WO2007079965A2 - A herbicide composition for paddy field - Google Patents

A herbicide composition for paddy field Download PDF

Info

Publication number
WO2007079965A2
WO2007079965A2 PCT/EP2006/012502 EP2006012502W WO2007079965A2 WO 2007079965 A2 WO2007079965 A2 WO 2007079965A2 EP 2006012502 W EP2006012502 W EP 2006012502W WO 2007079965 A2 WO2007079965 A2 WO 2007079965A2
Authority
WO
WIPO (PCT)
Prior art keywords
weight
parts
methyl
herbicide
paddy field
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Ceased
Application number
PCT/EP2006/012502
Other languages
French (fr)
Other versions
WO2007079965A3 (en
Inventor
Keiji Endo
Shinichi Shirakura
Shin Nakamura
Natsuko Minegishi
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Bayer CropScience AG
Original Assignee
Bayer CropScience AG
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Bayer CropScience AG filed Critical Bayer CropScience AG
Priority to DE602006021802T priority Critical patent/DE602006021802D1/en
Priority to AT06841143T priority patent/ATE507719T1/en
Priority to BRPI0621576-9A priority patent/BRPI0621576A2/en
Priority to EP06841143A priority patent/EP1976384B1/en
Publication of WO2007079965A2 publication Critical patent/WO2007079965A2/en
Anticipated expiration legal-status Critical
Publication of WO2007079965A3 publication Critical patent/WO2007079965A3/en
Ceased legal-status Critical Current

Links

Classifications

    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • 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
    • 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
    • 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
    • A01N25/00—Biocides, pest repellants or attractants, or plant growth regulators, characterised by their forms, or by their non-active ingredients or by their methods of application, e.g. seed treatment or sequential application; Substances for reducing the noxious effect of the active ingredients to organisms other than pests
    • A01N25/32—Ingredients for reducing the noxious effect of the active substances to organisms other than pests, e.g. toxicity reducing compositions, self-destructing compositions
    • 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
    • A01N43/64—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with three nitrogen atoms as the only ring hetero atoms
    • A01N43/66—1,3,5-Triazines, not hydrogenated and not substituted at the ring nitrogen atoms
    • 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
    • A01N43/64—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with three nitrogen atoms as the only ring hetero atoms
    • A01N43/66—1,3,5-Triazines, not hydrogenated and not substituted at the ring nitrogen atoms
    • A01N43/68—1,3,5-Triazines, not hydrogenated and not substituted at the ring nitrogen atoms with two or three nitrogen atoms directly attached to ring carbon atoms
    • A01N43/70—Diamino—1,3,5—triazines with only one oxygen, sulfur or halogen atom or only one cyano, thiocyano (—SCN), cyanato (—OCN) or azido (—N3) group directly attached to a ring carbon atom

Definitions

  • the present invention relates to a herbicide composition for paddy field. More specifically the present invention relates to a herbicide composition for paddy field containing a herbicidal difluoromethanesulfonamide derivative and a certain kind of known herbicidal compound as effective components.
  • X represents a halogen
  • Y represents CH or N
  • R 1 represents hydrogen
  • R 2 represents hydrogen or hydroxy
  • composition mentioned below shows an outstandingly excellent and desirable effect in terms of weed controlling in paddy field and phytotoxicity to rice.
  • the present invention provides a herbicide composition for paddy field characterized by comprising a combination of components (a), (b) and/or (c), wherein (a) is one or more difluoromethanesulfonamide derivative represented by the formula
  • X represents a halogen
  • Y represents CH or N
  • R 1 represents hydrogen
  • R 2 represents hydrogen or hydroxy
  • (b) is one or more herbicidal compounds selected from the group consisting of pretilachlor, butachlor, alachlor, metolachlor, acetochlor, clomeprop, bromobutide, benfuresate, indanofan, pyrazolate, benzofenap, pyrazoxyfen, pyraclonil, oxaziclomefone, bensulfuron-methyl, azimsulfuron, imazosulfuron, pyrazosulfuron-ethyl, cyclosulfamuron, ethoxysulfuron, halosulfuron-methyl, orthosulfamuron, cinosulfuron, metsulfuron-methyl, penoxsulam, thiobencarb, pyributycarb, molinate, dimethametryn, simetryn, cafenstrole
  • (c) is, as a safener, one or more compounds selected from the group consisting of dymron, isoxadifen(-ethyl), flurazole, fenchlorazole-ethyl, fenclorim, cloquintocet-mexyl, oxabetrinil, fluxofenim, mefenpyr-diethyl, furilazole, R-29148 (code no.), benoxacor, dichlormid and dicyclonone as effective components.
  • composition of the present invention surprisingly, a substantially higher herbicidal effect (synergistic effect) than the sum of the effect of each active compound by each single application is shown, compared with the case that each active compound is used each singly.
  • a broad herbicidal spectrum can be obtained and the application period can be broadened.
  • the paddy rice culture for example, it shows excellent herbicidal effect when applied any time from the early stage of weed development just after the transplantation to growing period. In addition, the effect maintains for a long period.
  • an excellent herbicidal effect with an excellent residual effect and no phytotoxicity to rice is obtained.
  • X represents fluorine or chlorine
  • Y represents CH or N
  • R 1 represents hydrogen
  • R 2 represents hydrogen or hydroxy
  • the herbicidal compounds (b) used in combination with the compound (a) of the above-mentioned formula (I) are as aforementioned, and as their preferable examples there can be mentioned (b-1) anilofos, (b-2) pretilachlor, (b-3) cafenstrole, (b-4) cyhalofop-butyl, (b-5) penoxsulam, (b-6) pyraclonil, (b-7) bispyribac-sodium, (b-8) fentrazamide, (b-9) mefenacet, (b-10) oxaziclomefone, (b-11 ) benfuresate, (b-12) bensulfuron-methyl, (b-13) ethoxysulfuron, (b-14) bromobutide and (b-15) AVH301.
  • herbicidal compounds (b) can be used, each singly or in combination of two kinds or more, as a mixture with a compound (a) of the formula (I).
  • the compounds (c) as safener used in combination with the compound (a) of the above-mentioned formula (I) according to the present invention are as aforementioned, and as their preferable examples there can be mentioned (c-1 ) dymron, (c-2) mefenpyr-diethyl, (c-3) isoxadifen and (c-4) isoxadifen-ethyl.
  • the above-mentioned compounds (c) as safener can be used, each singly or in combination of two kinds or more, as a mixture with a compound (a) of the formula (I).
  • the above-mentioned herbicidal compounds (b) and the compounds (c) as safener are described in, for example, The Pesticide Manual, 13 th edition (published by British Crop Protection Council, 2003) or "Compendium of Pesticide Common Names" accessible e.g. from the Internet.
  • the compound having the code number AVH 301 is a herbicide having the chemical name 2- ⁇ 2-chloro-4-mesyl-3- [(tetrahydrofuran-2-ylmethoxy)-methyl]-benzoyl ⁇ - cyclohexan-1 ,3-dione, also known under the common name "tefuryltrione".
  • the compound having the code number R-29148 is a safener having the chemical name 3-(dichloroacetyl)-2,2,5-trimethyl- oxazolidine known from DE-A-02350800.
  • the mixing ratio of a compound (a) of the formula (I) and a herbicidal compound (b) can be varied in a relatively wide range according to the kind, application period, application place, application method, etc. of said composition.
  • at least one herbicidal compounds (b) in the range of 0.05-200 parts by weight, preferably 0.1-100 parts by weight can be used to 1 part by weight of a compound (a) of the formula (I).
  • individual usage ratio of herbicidal compounds (b) to 1 part by weight of a compound (a) of the formula (I) there can be mentioned the following.
  • the mixing ratio of a compound (a) of the formula (I) and a compound (c) as safener can be varied in a relatively wide range according to the kind, application period, application place, application method, etc. of said composition.
  • at least one compounds (c) as safener in the range of 0.05-200 parts by weight, preferably 0.2-100 parts by weight can be used to 1 part by weight of a compound (a) of the formula (I).
  • a compound (a) of the formula (I) there can be mentioned the following.
  • composition of the present invention shows a strong controlling effect against paddy field weeds and therefore said composition can be used as a herbicide composition for paddy field, particularly a selective herbicide for paddy rice.
  • An object of the invention is thus the use of a combination of herbicide (a) and herbicide (b) or safener (c) or a combination of components (a) + (b) + (c) for controlling weeds in a paddy field, optionally in the presence of a crop of useful plants, particularly rice plants.
  • the components can be applied to the paddy field and its weed plants in sequential manner or simultaneously.
  • Another object of the invention is thus the method wherein the components (a), (b) and/or (c) are applied accordingly.
  • composition of the present invention can be used against various kinds of weeds developing in the paddy field. As their examples there can be mentioned the following:
  • Dicotyledonous plants of the following Genera Polygonum, Rorippa, Rotala, Lindemia, Bidens, Dopatrium, Eclipta, Elatine, Gratiola, Lindemia, Ludwigia, Oenanthe, Ranunculus, Deinostema, etc.
  • Monocotyledonous plants of the following Genera Echinochloa, Panicum, Poa, Cyperus, Monochoria, Fimbristylis, Sagittaria, Eleocharis, Scirpus, Alisma, Aneilema, Blyxa, Eriocaulon, Potamogeton, etc.
  • composition of the present invention can be used, more specifically for example, in relation to the following typical paddy field weeds.
  • composition of the present invention should not be restricted to these weeds in any way, but can be applied against other weeds in the same manner.
  • composition of the present invention can be made into customary formulation forms in case of using for control of paddy field weeds.
  • formulation forms there can be mentioned, for example, solutions, emulsions, wettable powders, suspensions, powders, soluble powders, granules, suspo-emulsion concentrates, solid formulations (jumbo formulations), floating granules, microcapsules in polymer substance, etc.
  • formulations can be prepared according to per se known methods.
  • the formulations according to the present invention can be prepared, for example, by mixing the aforementioned compound (a) of the formula (I), herbicidal compound (b) and/or compound (c) with extenders, namely liquid diluents and/or solid diluents, and, in case of necessity, by using surfactants, namely emulsifiers and/or dispersants and/or foam-forming agents.
  • organic solvents can be used as auxiliary solvent.
  • organic solvents such as aromatic hydrocarbons (for example, xylene, toluene, alkylnaphthalene, etc.), chlorinated aromatic or chlorinated aliphatic hydrocarbons (for example, chlorobenzenes, ethylene chlorides, methylene chloride, etc.), aliphatic hydrocarbons [for example, cyclohexane etc. or paraffins (for example, mineral oil fractions, mineral oils, vegetable oils, etc.)], alcohols (for example, butanol, glycols, etc.
  • aromatic hydrocarbons for example, xylene, toluene, alkylnaphthalene, etc.
  • chlorinated aromatic or chlorinated aliphatic hydrocarbons for example, chlorobenzenes, ethylene chlorides, methylene chloride, etc.
  • aliphatic hydrocarbons for example, cyclohexane etc. or paraffins (for example, mineral oil fractions,
  • ketones for example, acetone, methyl ethyl ketone, methyl isobutyl ketone, cyclohexanone, etc.
  • strongly polar solvents for example, dimethylformamide, dimethyl sulfoxide, etc.
  • solid diluents there can be mentioned, for example, ammonium salts, ground natural minerals (for example, kaolin, clay, talc, chalk, quartz, attapulgite, montmorillonite, diatomaceous earth, etc.), ground synthetic minerals (for example, highly dispersed silicic acid, alumina, silicates, etc.) etc.
  • ground natural minerals for example, kaolin, clay, talc, chalk, quartz, attapulgite, montmorillonite, diatomaceous earth, etc.
  • ground synthetic minerals for example, highly dispersed silicic acid, alumina, silicates, etc.
  • solid carriers for powders there can be used, for example, crushed and fractionated rocks (for example, calcite, marble, pumice, sepiolite, dolomite, etc.) synthetic granules of inorganic and organic meals, particles of organic materials (for example, saw dust, coconut shells, maize cobs, tobacco stalks, etc.) etc.
  • nonionic or anionic emulsifiers for example, polyoxyethylene fatty acid esters, polyoxyethylene fatty alcohol ethers (for example, alkylaryl polyglycol ethers, alkylsulfonates, alkylsulfates, arylsulfonates, etc.)], albumin hydrolysis products, etc.
  • dispersants for example, lignin sulfite waste liquor, methyl cellulose, etc. are adequate.
  • Tackifiers can also be used in formulations (powders, granules, emulsifiable concentrates).
  • tackifiers there can be mentioned, for example, carboxymethyl cellulose, natural and synthetic polymers (for example, gum Arabic, polyvinyl alcohol, polyvinyl acetates, etc.) natural phospholipids (for example, cephalins or recithins), synthetic phospholipids, etc.
  • mineral oils and vegetable oils can be used as additives.
  • Colorants can also be used.
  • inorganic pigments for example, iron oxide, titanium oxide, Prussian Blue, etc.
  • organic dyestuffs such as alizarin dyestuffs, azo dyestuffs or metal phthalocyanine dyestuffs
  • nutrients such as salts of iron, manganese, boron, copper, cobalt, molybdenum or zinc.
  • the formulations can contain the total of the compound of the formula (I) (a), herbicidal compound (b) and/or compound (c) at a concentration in the range of generally 0.1 -95 % by weight, preferably 0.5-90 % by weight.
  • composition of the present invention can be used for controlling weeds as themselves or in their formulation forms. It is also possible to do tank mixing at the time of application and further to contain other known active compounds, particularly active compounds generally used in the paddy field, for example, fungicides, insecticides, plant growth regulators, plant nutrients, soil improving agents, etc.
  • composition of the present invention can be used as such or in their formulation forms or in application forms prepared by further diluting said formulations, for example, in the forms of ready-to-use solutions, emulsifiable concentrates, suspensions, powders, wettable powders or granules.
  • Formulations of these forms can be applied to paddy field by usual methods, for example, watering, spraying, atomizing, dusting, granule spreading, etc.
  • composition of the present invention can be applied to the paddy field before, at the time and after the transplantation.
  • the amount of said composition to be applied can be varied in a substantial range.
  • the amount can be in the range of, for example, 0.01-5 kg/ha, preferably 0.06-4.5 kg/ha as the total amount of the compound of the formula (I) (a), herbicidal compound (b) and/or compound (c).
  • Surfactant Benzyloxy polyglycol ether 1 part by weight The above-mentioned carrier and surfactant and 1 part by weight of active compounds(component (a) and component (b) or component (c)) are mixed and the obtained formulations are diluted with water to prepare the test agents of the prescribed chemicals amount (preparations).
  • Test example 1 Test of effect of the herbicide composition against paddy field weeds
  • results are shown in Table 1 - Table 3.
  • MOOVP Monochoria vaginalis Presl
  • BBBBB annual broad-leaves
  • CYPSE Cyperus serotinus Rottboel
  • SAGPY Sagittaria pygmaea
  • Test example 2 Test of effect of phytotoxicity reduction ⁇ Test method>
  • a mixture of 4 parts by weight of the active compound (a-1 ), 4 parts by weight of the active compound (b-3), 10 parts by weight of ethylene glycol, 3 parts by weight of polyoxyalkylene tristyrylphenyl ether, 10 parts by weight of xanthan gum, 0.5 parts by weight of 14% silicone oil emulsion and 68.5 parts by weight of water is well stirred and then crushed with a crusher (Dyno-Mill Type KDL) to obtain water suspension formulation.
  • the herbicide composition for paddy field of the present invention shows, as shown in the aforementioned test examples, precise controlling effect against various kinds of paddy field weeds and an excellent residual effect.

Landscapes

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

Abstract

A herbicide composition for paddy field characterized by containing (a) a herbicidal difluoromethanesulfonamide derivative represented by the formula (I) and (b) at least one herbicidal compound selected from the group consisting of pretilachlor, butachlor, alachlor, metolachlor, acetochlor, clomeprop, bromobutide, benfuresate, indanofan, pyrazolate, benzofenap, pyrazoxyfen, pyraclonil, oxaziclomefone, bensulfuron-methyl, azimsulfuron, imazosulfuron, pyrazosulfuron-ethyl, cyclosulfamuron, ethoxysulfuron, halosulfuron-methyl, orthosulfamuron, cinosulfuron, metsulfuron-methyl, penoxsulam, thiobencarb, pyributycarb, molinate, dimethametryn, simetryn, cafenstrole, quinclorac, anilofos, mefenacet, fentrazamide, pentoxazone, oxadiargyl, oxadiazon, benzobicyclon, mesotrione, AVH301 (code no.), cyhalof op-butyl, metamifop, bispyribac-sodium, pyriftalid, pyrimisulfan, pyrimenobac-methyl, chlormethoxynil, oxyfluorfen, dithiopyr, MCPA, MCPB, 2,4-D, dymron, cumyluron, quinoclamine and clomazone, and/or (c) one or more compounds selected from the group consisting of safeners dymron, isoxadifen(-ethyl), flurazole, fenchlorazole-ethyl, fenclorim, cloquintocet-mexyl, oxabetrinil, fluxofenim, mefenpyr-diethyl, furilazole, R-29148 (code no.), benoxacor, dichlormid and dicyclonone as effective components.

Description

Description
A herbicide composition for paddy field
The present invention relates to a herbicide composition for paddy field. More specifically the present invention relates to a herbicide composition for paddy field containing a herbicidal difluoromethanesulfonamide derivative and a certain kind of known herbicidal compound as effective components.
Difluoromethanesulfonamide derivatives represented by the formula
Figure imgf000002_0001
wherein
X represents a halogen,
Y represents CH or N, R1 represents hydrogen, and
R2 represents hydrogen or hydroxy, or
R1 and R2 together may form C=O with the carbon atom to which they are bonding, are known compounds (WO-A-2005/096818). Some of these derivatives show good controlling effect against paddy field weeds. Sometimes in the practical usage, however, contrary to expectation, they do not show a fully satisfactory herbicidal effect and phytotoxicity to paddy rice is observed. In the practical usage, it is practically difficult to provide a single active compound with such properties as to correspond to various kinds of usage, as there are many potential elements influencing the herbicidal effect. Particularly, depending upon the kinds of weeds to be controlled, the conditions of their developing area, etc., the effect of an active compound is different. In addition, considering the cost reduction in agricultural production, influence on environment, etc., development of an agent showing effective action with less application amount is strongly desired.
In order to fulfill such a desire, as one of the methods to improve properties of a herbicide, it is often practiced to use it after mixing it with other active compounds. By using such a mixture, however, an expected effect is not necessarily obtained quite often, due to, for example, decomposition of active compounds, antagonistic action of effects, etc.
The present inventors, found, this time, that the composition mentioned below shows an outstandingly excellent and desirable effect in terms of weed controlling in paddy field and phytotoxicity to rice.
Thus, the present invention provides a herbicide composition for paddy field characterized by comprising a combination of components (a), (b) and/or (c), wherein (a) is one or more difluoromethanesulfonamide derivative represented by the formula
Figure imgf000003_0001
wherein X represents a halogen, Y represents CH or N,
R1 represents hydrogen, and
R2 represents hydrogen or hydroxy, or
R1 and R2 together may form C=O with the carbon atom to which they are bonding, (b) is one or more herbicidal compounds selected from the group consisting of pretilachlor, butachlor, alachlor, metolachlor, acetochlor, clomeprop, bromobutide, benfuresate, indanofan, pyrazolate, benzofenap, pyrazoxyfen, pyraclonil, oxaziclomefone, bensulfuron-methyl, azimsulfuron, imazosulfuron, pyrazosulfuron-ethyl, cyclosulfamuron, ethoxysulfuron, halosulfuron-methyl, orthosulfamuron, cinosulfuron, metsulfuron-methyl, penoxsulam, thiobencarb, pyributycarb, molinate, dimethametryn, simetryn, cafenstrole, quinclorac, anilofos, mefenacet, fentrazamide, pentoxazone, oxadiargyl, oxadiazon, benzobicyclon, mesotrione, AVH301 (code no.), cyhalofop-butyl, metamifop, bispyribac-sodium, pyriftalid, pyrimisulfan, pyrimenobac-methyl, chlormethoxynil (chlomethoxyfen), oxyfluorfen, dithiopyr, MCPA, MCPB, 2,4-D, dymron, cumyluron, quinoclamine and clomazone, and
(c) is, as a safener, one or more compounds selected from the group consisting of dymron, isoxadifen(-ethyl), flurazole, fenchlorazole-ethyl, fenclorim, cloquintocet-mexyl, oxabetrinil, fluxofenim, mefenpyr-diethyl, furilazole, R-29148 (code no.), benoxacor, dichlormid and dicyclonone as effective components.
In the following the compounds of components (a), (b) and (c) are also named compounds (a), (b) or (c), respectively. The components (a), (b) and (c) are also shortly named compound (a), (b) or (c) respectively.
By the above-mentioned composition of the present invention, surprisingly, a substantially higher herbicidal effect (synergistic effect) than the sum of the effect of each active compound by each single application is shown, compared with the case that each active compound is used each singly. As a result, in case of controlling weeds, it is possible to substantially reduce the concentration of each substance used by now. At the same time, by said composition a broad herbicidal spectrum can be obtained and the application period can be broadened. In the paddy rice culture, for example, it shows excellent herbicidal effect when applied any time from the early stage of weed development just after the transplantation to growing period. In addition, the effect maintains for a long period. Thus, an excellent herbicidal effect with an excellent residual effect and no phytotoxicity to rice is obtained.
In the compound (a) of the formula (I) in the composition of the present invention, preferably X represents fluorine or chlorine, Y represents CH or N, R1 represents hydrogen, and R2 represents hydrogen or hydroxy, or R1 and R2 together may form C=O with the carbon atom to which they are bonding.
As preferable examples of the compound (a) of the formula (I) in the composition of the present invention there can be mentioned the following shown in the Table A mentioned below.
Table A
Figure imgf000005_0001
Figure imgf000006_0001
These compounds can be used each singly or in combination of two kinds or more.
In the composition of the present invention, the herbicidal compounds (b) used in combination with the compound (a) of the above-mentioned formula (I) are as aforementioned, and as their preferable examples there can be mentioned (b-1) anilofos, (b-2) pretilachlor, (b-3) cafenstrole, (b-4) cyhalofop-butyl, (b-5) penoxsulam, (b-6) pyraclonil, (b-7) bispyribac-sodium, (b-8) fentrazamide, (b-9) mefenacet, (b-10) oxaziclomefone, (b-11 ) benfuresate, (b-12) bensulfuron-methyl, (b-13) ethoxysulfuron, (b-14) bromobutide and (b-15) AVH301.
The above-mentioned herbicidal compounds (b) can be used, each singly or in combination of two kinds or more, as a mixture with a compound (a) of the formula (I).
The compounds (c) as safener used in combination with the compound (a) of the above-mentioned formula (I) according to the present invention are as aforementioned, and as their preferable examples there can be mentioned (c-1 ) dymron, (c-2) mefenpyr-diethyl, (c-3) isoxadifen and (c-4) isoxadifen-ethyl. The above-mentioned compounds (c) as safener can be used, each singly or in combination of two kinds or more, as a mixture with a compound (a) of the formula (I).
The above-mentioned herbicidal compounds (b) and the compounds (c) as safener are described in, for example, The Pesticide Manual, 13th edition (published by British Crop Protection Council, 2003) or "Compendium of Pesticide Common Names" accessible e.g. from the Internet. The compound having the code number AVH 301 is a herbicide having the chemical name 2-{2-chloro-4-mesyl-3- [(tetrahydrofuran-2-ylmethoxy)-methyl]-benzoyl}- cyclohexan-1 ,3-dione, also known under the common name "tefuryltrione". The compound having the code number R-29148 is a safener having the chemical name 3-(dichloroacetyl)-2,2,5-trimethyl- oxazolidine known from DE-A-02350800.
In the composition of the present invention, the mixing ratio of a compound (a) of the formula (I) and a herbicidal compound (b) can be varied in a relatively wide range according to the kind, application period, application place, application method, etc. of said composition. Generally, at least one herbicidal compounds (b) in the range of 0.05-200 parts by weight, preferably 0.1-100 parts by weight can be used to 1 part by weight of a compound (a) of the formula (I). Specifically, as good examples of individual usage ratio of herbicidal compounds (b) to 1 part by weight of a compound (a) of the formula (I) there can be mentioned the following.
Anilofos (b-1 ): 0.5-50 parts by weight, preferably 1-20 parts by weight, Pretilachlor (b-2): 0.5-50 parts by weight, preferably 1-20 parts by weight, Cafenstrole (b-3): 0.5-50 parts by weight, preferably 1 -20 parts by weight,
Cyhalofop-butyl (b-4): 0.3-30 parts by weight, preferably 0.5-10 parts by weight, Penoxsulam (b-5): 0.2-10 parts by weight, preferably 1 -5 parts by weight, Pyraclonil (b-6): 0.5-50 parts by weight, preferably 1 -20 parts by weight, Bispyribac-sodium (b-7): 0.1-10 parts by weight, preferably 0.2-5 parts by weight, Fentrazamide (b-8): 0.5-50 parts by weight, preferably 1 -20 parts by weight, Mefenacet (b-9): 2-200 parts by weight, preferably 5-50 parts by weight, Oxaziclomefone (b-10): 0.2-10 parts by weight, preferably 1 -5 parts by weight, Benfuresate (b-11 ): 0.5-50 parts by weight, preferably 1 -20 parts by weight, Bensulfuron-methyl (b-12): 0.1 -10 parts by weight, preferably 0.2-5 parts by weight, Ethoxysulfuron (b-13): 0.1 -10 parts by weight, preferably 0.2-5 parts by weight, Bromobutide (b-14): 2-200 parts by weight, preferably 5-50 parts by weight, AVH301 (b-15): 0.5-50 parts by weight, preferably 1-30 parts by weight.
In the composition of the present invention, the mixing ratio of a compound (a) of the formula (I) and a compound (c) as safener can be varied in a relatively wide range according to the kind, application period, application place, application method, etc. of said composition. Generally, at least one compounds (c) as safener in the range of 0.05-200 parts by weight, preferably 0.2-100 parts by weight can be used to 1 part by weight of a compound (a) of the formula (I). Specifically, as good examples of individual usage ratio of compounds (c) to 1 part by weight of a compound (a) of the formula (I) there can be mentioned the following.
Dymron (c-1): 0.5-100 parts by weight, preferably 1 -20 parts by weight, Mefenpyr-diethyl (c-2): 0.05-10 parts by weight, preferably 0.5-5 parts by weight, Isoxadifen (c-3): 0.05-10 parts by weight, preferably 0.5-5 parts by weight, Isoxadifen-ethyl (c-4): 0.05-10 parts by weight, preferably 0.5-5 parts by weight.
The composition of the present invention shows a strong controlling effect against paddy field weeds and therefore said composition can be used as a herbicide composition for paddy field, particularly a selective herbicide for paddy rice.
An object of the invention is thus the use of a combination of herbicide (a) and herbicide (b) or safener (c) or a combination of components (a) + (b) + (c) for controlling weeds in a paddy field, optionally in the presence of a crop of useful plants, particularly rice plants. The components can be applied to the paddy field and its weed plants in sequential manner or simultaneously. Another object of the invention is thus the method wherein the components (a), (b) and/or (c) are applied accordingly.
The composition of the present invention can be used against various kinds of weeds developing in the paddy field. As their examples there can be mentioned the following:
Dicotyledonous plants of the following Genera: Polygonum, Rorippa, Rotala, Lindemia, Bidens, Dopatrium, Eclipta, Elatine, Gratiola, Lindemia, Ludwigia, Oenanthe, Ranunculus, Deinostema, etc.
Monocotyledonous plants of the following Genera: Echinochloa, Panicum, Poa, Cyperus, Monochoria, Fimbristylis, Sagittaria, Eleocharis, Scirpus, Alisma, Aneilema, Blyxa, Eriocaulon, Potamogeton, etc.
The composition of the present invention can be used, more specifically for example, in relation to the following typical paddy field weeds.
Dicotyledonous plants
Rotala indica Koehne
Lindemia procumbens Philcox
Ludwigia prostrata Roxburgh
Potamogeton distinctus A. Benn Elatine triandra Schk
Oenanthe javanica
Monocotyledonous plants
Echinochloa oryzicola Vasing
Monochoria vaginalis Presl Eleocharis acicularis L.
Eleocharis Kuroguwai Ohwi
Cyperus difformis L.
Cyperus serotinus Rottboel
Sagittaria pygmaea Miq Alisma canaliculatum A. Br. et Bouche
Scirpus juncoides Roxburgh The use of the composition of the present invention, however, should not be restricted to these weeds in any way, but can be applied against other weeds in the same manner.
The composition of the present invention can be made into customary formulation forms in case of using for control of paddy field weeds. As such formulation forms there can be mentioned, for example, solutions, emulsions, wettable powders, suspensions, powders, soluble powders, granules, suspo-emulsion concentrates, solid formulations (jumbo formulations), floating granules, microcapsules in polymer substance, etc.
These formulations can be prepared according to per se known methods. The formulations according to the present invention can be prepared, for example, by mixing the aforementioned compound (a) of the formula (I), herbicidal compound (b) and/or compound (c) with extenders, namely liquid diluents and/or solid diluents, and, in case of necessity, by using surfactants, namely emulsifiers and/or dispersants and/or foam-forming agents.
In case of using water as extender, for example, organic solvents can be used as auxiliary solvent. As liquid diluents there can be mentioned, for example, organic solvents such as aromatic hydrocarbons (for example, xylene, toluene, alkylnaphthalene, etc.), chlorinated aromatic or chlorinated aliphatic hydrocarbons (for example, chlorobenzenes, ethylene chlorides, methylene chloride, etc.), aliphatic hydrocarbons [for example, cyclohexane etc. or paraffins (for example, mineral oil fractions, mineral oils, vegetable oils, etc.)], alcohols (for example, butanol, glycols, etc. and their ethers, esters, etc.) ketones (for example, acetone, methyl ethyl ketone, methyl isobutyl ketone, cyclohexanone, etc.), strongly polar solvents (for example, dimethylformamide, dimethyl sulfoxide, etc.), and water.
As solid diluents there can be mentioned, for example, ammonium salts, ground natural minerals (for example, kaolin, clay, talc, chalk, quartz, attapulgite, montmorillonite, diatomaceous earth, etc.), ground synthetic minerals (for example, highly dispersed silicic acid, alumina, silicates, etc.) etc. As solid carriers for powders there can be used, for example, crushed and fractionated rocks (for example, calcite, marble, pumice, sepiolite, dolomite, etc.) synthetic granules of inorganic and organic meals, particles of organic materials (for example, saw dust, coconut shells, maize cobs, tobacco stalks, etc.) etc.
As emulsifiers and/or foaming agents there can be mentioned nonionic or anionic emulsifiers [for example, polyoxyethylene fatty acid esters, polyoxyethylene fatty alcohol ethers (for example, alkylaryl polyglycol ethers, alkylsulfonates, alkylsulfates, arylsulfonates, etc.)], albumin hydrolysis products, etc.
As dispersants, for example, lignin sulfite waste liquor, methyl cellulose, etc. are adequate.
Tackifiers can also be used in formulations (powders, granules, emulsifiable concentrates). As said tackifiers there can be mentioned, for example, carboxymethyl cellulose, natural and synthetic polymers (for example, gum Arabic, polyvinyl alcohol, polyvinyl acetates, etc.) natural phospholipids (for example, cephalins or recithins), synthetic phospholipids, etc. Further, as additives, mineral oils and vegetable oils can be used.
Colorants can also be used. As said colorants there can be mentioned inorganic pigments (for example, iron oxide, titanium oxide, Prussian Blue, etc,), organic dyestuffs such as alizarin dyestuffs, azo dyestuffs or metal phthalocyanine dyestuffs, and further traces nutrients such as salts of iron, manganese, boron, copper, cobalt, molybdenum or zinc.
The formulations can contain the total of the compound of the formula (I) (a), herbicidal compound (b) and/or compound (c) at a concentration in the range of generally 0.1 -95 % by weight, preferably 0.5-90 % by weight.
The composition of the present invention can be used for controlling weeds as themselves or in their formulation forms. It is also possible to do tank mixing at the time of application and further to contain other known active compounds, particularly active compounds generally used in the paddy field, for example, fungicides, insecticides, plant growth regulators, plant nutrients, soil improving agents, etc.
The composition of the present invention can be used as such or in their formulation forms or in application forms prepared by further diluting said formulations, for example, in the forms of ready-to-use solutions, emulsifiable concentrates, suspensions, powders, wettable powders or granules. Formulations of these forms can be applied to paddy field by usual methods, for example, watering, spraying, atomizing, dusting, granule spreading, etc.
The composition of the present invention can be applied to the paddy field before, at the time and after the transplantation. The amount of said composition to be applied can be varied in a substantial range. The amount can be in the range of, for example, 0.01-5 kg/ha, preferably 0.06-4.5 kg/ha as the total amount of the compound of the formula (I) (a), herbicidal compound (b) and/or compound (c).
Excellent results of the composition of the present invention will be described more specifically by the following examples. The present invention, however, should not be restricted only to them in any way.
Biological test examples and formulation examples
<Test compounds> Component (a) (a-1 ): compound No. 1 (ref: the aforementioned Table A)
(a-2): compound No. 3 (same as above) (a-3): compound No. 11 (same as above)
Component (b) the aforementioned (b-1 ) - (b-15)
Component (c) the aforementioned (c-1 ) - (c-3) Preparation of test agents>
Carrier: Acetone 5 parts by weight
Surfactant: Benzyloxy polyglycol ether 1 part by weight The above-mentioned carrier and surfactant and 1 part by weight of active compounds(component (a) and component (b) or component (c)) are mixed and the obtained formulations are diluted with water to prepare the test agents of the prescribed chemicals amount (preparations).
Test example 1 : Test of effect of the herbicide composition against paddy field weeds
<Test method>
In a green house, seeds or tubers of Monochoria vaginalis Presl, annual broad-leaves {Lindernia procumbens Philcox, Rotala indica Koehne, Elatine triandra Schk, Ammannia multiflora Roxb., etc.), Cyperus serotinus Rottboel, and Sagittaria pygmaea Miq were inoculated to paddy field soil filled in a 500cm2 pot and brought to a submerged condition of about 2 - 3 cm. At 1.5 - 2 leafstage of each weed prescribed diluted solution of preparation of each active compound and each herbicide in the following table was applied on water surface each singly or simultaneously. After the treatment, the submerged condition of 3 cm was maintained and the herbicidal effect was studied 3 weeks after the treatment. The herbicidal effect was evaluated as 100% in case of complete death and 0% in case of no effect.
<Results>
Results are shown in Table 1 - Table 3. In the tables, MOOVP represents Monochoria vaginalis Presl, BBBBB represents annual broad-leaves, CYPSE represents Cyperus serotinus Rottboel and SAGPY represents Sagittaria pygmaea
Miq.
Table 1
Amount of effective Herbicidal effect (%) component
Active g/ha MOOVP BBBBB YPSE SAGPY component
(a-1 ) 2.5 40 70 80 60
+(b-1 ) +200 90 100 90 70
+100 70 80 80 70
Single 200 10 0 0 10
100 10 0 0 10
+(b-2) +250 100 100 80 90
+125 70 90 80 80
Single 250 20 10 0 10
125 10 10 0 0
+(b-3) +150 100 100 100 90
+75 90 100 80 70
Single 150 60 50 70 10
75 50 40 0 10
+(b-4) +180 50 70 80 70
+90 40 70 70 60
Single 180 10 0 0 20
90 0 0 0 10
+(b-5) +100 90 90 100 80
+50 80 90 100 80
Single 100 90 90 70 85
50 75 50 70 65
+(b-6) +100 90 100 100 90
+50 90 100 100 80
Single 100 90 90 30 85
50 80 90 20 50 Amount of effective Herbicidal effect (%) component
Active g/ha MOOVP BBBBB YPSE SAGPY component
(a-1) 2.5 40 70 80 60
+(b-7) +5 70 90 100 80
+2.5 40 80 90 80
Single 5 10 10 60 30
2.5 0 10 20 0
+(b-8) +150 100 100 100 90
+75 90 85 100 80
Single 150 60 70 30 30
75 40 40 30 30
+(b-9) +600 100 90 100 80
+300 100 90 80 70
Single 600 80 40 30 10
300 65 30 30 10
+(b-10) +40 80 90 100 80
+20 60 70 70 60
Single 40 20 40 0 10
20 10 40 0 0
+(b-11 ) +250 70 90 100 80
+125 60 80 100 50
Single 250 0 0 70 20
125 0 0 20 10
+(b-12) +5 70 100 100 95
+2.5 50 90 100 80
Single 5 60 60 40 50
2.5 30 50 40 50 Amount of effective Herbicidal effect (%) component
Active g/ha MOOVP BBBBB YPSE SAGPY component
(a-1 ) 2.5 40 70 80 60
+(b-13) +3 85 100 100 90
+1.5 80 85 90 75
Single 3 70 70 0 65
1.5 65 40 0 65
+(b-14) +400 90 80 90 70
+200 70 50 85 70
Single 400 95 30 60 10
200 30 20 40 10
+(b-15) +150 100 90 90 80
+75 100 80 80 80
Single 150 95 65 85 80
75 85 50 80 80
Table 2
Amount of effective Herbicidal effect (%) component
Active g/ha MOOVP BBBBB CYPSE SAGPY component
(a-2) 2.5 30 60 75 60
+(b-1 ) +200 90 100 90 70
+100 60 70 70 60
Single 200 10 0 0 10
100 10 0 0 10
+(b-2) +250 95 95 70 90
+125 80 85 40 70
Single 250 20 10 0 10
125 10 10 0 0
+(b-3) +150 100 100 100 85
+75 90 90 70 80
Single 150 60 50 70 10
75 50 40 0 10
+(b-4) +180 60 70 95 80
+90 50 70 70 80
Single 180 " 10 0 0 20
90 0 0 0 10
+(b-5) +100 85 95 100 80
+50 85 90 95 70
Single 100 90 90 70 85
50 75 50 70 65
+(b-6) +100 95 100 100 85
+50 90 100 70 80
Single 100 90 90 30 85
50 80 90 20 50 Amount of effective Herbicidal effect (%) component
Active g/ha MOOVP BBBBB CYPSE SAGPY component
(a-2) 2.5 30 60 75 60
+(b-7) +5 60 85 100 80
+2.5 40 60 90 80
Single 5 10 10 60 30
2.5 0 10 20 0
+(b-8) +150 100 100 100 85
+75 90 85 95 85
Single 150 60 70 30 30
75 40 40 30 30
+(b-9) +600 100 90 100 70
+300 90 85 70 70
Single 600 80 40 30 10
300 65 30 30 10
+(b-10) +40 70 80 95 80
+20 40 60 70 70
Single 40 20 40 0 10
20 10 40 0 0
+(b-11 ) +250 80 90 100 70
+125 50 60 80 50
Single 250 0 0 70 20
125 0 0 20 10
+(b-12) +5 85 90 100 70
+2.5 50 80 100 70
Single 5 60 60 40 50
2.5 30 50 40 50 Amount of effective Herbicidal effect (%) component
Active g/ha MOOVP BBBBB CYPSE SAGPY component
(a-2) 2.5 30 60 75 60
+(b-13) +3 85 80 100 80
+1.5 80 80 80 75
Single 3 70 70 0 65
1.5 65 40 0 65
+(b-14) +400 90 70 90 80
+200 40 50 90 60
Single 400 95 30 60 10
200 30 20 40 10
+(b-15) +150 90 85 90 80
+75 100 70 80 85
Single 150 95 65 85 80
75 85 50 80 80
Table 3
Amount of effective Herbicidal effect (%) component
Active g/ha MOOVP BBBBB CYPSE SAGPY component
(a-3) 5.0 30 60 50 50
+(b-1 ) +200 70 80 90 70
+100 50 50 70 60
Single 200 10 0 0 10
100 10 0 0 10
+(b-2) +250 70 80 60 70
+125 50 75 40 60
Single 250 20 10 0 10
125 10 10 0 0
+(b-3) +150 90 90 100 70
+75 90 85 60 60
Single 150 60 50 70 10
75 50 40 0 10
+(b-4) +180 50 60 80 70
+90 30 60 60 70
Single 180 10 0 0 20
90 0 0 0 10
+(b-5) +100 80 95 90 90
+50 85 90 80 70
Single 100 90 90 70 85
50 75 50 70 65
+(b-6) +100 100 100 80 100
+50 90 100 70 80
Single 100 90 90 30 85
50 80 90 20 50 Amount of effective Herbicidal effect (%) component
Active g/ha MOOVP BBBBB CYPSE SAGPY component
(a-3) 5.0 30 60 50 50
+(b-7) +5 50 80 100 80
+2.5 30 75 80 70
Single 5 10 10 60 30
2.5 0 10 20 0
+(b-8) +150 90 90 80 80
+75 60 85 80 80
Single 150 60 70 30 30
75 40 40 30 30
+(b-9) +600 90 90 90 70
+300 80 85 80 60
Single 600 80 40 30 10
300 65 30 30 10
+(b-10) +40 70 80 80 70
+20 50 70 70 70
Single 40 20 40 0 10
20 10 40 0 0
+(b-11 ) +250 50 60 90 70
+125 40 60 70 70
Single 250 0 0 70 20
125 0 0 20 10
+(b-12) +5 80 95 90 85
+2.5 40 90 90 70
Single 5 60 60 40 50
2.5 30 50 40 50 Amount of effective Herbicidal effect (%) component
Active g/ha MOOVP BBBBB CYPSE SAGPY component
(a-3) 5.0 30 60 50 50
+(b-13) +3 80 90 70 80
+1.5 80 90 50 80
Single 3 70 70 0 65
+1.5 65 40 0 65
+(b-14) +400 90 80 90 80
+200 60 60 70 70
Single 400 95 30 60 10
200 30 20 40 10
+(b-15) +150 90 100 90 90
+75 90 80 70 85
Single 150 95 65 85 80
75 85 50 80 80
Test example 2: Test of effect of phytotoxicity reduction <Test method>
In a green house, paddy rice of 2 - 2.5 leafstage was transplanted to paddy field soil filled in a 1000cm2 pot to 2cm depth and brought to a submerged condition of about 2 - 3cm. Five days after the transplantation, prescribed diluted solution of preparation of each active compound and each herbicide in the following table was applied on water surface each singly or simultaneously. After the treatment, the submerged condition of 3cm was maintained and the grade of phytotoxicity to paddy rice was studied 2 weeks after the treatment. The phytotoxicity was evaluated as 100% in case of complete death and 0% in case of no phytotoxicity. <Results> Results are shown in Table 4. Table 4
Figure imgf000023_0001
Formulation Example 1
To a mixture of 3 parts by weight of the active compound (a-1 ), 4 parts by weight of the active compound (b-1 ), 32 parts by weight of bentonite (montmorillonite), 58 parts by weight of talc and 3 parts by weight of ligninsulfonate salt, 25 parts by weight of water were added, well kneaded, made into granules of 10-40 mesh by an extrusion granulator and dried at 40-500C to obtain granules.
Formulation Example 2
96 Parts by weight of clay mineral particles having particle diameter distribution in the range of 0.2-2mm are put in a rotary mixer. While rotating it, 2 parts by weight of the active compound (a-1 ) and 2 parts by weight of the active compound (b-2) are sprayed together with a liquid diluent, wetted uniformly and dried at 40-500C to obtain granules.
Formulation Example 3
A mixture of 4 parts by weight of the active compound (a-1 ), 4 parts by weight of the active compound (b-3), 10 parts by weight of ethylene glycol, 3 parts by weight of polyoxyalkylene tristyrylphenyl ether, 10 parts by weight of xanthan gum, 0.5 parts by weight of 14% silicone oil emulsion and 68.5 parts by weight of water is well stirred and then crushed with a crusher (Dyno-Mill Type KDL) to obtain water suspension formulation.
Formulation Example 4
5 Parts by weight of the active compound (a-1), 15 parts by weight of the active compound (b-4), 30 parts by weight of sodium ligninsulfonate, 15 parts by weight of parts bentonite and 35 parts by weight of calcined diatomaceous earth powder are well mixed, added with water, well kneaded, extruded with 0.3mm screen and dried to obtain water dispersible granules. [Industrial applicability]
The herbicide composition for paddy field of the present invention shows, as shown in the aforementioned test examples, precise controlling effect against various kinds of paddy field weeds and an excellent residual effect.

Claims

Patent Claims
1. A herbicide composition for paddy field characterized by comprising a combination of components (a), (b) and/or (c), wherein
(a) is one or more difluoromethanesulfonamide derivatives represented by the formula (I),
Figure imgf000025_0001
wherein
X represents a halogen, Y represents CH or N,
R1 represents hydrogen, and R2 represents hydrogen or hydroxy, or
R1 and R2 together form C=O with the carbon atom to which they are bonding, (b) is one or more herbicidal compounds selected from the group consisting of pretilachlor, butachlor, alachlor, metolachlor, acetochlor, clomeprop, bromobutide, benfuresate, indanofan, pyrazolate, benzofenap, pyrazoxyfen, pyraclonil, oxaziclomefone, bensulfuron-methyl, azimsulfuron, imazosulfuron, pyrazosulfuron-ethyl, cyclosulfamuron, ethoxysulfuron, halosulfuron-methyl, orthosulfamuron, cinosulfuron, metsulfuron-methyl, penoxsulam, thiobencarb, pyributycarb, molinate, dimethametryn, simetryn, cafenstrole, quinclorac, anilofos, mefenacet, fentrazamide, pentoxazone, oxadiargyl, oxadiazon, benzobicyclon, mesotrione, AVH301 , cyhalofop-butyl, metamifop, bispyribac-sodium, pyriftalid, pyrimisulfan, pyrimenobac-methyl, chlormethoxynil, oxyfluorfen, dithiopyr, MCPA, MCPB, 2,4-D, dymron, cumyluron, quinoclamine and clomazone, and (c) is, as a safener, one or more compounds selected from the group consisting of dymron, isoxadifen(-ethyl), flurazole, fenchlorazole-ethyl, fenclorim, cloquintocet-mexyl, oxabetrinil, fluxofenim, mefenpyr-diethyl, furilazole, R-29148, benoxacor, dichlormid and dicyclonone as effective components.
2. A composition according to claim 1 , characterized in that X represents fluorine or chlorine,
Y represents CH or N, R1 represents hydrogen, and R2 represents hydrogen or hydroxy, or
R1 and R2 together form C=O with the carbon atom to which they are bonding, in the formula (I).
3. A composition according to claim 1 or 2, characterized in that it comprises one or more herbicidal compounds (b) in the range of 0.05-200 parts by weight to 1 part by weight of the compound (a).
4. A composition according to any one of claims 1 to 3, characterized in that it comprises one or more compounds (c) as a safener in the range of 0.05-200 parts by weight to 1 part by weight of the compound (a).
5. Method for controlling weeds in a paddy field which comprises applying to the weeds, parts of the weeds, weed seeds or their habitat, optionally in the presence of a crop, a combination of a herbicide (a) and a herbicide (b), or a herbicide (a) and a safener (c), or a herbicide (a), a herbicide (b) and a safener (c), wherein the components (a), (b) and (c) of the specific combination are applied simultaneously or sequentially, and wherein the components are defined as in any one of claims 1 to 4.
6. Method as claimed in claims 5, wherein the crop is rice.
7. Use of a combination of components (a), (b) and/or (c) as defined in any of claims 1 to 4 for controlling weeds in a paddy field, optionally in the presence of a crop.
8. The use as claimed in claim 7, wherein the crop is rice.
PCT/EP2006/012502 2006-01-13 2006-12-22 A herbicide composition for paddy field Ceased WO2007079965A2 (en)

Priority Applications (4)

Application Number Priority Date Filing Date Title
DE602006021802T DE602006021802D1 (en) 2006-01-13 2006-12-22 HERBICIDAL COMPOSITION FOR PADDY FIELDS
AT06841143T ATE507719T1 (en) 2006-01-13 2006-12-22 HERBICIDE COMPOSITION FOR PADDY FIELDS
BRPI0621576-9A BRPI0621576A2 (en) 2006-01-13 2006-12-22 herbicidal composition for paddy field
EP06841143A EP1976384B1 (en) 2006-01-13 2006-12-22 A herbicide composition for paddy field

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
JP2006-6422 2006-01-13
JP2006006422A JP2007186460A (en) 2006-01-13 2006-01-13 Herbicidal composition for rice field

Publications (2)

Publication Number Publication Date
WO2007079965A2 true WO2007079965A2 (en) 2007-07-19
WO2007079965A3 WO2007079965A3 (en) 2008-10-16

Family

ID=38134900

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/EP2006/012502 Ceased WO2007079965A2 (en) 2006-01-13 2006-12-22 A herbicide composition for paddy field

Country Status (10)

Country Link
US (2) US7855165B2 (en)
EP (2) EP1976384B1 (en)
JP (1) JP2007186460A (en)
KR (1) KR20080091358A (en)
CN (1) CN101410014A (en)
AR (1) AR058966A1 (en)
AT (1) ATE507719T1 (en)
BR (1) BRPI0621576A2 (en)
DE (1) DE602006021802D1 (en)
WO (1) WO2007079965A2 (en)

Cited By (28)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2008101595A3 (en) * 2007-02-19 2009-06-18 Bayer Cropscience Ag Herbicidal compositions comprising difluoromethanesulfonylanilide and one or more herbicides
EP2092825A1 (en) * 2008-02-21 2009-08-26 Bayer CropScience Aktiengesellschaft Herbicidal combinations comprising a herbicide of the class of the diamino-s-triazines
WO2009024251A3 (en) * 2007-08-20 2009-11-26 Bayer Cropscience Ag Use of sulfonanilide compounds as herbicide
WO2010017928A1 (en) * 2008-08-14 2010-02-18 Bayer Cropscience Ag Herbicidal combination comprising dimethoxy-triazinyl-substituted difluoromethane sulfonyanilides
DE102008037629A1 (en) 2008-08-14 2010-02-18 Bayer Cropscience Ag Herbicide combination with dimethoxytriazinyl-substituted difluoromethanesulfonylanilides
WO2010017929A1 (en) * 2008-08-14 2010-02-18 Bayer Cropscience Ag Herbicidal combination comprising dimethoxytriazinyl-substituted difluoromethane sulfonylanilides
DE102008037627A1 (en) 2008-08-14 2010-02-18 Bayer Cropscience Ag Herbicide combination with dimethoxytriazinyl-substituted difluoromethanesulfonylanilides
DE102008037632A1 (en) 2008-08-14 2010-02-18 Bayer Cropscience Ag Herbicide combination with dimethoxytriazinyl-substituted difluoromethanesulfonylanilides
DE102008037621A1 (en) 2008-08-14 2010-02-18 Bayer Cropscience Ag Herbicide combination with dimethoxytriazinyl-substituted difluoromethanesulfonylanilides
DE102008037630A1 (en) 2008-08-14 2010-02-18 Bayer Cropscience Ag Herbicidal combination, useful to control undesired plant growth in plant culture e.g. wheat, comprises dimethoxytriazinyl-substituted difluoromethanesulfonyl anilide compounds and herbicides comprising triazine compounds e.g. ametryn
DE102008037624A1 (en) 2008-08-14 2010-02-18 Bayer Cropscience Ag Herbicide combination with dimethoxytriazinyl-substituted difluoromethanesulfonylanilides
DE102008037625A1 (en) 2008-08-14 2010-02-18 Bayer Cropscience Ag Herbicide combination with dimethoxytriazinyl-substituted difluoromethanesulfonylanilides
DE102008037626A1 (en) 2008-08-14 2010-02-18 Bayer Cropscience Ag Herbicide combination with dimethoxytriazinyl-substituted difluoromethanesulfonylanilides
DE102008037628A1 (en) 2008-08-14 2010-02-18 Bayer Crop Science Ag Herbicide combination with dimethoxytriazinyl-substituted difluoromethanesulfonylanilides
DE102008037620A1 (en) 2008-08-14 2010-02-18 Bayer Crop Science Ag Herbicide combination with dimethoxytriazinyl-substituted difluoromethanesulfonylanilides
US8008484B2 (en) 2004-07-23 2011-08-30 Bayer Cropscience Ag Use of sulfonanilides as agricultural and horticultural fungicide
RU2440731C2 (en) * 2010-02-24 2012-01-27 Юрий Аглямович Гарипов Suspension concentrate of herbicidal composition and preparation method thereof
DE102010042786A1 (en) 2010-10-22 2012-04-26 Bayer Cropscience Ag Herbicide combination useful for controlling unwanted plant growth, comprises N-(dimethoxy-triazine-carbonyl)-fluorophenyl-difluoro-N-methylmethanesulfonamide, and (chloro-dioxido-dihydro-benzothien-yl)carbonyl-cyclohexane-dione
WO2012052408A2 (en) 2010-10-22 2012-04-26 Bayer Cropscience Ag Herbicide combination with a dimethoxytriazinyl-substituted difluoromethanesulphonylanilide
CN103098821A (en) * 2013-02-02 2013-05-15 广东中迅农科股份有限公司 Penoxsulam-anilofos weeding composition
CN103120173A (en) * 2013-02-04 2013-05-29 广东中迅农科股份有限公司 Paddy field weeding composition
CN101835376B (en) * 2007-10-26 2013-05-29 组合化学工业株式会社 Agent for improving sugarcane brix and method of promoting sugarcane ripening using the same
CN103271056A (en) * 2013-04-27 2013-09-04 广东中迅农科股份有限公司 Quinclorac-cyclosulfamuron herbicide composition
CN103271071A (en) * 2013-04-27 2013-09-04 广东中迅农科股份有限公司 Penoxsulam-fentrazamide herbicide composition
CN103271055A (en) * 2013-04-27 2013-09-04 广东中迅农科股份有限公司 Synergistic weeding composition for preventing and removing weed in paddy field
CN103271070A (en) * 2013-04-27 2013-09-04 广东中迅农科股份有限公司 Pyrazosulfuron ethyl-fentrazamide herbicide composition
CN106879605A (en) * 2017-02-27 2017-06-23 山东省农业科学院植物保护研究所 A kind of herbicidal composition of Han oxadiazons and S-metolachlor
WO2018104142A1 (en) 2016-12-07 2018-06-14 Bayer Cropscience Aktiengesellschaft Herbicidal combination containing triafamone and indaziflam

Families Citing this family (29)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2009022598A1 (en) * 2007-08-10 2009-02-19 Kumiai Chemical Industry Co., Ltd. Composition for weeding
CN101785457A (en) * 2010-02-25 2010-07-28 深圳诺普信农化股份有限公司 Oil-based suspension for weeding paddy field and preparation method thereof
CN101822258A (en) * 2010-05-18 2010-09-08 东莞市瑞德丰生物科技有限公司 Weeding composition
JP6045500B2 (en) * 2011-10-13 2016-12-14 国立研究開発法人農業・食品産業技術総合研究機構 Gene encoding cytochrome P450 and use thereof
CN102396473B (en) * 2011-12-16 2013-11-27 联保作物科技有限公司 Herbicide composition
RU2641009C2 (en) * 2012-12-12 2018-01-15 ДАУ АГРОСАЙЕНСИЗ ЭлЭлСи Synergic method of weed control with application of penoxulam and mephenacete
KR102230973B1 (en) * 2013-03-15 2021-03-23 다우 아그로사이언시즈 엘엘씨 Synergistic weed control from applications of penoxsulam and benzobicyclon or clomazone and benzobicyclon
CN103130575A (en) * 2013-03-18 2013-06-05 哈尔滨利民农化技术有限公司 Weedicide composition used in rice field
CN103283760B (en) * 2013-06-26 2014-12-10 联保作物科技有限公司 Rice field weeding composite and preparation thereof
CN103392713B (en) * 2013-06-30 2016-05-11 广东中迅农科股份有限公司 The Herbicidal combinations that contains penoxsuam and KIH 6127
CN103688972B (en) * 2013-11-28 2016-08-17 广东中迅农科股份有限公司 A kind of containing cyhalofop-butyl with the Herbicidal combinations of cafenstrole
CN103975938B (en) * 2014-04-08 2016-12-07 广东中迅农科股份有限公司 A kind of Herbicidal combinations for preventing and kill off rice terrace annual grassy weeds
CN104012566B (en) * 2014-06-24 2015-01-14 济南科赛基农化工有限公司 Synergism weeding composition for paddy field
CN104273153A (en) * 2014-09-26 2015-01-14 青岛康和食品有限公司 Paddy field molinate type herbicide composition
CN104430442A (en) * 2014-10-29 2015-03-25 山东华亚环保科技有限公司 Safe herbicide for rice
CN104365641B (en) * 2014-10-30 2017-07-28 广东中迅农科股份有限公司 A kind of Herbicidal combinations containing orthosulfamuron and KIH 6127
JP2016141628A (en) * 2015-01-30 2016-08-08 協友アグリ株式会社 Herbicide composition
JP6584079B2 (en) * 2015-01-30 2019-10-02 協友アグリ株式会社 Herbicidal composition
JP2016141627A (en) * 2015-01-30 2016-08-08 協友アグリ株式会社 Herbicide composition
JP2016141629A (en) * 2015-01-30 2016-08-08 協友アグリ株式会社 Herbicide composition
CN104872147B (en) * 2015-06-24 2017-01-11 陕西上格之路生物科学有限公司 Weeding composition containing pentoxazone and mefenacet
CN104982443B (en) * 2015-06-25 2018-03-23 陕西上格之路生物科学有限公司 A kind of Herbicidal combinations of Han oxaziclomefones and mefenacet
CN105028430A (en) * 2015-08-05 2015-11-11 海利尔药业集团股份有限公司 Weeding composition containing oxaziclomefone and topramezone
US10609928B2 (en) * 2015-08-07 2020-04-07 Bayer Cropscience Aktiengesellschaft Uses of 2-(2,4-dichlorophenyl)methyl-4,4-dimethyl-3-isoxazolidone as foliar herbicide
CN105901005A (en) * 2016-05-16 2016-08-31 河北博嘉农业有限公司 Weeding composition containing pyraclonil
CN106561695A (en) * 2016-11-15 2017-04-19 江苏龙灯化学有限公司 Weeding composition
CN111165501A (en) * 2019-12-27 2020-05-19 安徽众邦生物工程有限公司 Weeding composition containing triafamone and mefenacet
CN111635275B (en) * 2020-06-02 2022-06-28 武汉天度植物科技有限公司 Pesticide fertilizer for preventing and treating weeds in paddy fields and preparation and application thereof
CN118120532A (en) * 2022-12-01 2024-06-04 浙江省合力农业与生命科学研究院 Method for preventing and killing weeds in direct seeding paddy field

Family Cites Families (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3989503A (en) 1972-10-13 1976-11-02 Stauffer Chemical Company Herbicidal antidote compositions with substituted oxazolidines and thiazolidines
JP4231585B2 (en) * 1999-03-26 2009-03-04 クミアイ化学工業株式会社 Mixed herbicidal composition
AU2003221022A1 (en) * 2002-03-27 2003-10-08 Kumiai Chemical Industry Co., Ltd. Herbicidal composition and method of weeding with the same
PY0318279A (en) * 2002-07-25 2008-12-01 Kumiai Chemical Industry Co HERBICIDE COMPOSITION AND METHOD FOR WEED CONTROL USED BY IT
JP2004292417A (en) * 2003-03-26 2004-10-21 Sds Biotech:Kk Methods for reducing phytotoxicity and weeding
JP2006056870A (en) * 2004-04-01 2006-03-02 Bayer Cropscience Ag Difluoromethanesulfonamide derivative and herbicide
JP2005306813A (en) * 2004-04-23 2005-11-04 Bayer Cropscience Kk Mixed herbicidal composition

Cited By (73)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US8008484B2 (en) 2004-07-23 2011-08-30 Bayer Cropscience Ag Use of sulfonanilides as agricultural and horticultural fungicide
WO2008101595A3 (en) * 2007-02-19 2009-06-18 Bayer Cropscience Ag Herbicidal compositions comprising difluoromethanesulfonylanilide and one or more herbicides
WO2009024251A3 (en) * 2007-08-20 2009-11-26 Bayer Cropscience Ag Use of sulfonanilide compounds as herbicide
CN101848641A (en) * 2007-08-20 2010-09-29 拜尔农作物科学股份公司 Use of sulfonanilide compounds as herbicides
CN101835376B (en) * 2007-10-26 2013-05-29 组合化学工业株式会社 Agent for improving sugarcane brix and method of promoting sugarcane ripening using the same
EP2092825A1 (en) * 2008-02-21 2009-08-26 Bayer CropScience Aktiengesellschaft Herbicidal combinations comprising a herbicide of the class of the diamino-s-triazines
CN102186344A (en) * 2008-08-14 2011-09-14 拜尔农作物科学股份公司 Herbicidal combination comprising dimethoxy-triazinyl-substituted difluoromethane sulfonylanilides
WO2010017925A3 (en) * 2008-08-14 2010-10-21 Bayer Cropscience Ag Herbicidal-safener-combination comprising dimethoxytriazinyl- substituted difluormethane sulfonylanilides
DE102008037629A1 (en) 2008-08-14 2010-02-18 Bayer Cropscience Ag Herbicide combination with dimethoxytriazinyl-substituted difluoromethanesulfonylanilides
WO2010017929A1 (en) * 2008-08-14 2010-02-18 Bayer Cropscience Ag Herbicidal combination comprising dimethoxytriazinyl-substituted difluoromethane sulfonylanilides
DE102008037627A1 (en) 2008-08-14 2010-02-18 Bayer Cropscience Ag Herbicide combination with dimethoxytriazinyl-substituted difluoromethanesulfonylanilides
DE102008037632A1 (en) 2008-08-14 2010-02-18 Bayer Cropscience Ag Herbicide combination with dimethoxytriazinyl-substituted difluoromethanesulfonylanilides
DE102008037621A1 (en) 2008-08-14 2010-02-18 Bayer Cropscience Ag Herbicide combination with dimethoxytriazinyl-substituted difluoromethanesulfonylanilides
DE102008037630A1 (en) 2008-08-14 2010-02-18 Bayer Cropscience Ag Herbicidal combination, useful to control undesired plant growth in plant culture e.g. wheat, comprises dimethoxytriazinyl-substituted difluoromethanesulfonyl anilide compounds and herbicides comprising triazine compounds e.g. ametryn
DE102008037624A1 (en) 2008-08-14 2010-02-18 Bayer Cropscience Ag Herbicide combination with dimethoxytriazinyl-substituted difluoromethanesulfonylanilides
DE102008037625A1 (en) 2008-08-14 2010-02-18 Bayer Cropscience Ag Herbicide combination with dimethoxytriazinyl-substituted difluoromethanesulfonylanilides
DE102008037626A1 (en) 2008-08-14 2010-02-18 Bayer Cropscience Ag Herbicide combination with dimethoxytriazinyl-substituted difluoromethanesulfonylanilides
DE102008037628A1 (en) 2008-08-14 2010-02-18 Bayer Crop Science Ag Herbicide combination with dimethoxytriazinyl-substituted difluoromethanesulfonylanilides
DE102008037620A1 (en) 2008-08-14 2010-02-18 Bayer Crop Science Ag Herbicide combination with dimethoxytriazinyl-substituted difluoromethanesulfonylanilides
DE102008037622A1 (en) 2008-08-14 2010-02-25 Bayer Cropscience Ag Herbicide combination with dimethoxytriazinyl-substituted difluoromethanesulfonylanilides
WO2010017930A3 (en) * 2008-08-14 2010-10-14 Bayer Cropscience Ag Herbicidal combination comprising dimethoxy-triazinyl-substituted difluoromethane sulfonylanilides
WO2010017924A3 (en) * 2008-08-14 2010-10-14 Bayer Cropscience Ag Herbicidal combination comprising dimethoxytriazinyl-substituted difluoromethane sulfonylanilides
WO2010017927A3 (en) * 2008-08-14 2010-10-21 Bayer Cropscience Ag Herbicidal combination comrpising dimethoxytriazinyl-substituted difluoromethane sulfonylanilides
CN102264229B (en) * 2008-08-14 2013-10-30 拜尔农作物科学股份公司 Herbicide combinations comprising difluoromethanesulfonylanilides substituted by dimethoxytriazinyl
WO2010017922A3 (en) * 2008-08-14 2010-10-21 Bayer Cropscience Ag Herbicidal combination comprising dimethoxy-triazinyl-substituted difluoromethane sulfonylanilides
WO2010017923A3 (en) * 2008-08-14 2010-11-04 Bayer Cropscience Ag Herbicidal combination with dimethoxy-triazinyl-substituted difluoromethane sulfonylanilides
WO2010017921A3 (en) * 2008-08-14 2010-11-11 Bayer Cropscience Ag Herbicidal combination comprising dimethoxy-triazinyl-substituted difluoromethane sulfonylanilides
WO2010017931A3 (en) * 2008-08-14 2010-11-11 Bayer Cropscience Ag Herbicidal combination comprising dimethoxy-triazinyl-substituted difluoromethane sulfonylanilides
WO2010017926A3 (en) * 2008-08-14 2011-04-21 Bayer Cropscience Ag Herbicidal combination comprising dimethoxy-triazinyl-substituted difluoromethane sulfonylanilides
KR20110042228A (en) * 2008-08-14 2011-04-25 바이엘 크롭사이언스 아게 Herbicide formulations comprising dimethoxytriazinyl-substituted difluoromethanesulfonylanilide
KR20110042229A (en) * 2008-08-14 2011-04-25 바이엘 크롭사이언스 아게 Herbicide formulations comprising dimethoxytriazinyl-substituted difluoromethanesulfonylanilide
KR20110042223A (en) * 2008-08-14 2011-04-25 바이엘 크롭사이언스 아게 Herbicide formulations comprising dimethoxytriazinyl-substituted difluoromethanesulfonylanilide
KR20110042227A (en) * 2008-08-14 2011-04-25 바이엘 크롭사이언스 아게 Herbicide formulations comprising dimethoxytriazinyl-substituted difluoromethanesulfonylanilide
KR20110049869A (en) * 2008-08-14 2011-05-12 바이엘 크롭사이언스 아게 Herbicide formulations comprising dimethoxytriazinyl-substituted difluoromethanesulfonylanilide
KR20110053241A (en) * 2008-08-14 2011-05-19 바이엘 크롭사이언스 아게 Herbicide formulations comprising dimethoxytriazinyl-substituted difluoromethanesulfonylanilide
CN102186349A (en) * 2008-08-14 2011-09-14 拜尔农作物科学股份公司 Herbicidal conjugates containing difluoromethanesulfonanilides substituted by dimethoxytriazinyl
WO2010017928A1 (en) * 2008-08-14 2010-02-18 Bayer Cropscience Ag Herbicidal combination comprising dimethoxy-triazinyl-substituted difluoromethane sulfonyanilides
CN102186343A (en) * 2008-08-14 2011-09-14 拜尔农作物科学股份公司 Herbicidal conjugates comprising difluoromethanesulfonylanilides substituted by dimethoxytriazinyl
DE102008037631A1 (en) 2008-08-14 2010-02-18 Bayer Cropscience Ag Herbicide combination with dimethoxytriazinyl-substituted difluoromethanesulfonylanilides
CN105010385B (en) * 2008-08-14 2018-06-19 拜耳知识产权有限责任公司 The Herbicidal combination of difluoro methylsulfonylphenylamine comprising the substitution of dimethoxy-triazine base
CN102264229A (en) * 2008-08-14 2011-11-30 拜尔农作物科学股份公司 Herbicide combinations comprising difluoromethanesulfonylanilides substituted by dimethoxytriazinyl
KR101663021B1 (en) * 2008-08-14 2016-10-14 바이엘 인텔렉쳐 프로퍼티 게엠베하 Herbicidal combination comprising dimethoxytriazinyl-substituted difluoromethanesulfonylanilides
KR101663097B1 (en) * 2008-08-14 2016-10-14 바이엘 인텔렉쳐 프로퍼티 게엠베하 Herbicidal combination comprising dimethoxytriazinyl-substituted difluoromethane sulfonylanilides
KR101663095B1 (en) * 2008-08-14 2016-10-14 바이엘 인텔렉쳐 프로퍼티 게엠베하 Herbicidal combination comprising dimethoxytriazinyl-substituted difluoromethanesulfonylanilides
KR101663022B1 (en) * 2008-08-14 2016-10-14 바이엘 인텔렉쳐 프로퍼티 게엠베하 Herbicidal combination comprising dimethoxytriazinyl-substituted difluoromethanesulfonylanilides
KR101663102B1 (en) * 2008-08-14 2016-10-14 바이엘 인텔렉쳐 프로퍼티 게엠베하 Herbicidal combination comprising dimethoxytriazinyl-substituted difluoromethanesulfonylanilides
KR101663024B1 (en) * 2008-08-14 2016-10-14 바이엘 인텔렉쳐 프로퍼티 게엠베하 Herbicidal combination comprising dimethoxytriazinyl-substituted difluoromethanesulfonylanilides
CN102186346B (en) * 2008-08-14 2016-09-21 拜耳知识产权有限责任公司 Comprise the weeding conjugate of the difluoro methylsulfonylphenylamine replaced by dimethoxy-triazine base
CN102186349B (en) * 2008-08-14 2014-05-28 拜尔农作物科学股份公司 Herbicidal conjugates containing difluoromethanesulfonanilides substituted by dimethoxytriazinyl
CN103999864A (en) * 2008-08-14 2014-08-27 拜尔农作物科学股份公司 Herbicide combination comprising dimethoxytriazinyl-substituted difluoromethanesulfonylanilides
CN102186344B (en) * 2008-08-14 2015-04-01 拜尔农作物科学股份公司 Herbicidal combination comprising dimethoxy-triazinyl-substituted difluoromethane sulfonylanilides
CN102186345B (en) * 2008-08-14 2015-06-10 拜尔农作物科学股份公司 Herbicidal conjugates containing difluoromethanesulfonanilides substituted by dimethoxytriazinyl
CN103999864B (en) * 2008-08-14 2016-04-27 拜尔农作物科学股份公司 Weeding bond containing the difluoro methylsulfonylphenylamine replaced by dimethoxy-triazine base
CN102202508B (en) * 2008-08-14 2016-03-02 拜耳知识产权有限责任公司 Herbicide conjugates comprising dimethoxytriazinyl-substituted difluoromethanesulfonanilides
CN102186348B (en) * 2008-08-14 2016-02-24 拜耳知识产权有限责任公司 Herbicide combinations comprising difluoromethanesulfonylanilides substituted by dimethoxytriazinyl
CN105010385A (en) * 2008-08-14 2015-11-04 拜耳知识产权有限责任公司 Herbicidal combination comprising dimethoxytriazinyl-substituted difluoromethane sulfonylanilides
CN104872144A (en) * 2008-08-14 2015-09-02 拜尔农作物科学股份公司 Herbicidal combination comprising dimethoxytriazinyl-substituted difluoromethane sulfonylanilides
RU2440731C2 (en) * 2010-02-24 2012-01-27 Юрий Аглямович Гарипов Suspension concentrate of herbicidal composition and preparation method thereof
DE102010042786A1 (en) 2010-10-22 2012-04-26 Bayer Cropscience Ag Herbicide combination useful for controlling unwanted plant growth, comprises N-(dimethoxy-triazine-carbonyl)-fluorophenyl-difluoro-N-methylmethanesulfonamide, and (chloro-dioxido-dihydro-benzothien-yl)carbonyl-cyclohexane-dione
WO2012052408A2 (en) 2010-10-22 2012-04-26 Bayer Cropscience Ag Herbicide combination with a dimethoxytriazinyl-substituted difluoromethanesulphonylanilide
CN103098821A (en) * 2013-02-02 2013-05-15 广东中迅农科股份有限公司 Penoxsulam-anilofos weeding composition
CN103120173B (en) * 2013-02-04 2015-08-05 广东中迅农科股份有限公司 Herbicidal composition for rice field
CN103120173A (en) * 2013-02-04 2013-05-29 广东中迅农科股份有限公司 Paddy field weeding composition
CN103271071B (en) * 2013-04-27 2015-08-05 广东中迅农科股份有限公司 Penoxsuam and fentrazamide Herbicidal combinations
CN103271055A (en) * 2013-04-27 2013-09-04 广东中迅农科股份有限公司 Synergistic weeding composition for preventing and removing weed in paddy field
CN103271056A (en) * 2013-04-27 2013-09-04 广东中迅农科股份有限公司 Quinclorac-cyclosulfamuron herbicide composition
CN103271071A (en) * 2013-04-27 2013-09-04 广东中迅农科股份有限公司 Penoxsulam-fentrazamide herbicide composition
CN103271070A (en) * 2013-04-27 2013-09-04 广东中迅农科股份有限公司 Pyrazosulfuron ethyl-fentrazamide herbicide composition
CN103271055B (en) * 2013-04-27 2015-08-05 广东中迅农科股份有限公司 A kind of Synergistic herbicide compositions for preventing and kill off paddy field weed
CN103271070B (en) * 2013-04-27 2015-08-05 广东中迅农科股份有限公司 Pyrazosulfuron and fentrazamide Herbicidal combinations
CN103271056B (en) * 2013-04-27 2015-09-16 广东中迅农科股份有限公司 Dichloro quinolinic acid and cyclosulfamuron herbicidal composition
WO2018104142A1 (en) 2016-12-07 2018-06-14 Bayer Cropscience Aktiengesellschaft Herbicidal combination containing triafamone and indaziflam
CN106879605A (en) * 2017-02-27 2017-06-23 山东省农业科学院植物保护研究所 A kind of herbicidal composition of Han oxadiazons and S-metolachlor

Also Published As

Publication number Publication date
EP1976384B1 (en) 2011-05-04
KR20080091358A (en) 2008-10-10
WO2007079965A3 (en) 2008-10-16
EP1976384A2 (en) 2008-10-08
US7855165B2 (en) 2010-12-21
AR058966A1 (en) 2008-03-05
CN101410014A (en) 2009-04-15
EP2298075A1 (en) 2011-03-23
JP2007186460A (en) 2007-07-26
US20110059847A1 (en) 2011-03-10
BRPI0621576A2 (en) 2011-12-13
DE602006021802D1 (en) 2011-06-16
US20070167328A1 (en) 2007-07-19
ATE507719T1 (en) 2011-05-15

Similar Documents

Publication Publication Date Title
US7855165B2 (en) Herbicide composition for paddy field
JP5702933B2 (en) Mixed herbicide composition
JP4847952B2 (en) Difluoromethanesulfonylanilide derivatives useful as herbicides
KR100563144B1 (en) Selective Herbicide Composition
JP4708349B2 (en) Herbicide composition for paddy field
JP4926459B2 (en) How to reduce chemical damage
JPH09241109A (en) Herbicide composition
JP2000239111A (en) Mixed herbicide composition for rice paddy
JPH10218708A (en) Herbicidal composition for paddy field
JPH10231226A (en) Herbicidal composition

Legal Events

Date Code Title Description
121 Ep: the epo has been informed by wipo that ep was designated in this application
WWE Wipo information: entry into national phase

Ref document number: 2006841143

Country of ref document: EP

WWE Wipo information: entry into national phase

Ref document number: 12008501543

Country of ref document: PH

WWE Wipo information: entry into national phase

Ref document number: 3535/CHENP/2008

Country of ref document: IN

WWE Wipo information: entry into national phase

Ref document number: 08071233

Country of ref document: CO

WWE Wipo information: entry into national phase

Ref document number: 200680050936.9

Country of ref document: CN

WWE Wipo information: entry into national phase

Ref document number: 12008501657

Country of ref document: PH

NENP Non-entry into the national phase

Ref country code: DE

WWE Wipo information: entry into national phase

Ref document number: 1020087018782

Country of ref document: KR

ENP Entry into the national phase

Ref document number: PI0621576

Country of ref document: BR

Kind code of ref document: A2

Effective date: 20080714