Attorney Dec. No. 10830~89US
`Ref. No. 578705
`
`DESCRIPTION
`
`lwACETYLMBMPHENYL UREA COMPOUND, AND USE THEREQF
`
`5
`
`TECHNICAL FIELD
`
`{0001}
`
`Thie application claims priority to and the benefit of
`
`Japanese Patent Application No, 2016~165424 filed August 26,
`
`2016,
`
`the entire contents of which are incorporated herein
`
`10
`
`by ieferenc..
`
`The preeent
`
`invention is
`
`related Le
`
`a
`
`5)) (1 (D m l~<‘. L..J
`
`lm
`
`E
`
`E
`
`m
`
`phenyl urea compound and a use of the same.
`
`BACKGROUND ART
`
`15
`
`[0002}
`
`Patent document
`
`1 describes N»[4wchlorcn2-fluor0*5~{;m
`
`(ethoxycarbonyl)methoxy—B—pyridylexy}phenyl]acetamide.
`
`U)
`CITATION LI T
`
`20
`
`PATENT DOC MENT
`
`[“003]
`
`Patent Document 1: E? patent No. 1122244 B2
`
`SUMMARY OF THE INVENTION
`
`h) (I:
`
`(PROBLEMS TO BE SGLVED BY INVENTION)
`
`
`Ref. No. 578705
`
`DESCRIPTION
`
`lwACETYLMBMPHENYL UREA COMPOUND, AND USE THEREQF
`
`5
`
`TECHNICAL FIELD
`
`{0001}
`
`Thie application claims priority to and the benefit of
`
`Japanese Patent Application No, 2016~165424 filed August 26,
`
`2016,
`
`the entire contents of which are incorporated herein
`
`10
`
`by ieferenc..
`
`The preeent
`
`invention is
`
`related Le
`
`a
`
`5)) (1 (D m l~<‘. L..J
`
`lm
`
`E
`
`E
`
`m
`
`phenyl urea compound and a use of the same.
`
`BACKGROUND ART
`
`15
`
`[0002}
`
`Patent document
`
`1 describes N»[4wchlorcn2-fluor0*5~{;m
`
`(ethoxycarbonyl)methoxy—B—pyridylexy}phenyl]acetamide.
`
`U)
`CITATION LI T
`
`20
`
`PATENT DOC MENT
`
`[“003]
`
`Patent Document 1: E? patent No. 1122244 B2
`
`SUMMARY OF THE INVENTION
`
`h) (I:
`
`(PROBLEMS TO BE SGLVED BY INVENTION)
`
`
`
`[0004]
`
`An object of
`
`the preeent
`
`invention is to provide a
`
`comgound having an excellent efiicacy for controlling weedso
`
`5
`
`(MEANS TO SOLVE PROBLEMS)
`
`[0005}
`
`The present
`
`inventor has intensively studied to solve
`
`the problems, and as a tesult, he found out that a compound
`
`J.
`r5 g...‘ e 5 -'1
`represented by the following formula (1) he“ an exc.flf
`
`10
`
`cont:ol efficacy on weeds.
`
`That is,
`
`the present invention includes the followings.
`
`‘___\
`
`1...;
`
`,...,
`
`A compound reYresented by tormuia (l):
`
`(hereinafter,
`
`referred to as
`
`"Compound of
`
`the present
`
`lb
`
`invention" or "Present compound“)
`
`0
`
`[2]
`
`A herbicide comprising the compound described in [l]
`
`(hereinafter,
`
`referred to as
`
`"Eerbicide 0'
`
`the present
`
`invention" or "Present herbicide").
`
`[3]
`
`A method
`
`for
`
`controlling a weed which
`
`comptises
`
`20
`
`applying the compound described in [l]
`
`to the weed or soil
`
`
`
`.\LA]
`
`where the weed is growing.
`
`e] Use of the compound described in {l} to control a weed.
`
`{EFFECT OF INVENTION
`
`m
`
`3
`
`.0 ¢
`
`6]
`
`The compound of the present
`
`invention has an excellent
`
`efficacy for centroi.ling weeds,
`
`and is thus useiui as an
`
`active ingredient fer a herbicide.
`
`§__J CD
`
`MODE FOR CARRYING OUT THE I VENTIGN
`
`C c i h)
`
`r...l
`
`The herbicide of
`
`the present
`
`iniention compri es
`
`a
`
`compound of
`
`the present
`
`inventi.on and an inert carrier,
`
`
`
`t-r.Examples 3
`
`the inert carrier i_ncl-ade 8 so lid carrier and a
`
`l;
`
`ii.qui
`
`carrier,
`
`The herbicide of the present
`
`invention is
`
`us uell_y prepared by
`
`further
`
`adding the other auxiliary
`
`agents
`
`for
`
`foirulitin such
`
`as
`
`surfactants,
`
`sticters,
`
`dispersers,
`
`and stabilizers,
`
`to formulate ante wettable
`
`powders,
`
`water
`
`dispgr31bie
`
`granules,
`
`suspension
`
`20
`
`eencentrates
`
`granules,
`
`dry
`
`flowables,
`
`emulsifiable
`
`concentra1es,
`
`aqueous
`
`solutions, oil
`
`solutions,
`
`smoking
`
`agents, aerosols, mic;ocapsule—s
`
`and the etherei
`
`In the
`
`herbicide of
`
`tie gmesent
`
`invention,
`
`the compound 0f
`
`the
`
`preceent
`
`invention is contained in a range of usually 0.1 to
`
`25
`
`80% by weight°
`
`
`
`[0008]
`
`A,
`FT}-xamnles of the solid carrier incl
`
`_ude fine powders or
`
`granules of clays
`
`(for example, kaolin clay, diatomaceons
`
`earth,
`
`bentonite,
`
`synthetic hydrated silicon oxides, Fubasami clay,
`.J
`or acid white clay),
`
`fiJ {:1 m
`
`other
`
`inorganic
`
`minerals
`
`(for
`
`exampW1,
`
`s ricjte, quartz powders,
`
`sulfur
`
`powders,
`
`active
`
`carbon,
`
`calci um carbonate
`
`or hydrated
`
`silica).
`
`Examples of
`
`the liquid carrier
`
`include water;
`
`alcohols {for example, methanol er ethanol); ketones
`
`(for
`
`examlle,
`
`acetone
`
`or methyl
`
`ethyl
`
`1“etoneh
`
`ar,uati
`
`n'w'drecabans (for Examfle,
`
`toluene, xylene, ethgl benzene,
`
`or methylnephthalene); aliphatic hydrocarbons (for example,
`
`nehexane,
`
`cyclohexane 0r keresene); esters
`
`(for example,
`
`ethyl acetat, er butyl acetate); nitriles (for example,
`
`acetonitrile or
`
`isobutyronitrile);
`
`ethers
`
`z"~ ror
`
`example,
`
`diisepropyl
`
`ether);
`
`and
`
`amides
`
`dimethylformamide or diwctqv-aeetaWide)
`
`n
`
`C‘ H
`
`(
`
`example,
`
`[0009]
`
`[‘1
`
`alky
`
`3“"
`
`xamples of
`
`‘the surfactants include alkyl sulfates,
`
`sulfonaies, alkyl aryl sulfenates, alkyl argl ethers
`
`and polyexyethylenate
`
`compounds
`
`thereof, p-elyexyeth-ylene
`
`glycol ethers, polynydric alczehel esters, and sugar alcohol
`
`derivatives.
`> H\J
`C
`
`”lJ
`
`tux
`
`ri.
`
`Examples efi the other auxiliary agents for ferLulatien
`
`U:
`
`l‘
`0
`
`U1
`
`.
`
`[\3
`
`[\J U1
`
`
`
`inilude a binder
`
`and
`
`a dispersant.
`
`Speoif ‘._J. .o
`
`examples
`
`include
`
`casein,
`
`gelatin,
`
`polysaccharides
`
`(for
`
`example,
`
`starch, gum arable, cellulose derivative: or alginio acid),
`
`lignin
`
`derivatives,
`
`bento nite,
`
`sugars,
`
`waterwsoluble
`
`synthetic
`
`polymers
`
`(for
`
`examgle,
`
`polyv-nvl
`
`alcohol,
`
`polyxinyl pyrrolj.done or polyacrylic acids),
`
`PAP
`
`(acidic
`
`isopropyl
`
`phosphate),
`
`BHT
`
`{2,6—di—tert—butyl~4~
`
`NFfDV'Db
`
`,
`
`BEA
`
`(a mixture
`
`of
`
`Zeter‘t Hbu:ylm 4m
`
`methoxyphenol and 3“text~butyl~ 4methoxyphenool) , plant oil,
`
`mineral oil, fatty acid and the others.
`
`[00 l}P..§
`
`A method
`
`for
`
`coitrolling weeds
`
`of
`
`the peserit
`
`invention comprises a step of applying an effective amount
`
`or
`
`a compound of
`
`the present
`
`invention to weeeds or soil
`
`where weeds are growing or will grow,
`
`In the method for
`
`controlling weeds of
`
`the present
`
`invantion, usually,
`
`the
`
`compoe-nd of the piesent invention is used as a herbicide of
`
`the pressent
`
`invention.
`
`Examples of the me-hod of applying the compound OF "he
`
`present
`
`inventior
`
`incl.ude a method of applying the present
`
`compound to stems and l_eaves
`
`if weeds, a method of applying
`
`the present compound to a surface 0
`
`soil where weeds are
`
`growing or will grow, a method of incorporating the present
`
`compound into so‘l where weeds are growing, and a method of
`
`applying the present compound to a surface water of pa Tdy
`
`U‘!
`
`10
`
`[\J (7
`
`PO
`
`
`
`field that an ax?a where weeds are growing 0: will grow is
`
`f]_coded
`
`[0012]
`
`.‘I
`.1.
`:1
`xamp es of
`
`the weeds which can be controlled by the
`
`(II
`
`present CvMWOE Ci
`
`incluue the following weeds, but are n t
`
`limited thereto.
`
`Urticaceae weer s: Urtica urens;
`
`Po 1y alaceae Naed3: Poljgonum convo.lvulus,
`
`Polygonum
`
`lapatbifblium,
`
`Polygonum
`
`pensylvanicum,
`
`Emlyganum
`
`>persicaria,
`
`Polygonum longisetum,
`
`Polygm Lzm
`
`avicalare,
`
`Pomlygonum ar.nastrum, Polygonum cuspidatum, Rumex japanicus,
`
`Rumex crispLs, Rum&x obtusifblius, and Rumex at tos7;
`
`Portulacaceae weeds: Fortyaca 01eracea;
`
`Lavyushvllseas weeds:
`
`Stellar.ia media,
`
`Stellaria
`
`aquatica, Cerastium halosteoides, Car‘stium glameratum,
`
`Spergu la arven sis, and
`
`U) H :~.s \’D B (D
`
`ga_LLica Va
`
`Mallugj_naceae weeds: fibllugo verLicil lata;
`
`Chenopodiaceae weeds: Chenoradium album,
`
`ePQJQdILL
`
`:mnrosioiaes, Kbchia scaparia, Salsola kali,
`
`and Atliplex
`
`Amara nthaceae
`
`weeds:
`
`Amaranthus
`
`rewroflexus,
`
`Amararltflus Viridis, Amarantl“s lividus, Amaranthus spinosus,
`
`Amaranthus hybri us Amaran thus Qalmeri, Amaranthus rudis,
`
`E\) U":
`
`Amaranthus
`
`gmatulas,
`
`Amar5u7LhLzs
`
`tuberculatos, Amaranthus
`
`
`
`_blitoidek,
`
`Amaranthus
`
`daflexus,
`
`Amararzthus
`
`quitensis,
`
`Alternantherfi phi oxeraicbs, Alt-Inahmhera sessilis,
`
`and
`
`Papaveraceae weeds:
`
`Papaver
`
`rhoeas,
`
`and Argemone
`
`U1
`
`mexiaana;
`
`Brassicaceae weeds: Raphanus
`
`raphanistrum, Raph?nus
`
`sativus,
`
`Sinapis
`
`arvensis,
`
`C"psella
`
`bursa pastcris,
`
`Rorippa
`
`islandica, Rorippa
`
`sylvestris,
`
`~[1162301
`
`arvense,
`
`f“)
`
`Ryagrum .ruggsum, Lapidium Virginicum, Cor01nqpu5 didymus,
`
`CaDJaLaFLa weeds: Clere affiniw;
`
`Wwe0 Q:
`ceae weeds: Aescbynamene
`
`indica, Aewchvpomel
`[V
`exaltata, Cassia ortusi1alia, Vass1a
`
`j...) (1
`
`rudiS),
`
`Sesbania
`
`occidentalis, Desmodium tortuosum, Desmodium adscendens,
`rrl
`Desmodium illinoense,111folium re*ens, Pueraria iobata,
`
`Vicia
`
`angustifolia,
`a
`
`Indigofera
`
`hirsuta,
`
`Had (.jo.fera
`
`truxillensis, ana Vigna sinensis;
`
`Ozalidaceae weeds: Oxalis corniculata, Ckalis strica,
`
`Geraniaceae weeds: Geranirm carolinense,
`
`and uradian
`
`Cicutarium;
`
`Euphexbiaceae weeds: Euphorbia ne11oscop1a, Euphorbia
`
`maculata, Euprwozb ia humistrata, Euphorbia esula, Eupho1bi
`
`E13
`
`fir"UP
`
`1‘») m
`
`
`
`heterophylla,
`
`EULh
`
`a
`
`.braSllleflSlS,
`
`,iuaivpn
`
`auvtralis,
`
`Cretan
`
`glandulosus,
`
`Cretan
`
`Jobatjs,
`
`Puylianthus
`
`PQ?COVdQeq5 S, and RiCiLUS “ijunis;
`
`{0015]
`
`U1
`
`10
`
`Malvac eae
`
`weeds:
`
`Abutilon
`
`thegphrmsti,
`
`Sida
`
`rhombiforia, Sida cordifclia, Sid? STinosa, Jida glaziovii;
`
`Sida Santa remnensis, Hibiscus trionum, Anoda cristata, and
`
`mhlvagtrum coromandelianum
`
`a;
`
`Onaqraceaa weeds:
`
`Ludwigia
`
`epilobioides,
`
`Ludwigia
`
`octavalvis,
`
`Ludwigia
`
`defiurre, Oenothera
`
`biennis,
`
`and
`
`Sterculiaceae weeds:
`
`altheria indica;
`
`W olaceae weeds: Viola ai.ven31s, and V“Fla tricolor;
`7
`
`O 5.3 (‘1 321kg 0‘ 3.1 Ff Q) r)
`,eae weeds: Sicyos angulatus,
`
`ECninocyst S
`
`lobata, and Rbmordica charantia;
`
`Lythraceae
`
`weeds:
`
`Ammannia multiflora,
`
`Anrmannia
`
`auriculata, AJmannia
`
`caseinea,
`
`L3thrmn valicaria,
`
`and
`
`Rotala indica;
`
`Elatinaceae wsedrz Elatine
`
`triandra,
`
`and glatine
`
`N (I)
`
`caii.fornica;
`
`Aniaceae weeds: Oenanthe i9vanica,>0aucus carota, aid
`
`Conium macuiatum;
`
`Araliaceaé waeds:
`
`H ycirocoty_Je
`
`sibthorpioides,
`
`and
`
`Hydrocotyle ranunculoides;
`
`
`
`C51
`
`:__) {:3
`
`PL) _)
`
`Ceratophyll.aceae weeds: ”ethfibhyllum dezne1sum;
`
`Cabomb ceae weeds: Cabamba caroliniana;
`
`Haloragaceae
`
`weeds:
`
`Myriophyllum
`
`aquaticum,
`
`Myriophyllum verticilla‘um, and Watermmilffiils
`
`for example,
`
`ffmiochyllum SWicatum, and RELLOEHVIJLM heterqphLllun);
`a
`Sapindaceae weeds.
`
`,11alospermum ha].1cacabum;
`
`Primulace ae weeG
`
`{n
`
`w:3 >3)
`
`q
`
`Asclepiadaceae weeds: Ascleaias syriaca, and Am’elafflUS
`
`albidus;
`
`Rubiaceae weeds: Galium aparine, Galium spur'z1m var.
`
`.Chinospermon, Spermacoce latifolia, Ricgardia brasili.ensis,
`
`an” Borreria alata;
`
`[@017]
`
`Convolvulaceae weeds:
`
`Ipomoea nil,
`
`Ipomoea hedezacea,
`
`Ipomoea
`
`“u1purea,
`
`ffiomoea bederacea var.
`
`integriuscule
`
`Ipcmoea
`
`lacunosa,
`
`Ipomcea
`
`triloba,
`
`.L
`Ivomoea
`
`acuminata,
`
`.T.pomoea hederifolia,
`
`lpomoea cocci flea,
`
`1pom053a quamocl1t,
`
`Ipomoea grandifolia,
`
`Ipomoea eristolochiafhlia,
`
`Ipomoea
`
`cairice,
`
`Convolvulus
`
`arvensis,
`
`Calyrt;gia
`
`‘hederacea,
`
`Calystegia jepon1ca, MErren 1a hedeacea, xErremia aegyptia,
`
`fifir1ujia ais&oides, and Jacquemontia tamnifolia;
`
`L
`y
`Bcra in ceae weeds: fifiogotis arvensis;
`
`Lamiaceae weed:: Eamium purpureum, La111am amplexicaule,
`
`g: E:- ‘J
`
`:3 (D U (D "f ‘21) 'b "hD Fq p Q.) n
`
`C5 f‘f 1... (fl
`
`:‘v-aV:
`
`suaveolens, Hyptis lophanta,
`
`Leonurus si izicus, and Eta Chvs arL- nsis;
`
`
`
`Ln
`
`I...)
`
`\.
`in) l1
`
`Solanaceae weeds: Datura stramonium, Solanum nigrum,
`
`Jo lanum
`
`‘Hericanum,
`
`Solanum
`
`ptycanthum,
`
`Solanum
`
`sarrachoides, Solanuj
`
`rOStratum,
`
`Solanum acuieatissimun
`
`angula ta, Physalis sub.1abrata, and Nicandra physrloides;
`
`Scrophulariaceae
`
`weeds:
`
`Véronica
`
`hederaefolIia,
`
`Véronica persica, Varonica arvegsis, Linde111a procumbens,
`
`Lindernia
`
`dubia,
`
`Lindgrnia
`
`angustijolia,
`
`Bacqpa
`
`rotundifolia, Depatrium junceu1, and Gratiola japonica;
`
`Pic1ntaginaceae weeds:
`
`Plantago
`
`aviatica,
`
`Plantago
`
`steraceae weeds: Kanthium pensvlvanicum,
`
`:an:h1um
`
`orC111ncale,
`
`Kanthium
`
`italicum,
`
`HElianthus
`
`anLurs,
`
`thrica.r1a chamomilla, Phtricar1a perforata, Chrysanthemum
`
`segetum, khtricaria matricarioidea, Hrtemisia princeps,
`
`Artumisia
`
`vulgaris,
`
`Artemisia
`
`verlotorum,
`
`Solidago
`
`altisgifla,
`
`Taraxacum
`
`officinale,
`
`Galinsoga
`
`ciliata,
`
`Gal1nsaqa
`
`WJrVIfJCLa,
`
`Se nec1o
`
`vulgar1s,
`
`Senec1c
`
`brasiliensis,
`
`Senecio
`
`g1isebachii,
`
`Conyza
`
`bonari nsis,
`
`Ccnyza
`
`canadens 1.5,
`
`Ambrosia
`
`artemisiaeffilia,
`
`Afibrosia
`
`trifida, Bio?ans firipartita, B’dens pilasa, Bidens frondosm,
`
`Bidens
`
`subalternars,
`
`1rS'1um arvense, Cirsium vulgar“,
`
`I‘d (I!
`
`Silvbum marianurn Carduus nutans, Lactua serriola, Sonohus
`
`
`
`11
`
`11eraceus,
`
`Sanchus
`
`Tsper, W3d311a
`
`glauca,
`
`k@lampod1um
`
`perfbl1atum,
`
`Emilia
`
`sonchifblic,
`
`Tagsetes
`
`m iuuzta,
`
`Blainvillea
`
`latifolia,
`
`Trimax
`
`‘procumbens,
`
`PorophVllum
`
`ruaerale, Acanthospermum australe, Acanthespermum hiflpidum,
`
`5
`
`Card1055permum hal 1cacaquu Ageratum conyzoides, Eupator1um
`
`_peifoliatum,
`
`“Clipta
`
`alba,
`
`grachtites
`
`hieracifolia
`
`Gamachaeta spicata, Gnaphalium mpicatum,
`
`Jfivegeria hirta,
`
`Pa.rther1um hystergphorus, Q19990L Ckia orientalis, Saliva
`
`i
`
`_ 14-1
`,Eclipta mrostrata, Eci1vta alba,
`
`and Centi eda
`
`sess1lis
`'4 .
`m1n1ma,
`
`“A
`1U
`
`[0020]
`
`I1lismataceae weeds: Sagittaria pygmaea,
`
`“agittaria
`
`I
`_
`J
`I
`U
`trifolia Sacittaria santtifolia Sa"1ttar1a mflwtev1den
`
`:1 “r
`Sagi
`
`3:
`
`aginashi, Alisma
`
`canalic‘latum,
`
`and Alisma
`
`:1.) U"
`
`_plantagowaquatica;
`
`Limnocharitaceae weeds: Limrocha11s flava;
`
`1
`1
`H drochari aceae weAds: Limnobium swan 1a, Hvdrilla
`
`verticillata, and NajaS gua alupensis;
`
`Ar1ceae weeds: P1sala StraC30tes;
`
`20
`
`Lemnaceae weeds: Lemma aoukikusa, Srirod113 gfilyrhiza,
`
`and Wolffia spy;
`
`Potamcgetona,e ae weeds:
`
`Potamogeton digtinctus,
`
`and
`
`90nd weeds
`
`(for exampla, Pot amageforl CIiSLUS, Potamogeton
`
`1111noensis, and StuckeEiaIpectinata);
`
`2r
`
`Liliaceae weeds: Allium canader5e, Allium Vineale, and
`
`
`
`12
`
`Allium macros temom;
`
`Pantederiaceae
`
`we&dsz
`
`Michhornia
`
`crassipes,
`
`Heteranthera limosa,
`
`ipnochfiria korsakowii,
`
`and anochoria
`
`"aginalis Nb
`
`S
`
`2)..
`Commelinaceae weeus:
`
`Commelina
`
`J‘MMflfiiS,
`
`Commelina
`
`benghareflsis, Comma ina erecta, and Rurdannia keisax;
`
`[0021]
`
`:3(
`
`r__)
`
`\
`~\”A; I‘
`
`Peas?ae weeds:
`
`Echin0¢Mil a
`
`eras—galli, Eaginochloa
`
`crugwgalli
`
`var
`
`formosensig,
`
`Echinoczloa
`
`aryToi<jes,
`
`Echinoch Ga
`
`colona,
`
`Lchinochloa
`
`crusjpavonis,
`
`Separi
`
`annua, goa trivialis,
`
`’oa Dratensis, Alospecurus aegualis,
`
`Alopecurus myesuraides, Avena
`
`fatua,
`
`Sarghum halepense
`
`I
`
`Sorghmn vulgare, Ag.ropyron rep-J23, Lo
`
`UH perenne, Lolium
`
`rigidum,
`
`Bremus
`
`cathtrti~us,
`
`Bromus
`
`sterilis,
`
`Bromus
`
`japonicus,
`
`Bramus
`
`sscalifius,
`
`Bramus
`
`tectorum,
`
`HOrdeum
`
`jub?tum,
`
`Aegilqps
`
`cylindrica,
`
`Plalaris
`
`arundinacea,
`
`20
`
`Phqlfris minor, Zpera “picamventi, Pamicum texanum, Panicum
`
`maximum, Brachiazia D_atypnylla, Bracniaria ruziziensis,
`
`Bracliaria plantaginea, Bracbiaria decumbfins,
`
`rach.iaria
`
`orizantJa, Brachiarix
`
`lamidicola,
`
`Cencbzu s
`
`echinatus,
`
`Cenchrus Jauciflorus, Eriochloa villosa, Pennigetum setosum,
`
`Fx) L1
`
`9 H O 1“: j.” (0
`
`\Q Q31. g ‘5
`
`t1 H )1; Q
`.rostis jDilOSa, Rhynchelitrum repens
`
`
`
`13
`
`Dac tyioctem: u1
`
`aegyptium,
`
`Ischaemum rugosum,
`
`Isachne
`
`globosa, Oryza sativa, Paspalum no ta um, Ms pa lam maritimun,
`
`Paspaium disticgum,
`
`Pennisetum Clanaest_inum,
`
`Pennisetum
`
`Q P)
`
`uosuu, Rot“boellia cochinchinensis, L1ptoclloa chinensis,
`
`,paflicriwes, Leersia
`
`jabonicm, L;er51T sayanuka, Leersia
`
`Gig/1:5ria maxima,
`
`.Aqrdstis stolonifeza, Qym1odon dactylan,
`
`J
`Ucct“115
`
`lomerata,
`
`Eremochl 0a
`
`-
`ophiuroideS,
`
`FEstuc a
`
`arundinacea, EEstuca rubra, IJJerat¢ cylindricaf Pfiscanthus
`
`sinensis, Panicum virgatum, and Zoysi
`
`japon1_a;
`
`Cyperaceae weeds: Cyperus microiria, Cyperus
`
`iria,
`
`cyperus compressus, cyper“s diffjrmis,
`
`’yp=rus :1?cciaus,
`
`11
`Cvnerrs
`
`2
`
`lobosus,
`
`C' eras
`
`y
`nipwonics,
`
`1
`LN eras oderrtus,
`
`Cyperus serotinus, pyperus
`
`1o tundus, Cyperus escul ertus,
`
`Kyllinga
`
`graci17linza, Kvllinga brevifcl1a,
`
`F1mb1is§ty113
`
`miliaccfi,
`
`[ihbristylis dichotoma, E19eocharis ac.:milaris,
`
`Eleocfiaris
`
`oguwai,
`
`Schoenop2.ectus
`
`hotarui,
`
`Schoenqplectus
`
`juncHaijes,
`
`Schoenop
`
`ctus
`
`vzallichi1,
`
`Sc.oenaplectu: m7c.ronatus,
`
`SChecanpleatus
`
`triangulatus,
`
`Schoenovlec+us
`
`n1pp0n1cus,
`
`Schoenop leccus
`
`;r1gae1er,
`
`BolhoschJanus Koalevnikovii, m1d Bolboschoenus flrviatilis;
`
`Pd .0 S I“! U: (D r 9) O m D) m
`
`5»: (E, (D :21 m
`
`3er£21: H. m (T) f+ g.:3
`
`Q) 1<*i(D ’3 in VI)
`
`in :3 Q
`
`31'
`
`QS 1., 1 rr £11‘5;
`
`U1
`
`1
`
`0
`
`£3
`
`2
`
`0
`
`(J?
`
`
`
`14
`
`Salviniaceae weeds: Salvinia netens;
`
`Azolleceee
`
`weeds:
`
`Azolla
`
`japonica,
`
`and
`
`‘Azolia
`
`Magsileaoeae weeds: kfirsilea quadrifolia; and
`
`O;her
`
`weecs:
`
`filamenteus
`
`algae
`
`F3
`(f0:
`
`example,
`
`ithophora}
`
`...I
`Cmadophera), mosese,
`
`liverwort,
`
`hornwort,
`
`mz
`
`cyanobaeteria, bracken, and sucker of permanent crops
`
`0 I:
`
`C
`example, oome fruits, stone fruits, berry fruits, nut fr it,
`
`citrus fruit, hep, grapes, ano the others)»
`
`10
`
`EXAMPLES
`
`[0323 x.....n
`
`Hereinafter,
`
`the present
`
`invention is explained in
`
`more detail by using Preparation Example and Test Example,
`
`however,
`
`the present
`
`invention sho=1d not be
`
`limited to
`
`these examples.
`
`rnn04
`
`m k4! 1’: (J) (-4-
`
`r'?‘ ‘3‘ (D
`
`"U H '3 .3 H Cu ('i' F1. O :3
`
`[‘1 N m i H {T} (i)
`
`DJ H (E)
`
`U} :23‘ O 2 1’3
`
`[0025]
`
`1“.)
`
`r",s.“
`
`Preparation Example 1
`
`
`
`?_<J
`
`(1"?
`
`KCCN
`
`”mm—mm»
`ACCH 1 H- C)
`
`2
`
`a
`
`e
`
`“fix—1'
`{3’
`
`in
`H33
`
`F
`
`\K "5/
`
`o
`
`a
`
`,
`
`h
`(-1-: E
`
`‘N
`
`{3}
`
`F
`I‘
`
`,J
`
`Q
`\
`
`5""
`
`xx:
`syn-é
`Q
`53)......3’r
`3kg ""‘
`erg
`
`{2}
`
`H3
`
`One point
`
`two (1.20) grams of a compound represented
`
`....
`by tie above~mentioned formula (2) was added to a mixture
`
`of 18 mL of acetic acid and 2.7 mL of water,
`
`and thereto
`
`CD
`
`was added 572 mg of potassium cyanate.
`
`The mixture was
`
`:tirred at
`
`room temperature
`
`for
`
`two hours,
`
`and
`
`then
`
`concentrated under reduced pressure.
`
`The obtained resieues
`
`erred tQ ea silica gel
`
`column chromatography to
`
`give
`
`1.10
`
`g of
`
`a
`
`cempound
`
`represented by
`
`the
`
`abovem
`
`meltioned formula (3).
`
`leNMR (WMSOMdg): 5(0pm): 8°56 (1H, d,
`
`J = 2,0 HZ), 7.91
`
`(1H, d, J = 10.9 Hz), 7.21 (1H, dd, J 2 7.9, 1.4 HZ), 6,99
`
`(1H, dd; J = 709,
`
`5~O Hz), 6.24 (2H, 8), 4.93 {2H, S), 4.10
`
`‘ZH,
`
`\, J 2 7.1 HZ), 1.15 (3H, t, J m 7.1 Hz).
`
`[0026]
`
`Preparation Example 2
`
`
`
`16
`
`
`
`Zero point
`
`two eight
`
`(0.28) ml of acetVl chloride w-s
`
`added dtopwise to a
`
`lnixtute 0f 0.30 g of
`
`the compound
`
`represented by formula (3), 0.38 mL of pyridine and 7.0 mL
`
`of
`
`tetrahydrofurau at
`
`room temperature.
`
`The deture was
`
`stirred‘ at
`
`éOQC for
`
`6 hours,
`
`and then cooled to room
`
`temperature» Water was added to the resulting mixture, and
`
`3
`3)
`the mixture was extrlcted with ethyl acetate.
`
`..J e obtained
`
`T}
`
`organic layer was washed with saturated brile and dried
`
`over anhydrous magnesium sulfate,
`
`and concentrated under
`
`reduced pressure.
`
`The obtained residues were washed with
`
`chloroform to give UOZE g ofi
`
`the compound of
`
`the greseht
`
`inventiel.Q
`
`leNMR (peso—d5): 5(ppfl}: 7°91 (1H, dd,
`
`J : 4.9i 1.6 Hz),
`
`(.Fl
`
`10
`
`{)1
`
`IX) C
`
`
`
`Next, Test example? are
`
`U)
`
`hown below‘
`
`{0028]
`
`U1
`
`10
`
`Test Example 1: Pestwemergenee treatment test in a farmland
`
`lursery scil was put
`
`in a plaetic pot measuring 8
`
`cm
`
`in UiuuHLFL and 6.5 cm in height, and in the pet,
`
`seeds of
`
`Am“ranthue
`
`retrofiexus were
`
`sowny
`
`and.
`
`k,
`then covered with
`
`eeil of about 0~5 cm thickness,
`
`and the plant» were grown
`
`in a greenhouse.
`
`When the Amaranthus retrofleexus plants
`
`were g;wow to twenleaf stage, a diluted solution containing
`
`either the present compound or
`
`a
`
`czompound regx
`
`ented by
`
`formula (B) below {which is described in European Patent No
`
`U
`
`11222-4 F14‘:-
`
`2)
`
`{Kereinafter,
`
`referred to as Compound B)_was
`
`uni ormly
`
`sprayed on
`
`the whole Amaranthus_ retroflexus
`
`plan"e so that the apfielic:ion ratee of the chemicals would
`
`L51
`
`be values indicated in Table l.
`
`mere the diluted solution was prepared by disselvin;
`
`the prerent compound or the CCI'mpOLIHd B in dimetnylfo:mamide
`
`eolutien
`
`containing
`
`2%
`
`of
`
`Tween
`
`20
`
`(p elyoxvetl lene
`
`serbitan fatty acid ester)
`
`(mane-1e ctured by MP Bi omediea.L“: s
`
`lneo) end then dil‘utiing the solution with deionized water.
`
`The Amarantfius retroflexns plants that were
`
`m
`
`ye d
`
`with the diluted solution containing the present compound
`
`or
`
`the compound B rere grown in a greenhouse. Nine days
`
`after
`
`spraying,
`
`the efficacy for controlling' Amerarithus
`
`retrorlexus plants was
`
`\beerved,
`
`thereby
`
`examining
`
`a
`
`
`
`18
`
`,.J p 9) 4.4
`herbicidal effect. Here the herbic‘
`
`(B H h“. (D 0H Z {I} U}
`
`{N i...) U) {.1 DJ
`
`observed and evaluated by classifying the effect
`
`into ll
`
`$3.!
`
`(I)g 8
`
`st
`
`Fl
`
`IOHL
`
`0
`
`(no =ffect)
`
`to 10
`
`(complete kill)“
`
`The
`
`results are shown in Table l~
`
`The results showed that
`
`a.
`the present
`
`compound showed
`
`nigger herbicidal effect compared to the compound B.
`
`Application Ratel Herbicidal Effect
`Of the Chemicals
`
`
`
`
`Inhibitory Activity on Emergence Qt ArabidOWSis tnaliana
`
`Each well of 24 well microtiter plates was matted with
`
`a filter paper,
`
`and to the filter paper was added dropwise
`
`the solution in which the present compound or the compound
`.u
`,__
`ved in acetone. After airmdrying, distilled
`
`B was diesel
`
`water was added to each well so that
`
`the concent.atien of
`
`lO
`
`l5
`
`
`
`19
`
`the p;eeent compound or the compound B in each well wou
`
`be SGOO ppm. Next, seeds of Arabidopeis thaliana were 30'
`
`into each well containing the present
`
`compound or
`
`the
`
`compound B,
`
`followed by putt Mfg a
`
`lid on each well,
`
`and
`
`5
`
`cultivating Arebidopsis thaiiana under the condition that
`
`cultivation at
`
`259C under
`
`lighting for
`
`16 hours
`
`and
`
`successive cultivation at 25°C undet dark for 8 hours were
`
`repeated.
`
`Seven days after sowing,
`
`the inhibitory activity
`
`on emergence of Arabidcpsis thaliana was Vi
`
`U)
`u ally evaluatet
`
`10
`
`by classifying the activity into 0
`
`to 100 indices
`
`(0:
`
`effect
`
`to 100:
`
`no emergence).
`
`The results are shown
`
`no
`
`in
`
`Tfible 2.
`
`The
`
`result
`
`showed 'that
`
`the
`
`reeent
`
`compound showed
`
`higher inhibitory activity compared to the compound B.
`
` Treatment.
`
`Concentration
`
` Compound 8
`
`[lndue”rial FpplicabilitV]
`
`[0032}
`
`20
`
`The compcound of the present invetti on has excellent
`
`efficacies for controlling weeds, and is useful as an
`
`active ingtedient for an agent for controlling weeds.
`
`
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