WO2014173921A1 - Carboxamides utilisés en tant que composés pesticides - Google Patents

Carboxamides utilisés en tant que composés pesticides Download PDF

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WO2014173921A1
WO2014173921A1 PCT/EP2014/058177 EP2014058177W WO2014173921A1 WO 2014173921 A1 WO2014173921 A1 WO 2014173921A1 EP 2014058177 W EP2014058177 W EP 2014058177W WO 2014173921 A1 WO2014173921 A1 WO 2014173921A1
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ccn
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PCT/EP2014/058177
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Thomas Pitterna
Olivier Loiseleur
Torsten LUKSCH
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
    • A01N43/48—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with two nitrogen atoms as the only ring hetero atoms
    • A01N43/54—1,3-Diazines; Hydrogenated 1,3-diazines
    • 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
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/48—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with two nitrogen atoms as the only ring hetero atoms
    • A01N43/60—1,4-Diazines; Hydrogenated 1,4-diazines
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D401/00—Heterocyclic 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
    • C07D401/02—Heterocyclic 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
    • C07D401/12—Heterocyclic 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

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.
  • Novel carboxamides containing a substituted cyclopropyl moiety have now been found, which show good pesticidal, in particular nematicidal, activity.
  • the present invention thus relates to a compound of the formula I
  • R5 is pyridyl, which is substituted by one R5a, and, optionally, by one or more R5b;
  • R5a is C2-C6-alkenyl substituted by one or more R5x, or C2-C6 alkynyl substituted by one or more R5x;
  • R5b is, independently of each other, halogen, or C1 -C4-haloalkyl
  • R5x is, independently of each other, halogen
  • R6 is hydrogen or C1 -C2-alkyl
  • A1 , A2, A3, A4 and A5 are, independently of each other, N, C-H or C-X, wherein the number of N atoms in the ring containing A1 , A2, A3, A4 and A5 is 0, 1 or 2;
  • X is a halogen, nitrile, C1 -C4-alkyl, or C1 -C4-haloalkyl;
  • 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 ie f-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 (£)- or (Z)-configuration.
  • Alkenyl and alkynyl moieties can contain one or more double and/or triple bonds in any combination.
  • 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, FCH 2 , CICH 2 , BrCH 2 , CHsCHF, (CH 3 ) 2 CF, CF 3 CH 2 or CHF 2 CH 2 .
  • A1 and A4 are, independently of each other, N, C-H or C-X and A2, A3 and A5 are, independently of each other, C-H or C- X.
  • A1 and A4 are, independently of each other, N, C-H or C-X; A2 and A3 are C-H; and A5 is C-H or C-X.
  • the ring containing A1 , A2, A3, A4 and A5 is selected from 3-chloro-2-pyrazinyl, 3-chloro-2-pyridyl, 3-trifluoromethyl-2-pyridyl, 2-trifluoromethylphenyl, 2-chloro-3-pyridyl, 2,6-difluorophenyl, 3-fluoro-2-pryidyl, 3-methyl- 2-pyridyl, 3-trifluoro-2-pyrazinyl, 2-trifluoromethyl-3-pyridyl, 2-chlorophenyl, 3-bromo-2- pyrazinyl, 3-methyl-2-pyrazinyl, 2-methyl-3-pyridyl, as illustrated below.
  • A1 , A2, A3, A4 and A5 form a ring selected from 2-trifluoromethylphenyl, 3-chloro-2-pyrazinyl, 3-chloro-2-pyridyl, 3- trifluoromethyl-2-pyridyl, 3-trifluoro-2-pyrazinyl and 2-trifluoromethyl-3-pyridyl.
  • A1 , A2, A3, A4 and A5 form a ring selected from 2-trifluoromethylphenyl, 3-chloro-2-pyrazinyl, 3-trifluoro-2-pyrazinyl, 2- trifluoromethyl-3-pyridyl.
  • X is a halogen or C1 -C4-haloalkyl.
  • R5 is pyridyl, which is substituted by one R5a.
  • R5 is pyridyl, which is substituted by one R5a and by one R5b.
  • R5 is 2-pyridyl, which is substituted by one R5a and by one R5b.
  • R5 is R 5 '
  • R5 is 3-chloro-5-[1 - (trifluoromethyl)vinyl]-2-pyridyl, 3-chloro-5-(3,3,3-trifluoroprop-1 -ynyl)-2-pyridyl, 3-chloro-5- [(E)-3,3,3-trifluoroprop-1 -enyl]-2-pyridyl, 3-chloro-5-(2,2-dibromovinyl)-2-pyridyl, 3-chloro-5- (2,2-dichlorovinyl)-2-pyridyl, 3-chloro-5-(2,2-difluorovinyl)-2-pyridyl, 3-chloro-5-[(E)-1 ,2- difluorovinyl]-2-pyridyl, 3-chloro-5-(1 ,2,2-trifluorovinyl)-2-pyridyl, 3-chloro-5-(1 -fluor
  • R5 is 3-chloro-5-(3,3,3- trifluoroprop-1 -ynyl)-2-pyridyl, 3-chloro-5-[(E)-3,3,3-trifluoroprop-1 -enyl]-2-pyridyl, 3-chloro- 5-(2,2-dibromovinyl)-2-pyridyl.
  • R5a is C2-C4-alkenyl substituted by one R5x, or C2-C4 alkynyl substituted by one R5x.
  • R5b is chloro, fluoro, bromo or C1 - C2-haloalkyl.
  • R5b is chloro, fluoro or bromo. In an embodiment, independent of other embodiments, R5b is chloro.
  • R5x is chloro, fluoro, bromo .
  • R6 is hydrogen or methyl. In an embodiment, independent of other embodiments, R6 is hydrogen.
  • A1 , A2, A3, A4 and A5 form a ring selected from 2-trifluoromethylphenyl, 3-chloro-2-pyrazinyl, 3-chloro-2-pyridyl, 3- trifluoromethyl-2-pyridyl, 3-trifluoro-2-pyrazinyl, 2-trifluoromethyl-3-pyridyl,
  • R5 is 3-chloro-5- [1 -(trifluoromethyl)vinyl]-2-pyridyl, 3-chloro-5-(3,3,3-trifluoroprop-1 -ynyl)-2-pyridyl, 3-chloro- 5-[(E)-3,3,3-trifluoroprop-1 -enyl]-2-pyridyl, 3-chloro-5-(2,2-dibromovinyl)-2-pyridyl, 3-chloro- 5-(2,2-dichlorovinyl)-2-pyridyl, 3-
  • A1 , A2, A3, A4 and A5 form a ring selected from 2-trifluoromethylphenyl, 3-chloro-2-pyrazinyl, 3-trifluoro-2-pyrazinyl, 2- trifluoromethyl-3-pyridyl, R5 is 3-chloro-5-(3,3,3-trifluoroprop-1 -ynyl)-2-pyridyl, 3-chloro-5- [(E)-3,3,3-trifluoroprop-1 -enyl]-2-pyridyl, 3-chloro-5-(2,2-dibromovinyl)-2-pyridyl, R6 is hydrogen.
  • Compounds of formula I may be prepared by reacting a compound of formula (la), wherein pyr means pyridyl that may be further substituted with one or more R5b, and hal means chlorine, bromine, iodine or a sulfonate with a compound of the formula (lb) wherein M means a metal group such as for example -B(OH) 2 , -BF 3 " , -SnBu 3 or -ZnCI, in the presence of a catalyst, such as a palladium catalyst.
  • compounds of formula (I) can be prepared from amines of the formula (lib) and acylating agents of the formula (VII), wherein R5, R6, A1 , A2, A3, A4, and A5 are as defined herein and Xb is a leaving group. Typical leaving groups are halide, preferably chloride, and hydroxyl. When Xb is hydroxyl, (VII) is a carboxylic acid, and the reaction is preferably facilitated by an activating agent. Typical activating agents are DCC, EDCI, BOP, HBTU, BOP-CI, PyBOP as described in L. A. Paquette, Encyclopedia of Reagents for Organic Synthesis, Vol 3. Wiley, England, 1995 pp 1751 -1754. Acylating agents of the formula (VII) are known or are easily prepared by those skilled in the art.
  • Amines of the formula (I la), in which R6 is H and R5 is as defined herein, can be prepared by treating nitriles of the formula (III) with a reducing agent.
  • a typical reducing agent is hydrogen.
  • Typical catalysts are metals, metal salts, or metal complexes.
  • Other typical reducing agents are hydrides.
  • Typical hydrides are borohydrides, or aluminium hydrides, examples of which are sodium borohydride, diisobutylaluminium hydride, or lithium aluminium hydride. Such hydride reductions can be facilitated by the use of other components such as metal salts.
  • R6-Xc organometallic reagent of the formula R6-Xc followed by hydrolysis, for example with acid, such as hydrochloric acid.
  • Xd is an activating group, typically an acyl, sulfinyl or sulfonyl group.
  • Xc is a metal ion, which may or may not be coordinated with a further anion or ligand.
  • Typical R6Xc reagents are Grignard or organolithium
  • Aldehydes of the formula (VI) can be prepared by reduction of the corresponding nitriles (III) or esters, or by oxidation of the corresponding alcohols, for example, SWERN oxidation.
  • One of the reducing agents which can be used for reducing nitriles or esters to aldehydes is diisobutylaluminium hydride (DIBAL).
  • Nitriles of the formula (III), in which R5 is as defined herein can be prepared from nitriles of the formula (XI), in which R5 is as defined herein and an alkylating agent of the formula (X) in presence of a base, in which Xg is a leaving group. Typical leaving groups are halide and sulfonate. It is clear that compounds of the formula (I) can be transformed to other compounds of the formula (I) through synthetic modification of the groups R5, R6, A1 , A2, A3, A4, and A5.
  • 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
  • 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.
  • Examples which may be mentioned are 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, triethylenediamine, cyclohexylamine, N-cyclohexyl-N,N- dimethylamine, ⁇ , ⁇ -diethylaniline, pyridine, 4-(N,N-dimethylamino)pyridine, quinuclidine, N-methylmorpholine, benzyltrimethylammonium hydroxide and 1 ,8- diazabicyclo[5.4.0]undec-7-ene (DBU).
  • DBU diazabicyclo[5.4.0]undec-7-ene
  • the reactants can be reacted with each other as such, i.e. without adding a solvent or diluent. 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 N,N- 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, immobilized 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 camphor, tartaric or malic acid, or sulfonic acid, for example
  • an optically active acid such as a carboxylic acid, for example camphor, 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 diastereomers, from which the desired enantiomer can be set free by the action of suitable agents, for example basic agents.
  • 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 diastereose- lective 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.
  • Table 1 provides 8 compounds of formula (Ip), wherein A is
  • compound 1.001 has the following structure:
  • Table 2 provides 8 compounds of formula (Ip), wherein A is 2-chloro-3-pyrazinyl (A2) and R5 and R6 are as defined in each row of Table P.
  • Table 3 provides 8 compounds of formula (Ip), wherein A is 3-trifluoromethyl-2- pyridyl (A3) and R5 and R6 are as defined in each row of Table P.
  • Table 4 provides 8 compounds of formula (Ip), wherein A is 3-chloro-2-pyridyl (A4) and R5 and R6 are as defined in each row of Table P.
  • Table 5 provides 8 compounds of formula (Ip), wherein A is 2-trifluoromethyl-3 pyridyl (A5) and R5 and R6 are as defined in each row of Table P.
  • Table 6 provides 8 compounds of formula (Ip), wherein A is 2-trifluoromethyl-phenyl
  • Table 7 provides 8 compounds of formula (Ip), wherein A is 2-chloro-3-pyridyl (A7) and R5 and R6 are as defined in each row of Table P.
  • Table 8 provides 8 compounds of formula (Ip), wherein A is 2-fluoro-6-trifluoromethyl- phenyl (A8) and R5 and R6 are as defined in each row of Table P.
  • Table 9 provides 8 compounds of formula (Ip), wherein A is 2-tolyl (A9) and R5 and R6 are as defined in each row of Table P.
  • Table 10 provides 8 compounds of formula (Ip), wherein A is 2-pyrimidinyl (A10) and R5 and R6 are as defined in each row of Table P.
  • Table 1 1 provides 8 compounds of formula (Ip), wherein A is 3-methyl-2-pyridyl (A1 1 ) and R5 and R6 are as defined in each row of Table P.
  • Table 12 provides 8 compounds of formula (Ip), wherein A is 2-fluorophenyl (A12) and R5 and R6 are as defined in each row of Table P.
  • Table 13 provides 8 compounds of formula (Ip), wherein A is 2-chlorophenyl (A13) and R5 and R6 are as defined in each row of Table P.
  • Table 14 provides 8 compounds of formula (Ip), wherein A is 2-bromophenyl (A14) and R5 and R6 are as defined in each row of Table P.
  • Table 15 provides 8 compounds of formula (Ip), wherein A is 2-iodophenyl (A15) and R5 and R6 are as defined in each row of Table P.
  • Table 16 provides 8 compounds of formula (Ip), wherein A is 2,6-dichlorophenyl (A16) and R5 and R6 are as defined in each row of Table P.
  • Table 17 provides 8 compounds of formula (Ip), wherein A is 2-chloro-6-fluoro-phenyl (A17) and R5 and R6 are as defined in each row of Table P.
  • Table 18 provides 8 compounds of formula (Ip), wherein A is 2-fluoro-6-methyl- phenyl (A18) and R5 and R6 are as defined in each row of Table P.
  • Table 19 provides 8 compounds of formula (Ip), wherein A is 2-methyl-3-pyridyl (A19) and R5 and R6 are as defined in each row of Table P.
  • Table 20 provides 8 compounds of formula (Ip), wherein A is 3-fluoro-2-pyridyl (A20) and R5 and R6 are as defined in each row of Table P.
  • Table 21 provides 8 compounds of formula (Ip), wherein A is 3-methyl-2-pyrazinyl (A21 ) and R5 and R6 are as defined in each row of Table P.
  • Table 22 provides 8 compounds of formula (Ip), wherein A is 3-bromo-2-pyrazinyl (A22) and R5 and R6 are as defined in each row of Table P.
  • Table 23 provides 8 compounds of formula (Ip), wherein A is 3-trifluoromethyl-2- pyrazinyl (A23) and R5 and R6 are as defined in each row of Table P.
  • Table 24 provides 8 compounds of formula (Ip), wherein A is 5-chloro-4-pyri
  • Table 25 provides 8 compounds of formula (Ip), wherein A is 2-cyanophenyl (A25) and R5 and R6 are as defined in each row of Table P.
  • 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 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, Aphelenchoides species; Sting nematodes, Eelonolaimus longicaudatus and other Belonolaimus species; Pine
  • nematodes Bursaphelenchus xylophilus and other Bursaphelenchus species; Ring nematodes, Criconema species, Criconemella species, Criconemoides species,
  • Mesocriconema species Stem and bulb nematodes, Ditylenchus destructor, Ditylenchus dipsaci and other Ditylenchus species; Awl nematodes, Dolichodorus species; Spiral nematodes, Heliocotylenchus multicinctus and other Helicotylenchus species; Sheath and sheathoid nematodes, Hemicycliophora species and Hemicriconemoides species;
  • nematodes Nacobbus species
  • Needle nematodes Longidorus elongatus and other Longidorus species
  • Pin nematodes Pin nematodes
  • Lesion nematodes Lesion nematodes
  • Pratylenchus neglectus Pratylenchus penetrans, Pratylenchus curvitatus, Pratylenchus goodeyi and other Pratylenchus species
  • Burrowing nematodes Radopholus similis and other Radopholus species
  • Reniform nematodes Rotylenchus robustus, Rotylenchus reniformis and other Rotylenchus species
  • Scutellonema species Stubby root nematodes, Trichodorus primitivus and other Trichodorus species, Paratrichodorus species
  • Stunt nematodes Tylenchorhynchus claytoni, Tylenchorhynchus dubius and other
  • Tylenchorhynchus species Citrus nematodes, Tylenchulus species; Dagger nematodes, Xiphinema species; and other plant parasitic nematode species, such as Subanguina spp., Hypsoperine spp., Macroposthonia spp., Melinius spp., Punctodera spp., and Quinisulcius spp..
  • 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. formulation) containing a carrier.
  • 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
  • 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 Ci 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 ⁇ , ⁇ -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 cycloaliphatic 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 ethylsul- fates. Examples are stearyltrimethylammonium chloride and benzylbis(2-chloroethyl)ethyl- ammonium bromide.
  • 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 alkyi radical of approximately 8 to
  • alkyi also to be understood as including the alkyi 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.
  • alkylarylsulfonates are the sodium, calcium or triethanolammonium salts of decylbenzenesulfonic acid, of dibutylnaphthalenesulfonic acid or of a naphthalenesulfonic acid/formaldehyde condensate.
  • 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
  • a solid or liquid auxiliaries including, for example, a
  • auxiliaries can be a surfactant in an amount of
  • a pre-mix formulation for foliar application comprises 0.1 to 99.9 %, especially 1 to 95 %, of the desired ingredients, and 99.9 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 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.
  • 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
  • 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,
  • ornamentals such as flowers, amd lawn grass or turf.
  • 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.
  • 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, Cry1 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
  • insecticidal proteins from Bacillus cereus or Bacillus popilliae such as ⁇ -endotoxins, e.g. CrylAb, CrylAc, Cry1 F, Cry1 Fa2, Cry2Ab, Cry3A, Cry3Bb1 or Cry9C, or vegetative insecticidal proteins (Vip),
  • Photorhabdus spp. or Xenorhabdus spp. such as Photorhabdus luminescens
  • 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
  • proteinase inhibitors such as trypsin inhibitors, serine protease inhibitors, patatin, cystatin, papain inhibitors
  • ribosome-inactivating proteins (RIP) such as ricin, maize-RIP, abrin, luffin, saporin or bryodin
  • steroid metabolism enzymes such as 3-hydroxysteroidoxidase, ecdysteroid-UDP-glycosyl-transferase, cholesterol oxidases, ecdysone inhibitors, HMG-COA-reductase, ion channel blockers
  • ⁇ -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
  • Truncated toxins for example a truncated CrylAb
  • modified toxins one or more amino acids of the naturally occurring toxin are replaced.
  • 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 CrylAb toxin); YieldGard Rootworm® (maize variety that expresses a Cry3Bb1 toxin); YieldGard Plus® (maize variety that expresses a CrylAb 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 CrylAc toxin); Bollgard I® (cotton variety that expresses a
  • 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 (Ostrinia nubilalis and Sesamia nonagrioides) by transgenic expression of a truncated CrylAb 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 x MON 810 Maize transgenically expresses the protein CP4 EPSPS, obtained from Agrobacterium sp. strain CP4, which imparts tolerance to the herbicide Roundup® (contains glyphosate), and also a CrylAb toxin obtained from Bacillus thuringiensis subsp. kurstaki which brings about tolerance to certain 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.
  • the 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.
  • the activity of the 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.
  • 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.
  • the following list of pesticides together with which the compounds according to the invention can be used, is intended to illustrate the possible combinations by way of example.
  • TX means a compound of the formula I, preferably each compound 1 .001 to 25.008 selected from Tables 1 -25 and more preferably, compounds X.1 to X.28 from Table X, even more preferably from compounds X.1 , X.2, X.3, X.9, X.12, X.13 and X.14):
  • 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
  • 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 (1 122) + TX, fenthion (346) + TX, pyridin-4-amine (lUPAC name) (23) and strychnine (745) + TX,
  • a bactericide selected from the group of substances consisting of 1 -hydroxy-1 /-/-pyridine-2- thione (lUPAC name) (1222) + TX, 4-(quinoxalin-2-ylamino)benzenesulfonamide (lUPAC name) (748) + TX, 8-hydroxyquinoline sulfate (446) + TX, bronopol (97) + TX, copper dioctanoate (lUPAC name) (170) + TX, copper hydroxide (lUPAC name) (169) + TX, cresol [CCN] + TX, dichlorophen (232) + TX, dipyrithione (1 105) + TX, dodicin (1 1 12) + TX, fenaminosulf (1 144) + TX, formaldehyde (404) + TX, hydrargaphen (alternative name) [CCN] + TX, kasugamycin (495) + TX, kasugamycin hydrochloride
  • a biological agent selected from the group of substances consisting of Adoxophyes orana GV (alternative name) (12) + TX, Agrobacterium radiobacter (alternative name) (13) + TX, Amblyseius spp. (alternative name) (19) + TX, Anagrapha falcifera NPV (alternative name) (28) + TX, Anagrus atomus (alternative name) (29) + TX, Aphelinus abdominalis
  • 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
  • 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
  • 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
  • a nematicide selected from the group of substances consisting of AKD-3088 (compound code) + TX, 1 ,2-dibromo-3-chloropropane (lUPAC/Chemical Abstracts name) (1045) + TX, 1 ,2-dichloropropane (lUPAC/ Chemical Abstracts name) (1062) + TX, 1 ,2-dichloropropane with 1 ,3-dichloropropene (lUPAC name) (1063) + TX, 1 ,3-dichloropropene (233) + TX, 3,4- dichlorotetrahydrothiophene 1 ,1 -dioxide (lUPAC/Chemical Abstracts name) (1065) + TX, 3- (4-chlorophenyl)-5-methylrhodanine (lUPAC name) (980) + TX, 5-methyl-6-thioxo-1 ,3,5- thiadiazinan-3-ylacetic acid (lUPAC name
  • 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 Reynoutria sachalinensis extract (alternative name) (720) + TX,
  • a rodenticide selected from the group of substances consisting of 2-isovalerylindan-1 ,3- dione (lUPAC name) (1246) + TX, 4-(quinoxalin-2-ylamino)benzenesulfonamide (lUPAC name) (748) + TX, alpha-chlorohydrin [CCN] + TX, aluminium phosphide (640) + TX, antu (880) + TX, arsenous oxide (882) + TX, barium carbonate (891 ) + TX, bisthiosemi (912) + TX, brodifacoum (89) + TX, bromadiolone (91 ) + TX, bromethalin (92) + TX, calcium cyanide (444) + TX, chloralose (127) + TX, chlorophacinone (140) + TX, cholecalciferol (alternative name) (850) + TX, coumachlor (1004) + TX, coum
  • 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) +
  • 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) + TX, octhilinone (590) and thiophanate-methyl (802) + TX,
  • 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
  • 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.
  • the mass ratio between any two ingredients in any combination of the present invention 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, 64:46, 63:47, 62:48, 61 :49, 60:40, 59:41 , 58:42, 57:43, 56:44, 55:45, 54:46
  • 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.
  • the combinations of the present invention may be applied simulatenously or sequentially.
  • 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.
  • ingredients of the combinations 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. In an embodiment, independent of any other embodiments, a compound of formula (I) is a pesticidal compound, preferably a nematicidal compound.
  • reaction mixture was stirred at ambient temperature for 1 h, then the reaction mixture was poured into 800 ml of cold water and was extracted with two 1 L portions of diethyl ether. The combined organic phases were washed with brine, dried over sodium sulfate, filtered and concentrated. 29.4 g of crude material was obtained as a brown oil. It was purified by chromatography on silica gel, using heptane/ethyl acetate (9:1 ) as a eluent. Thus, 23.4 g of (5-bromo-3-chloro-pyridin-2-yl)-acetonitrile was obtained as a orange oil.
  • benzyltriethylammonium chloride was added at ambient temperature.
  • step 2 106 mg of1 -(5-bromo-3-chloro-pyridin-2-yl)-cyclopropanecarbonitrile (step 2) was dissolved in 2 ml of dichloromethane and was cooled down to -78° C. Then 0.91 ml of
  • diisobutylaluminium hydride (1 M in tetrahydrofuran) was added dropwise. The reaction mixture was stirred at -78 °C for 1 h, then at ambient temperature for three days. Then 0.40 ml of diisobutylaluminium hydride solution was added again at -78 °C and the reaction mixture was warmed to 40°C and stirred for 24 hours. The reaction mixture was poured into a saturated solution of potassium sodium tartrate and the resulting mixture was stirred for 1 hour. The aqueous phase was extracted with three 25 ml portions dichloromethane. The organic phase was dried over sodium sulfate, filtered and concentrated. 140 mg of crude material was obtained as a yellow sticky solid.
  • Step 4 N-[[1 -(5-bromo-3-chloro-2-pyridyl)cvclopropyllmethyll-3-fluoro-pyridine-2- carboxamide (Q.1 )
  • step 3 400 mg C-[1 -(5-Bromo-3-chloro-pyridin-2-yl)-cyclopropyl]-methylamine (step 3) was dissolved in 7ml dichoromethane and 0.426 ml triethylamine was added. The reaction mixture was stirred at ambient temperature and a solution of 268 mg 3-fluoropyridine-2- carbonyl chloride in 3 ml dichoromethane was added dropwise. The reaction mixture was stirred at ambient temperature for 14 hours. Then ater was added, the phases were separated and the water phase was extracted with dichoromethane. The organic phase was dried over anhydrous sodium sulfate, filtered and concentrated. Crude material was obtained as a dark sticky solid. Purification by chromatography on silica gel using
  • Step 5 N-[[1 -[3-chloro-5-[1 -(trifluoromethyl)vinyll-2-pyridyllcvclopropyllmethyll-3-fluoro- ridine-2-carboxamide (compound X.1 )
  • step 4 150 mg of N-[[1 -(5-bromo-3-chloro-2-pyridyl)cyclopropyl]methyl]-3-fluoro-pyridine-2- carboxamide (step 4), 175 mg of 1 -(trifluoromethyl)vinylboronic acid hexylene glycol ester, 0.585 ml of a 2M aqueous solution of sodium carbonate and 47 mg
  • Step 1 tert-butyl 5,6-dichloropyridine-3-carboxylate
  • Step 2 tert-butyl (6)-5-chloro-6-(1 -cvano-2-methoxy-2-oxo-ethylidene)-1 H-pyridine-3- carboxylate
  • Step 4 tert-butyl 5-chloro-6-(1 -cvanocvclopropyl)pyridine-3-carboxylate
  • Step 5 tert-butyl 6-[1 -(aminomethyl)cvclopropyll-5-chloro-pyridine-3-carboxylate
  • Step 6 tert-butyl 6-[1 -[(tert-butoxycarbonylamino)methyllcvclopropyll-5-chloro-pyridine-3- carboxylate
  • Step 7 tert-butyl N-[[1 -[3-chloro-5-(hvdroxymethyl)-2-pyridyllcvclopropyllmethyllcarbamate
  • Step 8 tert-butyl N-[[1 -(3-chloro-5-formyl-2-pyridyl)cvclopropyllmethyllcarbamate
  • Step 9 tert-butyl N-rri -i3-chloro-5-(2,2-dibromovinyl)-2- pyridyllcvclopropyllmethyllcarbamate
  • Step 10 [1 -[3-chloro-5-(2,2-dibromovinyl)-2-pyridyllcvclopropyllmethanamine
  • Step 1 1 N-[[1 -[3-chloro-5-(2,2-dibromovinyl)-2-pyridyllcvclopropyllmethyll-3-
  • acyl chloride prepared from 3-trifluoromethylpyridine-2-carboxylic acid (0.044 g, 0.18 mmol) and oxalyl chloride (0.03 ml, 0.36 mmol) in dichloromethane was slowly added to the ice cooled solution of [1 -[3-chloro-5-(2,2-dibromovinyl)-2- pyridyl]cyclopropyl]methanamine (0.044 g, 0.12 mmol) and triethylamine (0.1 ml, 0.72 mmol) in 5 ml of dichloromethane. The mixture was stirred at r.t. overnight. The volatiles were evaporated and the residue was purified on silica gel, affording a resin (0.047 g, 73 %).
  • Step 1 tert-butyl N-rri -r3-chloro-5-(2,2-dichlorovinyl)-2- pyridyllcyclopropyllmethyllcarbamate
  • Step 2 [1 -[3-chloro-5-(2,2-dichlorovinyl)-2-pyridyllcvclopropyllmethanamine
  • Step 3 N-[[1 -[3-chloro-5-(2,2-dichlorovinyl)-2-pyridyllcvclopropyllmethyll-3- (trifluoromethyl)pyridine-2-carboxamide
  • Step 2 [1 -[3-chloro-5-[(E/Z)-2-chloro-3,3,3-trifluoro-prop-1 -enyll-2-pyridyllcvclopropyll methanamine
  • Step 3 ⁇ - ⁇ -r3-chloro-5-r(E/Z)-2-chloro-3,3,3-trifluoro-prop-1 -enyll-2-pyridyllcvclopropyll methyll-3-(trifluoromethyl)pyrazine-2-carboxamide (X.
  • Step 2 5-chloro-6-[1 -[[[3-(trifluoromethyl)pyridine-2-carbonyllaminolmethyllcvclopropyll pyridine-3-carboxylic acid
  • Step 3 N-[[1 -[3-chloro-5-(hvdroxymethyl)-2-pyridyllcvclopropyllmethyll-3-(trifluoromethyl) pyridine-2-carboxamide
  • Step 4 N-[[1 -(3-chloro-5-formyl-2-pyridyl)cvclopropyllmethyll-3-(trifluoromethyl)pyridine-2- carboxamide
  • Step 5 N-[[1 -[3-chloro-5-(2,2-difluorovinyl)-2-pyridyllcvclopropyllmethyll-3-(trifluoromethyl) pyridine-2-carboxamide (X.15)
  • N-[[1 -(3-chloro-5-formyl-2-pyridyl)cyclopropyl]methyl]-3-(trifluoromethyl)pyridine-2- carboxamide (0.1 g, 0.26 mmol) was dissolved in 2 ml of DMF and then sodium 2-chloro- 2,2-difluoro-acetate (0.072 g, 0.47 mmol) was added followed by triphenylphosphine (0.102 mg, 0.39 mmol). The mixture was stirred at 1 10°C for 35 min. The mixture was then cooled and diluted with 20 ml of toluene. The mixture was washed with water and the organic phase was dried and concentrated. The residue was purified on silica gel affording a resin (0.045 g, 41 %).
  • Step 1 N-rri-r3-chloro-5-r(E/Z)-2-chloro-3,3,3-trifluoro-prop-1 -enyll-2-pyridyllcvclopropyll methyll-3-(trifluoromethyl)pyridine-2-carboxamide (X.27)
  • N-[[1 -(3-chloro-5-formyl-2-pyridyl)cyclopropyl]methyl]-3-(trifluoromethyl)pyridine-2- carboxamide (96 mg, 0.25 mmol) was dissolved in dry DMF (1.5 mL) under argon, zinc powder (82 mg, 1 .25 mmol) and acetic anhydride (41 mg, 0.4 mmol) were then added followed by 1 ,1 ,1 -trichloro-2,2,2-trifluoro-ethane (94 mg, 0.5 mmol). The mixture was stirred under argon at 50°C for 5 h. The mixture was then cooled and treated with a saturated aqueous solution of NH 4 CI and extracted with ether. The organic phase was dried, concentrated and the residue was purified on silica gel to give a pale yellow resin which crystallized on standing.
  • Solvent degasser binary pump, heated column compartment and diode-array detector.
  • Biological examples Meloidogyne spp. (Root-knot nematode) contact activity, preventive. Pouch test.
  • 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 60% reduction of galling compared to the untreated control at 20 ppm: X.1 , X.2, X.3, X5, X6, X7, X8, X9, X10, X1 1 , X12, X13, X14

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

Abstract

L'invention concerne des composés de formule (I), dans laquelle les substituants sont tels que définis dans la revendication 1, lesquels composés sont appropriés pour une utilisation en tant que nématicides.
PCT/EP2014/058177 2013-04-26 2014-04-23 Carboxamides utilisés en tant que composés pesticides WO2014173921A1 (fr)

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Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2015125824A1 (fr) * 2014-02-18 2015-08-27 日産化学工業株式会社 Composé amide substitué par un groupe alkynylpyridine et agent de lutte contre des organismes nuisibles
WO2018003924A1 (fr) * 2016-06-29 2018-01-04 日産化学工業株式会社 Composé amide substitué par l'alkynylpyridine et agent de lutte antiparasitaire
CN109444290A (zh) * 2018-12-21 2019-03-08 广东方制药有限公司 车前草药材uplc特征图谱的构建方法和检测方法

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Publication number Priority date Publication date Assignee Title
WO2005058828A1 (fr) * 2003-12-19 2005-06-30 Bayer Cropscience S.A. Derives de 2-pyridinylethylbenzamide
EP1997800A1 (fr) * 2006-03-20 2008-12-03 Nihon Nohyaku Co., Ltd. Dérivé de n-2-(hétéro)aryléthylcarboxamide, et agent de maîtrise des nuisibles comprenant ledit dérivé
WO2013064460A1 (fr) * 2011-11-02 2013-05-10 Bayer Intellectual Property Gmbh Composés présentant une activité nématicide

Patent Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2005058828A1 (fr) * 2003-12-19 2005-06-30 Bayer Cropscience S.A. Derives de 2-pyridinylethylbenzamide
EP1997800A1 (fr) * 2006-03-20 2008-12-03 Nihon Nohyaku Co., Ltd. Dérivé de n-2-(hétéro)aryléthylcarboxamide, et agent de maîtrise des nuisibles comprenant ledit dérivé
WO2013064460A1 (fr) * 2011-11-02 2013-05-10 Bayer Intellectual Property Gmbh Composés présentant une activité nématicide

Cited By (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2015125824A1 (fr) * 2014-02-18 2015-08-27 日産化学工業株式会社 Composé amide substitué par un groupe alkynylpyridine et agent de lutte contre des organismes nuisibles
US10029986B2 (en) 2014-02-18 2018-07-24 Nissan Chemical Industries, Ltd. Alkynyl pyridine-substituted amide compound and pesticide
WO2018003924A1 (fr) * 2016-06-29 2018-01-04 日産化学工業株式会社 Composé amide substitué par l'alkynylpyridine et agent de lutte antiparasitaire
CN109444290A (zh) * 2018-12-21 2019-03-08 广东方制药有限公司 车前草药材uplc特征图谱的构建方法和检测方法
CN109444290B (zh) * 2018-12-21 2021-07-27 广东一方制药有限公司 车前草药材uplc特征图谱的构建方法和检测方法

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