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AR102197A1 - COMPOUND OF ARIL SULFONAMIDE OR ITS SALT, AND HERBICIDES CONTAINING IT - Google Patents

COMPOUND OF ARIL SULFONAMIDE OR ITS SALT, AND HERBICIDES CONTAINING IT

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Publication number
AR102197A1
AR102197A1 ARP150103234A ARP150103234A AR102197A1 AR 102197 A1 AR102197 A1 AR 102197A1 AR P150103234 A ARP150103234 A AR P150103234A AR P150103234 A ARP150103234 A AR P150103234A AR 102197 A1 AR102197 A1 AR 102197A1
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AR
Argentina
Prior art keywords
substituted
alkyl
phenyl
cycloalkyl
moiety
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ARP150103234A
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Spanish (es)
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Ishihara Sangyo Kaisha
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Application filed by Ishihara Sangyo Kaisha filed Critical Ishihara Sangyo Kaisha
Publication of AR102197A1 publication Critical patent/AR102197A1/en

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    • AHUMAN NECESSITIES
    • A01AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01NPRESERVATION 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
    • A01N43/00Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/34Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom
    • A01N43/40Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom six-membered rings
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D211/00Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings
    • C07D211/04Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D211/68Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having one double bond between ring members or between a ring member and a non-ring member
    • C07D211/72Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having one double bond between ring members or between a ring member and a non-ring member with hetero atoms or with carbon atoms having three bonds to hetero atoms, with at the most one bond to halogen, directly attached to ring carbon atoms
    • C07D211/74Oxygen atoms
    • C07D211/76Oxygen atoms attached in position 2 or 6

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  • Life Sciences & Earth Sciences (AREA)
  • Organic Chemistry (AREA)
  • Chemical & Material Sciences (AREA)
  • Health & Medical Sciences (AREA)
  • Environmental Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Dentistry (AREA)
  • General Health & Medical Sciences (AREA)
  • Wood Science & Technology (AREA)
  • Zoology (AREA)
  • Plant Pathology (AREA)
  • Pest Control & Pesticides (AREA)
  • Agronomy & Crop Science (AREA)
  • Agricultural Chemicals And Associated Chemicals (AREA)
  • Hydrogenated Pyridines (AREA)
  • Nitrogen Condensed Heterocyclic Rings (AREA)
  • Plural Heterocyclic Compounds (AREA)

Abstract

Se proporciona un herbicida que exhibe actividades herbicidas a plantas indeseables. Reivindicación 1: Un compuesto de aril sulfonamida representado por la fórmula (1) o su sal, donde, R¹ es haloalquilo C₁₋₆; R² es un átomo de hidrógeno, alquilo C₁₋₆, haloalquilo C₁₋₆, alquenilo C₃₋₆, haloalquenilo C₃₋₆, alquinilo C₃₋₆, haloalquinilo C₃₋₆, alcoxi C₁₋₆alquilo C₁₋₆, alquilcarboniloxi C₁₋₆alquilo C₁₋₆, cicloalquilcarboniloxi C₃₋₇alquilo C₁₋₆, alcoxicarboniloxi C₁₋₆alquilo C₁₋₆, cicloalquilcarboniloxi C₃₋₇alquilo C₁₋₆, mono(alquil C₁₋₆)aminocarboniloxi-alquilo C₁₋₆, di(alquil C₁₋₆)aminocarboniloxi-alquilo C₁₋₆, (fenil)aminocarboniloxi-alquilo C₁₋₆ (el resto fenilo puede estar sustituido por J), (fenil)(alquil C₁₋₆)aminocarboniloxi-alquilo C₁₋₆ (el resto fenilo puede estar sustituido por J), fenilalquilo C₁₋₆ (el resto fenilo puede estar sustituido por J), fenilcarboniloxi-alquilo C₁₋₆ (el resto fenilo puede estar sustituido por J), grupo heterocíclico-carboniloxi-alquilo C₁₋₆ (el resto heterocíclico puede estar sustituido por J), fenoxicarboniloxi-alquilo C₁₋₆ (el resto fenilo puede estar sustituido por J), alquilcarbonilo C₁₋₁₂, haloalquilcarbonilo C₁₋₁₂, carbonilo C₂₋₆, halocarbonilo C₂₋₆, cicloalquilcarbonilo C₃₋₇, cicloalquil C₃₋₇alquilcarbonilo C₁₋₆, alcoxicarbonilo C₁₋₁₂, haloalcoxicarbonilo C₁₋₁₂, (cicloalquiloxi C₃₋₇)carbonilo, (cicloalquiloxi C₃₋₇alquilo C₁₋₆ sustituido)carbonilo, (cicloalquiloxi C₃₋₇haloalquilo C₁₋₆ sustituido)carbonilo, alqueniloxicarbonilo C₃₋₆, haloalqueniloxicarbonilo C₃₋₆, alquiniloxicarbonilo C₃₋₆, haloalquiniloxicarbonilo C₃₋₆, alquiltiocarbonilo C₁₋₆, haloalquiltiocarbonilo C₁₋₆, alcoxi C₁₋₆alquilcarbonilo C₁₋₆, alcoxicarbonilo C₁₋₆alquilcarbonilo C₁₋₆, alcoxi C₁₋₆alcoxicarbonilo C₁₋₆, alcoxi C₁₋₆alquiltiocarbonilo C₁₋₆, alquiltio C₁₋₆alcoxicarbonilo C₁₋₆, alquilsulfinilo C₁₋₆alcoxicarbonilo C₁₋₆, alquilsulfonilo C₁₋₆alcoxicarbonilo C₁₋₆, mono(alquil C₁₋₆)aminocarbonilo, mono(haloalquil C₁₋₆)aminocarbonilo, di(alquil C₁₋₆)aminocarbonilo, di(haloalquil C₁₋₆)aminocarbonilo, fenilcarbonilo (el resto fenilo puede estar sustituido por J), fenil-alquenilcarbonilo C₂₋₆ (el resto fenilo puede estar sustituido por J), fenil-alcoxicarbonilo C₁₋₆ (el resto fenilo puede estar sustituido por J), fenil-haloalcoxicarbonilo C₁₋₆ (el resto fenilo puede estar sustituido por J), fenoxicarbonilo (el resto fenilo puede estar sustituido por J), fenoxi-alcoxicarbonilo C₁₋₆ (el resto fenilo puede estar sustituido por J), grupo heterocíclico-carbonilo (el resto heterocíclico puede estar sustituido por J), alcoxioxalilo C₁₋₆, alquilsulfonilo C₁₋₆, haloalquilsulfonilo C₁₋₆, cicloalquilsulfonilo C₃₋₇, fenilsulfonilo (el resto fenilo puede estar sustituido por J) o grupo heterocíclico-sulfonilo (el resto heterocíclico puede estar sustituido por J); R³ es halógeno, alquilo C₁₋₆, haloalquilo C₁₋₆, alcoxi C₁₋₆ o haloalcoxi C₁₋₆; cada uno de R⁴ y R⁵ que son independientes uno del otro, es un átomo de hidrógeno, alquilo C₁₋₆ o haloalquilo C₁₋₆; T es halógeno, alquilo C₁₋₆, haloalquilo C₁₋₆, alquenilo C₂₋₆, alquinilo C₂₋₆, cicloalquilo C₃₋₇, cicloalquilo C₃₋₇ sustituido por halógeno, -OH, alcoxi C₁₋₆, haloalcoxi C₁₋₆, alquilcarboniloxi C₁₋₆, alquiltio C₁₋₆, haloalquiltio C₁₋₆, alquilsulfinilo C₁₋₆, haloalquilsulfinilo C₁₋₆, alquilsulfonilo C₁₋₆, haloalquilsulfonilo C₁₋₆, fenilo (el resto fenilo puede estar sustituido por J) o fenilalquilo C₁₋₆ (el resto fenilo puede estar sustituido por J); W es O ó S; X es -O-Y, -S-Z¹, -SO-Z² o -SO₂-Z³; Y es alquilo C₁₋₆ sustituido por A, alquilcarbonilo C₁₋₆ sustituido por A, alcoxicarbonilo C₁₋₆, haloalcoxicarbonilo C₁₋₆, alquiltiocarbonilo C₁₋₆, haloalquiltiocarbonilo C₁₋₆, alquenilo C₃₋₆, haloalquenilo C₃₋₆, alquinilo C₃₋₆, haloalquinilo C₃₋₆, cicloalquilo C₃₋₇, cicloalquilo C₃₋₇ sustituido por alquilo C₁₋₆, cicloalquilo C₃₋₇ sustituido por halo de alquilo C₁₋₆, cicloalquilo C₃₋₇ sustituido por alcoxi C₁₋₆ o un grupo heterocíclico (el resto heterocíclico puede estar sustituido por J); Z¹ es H, hidroxialquilo C₁₋₆, alcoxi C₁₋₆alquilo C₁₋₆, haloalcoxi C₁₋₆alquilo C₁₋₆, cicloalquilo C₃₋₇, cicloalquilo C₃₋₇ sustituido por alquilo C₁₋₆ o cicloalquilo C₃₋₇ sustituido por haloalquilo C₁₋₆; Z² es alquilo C₁₋₆, haloalquilo C₁₋₆, hidroxialquilo C₁₋₆, alcoxi C₁₋₆alquilo C₁₋₆, haloalcoxi C₁₋₆alquilo C₁₋₆, cicloalquilo C₃₋₇, cicloalquilo C₃₋₇ sustituido por alquilo C₁₋₆, cicloalquilo C₃₋₇ sustituido por halo alquilo C₁₋₆ o fenilo (el resto fenilo puede estar sustituido por J); Z³ es hidroxialquilo C₁₋₆, alcoxi C₁₋₆alquilo C₁₋₆, haloalcoxi C₁₋₆alquilo C₁₋₆, cicloalquilo C₃₋₇, cicloalquilo C₃₋₇ sustituido por alquilo C₁₋₆, cicloalquilo C₃₋₇ sustituido por halo alquilo C₁₋₆ o fenilo (el resto fenilo puede estar sustituido por J); A es -OH, alcoxi C₁₋₆, haloalcoxi C₁₋₆, alcoxi C₁₋₆alcoxi C₁₋₆, haloalcoxi C₁₋₆alcoxi C₁₋₆, alquiltio C₁₋₆, haloalquiltio C₁₋₆, alquilsulfinilo C₁₋₆, haloalquilsulfinilo C₁₋₆, alquilsulfonilo C₁₋₆, haloalquilsulfonilo C₁₋₆, mono(alquil C₁₋₆)amino, di(alquil C₁₋₆)amino, cicloalquilo C₃₋₇, cicloalquilo C₃₋₇ sustituido por alquilo C₁₋₆, cicloalquilo C₃₋₇ sustituido por halo de alquilo C₁₋₆, cicloalquilo C₃₋₇ sustituido por alcoxi C₁₋₆, fenilo (el resto fenilo puede estar sustituido por J), fenilalcoxi C₁₋₆ (el resto fenilo puede estar sustituido por J), fenoxi (el resto fenilo puede estar sustituido por J), un grupo heterocíclico (el resto heterocíclico puede estar sustituido por J), grupo heterocíclico-oxi (el resto heterocíclico puede estar sustituido por J), bicicloalquilo C₆₋₁₀, alquilo-alquilcarbonilo C₁₋₆, alcoxicarbonilo C₁₋₆, carboxi, ciano o nitro; J es halógeno, alquilo C₁₋₆, haloalquilo C₁₋₆, alquenilo C₂₋₆, haloalquenilo C₂₋₆, alquinilo C₂₋₆, haloalquinilo C₂₋₆, cicloalquilo C₃₋₇, cicloalquilo C₃₋₇ sustituido por halógeno, -OH, alcoxi C₁₋₆, haloalcoxi C₁₋₆, alquiltio C₁₋₆, haloalquiltio C₁₋₆, alquilsulfinilo C₁₋₆, haloalquilsulfinilo C₁₋₆, alquilsulfonilo C₁₋₆, haloalquilsulfonilo C₁₋₆, alquilcarbonilo C₁₋₆, haloalquilcarbonilo C₁₋₆, carboxi, alcoxicarbonilo C₁₋₆, haloalcoxicarbonilo C₁₋₆, amino, mono(alquil C₁₋₆)amino, mono(haloalquil C₁₋₆)amino, di(alquil C₁₋₆)amino, di(haloalquil C₁₋₆)amino, ciano o nitro; m es un número entero de 0 a 4; n es un número entero de 0 a 5.A herbicide is provided that exhibits herbicidal activities to undesirable plants. Claim 1: An aryl sulfonamide compound represented by the formula (1) or its salt, wherein, R¹ is C₁₋₆ haloalkyl; R² is a hydrogen atom, C₁₋₆ alkyl, C₁₋₆ haloalkyl, C₃₋₆ alkenyl, C₃₋₆ haloalkenyl, C₃₋₆ alkynyl, C₃₋₆ haloalkynyl, C₁₋₆alkoxyC₁₋₆alkyl, C₁₋₆alkylcarbonyloxy ₋₆, C₃₋₇ cycloalkylcarbonyloxy, C₁₋₆alkoxycarbonyloxyC₁₋₆, C ciclo cycloalkylcarbonyloxy, mono (C₁₋₆ alkyl) aminocarbonyloxy-C₁₋₆ alkyl, di (C₁₋₆ alkyl) aminocarbonyloxy- C₁₋₆ alkyl, (phenyl) aminocarbonyloxy-C₁₋₆ alkyl (the phenyl moiety may be substituted by J), (phenyl) (C₁₋₆ alkyl) aminocarbonyloxy-C alquilo alkyl (the phenyl moiety may be substituted by J) , C₁₋₆ phenylalkyl (the phenyl moiety may be substituted by J), phenylcarbonyloxy-C₁₋₆ alkyl (the phenyl moiety may be substituted by J), heterocyclic-carbonyloxy-C₁₋₆ alkyl group (the heterocyclic moiety may be substituted by J), phenoxy carbonyloxy-C₁₋₆ alkyl (the phenyl moiety may be substituted by J), C₁₋₁₂ alkylcarbonyl, C₁₋₁₂ haloalkylcarbonyl, C₂₋₆ carbonyl, C₃₋₇ halocarbonyl, C₃₋₇ cycloalkylcarbonyl, C₃₋₇ cycloalkylcarbonyl, C₁₋₁₂ alkoxycarbonyl, C₁₋₁₂ haloalkoxycarbonyl, (C₃₋₇ cycloalkyloxy), (substituted C₁₋₆ cycloalkyloxy) carbonyl, (C₁₋₆ substituted C₃₋₇haloalkyl cycloalkyloxy) carbonyl, C₃₋₆ alkenyloxycarbonyl, C₃₋ haloalkenyloxycarbonyl ₆, C₃₋₆ alkyloxycarbonyl, C₃₋₆ haloalkyloxycarbonyl, C₁₋₆ alkylthiocarbonyl, C₁₋₆ haloalkylthiocarbonyl, C₁₋₆alkylcarbonyl C₁₋₆, C alcoalkoxycarbonyl C₁₋₆, C₁₋₆alkoxycarbonyl alkoxy, C₁₋₆alkylthiocarbonyl alkoxy C₁₋₆, Ciltalkoxycarbonyl C₁₋₆ alkylthio, C₁₋₆alkoxycarb alkylsulfinyl C₁₋₆ onyl, C₁₋₆alkoxycarbonyl C₁₋₆ alkylsulfonyl, mono (C₁₋₆ alkyl) aminocarbonyl, mono (haloalkyl Cal) aminocarbonyl, di (C₁₋₆alkyl) aminocarbonyl, di (haloalkyl C₁₋₆) aminocarbonyl, phenylcarbonyl (the phenyl moiety may be substituted by J), phenyl-alkenylcarbonyl C₂₋₆ (the phenyl moiety may be substituted by J), phenyl-alkoxycarbonyl C₁₋₆ (the phenyl moiety may be substituted by J), phenyl-haloalkoxycarbonyl C₁₋ ₆ (the phenyl moiety can be substituted by J), phenoxycarbonyl (the phenyl moiety can be substituted by J), phenoxy-C-alkoxycarbonyl (the phenyl moiety can be substituted by J), heterocyclic-carbonyl group (the heterocyclic moiety can be substituted by J), C₁₋₆ alkoxyoxalyl, C₁₋₆ alkylsulfonyl, C₁₋₆ haloalkylsulfonyl, C₃₋₇ cycloalkylsulfonyl, phenylsulfonyl (the phenyl moiety may be substituted by J) or heterocyclic sulfonyl group (the rest heterocyclic may be substituted by J); R³ is halogen, C₁₋₆ alkyl, C₁₋₆ haloalkyl, C₁₋₆ alkoxy or C₁₋₆ haloalkoxy; each of R⁴ and R⁵ that are independent of each other, is a hydrogen atom, C₁₋₆ alkyl or C₁₋₆ haloalkyl; T is halogen, C₁₋₆ alkyl, C₁₋₆ haloalkyl, C₂₋₆ alkenyl, C₂₋₆ alkynyl, C₃₋₇ cycloalkyl, halogen substituted C₃₋₇ cycloalkyl, -OH, C₁₋₆ alkoxy, C₁₋₆ haloalkoxy, C₁₋₆ alkylcarbonyloxy, C₁₋₆ alkylthio, C₁₋₆ haloalkylthio, C₁₋₆ alkylsulfinyl, C₁₋₆ haloalkylsulfinyl, C₁₋₆ alkylsulfonyl, C₁₋₆ haloalkylsulfonyl, phenyl (the phenyl moiety may be substituted by J) or C₁₋ phenylalkyl ₆ (the phenyl moiety may be substituted by J); W is O or S; X is -O-Y, -S-Z¹, -SO-Z² or -SO₂-Z³; Y is C₁₋₆ alkyl substituted by A, C₁₋₆ alkylcarbonyl substituted by A, C₁₋₆ alkoxycarbonyl, C₁₋₆ haloalkoxycarbonyl, C₁₋₆ alkylthiocarbonyl, C₁₋₆ haloalkylthiocarbonyl, C₃₋₆ alkenyl, C₃₋₆ haloalkenyl, C₃ alkynyl ₋₆, C₃₋₆ haloalkynyl, C₃₋₇ cycloalkyl, C₃₋₇ cycloalkyl substituted by C₁₋₆ alkyl, C₃₋₇ cycloalkyl substituted by C₁₋₆ alkyl halo, C₃₋₇ cycloalkyl substituted by C₁₋₆ alkoxy or a group heterocyclic (the heterocyclic moiety may be substituted by J); Z¹ is H, C₁₋₆ hydroxyalkyl, C₁₋₆alkyl C₁₋₆alkoxy, C₁₋₆alkyl haloalkoxy, C₃₋₇ cycloalkyl, C ciclo cycloalkyl substituted by C₁₋₆alkyl or C₃₋₇alkyl substituted by C₁₋alkyl ₆; Z² is C₁₋₆ alkyl, C₁₋₆ haloalkyl, C₁₋₆ hydroxyalkyl, C₁₋₆alkyl alkoxy, C₁₋₆alkyl haloalkoxy, C ciclo cycloalkyl, C₃₋₇ cycloalkyl substituted by C₁₋₆ alkyl, cycloalkyl C₃₋₇ substituted by halo C₁₋₆ alkyl or phenyl (the phenyl moiety may be substituted by J); Z³ is C₁₋₆ hydroxyalkyl, C₁₋₆alkyl C₁₋₆alkoxy, C₁₋₆alkyl haloalkoxy, C₃₋₇cycloalkyl, C₃₋₇ cycloalkyl substituted by C₁₋₆alkyl, C₃₋₇cycloalkyl substituted by haloC₁₋₆alkyl or phenyl (the phenyl moiety may be substituted by J); A is -OH, C₁₋₆ alkoxy, C₁₋₆ haloalkoxy, C₁₋₆alkoxy C₁₋₆ alkoxy, C₁₋₆alkoxy C₁₋₆ haloalkoxy, C₁₋₆ alkylthio, C₁₋₆ haloalkylthio, C₁₋₆ alkylsulfinyl, C₁₋₆ haloalkylsulfinyl , C₁₋₆ alkyl sulfonyl, C₁₋₆ haloalkylsulfonyl, mono (C₁₋₆ alkyl) amino, di (C₁₋₆ alkyl) amino, C₃₋₇ cycloalkyl, C₃₋₇ cycloalkyl substituted by C₁₋₆ alkyl, substituted C₃₋₇ cycloalkyl by halo of C alquilo alkyl, C₃₋₇ cycloalkyl substituted by C₁₋₆ alkoxy, phenyl (the phenyl moiety may be substituted by J), phenylalkoxy C₁₋₆ (the phenyl moiety may be substituted by J), phenoxy (the rest phenyl may be substituted by J), a heterocyclic group (the heterocyclic moiety may be substituted by J), heterocyclic-oxy group (the heterocyclic moiety may be substituted by J), bicycloalkyl C₆₋₁₀, alkyl-alkylcarbonyl C₁₋₆, alkoxycarbonyl C₁₋₆, c arboxy, cyano or nitro; J is halogen, C₁₋₆ alkyl, C₁₋₆ haloalkyl, C₂₋₆ alkenyl, C₂₋₆ haloalkenyl, C₂₋₆ alkynyl, C₂₋₆ haloalkynyl, C₃₋₇ cycloalkyl, halogen substituted C₃₋₇ cycloalkyl, -OH, C₁₋₆ alkoxy, C₁₋₆ haloalkoxy, C₁₋₆ alkylthio, C₁₋₆ haloalkylthio, C₁₋₆ alkylsulfinyl, C₁₋₆ haloalkylsulfinyl, C₁₋₆ alkylsulfonyl, C₁₋₆ haloalkylsulfonyl, C₁₋₆ alkylcarbonyl, C₁₋₆ haloalkylcarbonyl, carboxy, C₁₋₆ alkoxycarbonyl, C₁₋₆ haloalkoxycarbonyl, amino, mono (C₁₋₆ alkyl) amino, mono (haloCquil alkyl) amino, di (C₁₋₆ alkyl) amino, di (haloalkylC₁₋₆) amino, cyano or nitro; m is an integer from 0 to 4; n is an integer from 0 to 5.

ARP150103234A 2014-10-10 2015-10-07 COMPOUND OF ARIL SULFONAMIDE OR ITS SALT, AND HERBICIDES CONTAINING IT AR102197A1 (en)

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AU2018210807B2 (en) 2017-01-20 2021-08-26 Hokko Chemical Industry Co., Ltd. Isoxazolin-5-one derivative and herbicide containing same as active ingredient
US20210309619A1 (en) 2018-07-24 2021-10-07 Hokko Chemical Industry Co., Ltd. Isoxazolin-5-one derivatives and herbicides containing the same as active ingredients
WO2021100745A1 (en) * 2019-11-21 2021-05-27 日本曹達株式会社 Oxadiazole compound and germicide for agricultural and horticultural use
EP4530282A1 (en) 2022-04-28 2025-04-02 Sds Biotech K.K. Haloalkyl sulfone anilide compound and herbicide containing same

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JP2000119250A (en) * 1998-08-11 2000-04-25 Takeda Chem Ind Ltd Cyclic amide compound, its production, intermediate and herbicide
EP1852425A1 (en) * 2005-02-24 2007-11-07 Nihon Nohyaku Co., Ltd. Novel haloalkylsulfonanilide derivative, herbicide, and method of use thereof
KR101667063B1 (en) * 2008-09-02 2016-10-17 닛산 가가쿠 고교 가부시키 가이샤 Ortho-substituted haloalkylsulfonanilide derivative and herbicide
WO2010119906A1 (en) * 2009-04-14 2010-10-21 日産化学工業株式会社 Haloalkylsulfonanilide derivative
GB201121314D0 (en) * 2011-12-09 2012-01-25 Syngenta Ltd Herbicidal compositions
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