals) amino of fluorine pyrrole sulphur] carbonyl]-2-[2-fluoro-1-(methoxy carbonyl oxygen base) propyl group]-the 3-pyridine sulfonamide); (A2) be N-[[(4,6-dimethoxy-2-pyrimidine radicals) amino] carbonyl]-2-[2-fluoro-1-(hydroxyl) propyl group]-the 3-pyridine sulfonamide; (B) be one or more weed killer herbicides that are selected from the compound group of being made up of following weed killer herbicide (B1-B9), described weed killer herbicide has and contained weed killer herbicide (A1) or (A2) different chemical constitution or biological weed control activity in all cases.
The blending constituent (B) that is applicable to mixture can be any compound that belongs to following group (B1)-(B9).The title of most weed killer herbicides is from according to " The Pesticide Manual ", and the 12nd edition, 2000, the common name of the compound of British Crop Protection Council (PM hereinafter), some weed killer herbicides have provided independent list of references.
(B1) acetyl-CoA carboxylase inhibitor
(B1.1) diclofop-methyl and ester thereof, particularly methyl esters (PM, pp.279-280)
() oxazole acyl grass amine (BCPC International Congress-Crop Science ﹠amp B1.2; Technology 2003 collections of thesis, pp.85-92)
(B1.3) cyhalofop-butyl (PM, pp.223-224)
(B1.4) alkynes grass ester (PM, pp.186-187)
(B1.5) Gao oxazole diclofop-methyl and ester thereof, particularly ethyl ester (PM, pp.393-394)
(B1.6) wheat straw volt and ester thereof (PM, pp.415-416)
(B1.7) methoxyphenone (PM, pp.914-915)
(B1.8) clefoxidim (PM, pp.61-62)
(B2) inhibitor of acetolactate synthetase
(B2.1) thifensulfuron methyl (PM, pp.899-900)
(B2.2) metsulfuron-methyl (PM, pp.644-645)
(B2.3) prosulfuron (PM, pp.787-788)
(B2.4) tribenuron-methyl (PM, pp.928-929)
(B2.5) mesosulfuronmethyl (BCPC Conference-Weeds 2001 collections of thesis, pp.43-48)
(B2.6) flazasulfuron (PM, pp.417-418)
(B2.7) Sulfosulfuron (PM, pp.853-854)
(B2.8) iodine metsulfuron-methyl and ester thereof, particularly methyl esters (PM, pp.547-548)
(B2.9) flupyrsulfuron-methyl-sodium and ester thereof, particularly methyl esters (PM, pp.447-448)
(B2.10) bensulfuron-methyl and ester thereof, particularly methyl esters (PM, pp.76-77)
(B2.11) AC322140 (PM, pp.217-218)
(B2.12) cinosulfuron (PM, pp.183-184)
(B2.13) azimsulfuron (PM, pp.48-49)
(B2.14) imazosulfuron (PM, pp.534-544)
(B2.15) pyrazosulfuron (PM, pp.795-797)
(B2.16) Penoxulam (BCPC International Congress-Crop Science ﹠amp; Technology 2003 collections of thesis, pp.85-92)
(B2.17) florasulam (PM, pp.420-421)
(B2.18) two careless ethers (PM, pp.97-98)
(B2.19) pyribenzoxim (PM, pp.801)
(B3) light compositing inhibitor
(B3.1) bentazone (PM, pp.80-81)
(B3.2) Brominal or bromoxynil octanoate (PM, pp.110-112)
(B3.3) ioxynil and ester thereof and salt (PM, pp.548-550)
(B3.4) terbutryn (PM, pp.883-884)
(B3.5) symetryne (PM, pp.837-834)
(B3.6) chlortoluron (PM, pp.169-170)
(B3.7) isoproturon (PM, pp.559-560)
(B4) protoporphyrinogen IX oxidase inhibitor
(B4.1) Oxyfluorfen (PM, pp.702-703)
(B4.2) pyrrole grass ether (PM, pp.792-793)
(B4.3) carfentrazoneethyl (PM, pp.141-142)
(B4.4) cinidon-ethyl (PM, pp.181-182)
(B4.5) Bing Que Evil humulone (PM, pp.690-691)
(B4.6) Huan Wu Evil humulone (PM, pp.718-719)
(B5) carotenoid biosynthesis inhibitor
(B5.1) Diflufenican (PM, pp.296-297)
(B5.2) fluorine pyrrole acyl grass amine (Picolinofen) (PM, pp.742-743)
(B5.3) mesotrione (PM, pp.602)
(B5.4) pyrazoxyfen (PM, pp.797-798)
(B5.5) pyrazolate (PM, pp.793-794)
(B5.6) benzobicylon (PM, pp.82)
(B5.7 the) clomazone (PM, pp.190-191)
(B6) cell wall synthetic inhibitor
(B6.1) butachlor (PM, pp.117-118)
(B6.2) flufenacet (PM, pp.434-435)
(B6.3) mefenacet (PM, pp.593-594)
(B6.4) fentrazamide (PM, pp.406-407)
(B6.5) the third careless amine (PM, pp.755-756)
(B6.6) amine grass azoles (cafenstrole, PM, pp.128-129)
(B6.7) Yi Evil grass amine (isoxaben) (PM, pp.561-562)
(B7) lipid biosynthesis inhibitor
(B7.1) benfuresate (PM, pp.71-72)
(B7.2) ethofumesate (PM, pp.364-365)
(B7.3) prosulfocarb (PM, pp.786-787)
(B7.4) triallate (PM, pp.921-922)
(B7.5) benthiocarb (PM, pp.901-902)
(B8) auximone weed killer herbicide
(B8.1) Triclopyr (PM, pp.933-934)
(B8.2) fluroxypyr and ester thereof (PM, pp.455-457)
(B8.3) 2,4-drips and ester (PM, pp.243-246)
(B8.4) 2 first, 4 chlorine and ester thereof, particularly sulfo-ethyl ester (PM, pp.583-586)
(B8.5) Thistrol and ester thereof, particularly ethyl ester (PM, pp.586-588)
(B8.6) Vi par and pure R isomer thereof, and Vi par salt (PM, pp.489-592)
(B8.7) clomeprop (PM, pp.191-192)
(B8.8) dicamba (PM, pp.265-267)
(B9) other
(B9.1) Pendimethalin (PM, pp.714-715)
(B9.2) dithiopyr (PM, pp.330)
(B9.3) the difenzoquat Methylsulfate (PM, pp.291-292)
(B9.4) bromobutide (PM, pp.108)
(B9.5) indanofan (PM, pp.543-544)
(B9.6) pyributicarb (PM, pp.802)
By in a composition of the present invention, mix and use herbicidal active component (A1) or (A2) and the synergistic effect that (B) obtains when different time sprays, often can observe when these active components.
Usually herbicidal active component that contains in Herbicidal combinations of the present invention (A1) and treating capacity (A2) can change according to target crop, but the active principle of per hectare is 20-300g.For some active components, composition of the present invention must contain than singly executing low treating capacity.
Therefore, at combination species of the present invention, the treating capacity of the herbicidal active component of per hectare should be active component (A) 1-300g usually, preferred 10-200g, active component (B) 1-4000g, preferred 2-2000g.The weight ratio of used A: B can change in wide region in the composition, and preferable range is 1: 200-200: 1, more preferably 1: 100-20: 1, but be not limited thereto.The combination of the reactive compound that final weight ratio can be used according to the concrete field of using, weeds spectrum and desire changes, and can determine in test in advance.
Composition of the present invention can be used for the crop field with selectivity control annual and perennial grassy weed, sedge weed and broad leaved weed.Above-mentioned crop field comprises rice culture, cereal (wheat, barley, oat, rye etc.) cultivation and meadow or herbage.In addition, said composition also can be used for preventing and treating the unwanted weeds on non-crop belts, particularly railroad track or the rice field ridge on every side.
Composition of the present invention can unrestrictedly be used for crop field and non-crop belts by conventional application process, described conventional application process such as soil is executed, water meter is used, foliar spray etc., preferred foliar spray.
With only contain active component (A1) or (A2) compare as the using of composition of weeding active compound, in composition of the present invention, the following compounds that is selected from active component (B) is the composition that broad leaved weed is had greater activity, can replenish activity of weeding to some main broad leaved weeds, for example Arabic Veronica, the arable land violet, clearvers (Galium aparine), corn poppy (Papaver rhoeas) etc.:
(B2.1) thifensulfuron methyl, (B2.2) metsulfuron-methyl, (B2.3) prosulfuron, (B2.4) tribenuron-methyl, (B2.16) penoxulam, (B2.17) florasulam, (B3.1) bentazone, (B3.2) Brominal, (B3.3) ioxynil, (B3.5) symetryne, (B4.1) Oxyfluorfen, (B4.2) pyrrole grass ether, (B4.3) carfentrazoneethyl, (B4.4) cinidon-ethyl, () Bing Que Evil humulone B4.5, () Huan Wu Evil humulone B4.6, (B5.1) Diflufenican, (B5.2) fluorine pyrrole acyl grass amine (picolinofen), (B5.3) mesotrione, (B5.5) pyrazolate, (B5.6) benzobicylon, (B5.7) clomazone, (B6.1) butachlor, (B6.3) mefenacet, (B6.4) fentrazamide, (B6.5) the third careless amine, (B6.6) amine grass azoles, () Yi Evil grass amine (isoxaben) B6.7, (B7.5) benthiocarb, (B8.1) Triclopyr, (B8.2) fluroxypyr, (B8.3) 2,4-drips, (B8.4) 2 first, 4 chlorine, (B8.5) Thistrol, (B8.6) Vi par or Vi par salt, (B8.7) clomeprop, (B8.8) dicamba, (B9.2) dithiopyr, (B9.4) bromobutide, (B9.5) indanofan, (B9.6) pyributicarb.
With only contain active component (A1) or (A2) compare as the using of composition of weeding active compound, in composition of the present invention, the following compounds that is selected from active component (B) is the composition that perennial weed is had greater activity, can replenish activity of weeding to some perennial weeds, particularly: Eleocharis kuroguwai, flat stalk Fischer grass (Scirpus planiculmis), Herba Cyperi Glomerati and wild arrowhead:
(B2.10) bensulfuron-methyl methyl esters, (B2.11) AC322140, (B2.12) cinosulfuron, (B2.13) azimsulfuron, (B2.14) imazosulfuron, (B2.15) pyrazosulfuron, (B3.1) bentazone, (B4.3) carfentrazoneethyl, (B5.4) pyrazoxyfen, (B5.5) pyrazolate, (B7.1) benfuresate, (B8.3) 2,4-drips or ester, (B8.4) 2 first, 4 chlorine or ester, sulfo-ethyl ester, (B8.5) Thistrol or ester, ethyl ester.
With only contain active component (A1) or (A2) compare as the using of composition of weeding active compound, in composition of the present invention, the following compounds that is selected from active component (B) is the composition that grassy weed is had greater activity, can replenish the activity of weeding to some grassy weeds:
(B1.1) diclofop-methyl methyl esters; () oxazole acyl grass amine B1.2, (B1.3) cyhalofop-butyl, (B1.4) alkynes grass ester; () Gao oxazole diclofop-methyl ethyl ester B1.5; (B1.6) flamprop methyl ester, (B1.7) methoxyphenone, (B1.8) clefoxidim; (B2.5) mesosulfuronmethyl; (B2.6) flazasulfuron, (B2.7) Sulfosulfuron, (B2.8) iodine metsulfuron-methyl methyl esters; (B2.9) flupyrsulfuron-methyl-sodium methyl esters; (B2.18) two careless ethers, (B2.19) pyribenzoxim, (B3.4) terbutryn; (B3.6) chlortoluron; (B3.7) isoproturon, (B6.2) flufenacet, (B7.2) ethofumesate; (B7.3) prosulfocarb; (B7.4) triallate, (B9.1) Pendimethalin, (B9.3) difenzoquat Methylsulfate.
With only contain active component (A1) or (A2) compare as the using of composition of weeding active compound, in composition of the present invention, the following compounds that is selected from active component (B) is the composition that the antagonism weeds have greater activity, can replenish activity of weeding, for example resistance Monochoria vaginalis, Vandellia, firefly Lin and difformed galingale herb to some sulfonylurea herbicide resistant weeds:
(B3.1) bentazone, (B3.2) Brominal, (B3.5) symetryne, (B4.1) Oxyfluorfen, (B4.2) pyrrole grass ether, (B4.3) carfentrazoneethyl, (B4.4) cinidon-ethyl, (B4.5) Bing Que Evil humulone, (B4.6) Huan Wu Evil humulone, (B5.1) Diflufenican, (B5.2) fluorine pyrrole acyl grass amine (picolinofen), (B5.3) mesotrione, (B5.5) pyrazolate, (B5.6) benzobicylon, (B5.7) clomazone, (B6.1) butachlor, (B6.3) mefenacet, (B6.4) fentrazamide, (B6.5) the third careless amine, (B6.6) amine grass azoles, (B6.7) Yi Evil grass amine (isoxaben), (B7.5) benthiocarb, (B8.1) Triclopyr, (B8.2) fluroxypyr, (B8.3) 2,4-drips, (B8.4) 2 first, 4 chlorine, (B8.5) Thistrol, (B8.6) Vi par or Vi par salt, (B8.7) clomeprop, (B8.8) dicamba, (B9.2) dithiopyr, (B9.4) bromobutide, (B9.5) indanofan, (B9.6) pyributicarb.
In composition of the present invention, following compounds is selected from active component (B), be used for and only contain active component (A1) or (A2) mix to solve often observable some weeds antagonism of barnyard grass (Echinochloacrus-galli) particularly at other mixtures as the composition of weeding active compound, increase the activity of weeding of antagonism weeds and perennial Eleochariskuroguwai and increase the safety of foliar spray rice:
(B3.1) bentazone, (B4.3) carfentrazoneethyl, (B8.2) fluroxypyr, (B8.3) 2,4-D, (B8.4) MCPA, (B8.5) MCPB, (B8.6) Vi par or mecopropP, (B8.7) clomeprop, (B8.8) dicamba.
In addition, Herbicidal combinations of the present invention can contain other compositions in case of necessity, and for example one or more are selected from the composition of the group of other weed killer herbicides, insecticide, fungicide, safener (reducing the compound of weed killer herbicide to chemical injury of crops) and plant growth regulator.These other compositions can become a kind of preparation to use and mix in the spray tank and use by being formulated in respectively by co-formulated, or use in order.
In addition, Herbicidal combinations of the present invention can be prepared with formulation art carrier, surfactant or additive commonly used.For example, can be processed into non-forms of modification, active component and filler (for example solvent, solid carrier and surfactant according to conventional method, if necessary) evenly mix, by being processed into wetting powder, suspending agent, water dispersible granules as methods such as grinding, granulation, film-makings, granule, liquor, tablet, jumbo preparation etc., be applied to soil and water meter then, or leaves of plants portion.
Suitable carrier and additive can be solid or liquid, comprise the composition that is used for formulation art, for example natural or synthetic inorganic matter, solvent, dispersant, wetting agent, rheology control agent, adhesive, auxiliary agent etc.
Solvent can comprise aromatic hydrocarbon, and for example xylene mixture, or pure and mild glycol and ether and ester are as the naphthalene alcohol that replaces, ethylene glycol, glycol monoethyl ether or ethylene glycol monoethyl ether; Ketone such as cyclohexanone; Intensive polar solvent such as N-N-methyl-2-2-pyrrolidone N-, dimethyl sulfoxide (DMSO) or dimethyl formamide; Epoxidation or non-epoxidized vegetable oil such as epoxidation cocoa butter or soybean oil; Water etc.These solvents can be used as the solvent of formulation in liquid form, or the supplementing solvent of granule type preparation.
Solid carrier can comprise natural or synthetic inorganic matter such as talcum, kaolin, calcium carbonate, diatomite or the pyrophyllite of fine lapping.
Dispersant can comprise anionic dispersing agents such as lignosulfonates, naphthalene sulfonate, lauryl sulfate, lauryl sulfonate, polyoxyalkylene alkyl sulphate; The polyoxyalkylene alkyl aryl ether; Polyoxyalkylene alkyl etc.Dispersant is not limited to above-mentioned substance, can be selected from non-ionic surface active agent and anion surfactant or cationic surfactant in case of necessity.
Wetting agent can comprise anion wetting agent such as NaLS, polyalkylene oxide alkyl phenyl ether sulfonate, the salt of dialkyl sulphosuccinate, dialkyl group naphthalene sulfonate, polyalkylene oxide alkyl ether sulfate; Acetylene class non-ionic surface active agent; The urea compound of non-ionic surface active agent etc.
Suitable rheology control agent can be divided into polysaccharide such as equal type sugar and assorted type sugar and inorganic matter if you would take off soil, montmorillonite, sepiolite, hectoliter and hydrophilic/hydrophobic silica.All type sugar can be furans glue, and assorted type sugar can be guar gum, yellow first glue, wellan glue etc.
Suitable adhesive can comprise starch, dextrin, α starch, mosanom, gum Arabic, gelatin, lignosulfonates, glucose, sorbierite, polyethylene glycol, hydroxypropyl cellulose (HPC), hydroxypropyl methylcellulose, polyvinylpyrrolidone etc.
Auxiliary agent refers in process for preparation and to add increasing the material of chemical result, or in the preparation process of spray solution diluted material.Anion surfactant, cationic surfactant, non-ionic surface active agent etc. are commonly used for auxiliary agent.Suitable auxiliary agent can comprise salt, acetylene class non-ionic surface active agent, polyalkylene oxide alkyl ether, polyalkylene oxide alkyl phenol ether, PEO alkylamine, ethoxylation sorbitan ester, PEO fatty acid ester, the PEO-poly(propylene oxide)-PEO triblock copolymer of dialkyl sulphosuccinate, trisiloxane alkoxylates etc.
The following example will illustrate the effect of the present composition, but scope of the present invention should not be interpreted as being confined to this by any way.
Embodiment
An example of formulations of the present invention is as described below.
The mixture of 10 parts of (10%w/w) herbicidal active components (A1 or A2)/herbicidal active component (B), 2 parts of lauryl sodium sulfate (trade names: NK-SDS, Coseal), 8 parts of (8%w/w) sodium lignin sulfonate (trade names: NK-SLS, Coseal) and 80 parts of (80%w/w) kaolin mix, use hammer mill (model: KDW-1 then, PAUDAL) be ground into average grain diameter 5-10 μ, form wetting powder.
The mixture of 10 parts of (10%w/w) herbicidal active components (A1 or A2)/herbicidal active component (B), 1 part of lauryl sodium sulfate (trade name: NK-SDS, Coseal), 3 parts of (3%w/w) naphthalene-formaldehyde condensation products (trade names: Morwet-D425, Whittko), 5 parts of (5%w/w) propane diols, 0.5 part (0.5%w/w) gel fraction bentonite (trade name: NK-KNP, Coseal), with 80.5 parts (80.5%w/w) mixing of purifying waste water, use DYNO mill (model: Typ KDL A) be ground into average grain diameter 2-3 μ, form suspending agent then.
The mixture of 10 parts of (10%w/w) herbicidal active components (A1 or A2)/herbicidal active component (B), 5 parts of (5%w/w) calcium dodecyl benzene sulfonate (trade names: CR-DBC64, Yusungwhayeontech), 2.5 part (2.5%w/w) ethoxylation (average EO addition molal quantity: 10) oleyl alcohol (trade name: Koremul OE10, Hannongwhasung), 2.5 part (2.5%w/w) ethoxylation (average EO addition molal quantity: 40) castor oil (trade name: Koremul CO40, Hannongwhasung), with alkyl benzene diluent naphtha (trade name: Kocosol 150, SKCorp.) use suitable blender evenly to mix, form missible oil.
Biological Examples
By active component (A1) or (A2) and one or more mixed processing that are selected from the active component (B) of (B1)-(B9) to estimate Herbicidal synergistic active and as described below to the method and the result thereof of the safety of crop.
1. greenhouse jar test
Seed or storage organ's part (brood body with monocotyledon weed (grass family and sedge family) and broadleaf weed (broad leaved weed); Stem tuber, stem etc.) sow or be transplanted in the sandy loam in the jar, then in suitable greenhouse growth conditions (temperature, air humidity and irrigation) growth down.For the test under the rice cropping condition, water keeps 3cm.Sowing or transplant a period of time after, when the growth of test plant arrives certain phase, it is handled with composition of the present invention.Under soil is executed situation, quantitative composition directly is applied to immersion soil.Under the situation of foliar spray, with the water of irrigating from wherein discharging, the quantitative composition of dilute with water then, and use CO
2Pressurization belt transmission sprayer (R﹠amp; D spray USA) is sprayed onto it on test plant, and the burst size of spray solution is 200-1000L/ha.Then, the plant of handling is remained in the greenhouse about 3-4 week under the standard greenhouse growth conditions.Visual assessment composition and untreated control compare the herbicide action of processed plant then.The herbicide action of composition is with % control of weeds rate record, compares with 0%-100% with untreated control and estimates.0% represents to weeds to no effect, and 100% expression weeds are dead fully.Each processing repeats to form by three or four times.
2. field trial
Crop is sowed or is transplanted under its field condition of growing usually, simultaneously, unifacial leaf and dicots seed or brood body (stem tuber, stem etc.) sowed or be transplanted to make its growth in the jar of placing in the field, or the weeds that make all even natural formation at field growing to certain vegetative stage.When the growths of these weeds reaches certain phase, use compositions-treated of the present invention.Under the situation that soil is executed, quantitative composition directly is applied to immersion soil.Under the situation of foliar spray, the composition that dilute with water is quantitative uses CO
2Add knapsack sprayer it is sprayed onto on the test plant, the burst size of dilute solution is 200-1000L/ha.Before foliar spray, the irrigation water in the rice field is discharged.After using the about 5-7 of composition week, herbicide action and the phytotoxicity compare with untreated control measured in range estimation, and use is identical in standard and the test of above-mentioned greenhouse jar.Each processing repeats to form by three or four times.
3. the evaluation of synergistic effect
Under the situation of using Herbicidal combinations of the present invention, its herbicide action to weeds surpasses the summation of the independent herbicide action when contained each herbicides compounds is sprayed separately in the present composition.Therefore, execute with each herbicides compounds list and to compare, composition of the present invention can provide identical with it weeds herbicide action under the low consumption of herbicides compounds.The reduction of the increase of this activity of weeding and effectiveness and active component consumption has convincingly demonstrated synergistic effect of the present invention.The evaluation of the synergistic effect that shows in mixed the executing to two or more herbicidal active components is based on " CalculationSynergistic and Antagonistic Response of Herbicide Combinations ", and (Weeds 15/1 (1967), and S.R.Colby) middle Colby ' the s method of describing is determined.
Therefore, use following formula for this reason:
E＝X+Y-(X×Y)/100
Wherein X represents the control of weeds (%) of weed killer herbicide A under X g active ingredient/ha consumption,
Y represents the control of weeds (%) of weed killer herbicide B under Y g active ingredient/ha consumption,
E is illustrated in the expection control of weeds (%) under X+Y g active ingredient/ha consumption.
If the control of weeds rate of observed reality surpasses the desired value (E) of using Colby ' s method to calculate in biologic test, then represent the summation of the effectiveness of Herbicidal combinations greater than each composition effectiveness, this means that composition has synergistic effect.
4. increase the evaluation of crop safety
Crop safety is by term " crop plants toxicity " statement, and this expression is to the infringement of crop, therefore to the phytotoxicity degree of crop low mean the safety of crop higher.The crop plants toxicity of Herbicidal combinations of the present invention is lower than the summation of the crop plants toxicity when contained each herbicides compounds sprays separately in the composition.Therefore, composition of the present invention has the crop safety higher than the composition that contains independent herbicidal active component, and therefore the crop plants toxicity that occurs when single component is used significantly reduces, and is enough to be used in target crop.The increase of described safety can be calculated by above-mentioned Colby ' s method.If the crop plants toxicity (%) of observed mixture reality is lower than the desired value (E) that has more the Colby method and calculate, this means that mixture has the phytotoxicity lower than the summation of each composition, promptly composition has synergy safety effectiveness.
The results are shown among the following table 1-26 of above-mentioned test.
Table 1
Compound (A1) and diclofop-methyl (B1.1) are to the herbicidal performance (passing through foliar spray) of the grassy weed annual bluegrass (Poa annua) in field
Table 2
Compound (A1) He oxazole acyl grass amine (B1.2) to the herbicidal performance (passing through foliar spray) of the grassy weed in field
Table 3
Compound (A1) and alkynes grass ester (B1.4) are to the herbicidal performance (passing through foliar spray) of the grassy weed annual bluegrass in field
Table 4
Compound (A1) and thifensulfuronmethyl (B2.1) are to the herbicidal performance (passing through foliar spray) of the broad leaved weed in field
Table 5
Compound (A1) and flupyrsulfuron-methyl-sodium (B2.9) are to the herbicidal performance (passing through foliar spray) of the big fringe amur foxtail of grassy weed in field
Table 6
In the greenhouse, compound (A1) and bensulfuron-methyl (B2.10) are to the herbicidal performance (executing by soil) of perennial weed Eleocharis kuroguwai
Table 7
In the greenhouse, compound (A1) and AC322140 (B2.11) are to the herbicidal performance (executing by soil) of perennial weed
Table 8
In the greenhouse, compound (A1) and cinosulfuron (B2.12) are to the herbicidal performance (executing by soil) of perennial weed Eleochariskuroguwai
Table 9
In the greenhouse, compound (A1) and azimsulfuron (B2.13) are to the herbicidal performance (executing by soil) of perennial weed
Table 10
In the greenhouse, compound (A1) and pyrazosulfuron (B2.15) are to the herbicidal performance (executing by soil) of perennial weed Cyperusserotinus
Table 11
In the field, compound (A1) and bentazone (B3.1) are to the herbicidal performance (executing by soil) of Eleocharis kuroguwai, barnyard grass and rice
Table 12
In the greenhouse, compound (A1) and symetryne (B3.5) are to the herbicidal performance (executing by soil) of sulfonylurea herbicide resistant weed
Table 13
In the field, compound (A1) and carfentrazoneethyl (B4.3) are to the herbicidal performance (passing through foliar spray) of main rice weeds and rice
Table 14
In the greenhouse, compound (A1) and carfentrazoneethyl (B4.3) are to the herbicidal performance (passing through foliar spray) of broad leaved weed Monochoria vaginalis
Table 15
On the meadow, compound (A1) and carfentrazoneethyl (B4.3) are to the herbicidal performance (passing through foliar spray) of main weeds Trifolium (white clover (Trifolium repens))
*DAA: the fate after the dispenser
Table 16
In the field, compound (A1) and carfentrazoneethyl (B4.3) are to the herbicidal performance (passing through foliar spray) of broad leaved weed
Table 17
In the greenhouse, compound (A1) and Huan Wu Evil humulone (B4.6) are to the herbicidal performance (executing by soil) of sulfonylurea herbicide resistant weed
Table 18
In the field, compound (A1) and diflufenican (B5.1) are to the herbicidal performance (passing through foliar spray) of broad leaved weed
Table 19
In the greenhouse, compound (A1) and pyrazolate (B5.5) are to the herbicidal performance (executing by soil) of sulfonylurea herbicide resistant weed.
Table 20
In the greenhouse, compound (A1) and butachlor (B6.1) are to the herbicidal performance (executing by soil) of sulfonylurea herbicide resistant weed.
Table 21
In the greenhouse, compound (A1) and benfuresate (B7.1) are to the herbicidal performance (executing by soil) of perennial weed Eleochariskuroguwai.
Table 22
In the greenhouse, compound (A1) and benthiocarb (B7.5) are to the herbicidal performance (executing by soil) of sulfonylurea herbicide resistant weed.
Table 23
In the field, compound (A1) and 2,4-D (B8.3) is to the herbicidal performance (passing through foliar spray) of broad leaved weed.
Table 24
In the greenhouse, compound (A1) and clomeprop (B8.7) are to the herbicidal performance (executing by soil) of sulfonylurea herbicide resistant weed.
Table 25
In the greenhouse, compound (A1) and dithiopyr (B9.2) are to the herbicidal performance (executing by soil) of sulfonylurea herbicide resistance Monochoria vaginalis.
Table 26
In the greenhouse, compound (A1) and dithiopyr (B9.2) are to the herbicidal performance (executing by soil) of sulfonylurea herbicide resistance Monochoria vaginalis.
Industrial applicibility
Execute with each herbicides compounds list and to compare, Herbicidal combinations of the present invention mixes the herbicide action with enhancing and the weeds of widening spectrum by the herbicides compounds that has different functions or different herbicide action with two kinds, because the synergistic effect therefore amount of used herbicidal constituents can reduce, reduce the control of weeds cost thereby therefore the labour can be saved by contained other herbicides compounds in co-administered flucetosulfuron and the Herbicidal combinations. In addition, contain formula (1) or (2) compound and one or more Herbicidal combinations that are selected from other herbicides of light compositing inhibitor bentazone, protogen IX oxidase inhibitor carfentrazoneethyl and auximone type herbicide and have synergistic effect, strengthened the activity of weeding to perennial weeds and sulfonylureas resistant weed, can solve the grassy weed antagonism of barnyard grass particularly, and can increase foliar spray to the security of rice.
Claims (8)
1. Herbicidal combinations contains the compound of following formula (1), i.e. herbicidal active component (A1);
Be selected from other active components of (B) group with one or more, described (B) group is by (B1.1) diclofop-methyl and ester thereof, () oxazole acyl grass amine B1.2, (B1.3) cyhalofop-butyl, (B1.4) alkynes grass ester and (B1.5) Gao oxazole diclofop-methyl and ester composition thereof, wherein active components A 1 is 1 with the weight ratio of active component B: 100-20: 1.
2. Herbicidal combinations contains the compound of following formula (2), i.e. herbicidal active component (A2);
Be selected from the active component of the group (B) that defines as claim 1 with one or more,
Wherein active components A 2 is 1 with the weight ratio of active component B: 100-20: 1.
3. Herbicidal combinations as claimed in claim 1 or 2 also contains the composition that one or more are selected from carrier, surfactant and additive.
4. a controlling weeds method comprises to crop field or non-crop belts and uses claim 1 or 2 described Herbicidal combinations.
5. a method of controlling weeds comprises to rice culture and uses claim 1 or 2 described Herbicidal combinations.
6. a method of controlling weeds comprises to grain husbandry and uses claim 1 or 2 described Herbicidal combinations.
7. a method of controlling weeds comprises to meadow or pasture and uses claim 1 or 2 described Herbicidal combinations.
8. method as claimed in claim 4, Herbicidal combinations is wherein handled by foliar spray.
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| CN2009102042065A Division CN101675739B (en) | 2004-12-17 | 2005-12-16 | Synergistic herbicidal compositions |
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| CN102657207A (en) * | 2012-04-18 | 2012-09-12 | 联保作物科技有限公司 | Weeding composition |
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| JP4834361B2 (en) * | 2004-09-17 | 2011-12-14 | 石原産業株式会社 | Herbicidal composition |
| JP4966529B2 (en) * | 2004-09-17 | 2012-07-04 | 石原産業株式会社 | Herbicidal composition |
| US20070232492A1 (en) * | 2004-09-17 | 2007-10-04 | Ishihara Sangyo Kaisha, Ltd. | Herbicidal Composition |
| JP4914154B2 (en) * | 2005-09-15 | 2012-04-11 | 石原産業株式会社 | Herbicidal composition |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN102657207A (en) * | 2012-04-18 | 2012-09-12 | 联保作物科技有限公司 | Weeding composition |
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| CN109077059A (en) | 2018-12-25 |
| WO2006065094A1 (en) | 2006-06-22 |
| CN106689174B (en) | 2019-11-19 |
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| KR101280059B1 (en) | 2013-06-28 |
| JP4625089B2 (en) | 2011-02-02 |
| CN101675739A (en) | 2010-03-24 |
| CN103081936A (en) | 2013-05-08 |
| KR20060069304A (en) | 2006-06-21 |
| CN104522018A (en) | 2015-04-22 |
| JP2008524206A (en) | 2008-07-10 |
| CN106689174A (en) | 2017-05-24 |
| BRPI0519121B1 (en) | 2017-01-24 |
| CN101102671A (en) | 2008-01-09 |
| CN101675739B (en) | 2013-01-02 |
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