WO2015004091A1 - Dérivés de nicotinamide et utilisation de ces derniers contre les nématodes - Google Patents

Dérivés de nicotinamide et utilisation de ces derniers contre les nématodes Download PDF

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WO2015004091A1
WO2015004091A1 PCT/EP2014/064511 EP2014064511W WO2015004091A1 WO 2015004091 A1 WO2015004091 A1 WO 2015004091A1 EP 2014064511 W EP2014064511 W EP 2014064511W WO 2015004091 A1 WO2015004091 A1 WO 2015004091A1
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alkyl
hydrogen
formula
independently
compound
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PCT/EP2014/064511
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Olivier Loiseleur
André Jeanguenat
Régis Jean Georges MONDIERE
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Syngenta Participations Ag
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    • 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
    • A01N43/34—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom
    • A01N43/40—Biocides, 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
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C211/00—Compounds containing amino groups bound to a carbon skeleton
    • C07C211/01—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to acyclic carbon atoms
    • C07C211/26—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to acyclic carbon atoms of an unsaturated carbon skeleton containing at least one six-membered aromatic ring
    • C07C211/29—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to acyclic carbon atoms of an unsaturated carbon skeleton containing at least one six-membered aromatic ring the carbon skeleton being further substituted by halogen atoms or by nitro or nitroso groups
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
    • C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
    • C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom 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
    • C07D213/78—Carbon atoms having three bonds to hetero atoms, with at the most one bond to halogen, e.g. ester or nitrile radicals
    • C07D213/81—Amides; Imides
    • C07D213/82—Amides; Imides in position 3

Definitions

  • the present invention relates to novel carboxamide compounds, a process for the preparation of these compounds and their use as pesticides, in particular nematicides.
  • Carboxamides are described, for example, in WO2005/058828, WO2007/108483,
  • Novel phenethyl nicotinamides containing a 2-fluorinated phenyl moiety have now been found, which show good pesticidal, in particular nematicidal, activity.
  • the present invention thus relates to a method of protecting crops or useful plants against damage caused by nematode pests, which comprises treating the plants or the locus thereof with a compound of the formula (I)
  • R1 represents C1 -C2-alkyl or C1 -C2-haloalkyl
  • R2 represents hydrogen, C1 -C4-alkyl, C1 -C4 alkyl substituted by CN, C1 -C4-alkoxy, C1 -C4- alkoxycarbonyl, C2-C4-alkenyl, C2-C4-alkynyl, C3-C6-cycloalkylcarbonyl, C3-C6-cycloalkoxycarbonyl or benzyl;
  • R3 and R4 independently of each other represent hydrogen or fluorine
  • R5a, R5b, R5c and R5d each independently of each other represents hydrogen, halogen, cyano, C1 -C4-alkyl, C1 -C4-haloalkyl, C1 -C4-alkoxy, C1 -C4-haloalkoxy, C1 -C4-alkylsulfanyl, C1 -C4- haloalkylsulfanyl, C1 -C4-alkylsulfinyl, C1 -C4-haloalkylsulfinyl, C1 -C4-alkylsulfonyl, C1 -C4- haloalkylsulfonyl C3-C6-cycloalkyl, C2-C6-alkenyl or C2-C6 haloalkynyl, wherein the cycloalkyl is optionally substituted by one or more R6 and the alkenyl is substituted by one or more
  • each R6 independently of each other represents halogen, C1 -C4-alkyl or C1 -C4-haloalkyl;
  • R7 represents hydrogen or methyl
  • each alkyl moiety either alone or as part of a larger group is a straight or branched chain and is, for example, methyl, ethyl, n-propyl, n-butyl, isopropyl, sec-butyl, isobutyl or terf-butyl.
  • Alkenyl and alkynyl moieties can be in the form of straight or branched chains, and the alkenyl moieties, where appropriate, can be of either the (E)- or (Z)-configuration. Examples are vinyl, allyl and propargyl. Alkenyl and alkynyl moieties can contain one or more double and/or triple bonds in any combination. Preferably, the alkenyl and alkynyl moieties contain 2 to 4 carbon atoms.
  • Halogen is fluorine, chlorine, bromine or iodine, preferably fluorine, chlorine or bromine.
  • Haloalkyl groups are alkyl groups which are substituted with one or more of the same or different halogen atoms and are, for example, CF 3 , CF 2 CI, CF 2 H, CCI 2 H, CFH 2 , CH 2 CI, CH 2 Br, CH 3 CHF, (CH 3 ) 2 CF, CF 3 CH 2 or CHF 2 CH 2 .
  • R1 represents C1 -C2-alkyl or C1 -C2-haloalkyl.
  • R1 represents methyl or trifluoromethyl.
  • R1 represents trifluoromethyl.
  • R2 represents hydrogen, C1 -C4-alkyl, C1 -C4 alkyl substituted by CN, C1 -C4-alkoxy, C1 -C4- alkoxycarbonyl, C2-C4-alkenyl, C2-C4-alkynyl, C3-C6-cycloalkylcarbonyl, C3-C6-cycloalkoxycarbonyl or benzyl.
  • R2 represents hydrogen, C1 -C2-alkyl, C1 -C2 alkyl substituted by CN, C1 -C2-alkoxy, C1 -C2-alkoxycarbonyl, ethenyl, ethynyl, C3-C6-cycloalkylcarbonyl, C3-C6-cycloalkoxycarbonyl or benzyl.
  • R2 represents hydrogen
  • R3 and R4 independently of each other represent hydrogen or fluorine.
  • R5a, R5b, R5c and R5d each independently of each other represent hydrogen, halogen, cyano, C1 -C4-alkyl, C1 -C4-haloalkyl, C1 -C4-alkoxy, C1 -C4-haloalkoxy, C1 -C4-alkylsulfanyl, C1 -C4- haloalkylsulfanyl, C1 -C4-alkylsulfinyl, C1 -C4-haloalkylsulfinyl, C1 -C4-alkylsulfonyl, C1 -C4- haloalkylsulfonyl, C3-C6-cycloalkyl, C2-C6-alkenyl or C2-C6 haloalkynyl, wherein the cycloalkyl is optionally substituted by one or more R6 and the alkenyl is substituted by one or
  • R5a, R5b, R5c and R5d independently of each other represent hydrogen, halogen, cyano, C1 -C2-alkyl, C1 -C2-haloalkyl, C1 -C2-alkoxy, C1 -C2-haloalkoxy, C1 -C2-alkylsulfanyl, C1 -C2- haloalkylsulfanyl, C1 -C2-alkylsulfinyl, C1 -C2-haloalkylsulfinyl, C1 -C2-alkylsulfonyl, C1 -C2- haloalkylsulfonyl, C3-C6-cycloalkyl, C2-C6-alkenyl or C2-C6 haloalkynyl, wherein the cycloalkyl is optionally substituted by one or more R6 and the alkenyl is substituted by one or more R6.
  • R5a, R5b, R5c and R5d independently of each other represent hydrogen, halogen, cyano, C1 -C2-alkyl, C1 -C2-haloalkyl, C1 -C2-alkoxy, C1 -C2-haloalkoxy, C3-C6-cycloalkyl, C2-C6-alkenyl or C2-C6 haloalkynyl, wherein the cycloalkyl is optionally substituted by one or more R6 and the alkenyl is substituted by one or more R6.
  • R5a, R5b, R5c and R5d independently of each other represent hydrogen, halogen, cyano, C1 -C4-haloalkyl or C1 -C4-haloalkoxy.
  • R5a, R5b, R5c and R5d independently of each other represent hydrogen, halogen, cyano, C1 -C2-haloalkyl or C1 -C2-haloalkoxy. Even more preferably, R5a, R5b, R5c and R5d independently of each other represent hydrogen, halogen, cyano or halomethyl.
  • R5a, R5b, R5c and R5d independently of each other represent hydrogen, fluoro, chloro, bromo, cyano, difluoromethyl, trifluoromethyl, difluoromethoxy or trifluoromethoxy.
  • R5a, R5b, R5c and R5d independently of each other represent hydrogen, fluoro, chloro, bromo, difluoromethyl, trifluoromethyl, difluoromethoxy or trifluoromethoxy.
  • R5a, R5b, R5c and R5d independently of each other represent hydrogen, fluoro, chloro, bromo, or trifluoromethyl.
  • At least two of R5a, R5b, R5c and R5d represent hydrogen.
  • R5a, R5b, R5c and R5d represent hydrogen.
  • R5a, R5c and R5d represent hydrogen.
  • Each R6 independently of each other represents halogen, C1 -C4-alkyl or C1 -C4-haloalkyl.
  • each R6 independently of each other represents halogen, C 1 -C2-alkyl or C1 -C2- haloalkyl.
  • R7 represents hydrogen or methyl.
  • R7 is hydrogen
  • R7 is preferably methyl.
  • R1 represents C1 -C2-alkyl or C1 -C2-haloalkyl
  • R2 represents hydrogen, C1 -C4-alkyl, C1 -C4 alkyl substituted by CN, C1 -C4-alkoxy, C1 -C4- alkoxycarbonyl, C2-C4-alkenyl, C2-C4-alkynyl, C3-C6-cycloalkylcarbonyl, C3-C6-cycloalkoxycarbonyl or benzyl;
  • R3 and R4 independently of each other represent hydrogen or fluorine
  • R5a, R5b, R5c and R5d independently of each other represent hydrogen, halogen, cyano, C1 - C4-alkyl, C1 -C4-haloalkyl, C1 -C4-alkoxy, C1 -C4-haloalkoxy, C1 -C4-alkylsulfanyl, C1 -C4- haloalkylsulfanyl, C1 -C4-alkylsulfinyl, C1 -C4-haloalkylsulfinyl, C1 -C4-alkylsulfonyl, C1 -C4- haloalkylsulfonyl, C3-C6-cycloalkyl, C2-C6-alkenyl or C2-C6 haloalkynyl, wherein the cycloalkyi is optionally substituted by one or more R6 and the alkenyl is substituted by one or more
  • each R6 independently of each other represents halogen, C1 -C4-alkyl or C1 -C4-haloalkyl; R7 is hydrogen.
  • R1 represents C1 -C2-alkyl or C1 -C2-haloalkyl
  • R2 represents hydrogen, C1 -C2-alkyl, C1 -C2 alkyl substituted by CN, C1 -C2-alkoxy, C1 -C2- alkoxycarbonyl, ethenyl, ethynyl, C3-C6-cycloalkylcarbonyl, C3-C6-cycloalkoxycarbonyl or benzyl;
  • R3 and R4 independently of each other represent hydrogen and fluorine
  • R5a, R5b, R5c and R5d independently of each other represent hydrogen, halogen, cyano, C1 - C2-alkyl, C1 -C2-haloalkyl, C1 -C2-alkoxy, C1 -C2-haloalkoxy, C3-C6-cycloalkyl, C2-C6-alkenyl or C2- C6 haloalkynyl, wherein the cycloalkyi is optionally substituted by one or more R6 and the alkenyl is substituted by one or more R6; each R6 independently of each other represents halogen, C1 -C2-alkyl or C1 -C2-haloalkyl; R7 is hydrogen.
  • R1 represents C1 -C2-alkyl or C1 -C2-haloalkyl
  • R2 represents hydrogen, C1 -C2-alkyl, C1 -C2 alkyl substituted by CN, C1 -C2-alkoxy, C1 -C2- alkoxycarbonyl, ethenyl, ethynyl, C3-C6-cycloalkylcarbonyl, C3-C6-cycloalkoxycarbonyl or benzyl;
  • R3 and R4 independently of each other represent hydrogen and fluorine
  • R5a, R5b, R5c and R5d independently of each other represent hydrogen, halogen, cyano, C1 - C2-alkyl, C1 -C2-haloalkyl, C1 -C2-alkoxy, C1 -C2-haloalkoxy, C3-C6-cycloalkyl, C2-C6-alkenyl or C2- C6 haloalkynyl, wherein the cycloalkyi is optionally substituted by one or more R6 and the alkenyl is substituted by one or more R6;
  • R5a, R5b, R5c and R5d represent hydrogen
  • each R6 independently of each other represents halogen, C1 -C2-alkyl or C1 -C2-haloalkyl
  • R7 is hydrogen
  • R3 and R4 each represent fluorine.
  • R3 is hydrogen and R4 is fluorine.
  • R3 and R4 each represent hydrogen.
  • R1 represents methyl or trifluoromethyl
  • R2 represents hydrogen
  • R3 and R4 each independently represent hydrogen or fluorine
  • R5a, R5b, R5c and R5d independently of each other represent hydrogen, halogen, cyano, C1 -C2-haloalkyl or C1 -C2-haloalkoxy;
  • R7 is hydrogen
  • R1 represents trifluoromethyl
  • R2 represents hydrogen
  • R3 and R4 each independently of each other represent hydrogen or fluorine
  • R5a, R5b, R5c and R5d independently of each other represent hydrogen, fluoro, chloro, bromo, cyano, difluoromethyl, trifluoromethyl, difluoromethoxy or trifluoromethoxy;
  • R7 represents hydrogen
  • R5a, R5b, R5c and R5d represent hydrogen
  • R1 represents trifluoromethyl
  • R2 represents hydrogen
  • R3 and R4 each independently represent hydrogen or fluorine
  • R5a, R5c and R5d each represent hydrogen
  • R5b represents fluoro, chloro, bromo, cyano, difluoromethyl, trifluoromethyl, difluoromethoxy or trifluoromethoxy; R7 represents hydrogen.
  • R5b represents halogen, cyano, C1 -C4-alkyl, C1 -C4-haloalkyl, C1 -C4-alkoxy, C1 -C4-haloalkoxy, C1 -C4-alkylsulfanyl, C1-C4-haloalkylsulfanyl, C1 -C4-alkylsulfinyl, C1 -C4-haloalkylsulfinyl, C1 -C4-alkylsulfonyl, C1 -C4-haloalkylsulfonyl C3-C6-cycloalkyl, C2-C6-alkenyl or C2-C6 haloalkynyl, wherein the cycloalkyi is optionally substituted by one or more R6 and the alkenyl is substituted by one or more R6.
  • R5b represents halogen, cyano, C1 -C2-alkyl, C1 -C2- haloalkyl, C1 -C2-alkoxy, C1 -C2-haloalkoxy, C1 -C2-alkylsulfanyl, C1 -C2-haloalkylsulfanyl, C1 -C2- alkylsulfinyl, C1 -C2-haloalkylsulfinyl, C1 -C2-alkylsulfonyl, C1-C2-haloalkylsulfonyl C3-C6-cycloalkyl, C2-C6-alkenyl or C2-C6 haloalkynyl, wherein the cycloalkyi is optionally substituted by one or more R6 and the alkenyl is substituted by one or more R6.
  • R5b represents halogen, cyano, C1 -C2-alkyl, C1 - C2-haloalkyl, C1 -C2-alkoxy, C1 -C2-haloalkoxy, C3-C6-cycloalkyl, C2-C6-alkenyl or C2-C6 haloalkynyl, wherein the cycloalkyi is optionally substituted by one or more R6 and the alkenyl is substituted by one or more R6.
  • R5a, R5b, R5c and R5d independently of each other represent hydrogen, halogen, cyano, C1 -C4-haloalkyl or C1 -C4-haloalkoxy.
  • R5b represents halogen, cyano, C1 -C2- haloalkyl or C1 -C2-haloalkoxy.
  • R5b represents halogen, cyano or halomethyl.
  • R5b represents fluoro, chloro, bromo, cyano, difluoromethyl, trifluoromethyl, difluoromethoxy or trifluoromethoxy
  • R5b represents fluoro, chloro, bromo, difluoromethyl, trifluoromethyl, difluoromethoxy or trifluoromethoxy
  • R5b represents fluoro, chloro, bromo, or trifluoromethyl.
  • R1 , R2, R3, R4, R5a, R5c, R5d, R6 and R7 likewise apply to this group of compounds of formula (I).
  • R1 represents C1 -C2-alkyl or C1 -C2-haloalkyl
  • R2 represents hydrogen, C1 -C4-alkyl, C1 -C4 alkyl substituted by CN, C1 -C4-alkoxy, C1 -C4- alkoxycarbonyl, C2-C4-alkenyl, C2-C4-alkynyl, C3-C6-cycloalkylcarbonyl, C3-C6-cycloalkoxycarbonyl or benzyl;
  • R3 and R4 independently of each other represent hydrogen or fluorine
  • R5a, R5b, R5c each independently of each other represent hydrogen, halogen, cyano, C1 -C4- alkyl, C1 -C4-haloalkyl, C1 -C4-alkoxy, C1 -C4-haloalkoxy, C1 -C4-alkylsulfanyl, C1 -C4-haloalkylsulfanyl, C1 -C4-alkylsulfinyl, C1 -C4-haloalkylsulfinyl, C1 -C4-alkylsulfonyl, C1 -C4-haloalkylsulfonyl, C3-C6- cycloalkyl, C2-C6-alkenyl or C2-C6 haloalkynyl, wherein the cycloalkyi is optionally substituted by one or more R6 and the alkenyl is substituted by one or more R6;
  • R5d represents hydrogen, chloro, bromo, cyano, C1 -C4-alkyl, C1 -C4-haloalkyl, C1 -C4-alkoxy, C1 -C4-haloalkoxy, C1 -C4-alkylsulfanyl, C1 -C4-haloalkylsulfanyl, C1 -C4-alkylsulfinyl, C1 -C4- haloalkylsulfinyl, C1 -C4-alkylsulfonyl, C1 -C4-haloalkylsulfonyl, C3-C6-cycloalkyl, C2-C6-alkenyl or C2-C6 haloalkynyl, wherein the cycloalkyi is optionally substituted by one or more R6 and the alkenyl is substituted by one or more R6;
  • each R6 independently of each other represents halogen, C1 -C4-alkyl or C1 -C4-haloalkyl;
  • R7 represents hydrogen or methyl.
  • R5d represents hydrogen
  • R1 , R2, R3, R4, R5a, R5b, R5c, R6 and R7 likewise apply to this group of compounds of formula (I).
  • R5b represents halogen, cyano, C1 -C4-alkyl, C1 -C4- haloalkyl, C1 -C4-alkoxy, C1 -C4-haloalkoxy, C1 -C4-alkylsulfanyl, C1 -C4-haloalkylsulfanyl, C1 -C4- alkylsulfinyl, C1 -C4-haloalkylsulfinyl, C1 -C4-alkylsulfonyl, C1-C4-haloalkylsulfonyl C3-C6-cycloalkyl, C2-C6-alkenyl or C2-C6 haloalkynyl, wherein the cyclo
  • R5b represents halogen, cyano, C1 -C2-alkyl, C1 -C2- haloalkyl, C1 -C2-alkoxy, C1 -C2-haloalkoxy, C1 -C2-alkylsulfanyl, C1 -C2-haloalkylsulfanyl, C1 -C2- alkylsulfinyl, C1 -C2-haloalkylsulfinyl, C1 -C2-alkylsulfonyl, C1-C2-haloalkylsulfonyl C3-C6-cycloalkyl, C2-C6-alkenyl or C2-C6 haloalkynyl, wherein the cycloalkyi is optionally substituted by one or more R6 and the alkenyl is substituted by one or more R6.
  • R5b represents halogen, cyano, C1 -C2-alkyl, C1 -
  • R5a, R5b, R5c and R5d independently of each other represent hydrogen, halogen, cyano, C1 -C4-haloalkyl or C1 -C4-haloalkoxy.
  • R5b represents halogen, cyano, C1 -C2- haloalkyl or C1 -C2-haloalkoxy.
  • R5b represents halogen, cyano or halomethyl.
  • R5b represents fluoro, chloro, bromo, cyano, difluoromethyl, trifluoromethyl, difluoromethoxy or trifluoromethoxy
  • R5b represents fluoro, chloro, bromo, difluoromethyl, trifluoromethyl, difluoromethoxy or trifluoromethoxy
  • R5b represents fluoro, chloro, bromo, or trifluoromethyl.
  • the invention provides the compounds of formula (II )
  • R3, R4, R5a, R5b, R5c, R5d and R7 are as defined herein for compounds of formula (I).
  • the preferred definitions of R3, R4, R5a, R5b, R5c, R5d and R7 defined in respect of compounds of formula (I) also apply to compounds of formula (II).
  • phosphoniumhexafluorophosphate bis-(2-oxo-3-oxazolidinyl)-phosphinic acid chloride (BOP-CI), ⁇ , ⁇ '-dicyclohexylcarbodiimide (DCC) or 1 ,1 '-carbonyl-diimidazole (CDI), may be used, as described in L. A. Paquette, Encyclopaedia of Reagents for Organic Synthesis, Vol 3. Wiley, England, 1995 pp 1751 -1754. Acylating agents of the formula (III) are known or are easily prepared by those skilled in the art.
  • Amines of the formula (Ma), that is a compound of formula (II) wherein R7 is hydrogen, can be prepared by treating nitriles of the formula (IV), wherein R3, R4, R5a, R5b, R5c and R5d are as defined herein for a compound of formula (I), with a reducing agent.
  • a typical reducing agent is hydrogen.
  • Typical catalysts are metals, metal salts, or metal complexes. Examples of such type of catalytic hydrogenations are listed in in R.C. Larock, Comprehensive Organic Transformations, Wiley -VCH, 1999, pp875-876.
  • Other typical reducing agents are hydrides.
  • Typical hydrides are borohydrides, or aluminium hydrides, examples of which are sodium borohydride or lithium aluminium hydride. Such hydride reductions can be facilitated by the use of other components such as metal salts.
  • Other typical reducing agents are boranes. Typical boranes are borane-tetrahydrofurane or -dimethylsulfide complexes. Examples of such type of reductions are listed in in R.C. Larock Comprehensive Organic Transformations, Wiley - VCH, 1999, pp875-876.
  • Nitriles of formula (IV) in which R3 and R4 are hydrogen are known or can be prepared according to various methods reported in the literature. An example is given in F. Stazi et al, Synthesis 2010, 19, 3332.
  • the reactants can be reacted in the presence of a base.
  • suitable bases are alkali metal or alkaline earth metal hydroxides, alkali metal or alkaline earth metal hydrides, alkali metal or alkaline earth metal amides, alkali metal or alkaline earth metal alkoxides, alkali metal or alkaline earth metal acetates, alkali metal or alkaline earth metal carbonates, alkali metal or alkaline earth metal dialkylamides or alkali metal or alkaline earth metal alkylsilylamides, alkylamines, alkylenediamines, free or N-alkylated saturated or unsaturated cycloalkylamines, basic heterocycles, ammonium hydroxides and carbocyclic amines.
  • sodium hydroxide sodium hydride, sodium amide, sodium methoxide, sodium acetate, sodium carbonate, potassium tert- butoxide, potassium hydroxide, potassium carbonate, potassium hydride, lithium diisopropylamide, potassium bis(trimethylsilyl)amide, calcium hydride, triethylamine, diisopropylethylamine,
  • the reactants can be reacted with each other as such, i.e. without adding a solvent or dilu ent. In most cases, however, it is advantageous to add an inert solvent or diluent or a mixture of these. If the reaction is carried out in the presence of a base, bases which are employed in excess, such as triethylamine, pyridine, N-methylmorpholine or ⁇ , ⁇ -diethylaniline, may also act as solvents or diluents.
  • the reaction is advantageously carried out in a temperature range from approximately -80°C to approximately +140°C, preferably from approximately -30°C to approximately +100°C, in many cases in the range between ambient temperature and approximately +80°C.
  • a compound of formula (I) can be converted in a manner known per se into another compound of formula (I) by replacing one or more substituents of the starting compound of formula (I) in the customary manner by (an)other substituent(s) according to the invention.
  • Salts of compounds of formula (I) can be prepared in a manner known per se.
  • acid addition salts of compounds of formula (I) are obtained by treatment with a suitable acid or a suitable ion exchanger reagent and salts with bases are obtained by treatment with a suitable base or with a suitable ion exchanger reagent.
  • a salt is chosen depending on its tolerances for compound's use, such as agricultural or physiological tolerance.
  • Salts of compounds of formula (I) can be converted in the customary manner into the free compounds I, acid addition salts, for example, by treatment with a suitable basic compound or with a suitable ion exchanger reagent and salts with bases, for example, by treatment with a suitable acid or with a suitable ion exchanger reagent.
  • Salts of compounds of formula (I) can be converted in a manner known per se into other salts of compounds of formula (I), acid addition salts, for example, into other acid addition salts, for example by treatment of a salt of inorganic acid such as hydrochloride with a suitable metal salt such as a sodium, barium or silver salt, of an acid, for example with silver acetate, in a suitable solvent in which an inorganic salt which forms, for example silver chloride, is insoluble and thus precipitates from the reaction mixture.
  • a salt of inorganic acid such as hydrochloride
  • a suitable metal salt such as a sodium, barium or silver salt
  • the compounds of formula (I), which have salt-forming properties can be obtained in free form or in the form of salts.
  • Diastereomer mixtures or racemate mixtures of compounds of formula (I), in free form or in salt form, which can be obtained depending on which starting materials and procedures have been chosen can be separated in a known manner into the pure diasteromers or racemates on the basis of the physicochemical differences of the components, for example by fractional crystallization, distillation and/or chromatography.
  • Enantiomer mixtures such as racemates, which can be obtained in a similar manner can be resolved into the optical antipodes by known methods, for example by recrystallization from an optically active solvent, by chromatography on chiral adsorbents, for example high-performance liquid chromatography (HPLC) on acetyl celulose, with the aid of suitable microorganisms, by cleavage with specific, enzymes, via the formation of inclusion compounds, for example using chiral crown ethers, where only one enantiomer is complexed, or by conversion into diastereomeric salts, for example by reacting a basic end-product racemate with an optically active acid, such as a carboxylic acid, for example camphoric, tartaric or malic acid, or sulfonic acid, for example camphorsulfonic acid, and separating the diastereomer mixture which can be obtained in this manner, for example by fractional crystallization based on their differing solubilities, to give the diaste
  • Pure diastereomers or enantiomers can be obtained according to the invention not only by separating suitable isomer mixtures, but also by generally known methods of diastereoselective or enantioselective synthesis, for example by carrying out the process according to the invention with starting materials of a suitable stereochemistry.
  • N-oxides can be prepared by reacting a compound of the formula (I) with a suitable oxidizing agent, for example the H 2 0 2 /urea adduct in the presence of an acid anhydride, e.g. trifluoroacetic anhydride.
  • a suitable oxidizing agent for example the H 2 0 2 /urea adduct
  • an acid anhydride e.g. trifluoroacetic anhydride.
  • the compounds of formula (I) and, where appropriate, the tautomers thereof, in each case in free form or in salt form, can, if appropriate, also be obtained in the form of hydrates and/or include other solvents, for example those which may have been used for the crystallization of compounds which are present in solid form.
  • the invention is further illustrated by making available the following individual compounds of formula (IA) listed below in Tables 1 to 1 1 .
  • Tables 1 to 1 1 which follow the Table Y below, make available 21 compounds of the formula (IA) in which R1 , R2, R3 and R4 are the substituents defined in Table Y and B is the substituent defined in the relevant Table 1 to 1 1 .
  • Table 1 individualises 21 compounds of formula (IA) wherein for each row of Table Y, the B substituent is as defined in Table 1 ; similarly, Table 2 individualises 21 compounds of formula (IA) wherein for each row of Table Y, the B substituent is as defined in Table 2; and so on for Tables 3 to 1 1 .
  • Table 1 provides 21 compounds of formula (IA), wherein B is
  • compound Y.001 has the following structure:
  • Table 2 provides 21 compounds of formula (IA) wherein B is 4-chloro-2-fluorophenyl (B2) and R1 , R2, R3 and R4 are as defined in each row of Table Y.
  • Table 3 provides 21 compounds of formula (IA) wherein B is 4-bromo-2-fluorophenyl (B3) and R1 , R2, R3 and R4 are as defined in each row of Table Y.
  • Table 4 provides 21 compounds of formula (IA) wherein B is 4-cyano-2-fluorophenyl (B4) and R1 , R2, R3 and R4 are as defined in each row of Table Y.
  • Table 5 provides 21 compounds of formula (IA) wherein B is 4-trifluoromethyl-2-fluorophi (B5) and R1 , R2, R3 and R4 are as defined in each row of Table Y.
  • Table 6 provides 21 compounds of formula (IA) wherein B is 4-trifluoromethoxy -2-fluorophi (B6) and R1 , R2, R3 and R4 are as defined in each row of Table Y.
  • Table 7 provides 21 compounds of formula (IA) wherein B is 4-difluoromethoxy -2-fluorophi (B7) and R1 , R2, R3 and R4 are as defined in each row of Table Y.
  • Table 8 provides 21 compounds of formula (IA) wherein B is 4-cyclopropyl -2-fluorophenyl (B8) and R1 , R2, R3 and R4 are as defined in each row of Table Y.
  • Table 9 provides 21 compounds of formula (IA) wherein B is 4-(2-trifluoromethyl-cycloprop-1 -yl) -2-fluorophenyl (B9) and R1 , R2, R3 and R4 are as defined in each row of Table Y.
  • Table 10 provides 21 compounds of formula (IA) wherein B is 4-methoxy -2-fluorophenyl (B10) and R1 , R2, R3 and R4 are as defined in each row of Table Y.
  • Table 1 1 provides 21 compounds of formula (IA) wherein B is 2,4,6-trifluorophenyl (B1 1 ) and R1 , R2, R3 and R4 are as defined in each row of Table Y.
  • the compounds according to the invention can be used for controlling or destroying pests such as insects and/or fungi which occur in particular on plants, especially on useful plants and ornamentals in agriculture, in horticulture and in forests, or on organs, such as fruits, flowers, foliage, stalks, tubers, seeds or roots, of such plants, and in some cases even plant organs which are formed at a later point in time remain protected against these pests.
  • pests such as insects and/or fungi which occur in particular on plants, especially on useful plants and ornamentals in agriculture, in horticulture and in forests, or on organs, such as fruits, flowers, foliage, stalks, tubers, seeds or roots, of such plants, and in some cases even plant organs which are formed at a later point in time remain protected against these pests.
  • the compounds of formula (I) according to the invention are preventively and/or curatively valuable active ingredients in the field of pest control, even at low rates of application, which can be used against pesticide resistant pests such as insects and fungi, which compounds of formula
  • the compounds of formula (I) according to the invention have, for practical purposes, a very advantageous spectrum of activities for protecting animals and useful plants against attack and damage by nematodes. Accordingly, the present invention also makes available a nematicidal composition comprising compounds of the invention, such as formula (I).
  • the invention also relates to a method of controlling damage to plant and parts thereof by plant parasitic nematodes (Endoparasitic-, Semiendoparasitic- and Ectoparasitic nematodes), especially plant parasitic nematodes such as root knot nematodes, Meloidogyne hapla, Meloidogyne incognita, Meloidogyne javanica, Meloidogyne arenaria and other Meloidogyne species; cyst-forming nematodes, Globodera rostochiensis and other Globodera species; Heterodera avenae, Heterodera glycines, Heterodera schachtii, Heterodera trifolii, and other Heterodera species; Seed gall nematodes, Anguina species; Stem and foliar nematodes
  • Needle nematodes Longidorus elongatus and other Longidorus species; Pin nematodes,
  • Pratylenchus species Lesion nematodes, Pratylenchus neglectus, Pratylenchus penetrans,
  • the nematode species Meloidogyne spp., Heterodera spp., Rotylenchus spp. and Pratylenchus spp. can be controlled by compounds of the invention.
  • a compound of the present invention is used in the form of a composition (e.g.
  • a compound of the invention and compositions thereof can be used in various forms such as aerosol dispenser, capsule suspension, cold fogging concentrate, dustable powder, emulsifiable concentrate, emulsion oil in water, emulsion water in oil, encapsulated granule, fine granule, flowable concentrate for seed treatment, gas (under pressure), gas generating product, granule, hot fogging concentrate, macrogranule, microgranule, oil dispersible powder, oil miscible flowable concentrate, oil miscible liquid, paste, plant rodlet, powder for dry seed treatment, seed coated with a pesticide, soluble concentrate, soluble powder, solution for seed treatment, suspension concentrate (flowable concentrate), ultra low volume (ulv) liquid, ultra low volume (ulv) suspension, water dispersible granules or tablets, water dispersible powder for slurry treatment, water soluble granules or tablets, water soluble powder for seed treatment and wettable powder.
  • a formulation typically comprises a liquid or solid carrier and optionally one or more customary formulaton auxiliaries, which may be solid or liquid auxiliaries, for example unepoxidized or epoxidized vegetable oils (for example epoxidized coconut oil, rapeseed oil or soya oil), antifoams, for example silicone oil, preservatives, clays, inorganic compounds, viscosity regulators, surfactant, binders and/or tackifiers.
  • customary formulaton auxiliaries for example unepoxidized or epoxidized vegetable oils (for example epoxidized coconut oil, rapeseed oil or soya oil), antifoams, for example silicone oil, preservatives, clays, inorganic compounds, viscosity regulators, surfactant, binders and/or tackifiers.
  • composition may also further comprise a fertilizer, a micronutrient donor or other preparations which influence the growth of plants as well as comprising a combination containing the compound of the invention with one or more other biologically active agents, such as bactericides, fungicides, nematocides, plant activators, acaricides, and insecticides.
  • a fertilizer such as bactericides, fungicides, nematocides, plant activators, acaricides, and insecticides.
  • the present invention also makes available a composition
  • a composition comprising a compound of the invention and an agronomicaly carrier and optionally one or more customary formulation auxiliaries.
  • compositions are prepared in a manner known per se, in the absence of auxiliaries for example by grinding, screening and/or compressing a solid compound of the present invention and in the presence of at least one auxiliary for example by intimately mixing and/or grinding the compound of the present invention with the auxiliary (auxiliaries).
  • auxiliaries for example by grinding, screening and/or compressing a solid compound of the present invention
  • at least one auxiliary for example by intimately mixing and/or grinding the compound of the present invention with the auxiliary (auxiliaries).
  • the grinding/milling of the compounds is to ensure specific particle size.
  • compositions for use in agriculture are emulsifiable concentrates, suspension concentrates, microemulsions, oil dispersibles, directly sprayable or dilutable solutions, spreadable pastes, dilute emulsions, soluble powders, dispersible powders, wettable powders, dusts, granules or encapsulations in polymeric substances, which comprise - at least - a compound according to the invention and the type of composition is to be selected to suit the intended aims and the prevailing circumstances.
  • suitable liquid carriers are unhydrogenated or partially hydrogenated aromatic hydrocarbons, preferably the fractions C 8 to d 2 of alkylbenzenes, such as xylene mixtures, alkylated naphthalenes or tetrahydronaphthalene, aliphatic or cycloaliphatic hydrocarbons, such as paraffins or cyclohexane, alcohols such as ethanol, propanol or butanol, glycols and their ethers and esters such as propylene glycol, dipropylene glycol ether, ethylene glycol or ethylene glycol monomethyl ether or ethylene glycol monoethyl ether, ketones, such as cyclohexanone, isophorone or diacetone alcohol, strongly polar solvents, such as N-methylpyrrolid-2-one, dimethyl sulfoxide or N,N-dimethylformamide, water, unepoxidized or epoxidized vegetable oils, such as unexpodized or e
  • solid carriers which are used for example for dusts and dispersible powders are, as a rule, ground natural minerals such as calcite, talc, kaolin, montmorillonite or attapulgite.
  • ground natural minerals such as calcite, talc, kaolin, montmorillonite or attapulgite.
  • highly disperse silicas or highly disperse absorbtive polymers are also possible to add highly disperse silicas or highly disperse absorbtive polymers.
  • Suitable particulate adsorptive carriers for granules are porous types, such as pumice, brick grit, sepiolite or bentonite, and suitable non-sorptive carrier materials are calcite or sand.
  • a large number of granulated materials of inorganic or organic nature can be used, in particular dolomite or comminuted plant residues.
  • Suitable surface-active compounds are, depending on the type of the active ingredient to be formulated, non-ionic, cationic and/or anionic surfactants or surfactant mixtures which have good emulsifying, dispersing and wetting properties.
  • the surfactants mentioned below are only to be considered as examples; a large number of further surfactants which are conventionally used in the art of formulation and suitable according to the invention are described in the relevant literature.
  • Suitable non-ionic surfactants are, especially, polyglycol ether derivatives of aliphatic or cyc- loaliphatic alcohols, of saturated or unsaturated fatty acids or of alkyl phenols which may contain approximately 3 to approximately 30 glycol ether groups and approximately 8 to approximately 20 carbon atoms in the (cyclo)aliphatic hydrocarbon radical or approximately 6 to approximately 18 carbon atoms in the alkyl moiety of the alkyl phenols.
  • the abovementioned compounds contain 1 to approximately 5 ethylene glycol units per propylene glycol unit. Examples which may be mentioned are
  • nonylphenoxypolyethoxyethanol castor oil polyglycol ether, polypropylene glycol/polyethylene oxide adducts, tributylphenoxypolyethoxyethanol, polyethylene glycol or octylphenoxypolyethoxyethanol.
  • fatty acid esters of polyoxyethylene sorbitan such as polyoxyethylene sorbitan trioleate.
  • the cationic surfactants are, especially, quarternary ammonium salts which generally have at least one alkyl radical of approximately 8 to approximately 22 C atoms as substituents and as further substituents (unhalogenated or halogenated) lower alkyl or hydroxyalkyl or benzyl radicals.
  • the salts are preferably in the form of halides, methylsulfates or ethylsulfates. Examples are
  • Suitable anionic surfactants are water-soluble soaps or water-soluble synthetic surface-active compounds.
  • suitable soaps are the alkali, alkaline earth or (unsubstituted or substituted) ammonium salts of fatty acids having approximately 10 to approximately 22 C atoms, such as the sodium or potassium salts of oleic or stearic acid, or of natural fatty acid mixtures which are obtainable for example from coconut or tall oil; mention must also be made of the fatty acid methyl taurates.
  • synthetic surfactants are used more frequently, in particular fatty sulfonates, fatty sulfates, sulfonated benzimidazole derivatives or alkylaryl sulfonates.
  • the fatty sulfonates and fatty sulfates are present as alkali, alkaline earth or (substituted or unsubstituted) ammonium salts and they generally have an alkyl radical of approximately 8 to approximately 22 C atoms, alkyl also to be understood as including the alkyl moiety of acyl radicals; examples which may be mentioned are the sodium or calcium salts of lignosulfonic acid, of the dodecylsulphuric ester or of a fatty alcohol sulfate mixture prepared from natural fatty acids. This group also includes the salts of the sulphuric esters and sulfonic acids of fatty alcohol/ethylene oxide adducts.
  • the sulfonated benzimidazole derivatives preferably contain 2 sulphonyl groups and a fatty acid radical of approximately 8 to approximately 22 C atoms. Examples of alkylarylsulfonates are the sodium, calcium or
  • triethanolammonium salts of decylbenzenesulfonic acid, of dibutyl naphthalenesulfonic acid or of a naphthalenesulfonic acid/formaldehyde condensate are also possible.
  • suitable phosphates such as salts of the phosphoric ester of a p-nonylphenol/(4-14)ethylene oxide adduct, or phospholipids.
  • the compositions comprise 0.1 to 99%, especially 0.1 to 95%, of compound according to the present invention and 1 to 99.9%, especially 5 to 99.9%, of at least one solid or liquid carrier, it being possible as a rule for 0 to 25%, especially 0.1 to 20%, of the composition to be surfactants (% in each case meaning percent by weight).
  • surfactants % in each case meaning percent by weight.
  • foliar formulation types for pre-mix compositions are:
  • WP wettable powders
  • WG water dispersable granules (powders)
  • EW emulsions, oil in water
  • SE aqueous suspo-emulsion.
  • seed treatment formulation types for pre- mix compositions are:
  • WS wettable powders for seed treatment slurry
  • WG water dispersible granules
  • CS aqueous capsule suspension.
  • formulation types suitable for tank-mix compositions are solutions, dilute emulsions, suspensions, or a mixture thereof, and dusts.
  • the methods of application such as foliar, drench, spraying, atomizing, dusting, scattering, coating or pouring, are chosen in accordance with the intended objectives and the prevailing circumstances.
  • the tank-mix compositions are generally prepared by diluting with a solvent (for example, water) the one or more pre-mix compositions containing different pesticides, and optionally further auxiliaries.
  • a solvent for example, water
  • Suitable carriers and adjuvants can be solid or liquid and are the substances ordinarily employed in formulation technology, e.g. natural or regenerated mineral substances, solvents, dispersants, wetting agents, tackifiers, thickeners, binders or fertilizers.
  • a tank-mix formulation for foliar or soil application comprises 0.1 to 20%, especially 0.1 to 15 %, of the desired ingredients, and 99.9 to 80 %, especially 99.9 to 85 %, of a solid or liquid auxiliaries (including, for example, a solvent such as water), where the auxiliaries can be a surfactant in an amount of 0 to 20 %, especially 0.1 to 15 %, based on the tank-mix formulation.
  • a pre-mix formulation for foliar application comprises 0.1 to 99.9 %, especially 1 to 95
  • auxiliaries can be a surfactant in an amount of 0 to 50 %, especially 0.5 to 40 %, based on the pre-mix formulation.
  • a tank-mix formulation for seed treatment application comprises 0.25 to 80%, especially 1 to 75 %, of the desired ingredients, and 99.75 to 20 %, especially 99 to 25 %, of a solid or liquid auxiliaries (including, for example, a solvent such as water), where the auxiliaries can be a surfactant in an amount of 0 to 40 %, especially 0.5 to 30 %, based on the tank-mix formulation.
  • auxiliaries including, for example, a solvent such as water
  • a pre-mix formulation for seed treatment application comprises 0.5 to 99.9 %, especially 1 to 95 %, of the desired ingredients, and 99.5 to 0.1 %, especially 99 to 5 %, of a solid or liquid adjuvant (including, for example, a solvent such as water), where the auxiliaries can be a surfactant in an amount of 0 to 50 %, especially 0.5 to 40 %, based on the pre-mix formulation.
  • a solid or liquid adjuvant including, for example, a solvent such as water
  • Preferred seed treatment pre-mix formulations are aqueous suspension concentrates.
  • the formulation can be applied to the seeds using conventional treating techniques and machines, such as fluidized bed techniques, the roller mill method, rotostatic seed treaters, and drum coaters. Other methods, such as spouted beds may also be useful.
  • the seeds may be presized before coating. After coating, the seeds are typically dried and then transferred to a sizing machine for sizing. Such procedures are known in the art.
  • the compounds of the present invention are particularly suited for use in soil and seed treatment applications.
  • the pre-mix compositions of the invention contain 0.5 to 99.9 especially 1 to 95, advantageously 1 to 50 , %, by mass of the desired ingredients, and 99.5 to 0.1 , especially 99 to 5, %, by mass of a solid or liquid adjuvant (including, for example, a solvent such as water), where the auxiliaries (or adjuvant) can be a surfactant in an amount of 0 to 50, especially 0.5 to 40, %, by mass based on the mass of the pre-mix formulation.
  • a solid or liquid adjuvant including, for example, a solvent such as water
  • a compound of the formula (I) in a preferred embodiment, independent of any other embodiments, is in the form of a plant propagation material treating (or protecting) composition, wherein said plant propagation material protecting composition may comprises additionally a colouring agent.
  • the plant propagation material protecting composition or mixture may also comprise at least one polymer from water-soluble and water-dispersible film-forming polymers that improve the adherence of the active ingredients to the treated plant propagation material, which polymer generally has an average molecular weight of at least 10,000 to about 100,000.
  • Examples of application methods for the compounds of the invention and compositions thereof, that is the methods of controlling pests in the agriculture, are spraying, atomizing, dusting, brushing on, dressing, scattering or pouring - which are to be selected to suit the intended aims of the prevailing circumstances.
  • the active ingredient can reach the plants via the root system (systemic action), by applying the compound to the locus of the plants, for example by application of a liquid composition of the compound into the soil (by drenching), or by applying a solid form of the compound in the form of granules to the soil (soil application).
  • systemic action by applying the compound to the locus of the plants, for example by application of a liquid composition of the compound into the soil (by drenching), or by applying a solid form of the compound in the form of granules to the soil (soil application).
  • granules can be metered into the flooded paddy-field.
  • the application of the compounds of the present invention to the soil is a preferred application method.
  • Typical rates of application per hectare is generally 1 to 2000 g of active ingredient per hectare, in particular 10 to 1000 g/ha, preferably 10 to 600 g/ha, such as 50 to 300 g/ha.
  • the compounds of the invention and compositions thereof are also suitable for the protection of plant propagation material, for example seeds, such as fruit, tubers or kernels, or nursery plants, against pests of the abovementioned type.
  • the propagation material can be treated with the compound prior to planting, for example seed can be treated prior to sowing.
  • the compound can be applied to seed kernels (coating), either by soaking the kernels in a liquid composition or by applying a layer of a solid composition. It is also possible to apply the compositions when the propagation material is planted to the site of application, for example into the seed furrow during drilling.
  • Typical treatment rates would depend on the plant and pest/fungi to be controlled and are generally between 1 to 200 grams per 100 kg of seeds, preferably between 5 to 150 grams per 100 kg of seeds, such as between 10 to 100 grams per 100 kg of seeds.
  • the application of the compounds of the present invention to seeds is a preferred application method.
  • seed embraces seeds and plant propagules of all kinds including but not limited to true seeds, seed pieces, suckers, corns, bulbs, fruit, tubers, grains, rhizomes, cuttings, cut shoots and the like and means in a preferred embodiment true seeds.
  • the present invention also comprises seeds coated or treated with or containing a compound of formula (I).
  • coated or treated with and/or containing generally signifies that the active ingredient is for the most part on the surface of the seed at the time of application, although a greater or lesser part of the ingredient may penetrate into the seed material, depending on the method of application.
  • the seed product When the said seed product is (re)planted, it may absorb the active ingredient.
  • the present invention makes available a plant propagation material adhered thereto with a compound of formula (I). Further, it is hereby made available, a composition comprising a plant propagation material treated with a compound of formula (I).
  • Seed treatment comprises all suitable seed treatment techniques known in the art, such as seed dressing, seed coating, seed dusting, seed soaking and seed pelleting.
  • the seed treatment application of the compound formula (I), which is a preferred application method, can be carried out by any known methods, such as spraying or by dusting the seeds before sowing or during the sowing/planting of the seeds.
  • Suitable target plants are, in particular, cereals, such as wheat, barley, rye, oats, rice, maize or sorghum; beet, such as sugar or fodder beet; fruit, for example pomaceous fruit, stone fruit or soft fruit, such as apples, pears, plums, peaches, almonds, cherries or berries, for example strawberries, raspberries or blackberries; leguminous plants, such as beans, lentils, peas or soya; oil plants, such as oilseed rape, mustard, poppies, olives, sunflowers, coconut, castor, cocoa or ground nuts; cucurbits, such as pumpkins, cucumbers or melons; fibre plants, such as cotton, flax, hemp or jute; citrus fruit, such as oranges, lemons, grapefruit or tangerines; vegetables, such as spinach, lettuce, asparagus, cabbages, carrots, onions, tomatoes, potatoes or bell peppers; Lauraceae, such as avocado, Cinnamonium or camphor; and also tobacco, nuts,
  • the plant is selected from cereals, corn, soybean, rice, sugarcane, vegetables and oil plants.
  • plant is to be understood as including also plants which have been so transformed by the use of recombinant DNA techniques that they are capable of synthesising one or more selectively acting toxins, such as are known, for example, from toxin-producing bacteria, especially those of the genus Bacillus and also plants which have been selected or hybridised to preserve and / or attain a desired trait, such as insect, fungi and /or nematode resistance.
  • selectively acting toxins such as are known, for example, from toxin-producing bacteria, especially those of the genus Bacillus and also plants which have been selected or hybridised to preserve and / or attain a desired trait, such as insect, fungi and /or nematode resistance.
  • Toxins that can be expressed by such transgenic plants include, for example, insecticidal proteins from Bacillus cereus or Bacillus popilliae; or insecticidal proteins from Bacillus thuringiensis, such as ⁇ -endotoxins, e.g. CrylAb, CrylAc, Cryl F, Cry1 Fa2, Cry2Ab, Cry3A, Cry3Bb1 or Cry9C, or vegetative insecticidal proteins (Vip), e.g. Vip1 , Vip2, Vip3 or Vip3A; or insecticidal proteins of bacteria colonising nematodes, for example Photorhabdus spp.
  • insecticidal proteins from Bacillus cereus or Bacillus popilliae such as ⁇ -endotoxins, e.g. CrylAb, CrylAc, Cryl F, Cry1 Fa2, Cry2Ab, Cry3A, Cry3Bb1 or Cry9C, or vegetative insecticidal proteins
  • Xenorhabdus spp. such as Photorhabdus luminescens, Xenorhabdus nematophilus
  • toxins produced by animals such as scorpion toxins, arachnid toxins, wasp toxins and other insect-specific neurotoxins
  • toxins produced by fungi such as Streptomycetes toxins, plant lectins, such as pea lectins, barley lectins or snowdrop lectins;
  • agglutinins agglutinins
  • proteinase inhibitors such as trypsin inhibitors, serine protease inhibitors, patatin, cystatin, papain inhibitors
  • ribosome-inactivating proteins RIP
  • steroid metabolism enzymes such as 3-hydroxysteroidoxidase, ecdysteroid-UDP-glycosyl- transferase, cholesterol oxidases, ecdysone inhibitors, HMG-COA-reductase, ion channel blockers, such as blockers of sodium or calcium channels, juvenile hormone esterase, diuretic hormone receptors, stilbene synthase, bibenzyl synthase, chitinases and glucanases.
  • proteinase inhibitors such as trypsin inhibitors, serine protease inhibitors, patatin, cystatin, papain inhibitors
  • RIP ribosome-inactivating proteins
  • steroid metabolism enzymes such as 3-hydroxy
  • ⁇ -endotoxins for example CrylAb, CrylAc, Cryl F, Cry1 Fa2, Cry2Ab, Cry3A, Cry3Bb1 or Cry9C, or vegetative insecticidal proteins (Vip), for example Vip1 , Vip2, Vip3 or Vip3A, expressly also hybrid toxins, truncated toxins and modified toxins.
  • Hybrid toxins are produced recombinantly by a new combination of different domains of those proteins (see, for example, WO 02/15701 ).
  • Truncated toxins for example a truncated Cry1 Ab, are known.
  • modified toxins one or more amino acids of the naturally occurring toxin are replaced.
  • amino acid replacements preferably non-naturally present protease recognition sequences are inserted into the toxin, such as, for example, in the case of Cry3A055, a cathepsin-G-recognition sequence is inserted into a Cry3A toxin (see WO 03/018810).
  • Examples of such toxins or transgenic plants capable of synthesising such toxins are disclosed, for example, in EP-A-0 374 753, WO 93/07278, WO 95/34656, EP-A-0 427 529, EP-A-451 878 and WO 03/052073.
  • Cryl-type deoxyribonucleic acids and their preparation are known, for example, from WO 95/34656, EP-A-0 367 474, EP-A-0 401 979 and WO 90/13651 .
  • the toxin contained in the transgenic plants imparts to the plants tolerance to harmful insects.
  • insects can occur in any taxonomic group of insects, but are especially commonly found in the beetles (Coleoptera), two-winged insects (Diptera) and butterflies (Lepidoptera).
  • Transgenic plants containing one or more genes that code for an insecticidal resistance and express one or more toxins are known and some of them are commercially available. Examples of such plants are: YieldGard® (maize variety that expresses a Cry1 Ab toxin); YieldGard Rootworm® (maize variety that expresses a Cry3Bb1 toxin); YieldGard Plus® (maize variety that expresses a Cry1 Ab and a Cry3Bb1 toxin); Starlink® (maize variety that expresses a Cry9C toxin); Herculex I® (maize variety that expresses a Cry1 Fa2 toxin and the enzyme phosphinothricine N-acetyltransferase (PAT) to achieve tolerance to the herbicide glufosinate ammonium); NuCOTN 33B® (cotton variety that expresses a Cry1 Ac toxin); Bollgard I® (cotton variety that expresses
  • transgenic plants are:
  • Bt1 1 Maize from Syngenta Seeds SAS, Chemin de I'Hobit 27, F-31 790 St. Sauveur, France, registration number C/FR/96/05/10. Genetically modified Zea mays which has been rendered resistant to attack by the European corn borer (Osthnia nubilalis and Sesamia nonaghoides) by transgenic expression of a truncated Cry1 Ab toxin. Bt1 1 maize also transgenically expresses the enzyme PAT to achieve tolerance to the herbicide glufosinate ammonium.
  • MIR604 Maize from Syngenta Seeds SAS, Chemin de I'Hobit 27, F-31 790 St. Sauveur, France, registration number C/FR/96/05/10. Maize which has been rendered insect-resistant by transgenic expression of a modified Cry3A toxin. This toxin is Cry3A055 modified by insertion of a cathepsin-G-protease recognition sequence. The preparation of such transgenic maize plants is described in WO 03/018810.
  • MON 863 Maize from Monsanto Europe S.A. 270-272 Avenue de Tervuren, B-1 150 Brussels, Belgium, registration number C/DE/02/9. MON 863 expresses a Cry3Bb1 toxin and has resistance to certain Coleoptera insects.
  • NK603 x MON 810 Maize from Monsanto Europe S.A. 270-272 Avenue de Tervuren, B-1 150 Brussels, Belgium, registration number C/GB/02/M3/03. Consists of conventionally bred hybrid maize varieties by crossing the genetically modified varieties NK603 and MON 810. NK603 ⁇ MON 810
  • Lepidoptera include the European corn borer.
  • Compounds of this invention are effective for controlling nematode, insect, acarid pests and/or fungal pathogens of agronomic plants, both growing and harvested, when employed alone, they may also be used in combination with other biological active agents used in agriculture, such as one or more nematicides, insecticides, acaricides, fungicides, bactericides, plant activator, molluscicide, and pheromones (whether chemical or biological). Mixing the compounds of the invention or the compositions thereof in the use form as pesticides with other pesticides frequently results in a broader pesticidal spectrum of action.
  • formula (I) compounds of this invention may be used effectively in conjunction or combination with pyrethroids, neonicotinoids, macrolides, diamides, phosphates, carbamates, cyclodienes, formamidines, phenol tin compounds, chlorinated
  • hydrocarbons benzoylphenyl ureas, pyrroles and the like.
  • compositions according to the invention can be broadened considerably, and adapted to prevailing circumstances, by adding, for example, one or more insecticidally, acaricidally, nematicidally and/or fungicidally active agents.
  • the combinations compounds of formula (I) with other insecticidally, acaricidally, nematicidally and/or fungicidally active agents may also have further surprising advantages which can also be described, in a wider sense, as synergistic activity. For example, better tolerance by plants, reduced phytotoxicity, pests or fungi can be controlled in their different development stages or better behaviour during their production, for example during grinding or mixing, during their storage or during their use.
  • TX means a compound of the formula (I), preferably a compound selected from the compounds described in Tables 1 to 1 1 shown above and, more preferably, Table A shown below):
  • an adjuvant selected from the group of substances consisting of petroleum oils (alternative name) (628) + TX,
  • an acaricide selected from the group of substances consisting of 1 ,1 -bis(4-chlorophenyl)-2- ethoxyethanol (lUPAC name) (910) + TX, 2,4-dichlorophenyl benzenesulfonate (lUPAC/Chemical Abstracts name) (1059) + TX, 2-fluoro-A/-methyl-A/-1 -naphthylacetamide (lUPAC name) (1295) + TX, 4-chlorophenyl phenyl sulfone (lUPAC name) (981 ) + TX, abamectin (1 ) + TX, acequinocyl (3) + TX, acetoprole [CCN] + TX, acrinathrin (9) + TX, aldicarb (16) + TX, aldoxycarb (863) + TX, alpha- cypermethrin (202) + TX, amidithion (870) + T
  • TX isopropyl 0-(methoxyaminothiophosphoryl)salicylate (lUPAC name) (473) + TX, ivermectin (alternative name) [CCN] + TX, jasmolin I (696) + TX, jasmolin II (696) + TX, jodfenphos (1248) + TX, lindane (430) + TX, lufenuron (490) + TX, malathion (492) + TX, malonoben (1254) + TX, mecarbam (502) + TX, mephosfolan (1261 ) + TX, mesulfen (alternative name) [CCN] + TX, methacrifos (1266) + TX, methamidophos (527) + TX, methidathion (529) + TX, methiocarb (530) + TX, methomy
  • an algicide selected from the group of substances consisting of bethoxazin [CCN] + TX, copper dioctanoate (lUPAC name) (170) + TX, copper sulfate (172) + TX, cybutryne [CCN] + TX, dichlone (1052) + TX, dichlorophen (232) + TX, endothal (295) + TX, fentin (347) + TX, hydrated lime [CCN] + TX, nabam (566) + TX, quinoclamine (714) + TX, quinonamid (1379) + TX, simazine (730) + TX, triphenyltin acetate (lUPAC name) (347) and triphenyltin hydroxide (lUPAC name) (347) + TX,
  • an anthelmintic selected from the group of substances consisting of abamectin (1 ) + TX, crufomate (101 1 ) + TX, doramectin (alternative name) [CCN] + TX, emamectin (291 ) + TX, emamectin benzoate (291 ) + TX, eprinomectin (alternative name) [CCN] + TX, ivermectin (alternative name) [CCN] + TX, milbemycin oxime (alternative name) [CCN] + TX, moxidectin (alternative name) [CCN] + TX, piperazine [CCN] + TX, selamectin (alternative name) [CCN] + TX, spinosad (737) and thiophanate (1435) + TX,
  • an avicide selected from the group of substances consisting of chloralose (127) + TX, endrin
  • a soil sterilant selected from the group of substances consisting of iodomethane (lUPAC name) (542) and methyl bromide (537) + TX,
  • a chemosterilant selected from the group of substances consisting of apholate [CCN] + TX, bisazir (alternative name) [CCN] + TX, busulfan (alternative name) [CCN] + TX, diflubenzuron (250) + TX, dimatif (alternative name) [CCN] + TX, hemel [CCN] + TX, hempa [CCN] + TX, metepa [CCN] + TX, methiotepa [CCN] + TX, methyl apholate [CCN] + TX, morzid [CCN] + TX, penfluron (alternative name) [CCN] + TX, tepa [CCN] + TX, thiohempa (alternative name) [CCN] + TX, thiotepa (alternative name) [CCN] + TX, tretamine (alternative name) [CCN] and
  • an insect repellent selected from the group of substances consisting of 2-(octylthio)ethanol (lUPAC name) (591 ) + TX, butopyronoxyl (933) + TX, butoxy(polypropylene glycol) (936) + TX, dibutyl adipate (lUPAC name) (1046) + TX, dibutyl phthalate (1047) + TX, dibutyl succinate (lUPAC name) (1048) + TX, diethyltoluamide [CCN] + TX, dimethyl carbate [CCN] + TX, dimethyl phthalate [CCN] + TX, ethyl hexanediol (1 137) + TX, hexamide [CCN] + TX, methoquin-butyl (1276) + TX,
  • an insecticide selected from the group of substances consisting of 1 -dichloro-1 -nitroethane (lUPAC/Chemical Abstracts name) (1058) + TX, 1 ,1 -dichloro-2,2-bis(4-ethylphenyl)ethane (lUPAC name) (1056), + TX, 1 ,2-dichloropropane (lUPAC/Chemical Abstracts name) (1062) + TX, 1 ,2- dichloropropane with 1 ,3-dichloropropene (lUPAC name) (1063) + TX, 1 -bromo-2-chloroethane (lUPAC/Chemical Abstracts name) (916) + TX, 2,2,2-trichloro-1 -(3,4-dichlorophenyl)ethyl acetate (lUPAC name) (1451 ) + TX, 2,2-dichlorovinyl 2-ethylsulphinylethyl methyl
  • polychlorodicyclopentadiene isomers (lUPAC name) (1346) + TX, polychloroterpenes (traditional name) (1347) + TX, potassium arsenite [CCN] + TX, potassium thiocyanate [CCN] + TX, prallethrin (655) + TX, precocene I (alternative name) [CCN] + TX, precocene II (alternative name) [CCN] + TX, precocene III (alternative name) [CCN] + TX, primidophos (1349) + TX, profenofos (662) + TX, profluthrin [CCN] + TX, promacyl (1354) + TX, promecarb (1355) + TX, propaphos (1356) + TX, propetamphos (673) + TX, propoxur (678) + TX, prothidathion (1360) + TX, prothiofo
  • a molluscicide selected from the group of substances consisting of bis(tributyltin) oxide (lUPAC name) (913) + TX, bromoacetamide [CCN] + TX, calcium arsenate [CCN] + TX, cloethocarb (999) + TX, copper acetoarsenite [CCN] + TX, copper sulfate (172) + TX, fentin (347) + TX, ferric phosphate (lUPAC name) (352) + TX, metaldehyde (518) + TX, methiocarb (530) + TX, niclosamide (576) + TX, niclosamide-olamine (576) + TX, pentachlorophenol (623) + TX, sodium pentachlorophenoxide (623) + TX, tazimcarb (1412) + TX, thiodicarb (799) + TX, tributyltin oxide (913)
  • a nematicide selected from the group of substances consisting of AKD-3088 (compound code)
  • development code (development code) (423) + TX, heterophos [CCN] + TX, iodomethane (lUPAC name) (542) + TX, isamidofos (1230) + TX, isazofos (1231 ) + TX, ivermectin (alternative name) [CCN] + TX, kinetin (alternative name) (210) + TX, mecarphon (1258) + TX, metam (519) + TX, metam-potassium
  • a nitrification inhibitor selected from the group of substances consisting of potassium ethylxanthate [CCN] and nitrapyrin (580) + TX,
  • a plant activator selected from the group of substances consisting of acibenzolar (6) + TX, acibenzolar-S-methyl (6) + TX, probenazole (658) and Reynoutha sachalinensis extract (alternative name) (720) + TX,
  • a rodenticide selected from the group of substances consisting of 2-isovalerylindan-1 ,3-dione
  • a synergist selected from the group of substances consisting of 2-(2-butoxyethoxy)ethyl piperonylate (lUPAC name) (934) + TX, 5-(1 ,3-benzodioxol-5-yl)-3-hexylcyclohex-2-enone (lUPAC name) (903) + TX, farnesol with nerolidol (alternative name) (324) + TX, MB-599 (development code) (498) + TX, MGK 264 (development code) (296) + TX, piperonyl butoxide (649) + TX, piprotal (1343) + TX, propyl isomer (1358) + TX, S421 (development code) (724) + TX, sesamex (1393) + TX, sesasmolin (1394) and sulfoxide (1406) + TX,
  • an animal repellent selected from the group of substances consisting of anthraquinone (32) + TX, chloralose (127) + TX, copper naphthenate [CCN] + TX, copper oxychloride (171 ) + TX, diazinon (227) + TX, dicyclopentadiene (chemical name) (1069) + TX, guazatine (422) + TX, guazatine acetates (422) + TX, methiocarb (530) + TX, pyridin-4-amine (lUPAC name) (23) + TX, thiram (804) + TX, trimethacarb (840) + TX, zinc naphthenate [CCN] and ziram (856) + TX,
  • a virucide selected from the group of substances consisting of imanin (alternative name) [CCN] and ribavirin (alternative name) [CCN] + TX,
  • a wound protectant selected from the group of substances consisting of mercuric oxide (512) +
  • azaconazole 60207- 31 -0] + TX, bitertanol [70585-36-3] + TX, bromuconazole [1 16255-48-2] + TX, cyproconazole [94361 - 06-5] + TX, difenoconazole [1 19446-68-3] + TX, diniconazole [83657-24-3] + TX, epoxiconazole
  • the mass ratio of of any two ingredients in each combination is selected as to give the desired, for example, synergistic action. In general, the mass ratio would vary depending on the specific ingredient and how many ingredients are present in the combination. Generally, the mass ratio between any two ingredients in any combination of the present invention, independently of one another, is from 100:1 to 1 :100, including from 99:1 , 98:2, 97:3, 96:4, 95:5, 94:6, 93:7, 92:8, 91 :9, 90:10, 89:1 1 , 88:12, 87:13, 86:14, 85:15, 84:16, 83:17, 82:18, 81 :19, 80:20, 79:21 , 78:22, 77:23, 76:24, 75:25, 74:26, 73:27, 72:28, 71 :29, 70:30, 69:31 , 68:32, 67:33, 66:34, 65:45
  • Preferred mass ratios between any two components of present invention are from 75:1 to 1 :75, more preferably, 50:1 to 1 .50, especially 25:1 to 1 :25, advantageously 10:1 to 1 :10, such as 5:1 to 1 :5, for example 1 :3 to 3:1 .
  • the mixing ratios are understood to include, on the one hand, ratios by mass and also, on other hand, molar ratios.
  • combinations of the present invention i.e. those comprising a compound of the present invention and one or more other biological active agents
  • the ingredients of a combination are applied sequentially (i.e., one after the other), the ingredients are applied sequentially within a reasonable period of each other to attain the biological performance, such as within a few hours or days.
  • the order of applying the ingredients in the combination i.e., whether the compounds of formula (I) should be applied first or not is not essential for working the present invention.
  • the event ingredients of the combinations are applied simultaneously in the present invention, they may be applied as a composition containing the combination, in which case (A) the compound of formula (I) and the one or more other ingredients in the combinations can be obtained from separate formulation sources and mixed together (known as a tank-mix, ready-to-apply, spray broth, or slurry), or (B) the compound of formula (I) and the one or more other ingredients can be obtained as single formulation mixture source (known as a pre-mix, ready-mix, concentrate, or formulated product).
  • A the compound of formula (I) and the one or more other ingredients in the combinations can be obtained from separate formulation sources and mixed together (known as a tank-mix, ready-to-apply, spray broth, or slurry), or
  • B) the compound of formula (I) and the one or more other ingredients can be obtained as single formulation mixture source (known as a pre-mix, ready-mix, concentrate, or formulated product).
  • a compound according to the present invention is applied as a combination. Accordingly, the present invention also provides a composition comprising a a compound according the invention as herein described and one or more other biological active agents, and optionally one or more customary formulation auxiliaries; which may be in the form of a tank-mix or pre-mix composition.
  • the compounds of formula (I) are particularly useful for controlling and preventing helminth and nemtode endo- and ectoparasitic infestations and infections in warm-blooded animals such as cattle, sheep, swine, camels, deer, horses, poultry, fish, rabbits, goats, mink, fox, chinchillas, dogs and cats as well as humans.
  • compounds of invention are especially useful for the control of helminths and nematodes.
  • helminths are members of the class Trematoda, commonly known as flukes or flatworms, especially members of the genera Fasciola, Fascioloides, Paramphistomu, Dicrocoelium, Eurytrema, Ophisthorchis, Fasciolopsis, Echinostoma and Paragonimus.
  • Nematodes which can be controlled by the formula (I) compounds include the genera Haemonchus, Ostertagia, Cooperia, Oesphagastomu, Nematodirus, Dictyocaulus, Trichuris, Dirofilaria, Ancyclostoma, Ascaria and the like.
  • the compounds of the invention may be formulated as animal feeds, animal feed premixes, animal feed concentrates, pills, solutions, pastes, suspensions, drenches, gels, tablets, boluses and capsules.
  • the compounds of the invention may be administered to the animals in their drinking water.
  • the dosage form chosen should provide the animal with about 0.01 mg/kg to 100 g/kg of animal body weight per day of the compound of the invention.
  • the compounds of the invention may be administered to animals parenterally, for example, by intraruminal, intramuscular, intravenous or subcutaneous injection.
  • the compounds of the invention may be dispersed or dissolved in a physiologically acceptable carrier for subcutaneous injection.
  • the compounds of the invention may be formulated into an implant for subcutaneous administration.
  • the compounds of the invention may be transdermal ⁇ administered to animals.
  • the dosage form chosen should provide the animal with about 0.01 mg/kg to 100 mg/kg of animal body weight per day of the compound of the invention.
  • the compounds of the invention may also be applied topically to the animals in the form of dips, dusts, powders, collars, medallions, sprays and pour-on formulations.
  • dips and sprays usually contain about 0.5 ppm to 5,000 ppm and preferably about 1 ppm to 3,000 ppm of the compound of the invention.
  • the compounds of the invention may be formulated as ear tags for animals, particularly quadrupeds such as cattle and sheep.
  • a compound of formula (I) is a anti- helminth compound.
  • a compound of formula (I) is a pesticidal compound, preferably a nematicidal compound.
  • Step 1 2-(2-fluoro-4-trifluoromethyl-phenyl)-ethylamine
  • Step 2 N-[2-(2-fluoro-4-trifluoromethyl-phenyl)-ethyl1-2-trifluoromethyl-nicotinamide (Compound A.001 )
  • Step 1 (4-Chloro- -fluoro-phenyl)-acetonitrile
  • Solvent degasser binary pump, heated column compartment and diode-array detector.
  • Filter papers (9 cm x 4.5 cm) with a small pocket were placed into plastic pouches (12 cm x 6 cm ).
  • One cucumber cv. Toshka seed was placed in the centre of the filter paper pocket of all the pouches needed for a test.
  • the cucumber seeds in the pouches were treated with test solutions at 200 ppm by pipetting the solution directly over the cucumber seed in the filter paper pocket in the pouch.
  • the compound solution was prepared at twice the concentration required and the egg suspension is prepared with FORL nutrient solution with 3000 eggs/ 0.5 ml. After applying all the treatments, 3000 eggs (in 0.5 ml of FORL nutrient solution) were pipetted into the pouches.
  • the pouches were incubated in a moist chamber for twelve days and watered regularly to maintain good filter paper moisture essential for the growing cucumber root system. After this period, the filter paper containing the germinated cucumber seedling was removed from the plastic pouch to assess the number of galls caused by Meloidogyne spp. per root system.
  • the following compounds showed a greater than 80% reduction of galling compared to the untreated control: A.001 , A.002, A.003, A.004 and A.010.
  • the following compounds showed a greater than 80% reduction of galling compared to the untreated control: A.001 , A.002, A.003, A.004 and A.010.
  • Heterodera schachtii Sudgar beet cyst nematode
  • the tested application rate of each compound was 200 ppm. All solutions were brought to a concentration of 400 ppm, respectively, as they were subseguently diluted by adding the eguivalent amount of water containing juvenile nematodes. After preparation of the suspensions, 1 ml of each suspension and concentration was transferred to 16-well assay plates with a total of three replicates per treatment. Approximately 500 juveniles of Heterodera schachtii were added in 1 ml of water to each well. Nematodes in water served as controls. The plates were placed in a dark box and stored at room temperature. Nematode paralysis was determined after 24 hours incubation at 25°C in darkness.
  • the following compounds showed a greater than 75% nematode immobilization compared to the untreated control: A.001 , A.002, A.004 and A.010.

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Abstract

L'invention concerne des composés représentés par la formule (I) dans laquelle les substituants sont tels que définis dans la revendication 1. Ces composés sont appropriés pour être utilisés en tant que nématicides.
PCT/EP2014/064511 2013-07-12 2014-07-08 Dérivés de nicotinamide et utilisation de ces derniers contre les nématodes WO2015004091A1 (fr)

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CN107987012A (zh) * 2018-01-29 2018-05-04 田元强 一种4-苄基哌啶类酰胺化合物及其在防治植物线虫病害中的应用

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