AR120168A1 - ALKHENAMIDE COMPOUND AND APPLICATION THEREOF - Google Patents

ALKHENAMIDE COMPOUND AND APPLICATION THEREOF

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Publication number
AR120168A1
AR120168A1 ARP200102772A ARP200102772A AR120168A1 AR 120168 A1 AR120168 A1 AR 120168A1 AR P200102772 A ARP200102772 A AR P200102772A AR P200102772 A ARP200102772 A AR P200102772A AR 120168 A1 AR120168 A1 AR 120168A1
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AR
Argentina
Prior art keywords
alkyl
heteroatoms
alkoxy
cycloalkyl
haloalkyl
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ARP200102772A
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Spanish (es)
Inventor
Bing Sun
Huibin Yang
Hongjuan Ma
Junwu Ying
Dongliang Cui
Bo Qin
Shuang Liang
Gang Wang
Zhengmao Lu
Fan Zhang
Lin Chen
Heying Pei
Yan Cheng
Mingxin Wang
Bin Li
Original Assignee
Shenyang Sinochem Agrochemicals R & D Co Ltd
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Application filed by Shenyang Sinochem Agrochemicals R & D Co Ltd filed Critical Shenyang Sinochem Agrochemicals R & D Co Ltd
Publication of AR120168A1 publication Critical patent/AR120168A1/en

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    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D257/00Heterocyclic compounds containing rings having four nitrogen atoms as the only ring hetero atoms
    • C07D257/02Heterocyclic compounds containing rings having four nitrogen atoms as the only ring hetero atoms not condensed with other rings
    • C07D257/04Five-membered rings
    • C07D257/06Five-membered rings with nitrogen atoms directly attached to the ring carbon atom
    • 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
    • A01N43/713Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with four or more nitrogen atoms as the only ring hetero atoms
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D401/00Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
    • C07D401/02Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
    • C07D401/12Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings linked by a chain containing hetero atoms as chain links
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D405/00Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
    • C07D405/02Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
    • C07D405/12Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings linked by a chain containing hetero atoms as chain links

Abstract

Un compuesto alquenamida y la aplicación como herbicida de una sal aceptable en la agricultura. El compuesto responde a la fórmula (1). En la memoria descriptiva se define cada sustituyente de la fórmula (1). En el compuesto de fórmula (1) tiene una excelente actividad herbicida y se puede utilizar para el control de malezas en la agricultura. Reivindicación 1: Un compuesto amida que contiene alqueno, caracterizado porque el compuesto responde a la fórmula (1) donde: X¹ y X³ se seleccionan en forma independiente entre hidrógeno, ciano, nitro, halógeno, C₁₋₆ alquilsulfonilo, C₁₋₆ haloalquilsulfonilo, C₁₋₆ alquilsulfinilo, C₁₋₆ haloalquilsulfinilo, C₁₋₆ alquiltio, C₁₋₆ haloalquiltio, C₁₋₆ alquilo, C₁₋₆ haloalquilo, C₁₋₆ alcoxi, C₁₋₆ haloalcoxi, C₁₋₆ alcoxiC₁₋₃ alquilo, C₁₋₆ alcoxi C₁₋₃alcoxi, C₁₋₆ alcoxiC₁₋₃ alcoxiC₁₋₃ alquilo, C₃₋₆ cicloalquilo, C₃₋₆ cicloalquiloC₁₋₃ alquilo, C₃₋₆ cicloalquiloC₁₋₃ alcoxi, C₃₋₆ cicloalquiloxi, C₂₋₆ alquenilo, C₂₋₆ alquinilo, fenilo, C₂₋₆ alquenilsulfonilo, C₂₋₆ alquinilsulfonilo, fenilsulfonilo, C₂₋₆ alqueniloxi, C₂₋₆ alquiniloxi, feniloxi, C₂₋₆ alqueniltio, C₂₋₆ alquiniltio, feniltio, un heterociclo alifático de 5 - 7 miembros que contiene 1 - 4 heteroátomos, un heterociclo aromático de 5 - 7 miembros que contiene 1 - 4 heteroátomos, un C₁₋₆ alquilo heterocíclico alifático de 5 - 7 miembros que contiene 1 - 4 heteroátomos o un C₁₋₆ alquilo heterocíclico aromático de 5 - 7 miembros que contiene 1 - 4 heteroátomos; los hidrógenos del fenilo, el heterociclo alifático y el heterociclo aromático pueden sustituirse por uno o más sustituyentes seleccionados entre nitro, halógeno, C₁₋₆ alquilo, C₁₋₆ haloalquilo, C₁₋₆ alcoxi, C₁₋₆ haloalcoxi o C₃₋₆ cicloalquilo; W se selecciona entre N o CX²; X² se selecciona entre hidrógeno, ciano, nitro, halógeno, C₁₋₆ alquilo, C₁₋₆ haloalquilo, C₃₋₆ cicloalquilo, C₃₋₆ cicloalquiloC₁₋₆ alquilo, C₃₋₆ halocicloalquiloC₁₋₆ alquilo, Y¹-oxi, Y¹-tio, Y¹Y²-amino, Y¹-sulfinilo, Y¹-sulfonilo, Y¹-oxiC₁₋₆ alquilo, Y¹-tioC₁₋₆ alquilo, Y¹Y²-aminoC₁₋₆ alquilo, Y¹-sulfiniloC₁₋₆ alquilo, Y¹-sulfoniloC₁₋₆ alquilo, C(O)Y¹, C(O)OY¹, OC(O)OY¹, N(Y¹)C(O)OY², C(O)N(Y¹)Y², N(Y¹)C(O)N(Y¹)Y², OC(O)N(Y¹)Y², C(O)N(Y¹)OY², N(Y¹)S(O)₂Y², N(Y¹)C(O)Y², OS(O)₂Y¹, CH=NOY¹, C₁₋₆ alquil-CH=NOY¹, C₁₋₆ alquil-O-N=C(Y¹)Y², fenilo, un heterociclo alifático de 5 - 7 miembros que contiene 1 - 4 heteroátomos, un heterociclo aromático de 5 - 7 miembros que contiene 1 - 4 heteroátomos, un C₁₋₆ alquilo heterocíclico alifático de 5 - 7 miembros que contiene 1 - 4 heteroátomos o un C₁₋₆ alquilo heterocíclico aromático de 5 - 7 miembros que contiene 1 - 4 heteroátomos; los hidrógenos del fenilo, el heterociclo alifático, y el heterociclo aromático pueden sustituirse por uno o más sustituyentes seleccionados entre nitro, halógeno, C₁₋₆ alquilo, C₁₋₆ haloalquilo, C₁₋₆ alcoxi, C₁₋₆ haloalcoxi, C₃₋₆ cicloalquilo, C₃₋₆ cicloalcoxi, C₂₋₆ alquenilo, C₂₋₆ alquinilo, fenilo o halofenilo; Y¹ y Y² se seleccionan en forma independiente entre C₁₋₆ alquilo, C₁₋₆ haloalquilo, C₃₋₆ cicloalquilo, C₃₋₆ cicloalquiloC₁₋₆ alquilo, C₁₋₆ alcoxiC₁₋₆ alquilo, fenilo, un heterociclo alifático de 5 - 7 miembros que contiene 1 - 4 heteroátomos, un heterociclo aromático de 5 - 7 miembros que contiene 1 - 4 heteroátomos, un C₁₋₆ alquilo heterocíclico alifático de 5 - 7 miembros que contiene 1 - 4 heteroátomos o un C₁₋₆ alquilo heterocíclico aromático de 5 - 7 miembros que contiene 1 - 4 heteroátomos; los hidrógenos del fenilo, el heterociclo alifático, y el heterociclo aromático pueden sustituirse por uno o más sustituyentes seleccionados entre nitro, halógeno, C₁₋₆ alquilo, C₁₋₆ haloalquilo, C₁₋₆ alcoxi, C₁₋₆ haloalcoxi, C₃₋₆ cicloalquilo, C₃₋₆ cicloalcoxi, C₂₋₆ alquenilo, C₂₋₆ alquinilo, fenilo o halofenilo; Z se selecciona entre los grupos Z¹ de fórmula (2) y Z²; Z² se selecciona entre C₃₋₈ cicloalquenilo; los hidrógenos del anillo pueden sustituirse por sustituyentes seleccionados entre nitro, halógeno, C₁₋₆ alquilo, C₁₋₆ haloalquilo, C₁₋₆ alcoxi, C₁₋₆ haloalcoxi, C₁₋₆ alquenilo o C₃₋₆ cicloalquilo; Q se selecciona entre los grupos Q¹, Q², Q³, Q⁴, Q⁵ y Q⁶ del grupo de fórmulas (3); R¹ a R⁵ se seleccionan en forma independiente entre hidrógeno, hidroxilo, ciano, nitro, halógeno, fenilo, C₁₋₆ alquilo, C₁₋₆ haloalquilo, C₂₋₆ alquenilo, C₂₋₆ haloalquenilo, C₂₋₆ alquinilo, C₂₋₆ haloalquinilo, C₁₋₆ alcoxi, C₁₋₆ haloalcoxi, C₁₋₆ alquiltio o benciloxi, donde R¹ y R² pueden formar un anillo benceno, un heterociclo alifático de 5 - 7 miembros que contiene 1 - 4 heteroátomos o un heterociclo aromático de 5 - 7 miembros que contiene 1 - 4 heteroátomos junto con los átomos de carbono del anillo benceno conectado; R² y R³ pueden formar un anillo benceno, un heterociclo alifático de 5 - 7 miembros que contiene 1 - 4 heteroátomos o un heterociclo aromático de 5 - 7 miembros que contiene 1 - 4 heteroátomos junto con los átomos de carbono del anillo benceno conectado; R⁶, R⁷ y R⁸ se seleccionan en forma independiente entre hidrógeno, C₁₋₆ alquilo, C₁₋₆ haloalquilo, C₃₋₆ cicloalquilo, C₃₋₆ cicloalquilo C₁₋₆ alquilo, C₂₋₆ alquenilo, C₂₋₆ alquinilo o fenilo; R⁹, R¹⁰, y R¹¹ se seleccionan en forma independiente entre hidrógeno, halógeno, ciano, nitro, C₁₋₆ alquilsulfonilo, C₁₋₆ haloalquilsulfonilo, C₁₋₆ alquilsulfinilo, C₁₋₆ haloalquilsulfinilo, C₁₋₆ alquiltio, C₁₋₆ haloalquiltio, C₁₋₆ alquilo, C₁₋₆ haloalquilo, C₁₋₆ alcoxi, C₁₋₆ haloalcoxi, C₁₋₃ alcoxiC₁₋₃ alquilo, C₁₋₆ alcoxiC₁₋₃ alcoxi, C₁₋₆ alcoxiC₁₋₃ alcoxiC₁₋₃ alquilo, C₃₋₆ cicloalquilo, C₃₋₆ cicloalquiloC₁₋₃ alquilo, C₃₋₆ cicloalquiloC₁₋₃ alcoxi o C₃₋₆ cicloalquiloxi; un estereoisómero del compuesto de la fórmula (1) precedente; o el compuesto de la fórmula (1) y una sal aceptable para uso en agricultura del isómero.An alkenamide compound and the application as herbicide of an agriculturally acceptable salt. The compound responds to formula (1). Each substituent of the formula (1) is defined in the specification. In the compound of formula (1) it has excellent herbicidal activity and can be used for weed control in agriculture. Claim 1: An amide compound containing alkene, characterized in that the compound responds to formula (1) where: X¹ and X³ are independently selected from hydrogen, cyano, nitro, halogen, C₁₋₆ alkylsulfonyl, C₁₋₆ haloalkylsulfonyl, C₁₋₆ alkylsulfinyl, c₁₋₆ haloalkylsulfinyl, c₁₋₆ alkylthio, c₁₋₆ haloalkylthio, c₁₋₆ alkyl, c₁₋₆ haloalkyl, c₁₋₆ alkoxy, c₁₋₆ haloalkoxy, c₁₋₆ alkoxy alkyl, c₁₋ ₆ C₁₋₃alcoxy alkoxy, c₁₋₆ alcoxican alkoxy alkyl, c₃₋₆ cycloalkyl, c₃₋₆ cycloalkylocyl alkyl, c₃₋₆ cycloalkylocyl, c₋₆ α, c₋₋₋ ₆ alkynyl, phenyl, C₂₋₆ alkenylsulfonyl, C₂₋₆ alkynylsulfonyl, phenylsulfonyl, C₂₋₆ alkenyloxy, C₂₋₆ alkynyloxy, phenyloxy, C₂₋₆ alkenylthio, C₂₋₆ alkynylthio, phenylthio, a hetero5-membered aliphatic contains 1-4 heteroatoms, a 5-7 membered aromatic heterocycle containing 1-4 heteroatoms, a 5-7 membered aliphatic C₁₋₆ alkyl heterocyclic q ue containing 1-4 heteroatoms or a 5-7 membered C₁₋₆ aromatic heterocyclic alkyl containing 1-4 heteroatoms; the hydrogens of the phenyl, aliphatic heterocycle, and aromatic heterocycle may be substituted by one or more substituents selected from nitro, halogen, C₁₋₆ alkyl, C₁₋₆ haloalkyl, C₁₋₆ alkoxy, C₁₋₆ haloalkoxy, or C₃₋₆ cycloalkyl; W is selected from N or CX²; X² is selected from hydrogen, cyano, nitro, halogen, C₁₋₆ alkyl, C₁₋₆ haloalkyl, C₃₋₆ cycloalkyl, C₃₋₆ cycloalkyl, C₁₋₆ alkyl, C₃₋₆ halocycloalkyl, C₁₋₆ alkyl, Y¹-oxy, Y¹-thio C( O)Y¹, C(O)OY¹, OC(O)OY¹, N(Y¹)C(O)OY², C(O)N(Y¹)Y², N(Y¹)C(O)N(Y¹)Y², OC(O)N(Y¹)Y², C(O)N(Y¹)OY², N(Y¹)S(O)₂Y², N(Y¹)C(O)Y², OS(O)₂Y¹, CH=NOY¹, C₁₋₆ alkyl-CH=NOY¹, C₁₋₆ alkyl-O-N=C(Y¹)Y², phenyl, a 5-7 membered aliphatic heterocycle containing 1-4 heteroatoms, a 5-7 membered aromatic heterocycle containing 1 - 4 heteroatoms, a C₁₋₆ 5-7 membered aliphatic heterocyclic alkyl containing 1-4 heteroatoms or a 5-7 membered C₁₋₆ aromatic heterocyclic alkyl containing 1-4 heteroatoms; the hydrogens of the phenyl, aliphatic heterocycle, and aromatic heterocycle may be substituted by one or more substituents selected from nitro, halogen, C₁₋₆ alkyl, C₁₋₆ haloalkyl, C₁₋₆ alkoxy, C₁₋₆ haloalkoxy, C₃₋₆ cycloalkyl , C₃₋₆ cycloalkoxy, C₂₋₆ alkenyl, C₂₋₆ alkynyl, phenyl or halophenyl; Y¹ and Y² are independently selected from C₁₋₆ alkyl, C₁₋₆ haloalkyl, C₃₋₆ cycloalkyl, C₃₋₆ cycloalkyl, C₁₋₆ alkyl, C₁₋₆ alkoxy, C₁₋₆ alkyl, phenyl, a 5-7 membered aliphatic heterocycle containing 1-4 heteroatoms, a 5-7 membered aromatic heterocycle containing 1-4 heteroatoms, a 5-7 membered aliphatic C₁₋₆ alkyl heterocyclic containing 1-4 heteroatoms, or a 5-membered aromatic C₁₋₆ alkyl heterocyclic - 7 members containing 1-4 heteroatoms; the hydrogens of the phenyl, aliphatic heterocycle, and aromatic heterocycle may be substituted by one or more substituents selected from nitro, halogen, C₁₋₆ alkyl, C₁₋₆ haloalkyl, C₁₋₆ alkoxy, C₁₋₆ haloalkoxy, C₃₋₆ cycloalkyl , C₃₋₆ cycloalkoxy, C₂₋₆ alkenyl, C₂₋₆ alkynyl, phenyl or halophenyl; Z is selected from the groups Z¹ of formula (2) and Z²; Z² is selected from C₃₋₈ cycloalkenyl; ring hydrogens may be replaced by substituents selected from nitro, halogen, C 146 alkyl, C 146 haloalkyl, C 16 alkoxy, C 16 haloalkoxy, C 16 alkenyl, or C 33 cycloalkyl; Q is selected from the groups Q¹, Q², Q³, Q⁴, Q⁵ and Q⁶ of the group of formulas (3); R¹ through R⁵ are independently selected from hydrogen, hydroxyl, cyano, nitro, halogen, phenyl, C₁₋₆ alkyl, C₁₋₆ haloalkyl, C₂₋₆ alkenyl, C₂₋₆ haloalkenyl, C₂₋₆ alkynyl, C₂₋₆ haloalkynyl , C₁₋₆ alkoxy, C₁₋₆ haloalkoxy, C₁₋₆ alkylthio, or benzyloxy, where R¹ and R² may form a benzene ring, a 5-7 membered aliphatic heterocycle containing 1-4 heteroatoms, or a 5-7 aromatic heterocycle members containing 1-4 heteroatoms together with the connected benzene ring carbon atoms; R² and R³ can form a benzene ring, a 5-7 membered aliphatic heterocycle containing 1-4 heteroatoms, or a 5-7 membered aromatic heterocycle containing 1-4 heteroatoms together with the connected benzene ring carbon atoms; R⁶, R⁷, and R⁸ are independently selected from hydrogen, C₁₋₆ alkyl, C₁₋₆ haloalkyl, C₃₋₆ cycloalkyl, C₃₋₆ cycloalkyl, C₁₋₆ alkyl, C₂₋₆ alkenyl, C₂₋₆ alkynyl, or phenyl; R⁹, R¹⁰, and R¹¹ are independently selected from hydrogen, halogen, cyano, nitro, C₁₋₆ alkylsulfonyl, C₁₋₆ haloalkylsulfonyl, C₁₋₆ alkylsulfinyl, C₁₋₆ haloalkylsulfinyl, C₁₋₆ alkylthio, C₁₋₆ C₁₋₆ alkyl, c₁₋₆ haloalkyl, c₁₋₆ alkoxy, c₁₋₆ haloalkoxy, c₁₋₃ alkoxy alkyl, c₁₋₆ alkoxy alkoxy, c₁₋₆ alcoxican alcoxican alkyl, c₃₋₆ cycloalkyl, C₃₋₆ cycloalkylC₁₋₃ alkyl, C₃₋₆ cycloalkylC₁₋₃ alkoxy or C₃₋₆ cycloalkyloxy; a stereoisomer of the compound of formula (1) above; or the compound of formula (1) and an agriculturally acceptable salt of the isomer.

ARP200102772A 2019-10-08 2020-10-07 ALKHENAMIDE COMPOUND AND APPLICATION THEREOF AR120168A1 (en)

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