JP2015036372A - 置換ピラゾリルピラゾール誘導体とその除草剤としての使用 - Google Patents
置換ピラゾリルピラゾール誘導体とその除草剤としての使用 Download PDFInfo
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- JP2015036372A JP2015036372A JP2013168378A JP2013168378A JP2015036372A JP 2015036372 A JP2015036372 A JP 2015036372A JP 2013168378 A JP2013168378 A JP 2013168378A JP 2013168378 A JP2013168378 A JP 2013168378A JP 2015036372 A JP2015036372 A JP 2015036372A
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- 239000004288 Sodium dehydroacetate Substances 0.000 description 1
- ABBQHOQBGMUPJH-UHFFFAOYSA-M Sodium salicylate Chemical compound [Na+].OC1=CC=CC=C1C([O-])=O ABBQHOQBGMUPJH-UHFFFAOYSA-M 0.000 description 1
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- GUJOJGAPFQRJSV-UHFFFAOYSA-N dialuminum;dioxosilane;oxygen(2-);hydrate Chemical compound O.[O-2].[O-2].[O-2].[Al+3].[Al+3].O=[Si]=O.O=[Si]=O.O=[Si]=O.O=[Si]=O GUJOJGAPFQRJSV-UHFFFAOYSA-N 0.000 description 1
- 125000006003 dichloroethyl group Chemical group 0.000 description 1
- 238000007865 diluting Methods 0.000 description 1
- HNPSIPDUKPIQMN-UHFFFAOYSA-N dioxosilane;oxo(oxoalumanyloxy)alumane Chemical compound O=[Si]=O.O=[Al]O[Al]=O HNPSIPDUKPIQMN-UHFFFAOYSA-N 0.000 description 1
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- NVVZQXQBYZPMLJ-UHFFFAOYSA-N formaldehyde;naphthalene-1-sulfonic acid Chemical compound O=C.C1=CC=C2C(S(=O)(=O)O)=CC=CC2=C1 NVVZQXQBYZPMLJ-UHFFFAOYSA-N 0.000 description 1
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- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 1
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- NLYAJNPCOHFWQQ-UHFFFAOYSA-N kaolin Chemical compound O.O.O=[Al]O[Si](=O)O[Si](=O)O[Al]=O NLYAJNPCOHFWQQ-UHFFFAOYSA-N 0.000 description 1
- 239000003350 kerosene Substances 0.000 description 1
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- 239000000594 mannitol Substances 0.000 description 1
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- 235000010755 mineral Nutrition 0.000 description 1
- 239000002480 mineral oil Substances 0.000 description 1
- 235000010446 mineral oil Nutrition 0.000 description 1
- 229910052901 montmorillonite Inorganic materials 0.000 description 1
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- SNQQPOLDUKLAAF-UHFFFAOYSA-N nonylphenol Chemical class CCCCCCCCCC1=CC=CC=C1O SNQQPOLDUKLAAF-UHFFFAOYSA-N 0.000 description 1
- 239000003921 oil Substances 0.000 description 1
- 239000002420 orchard Substances 0.000 description 1
- 125000005702 oxyalkylene group Chemical group 0.000 description 1
- FJKROLUGYXJWQN-UHFFFAOYSA-N papa-hydroxy-benzoic acid Natural products OC(=O)C1=CC=C(O)C=C1 FJKROLUGYXJWQN-UHFFFAOYSA-N 0.000 description 1
- 229960005323 phenoxyethanol Drugs 0.000 description 1
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- 229920001495 poly(sodium acrylate) polymer Polymers 0.000 description 1
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- 229920000036 polyvinylpyrrolidone Polymers 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- TYJJADVDDVDEDZ-UHFFFAOYSA-M potassium hydrogencarbonate Chemical compound [K+].OC([O-])=O TYJJADVDDVDEDZ-UHFFFAOYSA-M 0.000 description 1
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- FKERUJTUOYLBKB-UHFFFAOYSA-N pyrazoxyfen Chemical compound C=1C=C(Cl)C=C(Cl)C=1C(=O)C=1C(C)=NN(C)C=1OCC(=O)C1=CC=CC=C1 FKERUJTUOYLBKB-UHFFFAOYSA-N 0.000 description 1
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- 238000010898 silica gel chromatography Methods 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- 238000004513 sizing Methods 0.000 description 1
- 235000010413 sodium alginate Nutrition 0.000 description 1
- 239000000661 sodium alginate Substances 0.000 description 1
- 229940005550 sodium alginate Drugs 0.000 description 1
- WXMKPNITSTVMEF-UHFFFAOYSA-M sodium benzoate Chemical compound [Na+].[O-]C(=O)C1=CC=CC=C1 WXMKPNITSTVMEF-UHFFFAOYSA-M 0.000 description 1
- 235000010234 sodium benzoate Nutrition 0.000 description 1
- 239000004299 sodium benzoate Substances 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 235000017550 sodium carbonate Nutrition 0.000 description 1
- 235000019812 sodium carboxymethyl cellulose Nutrition 0.000 description 1
- 235000019259 sodium dehydroacetate Nutrition 0.000 description 1
- 229940079839 sodium dehydroacetate Drugs 0.000 description 1
- 239000012312 sodium hydride Substances 0.000 description 1
- 229910000104 sodium hydride Inorganic materials 0.000 description 1
- NNMHYFLPFNGQFZ-UHFFFAOYSA-M sodium polyacrylate Chemical compound [Na+].[O-]C(=O)C=C NNMHYFLPFNGQFZ-UHFFFAOYSA-M 0.000 description 1
- 229960004025 sodium salicylate Drugs 0.000 description 1
- DSOWAKKSGYUMTF-GZOLSCHFSA-M sodium;(1e)-1-(6-methyl-2,4-dioxopyran-3-ylidene)ethanolate Chemical compound [Na+].C\C([O-])=C1/C(=O)OC(C)=CC1=O DSOWAKKSGYUMTF-GZOLSCHFSA-M 0.000 description 1
- 235000010199 sorbic acid Nutrition 0.000 description 1
- 239000004334 sorbic acid Substances 0.000 description 1
- 229940075582 sorbic acid Drugs 0.000 description 1
- 239000000600 sorbitol Substances 0.000 description 1
- 235000010356 sorbitol Nutrition 0.000 description 1
- 241000894007 species Species 0.000 description 1
- 239000007921 spray Substances 0.000 description 1
- 239000008107 starch Substances 0.000 description 1
- 235000019698 starch Nutrition 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 239000004548 suspo-emulsion Substances 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 229960000278 theophylline Drugs 0.000 description 1
- ZFXYFBGIUFBOJW-UHFFFAOYSA-N theophylline Chemical compound O=C1N(C)C(=O)N(C)C2=C1NC=N2 ZFXYFBGIUFBOJW-UHFFFAOYSA-N 0.000 description 1
- 244000082735 tidal marsh flat sedge Species 0.000 description 1
- 238000002054 transplantation Methods 0.000 description 1
- 125000004205 trifluoroethyl group Chemical group [H]C([H])(*)C(F)(F)F 0.000 description 1
- 239000010455 vermiculite Substances 0.000 description 1
- 229910052902 vermiculite Inorganic materials 0.000 description 1
- 235000019354 vermiculite Nutrition 0.000 description 1
- 239000000080 wetting agent Substances 0.000 description 1
- 235000010493 xanthan gum Nutrition 0.000 description 1
- 239000000230 xanthan gum Substances 0.000 description 1
- 229920001285 xanthan gum Polymers 0.000 description 1
- 229940082509 xanthan gum Drugs 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
- 239000010457 zeolite Substances 0.000 description 1
- 229940043810 zinc pyrithione Drugs 0.000 description 1
- PICXIOQBANWBIZ-UHFFFAOYSA-N zinc;1-oxidopyridine-2-thione Chemical compound [Zn+2].[O-]N1C=CC=CC1=S.[O-]N1C=CC=CC1=S PICXIOQBANWBIZ-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
- C07D487/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains two hetero rings
- C07D487/04—Ortho-condensed systems
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
- A01N43/48—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with two nitrogen atoms as the only ring hetero atoms
- A01N43/56—1,2-Diazoles; Hydrogenated 1,2-diazoles
-
- 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
- A01N43/90—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having two or more relevant hetero rings, condensed among themselves or with a common carbocyclic ring system
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
- C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
- C07D471/04—Ortho-condensed systems
Landscapes
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Health & Medical Sciences (AREA)
- Plant Pathology (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)
- Agronomy & Crop Science (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Plural Heterocyclic Compounds (AREA)
Abstract
【解決手段】上記課題を解決できる特定のピラゾリルピラゾール誘導体が開示される。
【選択図】なし
Description
しかしながら、雑草の種類は多岐にわたり、また各雑草の発芽及び生育時期は一様ではなく、さらに、多年生雑草の発生は長期におよぶ。そのため一回の除草剤散布ですべての雑草を防除することは非常に困難である。
indica)、アゼガヤ(Leptochloa chinensis)、イボクサ(Murdannia keisak)などが挙げられ、これら難防除雑草に対して十分な効果を有する除草剤は少ない。
6,7−テトラヒドロピラゾロ[1,5−a]ピリジン−2−イル)−5−[メチル(プロプ−2−イニル)アミノ]ピラゾール−4−カルボニトリル(一般名:「ピラクロニル」,商品名ピラクロン)は広範囲な雑草に有効であるが、高葉齢のノビエに対する効果は十分でなく、日本での登録上の本剤単剤のノビエに対する適用範囲は1.5葉期までである。
R1はハロゲン原子を表わし、
R2はシアノ基、ニトロ基を表わし、
R3は1個またはそれ以上のハロゲン原子によって置換されたC2〜C4アルキル基、C1〜C2アルコキシ(C1〜C3)アルキル基を表わし、
aは3〜5を表わし、かつ
bは1〜3を表わす。
「ハロゲン原子」には、フッ素、塩素、臭素及びヨウ素原子が包含される。
「アルキル基」は直鎖状もしくは分枝鎖状であることができ、かつ置換基に含まれる水素原子の少なくとも1個がハロゲン原子に置換されており、限定されるものではないが、例に挙げると、クロロエチル、ジクロロエチル、トリフルオロエチル、テトラフルオロプロピル、ブロモエチル、ブロモプロピル、クロロブチル基などが挙げられ、指定の炭素原子数の範囲で選択される。
「アルコキシ基」は、アルキル部分が上記の意味を有するアルキル−O−基を意味し、限定されるものではないが、例えば、メトキシ、エトキシ基などが挙げられ、各々の指定の炭素原子数の範囲で選択される。
カ科雑草、タマガヤツリ(Cyperus difformis)、ミズカヤツリ(Cyperus serotinus)、ホタルイ(Scirpus juncoides)、クログワイ(Eleocharis kuroguwai)、コウキヤガラ(Scirpus planiculmis)、シズイ(Scirpus nipponicus)などのカヤツリグサ科雑草、アゼナ(Lindernia procumbens)、タケトアゼナ(Lindernia dubia subsp.dubia)、アメリカアゼナ(Lindernia dubia)などのゴマノハグサ科雑草、コナギ(Monochoria vaginalis)、ミズアオイ(Monochoria korsakowii)などのミズアオイ科雑草、ヒルムシロ(Potamogeton distinctus)などのヒルムシロ科雑草、キカシグサ(Rotala indica)、ヒメミソハギ(Ammannia multiflora)などのミソハギ科雑草、タウコギ(Bidens tripartita)、アメリカセンダングサ(Bidens frondosa)などのキク科雑草、クサネム(Aeschynomene indica)などのマメ科雑草、イボクサ(Murdannia keisak)などのツユクサ科雑草、タイヌビエ(Echinochloa oryzicola)、イヌビエ(Echinochloa crus−galli var.crus−galli)、ヒメタイヌビエ(Echinochloa crus−galli var.formosensis)、ヒメイヌビエ(Echinochloa crus−galli var.praticola)、ケイヌビエ(Echinochloa crus−galli var.caudata)、アゼガヤ(Leptochloa chinensis)、アシカキ(Leersia japonica)、キシュウスズメノヒエ(Paspalum distichum)、エゾノサヤヌカグサ(Leersia oryzoides)などのイネ科雑草などが挙げられる。
イヌホウズキ(Solanum nigrum)、シロバナチョウセンアサガオ(Datura stramonium)などのナス科雑草、イチビ(Abutilon avicennae)、アメリカキンゴジカ(Sida spinosa)などのアオイ科雑草、マルバアサガオ(Ipomoea purpurea)などのヒルガオ科雑草、イヌビユ(Amaranthus lividus)などのヒユ科雑草、オナモミ(Xanthium strumarium)、ブタクサ(Ambrosia artemisiifolia)、ハキダメギク(Galinsoga ciliata)、セイヨウトゲアザミ(Cirsium arvense)、ノボロギク(Senecio vulgaris)、ヒメジョオン(Stenactis annuus)などのキク科雑草、イヌガラシ(Rorippa indica)、ノハラガラシ(Sinapis arvensis)、ナズナ(Capsella bursa―pastoris)などのアブラナ科雑草、イヌタデ(Persicaria longiseta)、ソバカズラ(Fallopia convolvulus)などのタデ科雑草、スベリヒユ(Portulaca
oleracea)などのスベリヒユ科雑草、シロザ(Chenopodium album)、コアカザ(Chenopodium ficifolium)、ホウキギ(Kochia scoparia)などのアカザ科雑草、コハコベ(Stellaria media)などのナデシコ科雑草、オオイヌノフグリ(Veronica persica)などのゴマノハグサ科雑草、ツユクサ(Commelina communis)などのツユクサ科雑草、ホトケノザ(Lamium amplexicaule)、ヒメオドリコソウ(Lamium purpureum)などのシソ科雑草、コニシキソウ(Euphorbia supina)、オオニシキソウ(Euphorbia maculata)などのトウダイグサ科雑草、トゲナシヤエムグラ(Galium spurium)、ヤエムグラ(Galium spurium var. echinosper
mon)、アカネ(Rubia argyi)などのアカネ科雑草、スミレ(Viola
mandshurica)などのスミレ科雑草、アメリカツノクサネム(Sesbania exaltata)、エビスグサ(Cassia obfusitolia)などのマメ科雑草などの広葉雑草、野性ソルガム(Sorgham bicolor)、オオクサキビ(Panicum dichotomiflorum)、ジョンソングラス(Sorghum halepense)、イヌビエ(Echinochloa crus−galli var.crus−galli)、メヒシバ(Digitaria ciliaris)、カラスムギ(Avena fatua)、オヒシバ(Eleusine indica)、エノコログサ(Setaria viridis)、スズメノテッポウ(Alopecurus aequalis)、スズメノカタビラ(Poa annua)などのイネ科雑草、ハマスゲ(Cyperus rotundus)などのカヤツリグサ科雑草などが挙げられる。
,N−ジメチルホルムアミド、ジメチルスルホキシド、N−メチルピロリドンなど);水などが挙げられる。
90質量%程度が好ましく、より好ましくは0.5〜50質量%程度である。
以下の実施例により本発明を説明する。
5℃に冷却した無水酢酸(33.7g)に蟻酸(18.4g)をゆっくりと滴下し、60℃で2時間攪拌を行った(反応液A)。別途、5−アミノ−1−(3−クロロ−4,5,6,7−テトラヒドロピラゾロ[1,5−a]ピリジン−2−イル)ピラゾール−4−カルボニトリル(26.3g)をアセトニトリル(200ml)に溶かし、攪拌を行った。そこへ、先程調整した反応液Aをゆっくりと滴下し、室温で1日、60℃で4時間反応を行った。その後、溶媒を減圧留去し、炭酸カリウム水溶液を用いて中和し、析出した固体を水で洗浄し、乾燥後N−(1−(3−クロロ−4,5,6,7−テトラヒドロピラゾロ[1,5−a]ピリジン−2−イル)−4−シアノピラゾール−5−イル)ホルムアミド(28g)を得た。
得られたN−(1−(3−クロロ−4,5,6,7−テトラヒドロピラゾロ[1,5−a]ピリジン−2−イル)−4−シアノピラゾール−5−イル)ホルムアミド(4.4g)をN,N−ジメチルホルムアミド(15ml)に溶かし、炭酸カリウム(2.5g)を加え、攪拌を行った。そこへ、1−ブロモ−2−クロロエタン(2.6g)をゆっくりと滴下し、50℃で6時間反応を行い、反応終了後、反応液に水を加え酢酸エチルで抽出した。硫酸ナトリウムで乾燥後、溶媒を減圧濃縮し、粗生成物(5.2g)を得た。
得られた粗生成物(5.2g)をエタノール(20ml)に溶かし、10%塩酸(5.5g)を加え、65℃で3時間攪拌を行った。反応終了後、反応液に水を加え、析出した固体を濾取し、乾燥後、1−(3−クロロ−4,5,6,7−テトラヒドロピラゾロ[1,5−a]ピリジン−2−イル)−5−(2−クロロエチルアミノ)ピラゾール−4−カルボニトリル(4.5g)を得た。
1−(3−クロロ−4,5,6,7−テトラヒドロピラゾロ[1,5−a]ピリジン−2−イル)−5−(2−クロロエチルアミノ)ピラゾール−4−カルボニトリル(1.0g)をアセトニトリル(6ml)に溶かし、攪拌後、そこへトリフルオロ酢酸無水物(3.2g)をゆっくりと滴下した。40℃で4日攪拌し、反応液に飽和炭酸水素ナトリウム水溶液を加え、酢酸エチルで抽出した。硫酸ナトリウムで乾燥した後、溶媒を減圧留去し、得られた粗生成物をシリカゲルカラムクロマトグラフィー(ヘキサン/酢酸エチル=1:1)で精製し、目的物(0.9g)を得た。
5−アミノ−1−(3−クロロ−4,5,6,7−テトラヒドロピラゾロ[1,5−a]ピリジン−2−イル)ピラゾール−4−カルボニトリル(43.1g)をN,N−ジメチルホルムアミド(170ml)に溶かし、55%水素化ナトリウム(8.6g)を加え、攪拌を行った。発泡が収まったのを確認後、反応液を氷浴で冷やしながら2−ブロモエチルメチルエーテル(25g)をゆっくりと滴下し、滴下終了後60℃で8時間反応を行った。反応終了後、反応液に水を加え、析出した固体を酢酸エチルで洗浄し、1−(3−クロロ−4,5,6,7−テトラヒドロピラゾロ[1,5−a]ピリジン−2−イル)−5−(2−メトキシエチルアミノ)ピラゾール−4−カルボニトリル(36g)を得た。
得られた1−(3−クロロ−4,5,6,7−テトラヒドロピラゾロ[1,5−a]ピ
リジン−2−イル)−5−(2−メトキシエチルアミノ)ピラゾール−4−カルボニトリル(20g)にアセトニトリル(65ml)を加え、そこへトリフルオロ酢酸無水物(14.4g)をゆっくりと滴下した。50℃で10時間攪拌し、反応液に飽和炭酸水素ナトリウム水溶液を加え、酢酸エチルで抽出した。硫酸ナトリウムで乾燥した後、溶媒を減圧濃縮し、得られた粗生成物を再結晶(酢酸エチル/ヘキサン)により精製し、目的物(22.7g)を得た。
1.粉剤
式(I)の化合物 10重量部
タルク 90重量部
を混合しハンマーミルで微粉砕することにより得られる。
式(I)の化合物 10重量部
ポリオキシエチレンアルキルアリールエーテル硫酸塩 22.5重量部
ホワイトカーボン 67.5重量部
を混合し、この混合物をハンマーミルで微粉砕することにより得られる。
式(I)の化合物 10重量部
ポリオキシエチレンアルキルエーテルリン酸塩 10重量部
ベントナイト 5重量部
エチレングリコール 5重量部
水 70重量部
を混合し、湿式粉砕機を用いて粉砕することによりフロアブル剤が得られる。
式(I)の化合物 15重量部
エトキシル化ノニルフェノール 10重量部
シクロヘキサノン 75重量部
を混合することにより乳剤が得られる。
式(I)の化合物 5重量部
リグニンスルホン酸カルシウム 3重量部
ポリカルボン酸塩 3重量部
炭酸カルシウム 89重量部
を混合し、水を加えて混練後押出し造粒する。その後乾燥、整粒することにより粒剤が得られる。
1.水田除草試験
1/10000アールのポットに水田土壌を充填し、適量の水と化学肥料を加えて混練し、ノビエ、コナギ及びホタルイの種子を播種し、水深3cmの湛水状態を保った。
製剤例に準じて調整した表1に示す目的化合物(I)の水和剤を適量の水で希釈し、ノビエ3.5葉期に2.0葉期のイネを移植し、アール当たり所定の薬量となるようにピペットを用いて滴下処理した。
そして平均気温30℃のガラス室で30日間管理した後に、それらの除草効果を調査した。
0(指数):0%〜10%未満(生育抑制率)、
1:10%以上〜20%未満、
2:20%以上〜30%未満、
3:30%以上〜40%未満、
4:40%以上〜50%未満、
5:50%以上〜60%未満、
6:60%以上〜70%未満、
7:70%以上〜80%未満、
8:80%以上〜90%未満、
9:90%以上〜100%未満、
10:100%
対照剤4.63(WO94/08999記載)
1/6000アールのポットに畑土壌を充填し、メヒシバ、シロザ、アオビユの種子を播種して覆土した。
製剤例に準じて調製した表1に示す式(I)の化合物の水和剤を所定の薬量になるように水で希釈し、播種後雑草発生前にアール当たり10リットルの散布水量で各土壌表層に均一に噴霧処理した。
そして平均気温30℃のガラス室で30日間管理した後に、それらの除草効果を調査し
た。
除草効果の評価は、前記試験例1と同様に行った。
その結果を表3に示す。
1/6000アールのポットに培土を充填し、メヒシバ、シロザ、アオビユ、の種子を播種して覆土し、平均気温25℃のガラス室で栽培した。
メヒシバが1.0〜2.0葉期に生育した時期に、製剤例に準じて調製した表1に示す目的化合物(I)の水和剤を所定の薬量になるように水で希釈し、アール当たり15リットルの散布水量で雑草上に均一に噴霧処理した。
そして平均気温25℃のガラス室で3週間管理した後に、それらの除草効果を調査した。
除草効果の評価は前記試験例1と同様に行った。
その結果を表4に示す。
Claims (6)
- 請求項1に記載の化合物の少なくとも1種の除草有効量を含む、除草剤組成物。
- 処方助剤をさらに含む、請求項2に記載の除草剤組成物。
- 請求項1に記載の化合物の少なくとも1種の有効量または請求項2または3に記載の除草剤組成物を、望ましくない植物または望ましくない植生の場所に施用することを含む、望ましくない植物の防除方法。
- 望ましくない植物を防除するための、請求項1に記載の化合物または請求項2または3に記載の除草剤組成物の使用。
- 請求項1に記載の化合物が有用植物の農作物中の望ましくない植物を防除するために使用される、請求項5に記載の使用。
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WO2016117680A1 (ja) * | 2015-01-23 | 2016-07-28 | 協友アグリ株式会社 | 置換ピラゾリルピラゾール誘導体とその除草剤としての使用 |
WO2016117671A1 (ja) * | 2015-01-23 | 2016-07-28 | 協友アグリ株式会社 | 置換ピラゾリルピラゾール誘導体とその除草剤としての使用 |
WO2016117673A1 (ja) * | 2015-01-23 | 2016-07-28 | 協友アグリ株式会社 | 置換ピラゾリルピラゾール誘導体とその除草剤としての使用 |
WO2016117670A1 (ja) * | 2015-01-23 | 2016-07-28 | 協友アグリ株式会社 | 置換ピラゾリルピラゾール誘導体とその除草剤としての使用 |
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JP2016141628A (ja) * | 2015-01-30 | 2016-08-08 | 協友アグリ株式会社 | 除草剤組成物 |
WO2019233372A1 (zh) * | 2018-06-04 | 2019-12-12 | 海利尔药业集团股份有限公司 | 一种取代的吡唑基吡唑磺酰胺类化合物或其作为农药可接受的盐、组合物及其用途 |
CN112341456B (zh) * | 2019-08-07 | 2024-01-05 | 海利尔药业集团股份有限公司 | 一种取代的吡唑基吡唑双酰胺类化合物或其作为农药可接受的盐、组合物及其用途 |
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Publication number | Priority date | Publication date | Assignee | Title |
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WO2016117680A1 (ja) * | 2015-01-23 | 2016-07-28 | 協友アグリ株式会社 | 置換ピラゾリルピラゾール誘導体とその除草剤としての使用 |
WO2016117671A1 (ja) * | 2015-01-23 | 2016-07-28 | 協友アグリ株式会社 | 置換ピラゾリルピラゾール誘導体とその除草剤としての使用 |
WO2016117673A1 (ja) * | 2015-01-23 | 2016-07-28 | 協友アグリ株式会社 | 置換ピラゾリルピラゾール誘導体とその除草剤としての使用 |
WO2016117670A1 (ja) * | 2015-01-23 | 2016-07-28 | 協友アグリ株式会社 | 置換ピラゾリルピラゾール誘導体とその除草剤としての使用 |
US10165779B2 (en) | 2015-01-23 | 2019-01-01 | Kyoyu Agri Co., Ltd. | Substituted pyrazolylpyrazole derivative and use of same as herbicide |
US10165777B2 (en) | 2015-01-23 | 2019-01-01 | Kyoyu Agri Co., Ltd. | Substituted pyrazolylpyrazole derivative and use of same as herbicide |
US10167288B2 (en) | 2015-01-23 | 2019-01-01 | Kyoyu Agri Co., Ltd. | Substituted pyrazolylpyrazole derivative and use of same as herbicide |
US10258042B2 (en) | 2015-01-23 | 2019-04-16 | Kyoyu Agri Co., Ltd. | Substituted pyrazolylpyrazole derivative and use of same as herbicide |
Also Published As
Publication number | Publication date |
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AR097253A1 (es) | 2016-03-02 |
AU2014307436A1 (en) | 2016-02-25 |
IL243615A0 (en) | 2016-02-29 |
US9518061B2 (en) | 2016-12-13 |
RU2016108489A3 (ja) | 2018-05-29 |
CN105492443A (zh) | 2016-04-13 |
BR112016002383A2 (pt) | 2017-08-01 |
EP3034504B1 (en) | 2017-11-08 |
WO2015022925A1 (ja) | 2015-02-19 |
RU2016108489A (ru) | 2017-09-19 |
CN105492443B (zh) | 2017-07-25 |
CA2919471A1 (en) | 2015-02-19 |
PH12016500110A1 (en) | 2016-04-18 |
TWI647218B (zh) | 2019-01-11 |
UA115820C2 (uk) | 2017-12-26 |
RU2661195C2 (ru) | 2018-07-13 |
EP3034504A1 (en) | 2016-06-22 |
KR20160042924A (ko) | 2016-04-20 |
AU2014307436B2 (en) | 2017-12-14 |
MX2016001141A (es) | 2016-04-29 |
US20160159806A1 (en) | 2016-06-09 |
TW201536753A (zh) | 2015-10-01 |
JP6128556B2 (ja) | 2017-05-17 |
EP3034504A4 (en) | 2017-03-22 |
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