WO2013176282A1 - Herbicidal composition - Google Patents

Herbicidal composition Download PDF

Info

Publication number
WO2013176282A1
WO2013176282A1 PCT/JP2013/064559 JP2013064559W WO2013176282A1 WO 2013176282 A1 WO2013176282 A1 WO 2013176282A1 JP 2013064559 W JP2013064559 W JP 2013064559W WO 2013176282 A1 WO2013176282 A1 WO 2013176282A1
Authority
WO
WIPO (PCT)
Prior art keywords
compound
formula
methyl
group
salt
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/JP2013/064559
Other languages
French (fr)
Inventor
Taketo Suganuma
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.)
Ishihara Sangyo Kaisha Ltd
Original Assignee
Ishihara Sangyo Kaisha Ltd
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 Ishihara Sangyo Kaisha Ltd filed Critical Ishihara Sangyo Kaisha Ltd
Priority to KR20147035402A priority Critical patent/KR20150020573A/en
Publication of WO2013176282A1 publication Critical patent/WO2013176282A1/en
Anticipated expiration legal-status Critical
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
    • A01N43/02—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms
    • A01N43/24—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms with two or more hetero atoms
    • A01N43/26—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms with two or more hetero atoms five-membered rings
    • A01N43/28—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms with two or more hetero atoms five-membered rings with two hetero atoms in positions 1,3
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N35/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having two bonds to hetero atoms with at the most one bond to halogen, e.g. aldehyde radical
    • A01N35/06—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having two bonds to hetero atoms with at the most one bond to halogen, e.g. aldehyde radical containing keto or thioketo groups as part of a ring, e.g. cyclohexanone, quinone; Derivatives thereof, e.g. ketals
    • 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
    • A01N41/10—Sulfones; Sulfoxides

Definitions

  • the present invention relates to a herbicidal composition
  • a herbicidal composition comprising a compound represented by the formula (I) given hereinafter and another herbicidal compound.
  • Patent Document 1 discloses a certain triketone compound, and it is disclosed that the compound can be used as mixed or combined with other agricultural chemicals, fertilizers, phytotoxicity-reducing agents, etc.
  • Patent Document 1 JP-A-2006-16389
  • the present invention relates to a herbicidal composition
  • a herbicidal composition comprising (A) a
  • X is a 5- or 6-membered saturated heterocyclic group containing one or two hetero atoms of at least one type selected from the group consisting of an oxygen atom and a sulfur atom (said heterocyclic group may be substituted by alkyl), or
  • R 1 is halogen
  • R 2 is alkyl, haloalkyl, alkoxy, haloalkoxy, alkylthio, haloalkylthio, alkylsulfinyl, haloalkylsulfinyl, alkylsulfonyl, haloalkylsulfonyl,
  • the present invention relates to a method for controlling weeds or inhibiting their growth, which comprises applying a herbicidally effective amount of the above herbicidal composition to weeds or to a place where they grow. Further, the present invention relates to a method for controlling weeds or inhibiting their growth, which comprises applying a herbicidally effective amount of the compound A and a herbicidally effective amount of the compound B to weeds or to a place where they grow.
  • composition having a broad herbicidal spectrum, having high activity and having a long- lasting effect.
  • the compound of the above formula (I) or its salt is a known compound disclosed in JP-A-2006-16389.
  • the 5- or 6-membered saturated heterocyclic group containing one or more hetero atoms of at least one type selected from the group consisting of an oxygen atom and a sulfur atom, for X may, for example, be tetrahydrofuran-2-yl, tetrahydrofuran-3-yl, dioxolan-2-yl, dioxolan-4-yl, tetrahydropyran-2-yl, 1 ,4-dioxan-2-yl, 1 ,3-dioxan-2-yl, 1 ,3-dioxan-4-yl, tetrahydrothiofen-2-yl, tetrahydrothiopyran-2-yl, 1 ,3- dithian-2-yl, 1 ,4-dithian-2-yl, 1 ,4-thioxan-2-yl or 1 ,4-thioxan-3-yl.
  • the alkyl or alkyl moiety for X or R 2 may be a C1.6 linear or branched one, such as methyl, ethyl, propyl, isopropyl, butyl, tert-butyl, pentyl or hexyl.
  • the halogen or halogen as a substituent for R 1 or R 2 may be an atom of fluorine, chlorine, bromine or iodine.
  • the number of halogen atoms as substituents may be 1 , or 2 or more, and in the case of 2 or more, the respective halogen atoms may be the same or different. Further, the substitution position of halogen may be any position.
  • the salt of the compound of the formula (I) may be any salt so long as it is agriculturally acceptable, and it may, for example, be an alkali metal salt such as a sodium salt, a potassium salt or a lithium salt; an alkaline earth metal salt such as a magnesium salt, a calcium salt or a barium salt; or an ammonium salt such as a NH 4+ salt, a dimethylamine salt or a triethylamine salt.
  • an alkali metal salt such as a sodium salt, a potassium salt or a lithium salt
  • an alkaline earth metal salt such as a magnesium salt, a calcium salt or a barium salt
  • an ammonium salt such as a NH 4+ salt, a dimethylamine salt or a triethylamine salt.
  • the compound B is represented by a common name or a chemical structural formula.
  • phenoxy acetic acid type compounds are phenoxy acetic acid type compounds.
  • Such phenoxy acetic acid type compounds and (B59) quinclorac are classified into a plant hormone active (auxin active) disturbing herbicide.
  • Specific examples of the above (B1) include 2,4-D, 2,4-D sodium, 2,4-D dimethylammonium, 2,4-D diethylammonium, 2,4-D diethanolammonium, 2,4-D lithium, 2,4-D ethyl, 2,4-D isopropyl, 2,4-D butyl, 2,4-D isooctyl, etc.
  • Specific examples of the above (B2) include MCP (or MCPA), MCP sodium, MCP potassium, MCP calcium, MCP lithium, MCP dimethylammonium, MCP benzyl triethanol ammonium, MCP ethyl, MCP butyl, MCP isooctyl, MCP allyl, etc.
  • (B5) simetryn and (B6) dimethametryn are triazine type compounds.
  • (B7) bentazone is a pyrimidine type compound.
  • Such triazine type compounds and pyrimidine type compound are classified into a photosynthesis-inhibiting herbicide.
  • heterocyclic compounds (B8) oxadiazon, (B9) oxadiargyl, (B10) pentoxazone, (B11) pyraclonil and (B12) carfentrazone-ethyl are heterocyclic compounds.
  • Such heterocyclic compounds are classified into a protoporphyrinogen oxidase-inhibiting herbicide.
  • (B13) pyrazolynate, (B14) pyrazoxyfen and (B15) benzofenap are pyrazole type compounds.
  • (B16) benzobicyclon, (B17) mesotrione, (B18) tefuryltrione, (B19) a compound of the formula (II) and (B63) a compound of the formula (IV) are triketone- type compounds.
  • Such pyrazole type compounds and triketone-type compounds as well as (B20) a compound of the above formula (III) and (B61) clomazone are classified into a 4-hydroxyphenyl pyruvic acid-inhibiting herbicide.
  • cyhalofop-butyl and (B22) metamifop are aryloxyphenoxy propionic acid- type compounds.
  • Such aryloxyphenoxy propionic acid-type compounds are classified into an acetyl CoA carboxylase-inhibiting herbicide.
  • penoxsulam is a sulfone amide-type compound.
  • (B34) pyriminobac-methyl and (B35) bispyribac-sodium are pyrimidinylsalicylic acid-type compounds.
  • (B36) pyrimisulfan and (B37) triafamone are sulfone anilide-type compounds.
  • Such sulfonylurea-type compounds, sulfoneamide-type compounds, pyrimidinylsalicylic acid-type compounds and sulfone anilide-type compounds, as well as (B38) pyriftalid are classified into an acetolactate synthetase-inhibiting herbicide.
  • butamifos is an organic phosphorus compound.
  • daimuron, (B41 ) cumyluron and (B42) bromobutide are cumylamine-type compounds.
  • bromobutide are cumylamine-type compounds.
  • pendimethalin is a dinitroaniline-type compound.
  • Such organic phosphorus compound, cumylamine-type compounds and dinitroaniline-type compound are classified into a cell mitoses-inhibiting herbicide.
  • (B58) quinoclamine is a naphthoquinone type compound.
  • the mixing ratio of compound A and compound B cannot generally be defined, as it is required to be suitably adjusted depending upon the type of the formulation, the weather conditions, and the type and the growth stage of weeds to be controlled.
  • compound B is, for example, from 0.0005 to 500 parts by weight, preferably from 0.002 to 100 parts by weight, more preferably from 0.005 to 100 parts by weight, to 1 part by weight of compound A.
  • compound B is, for example, from 0.0005 to 500 parts by weight, preferably from 0.002 to 100 parts by weight, more preferably from 0.005 to 100 parts by weight, to 1 part by weight of compound A.
  • the mixing ratio of compound A and compound B will be exemplified for the above-mentioned every type of compound B.
  • the weight ratio of each type of compound B to 1 part by weigh of compound A is as follows.
  • such a mixing ratio cannot generally be defined, as it is required to be suitably adjusted depending upon various conditions, and it is also possible to select a mixing ratio outside of such a range.
  • the present invention is by no means restricted by such descriptions.
  • compound B is a phenoxy acetic acid type compound
  • its ratio is from 0.01 to 100 parts by weight, preferably from 0.1 to 11 parts by weight, further preferably from 0.2 to 10 parts by weight.
  • compound B is (B59) quinclorac
  • its ratio is from 0.01 to 100 parts by weight, preferably from 0.1 to 10 parts by weight, further preferably from 0.2 to 10 parts by weight.
  • compound B is a triazine type compound
  • its ratio is from 0.002 to
  • 100 parts by weight preferably from 0.02 to 10 parts by weight, further preferably from 0.05 to 10 parts by weight.
  • compound B is a pyrimidine type compound
  • its ratio is from 0.2 to 500 parts by weight, preferably from 1.6 to 80 parts by weight, further preferably from 4 to 70 parts by weight.
  • compound B is a heterocyclic compound
  • its ratio is from 0.002 to 100 parts by weight, preferably from 0.02 to 16 parts by weight, further preferably from 0.05 to 15 parts by weight.
  • compound B is a pyrazole type compound
  • its ratio is from 0.02 to 500 parts by weight, preferably from 0.4 to 70 parts by weight, further preferably from 1 to 60 parts by weight.
  • compound B is a triketone type compound
  • its ratio is from 0.01 to 50 parts by weight, preferably from 0.04 to 7 parts by weight, further preferably from 0.1 to 7 parts by weight.
  • compound B is (B20) a compound of the above formula (III)
  • its ratio is from 0.005 to 300 parts by weight, preferably from 0.02 to 30 parts by weight, further preferably from 0.05 to 25 parts by weight.
  • compound B is (B61) clomazone
  • its ratio is from 0.01 to 100 parts by weight, preferably from 0.1 to 16 parts by weight, further preferably from 0.2 to 15 parts by weight.
  • compound B is an aryloxyphenoxypropionic acid type compound
  • its ratio is from 0.01 to 50 parts by weight, preferably from 0.04 to 7 parts by weight, further preferably from 0.1 to 6 parts by weight.
  • compound B is a sulfonylurea compound
  • its ratio is from 0.0005 to 30 parts by weight, preferably from 0.002 to 3 parts by weight, further preferably from 0.005 to 2.5 parts by weight.
  • compound B is a sulfonamide type compound
  • its ratio is from 0.002 to 20 parts by weight, preferably from 0.01 to 2 parts by weight, further preferably from 0.02 to 2 parts by weight.
  • compound B is a pyrimidinylsalicylic acid type compound
  • its ratio is from 0.001 to 30 parts by weight, preferably from 0.004 to 3 parts by weight, further preferably from 0.01 to 2.5 parts by weight.
  • compound B is (B38) pyriftalid
  • its ratio is from 0.002 to 50 parts by weight, preferably from 0.02 to 6 parts by weight, further preferably from 0.1 to 5 parts by weight.
  • compound B is an organic phosphorus-type compound
  • its ratio is from 0.2 to 300 parts by weight, preferably from 0.8 to 50 parts by weight, further preferably from 2 to 40 parts by weight.
  • compound B is a cumylamine type compound
  • its ratio is from 0.02 to 300 parts by weight, preferably from 0.4 to 40 parts by weight, further preferably from 1 to 30 parts by weight.
  • compound B is a dinitroaniline type compound
  • its ratio is from 0.1 to 150 parts by weight, preferably from 0.4 to 24 parts by weight, further preferably from 0.2 to 24 parts by weight.
  • 0.02 to 500 parts by weight preferably from 0.2 to 100 parts by weight, further preferably from 0.5 to 100 parts by weight.
  • compound B is a chloroacetamide type compound
  • its ratio is from 0.02 to 300 parts by weight, preferably from 0.1 to 40 parts by weight, further preferably from 0.3 to 35 parts by weight.
  • compound B is (B49) mefenacet, (B50) cafenstrole, (B51) indanofan, (B52) fentrazamide, (B53) oxaziclomefone, (B54) etobenzanid, (B55) benfuresate, (B56) ipfencarbazone or (B57) fenoxasulfone, its ratio is from 0.002 to 300 parts by weight, preferably from 0.01 to 40 parts by weight, further preferably from 0.02 to 30 parts by weight.
  • compound B is (B58) quinoclamine
  • its ratio is from 0.2 to 500 parts by weight, preferably from 1.2 to 60 parts by weight, further preferably from 3 to 50 parts by weight.
  • compound A and compound B cannot generally be defined, as they are required to be suitably adjusted depending upon e.g. the mixing ratio of compound A and compound B, the type of the formulation, the weather conditions, and the type and growth stage of weeds to be controlled.
  • compound A can be suitably selected within a range of from 0.1 to 10 g, preferably from 0.5 to 5 g
  • compound B can be suitably selected within a range of from 0.005 to 50 g, preferably from 0.01 to 50 g, and they may be suitably combined.
  • the amount of application of compound B per 1 are will be exemplified for the above-mentioned every type of compound B.
  • the amount of application cannot generally be defined, as it is required to be suitably adjusted depending upon various conditions, and it is also possible to select the amount of application outside of such a range. Further, it should be understood that the present invention is by no means limited by such descriptions.
  • compound B is a phenoxy acetic acid type compound, it is from 0.1 to 10 g, preferably from 0.5 to 5.5 g.
  • compound B is (B59) quinclorac, it is from 0.1 to 10 g, preferably from 0.5 to 5 g.
  • compound B is a triazine type compound, it is from 0.02 to 10 g, preferably from 0.1 to 5 g.
  • compound B is a pyrimidine type compound, it is from 2 to 50 g, preferably from 8 to 40 g.
  • compound B is a heterocyclic compound, it is from 0.02 to 10 g, preferably from 0.1 to 8 g.
  • compound B is a pyrazole type compound, it is from 0.2 to 50 g, preferably from 2 to 35 g.
  • compound B is a triketone type compound, it is from 0.1 to 5 g, preferably from 0.2 to 3.5 g.
  • compound B is (B20) a compound of the above formula (III), it is from 0.05 to 30 g, preferably from 0.1 to 15 g.
  • compound B is (B61) clomazone, it is from 0.1 to 10 g, preferably from 0.5 to 8 g.
  • compound B is an aryloxyphenoxypropionic acid type compound, it is from 0.1 to 5 g, preferably from 0.2 to 3.5 g.
  • compound B is a sulfonylurea compound, it is from 0.005 to 3 g, preferably from 0.01 to 1.5 g.
  • compound B is a sulfonamide type compound, it is from 0.02 to 2 g, preferably from 0.05 to 1 g.
  • compound B is a pyrimidinylsalicylic acid type compound, it is from 0.01 to 3 g, preferably from 0.02 to 1.5 g.
  • compound B is a sulfonamide type compound, it is from 0.02 to 1.5 g, preferably from 0.1 to 0.8 g.
  • compound B is (B38) pyriftalid, it is from 0.02 to 5 g, preferably from 0.1 to 3 g.
  • compound B is an organic phosphorus-type compound, it is from 2 to 30 g, preferably from 4 to 25 g.
  • compound B is a cumylamine type compound, it is from 0.2 to 30 g, preferably from 2 to 20 g.
  • compound B is a dinitroaniline type compound, it is from 1 to 15 g, preferably from 2 to 12 g.
  • compound B is a thiocarbamate type compound, it is from 0.2 to 50 g, preferably from 1 to 50 g.
  • compound B is a chloroacetamide type compound, it is from 0.2 to 30 g, preferably from 0.5 to 20 g.
  • compound B is (B49) mefenacet, (B50) cafenstrole, (B51 ) indanofan, (B52) fentrazamide, (B53) oxaziclomefone, (B54) etobenzanid, (B55) benfuresate, (B56) ipfencarbazone or (B57) fenoxasulfone, it is from 0.02 to 30 g, preferably from 0.05 to 20 g.
  • compound B is (B58) quinoclamine, it is from 2 to 50 g, preferably from 6 to 30 g.
  • the herbicidal composition of the present invention may be applied to weeds or may be applied to a place where they grow. Further, it may be applied at any time either before or after the emergence of the weeds. Further, the herbicidal composition of the present invention may take various application forms such as soil application, foliar application, irrigation application, and submerged application, and it can be applied to agricultural fields such as upland fields, orchards and paddy fields, and non- cropland such as ridges of fields, fallow fields, play grounds, golf courses, vacant lands, forests, factory sites, railway sides and roadsides. The herbicidal composition of the present invention is suitably applied to paddy fields.
  • the herbicidal composition of the present invention can control a wide range of undesired plants such as annual weeds and perennial weeds. Specifically, it can control various noxious weeds
  • gramineae such as barnyardgrass (Echinochloa crus-qalli L, Echinochloa oryzicola vasing.), crabgrass (Digitaria sanquinalis L, Diqitaria ischaemum Muhl. , Diqitaria adscendens Henr. , Digitaria microbachne Henr.
  • barnyardgrass Echinochloa crus-qalli L, Echinochloa oryzicola vasing.
  • crabgrass Digitaria sanquinalis L, Diqitaria ischaemum Muhl.
  • Diqitaria adscendens Henr. Digitaria microbachne Henr.
  • alexandergrass (Brachiaria plantaginea), guineaqrass(Panicummaximum Jacq.), paragrass (Panicum purpurascens), sprangletop (Leptochloa chinensis), red
  • sprangletop (Leptochloa panicea), annual bluegrass (Poa annua L), black grass (Alopecurus myosuroides Huds.), cholorado bluestem (Aqropyron tsukushiense
  • cyperaceae such as rice flatsedge (Cyperus iria L.), purple nutsedge (Cvperus rotundus L), yellow nutsedge (Cyperus esculentus L), Japanese * bulrush (Scirpus juncoides), flatsedge (Cvperus serotinus), small-flower umbrellaplant (Cvperus difformis), slender spikerush (Eleocharis acicularis), Eleocharis kuroquwai or Scirpus planiculmis Fr. Schm.; alismataceae such as Japanese ribbon waparo
  • pontederiaceae such as monochoria (Monochoria vaginalis) or monochoria species (Monochoria korsakowii); Scrophulariaceae such as false pimpernel (Lindernia pyxidaria); plantaginaceae such as abunome (Dopatrium
  • lythraceae such as toothcup (Rotala india) or red stem (Ammanniamultiflora); elatinaceae such as long stem waterwort (Elatine triandra SCHK.); malvaceae such as velvetleaf (Abutilon theophrasti MEDIC.) or prickly sida (Sida spinosa L); compositae such as common cocklebur (Xanthium strumarium L), common ragweed (Ambrosia elatior L), thistle (Breea setosa (BIEB.) KITAM.), hairy galinsoga (Galinsoqa ciliata
  • amaranthaceae such as slender amaranth (Amaranthus viridis L.) or redroot pigweed (Amaranthus retroflexus L); polygonanewe such as pale
  • Portulacaceae such as common purslane (Portulacaoleracea L); fabaceae such as sicklepod (Cassia obtusifolia L); caryophyllaceae such as common chickweed (Stellariamedia L.); rubiaceae such as catchweed (Galium spurium L); euphorbiaceae such as threeseeded copperleaf (Acalyphaaustralis L); Commelinaceae such as common dayflower (Commelina communis L). Therefore, it is effectively used in the case of controlling noxious weeds selectively or non-selectively in cultivation of e.g. useful plants such as corn (Zea mays L), soybean (Glycine max Merr.), cotton
  • Vulqare L Vulqare L
  • rye Scalecereale L.
  • oat Avena sativa L
  • sorgo Sorghum bicolor
  • rape (Brassica napus L), sunflower (Helianthus annuus L), power beet (Beta Vulgaris L), power cane (Saccharum officinarum L), Japanese lawngrass (Zovsia japonica stend), peanut (Arachis hypogaea L.), flax (Linum usitatissimum L), tobacco (Nicotiana tabacum L.) or coffee (Coffea spp.).
  • the herbicidal composition of the present invention may be used in combination with the following known herbicidal compounds (such as common names), whereby there may be a case where the range of types of weeds to be controlled, the time for the application, the herbicidal activities, etc. may be improved to a more desirable direction. Even when not specifically mentioned here, in a case where such compounds have salts, alkyl esters, hydrates, different crystal forms, various structural isomers, etc., they are, of course, all included.
  • Those which are believed to exhibit herbicidal effects by disturbing hormone activities of plants such as a phenoxy type such as 2,4-D, 2,4-D-butotyl, 2,4-D-butyl, 2,4-D-dimethylammonium, 2,4-D-diolamine, 2,4-D-ethyl, 2,4-D-2-ethylhexyl, 2,4-D- isobutyl, 2,4-D-isoctyl, 2,4-D-isopropyl, 2,4-D-isopropylammonium, 2,4-D-sodium, 2,4- D-isopropanolammonium, 2,4-D-trolamine, 2,4-DB, 2,4-DB-butyl, 2,4-DB- dimethylammonium, 2,4-DB-isoctyl, 2,4-DB-potassium, 2,4-DB-sodium, dichlorprop, .
  • a phenoxy type such as 2,4-
  • dichlorprop-butotyl dichlorprop-dimethylammonium, dichlorprop-isoctyl, dichlorprop- potassium, dichlorprop-P, dichlorprop-P-dimethylammonium, dichlorprop-P-potassium, dichlorprop-P-sodium, MCPA, MCPA-butotyl, MCPA-dimethylammonium, MCPA-2- ethylhexyl, MCPA-potassium, MCPA-sodium, MCPA-thioethyl, MCPB, MCPB-ethyl, MCPB-sodium, mecoprop, mecoprop-butotyl, mecoprop-sodium, mecoprop-P, mecoprop-P-butotyl, mecoprop-P-dimethylammonium, mecoprop-P-2-ethylhexyl, mecoprop-P-potassium, naproanilide or clome
  • a urea type such as chlorotoluron, diuron, fluometuron, linuron, isoproturon, metobenzuron, tebuthiuron, dimefuron, isouron, karbutilate, methabenzthiazuron, metoxuron, monolinuron, neburon, siduron, terbumeton, trietazine or metobromuron
  • a triazine type such as simazine, atrazine, atratone, simetryn, prometryn, dimethametryn, hexazinone, metribuzin, terbuthylazine, cyanazine, ametryn, cybutryne, triaziflam, indaziflam, terbutryn, propazine, metamitron or prometon
  • a uracil type such as bromacil, bromacyl-lithium, lenacil or terbacil;
  • phenmedipham a hydroxybenzonitrile type such as bromoxynil, bromoxynil-octanoate, bromoxynil-heptanoate, ioxynil, ioxynil-octanoate, ioxynil-potassium or ioxynil-sodium; and others such as pyridate, bentazone, bentazone-sodium, amicarbazone, methazole or pentanochlor.
  • a hydroxybenzonitrile type such as bromoxynil, bromoxynil-octanoate, bromoxynil-heptanoate, ioxynil, ioxynil-octanoate, ioxynil-potassium or ioxynil-sodium
  • others such as pyridate, bentazone, bentazone-sodium, amicarbazone, methazole or pentanochlor.
  • Quaternary ammonium salt type such as paraquat or diquat, which is believed to be converted to free radicals by itself to form active oxygen in the plant body and shows rapid herbicidal efficacy.
  • chlomethoxyfen bifenox, acifluorfen, acifluorfen-sodium, fomesafen, fomesaf en-sodium, oxyfluorfen, lactofen, aclonifen, ethoxyfen-ethyl (HC-252), fluoroglycofen-ethyl or fluoroglycofen; a cyclic imide type such as chlorphthalim, flumioxazin, flumiclorac, flumiclorac-pentyl, cinidon-ethyl, fluthiacet or fluthiacet-methyl; and others such as oxadiargyl, oxadiazon, sulfentrazone, carfentrazone-ethyl, thidiazimin, pentoxazone, azafenidin, isopropazole, pyraflufen-ethyl, benzfendizone, butafenacil,
  • carotenoids such as a pyridazinone type such as norflurazon, chloridazon or metflurazon
  • a pyrazole type such as pyrazolynate, pyrazoxyfen, benzofenap, topramezone or pyrasulfotole
  • others such as amitrole, fluridone, flurtamone, diflufenican, methoxyphenone,
  • clomazone sulcotrione, mesotrione, tembotrione, tefuryltrione (AVH-301), bicyclopyrone, isoxaflutole, difenzoquat, difenzoquat-metilsulfate, isoxachlortole, benzobicyclon, picolinafen, beflubutamid, SW-065, KUH-110, compounds disclosed in the Claims of WO2005118530, compounds disclosed in the Claims of WO2008065907 or compounds disclosed in the Claims of WO2009142318.
  • aryloxyphenoxypropionic acid type such as diclof op-methyl, diclofop, pyriphenop-sodium, fluazifop-butyl, fluazifop, fluazifop-P, fluazifop-P-butyl, haloxyfop- methyl, haloxyfop, haloxyfop-etotyl, haloxyfop-P, haloxyfop-P-methyl, quizalofop-ethyl, quizalofop-P, quizalofop-P-ethyl, quizalofop-P-tefuryl, cyhalofop-butyl, fenoxaprop-ethyl, fenoxaprop-P, fenoxaprop-P-ethyl, metamifop-propyl,
  • sulfonylurea type such as chlorimuron-ethyl, chlorimuron, sulfometuron-methyl, sulfometuron, primisulfuron-methyl, primisulfuron, bensulfuron-methyl, bensulfuron, chlorsulfuron, metsulfuron-methyl, metsulfuron, cinosulfuron, pyrazosulfuron-ethyl, pyrazosulfuron, azimsulfuron, rimsulfuron,
  • a sulfonylurea type such as chlorimuron-ethyl, chlorimuron, sulfometuron-methyl, sulfometuron, primisulfuron-methyl, primisulfuron, bensulfuron-methyl, bensulfuron, chlorsulfuron, metsulfuron-methyl, metsulfuron, cinosulfuron, pyrazosulfuron-ethy
  • pyrithiobac-sodium bispyribac-sodium, pyriminobac-methyl, pyribenzoxim, pyriftalid or pyrimisulfan; a sulfonylaminocarbonyltriazolinone type such as flucarbazone,
  • Those which are believed to exhibit herbicidal effects by inhibiting cell mitoses of plants such as a dinitroaniline type such as trifluralin, oryzalin, nitralin, pendimethalin, ethalfluralin, benfluralin, prodiamine, butralin or dinitramine; an amide type such as bensulide, napropamide, propyzamide or pronamide; an organic phosphorus type such as amiprofos-methyl, butamifos, anilofos or piperophos; a phenyl carbamate type such as propham, chlorpropham, barban or carbetamide; a cumylamine type such as daimuron, cumyluron, bromobutide or methyldymron; and others such as asulam, asuiam-sodium, dithiopyr, thiazopyr, chlorthai-dimethyl, chlorthal or diphenamid.
  • a dinitroaniline type
  • a chloroacetamide type such as alachlor, metazachlor, butachlor, pretilachlor, metolachlor, thenylchlor, pethoxamid, acetochlor, propachlor, dimethenamid, dimethenamid-P, propisochlor or dimethachlor
  • a thiocarbamate type such as molinate, dimepiperate, pyributicarb, EPTC, butylate, vernolate, pebulate, cycloate, prosulfocarb, esprocarb, thiobencarb, diallate, tri-allate or orbencarb
  • others such as etobenzanid, mefenacet, flufenacet, tridiphane, cafenstrole, fentrazamide, oxaziclomefone, indanofan, be
  • MSMA, DSMA, CMA endothall, endothall-dipotassium, endothall-sodium, endothall-mono(N,N-dimethylalkylammonium), ethofumesate, sodium chlorate, pelargonic acid (nonanoic acid), fosamine, fosamine-ammonium, pinoxaden,
  • ipfencarbazone (HOK-201 ), aclolein, ammonium sulfamate, borax, chloroacetic acid, sodium chloroacete, cyanamide, methylarsonic acid, dimethylarsinic acid, sodium dimethylarsinate, dinoterb, dinoterb-ammonium, dinoterb-diolamine, dinoterb-acetate, DNOC, ferrous sulfate, flupropanate, flupropanate-sodium, isoxaben, mefluidide, mefluidide-diolamine, metam, metam-ammonium, metam-potassium, metam-sodium, methyl isothiocyanate, pentachlorophenol, sodium pentachlorophenoxide,
  • the herbicidal composition of the present invention may be prepared by mixing compound A and compound B, as active ingredients, with various agricultural additives in accordance with conventional formulation methods for agricultural chemicals, and applied in various formulations such as dusts, granules, water dispersible granules, wettable powders, tablets, pills, capsules (including a formulation packaged by a water soluble film), water-based suspensions, oil-based suspensions, microemulsions, suspoemulsions, water soluble powders, emulsifiable concentrates, soluble
  • compound A and compound B may be mixed together for the formulation, or they may be separately formulated and may be mixed at the time of application.
  • the additives to be used for the formulation include, for example, a solid carrier such as kaolinite, sericite, diatomaceous earth, slaked lime, calcium carbonate, talc, white carbon, kaoline, bentonite, clay, sodium carbonate, sodium bicarbonate, mirabilite, zeolite or starch; a solvent such as water, toluene, xylene, solvent naphtha, dioxane, dimethylsulfoxide, ⁇ , ⁇ -dimethylformamide, dimethylacetamide, N-methyl-2-pyrrolidone or an alcohol; an anionic surfactant such as a salt of fatty acid, a benzoate, a
  • polycarboxylate a salt of alkylsulfuric acid ester, an alkyl sulfate, an alkylaryl sulfate, an alkyl diglycol ether sulfate, a salt of alcohol sulfuric acid ester, an alkyl sulfonate, an alkylaryl sulfonate, an aryl sulfonate, a lignin sulfonate, an alkyldiphenylether disulfonate, a polystyrene sulfonate, a salt of alkylphosphoric acid ester, an alkylaryl phosphate, a styrylaryl phosphate, a salt of polyoxyethylene alkyl ether sulfuric acid ester, a
  • polyoxyethylene alkylaryl ether sulfate a salt of polyoxyethylene alkylaryl ether sulfuric acid ester, a polyoxyethylene alkyl ether phosphate, a salt of polyoxyethylene alkylaryl phosphoric acid ester, a salt of polyoxyethylene aryl ether phosphoric acid ester, a naphthalene sulfonic acid condensed with formaldehyde or a salt of alkylnaphthalene sulfonic acid condensed with formaldehyde; a nonionic surfactant such as a sorbitan fatty acid ester, a glycerin fatty acid ester, a fatty acid polyglyceride, a fatty acid alcohol polyglycol ether, acetylene glycol, acetylene alcohol, an oxyalkylene block polymer, a polyoxyethylene alkyl ether, a polyoxyethylene alkylaryl ether, a polyoxyethylene styrylary
  • polyoxyethylene fatty acid ester a polyoxyethylene sorbitan fatty acid ester, a
  • polyoxyethylene glycerin fatty acid ester a polyoxyethylene hydrogenated castor oil or a polyoxypropylene fatty acid ester
  • a vegetable oil or mineral oil such as olive oil, kapok oil, castor oil, palm oil, camellia oil, coconut oil, sesame oil, corn oil, rice bran oil, peanut oil, cottonseed oil, soybean oil, rapeseed oil, linseed oil, tung oil or liquid paraffins.
  • additives may suitably be selected for use alone or in combination as a mixture of two or more of them, so long as the object of the present invention is met. Further, additives other than the above-mentioned may be suitably selected for use among those known in this field.
  • various additives commonly used such as a filler, a thickener, an anti-settling agent, an anti-freezing agent, a dispersion stabilizer, a safener, an anti-mold agent, a bubble agent, a disintegrator and a binder, may be used.
  • the mix ratio by weight of the active ingredient to such various additives may be from 0.001 :99.999 to 95:5, preferably from 0.005:99.995 to 90: 10.
  • a proper method can be selected for use among various methods depending upon various conditions such as the application site, the type of the formulation, and the type and the growth stage of the plants to be controlled, and for example, the following methods may be mentioned.
  • Compound A and compound B are mixed and formulated together, and the formulation is diluted to a predetermined concentration with e.g. water, and as the case requires, a spreader (such as a surfactant, a vegetable oil or a mineral oil) is added for application.
  • a spreader such as a surfactant, a vegetable oil or a mineral oil
  • formulations are applied as they are.
  • formulations are diluted to predetermined concentrations with e.g. water as the case requires, and as the case requires, a spreader (such as a surfactant, a vegetable oil or a mineral oil) is added for application.
  • a spreader such as a surfactant, a vegetable oil or a mineral oil
  • formulations are mixed at the time of dilution to a predetermined concentration with e.g. water, and as the case requires, a spreader (such as a surfactant, a vegetable oil or a mineral oil) is added for application.
  • a spreader such as a surfactant, a vegetable oil or a mineral oil
  • the present invention is by no means restricted thereto.
  • the herbicidal composition containing compound A and compound B will be referred to as "the above herbicidal composition”.
  • compound A is a compound of the formula (I) wherein X is 1 ,3-dioxolan-2-yl, R 1 is a chlorine atom, R 2 is methylsulfonyl, Q is a hydrogen atom, and n is 2 (hereinafter referred to simply as compound A1).
  • compound A2 The above herbicidal composition wherein compound A is a sodium salt of the compound as defined in the above (1) (hereinafter referred to simply as compound A2).
  • compound B is at least one phenoxy acetic acid type compound selected from the group consisting of (B1) 2,4-D, or its salt or ester, (B2) MCP, or its salt or ester, (B3) MCPB, or its salt or ester, and (B4) clomeprop.
  • compound B is at least one triazine type compound selected from the group consisting of (B5) simetryn and (B6) dimethametryn.
  • compound B is at least one heterocyclic compound selected from the group consisting of (B8) oxadiazon, (B9) oxadiargyl, (B10) pentoxazone, (B11 ) pyraclonil and (B12) carfentrazone-ethyl.
  • protoporphyrinogen oxidase-inhibiting herbicide selected from heterocyclic compounds defined in the above (8).
  • compound B is at least one pyrazole type compound selected from the group consisting of (B13) pyrazolynate, (B14) pyrazoxyfen and (B15) benzofenap.
  • compound B is at least one triketone type compound selected from the group consisting of (B16) benzobicyclon, (B17) mesotrione, (B18) tefuryltrione, (B19) a compound of the above formula (II) and (B63) a compound of the above formula (IV).
  • compound B is at least one aryloxyphenoxypropionic acid type compound selected from the group consisting of (B21) cyhalofop-butyl and (B22) metamifop.
  • compound B is at least one sulfonylurea type compound selected from the group consisting of (B23) bensulfuron- methyl, (B24) pyrazosulfuron-ethyl, (B25) imazosulfuron, (B26) azimsulfuron, (B27) cyclosulfamuron, (B28) ethoxysulfuron, (B29) halosulfuron-methyl, (B30)
  • compound B is at least one pyrimidinylsalicylic acid-type compound selected from the group consisting of (B34) pyriminobac-methyl and (B35) bispyribac-sodium.
  • compound B is at least one sulfonanilide type compound selected from the group consisting of (B36) pyrimisulfan and (B37) triafamone.
  • compound B is at least one cumylamine type compound selected from the group consisting of (B40) daimuron,
  • compound B is a cell mitoses- inhibiting herbicide selected from the organic phosphorus type compound as defined in the above (20), the cumylamine type compound as defined in the above (21) and (B62) pendimethalin.
  • compound B is at least one thiocarbamate type compound selected from the group consisting of (B43) molinate, (B44) esprocarb, (B45) pyributicarb and (B60) thiobencarb.
  • compound B is at least one chloroacetamide type compound selected from the group consisting of (B46) butachlor, (B47) pretilachlor and (B48) thenylchlor.
  • biosynthesis-inhibiting herbicide selected from the thiocarbamate compound as defined in the above (23), the chloroacetamide compound as defined in the above (24), (B49) mefenacet, (B50) cafenstrole, (B51) indanofan, (B52) fentrazamide, (B53)
  • a method for controlling weeds or inhibiting their growth which comprises applying a herbicidally effective amount of the herbicidal composition as defined in any one of the above (1) to (28) to the weeds or to a place where they grow.
  • a method for controlling weeds or inhibiting their growth which comprises applying a herbicidally effective amount of compound A1 and a herbicidally effective amount of compound B to the weeds or to a place where they grow.
  • a method for controlling weeds or inhibiting their growth which Comprises applying a herbicidally effective amount of compound A2 and a herbicidally effective amount of compound B to the weeds or to a place where they grow.
  • a method for controlling weeds or inhibiting their growth which comprises applying a herbicidally effective amount of compound A1 and a herbicidally effective amount of each compound B as defined in any one of the above (3) to (26) to the weeds or to a place where they grow.
  • a method for controlling weeds or inhibiting their growth which comprises applying a herbicidally effective amount of compound A2 and a herbicidally effective amount of each compound B as defined in any one of the above (3) to (26) to the weeds or to a place where they grow.
  • compound A2 is as defined above and its chemical name is sodium 2-(3-(2-(1 ,3-dioxolan-2-yl)ethoxy)-2-chloro-4- (methylsulfonyl)benzoyl)-3-oxo-1-cyclohexenolate.
  • Paddy soil was put into a 1/10,000 are pot to simulate a paddy field, and tubers of
  • Scirpus planiculmis Fr. Schm. were planted and left to stand under an irrigated condition with a water depth of 3.5 cm.
  • compound A and compound B were, respectively, applied in predetermined amounts.
  • the state of growth of Scirpus planiculmis Fr. Schm. was visually observed and investigated.
  • the growth inhibition rate (%) evaluated in accordance with the following evaluation standard, and as a calculated value, the growth inhibition rate (%) calculated by the Colby's formula (WEED, vol.15, pages 20 to 22, 1967) are,
  • Paddy soil was put into a 1/10,000 are pot to simulate a paddy field, and seeds of barnyardgrass (Echinochloa oryzicola vasing.) were sown, and left to stand under an irrigated condition with a water depth of 3.5 cm.
  • barnyardgrass Echinochloa oryzicola vasing.
  • compound A and compound B were, respectively, applied in predetermined amounts.
  • the growth inhibition rates (%) evaluated in the same manner as in Test Example 1 are shown in Tables 2-1 to 2-9.
  • Paddy soil was put into a 1/10,000 are pot to simulate a paddy field, and tubers of arrow-head (Sagittaria trifolia L.) (sulfonyl urea resistant) were planted and left to stand under an irrigated condition with a water depth of 3.5 cm.
  • arrow-head Sagittaria trifolia L.
  • compound A and compound B were, respectively, applied in predetermined amounts.
  • the state of growth of arrow-head was visually observed and investigated.
  • the growth inhibition rates (%) evaluated in the same manner as in the above Test Example 1 are shown in Tables 3-1 to 3-3. TABLE 3-1 (arrow-head (Saqittaria trifolia L.):initial stage of emergence, investigation date: 28th da after a lication of herbicide
  • Paddy soil was put into a 1/10,000 are pot to simulate a paddy field, and tubers of arrow-head (Sagittaria trifolia L.) (sulfonyl urea sensitive) were planted and left to stand under an irrigated condition with a water depth of 3.5 cm.
  • arrow-head Sagittaria trifolia L.
  • compound A and compound B were, respectively, applied in predetermined amounts.
  • the state of growth of arrow-head was visually observed and investigated.
  • the growth inhibition rates (%) evaluated in the same manner as in the above Test Example 1 are shown in Tables 4-1 to 4-3.
  • Paddy soil was put into a 1/10,000 are pot to simulate a paddy field, and seeds of
  • Japanese bulrush (Scirpus iuncoides) (sulfonylurea sensitive and resistant present as mixed) were sown, and left to stand under an irrigated condition with a water depth of 3.5 cm.
  • compound A and compound B were, respectively, applied in predetermined amounts.
  • paddy water was once removed to a water depth of about 1 cm and then increased again to a water depth of 3.5 cm.
  • the growth inhibition rates (%) evaluated in the same manner as in the above Test Example 1 are shown in Tables 5-1 to 5-3.
  • composition having a broad herbicidal spectrum, having high activity and having a long- lasting effect.

Landscapes

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

Description

DESCRIPTION
TITLE OF INVENTION: HERBICIDAL COMPOSITION TECHNICAL FIELD
The present invention relates to a herbicidal composition comprising a compound represented by the formula (I) given hereinafter and another herbicidal compound.
BACKGROUND ART
Patent Document 1 discloses a certain triketone compound, and it is disclosed that the compound can be used as mixed or combined with other agricultural chemicals, fertilizers, phytotoxicity-reducing agents, etc.
However, it is not known specifically that a herbicidal composition comprising a compound represented by the formula (I) given hereinafter and another herbicidal compound described hereinafter, exhibits synergistic herbicidal effects.
PRIOR ART DOCUMENT PATENT DOCUMENT
Patent Document 1 : JP-A-2006-16389
DISCLOSURE OF INVENTION TECHNICAL PROBLEM
At present, many herbicidal compositions have been developed and used, but there are a variety of types of weeds to be controlled, and their development lasts for a long period of time. Thus, a herbicidal composition having a broad herbicidal spectrum, having high activity and having a long-lasting effect has been desired.
SOLUTION TO PROBLEM
By combining a compound represented by the following formula (I) and another herbicidal compound, it is possible to provide a herbicidal composition having a broad herbicidal spectrum, having high activity and having a long-lasting effect.
That is, the present invention relates to a herbicidal composition comprising (A) a
I) or its salt:
Figure imgf000002_0001
wherein X is a 5- or 6-membered saturated heterocyclic group containing one or two hetero atoms of at least one type selected from the group consisting of an oxygen atom and a sulfur atom (said heterocyclic group may be substituted by alkyl), or
dialkoxymethyl, R1 is halogen, R2 is alkyl, haloalkyl, alkoxy, haloalkoxy, alkylthio, haloalkylthio, alkylsulfinyl, haloalkylsulfinyl, alkylsulfonyl, haloalkylsulfonyl,
dialkylaminosulfonyl, di(haloalkyl)aminosulfonyl, nitro or cyano, Q is a hydrogen atom or benzoyl, and n is 1 or 2, and (B) at least one compound selected from the group consisting of (B1) 2,4-D, or its salt or ester, (B2) MCP, or its salt or ester, (B3) MCPB, or its salt or ester, (B4) clomeprop, (B5) simetryn, (B6) dimethametryn, (B7) bentazone, (B8) oxadiazon, (B9) oxadiargyl, (B10) pentoxazone, (B11) pyraclonil, (B12) carfentrazone-ethyl, (B13) pyrazolynate, (B14) pyrazoxyfen, (B15) benzofenap, (B16) benzobicyclon, (B17) mesotrione, (B18) tefuryltrione, (B19) a compound represented by
he formula (III):
Figure imgf000003_0001
(B21) cyhalofop-butyl, (B22) metamifop, (B23) bensulfuron-methyl, (B24)
pyrazosulfuron-ethyl, (B25) imazosulfuron, (B26) azimsulfuron, (B27) cyclosulfamuron, (B28) ethoxysulfuron, (B29) halosulfuron-methyl, (B30) flucetosulfuron, (B31) propyrisulfuron, (B32) metazosulfuron, (B33) penoxsulam (B34) pyriminobac-methyl, (B35) bispyribac-sodium, (B36) pyrimisulfan, (B37) triafamone, (B38) pyriftalid, (B39) butamifos, (B40) daimuron, (B41) cumyluron, (B42) bromobutide, (B43) molinate, (B44) esprocarb, (B45) pyributicarb, (B46) butachlor, (B47) pretilachlor, (B48) thenylchlor, (B49) mefenacet, (B50) cafenstrole, (B51) indanofan, (B52) fentrazamide, (B53) oxaziclomefone, (B54) etobenzanid, (B55) benfuresate, (B56) ipfencarbazone, (B57) fenoxasulfone, (B58) quinoclamine, (B59) quinclorac, (B60) thiobencarb, (61) clomazone, (B62) pendimethalin and (B63) a compound represented by the formula (IV):
Figure imgf000003_0002
Further, the present invention relates to a method for controlling weeds or inhibiting their growth, which comprises applying a herbicidally effective amount of the above herbicidal composition to weeds or to a place where they grow. Further, the present invention relates to a method for controlling weeds or inhibiting their growth, which comprises applying a herbicidally effective amount of the compound A and a herbicidally effective amount of the compound B to weeds or to a place where they grow.
ADVANTAGEOUS EFFECTS OF INVENTION
According to the present invention, it is possible to provide a herbicidal
composition having a broad herbicidal spectrum, having high activity and having a long- lasting effect. DESCRIPTION OF EMBODIMENTS
The compound of the above formula (I) or its salt is a known compound disclosed in JP-A-2006-16389.
In the formula (I), the 5- or 6-membered saturated heterocyclic group containing one or more hetero atoms of at least one type selected from the group consisting of an oxygen atom and a sulfur atom, for X, may, for example, be tetrahydrofuran-2-yl, tetrahydrofuran-3-yl, dioxolan-2-yl, dioxolan-4-yl, tetrahydropyran-2-yl, 1 ,4-dioxan-2-yl, 1 ,3-dioxan-2-yl, 1 ,3-dioxan-4-yl, tetrahydrothiofen-2-yl, tetrahydrothiopyran-2-yl, 1 ,3- dithian-2-yl, 1 ,4-dithian-2-yl, 1 ,4-thioxan-2-yl or 1 ,4-thioxan-3-yl. Further, such a heterocyclic group may be substituted by alkyl. Such alkyl has from 1 to 6 carbon atoms and may be linear or branched.
In the formula (I), the alkyl or alkyl moiety for X or R2 may be a C1.6 linear or branched one, such as methyl, ethyl, propyl, isopropyl, butyl, tert-butyl, pentyl or hexyl.
In the formula (I), the halogen or halogen as a substituent for R1 or R2 may be an atom of fluorine, chlorine, bromine or iodine. The number of halogen atoms as substituents may be 1 , or 2 or more, and in the case of 2 or more, the respective halogen atoms may be the same or different. Further, the substitution position of halogen may be any position.
The salt of the compound of the formula (I) may be any salt so long as it is agriculturally acceptable, and it may, for example, be an alkali metal salt such as a sodium salt, a potassium salt or a lithium salt; an alkaline earth metal salt such as a magnesium salt, a calcium salt or a barium salt; or an ammonium salt such as a NH4+ salt, a dimethylamine salt or a triethylamine salt.
Now, the compound B will be described. The compound B is represented by a common name or a chemical structural formula.
(B1) 2,4-D, or its salt or ester, (B2) MCP, or its salt or ester, (B3) MCPB, or its salt or ester, and (B4) clomeprop, are phenoxy acetic acid type compounds. Such phenoxy acetic acid type compounds and (B59) quinclorac are classified into a plant hormone active (auxin active) disturbing herbicide. Specific examples of the above (B1) include 2,4-D, 2,4-D sodium, 2,4-D dimethylammonium, 2,4-D diethylammonium, 2,4-D diethanolammonium, 2,4-D lithium, 2,4-D ethyl, 2,4-D isopropyl, 2,4-D butyl, 2,4-D isooctyl, etc. Specific examples of the above (B2) include MCP (or MCPA), MCP sodium, MCP potassium, MCP calcium, MCP lithium, MCP dimethylammonium, MCP benzyl triethanol ammonium, MCP ethyl, MCP butyl, MCP isooctyl, MCP allyl, etc.
Specific examples of the above (B3) include MCPB, MCPB sodium, MCPB ethyl, etc.
(B5) simetryn and (B6) dimethametryn are triazine type compounds. (B7) bentazone is a pyrimidine type compound. Such triazine type compounds and pyrimidine type compound, are classified into a photosynthesis-inhibiting herbicide.
(B8) oxadiazon, (B9) oxadiargyl, (B10) pentoxazone, (B11) pyraclonil and (B12) carfentrazone-ethyl are heterocyclic compounds. Such heterocyclic compounds are classified into a protoporphyrinogen oxidase-inhibiting herbicide.
(B13) pyrazolynate, (B14) pyrazoxyfen and (B15) benzofenap are pyrazole type compounds. (B16) benzobicyclon, (B17) mesotrione, (B18) tefuryltrione, (B19) a compound of the formula (II) and (B63) a compound of the formula (IV) are triketone- type compounds. Such pyrazole type compounds and triketone-type compounds as well as (B20) a compound of the above formula (III) and (B61) clomazone are classified into a 4-hydroxyphenyl pyruvic acid-inhibiting herbicide.
(B21) cyhalofop-butyl and (B22) metamifop are aryloxyphenoxy propionic acid- type compounds. Such aryloxyphenoxy propionic acid-type compounds are classified into an acetyl CoA carboxylase-inhibiting herbicide.
(B23) bensulfuron-methyl, (B24) pyrazosulfuron-ethyl, (B25) imazosulfuron, (B26) azimsulfuron, (B27) cyclosulfamuron, (B28) ethoxysulfuron, (B29) halosulfuron-methyl, (B30) flucetosulfuron, (B31) propyrisulfuron and (B32) metazosulfuron are sulfonylurea type compounds. (B33) penoxsulam is a sulfone amide-type compound. (B34) pyriminobac-methyl and (B35) bispyribac-sodium are pyrimidinylsalicylic acid-type compounds. (B36) pyrimisulfan and (B37) triafamone are sulfone anilide-type compounds. Such sulfonylurea-type compounds, sulfoneamide-type compounds, pyrimidinylsalicylic acid-type compounds and sulfone anilide-type compounds, as well as (B38) pyriftalid, are classified into an acetolactate synthetase-inhibiting herbicide.
(B39) butamifos is an organic phosphorus compound. (B40) daimuron, (B41 ) cumyluron and (B42) bromobutide are cumylamine-type compounds. (B62)
pendimethalin is a dinitroaniline-type compound. Such organic phosphorus compound, cumylamine-type compounds and dinitroaniline-type compound are classified into a cell mitoses-inhibiting herbicide.
(B43) molinate, (B44) esprocarb, (B45) pyributicarb and (B60) thiobencarb are thiocarbamate-type compounds. (B46) butachlor, (B47) pretilachlor and (B48) thenylchlor are chloroacetamide-type compounds. Such thiocarbamate-type
compounds and chloroacetamide-type compounds as well as (B49) mefenacet, (B50) cafenstrole, (B51) indanofan, (B52) fentrazamide, (B53) oxaziclomefone, (B54) etobenzanid, (B55) benfuresate, (B56) ipfencarbazone and (B57) fenoxasulfone are classified into a lipid biosynthesis-inhibiting herbicide.
(B58) quinoclamine is a naphthoquinone type compound.
The mixing ratio of compound A and compound B cannot generally be defined, as it is required to be suitably adjusted depending upon the type of the formulation, the weather conditions, and the type and the growth stage of weeds to be controlled.
However, compound B is, for example, from 0.0005 to 500 parts by weight, preferably from 0.002 to 100 parts by weight, more preferably from 0.005 to 100 parts by weight, to 1 part by weight of compound A. However, depending upon the above-mentioned various conditions, it is possible to select the mixing ratio outside of such ranges.
Now, the mixing ratio of compound A and compound B will be exemplified for the above-mentioned every type of compound B. The weight ratio of each type of compound B to 1 part by weigh of compound A is as follows. However, as mentioned above, such a mixing ratio cannot generally be defined, as it is required to be suitably adjusted depending upon various conditions, and it is also possible to select a mixing ratio outside of such a range. Further, it should be understood that the present invention is by no means restricted by such descriptions.
In a case where compound B is a phenoxy acetic acid type compound, its ratio is from 0.01 to 100 parts by weight, preferably from 0.1 to 11 parts by weight, further preferably from 0.2 to 10 parts by weight.
In a case where compound B is (B59) quinclorac, its ratio is from 0.01 to 100 parts by weight, preferably from 0.1 to 10 parts by weight, further preferably from 0.2 to 10 parts by weight.
In a case where compound B is a triazine type compound, its ratio is from 0.002 to
100 parts by weight, preferably from 0.02 to 10 parts by weight, further preferably from 0.05 to 10 parts by weight.
In a case where compound B is a pyrimidine type compound, its ratio is from 0.2 to 500 parts by weight, preferably from 1.6 to 80 parts by weight, further preferably from 4 to 70 parts by weight.
In a case where compound B is a heterocyclic compound, its ratio is from 0.002 to 100 parts by weight, preferably from 0.02 to 16 parts by weight, further preferably from 0.05 to 15 parts by weight.
In a case where compound B is a pyrazole type compound, its ratio is from 0.02 to 500 parts by weight, preferably from 0.4 to 70 parts by weight, further preferably from 1 to 60 parts by weight.
In a case where compound B is a triketone type compound, its ratio is from 0.01 to 50 parts by weight, preferably from 0.04 to 7 parts by weight, further preferably from 0.1 to 7 parts by weight.
In a case where compound B is (B20) a compound of the above formula (III), its ratio is from 0.005 to 300 parts by weight, preferably from 0.02 to 30 parts by weight, further preferably from 0.05 to 25 parts by weight.
In a case where compound B is (B61) clomazone, its ratio is from 0.01 to 100 parts by weight, preferably from 0.1 to 16 parts by weight, further preferably from 0.2 to 15 parts by weight.
In a case where compound B is an aryloxyphenoxypropionic acid type compound, its ratio is from 0.01 to 50 parts by weight, preferably from 0.04 to 7 parts by weight, further preferably from 0.1 to 6 parts by weight.
In a case where compound B is a sulfonylurea compound, its ratio is from 0.0005 to 30 parts by weight, preferably from 0.002 to 3 parts by weight, further preferably from 0.005 to 2.5 parts by weight.
In a case where compound B is a sulfonamide type compound, its ratio is from 0.002 to 20 parts by weight, preferably from 0.01 to 2 parts by weight, further preferably from 0.02 to 2 parts by weight.
In a case where compound B is a pyrimidinylsalicylic acid type compound, its ratio is from 0.001 to 30 parts by weight, preferably from 0.004 to 3 parts by weight, further preferably from 0.01 to 2.5 parts by weight.
In a case where compound B is a sulfonanilide type compound, its ratio is from
0.002 to 15 parts by weight, preferably from 0.02 to 1.6 parts by weight, further preferably from 0.05 to 1.5 parts by weight.
In a case where compound B is (B38) pyriftalid, its ratio is from 0.002 to 50 parts by weight, preferably from 0.02 to 6 parts by weight, further preferably from 0.1 to 5 parts by weight.
In a case where compound B is an organic phosphorus-type compound, its ratio is from 0.2 to 300 parts by weight, preferably from 0.8 to 50 parts by weight, further preferably from 2 to 40 parts by weight.
In a case where compound B is a cumylamine type compound, its ratio is from 0.02 to 300 parts by weight, preferably from 0.4 to 40 parts by weight, further preferably from 1 to 30 parts by weight.
In a case where compound B is a dinitroaniline type compound, its ratio is from 0.1 to 150 parts by weight, preferably from 0.4 to 24 parts by weight, further preferably from 0.2 to 24 parts by weight.
In a case where compound B is a thiocarbamate type compound, its ratio is from
0.02 to 500 parts by weight, preferably from 0.2 to 100 parts by weight, further preferably from 0.5 to 100 parts by weight.
In a case where compound B is a chloroacetamide type compound, its ratio is from 0.02 to 300 parts by weight, preferably from 0.1 to 40 parts by weight, further preferably from 0.3 to 35 parts by weight.
In a case where compound B is (B49) mefenacet, (B50) cafenstrole, (B51) indanofan, (B52) fentrazamide, (B53) oxaziclomefone, (B54) etobenzanid, (B55) benfuresate, (B56) ipfencarbazone or (B57) fenoxasulfone, its ratio is from 0.002 to 300 parts by weight, preferably from 0.01 to 40 parts by weight, further preferably from 0.02 to 30 parts by weight.
In a case where compound B is (B58) quinoclamine, its ratio is from 0.2 to 500 parts by weight, preferably from 1.2 to 60 parts by weight, further preferably from 3 to 50 parts by weight.
The amounts of application of compound A and compound B cannot generally be defined, as they are required to be suitably adjusted depending upon e.g. the mixing ratio of compound A and compound B, the type of the formulation, the weather conditions, and the type and growth stage of weeds to be controlled. However, per 1 are, for example, compound A can be suitably selected within a range of from 0.1 to 10 g, preferably from 0.5 to 5 g, and compound B can be suitably selected within a range of from 0.005 to 50 g, preferably from 0.01 to 50 g, and they may be suitably combined. However, depending upon the above-mentioned various conditions, it is possible to select the amounts of application outside of these ranges.
Now, the amount of application of compound B per 1 are will be exemplified for the above-mentioned every type of compound B. However, as mentioned above, the amount of application cannot generally be defined, as it is required to be suitably adjusted depending upon various conditions, and it is also possible to select the amount of application outside of such a range. Further, it should be understood that the present invention is by no means limited by such descriptions.
In a case where compound B is a phenoxy acetic acid type compound, it is from 0.1 to 10 g, preferably from 0.5 to 5.5 g.
In a case where compound B is (B59) quinclorac, it is from 0.1 to 10 g, preferably from 0.5 to 5 g.
In a case where compound B is a triazine type compound, it is from 0.02 to 10 g, preferably from 0.1 to 5 g.
In a case where compound B is a pyrimidine type compound, it is from 2 to 50 g, preferably from 8 to 40 g.
In a case where compound B is a heterocyclic compound, it is from 0.02 to 10 g, preferably from 0.1 to 8 g.
In a case where compound B is a pyrazole type compound, it is from 0.2 to 50 g, preferably from 2 to 35 g.
In a case where compound B is a triketone type compound, it is from 0.1 to 5 g, preferably from 0.2 to 3.5 g.
In a case where compound B is (B20) a compound of the above formula (III), it is from 0.05 to 30 g, preferably from 0.1 to 15 g.
In a case where compound B is (B61) clomazone, it is from 0.1 to 10 g, preferably from 0.5 to 8 g.
In a case where compound B is an aryloxyphenoxypropionic acid type compound, it is from 0.1 to 5 g, preferably from 0.2 to 3.5 g.
In a case where compound B is a sulfonylurea compound, it is from 0.005 to 3 g, preferably from 0.01 to 1.5 g.
In a case where compound B is a sulfonamide type compound, it is from 0.02 to 2 g, preferably from 0.05 to 1 g.
In a case where compound B is a pyrimidinylsalicylic acid type compound, it is from 0.01 to 3 g, preferably from 0.02 to 1.5 g.
In a case where compound B is a sulfonamide type compound, it is from 0.02 to 1.5 g, preferably from 0.1 to 0.8 g.
In a case where compound B is (B38) pyriftalid, it is from 0.02 to 5 g, preferably from 0.1 to 3 g.
In a case where compound B is an organic phosphorus-type compound, it is from 2 to 30 g, preferably from 4 to 25 g.
In a case where compound B is a cumylamine type compound, it is from 0.2 to 30 g, preferably from 2 to 20 g.
In a case where compound B is a dinitroaniline type compound, it is from 1 to 15 g, preferably from 2 to 12 g.
In a case where compound B is a thiocarbamate type compound, it is from 0.2 to 50 g, preferably from 1 to 50 g.
In a case where compound B is a chloroacetamide type compound, it is from 0.2 to 30 g, preferably from 0.5 to 20 g.
In a case where compound B is (B49) mefenacet, (B50) cafenstrole, (B51 ) indanofan, (B52) fentrazamide, (B53) oxaziclomefone, (B54) etobenzanid, (B55) benfuresate, (B56) ipfencarbazone or (B57) fenoxasulfone, it is from 0.02 to 30 g, preferably from 0.05 to 20 g.
In a case where compound B is (B58) quinoclamine, it is from 2 to 50 g, preferably from 6 to 30 g.
The herbicidal composition of the present invention may be applied to weeds or may be applied to a place where they grow. Further, it may be applied at any time either before or after the emergence of the weeds. Further, the herbicidal composition of the present invention may take various application forms such as soil application, foliar application, irrigation application, and submerged application, and it can be applied to agricultural fields such as upland fields, orchards and paddy fields, and non- cropland such as ridges of fields, fallow fields, play grounds, golf courses, vacant lands, forests, factory sites, railway sides and roadsides. The herbicidal composition of the present invention is suitably applied to paddy fields.
The herbicidal composition of the present invention can control a wide range of undesired plants such as annual weeds and perennial weeds. Specifically, it can control various noxious weeds
including, for example, gramineae such as barnyardgrass (Echinochloa crus-qalli L, Echinochloa oryzicola vasing.), crabgrass (Digitaria sanquinalis L, Diqitaria ischaemum Muhl. , Diqitaria adscendens Henr. , Digitaria microbachne Henr. , Digitaria horizontalis Willd.), greenfoxtail (Setaria viridis L), giant foxtail (Setaria faberi Herrm.), yellow foxtail (Setaria lutescens Hubb.), goosegrass (Eleusine indica L), wild oat (Avena fatua L), johnsongrass (Sorghum halepense L), quackgrass (Aqropyron repens L),
alexandergrass (Brachiaria plantaginea), guineaqrass(Panicummaximum Jacq.), paragrass (Panicum purpurascens), sprangletop (Leptochloa chinensis), red
sprangletop (Leptochloa panicea), annual bluegrass (Poa annua L), black grass (Alopecurus myosuroides Huds.), cholorado bluestem (Aqropyron tsukushiense
(Honda) Ohwi), broadleaf siqnalqrass(Brachiaria platvphylla Nash), southern sandbur (Cenchrus echinatus L), Italian ryegrass (Lolium multiflorum Lam.) or bermudagrass (Cvnodon dactylon Pers.); cyperaceae such as rice flatsedge (Cyperus iria L.), purple nutsedge (Cvperus rotundus L), yellow nutsedge (Cyperus esculentus L), Japanese* bulrush (Scirpus juncoides), flatsedge (Cvperus serotinus), small-flower umbrellaplant (Cvperus difformis), slender spikerush (Eleocharis acicularis), Eleocharis kuroquwai or Scirpus planiculmis Fr. Schm.; alismataceae such as Japanese ribbon waparo
(Sagittaria pyqmaea), arrow-head (Sagittaria trifolia L.) or narrowleaf waterplantain (Alisma canaliculatum); pontederiaceae such as monochoria (Monochoria vaginalis) or monochoria species (Monochoria korsakowii); Scrophulariaceae such as false pimpernel (Lindernia pyxidaria); plantaginaceae such as abunome (Dopatrium
iunceum); lythraceae such as toothcup (Rotala india) or red stem (Ammanniamultiflora); elatinaceae such as long stem waterwort (Elatine triandra SCHK.); malvaceae such as velvetleaf (Abutilon theophrasti MEDIC.) or prickly sida (Sida spinosa L); compositae such as common cocklebur (Xanthium strumarium L), common ragweed (Ambrosia elatior L), thistle (Breea setosa (BIEB.) KITAM.), hairy galinsoga (Galinsoqa ciliata
Blake), wild chamomile (Matricaria chamomilla L.) or henbit (Lamium amplexicaule L); solanaceae such as black nightshade (Solanumniqrum L.) or jimsonweed
(Daturastramonium); amaranthaceae such as slender amaranth (Amaranthus viridis L.) or redroot pigweed (Amaranthus retroflexus L); polygonaceeae such as pale
smartweed (Polyqonumlapathifolium L), ladysthumb (Polyqonumpersicaria L), wild buckwheat (Polygonumconvolvulus L.) or knotweed (Polyqonumaviculare L); cruciferae such as flexuous bittercress (Cardamine flexuosa WITH.), shepherd's-purse (Capsella bursa-pastoris Medik.) or indian mustard (Brassica juncea Czern.); convolvulaceae such as tall morningglory (Ipomoeapurpurea L), field bindweed (Convolvulusarvensis L.) or ivyleaf morningglory (Ipomoeahederacea Jacq.); Amaran thaceae such as common lambsquarters (Chenopodium album L.) or mexican burningbush (Kochia scoparia
Schrad.); Portulacaceae such as common purslane (Portulacaoleracea L); fabaceae such as sicklepod (Cassia obtusifolia L); caryophyllaceae such as common chickweed (Stellariamedia L.); rubiaceae such as catchweed (Galium spurium L); euphorbiaceae such as threeseeded copperleaf (Acalyphaaustralis L); Commelinaceae such as common dayflower (Commelina communis L). Therefore, it is effectively used in the case of controlling noxious weeds selectively or non-selectively in cultivation of e.g. useful plants such as corn (Zea mays L), soybean (Glycine max Merr.), cotton
(Gossypium spp.), wheat (Triticum spp.), rice (Orvza sativa L), barley (Hordeum
Vulqare L), rye (Secalecereale L.), oat (Avena sativa L), sorgo (Sorghum bicolor
Moench), rape (Brassica napus L), sunflower (Helianthus annuus L), suger beet (Beta Vulgaris L), suger cane (Saccharum officinarum L), Japanese lawngrass (Zovsia japonica stend), peanut (Arachis hypogaea L.), flax (Linum usitatissimum L), tobacco (Nicotiana tabacum L.) or coffee (Coffea spp.).
The herbicidal composition of the present invention may be used in combination with the following known herbicidal compounds (such as common names), whereby there may be a case where the range of types of weeds to be controlled, the time for the application, the herbicidal activities, etc. may be improved to a more desirable direction. Even when not specifically mentioned here, in a case where such compounds have salts, alkyl esters, hydrates, different crystal forms, various structural isomers, etc., they are, of course, all included.
(1) Those which are believed to exhibit herbicidal effects by disturbing hormone activities of plants, such as a phenoxy type such as 2,4-D, 2,4-D-butotyl, 2,4-D-butyl, 2,4-D-dimethylammonium, 2,4-D-diolamine, 2,4-D-ethyl, 2,4-D-2-ethylhexyl, 2,4-D- isobutyl, 2,4-D-isoctyl, 2,4-D-isopropyl, 2,4-D-isopropylammonium, 2,4-D-sodium, 2,4- D-isopropanolammonium, 2,4-D-trolamine, 2,4-DB, 2,4-DB-butyl, 2,4-DB- dimethylammonium, 2,4-DB-isoctyl, 2,4-DB-potassium, 2,4-DB-sodium, dichlorprop, . dichlorprop-butotyl, dichlorprop-dimethylammonium, dichlorprop-isoctyl, dichlorprop- potassium, dichlorprop-P, dichlorprop-P-dimethylammonium, dichlorprop-P-potassium, dichlorprop-P-sodium, MCPA, MCPA-butotyl, MCPA-dimethylammonium, MCPA-2- ethylhexyl, MCPA-potassium, MCPA-sodium, MCPA-thioethyl, MCPB, MCPB-ethyl, MCPB-sodium, mecoprop, mecoprop-butotyl, mecoprop-sodium, mecoprop-P, mecoprop-P-butotyl, mecoprop-P-dimethylammonium, mecoprop-P-2-ethylhexyl, mecoprop-P-potassium, naproanilide or clomeprop; an aromatic carboxylic acid type such as 2,3,6-TBA, dicamba, dicamba-butotyl, dicamba-diglycolamine, dicamba- dimethylammonium, dicamba-diolamine, dicamba-isopropylammonium, dicamba- potassium, dicamba-sodium, dichlobenil, picloram, picloram-dimethylammonium, picloram-isoctyl, picloram-potassium, picloram-triisopropanolammonium, picloram- triisopropylammonium, picloram-trolamine, triclopyr, triclopyr-butotyl, triclopyr- triethylammonium, clopyralid, clopyralid-olamine, clopyralid-potassium, clopyralid- triisopropanolammonium or aminopyralid; and others such as naptalam, naptalam- sodium, benazolin, benazolin-ethyl, quinclorac, quinmerac, diflufenzopyr, diflufenzopyr- sodium, fluroxypyr, fluroxypyr-2-butoxy-1-methylethyl, fluroxypyr-meptyl, chlorflurenol, chlorflurenol-methyl, aminocyclopyrachlor, aminocyclopyrachlor-methyl or
aminocyclopyrachlor-potassium.
(2) Those which are believed to exhibit herbicidal effects by inhibiting
photosynthesis of plants, such as a urea type such as chlorotoluron, diuron, fluometuron, linuron, isoproturon, metobenzuron, tebuthiuron, dimefuron, isouron, karbutilate, methabenzthiazuron, metoxuron, monolinuron, neburon, siduron, terbumeton, trietazine or metobromuron; a triazine type such as simazine, atrazine, atratone, simetryn, prometryn, dimethametryn, hexazinone, metribuzin, terbuthylazine, cyanazine, ametryn, cybutryne, triaziflam, indaziflam, terbutryn, propazine, metamitron or prometon; a uracil type such as bromacil, bromacyl-lithium, lenacil or terbacil; an anilide type such as propanil or cypromid; a carbamate type such as swep, desmedipham or
phenmedipham; a hydroxybenzonitrile type such as bromoxynil, bromoxynil-octanoate, bromoxynil-heptanoate, ioxynil, ioxynil-octanoate, ioxynil-potassium or ioxynil-sodium; and others such as pyridate, bentazone, bentazone-sodium, amicarbazone, methazole or pentanochlor.
(3) Quaternary ammonium salt type such as paraquat or diquat, which is believed to be converted to free radicals by itself to form active oxygen in the plant body and shows rapid herbicidal efficacy.
(4) Those which are believed to exhibit herbicidal effects by inhibiting chlorophyll biosynthesis of plants and abnormally accumulating a photosensitizing peroxide substance in the plant body, such as a diphenylether type such as nitrofen,
chlomethoxyfen, bifenox, acifluorfen, acifluorfen-sodium, fomesafen, fomesaf en-sodium, oxyfluorfen, lactofen, aclonifen, ethoxyfen-ethyl (HC-252), fluoroglycofen-ethyl or fluoroglycofen; a cyclic imide type such as chlorphthalim, flumioxazin, flumiclorac, flumiclorac-pentyl, cinidon-ethyl, fluthiacet or fluthiacet-methyl; and others such as oxadiargyl, oxadiazon, sulfentrazone, carfentrazone-ethyl, thidiazimin, pentoxazone, azafenidin, isopropazole, pyraflufen-ethyl, benzfendizone, butafenacil, saflufenacil, flupoxam, fluazolate, profluazol, pyraclonil, flufenpyr-ethyl, bencarbazone or ethyl[3-(2- chloro-4-fluoro-5-(3-methyl-2,6-dioxo-4-trifluoromethyl-3,6-dihydro-2H-pyrimidin-1- yl)phenoxy)pyridin-2-yloxy]acetate (SYN-523). (5) Those which are believed to exhibit herbicidal effects characterized by bleaching activities by inhibiting chromogenesis of plants such as carotenoids, such as a pyridazinone type such as norflurazon, chloridazon or metflurazon; a pyrazole type such as pyrazolynate, pyrazoxyfen, benzofenap, topramezone or pyrasulfotole; and others such as amitrole, fluridone, flurtamone, diflufenican, methoxyphenone,
clomazone, sulcotrione, mesotrione, tembotrione, tefuryltrione (AVH-301), bicyclopyrone, isoxaflutole, difenzoquat, difenzoquat-metilsulfate, isoxachlortole, benzobicyclon, picolinafen, beflubutamid, SW-065, KUH-110, compounds disclosed in the Claims of WO2005118530, compounds disclosed in the Claims of WO2008065907 or compounds disclosed in the Claims of WO2009142318.
(6) Those which exhibit strong herbicidal effects specifically to gramineous plants, such as an aryloxyphenoxypropionic acid type such as diclof op-methyl, diclofop, pyriphenop-sodium, fluazifop-butyl, fluazifop, fluazifop-P, fluazifop-P-butyl, haloxyfop- methyl, haloxyfop, haloxyfop-etotyl, haloxyfop-P, haloxyfop-P-methyl, quizalofop-ethyl, quizalofop-P, quizalofop-P-ethyl, quizalofop-P-tefuryl, cyhalofop-butyl, fenoxaprop-ethyl, fenoxaprop-P, fenoxaprop-P-ethyl, metamifop-propyl, metamifop, clodinafop-propargyl, clodinafop or propaquizafop; a cyclohexanedione type such as alloxydim-sodium, alloxydim, clethodim, sethoxydim, tralkoxydim, butroxydim, tepraloxydim, profoxydim or cycloxydim; and others such as flamprop-M-methyl, flamprop-M or flamprop-M-isopropyl.
(7) Those which are believed to exhibit herbicidal effects by inhibiting an amino acid biosynthesis of plants, such as a sulfonylurea type such as chlorimuron-ethyl, chlorimuron, sulfometuron-methyl, sulfometuron, primisulfuron-methyl, primisulfuron, bensulfuron-methyl, bensulfuron, chlorsulfuron, metsulfuron-methyl, metsulfuron, cinosulfuron, pyrazosulfuron-ethyl, pyrazosulfuron, azimsulfuron, rimsulfuron,
nicosulfuron, flazasulfuron, imazosulfuron, cyclosulfamuron, prosulfuron, flupyrsulfuron- methyl-sodium, flupyrsulfuron, triflusulfuron-methyl, triflusulfuron, halosulfuron-methyl, halosulfuron, thifensulfuron-methyl, thifensulfuron, ethoxysulfuron, oxasulfuron, ethametsulfuron, ethametsulfuron-methyl, iodosulfuron, iodosulfuron-methyl-sodium, sulfosulfuron, triasulfuron, tribenuron-methyl, tribenuron, tritosulfuron, foramsulfuron, trifloxysulfuron, trifloxysulfuron-sodium, mesosulfuron-methyl, mesosulfuron,
orthosulfamuron, flucetosulfuron, amidosulfuron, propyrisulfuron (TH-547),
metazosulfuron, iofensulfuron, or compounds disclosed in the claims of EP0645386; a triazolopyrimidinesulfonamide type such as flumetsulam, metosulam, diclosulam, cloransulam-methyl, florasulam, penoxsulam or pyroxsulam; an imidazolinone type such as imazapyr, imazapyr-isopropylammonium, imazethapyr, imazethapyr-ammonium, imazaquin, imazaquin-ammonium, imazamox, imazamox-ammonium, imazamethabenz, imazamethabenz-methyl or imazapic; a pyrimidinylsalicylic acid type such as
pyrithiobac-sodium, bispyribac-sodium, pyriminobac-methyl, pyribenzoxim, pyriftalid or pyrimisulfan; a sulfonylaminocarbonyltriazolinone type such as flucarbazone,
flucarbazone-sodium, propoxycarbazone-sodium, propoxycarbazone or thiencarbazone; and others such as glyphosate, glyphosate-sodium, glyphosate-potassium, glyphosate- ammonium, glyphosate-diammonium, glyphosate-isopropylammonium, glyphosate- trimesium, glyphosate-sesquisodium, glufosinate, glufosinate-ammonium, glufosinate-P, glufosinate-P-ammonium, glufosinate-P-sodium, bilanafos, bilanafos-sodium,
cinmethylin or triafamone.
(8) Those which are believed to exhibit herbicidal effects by inhibiting cell mitoses of plants, such as a dinitroaniline type such as trifluralin, oryzalin, nitralin, pendimethalin, ethalfluralin, benfluralin, prodiamine, butralin or dinitramine; an amide type such as bensulide, napropamide, propyzamide or pronamide; an organic phosphorus type such as amiprofos-methyl, butamifos, anilofos or piperophos; a phenyl carbamate type such as propham, chlorpropham, barban or carbetamide; a cumylamine type such as daimuron, cumyluron, bromobutide or methyldymron; and others such as asulam, asuiam-sodium, dithiopyr, thiazopyr, chlorthai-dimethyl, chlorthal or diphenamid.
(9) Those which are believed to exhibit herbicidal effects by inhibiting protein biosynthesis or lipid biosynthesis of plants, such as a chloroacetamide type such as alachlor, metazachlor, butachlor, pretilachlor, metolachlor, thenylchlor, pethoxamid, acetochlor, propachlor, dimethenamid, dimethenamid-P, propisochlor or dimethachlor; a thiocarbamate type such as molinate, dimepiperate, pyributicarb, EPTC, butylate, vernolate, pebulate, cycloate, prosulfocarb, esprocarb, thiobencarb, diallate, tri-allate or orbencarb; and others such as etobenzanid, mefenacet, flufenacet, tridiphane, cafenstrole, fentrazamide, oxaziclomefone, indanofan, benfuresate, pyroxasulfone, fenoxasulfone, dalapon, dalapon-sodium, TCA-sodium or trichloroacetic acid.
(10) MSMA, DSMA, CMA, endothall, endothall-dipotassium, endothall-sodium, endothall-mono(N,N-dimethylalkylammonium), ethofumesate, sodium chlorate, pelargonic acid (nonanoic acid), fosamine, fosamine-ammonium, pinoxaden,
ipfencarbazone (HOK-201 ), aclolein, ammonium sulfamate, borax, chloroacetic acid, sodium chloroacete, cyanamide, methylarsonic acid, dimethylarsinic acid, sodium dimethylarsinate, dinoterb, dinoterb-ammonium, dinoterb-diolamine, dinoterb-acetate, DNOC, ferrous sulfate, flupropanate, flupropanate-sodium, isoxaben, mefluidide, mefluidide-diolamine, metam, metam-ammonium, metam-potassium, metam-sodium, methyl isothiocyanate, pentachlorophenol, sodium pentachlorophenoxide,
pentachlorophenol laurate, quinoclamine, sulfuric acid, urea sulfate, methiozolin (MRC- 01), etc.
(11) Those which are believed to exhibit herbicidal effects by being parasitic on plants, such as Xanthomonas campestris, Epicoccosirus nematosorus, Epicoccosirus nematosperus, Exserohilum monoseras or Drechsrela monoceras.
The herbicidal composition of the present invention may be prepared by mixing compound A and compound B, as active ingredients, with various agricultural additives in accordance with conventional formulation methods for agricultural chemicals, and applied in various formulations such as dusts, granules, water dispersible granules, wettable powders, tablets, pills, capsules (including a formulation packaged by a water soluble film), water-based suspensions, oil-based suspensions, microemulsions, suspoemulsions, water soluble powders, emulsifiable concentrates, soluble
concentrates or pastes. It may be formed into any formulation which is commonly used in this field, so long as the object of the present invention is thereby met.
At the time of the formulation, compound A and compound B may be mixed together for the formulation, or they may be separately formulated and may be mixed at the time of application.
The additives to be used for the formulation include, for example, a solid carrier such as kaolinite, sericite, diatomaceous earth, slaked lime, calcium carbonate, talc, white carbon, kaoline, bentonite, clay, sodium carbonate, sodium bicarbonate, mirabilite, zeolite or starch; a solvent such as water, toluene, xylene, solvent naphtha, dioxane, dimethylsulfoxide, Ν,Ν-dimethylformamide, dimethylacetamide, N-methyl-2-pyrrolidone or an alcohol; an anionic surfactant such as a salt of fatty acid, a benzoate, a
polycarboxylate, a salt of alkylsulfuric acid ester, an alkyl sulfate, an alkylaryl sulfate, an alkyl diglycol ether sulfate, a salt of alcohol sulfuric acid ester, an alkyl sulfonate, an alkylaryl sulfonate, an aryl sulfonate, a lignin sulfonate, an alkyldiphenylether disulfonate, a polystyrene sulfonate, a salt of alkylphosphoric acid ester, an alkylaryl phosphate, a styrylaryl phosphate, a salt of polyoxyethylene alkyl ether sulfuric acid ester, a
polyoxyethylene alkylaryl ether sulfate, a salt of polyoxyethylene alkylaryl ether sulfuric acid ester, a polyoxyethylene alkyl ether phosphate, a salt of polyoxyethylene alkylaryl phosphoric acid ester, a salt of polyoxyethylene aryl ether phosphoric acid ester, a naphthalene sulfonic acid condensed with formaldehyde or a salt of alkylnaphthalene sulfonic acid condensed with formaldehyde; a nonionic surfactant such as a sorbitan fatty acid ester, a glycerin fatty acid ester, a fatty acid polyglyceride, a fatty acid alcohol polyglycol ether, acetylene glycol, acetylene alcohol, an oxyalkylene block polymer, a polyoxyethylene alkyl ether, a polyoxyethylene alkylaryl ether, a polyoxyethylene styrylaryl ether, a polyoxyethylene glycol alkyl ether, polyethylene glycol, a
polyoxyethylene fatty acid ester, a polyoxyethylene sorbitan fatty acid ester, a
polyoxyethylene glycerin fatty acid ester, a polyoxyethylene hydrogenated castor oil or a polyoxypropylene fatty acid ester; and a vegetable oil or mineral oil such as olive oil, kapok oil, castor oil, palm oil, camellia oil, coconut oil, sesame oil, corn oil, rice bran oil, peanut oil, cottonseed oil, soybean oil, rapeseed oil, linseed oil, tung oil or liquid paraffins. These additives may suitably be selected for use alone or in combination as a mixture of two or more of them, so long as the object of the present invention is met. Further, additives other than the above-mentioned may be suitably selected for use among those known in this field. For example, various additives commonly used, such as a filler, a thickener, an anti-settling agent, an anti-freezing agent, a dispersion stabilizer, a safener, an anti-mold agent, a bubble agent, a disintegrator and a binder, may be used. The mix ratio by weight of the active ingredient to such various additives may be from 0.001 :99.999 to 95:5, preferably from 0.005:99.995 to 90: 10.
As a method of applying the herbicidal composition of the present invention, a proper method can be selected for use among various methods depending upon various conditions such as the application site, the type of the formulation, and the type and the growth stage of the plants to be controlled, and for example, the following methods may be mentioned.
1. Compound A and compound B are mixed and formulated together, and the formulation is applied as it is.
2. Compound A and compound B are mixed and formulated together, and the formulation is diluted to a predetermined concentration with e.g. water, and as the case requires, a spreader (such as a surfactant, a vegetable oil or a mineral oil) is added for application.
3. Compound A and compound B are formulated separately, and the
formulations are applied as they are.
4. Compound A and compound B are formulated separately, and the
formulations are diluted to predetermined concentrations with e.g. water as the case requires, and as the case requires, a spreader (such as a surfactant, a vegetable oil or a mineral oil) is added for application.
5. Compound A and compound B are formulated separately, and the
formulations are mixed at the time of dilution to a predetermined concentration with e.g. water, and as the case requires, a spreader (such as a surfactant, a vegetable oil or a mineral oil) is added for application.
Preferred embodiments of the present invention will be described below, but the present invention is by no means restricted thereto. Hereinafter, the herbicidal composition containing compound A and compound B will be referred to as "the above herbicidal composition".
(1 ) The above herbicidal composition wherein compound A is a compound of the formula (I) wherein X is 1 ,3-dioxolan-2-yl, R1 is a chlorine atom, R2 is methylsulfonyl, Q is a hydrogen atom, and n is 2 (hereinafter referred to simply as compound A1).
(2) The above herbicidal composition wherein compound A is a sodium salt of the compound as defined in the above (1) (hereinafter referred to simply as compound A2).
(3) The above herbicidal composition wherein compound B is at least one phenoxy acetic acid type compound selected from the group consisting of (B1) 2,4-D, or its salt or ester, (B2) MCP, or its salt or ester, (B3) MCPB, or its salt or ester, and (B4) clomeprop.
(4) The above herbicidal composition wherein compound B is a plant hormone active (auxin active) disturbing herbicide selected from the phenoxy acetic acid type compounds as defined in the above (3) and (B59) quinclorac.
(5) The above herbicidal composition wherein compound B is at least one triazine type compound selected from the group consisting of (B5) simetryn and (B6) dimethametryn.
(6) The above herbicidal composition wherein compound B is a pyrimidine type compound such as (B7) bentazone.
(7) The above herbicidal composition wherein compound B is a photosynthesis- inhibiting herbicide selected from the triazine type compound as defined in the above (5) and the pyrimidine type compound as defined in the above (6).
(8) The above herbicidal composition wherein compound B is at least one heterocyclic compound selected from the group consisting of (B8) oxadiazon, (B9) oxadiargyl, (B10) pentoxazone, (B11 ) pyraclonil and (B12) carfentrazone-ethyl.
(9) The above herbicidal composition wherein compound B is a
protoporphyrinogen oxidase-inhibiting herbicide selected from heterocyclic compounds defined in the above (8).
(10) The above herbicidal composition wherein compound B is at least one pyrazole type compound selected from the group consisting of (B13) pyrazolynate, (B14) pyrazoxyfen and (B15) benzofenap.
(11) The above herbicidal composition wherein compound B is at least one triketone type compound selected from the group consisting of (B16) benzobicyclon, (B17) mesotrione, (B18) tefuryltrione, (B19) a compound of the above formula (II) and (B63) a compound of the above formula (IV).
(12) The above herbicidal composition wherein compound B is a 4-hydroxyphenyl pyruvic acid-inhibiting herbicide selected from the pyrazole type compound as defined in the above ( 0), the triketone type compound as defined in the above (11), (B20) the compound of the above formula (III) and (B61) clomazone.
(13) The above herbicidal composition wherein compound B is at least one aryloxyphenoxypropionic acid type compound selected from the group consisting of (B21) cyhalofop-butyl and (B22) metamifop.
(14) The above herbicidal composition wherein compound B is an acetyl CoA carboxylase-inhibiting herbicide selected from aryloxyphenoxypropionic acid-type compounds as defined in the above (13).
(15) The above herbicidal composition wherein compound B is at least one sulfonylurea type compound selected from the group consisting of (B23) bensulfuron- methyl, (B24) pyrazosulfuron-ethyl, (B25) imazosulfuron, (B26) azimsulfuron, (B27) cyclosulfamuron, (B28) ethoxysulfuron, (B29) halosulfuron-methyl, (B30)
flucetosulfuron, (B31) propyrisulfuron and (B32) metazosulfuron.
(16) The above herbicidal composition wherein compound B is a sulfonamide type compound such as (B33) penoxsulam.
(17) The above herbicidal composition wherein compound B is at least one pyrimidinylsalicylic acid-type compound selected from the group consisting of (B34) pyriminobac-methyl and (B35) bispyribac-sodium.
( 8) The above herbicidal composition wherein compound B is at least one sulfonanilide type compound selected from the group consisting of (B36) pyrimisulfan and (B37) triafamone.
(19) The above herbicidal composition wherein compound B is an acetolactate synthetase-inhibiting herbicide selected from the sulfonylurea type compound as defined in the above (15), the sulfonamide type compound as defined in the above (16), the pyrimidinylsalicylic acid type compound as defined in the above (17), the
sulfonanilide type compound as defined in the above (18), and (B38) pyriftalid.
(20) The above herbicidal composition wherein compound B is an organic phosphorus-type compound such as (B39) butamifos.
(21) The above herbicidal composition wherein compound B is at least one cumylamine type compound selected from the group consisting of (B40) daimuron,
(B41) cumyluron and (B42) bromobutide.
(22) The above herbicidal composition wherein compound B is a cell mitoses- inhibiting herbicide selected from the organic phosphorus type compound as defined in the above (20), the cumylamine type compound as defined in the above (21) and (B62) pendimethalin.
(23) The above herbicidal composition wherein compound B is at least one thiocarbamate type compound selected from the group consisting of (B43) molinate, (B44) esprocarb, (B45) pyributicarb and (B60) thiobencarb.
(24) The above herbicidal composition wherein compound B is at least one chloroacetamide type compound selected from the group consisting of (B46) butachlor, (B47) pretilachlor and (B48) thenylchlor.
(25) The above herbicidal composition wherein compound B is a lipid
biosynthesis-inhibiting herbicide selected from the thiocarbamate compound as defined in the above (23), the chloroacetamide compound as defined in the above (24), (B49) mefenacet, (B50) cafenstrole, (B51) indanofan, (B52) fentrazamide, (B53)
oxaziclomefone, (B54) etobenzanid, (B55) benfuresate, (B56) ipfencarbazone and (B57) fenoxasulfone.
(26) The above herbicidal composition wherein compound B is (B58)
quinoclamine.
(27) Each herbicidal composition comprising compound A1 and each of compound B as defined in any one of the above (3) to (26).
(28) Each herbicidal composition comprising compound A2 and each of compound B as defined in any one of the above (3) to (26).
(29) A method for controlling weeds or inhibiting their growth, which comprises applying a herbicidally effective amount of the herbicidal composition as defined in any one of the above (1) to (28) to the weeds or to a place where they grow.
(30) A method for controlling weeds or inhibiting their growth, which comprises applying a herbicidally effective amount of compound A1 and a herbicidally effective amount of compound B to the weeds or to a place where they grow.
(31 ) A method for controlling weeds or inhibiting their growth, which Comprises applying a herbicidally effective amount of compound A2 and a herbicidally effective amount of compound B to the weeds or to a place where they grow.
(32) A method for controlling weeds or inhibiting their growth, which comprises applying a herbicidally effective amount of compound A1 and a herbicidally effective amount of each compound B as defined in any one of the above (3) to (26) to the weeds or to a place where they grow.
(33) A method for controlling weeds or inhibiting their growth, which comprises applying a herbicidally effective amount of compound A2 and a herbicidally effective amount of each compound B as defined in any one of the above (3) to (26) to the weeds or to a place where they grow.
(34) The above herbicidal composition which contains compound A2 and (B12) carfentrazone-ethyl.
(35) The above herbicidal composition which contains compound A2 and (B30) flucetosulfuron.
EXAMPLES
Now, the present invention will be described in further detail with reference to Examples. However, it should be understood that the present invention is by no means restricted to such specific Examples. In Examples, compound A2 is as defined above and its chemical name is sodium 2-(3-(2-(1 ,3-dioxolan-2-yl)ethoxy)-2-chloro-4- (methylsulfonyl)benzoyl)-3-oxo-1-cyclohexenolate.
TEST EXAMPLE 1
Paddy soil was put into a 1/10,000 are pot to simulate a paddy field, and tubers of
Scirpus planiculmis Fr. Schm. were planted and left to stand under an irrigated condition with a water depth of 3.5 cm. When Scirpus planiculmis Fr. Schm. reached a predetermined size, compound A and compound B were, respectively, applied in predetermined amounts. After expiration of a predetermined period, the state of growth of Scirpus planiculmis Fr. Schm. was visually observed and investigated. As a measured value, the growth inhibition rate (%) evaluated in accordance with the following evaluation standard, and as a calculated value, the growth inhibition rate (%) calculated by the Colby's formula (WEED, vol.15, pages 20 to 22, 1967) are,
respectively, shown in Tables 1-1 to 1 -40.
Growth inhibition rate (%) = 0% (equivalent to the non-treated area) to 100%
(complete kill)
TABLE 1-1 (Scirpus planiculmis Fr. Schm.: initial stage of emergence, investigation date: 14th da after a lication of herbicide
Figure imgf000017_0002
TABLE 1-2 (Scirpus planiculmis Fr. Schm.: initial stage of emergence, investigation date: 14th day after application of herbicide)
Figure imgf000017_0001
TABLE 1-3 (Scirpus planiculmis Fr. Schm.: initial stage of emergence, investigation date: 14th da after a lication of herbicide
Figure imgf000018_0001
TABLE 1-4 (Scirpus planiculmis Fr. Schm.: initial stage of emergence, investigation date: 14th day after application of herbicide)
Growth inhibition rate (%)
Amount of active
Compound
ingredient (g/10a) Measured Calculated value value
21 55 -
Compound A2 10.5 55 -
5.25 48 -
45 0 -
Simetryn 22.5 8 -
11.25 5 -
21+45 85 55
21+22.5 68 59
21+11.25 80 57
10.5+45 71 55
Compound A2+
10.5+22.5
simetryn 76 59
10.5+11.25 70 57
5.25+45 63 48
5.25+22.5 63 52
5.25+11.25 84 51 TABLE 1-5 (Scirpus planiculmis Fr. Schm.: initial stage of emergence, investigation date: 11th da after a lication of herbicide
Figure imgf000019_0001
TABLE 1-6 (Scirpus planiculmis Fr. Schm.: initial stage of emergence, investigation date: 14th day after application of herbicide)
Growth inhibition rate (%)
Amount of active
Compound
ingredient (g/10a) Measured Calculated value value
21 55 -
Compound A2 10.5 55 -
5.25 48 -
2.5 78 -
Oxadiargyl
1.25 60 -
21+2.5 97 90
21+1.25 97 82
Compound A2+ 10.5+2.5 99 90 oxadiargyl 10.5+1.25 97 82
5.25+2.5 95 89
5.25+1.25 92 79 TABLE 1-7 (Scirpus planiculmis Fr. Schm.: initial stage of emergence, investigation
Growth inhibition rate (%)
Amount of active
Compound
ingredient (g/10a) Measured Calculated value value
21 56 -
Compound A2 10.5 55 -
5.25 43 -
22.5 86 -
Pentoxazone
11.25 60 -
21+22.5 98 94
21+11.25 95 82
Compound A2+ 10.5+22.5 98 94 pentoxazone 10.5+11.25 91 82
5.25+22.5 97 92
5.25+11.25 94 77
TABLE 1-8 (Scirpus planiculmis Fr. Schm. :5 cm, investiqation date: 10th day after application of herbicide)
Growth inhibition rate (%)
Amount of active
Compound
ingredient (g/10a) Measured Calculated value value
21 53 -
Compound A2
10.5 48 -
20 88 -
Pyraclonil
10 67 -
21+20 98 94
Compound A2+ 21+10 88 85 pyraclonil 10.5+20 98 94
10.5+10 93 83
TABLE 1-9 (Scirpus planiculmis Fr. Schm.: initial stage of emergence, investigation date: 7th da after a lication of herbicide
Figure imgf000021_0001
TABLE 1 -10 (Scirpus planiculmis Fr. Schm. :5 cm, investigation date: 10th day after application of herbicide)
Growth inhibition rate (%)
Amount of active
Compound
ingredient (g/10a) Measured Calculated value value
21 53 -
Compound A2 10.5 48
5.25 54 -
4.5 63 -
Carfentrazone-ethyl
2.25 60 -
21+4.5 96 83
21 +2.25 95 81
Compound A2+ 10.5+4.5 96 81 carfentrazone-ethyl 10.5+2.25 95 79
5.25+4.5 98 83
5.25+2.25 94 82
TABLE 1-11 (Scirpus planiculmis Fr. Schm. :5 cm, investigation date: 10th day after
Growth inhibition rate (%)
Amount of active
Compound
ingredient (g/10a) Measured Calculated value value
21 54 -
10.5 54 -
Compound A2 5.25 48 -
2.625 6 -
1.3125 0 -
Carfentrazone-ethyl 4.5 65 -
21 +4.5 98 84
10.5+4.5 99 84
Compound A2+
5.25+4.5 99 82 carfentrazone-ethyl
2.625+4.5 98 67
1.3125+4.5 79 65
TABLE 1-12 (Scirpus planiculmis Fr. Schm. :5 cm, investiqation date: 14th dav after application of herbicide)
Growth inhibition rate (%)
Amount of active
Compound
ingredient (g/10a) Measured Calculated value value
Compound A2 10.5 74 -
200 10 -
Pyrazoxyfen 100 0 -
50 0 -
10.5+200 93 77
Compound A2+
10.5+100 87 74 pyrazoxyfen
10.5+50 91 74
TABLE 1-13 (Scirpus planiculmis Fr. Schm. :5 cm, investigation date: 10th day after
Growth inhibition rate (%)
Amount of active
Compound
ingredient (g/10a) Measured Calculated value value
21 54 -
Compound A2 10.5 54 -
5.25 48 -
100 0 -
Benzofenap 50 0 -
25 0 -
21 +100 66 54
21+50 74 54
21 +25 60 54
10.5+100 64 54
Compound A2+
10.5+50 63
benzofenap 54
10.5+25 72 54
5.25+100 66 48
5.25+50 54 48
5.25+25 61 48
TABLE 1 -14 (Scirpus planiculmis Fr. Schm. :5 cm, investigation date: 14th day after application of herbicide)
Growth inhibition rate (%)
Amount of active
Compound
ingredient (g/10a) Measured Calculated value value
10.5 74 -
Compound A2
5.25 61 -
30 65 -
Tefuryltrione 15 60 -
7.5 43 -
10.5+30 95 91
Compound A2+
10.5+15 98
tefuryltrione 90
10.5+7.5 90 85 compound A+ 5.25+30 94 86 pyrazoxyfen 5.25+15 95 84
(Tank-Mix) 5.25+7.5 93 78 TABLE 1 -15 (Scirpus planiculmis Fr. Schm.: initial stage of emergence, investigation
Figure imgf000024_0001
TABLE 1-16 (Scirpus planiculmis Fr. Schm.: initial stage of emergence, investigation
Growth inhibition rate (%)
Amount of active
Compound
ingredient (g/10a) Measured Calculated value value
21 55 -
Compound A2 10.5 55 -
5.25 48 -
120 48 -
Cumyluron 60 23 -
30 28 -
21+120 96 77
21+60 83 65
21+30 79 68
10.5+120 99 77
Compound A2+
10.5+60 85 65 cumyluron
10.5+30 76 68
5.25+120 82 73
5.25+60 95 60
5.25+30 97 63
TABLE 1-17 (Scirpus planiculmis Fr. Schm.: initial stage of emergence, investigation date: 7th da after a lication of herbicide
Figure imgf000025_0001
TABLE 1 -18 (Scirpus planiculmis Fr. Schm.: initial stage of emergence, investigation date: 11th day after application of herbicide)
Growth inhibition rate (%)
Amount of active
Compound
ingredient (g/10a) Measured Calculated value value
21 50 -
Compound A2 10.5 47 -
5.25 25 -
150 5 -
Esprocarb 75 0 -
37.5 0 -
21+150 73 53
21+75 60 50
21+37.5 70 50
10.5+150 64 50
Compound A2+
10.5+75 66 47 esprocarb
10.5+37.5 68 47
5.25+150 57 29
5.25+75 63 25
5.25+37.5 59 25 TABLE 1-19 (Scirpus planiculmis Fr. Schm.: initial stage of emergence, investigation date: 14th da after a lication of herbicide
Figure imgf000026_0001
TABLE 1-20 (Scirpus planiculmis Fr. Schm.: initial stage of emergence, investigation date: 14th day after application of herbicide)
Growth inhibition rate (%)
Amount of active
Compound
ingredient (g/10a) Measured Calculated value value
21 56 -
Compound A2 10.5 55 -
5.25 43 -
160 84 -
Butachlor 80 63 -
40 60 -
21+160 99 93
21+80 99 84
21+40 99 82
10.5+160 99 93
Compound A2+
10.5+80 99
butachlor 83
10.5+40 95 82
5.25+160 99 91
5.25+80 99 79
5.25+40 96 77 TABLE 1-21 (Scirpus planiculmis Fr. Schm.: initial stage of emergence, investigation date: 13th da after a lication of herbicide
Figure imgf000027_0001
TABLE 1-22 (Scirpus planiculmis Fr. Schm.: initial stage of emergence, investigation date: 13th day after application of herbicide)
Growth inhibition rate (%)
Amount of active
Compound
ingredient (g/10a) Measured Calculated value value
21 58 -
Compound A2 10.5 55 -
5.25 54 -
15 71 -
Indanofan 7.5 78 -
3.75 40 -
21+15 98 88
21+7.5 96 91
21+3.75 96 75
10.5+15 99 87
Compound A2+
10.5+7.5 99 90 indanofan
10.5+3.75 98 73
5.25+15 98 87
5.25+7.5 99 90
5.25+3.75 93 72 TABLE 1-23 (Scirpus planiculmis Fr. Schm.: initial stage of emergence, investigation date: 13th da after a lication of herbicide
Figure imgf000028_0001
TABLE 1 -24 (Scirpus planiculmis Fr. Schm.: initial stage of emergence, investigation date: 13th day after application of herbicide)
Growth inhibition rate (%)
Amount of active
Compound
ingredient (g/10a) Measured Calculated value value
21 58 -
Compound A2 10.5 55 -
5.25 54 -
30 71 -
Ipfencarbazone 15 53 -
7.5 40 -
21 +30 98 88
21 +15 91 80
21+7.5 82 75
10.5+30 91 87
Compound A2+
10.5+15 97 79 ipfencarbazone
10.5+7.5 85 73
5.25+30 99 87
5.25+15 95 78
5.25+7.5 83 72 TABLE 1-25 (Scirpus planiculmis Fr. Schm.: initial stage of emergence, investigation date: 13th day after application of herbicide)
Figure imgf000029_0002
TABLE 1 -26 (Scirpus planiculmis Fr. Schm.: initial stage of emergence, investigation date: 14th day after application of herbicide) ^_
Figure imgf000029_0001
TABLE 1-27 (Scirpus planiculmis Fr. Schm. :5 cm, investigation date: 7th day after a lication of herbicide
Figure imgf000030_0001
TABLE 1-28 (Scirpus planiculmis Fr. Schm. :5 cm, investigation date: 7th day after application of herbicide)
Growth inhibition rate (%)
Amount of active
Compound
ingredient (g/10a) Measured Calculated value value
21 40 -
Compound A2 10.5 39 -
5.25 30 -
50 10 -
Compound of the above
25 13 - formula (III)
12.5 13 -
21+50 75 46
21 +25 65 48
21 +12-5 71 48
Compound A2+ 10.5+50 78 45 compound of the above 10.5+25 66 47 formula (III) 10.5+12.5 73 47
5.25+50 78 37
5.25+25 71 39
5.25+12.5 70 39 TABLE 1-29 (Scirpus planiculmis Fr. Schm: initial stage of emergence, investigation date: 7th day after a lication of herbicide
Figure imgf000031_0001
TABLE 1-30 (Scirpus planiculmis Fr. Schm: initial stage of emergence, investigation date: 7th day after application of herbicide)
Growth inhibition rate (%)
Amount of active
Compound
ingredient (g/10a) Measured Calculated value value
20 48 -
Compound A2 10 47 -
5 40 -
40 3 -
Quinclorac 20 0 -
10 0 -
20+40 63 50
20+20 68 48
20+10 60 48
10+40 65 49
Compound A2+
10+20 65 47
Quinclorac
10+10 61 47
5+40 51 42
5+20 51 40
5+10 62 40 TABLE 1-31 (Scirpus planiculmis Fr. Schm: initial stage of emergence, investigation
Figure imgf000032_0001
TABLE 1-32 ( Scirpus planiculmis Fr. Schm: initial stage of emergence, investigation
Growth inhibition rate (%)
Amount of active
Compound
ingredient (g/10a) Measured Calculated value value
20 50 -
Compound A2 10 49 -
5 40 -
200 54 -
Thiobencarb
100 5 -
20+200 88 77
20+100 80 53
Compound A2+ 10+200 87 77
Thiobencarb 10+100 70 52
5+200 92 72
5+100 73 43 TABLE 1 -33 ( Scirpus planiculmis Fr. Schm: 5cm, investigation date: 16th day after a lication of herbicide
Figure imgf000033_0001
TABLE 1 -34 ( Scirpus planiculmis Fr. Schm: initial stage of emergence, investigation date: 10th day after application of herbicide)
Growth inhibition rate (%)
Amount of active
Compound
ingredient (g/10a) Measured Calculated value value
20 50 -
Compound A2 10 49 -
5 40 -
60 3 -
30 0 -
Clomazone
15 0 -
7.5 0 -
20+60 58 52
20+30 60 50
20+15 66 50
20+7.5 63 50
10+60 60 51
Compound A2+ 10+30 63 49
Clomazone 10+15 78 49
10+7.5 61 49
5+60 55 42
5+30 55 40
5+15 60 40
5+7.5 56 40 TABLE 1-35 ( Scirpus planiculmis Fr. Schm: initial stage of emergence, investigation date: 14th da after a lication of herbicide
Figure imgf000034_0002
TABLE 1-36 ( Scirpus planiculmis Fr. Schm: 5cm, investigation date: 16th day after application of herbicide)
Figure imgf000034_0001
TABLE 1 -37 ( Scirpus planiculmis Fr. Schm: initial stage of emergence, investigation date: 10th da after a lication of herbicide
Figure imgf000035_0001
TABLE 1-38 ( Scirpus planiculmis Fr. Schm: 5cm, investigation date: 6th day after application of herbicide)
Growth inhibition rate (%)
Amount of active
Compound
ingredient (g/10a) Measured Calculated value value
20 45 -
10 44 -
Compound A2
5 24 -
2.5 10 -
4 58 -
Bispyribac-sodium
2 44 -
20+4 95 77
20+2 89 69
10+4 95 77
Compound A2+ 10+2 92 69
Bispyribac-sodium 5+4 93 68
5+2 81 57
2.5+4 94 62
2.5+2 85 50 TABLE 1-39 ( Scirpus planiculmis Fr. Schm: initial stage of emergence, investigation date: 10th da after a lication of herbicide
Figure imgf000036_0001
TABLE 1-40 ( Scirpus planiculmis Fr. Schm: 5cm, investigation date: 6th day after a lication of herbicide
Figure imgf000036_0002
TEST EXAMPLE 2
Paddy soil was put into a 1/10,000 are pot to simulate a paddy field, and seeds of barnyardgrass (Echinochloa oryzicola vasing.) were sown, and left to stand under an irrigated condition with a water depth of 3.5 cm. When Echinochloa oryzicola vasing. reached a predetermined size, compound A and compound B were, respectively, applied in predetermined amounts. After expiration of a predetermined period, the state of growth of Echinochloa oryzicola vasing. was visually observed and investigated. The growth inhibition rates (%) evaluated in the same manner as in Test Example 1 are shown in Tables 2-1 to 2-9.
TABLE 2-1 (Echinochloa oryzicola vasing.: 3-leaf stage, investigation date: 14th day
Figure imgf000037_0001
TABLE 2-3 (Echinochloa oryzicola vasing.: 3-leaf stage, investigation date: 20th day after application of herbicide)
Growth inhibition rate (%)
Amount of active
Compound
ingredient (g/10a) Measured Calculated value value
Compound A2 2.625 0 -
1 87 -
Pyrimisulfan 0.5 65 -
0.25 50 -
2.625+1 92 87
Compound A2+
2.625+0.5 73 65 pyrimisulfan
2.625+0.25 55 50 TABLE 2-4 (Echinochloa orvzicola vasing.: 3-leaf stage, investigation date: 20th day after a lication of herbicide
Figure imgf000038_0001
TABLE 2-5 (Echinochloa orvzicola vasing.: 3-leaf stage, investigation date: 20th day after application of herbicide)
Growth inhibition rate (%)
Amount of active
Compound ingredient (g/10a) Measured Calculated value value
Compound A2 5.25 23 -
9 53 -
Mesotrione 4.5 33 -
2.25 3 -
5.25+9 81 64
Compound A2+
5.25+4.5 58 48 mesotrione
5.25+2.25 40 25
TABLE 2-6 (Echinochloa oryzicola vasing.: 3-leaf stage, investigation date: 11th day after a lication of herbicide
Figure imgf000039_0001
TABLE 2-7 (Echinochloa oryzicola vasing.: 3-leaf stage, investigation date: 11th day after application of herbicide) -
Amount of active Growth inhibition rate (%)
Compound ingredient (g/10a) Measured Calculated
(g/10a) value value
20 40 -
Compound A2 10 17 -
5 10 -
20 62 -
Compound of the above 10 48 - formula (IV) 5 15 -
2.5 10 -
20+20 82 77
20+10 72 69
20+5 72 49
20+2.5 68 46
10+20 82 69
Compound A2+ 10+10 72 57
Compound of the above
formula (IV) 10+5 67 30
10+2.5 57 25
5+20 79 66
5+10 62 53
5+5 43 24
5+2.5 37 19 TABLE 2-8 (Echinochloa orvzicola vasinq.: 3-leaf stage, investigation date:* 15th day" after a lication of herbicide
Figure imgf000040_0001
TABLE 2-9 (Echinochloa orvzicola vasing.: 3-leaf stage, investigation date: 15th day after a lication of herbicide
Figure imgf000040_0002
TEST EXAMPLE 3
Paddy soil was put into a 1/10,000 are pot to simulate a paddy field, and tubers of arrow-head (Sagittaria trifolia L.) (sulfonyl urea resistant) were planted and left to stand under an irrigated condition with a water depth of 3.5 cm. When arrow-head (Sagittaria trifolia L.) reached a predetermined size, compound A and compound B were, respectively, applied in predetermined amounts. After expiration of a predetermined period, the state of growth of arrow-head (Sagittaria trifolia L.) was visually observed and investigated. The growth inhibition rates (%) evaluated in the same manner as in the above Test Example 1 are shown in Tables 3-1 to 3-3. TABLE 3-1 (arrow-head (Saqittaria trifolia L.):initial stage of emergence, investigation date: 28th da after a lication of herbicide
Figure imgf000041_0001
TABLE 3-2 (arrow-head (Saqittaria trifolia L.):initial stage of emergence, investigation date: 28th day after application of herbicide)
Growth inhibition rate (%)
Amount of active
Compound
ingredient (g/ 0a) Measured Calculated value value
21 81 -
Compound A2
10.5 57 -
9 3 -
Halosulfuron-methyl 4.5 0 -
2.25 0 -
21+9 90 82
Compound A2+
21+4.5 86 81 halosulfuron-methyl
21+2.25 92 81 compound A+ 10.5+9 85 58 pyrazoxyfen 10.5+4.5 91 57
(Tank-Mix) 10.5+2.25 86 57 TABLE 3-3 (arrow-head (Sagittaria trifolia L.):initial stage of emergence, investigation date: 42nd da after a lication of herbicide
Figure imgf000042_0001
TEST EXAMPLE 4
Paddy soil was put into a 1/10,000 are pot to simulate a paddy field, and tubers of arrow-head (Sagittaria trifolia L.) (sulfonyl urea sensitive) were planted and left to stand under an irrigated condition with a water depth of 3.5 cm. When arrow-head (Sagittaria trifolia L.) reached a predetermined size, compound A and compound B were, respectively, applied in predetermined amounts. After expiration of a predetermined period, the state of growth of arrow-head (Sagittaria trifolia L.) was visually observed and investigated. The growth inhibition rates (%) evaluated in the same manner as in the above Test Example 1 are shown in Tables 4-1 to 4-3.
TABLE 4-1 (arrow-head (Sagittaria trifolia L.): initial stage of emergence, investigation date: 53rd day after application of herbicide)
Growth inhibition rate (%)
Amount of active
Compound
ingredient (g/10a) Measured Calculated value value
5 0 -
Compound A2 2.5 0 -
1.25 0 -
Imazosulfuron 0.5 63 -
5+0.5 90 63
Compound A2+
2.5+0.5 82 63
imazosulfuron
1.25+0.5 87 63 TABLE 4-2 (arrow-head (Saqittaria trifolia L.): pre-emergence, investigation date: 39th da after a lication of herbicide
Figure imgf000043_0001
TABLE 4-3 (arrow-head (Saqittaria trifolia L.): pre-emergence, investigation date: 39th da after a lication of herbicide
Figure imgf000043_0002
TEST EXAMPLE 5
Paddy soil was put into a 1/10,000 are pot to simulate a paddy field, and seeds of
Japanese bulrush (Scirpus iuncoides) (sulfonylurea sensitive and resistant present as mixed) were sown, and left to stand under an irrigated condition with a water depth of 3.5 cm. When Japanese bulrush (Scirpus iuncoides) reached a predetermined size, compound A and compound B were, respectively, applied in predetermined amounts. On the day after the application, in order to simulate overflowing by raining, paddy water was once removed to a water depth of about 1 cm and then increased again to a water depth of 3.5 cm. After expiration of a predetermined period, the state of growth of Japanese bulrush (Scirpus juncoides) was visually observed and investigated. The growth inhibition rates (%) evaluated in the same manner as in the above Test Example 1 are shown in Tables 5-1 to 5-3.
TABLE 5-1 (Japanese bulrush (Scirpus juncoides: 2-leaf stage, investigation date: 17th da after a lication of herbicide
Figure imgf000044_0001
TABLE 5-2 (Japanese bulrush (Scirpus juncoides: 2-leaf stage, investigation date: 17th day after application of herbicide)
Amount of active Growth inhibition rate (%)
Compound ingredient (g/10a) Measured Calculated
(g/10a) value value
10 50 -
Compound A2
5 45 -
1 23 -
Pyrazosulfuron-ethyl 0.5 20 -
0.25 23 -
10+1 75 62
10+0.5 68 60
Compound A2+ 10+0.25 80 62
Pyrazosulfuron-ethyl 5+1 65 58
5+0.5 73 56
5+0.25 73 58 TABLE 5-3 (Japanese bulrush (Scirpus iuncoides: 2-leaf stage, investigation date: 17th da after a lication of herbicide
Figure imgf000045_0001
INDUSTRIAL APPLICABILITY
According to the present invention, it is possible to provide a herbicidal
composition having a broad herbicidal spectrum, having high activity and having a long- lasting effect.
The entire disclosure of Japanese Patent Application No. 2012-116274 filed on May 22, 2012 including specification, claims and abstract is incorporated herein by reference in its entirety.

Claims

1. A herbicidal composition comprising (A) a compound represented by the formula
Figure imgf000046_0001
wherein X is a 5- or 6-membered saturated heterocyclic group containing one or two hetero atoms of at least one type selected from the group consisting of an oxygen atom and a sulfur atom (said heterocyclic group may be substituted by alkyl), or
dialkoxymethyl, R1 is halogen, R2 is alkyl, haloalkyl, alkoxy, haloalkoxy, alkylthio, haloalkylthio, alkylsulfinyl, haloalkylsulfinyl, alkylsulfonyl, haloalkylsulfonyl,
dialkylaminosulfonyl, di(haloalkyl)aminosulfonyl, nitro or cyano, Q is a hydrogen atom or benzoyl, and n is 1 or 2, and (B) at least one compound selected from the group consisting of (B1) 2,4-D, or its salt or ester, (B2) MCP, or its salt or ester, (B3) MCPB, or its salt or ester, (B4) clomeprop, (B5) simetryn, (B6) dimethametryn, (B7) bentazone, (B8) oxadiazon, (B9) oxadiargyl, (B10) pentoxazone, (B11) pyraclonil, (B12)
carfentrazone-ethyl, (B13) pyrazolynate, (B14) pyrazoxyfen, (B15) benzofenap, (B16) benzobicyclon, (B17) mesotrione, (B18) tefuryltrione, (B19) a compound represented by the formula (II):
he formula (III):
Figure imgf000046_0002
(B21) cyhalofop-butyl, (B22) metamifop, (B23) bensulfuron-methyl, (B24)
pyrazosulfuron-ethyl, (B25) imazosulfuron, (B26) azimsulfuron, (B27) cyclosulfamuron, (B28) ethoxysulfuron, (B29) halosulfuron-methyl, (B30) flucetosulfuron, (B31)
propyrisulfuron, (B32) metazosulfuron, (B33) penoxsulam, (B34) pyriminobac-methyl, (B35) bispyribac-sodium, (B36) pyrimisulfan, (B37) triafamone, (B38) pyriftalid, (B39) butamifos, (B40) daimuron, (B41) cumyluron, (B42) bromobutide, (B43) molinate, (B44) esprocarb, (B45) pyributicarb, (B46) butachlor, (B47) pretilachlor, (B48) thenylchlor, (B49) mefenacet, (B50) cafenstrole, (B51 ) indanofan, (B52) fentrazamide, (B53) oxaziclomefone, (B54) etobenzanid, (B55) benfuresate, (B56) ipfencarbazone, (B57) fenoxasulfone, (B58) quinoclamine, (B59) quinclorac, (B60) thiobencarb, (61)
clomazone, (B62) pendimethalin and (B63) a compound represented by the formula (IV):
2. The herbicidal composition according to Claim 1 , wherein the compound of (A) and the compound of (B) are the following compounds, respectively:
(A) a compound of the formula (I) wherein X is 1 ,3-dioxolan-2-yl, R1 is a chlorine atom, R2 is a methylsulfonyl, Q is a hydrogen atom, and n is 2, or its sodium salt,
(B) at least one compound classified into a protoporphyrinogen oxidase-inhibiting herbicide selected from the group consisting of (B8) oxadiazon, (B9) oxadiargyl, (B10) pentoxazone, (B11) pyraclonil and (B12) carfentrazone-ethyl.
3. The herbicidal composition according to Claim 1 , wherein the compound of (A) and the compound of (B) are the following compounds, respectively:
(A) a compound of the formula (I) wherein X is 1 ,3-dioxolan-2-yl, R1 is a chlorine atom, R2 is a methylsulfonyl, Q is a hydrogen atom, and n is 2, or its sodium salt,
(B) at least one compound classified into a 4-hydroxyphenyl pyruvic acid-inhibiting herbicide selected from the group consisting of (B13) pyrazolynate, (B14) pyrazoxyfen, (B15) benzofenap, (B16) benzobicyclon, (B17) mesotrione, (B18) tefuryltrione, (B19) a compound of the above formula (II), (B20) a compound of the above formula (III), (B61) clomazone and (B63) a compound of the above formula (IV).
4. The herbicidal composition according to Claim 1 , wherein the compound of (A) and the compound of (B) are the following compounds, respectively:
(A) a compound of the formula (I) wherein X is 1 ,3-dioxolan-2-yl, R1 is a chlorine atom, R2 is a methylsulfonyl, Q is a hydrogen atom, and n is 2, or its sodium salt,
(B) at least one compound classified into an acetyl CoA carboxylase-inhibiting herbicide selected from the group consisting of (B21 ) cyhalofop-butyl and (B22) metamifop.
5. The herbicidal composition according to Claim 1 , wherein the compound of (A) and the compound of (B) are the following compounds, respectively:
(A) a compound of the formula (I) wherein X is 1 ,3-dioxolan-2-yl, R1 is a chlorine atom, R2 is a methylsulfonyl, Q is a hydrogen atom, and n is 2, or its sodium salt,
(B) at least one compound classified into an acetolactate synthetase-inhibiting herbicide selected from the group consisting of (B23) bensulfuron-methyl, (B24) pyrazosulfuron-ethyl, (B25) imazosulfuron, (B26) azimsulfuron, (B27) cyclosulfamuron, (B28) ethoxysulfuron, (B29) halosulfuron-methyl, (B30) flucetosulfuron, (B31 ) propyrisulfuron, (B32) metazosulfuron, (B33) penoxsulam, (B34) pyriminobac-methyl, (B35) bispyribac-sodium, (B36) pyrimisulfan, (B37) triafamone and (B38) pyriftalid.
6. The herbicidal composition according to Claim 1 , wherein the compound of (A) and the compound of (B) are the following compounds, respectively:
(A) a compound of the formula (I) wherein X is 1 ,3-dioxolan-2-yl, R1 is a chlorine atom, R2 is a methylsulfonyl, Q is a hydrogen atom, and n is 2, or its sodium salt,
(B) at least one compound classified into a lipid biosynthesis-inhibiting herbicide selected from the group consisting of (B43) molinate, (B44) esprocarb, (B45)
pyributicarb, (B60) thiobencarb, (B46) butachlor, (B47) pretilachlor, (B48) thenylchlor, (B49) mefenacet, (B50) cafenstrole, (B51) indanofan, (B52) fentrazamide, (B53) oxaziclomefone, (B54) etobenzanid, (B55) benfuresate, (B56) ipfencarbazone and (B57) fenoxasulfone.
7. The herbicidal composition according to any one of Claims 1 to 6, wherein the mixing ratio of (A) and (B) is such that (B) is from 0.0005 to 500 parts by weight to 1 part by weight of (A).
8. A method for controlling weeds or inhibiting their growth, which comprises applying a herbicidally effective amount of (A) a compound represented by the formula (I) or its salt:
Figure imgf000048_0001
wherein X is a 5- or 6-membered saturated heterocyclic group containing one or two hetero atoms of at least one type selected from the group consisting of an oxygen atom and a sulfur atom (said heterocyclic group may be substituted by alkyl), or
dialkoxymethyl, R1 is halogen, R2 is alkyl, haloalkyl, alkoxy, haloalkoxy, alkylthio, haloalkylthio, alkylsulfinyl, haloalkylsulfinyl, alkylsulfonyl, haloalkylsulfonyl,
diaikylaminosulfonyl, di(haloalkyl)aminosulfonyl, nitro or cyano, Q is a hydrogen atom or benzoyl, and n is 1 or 2, and a herbicidally effective amount of (B) at least one compound selected from the group consisting of (B1 ) 2,4-D, or its salt or ester, (B2) MCP, or its salt or ester, (B3) MCPB, or its salt or ester, (B4) clomeprop, (B5) simetryn, (B6) dimethametryn, (B7) bentazone, (B8) oxadiazon,
(B9) oxadiargyl,
(B10)
pentoxazone,
(B11 ) pyraclonil,
(B12) carfentrazone-ethyl,
(B13) pyrazolynate,
(B14) pyrazoxyfen,
(B15) benzofenap,
(B16) benzobicyclon,
(B17) mesotrione,
(B18) tefuryltrione,
(B19) a compound represented by the formula (II):
Figure imgf000048_0002
(B20) a compound represented by the formula (III):
Figure imgf000048_0003
(B21 ) cyhalof op-butyl, (B22) metamifop, (B23) bensulfuron-methyl, (B24)
pyrazosulfuron-ethyl, (B25) imazosulfuron, (B26) azimsulfuron, (B27) cyclosulfamuron, (B28) ethoxysulfuron, (B29) halosulfuron-methyl, (B30) flucetosulfuron, (B31)
propyrisulfuron, (B32) metazosulfuron, (B33) penoxsulam, (B34) pyriminobac-methyl, (B35) bispyribac-sodium, (B36) pyrimisulfan, (B37) triafamone, (B38) pyriftalid, (B39) butamifos, (B40) daimuron, (B41) cumyluron, (B42) bromobutide, (B43) molinate, (B44) esprocarb, (B45) pyributicarb, (B46) butachlor, (B47) pretilachlor, (B48) thenylchlor, (B49) mefenacet, (B50) cafenstrole, (B51) indanofan, (B52) fentrazamide, (B53) oxaziclomefone, (B54) etobenzanid, (B55) benfuresate, (B56) ipfencarbazone, (B57) fenoxasulfone, (B58) quinoclamine, (B59) quinclorac, (B60) thiobencarb, (61) clomazone, (B62) pendimethalin and (B63) a compound represented by the formula (IV):
Figure imgf000049_0001
to the weeds or to a place where they grow.
9. The method according to Claim 8, wherein the compound of (A) and the compound of (B) are the following compounds, respectively:
(A) a compound of the formula (I) wherein X is 1 ,3-dioxolan-2-yl, R1 is a chlorine atom, R2 is a methylsulfonyl, Q is a hydrogen atom, and n is 2, or its sodium salt,
(B) at least one compound classified into a protoporphyrinogen oxidase-inhibiting herbicide selected from the group consisting of (B8) oxadiazon, (B9) oxadiargyl, (B10) pentoxazone, (B11) pyraclonil and (B12) carfentrazone-ethyl.
10. The method according to Claim 8, wherein the compound of (A) and the compound of (B) are the following compounds, respectively:
(A) a compound of the formula (I) wherein X is 1 ,3-dioxolan-2-yl, R1 is a chlorine atom, R2 is a methylsulfonyl, Q is a hydrogen atom, and n is 2, or its sodium salt,
(B) at least one compound classified into a 4-hydroxyphenyl pyruvic acid-inhibiting herbicide selected from the group consisting of (B13) pyrazolynate, (B14) pyrazoxyfen, (B15) benzofenap, (B16) benzobicyclon, (B17) mesotrione, (B18) tefuryltrione, (B19) a compound of the above formula (II), (B20) a compound of the above formula (III), (B61) clomazone and (B63) a compound of the above formula (IV).
11. The method according to Claim 8, wherein the compound of (A) and the compound of (B) are the following compounds, respectively:
(A) a compound of the formula (I) wherein X is 1 ,3-dioxolan-2-yl, R1 is a chlorine atom, R2 is a methylsulfonyl, Q is a hydrogen atom, and n is 2, or its sodium salt,
(B) at least one compound classified into an acetyl CoA carboxylase-inhibiting herbicide selected from the group consisting of (B21) cyhalofop-butyl and (B22) metamifop.
12. The method according to Claim 8, wherein the compound of (A) and the compound of (B) are the following compounds, respectively:
(A) a compound of the formula (I) wherein X is 1 ,3-dioxolan-2-yl, R is a chlorine atom, R2 is a methylsulfonyl, Q is a hydrogen atom, and n is 2, or its sodium salt,
(B) at least one compound classified into an acetolactate synthetase-inhibiting herbicide selected from the group consisting of (B23) bensulfuron-methyl, (B24) pyrazosulfuron-ethyl, (B25) imazosulfuron, (B26) azimsulfuron, (B27) cyclosulfamuron, (B28) ethoxysulfuron, (B29) halosulfuron-methyl, (B30) flucetosulfuron, (B31) propyrisulfuron, (B32) metazosulfuron, (B33) penoxsulam, (B34) pyriminobac-methyl, (B35) bispyribac-sodium, (B36) pyrimisulfan, (B37) triafamone and (B38) pyriftalid 13. The method according to Claim 8, wherein the compound of (A) and the compound of (B) are the following compounds, respectively:
(A) a compound of the formula (I) wherein X is 1 ,3-dioxolan-2-yl, R1 is a chlorine atom, R2 is a methylsulfonyl, Q is a hydrogen atom, and n is 2, or its sodium salt, (B) at least one compound classified into a lipid biosynthesis-inhibiting herbicide selected from the group consisting of (B43) molinate, (B44) esprocarb, (B45) pyributicarb, (B60) thiobencarb, (B46) butachlor, (B47) pretilachlor, (B48) thenylchlor, (B49) mefenacet, (B50) cafenstrole, (B51) indanofan, (B52) fentrazamide, (B53) oxaziclomefone, (B54) etobenzanid, (B55) benfuresate, (B56) ipfencarbazone and (B57) fenoxasulfone.
14. The method according to any one of Claims 8 to 13, wherein (A) is applied in an amount of from 0.1 to 10 g/are, and (B) is applied in an amount of from 0.005 to 50 g/are.
PCT/JP2013/064559 2012-05-22 2013-05-21 Herbicidal composition Ceased WO2013176282A1 (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
KR20147035402A KR20150020573A (en) 2012-05-22 2013-05-21 Herbicidal composition

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
JP2012-116274 2012-05-22
JP2012116274 2012-05-22

Publications (1)

Publication Number Publication Date
WO2013176282A1 true WO2013176282A1 (en) 2013-11-28

Family

ID=49623959

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/JP2013/064559 Ceased WO2013176282A1 (en) 2012-05-22 2013-05-21 Herbicidal composition

Country Status (4)

Country Link
JP (2) JP6138579B2 (en)
KR (1) KR20150020573A (en)
TW (1) TWI574622B (en)
WO (1) WO2013176282A1 (en)

Cited By (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN107371452A (en) * 2017-07-21 2017-11-24 中国科学院东北地理与农业生态研究所 A kind of flat stalk cyperus iria L. rhizoma scirpi bulb storage method for improving emergence rate and shortening seedling-growing time
KR20180078254A (en) * 2015-10-30 2018-07-09 구미아이 가가쿠 고교 가부시키가이샤 Rice Seed Treatment
CN108633902A (en) * 2018-04-14 2018-10-12 靖凡 A kind of synergistic composition containing halosulfuronmethyl and its weeding application
WO2022084334A1 (en) 2020-10-19 2022-04-28 Syngenta Crop Protection Ag Mixtures of pyrimidines as herbicidal compositions
WO2022084335A1 (en) 2020-10-19 2022-04-28 Syngenta Crop Protection Ag Mixtures of pyridazines as herbicidal compositions
CN114586798A (en) * 2021-04-02 2022-06-07 江苏富田农化有限公司 Weed removal composition and herbicide thereof
WO2023208866A1 (en) 2022-04-25 2023-11-02 Syngenta Crop Protection Ag Herbicidal compositions

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
KR102224747B1 (en) 2020-08-24 2021-03-05 장영호 Tin coating method of iron base material using pack cementation

Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO1998034480A1 (en) * 1997-02-07 1998-08-13 Novartis Ag Herbicidal agent
US20050192182A1 (en) * 2001-08-30 2005-09-01 Dieter Feucht Herbicidal mixtures based on substituted aryl ketones
JP2006016389A (en) * 2004-06-03 2006-01-19 Ishihara Sangyo Kaisha Ltd Triketone compounds, methods for producing them, and herbicides containing them

Family Cites Families (14)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPH02726A (en) * 1987-11-28 1990-01-05 Nippon Soda Co Ltd Cyclohexenone derivative, production thereof and herbicide
DE4216880A1 (en) * 1992-05-21 1993-11-25 Hoechst Ag Synergistic herbicidal compsns. - contg. 2-benzoyl-1,3-cyclohexane-di:one deriv. and at least one other herbicide
JPH06271562A (en) * 1993-03-23 1994-09-27 Hokko Chem Ind Co Ltd Cyclohexanedione derivative and herbicide
JPH06321932A (en) * 1993-05-07 1994-11-22 Hokko Chem Ind Co Ltd Cyclohexanedione derivative and herbicide
JPH07206808A (en) * 1994-01-17 1995-08-08 Hokko Chem Ind Co Ltd Cyclohexanedione derivative and herbicide
JPH1059929A (en) * 1996-05-30 1998-03-03 Hokko Chem Ind Co Ltd Cyclohexanedione derivative and herbicidal composition
JP2001122848A (en) * 1999-08-19 2001-05-08 Ishihara Sangyo Kaisha Ltd Triketone-based compound, its production and herbicide containing the same
JP2002145705A (en) * 2000-08-31 2002-05-22 Nippon Nohyaku Co Ltd Paddy field herbicide composition and control method
WO2003028450A2 (en) * 2001-09-27 2003-04-10 Syngenta Participations Ag Herbicidal composition
KR20120123735A (en) * 2004-06-03 2012-11-09 이시하라 산교 가부시끼가이샤 Triketone compounds, method for producing those and herbicide containing those
DE102004029307A1 (en) * 2004-06-17 2005-12-29 Bayer Cropscience Gmbh Substituted benzoylcyclohexanediones as herbicides
DE102007028019A1 (en) * 2007-06-19 2008-12-24 Bayer Cropscience Ag Synergistic crop tolerated combinations containing herbicides from the group of benzoylcyclohexanediones for use in rice crops
EP2526770A1 (en) * 2009-05-27 2012-11-28 Bayer Cropscience AG Synergistic herbicide combinations containing tembotrione
JP2011190198A (en) * 2010-03-12 2011-09-29 Mitsui Chemicals Agro Inc Mixed herbicidal composition

Patent Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO1998034480A1 (en) * 1997-02-07 1998-08-13 Novartis Ag Herbicidal agent
US20050192182A1 (en) * 2001-08-30 2005-09-01 Dieter Feucht Herbicidal mixtures based on substituted aryl ketones
JP2006016389A (en) * 2004-06-03 2006-01-19 Ishihara Sangyo Kaisha Ltd Triketone compounds, methods for producing them, and herbicides containing them

Cited By (10)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
KR20180078254A (en) * 2015-10-30 2018-07-09 구미아이 가가쿠 고교 가부시키가이샤 Rice Seed Treatment
US20180343787A1 (en) * 2015-10-30 2018-12-06 Kumiai Chemical Industry Co., Ltd. Rice seed treatment agent
US10506759B2 (en) * 2015-10-30 2019-12-17 Kumiai Chemical Industry Co., Ltd. Rice seed treatment agent
KR102391897B1 (en) 2015-10-30 2022-04-27 구미아이 가가쿠 고교 가부시키가이샤 paddy rice seed treatment
CN107371452A (en) * 2017-07-21 2017-11-24 中国科学院东北地理与农业生态研究所 A kind of flat stalk cyperus iria L. rhizoma scirpi bulb storage method for improving emergence rate and shortening seedling-growing time
CN108633902A (en) * 2018-04-14 2018-10-12 靖凡 A kind of synergistic composition containing halosulfuronmethyl and its weeding application
WO2022084334A1 (en) 2020-10-19 2022-04-28 Syngenta Crop Protection Ag Mixtures of pyrimidines as herbicidal compositions
WO2022084335A1 (en) 2020-10-19 2022-04-28 Syngenta Crop Protection Ag Mixtures of pyridazines as herbicidal compositions
CN114586798A (en) * 2021-04-02 2022-06-07 江苏富田农化有限公司 Weed removal composition and herbicide thereof
WO2023208866A1 (en) 2022-04-25 2023-11-02 Syngenta Crop Protection Ag Herbicidal compositions

Also Published As

Publication number Publication date
JP2014001202A (en) 2014-01-09
JP2017101076A (en) 2017-06-08
JP6138579B2 (en) 2017-05-31
KR20150020573A (en) 2015-02-26
TW201406288A (en) 2014-02-16
JP6337413B2 (en) 2018-06-06
TWI574622B (en) 2017-03-21

Similar Documents

Publication Publication Date Title
CA2746042C (en) Herbicidal compositions containing benzoylpyrazole compounds
KR102025681B1 (en) Herbicidal composition having improved herbicidal activity
CA2914339C (en) Herbicidal composition having improved plant safety
JP6337413B2 (en) Herbicidal composition
AU2012274296B2 (en) Herbicidal composition
JP5368714B2 (en) Herbicidal composition
US8609591B2 (en) Herbicidal composition
CA2818845A1 (en) Herbicidal composition comprising flazasulfuron and nicosulfuron
CA2926330C (en) Herbicide composition
NZ619162B2 (en) Herbicidal composition comprising flazasulfuron and pyroxasulfone
NZ714954B2 (en) Herbicidal composition having improved plant safety

Legal Events

Date Code Title Description
121 Ep: the epo has been informed by wipo that ep was designated in this application

Ref document number: 13794433

Country of ref document: EP

Kind code of ref document: A1

NENP Non-entry into the national phase

Ref country code: DE

ENP Entry into the national phase

Ref document number: 20147035402

Country of ref document: KR

Kind code of ref document: A

NENP Non-entry into the national phase

Ref country code: JP

122 Ep: pct application non-entry in european phase

Ref document number: 13794433

Country of ref document: EP

Kind code of ref document: A1