AR094160A1 - FUNGICIDE COMPOUNDS OF IMIDAZOLILO AND TRIAZOLILO - Google Patents

FUNGICIDE COMPOUNDS OF IMIDAZOLILO AND TRIAZOLILO

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AR094160A1
AR094160A1 ARP130104886A ARP130104886A AR094160A1 AR 094160 A1 AR094160 A1 AR 094160A1 AR P130104886 A ARP130104886 A AR P130104886A AR P130104886 A ARP130104886 A AR P130104886A AR 094160 A1 AR094160 A1 AR 094160A1
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Argentina
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alkyl
cycloalkyl
alkoxy
halogen
haloalkyl
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ARP130104886A
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Spanish (es)
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Basf Se
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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D233/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings
    • C07D233/54—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members
    • C07D233/56—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members with only hydrogen atoms or radicals containing only hydrogen and carbon atoms, attached to ring carbon atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D233/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings
    • C07D233/54—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members
    • C07D233/66—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D233/68—Halogen atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D233/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings
    • C07D233/54—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members
    • C07D233/66—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D233/84—Sulfur atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D251/00—Heterocyclic compounds containing 1,3,5-triazine rings
    • C07D251/02—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings
    • C07D251/10—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings having two double bonds between ring members or between ring members and non-ring members

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Plural Heterocyclic Compounds (AREA)
  • Agricultural Chemicals And Associated Chemicals (AREA)
  • Pretreatment Of Seeds And Plants (AREA)

Abstract

Compuestos fungicidas I de imidazolilo y triazolilo, composiciones agroquímica que los comprenden, su uso y métodos para combatir hongos fitopatogénicos. También semillas tratadas con al menos uno de esos compuestos. Además, procesos para preparar compuestos de la fórmula (1) e intermediarios específicos que se obtienen durante la secuencia de reacción. Reivindicación 1: Compuestos caracterizados porque tienen la fórmula (1) en donde: A es N o CH; D es hidrógeno, halógeno o SRD; en donde RD es hidrógeno, CN, alquilo C₁₋₆, haloalquilo C₁₋₆, alquenilo C₂₋₆, haloalquenilo C₂₋₆, alquinilo C₂₋₆ o haloalquinilo C₂₋₆; R¹ es halógeno, CN, NO₂, OH, SH, alquilo C₁₋₆, alcoxi C₁₋₆, alquil C₁₋₆tio, alquil C₁₋₆sulfinilo, alquil C₁₋₆sulfonilo, alquenilo C₂₋₆, alquinilo C₂₋₆, cicloalquilo C₃₋₈, cicloalcoxi C₃₋₈, cicloalquil C₃₋₈-alquilo C₁₋₄, NH₂, NH(alquilo C₁₋₄), N(alquilo C₁₋₄)₂, NH(cicloalquilo C₃₋₆), N(cicloalquilo C₃₋₆)₂, C(=O)-alquilo C₁₋₄, C₍₌O₎OH, C₍₌O₎₋O₋ₐₗqᵘⁱₗₒ C₁₋₄, C₍₌O₎₋NH₍ₐₗqᵘⁱₗₒ C₁₋₄), C(=O)-N(alquilo C₁₋₄)₂, C(=O)-NH(cicloalquilo C₃₋₆), C(=O)-N(cicloalquilo C₃₋₆)₂, fenilo, heteroarilo, fenil-alquilo C₁₋₄ o heteroaril-alquilo C₁₋₄ en donde el radical heteroarilo en los últimos grupos mencionados tienen 5 ó 6 miembros; y en donde las porciones alifáticas, alicíclicas y aromáticas de R¹ son no sustituidas o sustituidas con 1, 2, 3 ó 4 o hasta la mayor cantidad posible de sustituyentes R¹ᵃ seleccionados independientemente; en donde R¹ᵃ es halógeno, CN, NO₂, OH, SH, NH₂, alquilo C₁₋₆, haloalquilo C₁₋₆, alcoxi C₁₋₆, haloalcoxi C₁₋₆, alquil C₁₋₆tio, haloalquil C₁₋₆tio, cicloalquilo C₃₋₈ o alcoxi C₁₋₄-alquilo C₁₋₄; R² es hidrógeno, halógeno, CN, NO₂, OH, SH, alquilo C₁₋₆, alcoxi C₁₋₆, alquil C₁₋₆tio, alquil C₁₋₆sulfinilo alquil C₂₋₆sulfonilo, alquenilo C₂₋₆, alquinilo C₂₋₆, cicloalquilo C₃₋₈, cicIoalquiloxicicloalcoxi C₃₋₈, NH₂, NH(alquilo C₁₋₄), N(alquilo C₁₋₄)₂, NH(cicloalquilo C₃₋₆), N(cicloalquilo C₃₋₆)₂, C(=O)-alquilo C₁₋₄, C₍₌O₎OH, C₍₌O₎₋O₋ₐₗqᵘⁱₗₒ C₁₋₄, C₍₌O₎₋NH₍ₐₗqᵘⁱₗₒ C₁₋₄), C(O)-N(alquilo C₁₋₄)₂, C(=O)-NH(cicloalquilo C₃₋₆), C(=O)-N(cicloalquilo C₃₋₆)₂, fenilo, heteroarilo, fenil-alquilo C₁₋₄ o heteroaril-alquilo C₁₋₄, en donde el grupo heteroarilo en los últimos grupos mencionados tiene 5 ó 6 miembros; y en donde las porciones alifáticas, alicíclicas y aromáticas de R² son no sustituidas o sustituidas con 1, 2, 3 ó 4 o hasta la mayor cantidad posible de sustituyentes R²ᵃ seleccionados independientemente: en donde R²ᵃ es halógeno, CN, NO₂, OH, SH, NH₂, alquilo C₁₋₆, haloalquilo C₁₋₆, alcoxi C₁₋₆, haloalcoxi C₁₋₆, alquil C₁₋₆tio, haloalquil C₁₋₆tio, cicloalquilo C₃₋₈ o alcoxi C₁₋₄-alquilo C₁₋₄; o R¹ y R², junto con el átomo de carbono al que están unidos (denominado C*), forman un grupo vinilo C*=CR¹¹R²², en donde R¹¹ y R²² se seleccionan independientemente del grupo que consiste en hidrógeno, halógeno, CN, NO₂, OH, SH, NH₂, alquilo C₁₋₆, haloalquilo C₁₋₆, alcoxi C₁₋₆, haloalcoxi C₁₋₆, alquil C₁₋₆tio, haloalquil C₁₋₆tio y alcoxi C₁₋₄-alquilo C₁₋₄; o R¹ y R² forman, junto con el átomo de carbono al que están unidos, un carbociclo saturado o parcialmente insaturado de 3, 4, 5, 6 ó 7 miembros o un heterociclo saturado o parcialmente insaturado de 3, 4, 5, 6 ó 7 miembros, en donde el heterociclo incluye, además de átomos de carbono, 1 2, 3 ó 4 heteroátomos seleccionados independientemente del grupo que consiste en N, O y S, y en donde el carbociclo y heterociclo son no sustituidos o tienen 1, 2, 3 ó 4 sustituyentes R¹² seleccionados independientemente en donde uno o dos grupos CH₂ del carbociclo o heterociclo se pueden reemplazar por uno o dos grupos seleccionados independientemente del grupo de C(=O) y C(=S); en donde R¹² es halógeno, CN, NO₂, OH, SH, NH₂, alquilo C₁₋₆, haloalquilo C₁₋₆, alcoxi C₁₋₆, haloalcoxi C₁₋₆, alquil C₁₋₆tio, haloalquil C₁₋₆tio, alcoxi C₁₋₄-alquilo C₁₋₄, fenilo o fenoxi; en donde las porciones fenilo de R¹² son no sustituidas o sustituidas con 1, 2, 3 ó 4 sustituyentes R¹²ᵃ seleccionados independientemente; en donde R¹²ᵃ es halógeno, CN, NO₂, OH, SH, NH₂, alquilo C₁₋₆, haloalquilo C₁₋₆, alcoxi C₁₋₆, haloalcoxi C₁₋₆, alquil C₁₋₆tio, haloalquil C₁₋₆tio, cicloalquilo C₃₋₈ o alcoxi C₁₋₄-alquilo C₁₋₄; X es OR³ o CN; en donde R³ es hidrógeno, alquilo C₁₋₆, alquenilo C₂₋₆, alquinilo C₂₋₆, alquinilo C₂₋₆, cicloalquilo C₃₋₈, alquil C₁₋₆sulfonilo, fenilsulfonilo, C(=O)-alquilo C₁₋₄, C₍₌O₎₋O₋ₐₗqᵘⁱₗₒ C₁₋₄, C₍₌O₎₋NH₍ₐₗqᵘⁱₗₒ C₁₋₄), C(=O)-N(alquilo C₁₋₄)₂, C(=O)-alquil C₁₋₄fenilo, fenilo, fenil-alquilo C₁₋₄, fenil-alquenilo C₂₋₄ o fenil-alquinilo C₂₋₄; en donde las porciones alifáticas, alicíclicas y aromáticas de R³ son no sustituidas o sustituidas con 1, 2, 3 ó 4 o hasta la mayor cantidad posible de sustituyentes R³ᵃ seleccionados independientemente; en donde R³ᵃ es halógeno, CN, NO₂, OH, alquilo C₁₋₄, halógeno-alquilo C₁₋₄, cicloalquilo C₃₋₈, alcoxi C₁₋₄ o halógeno-alcoxi C₁₋₄; R⁴ se selecciona independientemente del grupo que consiste en halógeno, CN, NO₂, OH, SH, alquilo C₁₋₆, alcoxi C₁₋₆, alquil C₁₋₆tio, alquil C₁₋₆sulfinilo, alquil C₁₋₆sulfonilo, alquenilo C₂₋₆, alquinilo C₂₋₆, cicloalquilo C₃₋₈, cicloalquiloxi C₃₋₈, NH₂, NH(alquilo C₁₋₄), N(alquilo C₁₋₄)₂, NH(cicloalquilo C₃₋₆), N(cicloalquilo C₃₋₆)₂, C(=O)-alquilo C₁₋₄, C₍₌O₎OH, C₍₌O₎₋O₋ₐₗqᵘⁱₗₒ C₁₋₄, C₍₌O₎₋NH₍ₐₗqᵘⁱₗₒ C₁₋₄), C(=O)N(alquilo C₁₋₄)₂, C(=O)-NH(cicloalquilo C₃₋₆) y C(=O)-N(cicloalquilo C₃₋₆)₂; en donde las porciones alifáticas y alicíclicas de R⁴ son no sustituidas o sustituidas con 1, 2, 3 ó 4 o hasta la mayor cantidad posible de sustituyentes R⁴ᵃ seleccionados independientemente; en donde R⁴ᵃ es halógeno, CN, NO₂, OH, alquilo C₁₋₄, haloalquilo C₁₋₄, cicloalquilo C₃₋₈, alcoxi C₁₋₄ o halógeno-alcoxi C₁₋₄; n es 0, 1, 2, 3 ó 4; Y es un enlace directo o un radical divalente seleccionado de -O-, -S(=O)ₚ-, -CRY¹RY²-, -N(RYN)-, CRY³RY⁴-CRY⁵RY⁶-, -CRY⁷=CY⁸- y -CºC-, en donde RYN, RY¹, RY², RY³, RY⁴, RY⁵, RY⁶, RY⁷ y RY⁸ se seleccionan independientemente del grupo que consiste en hidrógeno, halógeno, CN, nitro, OH, alquilo C₁₋₄, halógeno-alquiloFungicidal compounds I of imidazolyl and triazolyl, agrochemical compositions comprising them, their use and methods to combat phytopathogenic fungi. Also seeds treated with at least one of those compounds. In addition, processes for preparing compounds of the formula (1) and specific intermediates that are obtained during the reaction sequence. Claim 1: Compounds characterized in that they have the formula (1) wherein: A is N or CH; D is hydrogen, halogen or SRD; wherein RD is hydrogen, CN, C₁₋₆ alkyl, C₁₋₆ haloalkyl, C₂₋₆ alkenyl, C₂₋₆ haloalkenyl, C₂₋₆ alkynyl or C₂₋₆ haloalkynyl; R¹ is halogen, CN, NO₂, OH, SH, C₁₋₆ alkyl, C₁₋₆ alkoxy, C₁₋₆thio alkyl, C₁₋₆sulfinyl alkyl, C₁₋₆sulfonyl alkyl, C₂₋₆ alkenyl, C₂₋₆ alkynyl, C₃₋ cycloalkyl ₈, C₃₋₈ cycloalkoxy, C₃₋₈ cycloalkyl-C₁₋₄ alkyl, NH₂, NH (C₁₋₄ alkyl), N (C₁₋₄ alkyl) ₂, NH (C₃₋₆ cycloalkyl), N (C₃₋₆ cycloalkyl ) ₂, C (= O) -C₁₋₄ alkyl, C₍₌O₎OH, C₍₌O₎₋O₋ₐₗqᵘⁱₗₒ C₁₋₄, C₍₌O₎₋NH₍ₐₗqᵘⁱₗₒ C₁₋₄), C ( = O) -N (C₁₋₄ alkyl) ₂, C (= O) -NH (C₃₋₆ cycloalkyl), C (= O) -N (C₃₋₆ cycloalkyl) ₂, phenyl, heteroaryl, phenyl-C₁ alkyl ₋₄ or heteroaryl-C₁₋₄ alkyl wherein the heteroaryl radical in the last mentioned groups has 5 or 6 members; and wherein the aliphatic, alicyclic and aromatic portions of R¹ are unsubstituted or substituted with 1, 2, 3 or 4 or up to the largest possible number of independently selected R¹ᵃ substituents; wherein R¹ᵃ is halogen, CN, NO₂, OH, SH, NH₂, C₁₋₆ alkyl, C₁₋₆ haloalkyl, C₁₋₆ alkoxy, C₁₋₆thioalkoxy, C₁₋₆tio alkyl, C₁₋₆thio haloalkyl, C₃₋₈ cycloalkyl or C₁₋₄-C₁₋₄ alkyl alkoxy; R² is hydrogen, halogen, CN, NO₂, OH, SH, C₁₋₆ alkyl, C alco alkoxy, C₁₋₆thio alkyl, C₁₋₆sulfinyl alkyl C₂₋₆sulfonyl alkyl, C₂₋₆ alkenyl, C₂₋₆ alkynyl, C₃ cycloalkyl ₋₈, CI cycloalkyloxycycloalkoxy, NH₂, NH (C₁₋₄ alkyl), N (C₁₋₄ alkyl) ₂, NH (C₃₋₆ cycloalkyl), N (C₃₋₆ cycloalkyl) ₂, C (= O) - C₁₋₄ alkyl, C₍₌O₎OH, C₍₌O₎₋O₋ₐₗqᵘⁱₗₒ C₁₋₄, C₍₌O₎₋NH₍ₐₗqᵘⁱₗₒ C₁₋₄), C (O) -N (C₁₋₄ alkyl ) ₂, C (= O) -NH (C₃₋₆ cycloalkyl), C (= O) -N (C₃₋₆ cycloalkyl) ₂, phenyl, heteroaryl, phenyl-C₁₋₄ alkyl or heteroaryl-C₁₋₄ alkyl, wherein the heteroaryl group in the last mentioned groups has 5 or 6 members; and wherein the aliphatic, alicyclic and aromatic portions of R² are unsubstituted or substituted with 1, 2, 3 or 4 or up to the largest possible number of independently selected R²ᵃ substituents: where R²ᵃ is halogen, CN, NO₂, OH, SH , NH₂, C₁₋₆ alkyl, C₁₋₆ haloalkyl, C₁₋₆ alkoxy, C₁₋₆ haloalkoxy, C₁₋₆thio alkyl, C₁₋₆thio haloalkyl, C₃₋₈ cycloalkyl or C₁₋₄ alkoxy-C₁₋₄ alkyl; or R¹ and R², together with the carbon atom to which they are attached (called C *), form a vinyl group C * = CR¹¹R²², where R¹¹ and R²² are independently selected from the group consisting of hydrogen, halogen, CN, NO₂ , OH, SH, NH₂, C₁₋₆ alkyl, C₁₋₆ haloalkyl, C₁₋₆ alkoxy, C₁₋₆ haloalkoxy, C₁₋₆thio alkyl, C₁₋₆thio haloalkyl and C₁₋₄ alkoxy-C₁₋₄ alkyl; or R¹ and R² together with the carbon atom to which they are attached, a saturated or partially unsaturated carbocycle of 3, 4, 5, 6 or 7 members or a saturated or partially unsaturated heterocycle of 3, 4, 5, 6 or 7 members, wherein the heterocycle includes, in addition to carbon atoms, 1 2, 3 or 4 heteroatoms independently selected from the group consisting of N, O and S, and where the carbocycle and heterocycle are unsubstituted or have 1, 2 , 3 or 4 independently selected R¹² substituents wherein one or two CH₂ groups of the carbocycle or heterocycle can be replaced by one or two groups independently selected from the group of C (= O) and C (= S); wherein R¹² is halogen, CN, NO₂, OH, SH, NH₂, C₁₋₆ alkyl, C₁₋₆ haloalkyl, C₁₋₆ alkoxy, C₁₋₆ haloalkoxy, C₁₋₆tio alkyl, C₁₋₆tio haloalkyl, C₁₋₄ alkoxy -C₁₋₄ alkyl, phenyl or phenoxy; wherein the phenyl portions of R¹² are unsubstituted or substituted with 1, 2, 3 or 4 independently selected R¹²ᵃ substituents; wherein R¹²ᵃ is halogen, CN, NO₂, OH, SH, NH₂, C₁₋₆ alkyl, C₁₋₆ haloalkyl, C₁₋₆ alkoxy, C₁₋₆ haloalkoxy, C₁₋₆thio alkyl, C₁₋₆thio haloalkyl, C₃₋₈ cycloalkyl or C₁₋₄-C₁₋₄ alkyl alkoxy; X is OR³ or CN; wherein R³ is hydrogen, C₁₋₆ alkyl, C₂₋₆ alkenyl, C₂₋₆ alkynyl, C₂₋₆ alkynyl, C₃₋₈ cycloalkyl, Culfsulfonyl alkyl, phenylsulfonyl, C (= O) -C₁₋₄ alkyl, C ₍₌O₎₋O₋ₐₗqᵘⁱₗₒ C₁₋₄, C₍₌O₎₋NH₍ₐₗqᵘⁱₗₒ C₁₋₄), C (= O) -N (C₁₋₄ alkyl) ₂, C (= O) -C₁₋ alkyl ₄phenyl, phenyl, phenyl-C₁₋₄-alkyl, phenyl-Cque-alkenyl or phenyl-C alqu-alkynyl; wherein the aliphatic, alicyclic and aromatic portions of R³ are unsubstituted or substituted with 1, 2, 3 or 4 or even as many R³ de substituents independently selected; wherein R³ᵃ is halogen, CN, NO₂, OH, C₁₋₄ alkyl, halogen-C₁₋₄ alkyl, C₃₋₈ cycloalkyl, C₁₋₄ alkoxy or halogen-C₁₋₄ alkoxy; R⁴ is independently selected from the group consisting of halogen, CN, NO₂, OH, SH, C₁₋₆ alkyl, C₁₋₆ alkoxy, C₁₋₆thio alkyl, C₁₋₆sulfinyl alkyl, C₁₋₆sulfonyl alkyl, C₂₋₆ alkenyl, alkynyl C₂₋₆, C₃₋₈ cycloalkyl, C₃₋₈ cycloalkyloxy, NH₂, NH (C₁₋₄ alkyl), N (C₁₋₄ alkyl) NH, NH (C₃₋₆ cycloalkyl), N (C₃₋₆ cycloalkyl) ₂, C (= O) -alkyl C₁₋₄, C₍₌O₎OH, C₍₌O₎₋O₋ₐₗqᵘⁱₗₒ C₁₋₄, C₍₌O₎₋NH₍ₐₗqᵘⁱₗₒ C₁₋₄), C (= O) N (C₁₋₄ alkyl) ₂, C (= O) -NH (C₃₋₆ cycloalkyl) and C (= O) -N (C₃₋₆ cycloalkyl) ₂; wherein the aliphatic and alicyclic portions of R⁴ are unsubstituted or substituted with 1, 2, 3 or 4 or even as many R independientemente substituents independently selected; wherein R⁴ᵃ is halogen, CN, NO₂, OH, C₁₋₄ alkyl, C₁₋₄ haloalkyl, C₃₋₈ cycloalkyl, C₁₋₄ alkoxy or halogen-C₁₋₄ alkoxy; n is 0, 1, 2, 3 or 4; Y is a direct bond or a divalent radical selected from -O-, -S (= O) ₚ-, -CRY¹RY²-, -N (RYN) -, CRY³RY⁴-CRY⁵RY⁶-, -CRY⁷ = CY⁸- and -CºC-, wherein RYN, RY¹, RY², RY³, RY⁴, RY⁵, RY⁶, RY⁷ and RY⁸ are independently selected from the group consisting of hydrogen, halogen, CN, nitro, OH, C₁₋₄ alkyl, halogen-alkyl

ARP130104886A 2012-12-19 2013-12-19 FUNGICIDE COMPOUNDS OF IMIDAZOLILO AND TRIAZOLILO AR094160A1 (en)

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EP2924027A1 (en) * 2014-03-28 2015-09-30 Basf Se Substituted [1,2,4]triazole and imidazole fungicidal compounds
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AR100743A1 (en) 2014-06-06 2016-10-26 Basf Se COMPOUNDS OF [1,2,4] SUBSTITUTED TRIAZOL
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