WO2020244970A1 - Nouveaux carboxamides de pyridine carbocycliques - Google Patents

Nouveaux carboxamides de pyridine carbocycliques Download PDF

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WO2020244970A1
WO2020244970A1 PCT/EP2020/064579 EP2020064579W WO2020244970A1 WO 2020244970 A1 WO2020244970 A1 WO 2020244970A1 EP 2020064579 W EP2020064579 W EP 2020064579W WO 2020244970 A1 WO2020244970 A1 WO 2020244970A1
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alkyl
alkenyl
alkynyl
halogen
halogenalkyl
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PCT/EP2020/064579
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English (en)
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Georg Christoph RUDOLF
Michael Seet
Bernd Mueller
Wassilios Grammenos
Benjamin Juergen MERGET
Andreas Koch
Nadine RIEDIGER
Christine WIEBE
Thomas Grote
Jan Klaas Lohmann
Christian Winter
Anja Weber
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Basf Se
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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
    • 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
    • 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
    • C07D213/83—Thioacids; Thioesters; Thioamides; Thioimides

Definitions

  • the present invention relates to the use of pyridine compounds and the N-oxides and the salts thereof as fungicides as well to new pyridine compounds.
  • the invention also relates to the com- position comprising at least one compound I, to the method for combating phytopathogenic fungi and to the ssed coated with at least one compound of the formula I.
  • fungicidal activity of known compounds is unsatisfactory. Based on this, it was an objective of the present invention to provide com- pounds having improved activity and/or a broader activity spectrum against phytopathogenic fungi. Another object of the present invention is to provide fungicides with improved toxicological properties or with improved environmental fate properties.
  • the present invention relates to use of the compounds of formula I Use of the com- pounds of formula I
  • X is O or S
  • R 1 is in each case independently selected from hydrogen, halogen, CN, C 1 -C 6 -alkyl, C 1 -C 6 - halogenalkyl, C 2 -C 6 -alkenyl, C 2 -C 6 -halogenalkenyl, C 2 -C 6 -alkynyl, C 2 -C 6 -halogenalkynyl, O-C 1 -C 6 -alkyl, O-C 2 -C 6 -alkenyl, O-C 2 -C 6 -alkynyl, C 3 -C 6 -cycloalkyl, wherein the acyclic and cyclic moieties of R 1 are unsubstituted or substituted by one to six groups R 1a which independently of one another are selected from:
  • halogen CN, C 1 -C 6 -alkyl, C 1 -C 6 -halogenalkyl, C 2 -C 6 -alkenyl, C 2 -C 6 -halogenalkenyl, C 2 -C 6 - alkynyl, C 2 -C 6 -halogenalkynyl, O-C 1 -C 6 -alkyl, O-C 2 -C 6 -alkenyl, O-C 2 -C 6 -alkynyl;
  • R 2 is in each case independently selected from halogen, CN, C 1 -C 6 -alkyl, C 1 -C 6 -halogenalkyl, C 2 -C 6 -alkenyl, C 2 -C 6 -halogenalkenyl, C 2 -C 6 -alkynyl, C 2 -C 6 -halogenalkynyl, O-C 1 -C 6 -alkyl, O-C 2 -C 6 -alkenyl, O-C 2 -C 6 -alkynyl, C 3 -C 6 -cycloalkyl, wherein the acyclic and cyclic moieties of R 2 are unsubstituted or substituted by one to six groups R 2a which independently of one another are selected from:
  • halogen CN, C 1 -C 6 -alkyl, C 1 -C 6 -halogenalkyl, C 2 -C 6 -alkenyl, C 2 -C 6 -halogenalkenyl, C 2 -C 6 - alkynyl, C 2 -C 6 -halogenalkynyl, O-C 1 -C 6 -alkyl, O-C 2 -C 6 -alkenyl, O-C 2 -C 6 -alkynyl;
  • R 3 is in each case independently selected from halogen, CN, C 1 -C 6 -alkyl, C 1 -C 6 -halogenalkyl, C 2 -C 6 -alkenyl, C 2 -C 6 -halogenalkenyl, C 2 -C 6 -alkynyl, C 2 -C 6 -halogenalkynyl, O-C 1 -C 6 -alkyl, O-C 2 -C 6 -alkenyl, O-C 2 -C 6 -alkynyl, C 3 -C 6 -cycloalkyl, wherein the acyclic and cyclic moieties of R 3 are unsubstituted or substituted by one to six groups R 3a which independently of one another are selected from:
  • halogen CN, C 1 -C 6 -alkyl, C 1 -C 6 -halogenalkyl, C 2 -C 6 -alkenyl, C 2 -C 6 -halogenalkenyl, C 2 -C 6 - alkynyl, C 2 -C 6 -halogenalkynyl, O-C 1 -C 6 -alkyl, O-C 2 -C 6 -alkenyl, O-C 2 -C 6 -alkynyl;
  • R 4 is in each case independently selected from hydrogen, halogen, CN, C 1 -C 6 -alkyl, C 1 -C 6 - halogenalkyl, C 2 -C 6 -alkenyl, C 2 -C 6 -halogenalkenyl, C 2 -C 6 -alkynyl, C 2 -C 6 -halogenalkynyl, O-C 1 -C 6 -alkyl, O-C 2 -C 6 -alkenyl, O-C 2 -C 6 -alkynyl, C 3 -C 6 -cycloalkyl, wherein the acyclic and cyclic moieties of R 4 are unsubstituted or substituted by one to six groups R 4a which inde- pendently of one another are selected from:
  • halogen CN, C 1 -C 6 -alkyl, C 1 -C 6 -halogenalkyl, C 2 -C 6 -alkenyl, C 2 -C 6 -halogenalkenyl, C 2 -C 6 - alkynyl, C 2 -C 6 -halogenalkynyl, O-C 1 -C 6 -alkyl, O-C 2 -C 6 -alkenyl, O-C 2 -C 6 -alkynyl;
  • A is direct bond or C(R 7 R 8 );
  • halogen CN, C 1 -C 6 -alkyl, C 1 -C 6 -halogenalkyl, C 2 -C 6 -alkenyl, C 2 -C 6 -halogenalkenyl, C 2 -C 6 - alkynyl, C 2 -C 6 -halogenalkynyl, O-C 1 -C 6 -alkyl, O-C 2 -C 6 -alkenyl, O-C 2 -C 6 -alkynyl, C 3 -C 6 -cy- cloalkyl, O-C 3 -C 6 -cycloalkyl, CH 2 -C 3 -C 6 -cycloalkyl, C 3 -C 6 -cycloalkenyl, O-C 3 -C 6 -cycloal- kenyl, CH 2 -C 3 -C 6 -cycloalkenyl, CH 2 -C 3 -C 6 -cycloal
  • R ' is as defined above;
  • R 9 when A is C(R 7 R 8 ) R 9 can be also H;
  • R 5 , R 6 , R 7 or R 8 can not all be H; and the N-oxides and the agriculturally acceptable salts thereof as fungicides.
  • the N-oxides may be prepared from the inventive compounds according to conventional oxida- tion methods, e. g. by treating compounds I with an organic peracid such as metachloroper- benzoic acid (cf. WO 03/64572 or J. Med. Chem. 38(11), 1892-903, 1995); or with inorganic oxi- dizing agents such as hydrogen peroxide (cf. J. Heterocyc. Chem. 18(7), 1305-8, 1981) or ox- one (cf. J. Am. Chem. Soc. 123(25), 5962-5973, 2001).
  • the oxidation may lead to pure mono- N-oxides or to a mixture of different N-oxides, which can be separated by conventional methods such as chromatography.
  • Agriculturally acceptable salts of the compounds of the formula I encompass especially the salts of those cations or the acid addition salts of those acids whose cations and anions, respectively, have no adverse effect on the fungicidal action of the compounds I.
  • Suitable cations are thus in particular the ions of the alkali metals, preferably sodium and potassium, of the alkaline earth metals, preferably calcium, magnesium and barium, of the transition metals, preferably manga- nese, copper, zinc and iron, and also the ammonium ion which, if desired, may be substituted with one to four CrC 4 -alkyl substituents and/or one phenyl or benzyl substituent, preferably diisopropylammonium, tetramethylammonium, tetrabutylammonium, trimethylbenzylammonium, furthermore phosphonium ions, sulfonium ions, preferably tri(C 1 -C 4 -alkyl)sulf
  • Anions of acceptable acid addition salts are primarily chloride, bromide, fluoride, hydrogensul- fate, sulfate, dihydrogenphosphate, hydrogenphosphate, phosphate, nitrate, bicarbonate, car- bonate, hexafluorosilicate, hexafluorophosphate, benzoate, and the anions of C 1 -C 4 -alkanoic acids, preferably formate, acetate, propionate and butyrate. They can be formed by reacting a compound I with an acid of the corresponding anion, preferably of hydrochloric acid, hydrobro- mic acid, sulfuric acid, phosphoric acid or nitric acid.
  • Stereoisomers of the formula I can exist as one or more stereoisomers.
  • the various stereoisomers include enantiomers, diastereomers, atropisomers arising from restricted rotation about a single bond of asymmetric groups and geometric isomers. They also form part of the subject matter of the present invention.
  • one stereoisomer may be more active and/or may exhibit beneficial effects when enriched relative to the other stereoisomer(s) or when separated from the other stereoisomer(s). Additionally, the skilled artisan knows how to separate, enrich, and/or to selectively prepare said stereoisomers.
  • the compounds of the invention may be present as a mixture of stereoisomers, e.g. a racemate, individual
  • the embodiments of the intermediates obtained during preparation of compounds I correspond to the embodiments of the compounds of formula I.
  • the term“com- pounds I” refers to compounds of the formula I.
  • C n -C m indicates the number of carbon atoms possible in each case in the substituent or substituent moiety in question.
  • halogen refers to fluorine, chlorine, bromine and iodine.
  • C 1 -C 6 -alkyl refers to a straight-chained or branched saturated hydrocarbon group having 1 to 6 carbon atoms, e.g. methyl, ethyl, propyl, 1-methylethyl, butyl, 1-methylpropyl, 2- methylpropyl, 1 , 1 -di methylethyl , pentyl, 1-methylbutyl, 2-methylbutyl, 3-methylbutyl, 2,2-dime- thylpropyl, 1-ethylpropyl, 1 ,1 -dimethyl propyl, 1 ,2-dimethylpropyl, hexyl, 1-methylpentyl, 2- methylpentyl, 3-methylpentyl, 4-methylpentyl, 1 ,1-dimethylbutyl, 1 ,2-dimethylbutyl, 1 ,3-dimethyl- butyl, 2,2-dimethylbutyl, 2,3-dimethyl
  • C 2 -C 4 -alkyl refers to a straight-chained or branched alkyl group having 2 to 4 carbon atoms, such as ethyl, propyl (n-propyl), 1-methylethyl (iso-propoyl), butyl, 1 -methylpropyl (sec.- butyl), 2-methylpropyl (iso-butyl), 1 , 1 -dimethylethyl (tert.-butyl).
  • C 1 -C 6 -halogenalkyl refers to an alkyl group having 1 or 6 carbon atoms as defined above, wherein some or all of the hydrogen atoms in these groups may be replaced by halogen atoms as mentioned above.
  • Ci-C 2 -halogenalkyl such as chloromethyl, bromomethyl, dichloromethyl, trichloromethyl, fluoromethyl, difluoromethyl, trifluoromethyl, chlor- ofluoromethyl, dichlorofluoromethyl, chlorodifluoromethyl, 1-chloroethyl, 1-bromoethyl, 1-fluoro- ethyl, 2-fluoroethyl, 2,2-difluoroethyl, 2,2,2-trifluoroethyl, 2-chloro-2-fluoroethyl, 2-chloro-
  • C 1 -C 6 -alkoxy refers to a straight-chain or branched alkyl group having 1 to 6 carbon atoms which is bonded via an oxygen, at any position in the alkyl group.
  • Examples are “C 1 -C 4 - alkoxy” groups, such as methoxy, ethoxy, n-propoxy, 1-methylethoxy, butoxy, 1-methyhprop- oxy, 2-methylpropoxy or 1 ,1-dimethylethoxy.
  • C 1 -C 6 -halogenalkoxy refers to a C 1 -C 6 -alkoxy radical as defined above, wherein some or all of the hydrogen atoms in these groups may be replaced by halogen atoms as men- tioned above.
  • C 1 -C 4 -halogenalkoxy groups, such as OCH 2 F, OCHF 2 , OCF 3 , OCH 2 CI, OCHCI 2 , OCCI 3 , chlorofluoromethoxy, dichlorofluoromethoxy, chlorodifluoromethoxy, 2-fluoroethoxy, 2-chlorothoxy, 2-bromoethoxy, 2-iodoethoxy, 2,2-difluoroethoxy, 2,2,2-trifluoro- ethoxy, 2-chloro-2-fluoroethoxy, 2-chloro-2,2-difluoroethoxy, 2,2-dichloro-2-fluoroethoxy, 2,2,2- trichloroethoxy, OC 2 F5, 2-fluoropropoxy, 3-fluoropropoxy, 2,2-difluoropropoxy,
  • C 2 -C 6 -alkenyl refers to a straight-chain or branched unsaturated hydrocarbon radical having 2 to 6 carbon atoms and a double bond in any position.
  • Examples are “C 2 -C 4 -alkenyl” groups, such as ethenyl, 1-propenyl, 2-propenyl (allyl), 1-methylethenyl, 1-butenyl, 2-butenyl, 3-butenyl, 1 -methyl-1 -propenyl, 2-methyl-1-propenyl, 1-methyl-2-propenyl, 2-methyl-2-propenyl.
  • C 2 -C 6 -halogenalkenyl refers to an alkyl group having 2 or 6 carbon atoms as defined above, wherein some or all of the hydrogen atoms in these groups may be replaced by halogen atoms as mentioned above.
  • C 2 -C 6 -alkenyloxy refers to a straight-chain or branched alkenyl group having 2 to 6 carbon atoms which is bonded via an oxygen, at any position in the alkenyl group. Examples are “C 2 -C 4 -alkenyloxy” groups.
  • C 2 -C 6 -alkynyl refers to a straight-chain or branched unsaturated hydrocarbon radical having 2 to 6 carbon atoms and containing at least one triple bond.
  • C 2 -C 4 -al- kynyl examples are "C 2 -C 4 -al- kynyl” groups, such as ethynyl, prop-1-ynyl, prop-2-ynyl (propargyl), but-1-ynyl, but-2-ynyl, but- 3-ynyl, 1-methyl-prop-2-ynyl.
  • C 2 -C 6 -halogenalkynyl refers to an alkyl group having 2 or 6 carbon atoms as defined above, wherein some or all of the hydrogen atoms in these groups may be replaced by halogen atoms as mentioned above.
  • C 2 -C 6 -alkynyloxy refers to a straight-chain or branched alkynyl group having 2 to 6 carbon atoms which is bonded via an oxygen, at any position in the alkynyl group. Examples are “C 2 -C 4 -alkynyloxy” groups.
  • C 3 -C 6 -cycloalkyl refers to monocyclic saturated hydrocarbon radicals having 3 to 6 carbon ring members, such as cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl. Accordingly, a saturated three-, four-, five-, six-, seven-, eight-, nine or ten-membered carbocyclyl or carbo- cycle is a "C 3 -C 10 -cycloalkyl".
  • C 3 -C 6 -cycloalkenyl refers to a monocyclic partially unsaturated 3-, 4- 5- or 6-mem- bered carbocycle having 3 to 6 carbon ring members and at least one double bond, such as cy- clopentenyl, cyclopentadienyl, cyclohexadienyl. Accordingly, a partially unsaturated three-, four- , five-, six-, seven-, eight-, nine or ten-membered carbocyclyl or carbocycle is a "C 3 -C 10 -cycloal- kenyl".
  • C 3 -C 8 -cycloalkyl-C 1 -C 4 -alkyl refers to alkyl having 1 to 4 carbon atoms (as defined above), whereAccording to one hydrogen atom of the alkyl radical is replaced by a cycloalkyl radical having 3 to 8 carbon atoms (as defined above).
  • heterocyclyl or heterocycle contains 1 , 2, 3 or 4 heteroatoms selected from N, O and S
  • the ring member atoms of the heterocycle include besides carbon atoms 1 , 2, 3 or 4 heteroatoms independently selected from the group of O, N and S.
  • a 3- or 4-membered saturated heterocycle which contains 1 or 2 heteroatoms from the group consisting of O, N and S as ring members such as oxirane, aziridine, thiirane, oxetane, azet- idine, thiethane, [1 ,2]dioxetane, [1 ,2]dithietane, [1 ,2]diazetidine; and
  • a 5- or 6-membered saturated or partially unsaturated heterocycle which contains 1 , 2 or 3 het- eroatoms from the group consisting of O, N and S as ring members such as 2-tetrahydrofuranyl, 3-tetrahydrofuranyl, 2-tetrahydrothienyl, 3-tetrahydrothienyl, 2-pyrrolidinyl, 3-pyrrolidinyl, 3-isox- azolidinyl, 4-isoxazolidinyl, 5-isoxazolidinyl, 3-isothiazolidinyl, 4-isothiazolidinyl, 5-isothiazoli- dinyl, 3-pyrazolidinyl, 4-pyrazolidinyl, 5-pyrazolidinyl, 2-oxazolidinyl, 4-oxazolidinyl, 5-oxazoli- dinyl, 2-thiazolidinyl, 4-thiazolidinyl, 5-thiazolidinyl, 2-imidazolid
  • substituted refers to substitued with 1 , 2, 3 or up to the maximum possible number of substituents.
  • “5-or 6-membered heteroaryl” or“5-or 6-membered heteroaromatic” refers to aromatic ring systems incuding besides carbon atoms, 1 , 2, 3 or 4 heteroatoms independently selected from the group consisting of N, O and S, for example,
  • a 5-membered heteroaryl such as pyrrol-1 -yl, pyrrol-2-yl, pyrrol-3-yl, thien-2-yl, thien-3-yl, furan- 2-yl, furan-3-yl, pyrazol-1-yl, pyrazol-3-yl, pyrazol-4-yl, pyrazol-5-yl, imidazol-1-yl, imidazol-2-yl, imidazol-4-yl, imidazol-5-yl, oxazol-2-yl, oxazol-4-yl, oxazol-5-yl, isoxazol-3-yl, isoxazol-4-yl, isoxazol-5-yl, thiazol-2-yl, thiazol-4-yl, thiazol-5-yl, isothiazol-3-yl, isothiazol-4-yl, isothiazol-5-yl
  • a 6-membered heteroaryl such as pyridin-2-yl, pyridin-3-yl, pyridin-4-yl, pyridazin-3-yl, pyri- dazin-4-yl, pyrimidin-2-yl, pyrimidin-4-yl, pyrimidin-5-yl, pyrazin-2-yl and 1 ,3,5-triazin-2-yl and
  • R 1 is H, halogen, C 1 -C 6 -alkyl or C 1 -C 6 -halogenalkyl, in particular H, F, Cl, CH 3 , C 2 H5, CF 3 more specifically H, CH 3 , F or Cl most preferred H, F or Cl, especially R 1 is hydrogen.
  • R 1 Particularly preferred embodiments of R 1 according to the invention are in Table P1 below, wherein each line of lines P1-1 to P1-13 corresponds to one particular embodiment of the inven- tion. Thereby, for every R 1 that is present in the inventive compounds, these specific
  • R 2 is selected from the group consisting of C 1 -C 6 - alkyl, C 1 -C 6 -halogenalkyl, O-C 1 -C 6 -alkyl, C 3 -C 6 -cycloalkyl, in particular CH 3 , C 2 H 5 , CF 3 , CH 2 F, CHF 2 , OCH 3 , OC 2 H 5 , O-C 3 H 7 , O-C 4 H 9 , cyclopropyl, cyclobutyl, more specifically CH 3 , CH 2 F, CF 2 H, CF 3 , OCH3, OC 2 H5, most preferred OCH 3 , CH 3 .
  • R 2 is halogen, in particular F, Cl, Br or I, more specifically F, Cl or Br, in particular F or Cl.
  • R 2 is F.
  • R 2 is Cl
  • R 2 is Br
  • R 2 is CrC 6 -alkyl, in particular CrC 4 -alkyl, such as CH 3 . or C 2 H 5 , in particular CH 3 or CH 2 CH 3 .
  • R 2 is CrC 6 -halogenalkyl, in particular C 1 -C 4 - halogenalkyl, such as CF 3 , CCI 3 , FCH 2 , CICH 2 , F 2 CH, CI 2 CH, CF3CH2, CCI3CH2 or CF 2 CHF 2 .
  • R 2 is C 2 -C 6 -alkynyl or C 2 -C 6 -halogenalkynyl, in particular C 2 -C 4 -alkynyl or C 2 -C 4 -halogenalkynyl, such as CECH, CH 2 CECH, CECCI,
  • R 2 is O-C 1 -C 6 -alkyl, in particular C 1 -C 4 - alkyl, more specifically Ci-C 2 -alkoxy.
  • R 2 is such as OCH 3 or OCH 2 CH 3 .
  • R 2 is 0-CrC 6 -alkyl
  • R 2 is 0-C 2 -C 6 -alkenyl in particular C 2 - C 4 -alkenyl, more specifically C 2 -C 3 -alkenyl.
  • R 2 is 0-C 2 -C 6 -alkynyl, in particular C 2 - C 6 -alkynyl, in particular C 2 -C 4 -alkynyl, more specifically C 2 -C 3 -alkynyl.
  • R 2 is such as O-CH 2 - CECH.
  • R 2 is 0-CrC 6 -halogenalkyl, in particular OCF3, OCCb, OFCH2, OCICH2, OF2CH, OCI2CH, OCF3CH2, OCCI3CH2 or OCF2CHF2, more specifically OCF 3 , OF 2 CH, OFCH 2.
  • R 2 is C 3 -C 6 -cycloalkyl, in particular cyclopro- pyl or cyclobutyl.
  • R 2 is C 3 -C 6 -halogencycloalkyl.
  • R 2 is fully or partially halogenated cyclopropyl, such as 1-F-cyclopropyl, 1-CI- cyclopropyl, 2,2-F2-cyclopropyl, 2,2-Cl2-cyclopropyl .
  • Particularly preferred embodiments of R 2 according to the invention are in Table P2 below, wherein each line of lines P2-1 to P2-21 corresponds to one particular embodiment of the inven- tion, wherein P2-1 to P2-21 are also in any combination with one another a preferred embodi- ment of the present invention.
  • the connection point to the carbon atom, to which R 2 is bound is marked with“#” in the drawings.
  • R 3 is selected from the group consisting of C 1 -C 6 - alkyl, C 1 -C 6 -halogenalkyl, O-C 1 -C 6 -alkyl, C 3 -C 6 -cycloalkyl, in particular CH 3 , C 2 H 5 , CF 3 , CH 2 F, CHF 2 , OCH 3 , OC 2 H 5 , O-C 3 H 7 , O-C 4 H 9 , cyclopropyl, cyclobutyl, more specifically CH 3 , CH 2 F, CF 2 H, CF 3 , cyclopropyl, cyclobutyl, most preferred CH 3 , CF 2 H, CF 3 .
  • R 3 is halogen, in particular F, Cl, Br or I, more specifically F, Cl or Br, in particular F or Cl.
  • R 3 is F.
  • R 3 is Cl
  • R 3 is Br.
  • R 3 is C 1 -C 6 -alkyl, in particular CrC 4 -alkyl, such as CH 3 or C 2 H 5 , in particular CH 3 or CH 2 CH 3 .
  • R 3 is C 1 -C 6 -halogenalkyl, in particular C1 -C 4 - halogenalkyl, such as CF 3 , CCI 3 , FCH 2 , CICH 2 , F 2 CH, CI 2 CH, CF3CH2, CCI3CH2 or CF 2 CHF 2 .
  • R 3 is C 2 -C 6 -alkynyl or C 2 -C 6 -halogenalkynyl, in particular C 2 -C 4 -alkynyl or C 2 -C 4 -halogenalkynyl, such as CECH, CH 2 CECH, CECCI,
  • R 3 is O-C 1 -C 6 -alkyl, in particular C 1 -C 4 - alkyl, more specifically C 1 -C 2 -alkoxy.
  • R 3 is such as OCH3 or OCH2CH3.
  • R 3 is O-C 2 -C 6 -alkenyl in particular C 2 - C 4 -alkenyl, more specifically C 2 -C 3 -alkenyl.
  • R 3 is O-C 2 -C 6 -alkynyl, in particular C 2 - C 6 -alkynyl, in particular C 2 -C 4 -alkynyl, more specifically C 2 -C 3 -alkynyl.
  • R 3 is such as O-CH 2 - CECH.
  • R 3 is O-C 1 -C 6 -halogenalkyl, in particular OCFs, OCCb, OFCH2, OCICH2, OF2CH, OCI2CH, OCF3CH2, OCCI3CH2 or OCF2CHF2, more specifically OCF 3 , OF 2 CH, OFCH 2.
  • R 3 is C 3 -C 6 -cycloalkyl, in particular cyclopro- pyl, cyclobutyl.
  • R 3 is C 3 -C 6 -halogencycloalkyl.
  • R 3 is fully or partially halogenated cyclopropyl, such as 1-F-cyclopropyl, 1-CI- cyclopropyl, 2,2-F 2 -cyclopropyl, 2,2-Cl 2 -cyclopropyl .
  • R 3 Particularly preferred embodiments of R 3 according to the invention are in Table P3 below, wherein each line of lines P3-1 to P3-21 corresponds to one particular embodiment of the inven- tion, wherein P3-1 to P3-21 are also in any combination with one another a preferred embodi- ment of the present invention.
  • the connection point to the carbon atom, to which R 3 is bound is marked with“#” in the drawings.
  • R 4 is H, halogen, C 1 -C 6 -alkyl or C 1 -C 6 -halogenalkyl, in particular H, F, Cl, CH 3 , C 2 H5, CF 3 more specifically H, CH 3 , F or Cl most preferred H, F or Cl, especially R 4 is hydrogen.
  • R 4 Particularly preferred embodiments of R 4 according to the invention are in Table P4 below, wherein each line of lines P4-1 to P4-10 corresponds to one particular embodiment of the inven- tion. Thereby, for every R 4 that is present in the inventive compounds, these specific
  • ⁇ are in each case independently selected from hydrogen, halogen, CN, C 1 -C 6 -alkyl, C 1 -C 6 - halogenalkyl, C 2 -C 6 -alkenyl, C 2 -C 6 -halogenalkenyl, C 2 -C 6 -alkynyl, C 2 -C 6 -halogenalkynyl, O-CrC 6 -alkyl, O-C 2 -C 6 -alkenyl, O-C 2 -C 6 -alkynyl, C 3 -C 6 -cycloalkyl, O-C 3 -C 6 -cycloalkyl, CH2-C 3 -C 6 -cycloalkyl, C 3 -C 6 -cycloalkenyl, O-C 3 -C 6 -cycloalkenyl, CH2-C 3 -C 6 -cycloalkenyl, wherein the acyclic moieties of R 5
  • R 5 , R 6 , R 7 , R 8 are in each case independently se- lected from H, halogen, CN, C 1 -C 6 -alkyl, C 1 -C 6 -halogenalkyl, C 2 -C 6 -alkenyl, C 2 -C 6 -halogen- alkenyl, O-C 1 -C 6 -alkyl, C 3 -C 6 -cycloalkyl, O-C 3 -C 6 -cycloalkyl, CH2-C 3 -C 6 -cycloalkyl, C 3 -C 6 -cyclo- alkenyl, O-C 3 -C 6 -cycloalkenyl, CH2-C 3 -C 6 -cycloalkenyl
  • R 5 is preferably H, C 1 -C 6 -alkyl or C 1 -C 6 -alkyl-O-C 1 -C 6 -alkyl, more preferably H, CH3 , CH2OCH3.
  • R 6 is preferably C 1 -C 6 -alkyl, C 1 -C 4 - halogenalkyl, C 2 -C 4 -alkenyl, C 2 -C 4 -halogenalkenyl, cyclopropyl, CH 2 -cyclopropyl.
  • R 7 is preferably H or CrC 6 -alkyl, more preferably H and CH 3 .
  • R 8 is preferably H or CrC 6 -alkyl, more preferably H and CH 3 .
  • R 5 , R 6 , R 7 , R 8 are in each case independently H.
  • R 5 , R 6 , R 7 , R 8 are in each case inde- pendently halogen, preferably F or Cl, most preferably F.
  • R 5 , R 6 , R 7 , R 8 are in each case independently CN.
  • R 5 , R 6 , R 7 , R 8 are in each case inde- pendently CrC 6 -alkyl, such as CH 3 , C 2 H 5 , n-propyl, i-propyl, n-butyl, i-butyl, tert-butyl, n-pentyl, i-pentyl or CH 2 -C(CH 3 ) 3 .
  • R 5 , R 6 , R 7 , R 8 are in each case inde- pendently C 1 -C 6 -halogenalkyl, in particular CrC 4 -halogenalkyl, such as CF 3 , CCI 3 , FCH 2 , CICH 2 , F 2 CH, CI2CH, CF3CH2, CCI3CH2 or CF2CHF2.
  • R 5 , R 6 , R 7 , R 8 are in each case inde- pendently C 2 -C 6 -alkynyl or C 2 -C 6 -halogenalkynyl, in particular C 2 -C 4 -alkynyl or C 2 -C 4 -halogen- alkynyl, such as CoCH, CH 2 CECH, CECCI, CH 2 CECCI, or CCI 2 CoCCI.
  • R 5 , R 6 , R 7 , R 8 are in each case inde- pendently O-CrC 6 -alkanyl in particular C 2 -C 4 -alkanyl, more specifically Ci-C 2 -alkanyl.
  • R 5 , R 6 , R 7 , R 8 are in each case inde- pendently O-CrC 6 -alkanyl in particular C 2 -C 4 -alkanyl, more specifically Ci-C 2 -alkanyl.
  • R 7 , R 8 are in each case independently such as OCH 3 , OC 2 H 5 , O-n-propyl, O-iso-propyl, O-i- butyl, O-tert-butyl or O-CH 2 -C(CH3)3.
  • R 5 , R 6 , R 7 , R 8 are in each case inde- pendentlyC 3 -C 6 -cycloalkyl, O-C 3 -C 6 -cycloalkyl, CH2-C 3 -C 6 -cycloalkyl, C 3 -C 6 -cycloalkenyl, O-C 3 - C 6 -cycloalkenyl, CH2-C 3 -C 6 -cycloalkenyl, wherein the preferred C 3 -C 6 -cycloalkyl is selcteted from the group of jeweils cyclopropyl, 1-F-cyclopropyl, 1-CI-cyclopropyl, 2,2-F 2 -cyclopropyl, 2,2- CI 2 -cyclopropyl und cyclohexyl and wherein the preferred C 3 -C 6 -cycloalkenyl is selected from the group of cyclohexen-1-yl, cycl
  • R 5 , R 6 , R 7 , R 8 are in each case inde- pendently O-C 2 -C 6 -alkenyl in particular C 2 -C 4 -alkenyl, more specifically C 2 -C 3 -alkenyl.
  • R 5 , R 6 , R 7 , R 8 are in each case inde- pendently O-C 2 -C 6 -alkynyl, in particular C 2 -C 6 -alkynyl, in particular C 2 -C 4 -alkynyl, more specifically C 2 -C 3 -alkynyl.
  • R 5 , R 6 , R 7 , R 8 are in each case independently such as OCH 2 CoCH,
  • Particularly preferred embodiments of R 5 , R 6 , R 7 , R 8 according to the invention are in Table P5 below, wherein each line of lines P5-1 to P5-30 corresponds to one particular embodiment of the inven- tion, wherein P5-1 to P5-30 are also in any combination with one another a preferred embodi- ment of the present invention.
  • the connection point to the carbon atom, to which R 5 is bound is marked with“#” in the drawings.
  • R 9 is selected from the group consisting of CH 3 , CH2CH3, CH(CH 3 )2, CH(CH 3 )3, CF 3 , CF(CH 3 )2, CH 2 OCH(CH 3 )2, cyclopropyl, cyclobutyl, cyclo- pentyl, cyclohexyl, C 6 H 5 , 4-F-C 6 H 4 ; most preferred CH 3 and phenyl.
  • R 9 is C 1 -C 6 -alkyl, in particular CrC 4 -alkyl, such as CH 3 or C 2 H 5 , in particular CH 3 or CH 2 CH 3 .
  • R 9 is C 1 -C 6 -halogenalkyl, in particular C 1 -C 4 - halogenalkyl, such as CF 3 , CCI 3 , FCH 2 , CICH 2 , F 2 CH, CI 2 CH, CF 3 CH 2 , CCI 3 CH 2 or CF 2 CHF 2 .
  • R 9 is C 2 -C 6 -alkynyl or C 2 -C 6 -halogenalkynyl, in particular C 2 -C 4 -alkynyl or C 2 -C 4 -halogenalkynyl, such as CECH, CH 2 CoCH, CoCCI,
  • CH 2 CECCI, or CCI 2 CCI CCI 2 .
  • R 9 is C 3 -C 6 -cycloalkyl, in particular cyclopro- pyl, cyclohexyl.
  • R 9 is C 3 -C 6 -cycloalkenyl, in particular cyclo- pentenyl, or cyclohexenyl.
  • R 9 is phenyl, wherein phenyl in each case is unsubstituted or substituted by identical or different groups R 9a which independently of one an- other are selected from halogen, C 1 C 2 -alkyl, CN.
  • R 9 is a 5-membered heteroaryl such as pyr- rol-1-yl, pyrrol-2-yl, pyrrol-3-yl, thien-2-yl, thien-3-yl, furan-2-yl, furan-3-yl, pyrazol-1-yl, pyrazol- 3-yl, pyrazol-4-yl, pyrazol-5-yl, imidazol-1-yl, imidazol-2-yl, imidazol-4-yl, imidazol-5-yl, oxazol-2- yl, oxazol4-yl, oxazol-5-yl, isoxazol-3-yl, isoxazol-4-yl, isoxazol-5-yl, thiazol-2-yl, thiazol-4-yl, thi- azol-5-yl, isothiazol-3-yl, isothiazol-3-yl, iso
  • R 9 is a 6-membered heteroaryl such as pyri- din-2-yl, pyridin-3-yl, pyridin-4-yl, pyridazin-3-yl, pyridazin-4-yl, pyrimidin-2-yl, pyrimidin-4-yl, py- rimidin-5-yl, pyrazin-2-yl and 1 ,3,5-triazin-2-yl and 1 ,2,4-triazin-3-yl, preferred are pyridin-2-yl, pyridin-3-yl, pyridin-4-yl.
  • the 6-membered heteroaryl in each case is unsubstituted or substi- tuted by identical or different groups R 9a which independently of one another are selected from halogen, C 1 -C 2 -alkyl, CN.
  • R 9 Particularly preferred embodiments of R 9 according to the invention are in Table P9 below, wherein each line of lines P9-1 to P9-104 corresponds to one particular embodiment of the in- vention, wherein P5-1 to P5-104 are also in any combination with one another a preferred em- bodiment of the present invention.
  • the connection point to the carbon atom, to which R 9 is bound is marked with“#” in the drawings.
  • the invention relates to compounds of the formula I, or the N-oxides, or the agriculturally acceptable salts thereof, wherein
  • X is O; A is C(R 7 R 8 );
  • R 1 is H
  • R 2 is selected from the group consisting of C 1 -C 6 -alkyl, C 1 -C 6 -halogenalkyl or O-C 1 -C 6 -alkyl;
  • R 3 is selected from the group consisting of C 1 -C 6 -alkyl, C 1 -C 6 -halogenalkyl or C 3 -C 4 -cycloalkyl;
  • R 4 is H;
  • the invention relates to compounds of the formula I, or the N-oxides, or the agriculturally acceptable salts thereof, wherein
  • X is O; A is C(R 7 R 8 );
  • R 1 is H
  • R 2 is selected from the group consisting of CH 3 , C 2 H5, CF 3 , CH2F, CHF2, OCH 3 , OC 2 H5, O-C 3 H7, O-C 4 H 9 , cyclopropyl, cyclobutyl;
  • R 3 is selected from the group consisting of CH 3 , C 2 H5, CF 3 , CH2F, CHF2, cyclopropyl, cyclobutyl;
  • R 4 is H;
  • R 5 , R 6 , R 7 , R 8 are independently selected from H, halogen, CN, C 1 -C 6 -alkyl, C 1 -C 6 -halogenalkyl, C 3 -C 6 -cycloalkyl, O-C 1 -C 6 -alkyl, or two moieties:
  • the invention relates to compounds of the formula I, or the N-oxides, or the agriculturally acceptable salts thereof, wherein
  • X is O
  • A is C(R 7 R 8 );
  • R 1 is H
  • R 2 is selected from the group consisting of CH 3 , OCH 3 ;
  • R 3 is selected from the group consisting of CH 3 , CF 3 , CF2H;
  • R 4 is H
  • R 5 is selected from the group consisting of H, CH 3, CN, CH2OCH 3 .
  • R 6 is selected from the group consisting of C 1 -C 6 -alkyl, CrC 4 -halogenalkyl, C 2 -C 4 -alkenyl, C 2 -C 4 - halogenalkenyl, cyclopropyl, CH 2 -cyclopropyl,
  • R 7 is selected from the group consisting of H and CH 3 ;
  • R 8 is selected from the group consisting of H and CH 3 .
  • R 9 is selected from the group consisting of CH 3 , phenyl, pyridine-2-yl, pyridine-3-yl, pyridine-4-yl and cyclohexyl.
  • the invention relates to compounds of the formula I, or the N-oxides, or the agriculturally acceptable salts thereof, wherein
  • X is O
  • A is a direct bond
  • R 1 is H
  • R 2 is selected from the group consisting of CH 3 , OCH 3 ;
  • R 3 is selected from the group consisting of CH 3 , CF 3 , CF2H;
  • R 4 is H
  • R 5 is selected from the group consisting of H, CH 3, CN, CH2OCH 3 .
  • R 6 is selected from the group consisting of C 1 -C 6 -alkyl, C 1 C 4 -halogenalkyl, C 2 -C 4 -alkenyl, C 2 -C 4 - halogenalkenyl, cyclopropyl, CH 2 -cyclopropyl,
  • R 7 is selected from the group consisting of H and CH 3 ;
  • R 8 is selected from the group consisting of H and CH 3 .
  • R 9 is selected from the group consisting of CH 3 , phenyl, pyridine-2-yl, pyridine-3-yl, pyridine-4-yl and cyclohexyl.
  • the invention relates to compounds of the formula I, or the N-oxides, or the agriculturally acceptable salts thereof, wherein
  • X is O
  • A is a direct bond
  • R 1 is H
  • R 2 is selected from the group consisting of CH 3 , C 2 H5, CF 3 , CH2F, CHF2, OCH 3 , OC 2 H5, O-C 3 H7, O-C 4 H 9 , cyclopropyl, cyclobutyl;
  • R 3 is selected from the group consisting of CH 3 , C 2 H5, CF 3 , CH2F, CHF2, cyclopropyl, cyclobutyl;
  • R 4 is H;
  • R 5 , R 6 are independently selected from H, halogen, CN, C 1 -C 6 -alkyl, C 1 -C 6 -halogenalkyl, O-C 1 - C 6 -alkyl, or two moieties:
  • the invention relates to compounds of the formula I, or the N-oxides, or the agriculturally acceptable salts thereof, wherein
  • X is O
  • A is a direct bond
  • R 1 is H
  • R 2 is selected from the group consisting of CH 3 , OCH 3 ;
  • R 3 is selected from the group consisting of CH 3 , CF 3 , CF 2 H;
  • R 4 is H
  • R 5 is selected from the group consisting of H, CH 3, CH2OCH 3 .
  • R 6 is selected from the group consisting of C 1 -C 6 -alkyl, CrC 4 -halogenalkyl, C 2 -C 4 -alkenyl,
  • R 9 is selected from the group consisting of CH 3 and cyclopropyl.
  • Preferred embodiments of the present invention are the following compounds I.A-1 , I.A-2, I.A-3, I.A-4, I.A-5, I.A-6, I.A-6; compounds I.B-1 , I.B-2, I.B-3, I.B-4, I.B-5, I.B-6.
  • the substituents R 5 , R 6 , R 7 , R 8 and R 9 are independently as defined above or preferably defined herein:
  • Table 1a Compounds of the formula I.A-1, I.A-2, I.A-3, I.A-4, I.A-5, I.A-6; I.B-1, I.B-2, I.B-3, I.B-
  • Table 2a Compounds of the formula I.A-1, I.A-2, I.A-3, I.A-4, I.A-5, I.A-6; I.B-1, I.B-2, I.B-3, I.B- 4, I.B-5, I.B-6 in which A is -CHF- and the meaning for the combination of R 5 , R 6 and R 9 for each individual compound corresponds in each case to one line of Table B (compounds I.A-1.2a.B-1 to I.A-1.2a.B-396, I.A-2.2a.B-1 to I.A-2.2a.B-396, I .A-3.2a.B-1 to I.A-3.2a.B-396, I .A-4.2a.B-1 to I.A-5.2a.B-396, I.A-5.2a.B-1 to I.A-3.2a.B-396, I.A-6.2a.B-1 to I .A-6.2a.B-396; B-1.2a.B-1 to I.B-
  • Table 3a Compounds of the formula I. A-1 , I.A-2, I.A-3, I.A-4, I.A-5, I.A-6; I.B-1 , I.B-2, I.B-3, I.B- 4, I.B-5, I.B-6 in which A is -CH(CH3)- and the meaning for the combination of R 5 , R 6 and R 9 for each individual compound corresponds in each case to one line of Table B (compounds I.A- 1.3a.B-1 to I.A-1.3a.B-396, I.A-2.3a.B-1 to I.A-2.3a.B-396, I.A-3.3a.B-1 to I.A-3.3a.B-396, I.A- 4.3a.B-1 to I.A-5.3a.
  • B-396 I.A-5.3a.B-1 to I.A-3.3a.B-396, I.A-6.3a.B-1 to I.A-6.3a.B-396;
  • Table 4a Compounds of the formula I. A-1 , I.A-2, I.A-3, I.A-4, I.A-5, I.A-6; I.B-1 , I.B-2, I.B-3, I.B- 4, I.B-5, I.B-6 in which A is -CF(CH3)- and the meaning for the combination of R 5 , R 6 and R 9 for each individual compound corresponds in each case to one line of Table B (compounds I.A- 1.4a.B-1 to I .A-1.4a.
  • B-396 I.A-2.4a.B-1 to I.A-2.4a.B-396, I.A-3.4a.B-1 to I.A-3.4a.B-396, I.A- 4.4a.B-1 to I.A-5.4a.
  • B-396 I.A-5.4a.B-1 to I.A-3.4a.B-396, I.A-6.4a.B-1 to I.A-6.4a.B-396; B- 1.4a.B-1 to I.B-1.4a.
  • Table 5a Compounds of the formula I. A-1 , I.A-2, I.A-3, I.A-4, I.A-5, I.A-6; I.B-1 , I.B-2, I.B-3, I.B- 4, I.B-5, I.B-6 in which A is -CF2- and the meaning for the combination of R 5 , R 6 and R 9 for each individual compound corresponds in each case to one line of Table B (compounds I.A-1.5a.B-1 to I. A-1.5a.
  • B-396 I.A-2.5a.B-1 to I.A-2.5a.B-396, I .A-3.5a.B-1 to I.A-3.5a.B-396, I .A-4.5a.B-1 to I.A-5.5a. B-396, I.A-5.5a.B-1 to I.A-3.5a.B-396, I.A-6.5a.B-1 to I .A-6.5a.B-396; B-1.5a.B-1 to I.B- 1.5a. B-396, I.B-2.5a.B-1 to I.B-2.5a.B-396, I.B-3.5a.B-1 to I.B-3.5a.B-396, I.B-4.5a.B-1 to I.B- 4.5a. B-396, I.B-5.5a.B-1 to I.B-5.5a.B-396, I.B-6.5a.B-1 to I.B-6.5a. B-396).
  • Table 6a Compounds of the formula I. A-1 , I.A-2, I.A-3, I.A-4, I.A-5, I.A-6; I.B-1 , I.B-2, I.B-3, I.B- 4, I .B-5, I.B-6 in which A is -C(CH3)2- and the meaning for the combination of R 5 , R 6 and R 9 for each individual compound corresponds in each case to one line of Table B (compounds I.A- 1.6a.B-1 to I .A-1.6a.
  • B-396 I.A-2.6a.B-1 to I.A-2.6a.B-396, I.A-3.6a.B-1 to I.A-3.6a.B-396, I.A- 4.6a.B-1 to I.A-5.6a. B-396, I.A-5.6a.B-1 to I.A-3.6a.B-396, I.A-6.6a.B-1 to I.A-6.6a.B-396; B- 1.6a.B-1 to I.B-1.6a.
  • Table 7a Compounds of the formula I. A-1 , I.A-2, I.A-3, I.A-4, I.A-5, I.A-6; I.B-1 , I.B-2, I.B-3, I.B- 4, I.B-5, I.B-6 in which A is direct bound and the meaning for the combination of R 5 , R 6 and R 9 for each individual compound corresponds in each case to one line of Table B (compounds I.A- 1.7a.B-1 to I. A-1.7a. B-396, I.A-2.7a.B-1 to I.A-2.7a.B-396, I.A-3.7a.B-1 to I.A-3.7a.B-396, I.A- 4.7a.
  • organometallic compounds of formula (IVa) can be prepared from 3-halopyridines of type IV (R 1 -R 4 are as defined for compounds of formula I) by lithium-halogen exchange with an alkyl lithium reagent like s-butyl lithium, direct zinc in- sertion or magnesium-halogen exchange with tri n-butyl magnesate as described in syn- thetic chemistry texts such as March's Advanced Organic Chemistry.
  • Amines of formula (III) can be prepared from carboxylic acid derivatives of formula (Va) or (Vb) through an intermediate isocyanate of formula (Ilia) or a carbamate of formula (lllb) (where L is C 1 -C 4 alkyl), which can be hydrolyzed with aqueous acid or base at tempera- tures between 0 °C and 100 °C as shown in scheme 4.
  • propylphosphonic anhydride in the presence of an azide source like sodium azide and an amine base like triethyl amine in an inert solvent like THF at temperatures between 20 °C and 100 °C, followed by thermal rearrangement in an inert solvent such as toluene as de- scribed in Synthesis 2011 , 1477-1483.
  • primary carboxamide (Vb) can be treated with an oxidizing agent such as bromine and a base such as sodium hydroxide in a solvent like water or methanol at temperatures be- tween 0 °C and 100 °C.
  • an oxidizing agent such as bromine
  • a base such as sodium hydroxide
  • carboxylic acids of formula (Va) and amide (Vb) can be prepared from the corresponding esters.
  • the al pha functionalization of these esters can be done by deprotonation with a strong base like lithium diisopropylamide in an inert solvent like THF at temperatures between -78 °C and 20 °C followed by reaction with an electrophilic reagent such as an alkyl halide as de- scribed in March's Advanced Organic Chemistry, Smith and March, 6 ⁇ edition, Wiley,
  • Amines of formula (III) wherein A is a direct bond are commercially available or can be prepared in multistep sequences using transformation that belongs to the knowledge of a person skilled in the art. Examples of amine preparation can be found in EP943602 or in J. Org. Chem. 2014, 79, 1254-1264.
  • amines of formula (III) wherein A is a direct bond can be prepared by the condensation reaction between carbonyl com- pounds of formula ( 111 c) with a sulfinamide (I lie) (where Z is C 2 -C 5 alkyl or phenyl and the phenyl group can be substituted with 1 to 3 groups independently selected from C 1 -C 4 alkyl and nitro) in the presence of a dehydrating agent like Ti(OEt)4 to form sulfimines of formula (lllf), which then reacts with an organometallic reagent of formula (lllg) (where Y is lithium, a copper, an aluminum- or a magnesium-salt) in an inert organic solvent like THF at tempera- tures between -78 °C and + 70 °C, followed by an acidic hydrolysis of the sulfinamide.
  • the reaction was described in Chem. Rev. 2010, 3600-3740.
  • Amines of formula (llli) where A is -CH2- can be also prepared by the sequences shown in scheme 6:
  • Aziridine of formula (VI) can also be accessed by aziridination of olefins of formula (Vic) with sulfonamides in the presence of an oxidizing agent and a rhodium catalyst as de- scribed in Org. Lett., 2005, 2787-2790. Ring opening of the aziridine with (lllg) and removal of the sulfonyl group afforded Amines of formula (llli) as described in the section above.
  • the compounds of the formula II and IV are commercially available.
  • the N-oxides may be prepared from the inventive compounds according to conventional oxi- dation methods as described in WO 03/64572 or J. Med. Chem. 1995,1892-903 or J. Hetero- cycl. Chem. 1981 ,1305-8 or. J. Am. Chem. Soc. 2001 , 5962-5973.
  • the oxidation may lead to pure mono-N-oxides or to a mixture of different N-oxides, which can be separated by conven- tional methods such as chromatography.
  • the compounds I and the compositions according to the invention are particularly important in the control of a multitude of phytopathogenic fungi on various cultivated plants, such as cereals, e. g. wheat, rye, barley, triticale, oats or rice; beet, e. g. sugar beet or fodder beet; fruits, such as pomes, stone fruits or soft fruits, e. g.
  • compounds I and compositions thereof are used for controlling a mul- titude of fungi on field crops, such as potatoes sugar beets, tobacco, wheat, rye, barley, oats, rice, corn, cotton, soybeans, rape, legumes, sunflowers, coffee or sugar cane; fruits; vines; or- namentals; or vegetables, such as cucumbers, tomatoes, beans or squashes.
  • field crops such as potatoes sugar beets, tobacco, wheat, rye, barley, oats, rice, corn, cotton, soybeans, rape, legumes, sunflowers, coffee or sugar cane; fruits; vines; or- namentals; or vegetables, such as cucumbers, tomatoes, beans or squashes.
  • plant propagation material is to be understood to denote all the generative parts of the plant such as seeds and vegetative plant material such as cuttings and tubers (e. g. pota- toes), which can be used for the multiplication of the plant.
  • vegetative plant material such as cuttings and tubers (e. g. pota- toes)
  • These young plants may also be protected before transplantation by a total or partial treatment by im- mersion or pouring.
  • treatment of plant propagation materials with compounds I and compositions thereof, respectively is used for controlling a multitude of fungi on cereals, such as wheat, rye, barley and oats; rice, corn, cotton and soybeans.
  • cultiva plants is to be understood as including plants which have been modified by mutagenesis or genetic engineering in order to provide a new trait to a plant or to modify an already present trait.
  • Mutagenesis includes techniques of random mutagenesis using X-rays or mutagenic chemi- cals, but also techniques of targeted mutagenesis, to create mutations at a specific locus of a plant genome.
  • Targeted mutagenesis techniques frequently use oligonucleotides or proteins like CRISPR/Cas, zinc-finger nucleases, TALENs or meganucleases to achieve the targeting effect.
  • Genetic engineering usually uses recombinant DNA techniques to create modifications in a plant genome which under natural circumstances cannot readily be obtained by cross breeding, mutagenesis or natural recombination.
  • one or more genes are integrated into the ge- nome of a plant to add a trait or improve a trait.
  • transgenic plants These integrated genes are also referred to as transgenes in the art, while plant comprising such transgenes are referred to as transgenic plants.
  • the process of plant transformation usually produces several transformation events, wich differ in the genomic locus in which a transgene has been integrated. Plants comprising a specific transgene on a specific genomic locus are usually described as comprising a specific “event”, which is referred to by a specific event name. Traits which have been introduced in plants or have been modified include herbicide tolerance, insect resistance, increased yield and tolerance to abiotic conditions, like drought.
  • Herbicide tolerance has been created by using mutagenesis as well as using genetic engi- neering. Plants which have been rendered tolerant to acetolactate synthase (ALS) inhibitor herbicides by mutagenesis and breeding comprise plant varieties commercially available under the name Clearfield®.
  • ALS acetolactate synthase
  • Herbicide tolerance has been created via the use of transgenes to glyphosate, glufosinate, 2,4-D, dicamba, oxynil herbicides, like bromoxynil and ioxynil, sulfonylurea herbicides, ALS in- hibitors and 4-hydroxyphenylpyruvate dioxygenase (HPPD) inhibitors, like isoxaflutole and mes- otrione.
  • transgenes to glyphosate, glufosinate, 2,4-D, dicamba, oxynil herbicides, like bromoxynil and ioxynil, sulfonylurea herbicides, ALS in- hibitors and 4-hydroxyphenylpyruvate dioxygenase (HPPD) inhibitors, like isoxaflutole and mes- otrione.
  • HPPD 4-hydroxyphenylpyruvate dioxygenase
  • Transgenes wich have been used to provide herbicide tolerance traits comprise: for tolerance to glyphosate: cp4 epsps, epsps grg23ace5, mepsps, 2mepsps, gat4601 , gat4621 , goxv247; for tolerance to glufosinate: pat and bar, for tolerance to 2,4-D: aad-1 , aad-12; for tolerance to dicamba: dmo; for tolerance to oxynil herbicies: bxn; for tolerance to sulfonylurea herbicides: zm-hra, csr1-2, gm-hra, S4-HrA; for tolerance to ALS inhibitors: csr1-2; and for tolerance to HPPD inhibitors: hppdPF, W336, avhppd-03.
  • Transgenic corn events comprising herbicide tolerance genes include, but are not limited to, DAS40278, MON801 , MON802, MON809, MON810, MON832, MON87411 , MON87419, MON87427, MON88017, MON89034, NK603, GA21 , MZHG0JG, HCEM485, VCO-01981-5, 676, 678, 680, 33121 , 4114, 59122, 98140, Bt10, Bt176, CBH-351 , DBT418, DLL25, MS3,
  • Transgenic soybean events comprising herbicide tolerance genes include, but are not limited to, GTS 40-3-2, MON87705, MON87708, MON87712, MON87769, MON89788, A2704-12, A2704-21 , A5547-127, A5547-35, DP356043, DAS44406-6, DAS68416-4, DAS-81419-2, GU262, SYHT0H2, W62, W98, FG72 and CV127.
  • Transgenic cotton events comprising herbicide tolerance genes include, but are not limited to, 19-51 a, 31707, 42317, 81910, 281-24-236, 3006-210-23, BXN10211 , BXN10215, BXN10222, BXN 10224, MON1445, MON1698, MON88701 , MON88913, GHB119, GHB614, LLCotton25, T303-3 and T304-40.
  • Transgenic canola events comprising herbicide tolerance genes are for example, but not ex- cluding others, MON88302, HCR-1 , HCN10, HCN28, HCN92, MS1 , MS8, PHY14, PHY23, PHY35, PHY36, RF1 , RF2 and RF3.
  • Transgenes which have most frequently been used are toxin genes of Bacillus spp. and synthetic variants thereof, like cry1A, crylAb, cry1Ab-Ac, crylAc, cry1A.105, cry1 F, cry1 Fa2, cry2Ab2, cry2Ae, mcry3A, ecry3.1Ab, cry3Bb1 , cry34Ab1 , cry35Ab1 , cry9C, vip3A(a), vip3Aa20.
  • genes of plant origin such as genes coding for protease inhibitors, like CpTI and pinll, have been transferred to other plants.
  • a further approach uses transgenes such as dvsnf7 to produce double-stranded RNA in plants.
  • Transgenic corn events comprising genes for insecticidal proteins or double stranded RNA in- clude, but are not limited to, Bt10, Bt11 , Bt176, MON801 , MON802, MON809, MON810, MON863, MON87411 , MON88017, MON89034, 33121 , 4114, 5307, 59122, TC1507, TC 6 275, CBH-351 , MIR162, DBT418 and MZIR098.
  • Transgenic soybean events comprising genes for insecticidal proteins include, but are not limited to, MON87701 , MON87751 and DAS-81419.
  • Transgenic cotton events comprising genes for insecticidal proteins include, but are not limited to, SGK321 , MON531 , MON757, MON1076, MON15985, 31707, 31803, 31807, 31808, 42317, BN LA-601 , Eventl , COT67B, COT102, T303-3, T304-40, GFM Cry1A, GK12, MLS 9124, 281- 24-236, 3006-210-23, GHB119 and SGK321.
  • transgene athb17 being present for example in corn event MON87403, or by using the transgene bbx32, being present for example in the soy- bean event MON87712.
  • transgenes gm-fad2-1 , Pj.D6D, Nc.Fad3, fad2-1A and fatb1-A. Soybean events comprising at least one of these genes are: 260-05, MON87705 and MON87769.
  • transgene cspB comprised by the corn event MON87460 and by using the transgene Hahb-4, comprised by soybean event IND-00410-5.
  • Preferred combinations of traits are combinations of herbicide tolerance traits to different groups of herbicides, combinations of insect tolerance to different kind of insects, in particular tolerance to lepidopteran and coleopteran insects, combinations of herbicide tolerance with one or several types of insect resistance, combinations of herbicide tolerance with increased yield as well as combinations of herbicide tolerance and tolerance to abiotic conditions.
  • Plants comprising singular or stacked traits as well as the genes and events providing these traits are well known in the art.
  • detailed information as to the mutagenized or inte- grated genes and the respective events are available from websites of the organizations“Inter- national Service for the Acquisition of Agri-biotech Applications (ISAAA)”
  • effects which are specific to a cultivated plant comprising a certain gene or event may result in effects which are specific to a cultivated plant comprising a certain gene or event. These effects might involve changes in growth behavior or changed resistance to biotic or abiotic stress factors. Such effects may in particular comprise enhanced yield, en- hanced resistance or tolerance to insects, nematodes, fungal, bacterial, mycoplasma, viral or viroid pathogens as well as early vigour, early or delayed ripening, cold or heat tolerance as well as changed amino acid or fatty acid spectrum or content.
  • the compounds I and compositions thereof, respectively, are particularly suitable for control- ling the following plant diseases:
  • Albugo spp. white rust on ornamentals, vegetables (e. g. A. Candida ) and sunflowers (e. g. A. tragopogonis ); Alternaria spp. (Alternaria leaf spot) on vegetables (e.g. A. dauci or A. porn), oilseed rape (A. brassicicola or brassicae), sugar beets (A. tenuis), fruits (e.g. A. grandis), rice, soybeans, potatoes and tomatoes (e. g. A. solani, A. grandis or A. alternata), tomatoes (e. g. A. solani or A. alternata) and wheat (e.g. A. triticina) ⁇ , Aphanomyces spp.
  • Ascochyta spp. on cereals and vegetables, e. g. A. tritici (anthracnose) on wheat and A. hordei on barley; Aureobasidium zeae (syn. Kapatiella zeae) on corn; Bipolaris and Drechslera spp. (teleomorph: Cochliobolus spp.), e. g. Southern leaf blight (D. maydis) or Northern leaf blight ( B . zeicola) on corn, e. g. spot blotch ( B . sorokiniana) on cereals and e. g. B.
  • Botrytis cinerea teleomorph: Botryotinia fuckeliana grey mold
  • fruits and berries e. g. strawberries
  • vegetables e. g. lettuce, carrots, celery and cabbages
  • B. squa mosa or B. allii on onion family oilseed rape, ornamentals (e.g. B eliptica), vines, forestry plants and wheat
  • Bremia lactucae downy mildew
  • Ceratocystis syn. Ophiostoma
  • lirio- dendri teleomorph: Neonectria liriodendrr. Black Foot Disease) and ornamentals; Dematophora (teleomorph: Rosellinia) necatrix (root and stem rot) on soybeans; Diaporthe spp., e. g. D.
  • phaseolorum (damping off) on soybeans; Drechslera (syn. Helminthosporium, teleomorph: Pyr- enophora) spp. on corn, cereals, such as barley (e. g. D. teres, net blotch) and wheat (e. g. D. tritici-repentis ⁇ . tan spot), rice and turf; Esca (dieback, apoplexy) on vines, caused by Formiti- poria (syn. Phellinus) punctata, F.
  • Phaeomoniella chlamydospora (formerly Phae- oacremonium chlamydosporum ), Phaeoacremonium aleophilum and/or Botryosphaeria obtusa ⁇ Elsinoe spp. on pome fruits (E. pyri), soft fruits (E. veneta : anthracnose) and vines (E. ampelina : anthracnose); Entyloma oryzae (leaf smut) on rice; Epicoccum spp. (black mold) on wheat; Ery- siphe spp. (powdery mildew) on sugar beets (E. betae), vegetables (e.
  • E. pisi such as cu- curbits (e. g. E. cichoracearum), cabbages, oilseed rape (e. g. E. cruciferarum) ⁇ , Eutypa lata (Eu- typa canker or dieback, anamorph: Cytosporina lata, syn. Libertella blepharis ) on fruit trees, vines and ornamental woods; Exserohilum (syn. Helminthosporium) spp. on corn (e. g. E. turci- cum) ⁇ Fusarium (teleomorph: Gibberella) spp. (wilt, root or stem rot) on various plants, such as E. graminearum or E.
  • cu- curbits e. g. E. cichoracearum
  • cabbages oilseed rape
  • oilseed rape e. g. E. cruciferarum
  • Eutypa lata Eu- typa canker or dieback
  • Bakanae disease Glomerella cingulata on vines, pome fruits and other plants and G. gossypii on cotton; Grain- staining complex on rice; Guignardia bidwellii (black rot) on vines; Gymnosporangium spp. on rosaceous plants and junipers, e. g. G. sabinae (rust) on pears; Helminthosporium spp. (syn. Drechslera, teleomorph: Cochliobolus) on corn, cereals, potatoes and rice; Hemileia spp., e. g. H.
  • Monilia spp. bloom and twig blight, brown rot) on stone fruits and other rosaceous plants; Mycosphaerella spp. on cereals, bananas, soft fruits and ground nuts, such as e. g. M. graminicola (anamorph: Zymoseptoria tritici formerly Septoria triticr. Septoria blotch) on wheat or M. fijiensis (syn. Pseudocercospora fijiensis ⁇ . black Sigatoka disease) and M. musicola on bana- nas, M. arachidicola (syn. M. arachidis or Cercospora arachidis), M. berkeleyi on peanuts, M.
  • M. graminicola anamorph: Zymoseptoria tritici formerly Septoria triticr. Septoria blotch
  • M. fijiensis syn. Pseudocercospora fijiensis ⁇
  • gregata stem rot
  • Phoma lingam (syn. Leptosphaeria biglobosa and L maculans. root and stem rot) on oilseed rape and cabbage
  • P. betae root rot, leaf spot and damping-off) on sugar beets
  • P. zeae-maydis (syn. Phyllostica zeae) on corn
  • Phomopsis spp. on sunflowers, vines e. g. P. viticoia ⁇ can and leaf spot
  • soybeans e. g. stem rot: P.
  • phaseoli, teleomorph Diaporthe phaseolorum
  • Physoderma maydis brown spots
  • Phytophthora spp. wilt, root, leaf, fruit and stem root
  • various plants such as paprika and cucurbits (e. g. P. capsici), soybeans (e. g. P. megasperma, syn. P. sojae), potatoes and toma- toes (e. g. P. infestans. late blight) and broad-leaved trees (e. g. P. ramorurrr.
  • Plasmodiophora brassicae club root
  • Plasmopara spp. e. g. P. viticola (grapevine downy mildew) on vines and P. halstedii on sun- flowers
  • Podosphaera spp. powdery mildew
  • Polymyxa spp. e. g. on cereals, such as barley and wheat (P. graminis) and sugar beets (P.
  • Puc- cinia spp. rusts on various plants, e. g. P. triticina (brown or leaf rust), P. striiformis (stripe or yellow rust), P. hordei (dwarf rust), P. graminis (stem or black rust) or P. recondita (brown or leaf rust) on cereals, such as e. g. wheat, barley or rye, P.
  • kuehnii orange rust
  • Pyrenopeziza spp. e.g. P. brassicae on oilseed rape
  • Pyrenophora anamorph: Drechslera
  • tritici-repentis tan spot
  • P. teres net blotch
  • Pyricularia spp. e. g. P. oryzae (teleomorph: Magnaporthe grisea ⁇ rice blast) on rice and P. grisea on turf and cereals
  • R. solani root and stem rot
  • S. solani silk and stem rot
  • S. solani silk and stem rot
  • S. solani silk blight
  • R. cerealis Rhizoctonia spring blight
  • Rhizopus stolonifer black mold, soft rot
  • Rhynchosporium secalis and R. commune scald
  • Stagonospora nodorum (Stagonospora blotch) on cere- als; Uncinula (syn. Erysiphe) necator ( powdery mildew, anamorph: Oidium tuckeri) on vines; Se- tosphaeria spp. (leaf blight) on corn (e. g. S. turcicum, syn. Helminthosporium turcicum) and turf; Sphacelotheca spp. (smut) on corn, (e. g. S. reiliana, syn. Ustilago reiliana ⁇ . head smut), sorghum und sugar cane; Sphaerotheca fuliginea (syn.
  • Podosphaera xanthir. powdery mildew on cucurbits
  • Spongospora subterranea pausing potato diseases
  • Stagonospora spp. on cereals, e. g. S. nodorum (Stagonospora blotch, teleo- morph: Leptosphaeria [syn. Phaeosphaeria] nodorum, syn. Septoria nodorum ) on wheat;
  • Synchytrium endobioticum on potatoes potato wart disease
  • Taphrina spp. e. g. T. deformans (leaf curl disease) on peaches and T. pruni (plum pocket) on plums
  • Thielaviopsis spp. black root rot
  • tobacco, pome fruits, vegetables, soybeans and cotton e. g. T. basicola (syn.
  • Tilletia spp. common bunt or stinking smut
  • cereals such as e. g. T. tritici (syn. T. caries, wheat bunt) and T. controversa (dwarf bunt) on wheat; Trichoderma harzianum on mushrooms ; Typhula incarnata (grey snow mold) on barley or wheat; Urocystis spp., e. g. U. occulta (stem smut) on rye; Uromyces spp. (rust) on vegetables, such as beans (e. g. U. appen- diculatus, syn. U. phaseoli), sugar beets (e.
  • beans e. g. U. appen- diculatus, syn. U. phaseoli
  • sugar beets e.
  • U. betae or U. beticola and on pulses (e.g. U. vignae, U. pisi, U. viciae-fabae and U. fabae) ⁇ Ustilago spp. (loose smut) on cereals (e. g. U. nuda and U. avaenae ), corn (e. g. U. maydis ⁇ corn smut) and sugar cane; Venturia spp. (scab) on apples (e. g. V. inaequalis) and pears; and Verticillium spp. (wilt) on various plants, such as fruits and ornamentals, vines, soft fruits, vegetables and field crops, e. g. V. longisporum on oilseed rape, V. dahliae on strawberries, oilseed rape, potatoes and tomatoes, and V. fungicola on mushrooms; Zymoseptoria tritici on cereals.
  • the compounds I, their mixtures with other active compounds as defined herein and compositions thereof, respectively, are particularly suitable for controlling the following plant diseases: Puccinia spp. (rusts) on various plants, for example, but not limited to P. triticina (brown or leaf rust), P. striiformis (stripe or yellow rust), P. hordei (dwarf rust), P. graminis (stem or black rust) or P. recondita (brown or leaf rust) on cereals, such as e. g. wheat, barley or rye, P. sorghi (common rust) on maize, P. polysora (southern rust) on maize; P.
  • Puccinia spp. rusts
  • rusts rusts
  • P. triticina brown or leaf rust
  • P. striiformis stripe or yellow rust
  • P. hordei dwarf rust
  • coro- nata e.g. on oats, P. sorghi und P. polysora on corn
  • Puccinia spp. on other crops, e.g. P. helia- thi on sunflower, P. arachidis on peanuts
  • Uromyces spp. on pulses and other crops crops, e.g. Uromyces viciae-fabae, Uromyces vigniae, Uromyces pisi, U. ciceris-arietini, U. betae syn U. beticola
  • Phakopsoraceae spp. on various plants, in particular Phakopsora pachyrhizi and P. meibomiae (soybean rust) on soybeans.
  • Fungicide-resistant strains of the above-mentioned phytopathgenic fungi have been reported, with strains resistant to one or more fungicides from various fungicidal mode of action classes being observed including but not limited to beta-tubulin assembly inhibitors, sterol demethyla- tion-inhibitors (DMI), quinone-outside-inhibitors (Qol) and succinate dehydrogenase inhibitors (SDHI).
  • compounds I are useful to control phytopathogenic fungi comprising at least one of the following mutations: E198A/G/K or F200Y in the beta-tubulin gene conferring resistance to beta-tubulin assembly inhibitors (Phytopathol (2008) 98: 397-404), I365N/S, V368F,
  • the compounds I and compositions thereof, respectively, are also suitable for controlling harmful fungi in the protection of stored products or harvest and in the protection of materials.
  • protection of materials is to be understood to denote the protection of technical and non-living materials, such as adhesives, glues, wood, paper and paperboard, textiles, leather, paint dispersions, plastics, cooling lubricants, fiber or fabrics, against the infestation and de- struction by harmful microorganisms, such as fungi and bacteria.
  • Ascomycetes such as Ophiostoma spp., Ceratocystis spp., Aureobasidium pullulans, Sclerophoma spp., Chaetomium spp., Humicola spp., Petriella spp., Trichurus spp.; Basidiomycetes such as Coni- ophora spp., Coriolus spp., Gloeophyllum spp., Lentinus spp., Pleurotus spp., Poria spp., Ser- pula spp.
  • yeast fungi are worthy of note: Candida spp. and Saccharomyces cerevisae.
  • the method of treatment according to the invention can also be used in the field of protecting stored products or harvest against attack of fungi and microorganisms.
  • the term "stored products” is understood to denote natural substances of plant or ani- mal origin and their processed forms, which have been taken from the natural life cycle and for which long-term protection is desired.
  • Stored products of crop plant origin such as plants or parts thereof, for example stalks, leafs, tubers, seeds, fruits or grains, can be protected in the freshly harvested state or in processed form, such as pre-dried, moistened, comminuted, ground, pressed or roasted, which process is also known as post-harvest treatment.
  • stored products are timber, whether in the form of crude timber, such as construction timber, electricity pylons and barriers, or in the form of finished articles, such as fur- niture or objects made from wood.
  • Stored products of animal origin are hides, leather, furs, hairs and the like.
  • the combinations according the present invention can prevent disadvantageous effects such as decay, discoloration or mold.
  • Preferably "stored products” is understood to de- note natural substances of plant origin and their processed forms, more preferably fruits and their processed forms, such as pomes, stone fruits, soft fruits and citrus fruits and their pro- De- Found forms.
  • the compounds I and compositions thereof, respectively, may be used for improving the health of a plant.
  • the invention also relates to a method for improving plant health by treating a plant, its propagation material and/or the locus where the plant is growing or is to grow with an effective amount of compounds I and compositions thereof, respectively.
  • plant health is to be understood to denote a condition of the plant and/or its prod- ucts which is determined by several indicators alone or in combination with each other such as yield (e. g. increased biomass and/or increased content of valuable ingredients), plant vigor (e. g. improved plant growth and/or greener leaves (“greening effect”)), quality (e. g. improved content or composition of certain ingredients) and tolerance to abiotic and/or biotic stress.
  • yield e. g. increased biomass and/or increased content of valuable ingredients
  • plant vigor e. g. improved plant growth and/or greener leaves (“greening effect”)
  • quality e. g. improved content or composition of certain ingredients
  • tolerance to abiotic and/or biotic stress e. g. improved content or composition of certain ingredients
  • the compounds of formula I can be present in different crystal modifications whose biological activity may differ. They are likewise subject matter of the present invention.
  • the compounds I are employed as such or in form of compositions by treating the fungi or the plants, plant propagation materials, such as seeds, soil, surfaces, materials or rooms to be pro- tected from fungal attack with a fungicidally effective amount of the active substances.
  • the ap- plication can be carried out both before and after the infection of the plants, plant propagation materials, such as seeds, soil, surfaces, materials or rooms by the fungi.
  • Plant propagation materials may be treated with compounds I as such or a composition com- prising at least one compound I prophylactically either at or before planting or transplanting.
  • the invention also relates to agrochemical compositions comprising an auxiliary and at least one compound I according to the invention.
  • An agrochemical composition comprises a fungicidally effective amount of a compound I.
  • effective amount denotes an amount of the composition or of the compounds I, which is sufficient for controlling harmful fungi on cultivated plants or in the protection of materials and which does not result in a substantial damage to the treated plants. Such an amount can vary in a broad range and is dependent on various factors, such as the fungal species to be controlled, the treated cultivated plant or material, the climatic conditions and the specific compound I used.
  • compositions e. g. solutions, emulsions, suspensions, dusts, powders, pastes, gran- ules, pressings, capsules, and mixtures thereof.
  • composition types are suspen- sions (e. g. SC, OD, FS), emulsifiable concentrates (e. g. EC), emulsions (e. g. EW, EO, ES, ME), capsules (e. g. CS, ZC), pastes, pastilles, wettable powders or dusts (e. g. WP, SP, WS, DP, DS), pressings (e.
  • suspen- sions e. g. SC, OD, FS
  • emulsifiable concentrates e. g. EC
  • emulsions e. g. EW, EO, ES, ME
  • capsules e. g. CS, ZC
  • pastes pastilles, wettable powder
  • compositions types are defined in the“Catalogue of pesticide formulation types and international coding system”, Technical Monograph No. 2, 6 th Ed. May 2008, CropLife International.
  • compositions are prepared in a known manner, such as described by Mollet and Grube- mann, Formulation technology, Wiley VCH, Weinheim, 2001 ; or Knowles, New developments in crop protection product formulation, Agrow Reports DS243, T&F Informa, London, 2005.
  • Suitable auxiliaries are solvents, liquid carriers, solid carriers or fillers, surfactants, disper- sants, emulsifiers, wetters, adjuvants, solubilizers, penetration enhancers, protective colloids, adhesion agents, thickeners, humectants, repellents, attractants, feeding stimulants, compatibil- izers, bactericides, anti-freezing agents, anti-foaming agents, colorants, tackifiers and binders.
  • Suitable solvents and liquid carriers are water and organic solvents, such as mineral oil frac- tions of medium to high boiling point, e. g.
  • kerosene diesel oil
  • oils of vegetable or animal origin aliphatic, cyclic and aromatic hydrocarbons, e. g. toluene, paraffin, tetrahydronaphthalene, alkyl- ated naphthalenes; alcohols, e. g. ethanol, propanol, butanol, benzyl alcohol, cyclohexanol; gly- cols; DMSO; ketones, e. g. cyclohexanone; esters, e. g. lactates, carbonates, fatty acid esters, gamma-butyrolactone; fatty acids; phosphonates; amines; amides, e. g. N-methyl pyrrolidone, fatty acid dimethyl amides; and mixtures thereof.
  • Suitable solid carriers or fillers are mineral earths, e. g. silicates, silica gels, talc, kaolins, lime- stone, lime, chalk, clays, dolomite, diatomaceous earth, bentonite, calcium sulfate, magnesium sulfate, magnesium oxide; polysaccharides, e. g. cellulose, starch; fertilizers, e. g. ammonium sulfate, ammonium phosphate, ammonium nitrate, ureas; products of vegetable origin, e. g. ce- real meal, tree bark meal, wood meal, nutshell meal, and mixtures thereof.
  • mineral earths e. g. silicates, silica gels, talc, kaolins, lime- stone, lime, chalk, clays, dolomite, diatomaceous earth, bentonite, calcium sulfate, magnesium sulfate, magnesium oxide
  • polysaccharides e.
  • Suitable surfactants are surface-active compounds, such as anionic, cationic, nonionic and amphoteric surfactants, block polymers, polyelectrolytes, and mixtures thereof. Such surfactants can be used as emulsifier, dispersant, solubilizer, wetter, penetration enhancer, protective col- loid, or adjuvant. Examples of surfactants are listed in McCutcheon’s, Vol.1 : Emulsifiers & De- tergents, McCutcheon’s Directories, Glen Rock, USA, 2008 (International Ed. or North American Ed.).
  • Suitable anionic surfactants are alkali, alkaline earth or ammonium salts of sulfonates, sul- fates, phosphates, carboxylates, and mixtures thereof.
  • sulfonates are alkylaryl sul- fonates, diphenyl sulfonates, alpha-olefin sulfonates, lignin sulfonates, sulfonates of fatty acids and oils, sulfonates of ethoxylated alkylphenols, sulfonates of alkoxylated arylphenols, sul- fonates of condensed naphthalenes, sulfonates of dodecyl- and tridecylbenzenes, sulfonates of naphthalenes and alkyl naphthalenes, sulfosuccinates or sulfosuccinamates.
  • Examples of sul- fates are sulfates of fatty acids and oils, of ethoxylated alkylphenols, of alcohols, of ethoxylated alcohols, or of fatty acid esters.
  • Examples of phosphates are phosphate esters.
  • Examples of carboxylates are alkyl carboxylates, and carboxylated alcohol or alkylphenol ethoxylates.
  • Suitable nonionic surfactants are alkoxylates, N-substituted fatty acid amides, amine oxides, esters, sugar-based surfactants, polymeric surfactants, and mixtures thereof.
  • alkoxylates are compounds such as alcohols, alkylphenols, amines, amides, arylphenols, fatty acids or fatty acid esters which have been alkoxylated with 1 to 50 equivalents.
  • Ethylene oxide and/or propylene oxide may be employed for the alkoxylation, preferably ethylene oxide.
  • Exam- ples of N-substituted fatty acid amides are fatty acid glucamides or fatty acid alkanolamides.
  • esters are fatty acid esters, glycerol esters or monoglycerides.
  • sugar- based surfactants are sorbitans, ethoxylated sorbitans, sucrose and glucose esters or alkylpoly- glucosides.
  • polymeric surfactants are home- or copolymers of vinyl pyrrolidone, vi- nyl alcohols, or vinyl acetate.
  • Suitable cationic surfactants are quaternary surfactants, for example quaternary ammonium compounds with one or two hydrophobic groups, or salts of long-chain primary amines.
  • Suitable amphoteric surfactants are alkylbetains and imidazolines.
  • Suitable block polymers are block pol- ymers of the A-B or A-B-A type comprising blocks of polyethylene oxide and polypropylene ox- ide, or of the A-B-C type comprising alkanol, polyethylene oxide and polypropylene oxide.
  • Suita- ble polyelectrolytes are polyacids or polybases. Examples of polyacids are alkali salts of poly- acrylic acid or polyacid comb polymers. Examples of polybases are polyvinyl amines or polyeth- ylene amines.
  • Suitable adjuvants are compounds, which have a negligible or even no pesticidal activity themselves, and which improve the biological performance of the compound I on the target. Ex- amples are surfactants, mineral or vegetable oils, and other auxiliaries. Further examples are listed by Knowles, Adjuvants and additives, Agrow Reports DS256, T&F Informa UK, 2006, chapter 5.
  • Suitable thickeners are polysaccharides (e. g. xanthan gum, carboxymethyl cellulose), inor- ganic clays (organically modified or unmodified), polycarboxylates, and silicates.
  • Suitable bactericides are bronopol and isothiazolinone derivatives such as alkylisothiazoli- nones and benzisothiazolinones.
  • Suitable anti-freezing agents are ethylene glycol, propylene glycol, urea and glycerin.
  • Suitable anti-foaming agents are silicones, long chain alcohols, and salts of fatty acids.
  • Suitable colorants are pigments of low water solubility and water- soluble dyes.
  • examples are inorganic colorants (e. g. iron oxide, titan oxide, iron hexacyanofer- rate) and organic colorants (e. g. alizarin-, azo- and phthalocyanine colorants).
  • Suitable tackifiers or binders are polyvinyl pyrrolidones, polyvinyl acetates, polyvinyl alcohols, polyacrylates, biological or synthetic waxes, and cellulose ethers.
  • composition types and their preparation are:
  • a compound I and 5-15 wt% wetting agent e. g. alcohol alkoxylates
  • a water-soluble solvent e. g. alcohols
  • a compound I and 1-10 wt% dispersant e. g. polyvinyl pyrrolidone
  • organic solvent e. g. cyclohexanone
  • EC Emulsifiable concentrates
  • emulsifiers e. g. calcium dodecylbenzenesulfonate and castor oil ethoxylate
  • water-insoluble organic solvent e. g. aromatic hydro- carbon
  • Emulsions (EW, EO, ES)
  • emulsifiers e. g. calcium dodecylbenzenesulfonate and castor oil ethoxylate
  • water-insoluble organic solvent e. g. aro- matic hydrocarbon
  • a compound I In an agitated ball mill, 20-60 wt% of a compound I are comminuted with addition of 2-10 wt% dispersants and wetting agents (e. g. sodium lignosulfonate and alcohol ethoxylate), 0.1-2 wt% thickener (e. g. xanthan gum) and water ad 100 wt% to give a fine active substance suspension. Dilution with water gives a stable suspension of the active substance. For FS type composition up to 40 wt% binder (e. g. polyvinyl alcohol) is added.
  • dispersants and wetting agents e. g. sodium lignosulfonate and alcohol ethoxylate
  • 0.1-2 wt% thickener e. g. xanthan gum
  • Water-dispersible granules and water-soluble granules (WG, SG) 50-80 wt% of a compound I are ground finely with addition of dispersants and wetting agents (e. g. sodium lignosulfonate and alcohol ethoxylate) ad 100 wt% and prepared as water-dis- persible or water-soluble granules by means of technical appliances (e. g. extrusion, spray tower, fluidized bed). Dilution with water gives a stable dispersion or solution of the active sub- stance.
  • dispersants and wetting agents e. g. sodium lignosulfonate and alcohol ethoxylate
  • wt% of a compound I are ground in a rotor-stator mill with addition of 1-5 wt% disper- sants (e. g. sodium lignosulfonate), 1-3 wt% wetting agents (e. g. alcohol ethoxylate) and solid carrier (e. g. silica gel) ad 100 wt%. Dilution with water gives a stable dispersion or solution of the active substance.
  • disper- sants e. g. sodium lignosulfonate
  • wetting agents e. g. alcohol ethoxylate
  • solid carrier e. g. silica gel
  • a compound I In an agitated ball mill, 5-25 wt% of a compound I are comminuted with addition of 3-10 wt% dispersants (e. g. sodium lignosulfonate), 1-5 wt% thickener (e. g. carboxymethyl cellulose) and water ad 100 wt% to give a fine suspension of the active substance. Dilution with water gives a stable suspension of the active substance.
  • dispersants e. g. sodium lignosulfonate
  • 1-5 wt% thickener e. g. carboxymethyl cellulose
  • 5-20 wt% of a compound I are added to 5-30 wt% organic solvent blend (e. g. fatty acid dime- thyl amide and cyclohexanone), 10-25 wt% surfactant blend (e. g. alcohol ethoxylate and ar- ylphenol ethoxylate), and water ad 100 %.
  • organic solvent blend e. g. fatty acid dime- thyl amide and cyclohexanone
  • surfactant blend e. g. alcohol ethoxylate and ar- ylphenol ethoxylate
  • An oil phase comprising 5-50 wt% of a compound I, 0-40 wt% water insoluble organic solvent (e. g. aromatic hydrocarbon), 2-15 wt% acrylic monomers (e. g. methylmethacrylate, methacrylic acid and a di- or triacrylate) are dispersed into an aqueous solution of a protective colloid (e. g. polyvinyl alcohol). Radical polymerization results in the formation of poly(meth)acrylate micro- capsules.
  • an oil phase comprising 5-50 wt% of a compound I according to the in- vention, 0-40 wt% water insoluble organic solvent (e. g. aromatic hydrocarbon), and an isocya- nate monomer (e.
  • g. diphenylmethene-4,4’-diisocyanatae are dispersed into an aqueous solu- tion of a protective colloid (e. g. polyvinyl alcohol).
  • a protective colloid e. g. polyvinyl alcohol.
  • the addition of a polyamine results in the formation of polyurea microcapsules.
  • the monomers amount to 1- 10 wt%.
  • the wt% relate to the total CS composition.
  • Dustable powders (DP, DS)
  • 1-10 wt% of a compound I are ground finely and mixed intimately with solid carrier (e. g. finely divided kaolin) ad 100 wt%.
  • solid carrier e. g. finely divided kaolin
  • a compound I 0.5-30 wt% of a compound I is ground finely and associated with solid carrier (e. g. silicate) ad 100 wt%.
  • solid carrier e. g. silicate
  • Granulation is achieved by extrusion, spray-drying or fluidized bed.
  • organic solvent e. g. aromatic hydrocarbon
  • compositions types i) to xiii) may optionally comprise further auxiliaries, such as 0.1-1 wt% bactericides, 5-15 wt% anti-freezing agents, 0.1-1 wt% anti-foaming agents, and 0.1-1 wt% colorants.
  • the agrochemical compositions generally comprise between 0.01 and 95%, preferably be- tween 0.1 and 90%, more preferably between 1 and 70%, and in particular between 10 and 60%, by weight of active substance.
  • the active substances are employed in a purity of from 90% to 100%, preferably from 95% to 100% (according to NMR spectrum).
  • solutions for seed treatment (LS), Suspoemulsions (SE), flowable concentrates (FS), powders for dry treat- ment (DS), water-dispersible powders for slurry treatment (WS), water-soluble powders (SS), emulsions (ES), emulsifiable concentrates (EC), and gels (GF) are usually employed.
  • the com- positions in question give, after two-to-tenfold dilution, active substance concentrations of from 0.01 to 60% by weight, preferably from 0.1 to 40%, in the ready-to-use preparations. Application can be carried out before or during sowing.
  • Methods for applying compound I and compositions thereof, respectively, onto plant propagation material, especially seeds include dressing, coat- ing, pelleting, dusting, and soaking as well as in-furrow application methods.
  • com- pound I or the compositions thereof, respectively are applied on to the plant propagation mate- rial by a method such that germination is not induced, e. g. by seed dressing, pelleting, coating and dusting.
  • the amounts of active substances applied are, depending on the kind of effect desired, from 0.001 to 2 kg per ha, preferably from 0.005 to 2 kg per ha, more preferably from 0.05 to 0.9 kg per ha, and in particular from 0.1 to 0.75 kg per ha.
  • amounts of active substance of from 0.1 to 1000 g, preferably from 1 to 1000 g, more preferably from 1 to 100 g and most preferably from 5 to 100 g, per 100 kilogram of plant propa- gation material (preferably seeds) are generally required.
  • the amount of active substance applied depends on the kind of application area and on the desired effect. Amounts customarily applied in the protection of materials are 0.001 g to 2 kg, preferably 0.005 g to 1 kg, of active substance per cubic meter of treated material.
  • oils, wetters, adjuvants, fertilizer, or micronutrients, and further pesticides may be added to the active substances or the compositions comprising them as premix or, if appropriate not until immediately prior to use (tank mix).
  • pesticides e. g. herbicides, insecticides, fungicides, growth regulators, safeners, biopesticides
  • These agents can be admixed with the compositions according to the invention in a weight ratio of 1 : 100 to 100: 1 , preferably 1 : 10 to 10: 1.
  • a pesticide is generally a chemical or biological agent (such as pestidal active ingredient, compound, composition, virus, bacterium, antimicrobial or disinfectant) that through its effect deters, incapacitates, kills or otherwise discourages pests.
  • Target pests can include insects, plant pathogens, weeds, mollusks, birds, mammals, fish, nematodes (roundworms), and mi- crobes that destroy property, cause nuisance, spread disease or are vectors for disease.
  • pesticide includes also plant growth regulators that alter the expected growth, flowering, or reproduction rate of plants; defoliants that cause leaves or other foliage to drop from a plant, usually to facilitate harvest; desiccants that promote drying of living tissues, such as unwanted plant tops; plant activators that activate plant physiology for defense of against certain pests; safeners that reduce unwanted herbicidal action of pesticides on crop plants; and plant growth promoters that affect plant physiology e.g. to increase plant growth, biomass, yield or any other quality parameter of the harvestable goods of a crop plant.
  • the user applies the composition according to the invention usually from a predosage device, a knapsack sprayer, a spray tank, a spray plane, or an irrigation system.
  • the agrochem- ical composition is made up with water, buffer, and/or further auxiliaries to the desired applica- tion concentration and the ready-to-use spray liquor or the agrochemical composition according to the invention is thus obtained.
  • 20 to 2000 liters, preferably 50 to 400 liters, of the ready-to-use spray liquor are applied per hectare of agricultural useful area.
  • individual components of the composition according to the in- vention such as parts of a kit or parts of a binary or ternary mixture may be mixed by the user himself in a spray tank or any other kind of vessel used for applications (e. g. seed treater drums, seed pelleting machinery, knapsack sprayer) and further auxiliaries may be added, if ap- intestinalte.
  • one embodiment of the invention is a kit for preparing a usable pesticidal com- position, the kit comprising a) a composition comprising component 1) as defined herein and at least one auxiliary; and b) a composition comprising component 2) as defined herein and at least one auxiliary; and optionally c) a composition comprising at least one auxiliary and option- ally a further active component 3) as defined herein.
  • pesticides II e. g. pesticidally-active substances and biopesticides
  • the compounds I in conjunction with which the compounds I can be used, is intended to illustrate the possible com- binations but does not limit them:
  • coumoxystrobin (A.1.3), dimoxystrobin (A.1.4), enestroburin (A.1.5), fenaminstrobin (A.1.6), fenoxystrobin/flufenoxystrobin (A.1.7), fluoxastrobin (A.1.8), kresoxim-methyl (A.1.9), man- destrobin (A.1.10), metominostrobin (A.1.1 1), orysastrobin (A.1.12), picoxystrobin (A.1.13), pyraclostrobin (A.1.14), pyrametostrobin (A.1.15), pyraoxystrobin (A.1.16), trifloxystrobin
  • respiration inhibitors diflumetorim (A.4.1); nitrophenyl derivates: binapacryl (A.4.2), di- nobuton (A.4.3), dinocap (A.4.4), fluazinam (A.4.5), meptyldinocap (A.4.6), ferimzone
  • organometal compounds organometal compounds: fentin salts, e. g. fentin-acetate (A.4.8), fentin chloride (A.4.9) or fentin hydroxide (A.4.10); ametoctradin (A.4.11); silthiofam (A.4.12);
  • - C14 demethylase inhibitors triazoles: azaconazole (B.1.1), bitertanol (B.1.2), bromucona- zole (B.1.3), cyproconazole (B.1.4), difenoconazole (B.1.5), diniconazole (B.1.6), dinicona- zole-M (B.1.7), epoxiconazole (B.1.8), fenbuconazole (B.1.9), fluquinconazole (B.1.10), flusi- lazole (B.1.11), flutriafol (B.1.12), hexaconazole (B.1.13), imibenconazole (B.1.14), ipcona- zole (B.1.15), metconazole (B.1.17), myclobutanil (B.1.18), oxpoconazole (B.1.19), paclobu- trazole (B.1.20), penconazole (
  • Sterol biosynthesis inhibitors chlorphenomizole (B.4.1); C) Nucleic acid synthesis inhibitors
  • benalaxyl (C.1.1), benalaxyl-M (C.1.2), kiralaxyl (C.1.3), metalaxyl (C.1.4), metalaxyl-M (C.1.5), ofurace (C.1.6), oxadixyl (C.1.7);
  • nucleic acid synthesis inhibitors hymexazole (C.2.1), octhilinone (C.2.2), oxolinic acid (C.2.3), bupirimate (C.2.4), 5-fluorocytosine (C.2.5), 5-fluoro-2-(p-tolylmethoxy)pyrimidin- 4-amine (C.2.6), 5-fluoro-2-(4-fluorophenylmethoxy)pyrimidin-4-amine (C.2.7), 5-fluoro- 2-(4-chlorophenylmethoxy)pyrimidin-4 amine (C.2.8);
  • tubulin inhibitors benomyl (D.1.1), carbendazim (D.1.2), fuberidazole (D1.3), thiabendazole (D.1.4), thiophanate-methyl (D.1.5), pyridachlometyl (D.1.6), N-ethyl-2-[(3-ethynyl-8-methyl- 6-quinolyl)oxy]butanamide (D.1.8), N-ethyl-2-[(3-ethynyl-8-methyl-6-quinolyl)oxy]-2-methyl- sulfanyl-acetamide (D.1.9), 2-[(3-ethynyl-8-methyl-6-quinolyl)oxy]-N-(2-fluoroethyl)bu- tanamide (D.1.10), 2-[(3-ethynyl-8-methyl-6-quinolyl)oxy]-N-(2-fluoroethyl)-2-methoxy-acet- amide (D.1.11)
  • diethofencarb (D.2.1), ethaboxam (D.2.2), pencycuron (D.2.3), fluopicolide (D.2.4), zoxamide (D.2.5), metrafenone (D.2.6), pyriofenone (D.2.7), phenamac- ril (D.2.8);
  • cyprodinil E.1.1
  • mepanipyrim E.1.2
  • pyrimethanil E.1.3
  • blasticidin-S (E.2.1), kasugamycin (E.2.2), kasugamycin hydro- chloride-hydrate (E.2.3), mildiomycin (E.2.4), streptomycin (E.2.5), oxytetracyclin (E.2.6);
  • fluoroimid F.1.1
  • iprodione F.1.2
  • procymidone F.1.3
  • vinclozolin F.1.4
  • fludioxonil F.1.5
  • quinoxyfen F.2.1
  • edifenphos (G .1.1), iprobenfos (G.1.2), pyrazophos (G.1.3), isoprothiolane (G.1.4);
  • dicloran G.2.1
  • quintozene G.2.2
  • tecnazene G.2.3
  • tolclofos-methyl G.2.4
  • biphenyl G.2.5
  • chloroneb G.2.6
  • etridiazole G.2.7
  • zinc thiazole G.2.8
  • dimethomorph G.3.1
  • flumorph G.3.2
  • mandipropamid G.3.3
  • pyrimorph G.3.4
  • benthiavalicarb G.3.5
  • iprovalicarb G.3.6
  • valifenalate G.3.7
  • propamocarb (G.4.1);
  • oxathiapiprolin G.5.1
  • fluoxapiprolin G.5.3
  • 4-[1-[2- [3-(difluoromethyl)-5-methyl-pyrazol-1-yl]acetyl]-4-piperidyl]-N-tetralin-1-yl-pyridine-2-carbox- amide G.5.4
  • 4-[1-[2-[3,5-bis(difluoromethyl)pyrazol-1-yl]acetyl]-4-piperidyl]-N-tetralin-1-yl- pyridine-2-carboxamide G.5.5
  • 4-[1-[2-[3-(difluoromethyl)-5-(trifluoromethyl)pyrazol-1-yl]ac- etyl]-4-piperidyl]-N-tetralin-1-yl-pyridine-2-carboxamide G.5.6
  • 4-[1-[2-[5-cyclopropyl oxathiapiprolin
  • organochlorine compounds anilazine (H.3.1), chlorothalonil (H.3.2), captafol (H.3.3), captan (H.3.4), folpet (H.3.5), dichlofluanid (H.3.6), dichlorophen (H.3.7), hexachlorobenzene (H.3.8), pentachlorphenole (H.3.9) and its salts, phthalide (H.3.10), tolylfluanid (H.3.11);
  • guanidine H.4.1
  • dodine H.4.2
  • dodine free base H.4.3
  • guazatine H.4.4
  • guazatine-acetate H.4.5
  • iminoctadine H.4.6
  • iminoctadine-triacetate H.4.7
  • iminoctadine-tris(albesilate) H.4.8
  • dithianon H.4.9
  • 2,6-dimethyl-1H,5H-[1 ,4]di- thiino[2,3-c:5,6-c']dipyrrole-1 ,3,5,7(2H,6H)-tetraone H.4.10);
  • - melanin synthesis inhibitors pyroquilon (1.2.1), tricyclazole (1.2.2), carpropamid (1.2.3), dicy- clomet (1.2.4), fenoxanil (1.2.5);
  • abscisic acid (M.1.1), amidochlor, ancymidol, 6-benzylaminopurine, brassinolide, butralin, chlormequat, chlormequat chloride, choline chloride, cyclanilide, daminozide, dikegulac, dime- thipin, 2,6-dimethylpuridine, ethephon, flumetralin, flurprimidol, fluthiacet, forchlorfenuron, gib- berellic acid, inabenfide, indole-3-acetic acid , maleic hydrazide, mefluidide, mepiquat, mepiquat chloride, naphthaleneacetic acid, N-6-benzyladenine, paclobutrazol, prohexadione, prohexadi- one-calcium, prohydrojasmon, thidiazuron, triapenthenol, tributyl phosphorotrithioate
  • Lipid biosynthesis inhibitors alloxydim, alloxydim-sodium, butroxydim, clethodim,
  • clodinafop clodinafop-propargyl, cycloxydim, cyhalofop, cyhalofop-butyl, diclofop, diclofop- methyl, fenoxaprop, fenoxaprop-ethyl, fenoxaprop-P, fenoxaprop-P-ethyl, fluazifop, fluazifop- butyl, fluazifop-P, fluazifop-P-butyl, haloxyfop, haloxyfop-methyl, haloxyfop-P, haloxyfop-P- methyl, metamifop, pinoxaden, profoxydim, propaquizafop, quizalofop, quizalofop-ethyl, quizalofop-tefuryl, quizalofop-P, quizalofop-P-ethyl,
  • N.2 ALS inhibitors amidosulfuron, azimsulfuron, bensulfuron, bensulfuron-methyl, chlorimuron, chlorimuron-ethyl, chlorsulfuron, cinosulfuron, cyclosulfamuron, ethametsulfuron, ethamet- sulfuron-methyl, ethoxysulfuron, flazasulfuron, flucetosulfuron, flupyrsulfuron, flupyrsulfuron- methyl-sodium, foramsulfuron, halosulfuron, halosulfuron-methyl, imazosulfuron, iodosulfu- ron, iodosulfuron-methyl-sodium, iofensulfuron, iofensulfuron-sodium, mesosulfuron, meta- zosulfuron, metsulfuron, metsulfuron-methyl, nic
  • N.3 Photosynthesis inhibitors amicarbazone; chlorotriazine; ametryn, atrazine, chloridazone, cyanazine, desmetryn, dimethametryn.hexazinone, metribuzin, prometon, prometryn, pro- pazine, simazine, simetryn, terbumeton, terbuthylazin, terbutryn, trietazin; chlorobromuron, chlorotoluron, chloroxuron, dimefuron, diuron, fluometuron, isoproturon, isouron, linuron, metamitron, methabenzthiazuron, metobenzuron, metoxuron, monolinuron, neburon, sidu- ron, tebuthiuron, thiadiazuron, desmedipham, karbutilat, phenmedipham, phenmedipham- ethyl, bromofenoxim, brom
  • N.4 protoporphyrinogen-IX oxidase inhibitors acifluorfen, acifluorfen-sodium, azafenidin, ben- carbazone, benzfendizone, bifenox, butafenacil, carfentrazone, carfentrazone-ethyl, chlor- methoxyfen, cinidon-ethyl, fluazolate, flufenpyr, flufenpyr-ethyl, flumiclorac, flumiclorac-pen- tyl, flumioxazin, fluoroglycofen, fluoroglycofen-ethyl, fluthiacet, fluthiacet-methyl, fomesafen, halosafen, lactofen, oxadiargyl, oxadiazon, oxyfluorfen, pentoxazone, profluazol, pyraclonil, pyraflufen, pyraflufen
  • N.5 Bleacher herbicides beflubutamid, diflufenican, fluridone, flurochloridone, flurtamone,
  • norflurazon picolinafen, 4-(3-trifluoromethyhphenoxy)-2-(4-trifluoromethylphenyl)pyrimidine (180608-33-7); benzobicyclon, benzofenap, bicyclopyrone, clomazone, fenquintrione, isoxaflutole, mesotrione, pyrasulfotole, pyrazolynate, pyrazoxyfen, sulcotrione, tefuryltrione, tembotrione, tolpyralate, topramezone; aclonifen, amitrole, flumeturon;
  • N.6 EPSP synthase inhibitors glyphosate, glyphosate-isopropylammonium, glyposate-potas- sium, glyphosate-trimesium (sulfosate);
  • Glutamine synthase inhibitors bilanaphos (bialaphos), bilanaphos-sodium, glufosinate, glufosinate-P, glufosinate-ammonium;
  • Mitosis inhibitors benfluralin, butralin, dinitramine, ethalfluralin, fluchloralin, oryzalin, pendi- methalin, prodiamine, trifluralin; amiprophos, amiprophos-methyl, butamiphos; chlorthal, chlorthal-dimethyl, dithiopyr, thiazopyr, propyzamide, tebutam; carbetamide, chlorpropham, flamprop, flamprop-isopropyl, flamprop-methyl, flamprop-M-isopropyl, flamprop-M-methyl, propham;
  • N.10 VLCFA inhibitors acetochlor, alachlor, butachlor, dimethachlor, dimethenamid, dimethena- mid-P, metazachlor, metolachlor, metolachlor-S, pethoxamid, pretilachlor, propachlor, prop- isochlor, thenylchlor, flufenacet, mefenacet, diphenamid, naproanilide, napropamide, napro- pamide-M, fentrazamide, anilofos, cafenstrole, fenoxasulfone, ipfencarbazone, piperophos, pyroxasulfone, isoxazoline compounds of the formulae 11.1 , II.2, II.3, II.4, II.5, II.6, II.7, II.8 and II.9
  • N.11 Cellulose biosynthesis inhibitors chlorthiamid, dichlobenil, flupoxam, indaziflam, isoxaben, triaziflam, 1-cyclohexyl-5-pentafluorphenyloxy-14-[1 ,2,4,6]thiatriazin-3-ylamine (175899-01- 1);
  • N.12 Decoupler herbicides dinoseb, dinoterb, DNOC and its salts
  • N.13 Auxinic herbicides 2,4-D and its salts and esters, clacyfos, 2,4-DB and its salts and es- ters, aminocyclopyrachlor and its salts and esters, aminopyralid and its salts such as amino- pyralid-dimethylammonium, aminopyralid-tris(2-hydroxypropyl)ammonium and its esters, benazolin, benazolin-ethyl, chloramben and its salts and esters, clomeprop, clopyralid and its salts and esters, dicamba and its salts and esters, dichlorprop and its salts and esters, dichlorprop-P and its salts and esters, fluroxypyr, fluroxypyr-butometyl, fluroxypyr-meptyl, halauxifen and its salts and esters (943832-60-8); MCPA and its salts and esters, MCPA- thioethy
  • N.14 Auxin transport inhibitors diflufenzopyr, diflufenzopyr-sodium, naptalam, naptalam- sodium;
  • Acetylcholine esterase (AChE) inhibitors aldicarb (0.1.1), alanycarb (0.1.2), bendiocarb
  • GABA-gated chloride channel antagonists endosulfan (0.2.1), chlordane (0.2.2), ethiprole (0.2.3), fipronil (0.2.4), flufiprole (0.2.5), pyrafluprole (0.2.6), pyriprole (0.2.7);
  • Nicotinic acetylcholine receptor agonists acetamiprid (0.4.1), clothianidin (0.4.2), cycloxaprid (0.4.3), dinotefuran (0.4.4), imidacloprid (0.4.5), nitenpyram (0.4.6), thiacloprid (0.4.7), thiamethoxam (0.4.8), 4,5-dihydro-N-nitro-1-(2-oxiranylmethyl)-1H-imidazol-2-amine (0.4.9), (2E)-1-[(6-chloropyridin-3-yl)methyl] -N- itro-2-pentylidenehydrazinecarboximidam- ide (0.4.10), 1-[(6-chloropyridin-3-yl)methyl]-7-methyl-8-nitro-5-propoxy-1 ,2,3,5,6,7-hexahy- droimidazo[1 ,2-a]pyridine (0.4.11), nicotine
  • Nicotinic acetylcholine receptor allosteric activators spinosad (0.5.1), spinetoram (0.5.2);
  • Chloride channel activators abamectin (0.6.1), emamectin benzoate (0.6.2), ivermectin (0.6.3), lepimectin (0.6.4), milbemectin (0.6.5);
  • 0.8 miscellaneous non-specific (multi-site) inhibitors methyl bromide (0.8.1) and other alkyl halides, chloropicrin (0.8.2), sulfuryl fluoride (0.8.3), borax (0.8.4), tartar emetic (0.8.5);
  • 0.9 Chordotonal organ TRPV channel modulators pymetrozine (0.9.1), pyrifluquinazon (0.9.2), flonicamid (0.9.3);
  • Mite growth inhibitors clofentezine (0.10.1), hexythiazox (0.10.2), diflovidazin (0.10.3), etoxazole (0.10.4);
  • Bacillus thuringiensis Bacillus sphaeri- cus and the insecticdal proteins they produce: Bacillus thuringiensis subsp. Israelensis (0.11.1), Bacillus sphaericus (0.11.2), Bacillus thuringiensis subsp. aizawai (0.11.3), Bacil lus thuringiensis subsp. kurstaki (0.11.4), Bacillus thuringiensis subsp.
  • Inhibitors of mitochondrial ATP synthase diafenthiuron (0.12.1), azocyclotin (0.12.2), cyhexatin (0.12.3), fenbutatin oxide (0.12.4), propargite (0.12.5), tetradifon (0.12.6);
  • Nicotinic acetylcholine receptor (nAChR) channel blockers bensultap (0.14.1), cartap hy- drochloride (0.14.2), thiocyclam (0.14.3), thiosultap sodium (0.14.4);
  • Inhibitors of the chitin biosynthesis type 0 bistrifluron (0.15.1), chlorfluazuron (0.15.2), diflubenzuron (0.15.3), flucycloxuron (0.15.4), flufenoxuron (0.15.5), hexaflumuron
  • Inhibitors of the chitin biosynthesis type 1 buprofezin (0.16.1);
  • Ecdyson receptor agonists methoxyfenozide (0.18.1), tebufenozide (0.18.2), halofeno- zide (0.18.3), fufenozide (0.18.4), chromafenozide (0.18.5);
  • Octopamin receptor agonists amitraz (0.19.1);
  • Mitochondrial complex III electron transport inhibitors hydramethylnon (0.20.1), acequi- nocyl (0.20.2), fluacrypyrim (0.20.3), bifenazate (0.20.4);
  • Mitochondrial complex I electron transport inhibitors fenazaquin (0.21.1), fenpyroximate (0.21.2), pyrimidifen (0.21.3), pyridaben (0.21.4), tebufenpyrad (0.21.5), tolfenpyrad (0.21.6), rotenone (0.21.7);
  • Inhibitors of the of acetyl CoA carboxylase spirodiclofen (0.23.1), spiromesifen (0.23.2), spirotetramat (0.23.3), spiropidion (0.23.4);
  • Mitochondrial complex IV electron transport inhibitors aluminium phosphide (0.24.1), cal- cium phosphide (0.24.2), phosphine (0.24.3), zinc phosphide (0.24.4), cyanide (0.24.5);
  • Mitochondrial complex II electron transport inhibitors cyenopyrafen (0.25.1), cyflumetofen (0.25.2);
  • insecticidal active compounds of unknown or uncertain mode of action afidopyropen (0.28.1), afoxolaner (0.28.2), azadirachtin (0.28.3), amidoflumet (0.28.4), benzoximate (0.28.5), broflanilide (0.28.6), bromopropylate (0.28.7), chinomethionat (0.28.8), cryolite (0.28.9), dicloromezotiaz (0.28.10), dicofol (0.28.1 1), flufenerim (0.28.12), flometoquin (0.28.13), fluensulfone (0.28.14), fluhexafon (0.28.15), fluopyram (0.28.16), fluralaner (0.28.17), metoxadiazone (0.28.18), piperonyl butoxide (0.28.19), pyflubumide (0.28.20), pyridalyl (0.28.21), tioxazafen (0.
  • component 2 The active substances referred to as component 2, their preparation and their activity e. g. against harmful fungi is known (cf. : http://www.alanwood.net/pesticides/); these substances are commercially available.
  • the compounds described by lUPAC nomenclature, their preparation and their pesticidal activity are also known (cf. Can. J. Plant Sci. 48(6), 587-94, 1968;
  • the present invention furthermore relates to agrochemical compositions comprising a mixture of at least one compound I (component 1) and at least one further active substance useful for plant protection, e. g. selected from the groups A) to O) (component 2), in particular one further fungicide, e. g. one or more fungicide from the groups A) to K), as described above, and if de- sired one suitable solvent or solid carrier.
  • agrochemical compositions comprising a mixture of at least one compound I (component 1) and at least one further active substance useful for plant protection, e. g. selected from the groups A) to O) (component 2), in particular one further fungicide, e. g. one or more fungicide from the groups A) to K), as described above, and if de- sired one suitable solvent or solid carrier.
  • Those mixtures are of particular interest, since many of them at the same application rate show higher efficiencies against harmful fungi.
  • the order of application is not essential for working of the present invention.
  • the time between both applications may vary e. g. between 2 hours to 7 days. Also, a broader range is possible ranging from 0.25 hour to 30 days, preferably from 0.5 hour to 14 days, particularly from 1 hour to 7 days or from 1.5 hours to 5 days, even more preferred from 2 hours to 1 day.
  • the weight ratio of the com- ponent 1) and the component 2) generally depends from the properties of the active compo- nents used, usually it is in the range of from 1 :10,000 to 10,000:1 , often it is in the range of from 1 :100 to 100:1 , regularly in the range of from 1 :50 to 50:1 , preferably in the range of from 1 :20 to 20:1 , more preferably in the range of from 1 :10 to 10:1 , even more preferably in the range of from 1 :4 to 4: 1 and in particular in the range of from 1 :2 to 2: 1.
  • the weight ratio of the component 1) and the component 2) usually is in the range of from 1000:1 to 1 :1 , often in the range of from 100: 1 to 1 :1 , regularly in the range of from 50:1 to 1 :1 , preferably in the range of from 20:1 to 1 :1 , more preferably in the range of from 10:1 to 1 :1 , even more preferably in the range of from 4:1 to 1 :1 and in particular in the range of from 2:1 to 1 :1.
  • the weight ratio of the component 1) and the component 2) usually is in the range of from 1 :1 to 1 :1000, often in the range of from 1 :1 to 1 :100, regularly in the range of from 1 :1 to 1 :50, preferably in the range of from 1 :1 to 1 :20, more preferably in the range of from 1 :1 to 1 :10, even more preferably in the range of from 1 :1 to 1 :4 and in particular in the range of from 1 :1 to 1 :2.
  • the weight ratio of component 1) and component 2) depends from the properties of the active substances used, usually it is in the range of from 1 :100 to 100:1 , regularly in the range of from 1 :50 to 50:1 , preferably in the range of from 1 :20 to 20:1 , more preferably in the range of from 1 :10 to 10:1 and in particular in the range of from 1 :4 to 4:1 , and the weight ratio of component 1) and component 3) usually it is in the range of from 1 :100 to 100:1 , regularly in the range of from 1 :50 to 50:1 , preferably in the range of from 1 :20 to 20:1 , more preferably in the range of from 1 :10 to 10:1 and in particular in the range of from 1 :4 to 4: 1.
  • Any further active components are, if desired, added in a ratio of from 20:1 to 1 :20 to the com- ponent 1).
  • the present invention furthermore relates to mixtures comprising one compound of the formula I (component 1 , a group represented by the expression“(I)”) and one pesticide II (component 2), wherein pesticide II is an active ingredient selected from the groups A) to O) de- fined above.
  • the mixtures of active substances can be prepared as compositions comprising besides the active ingredients at least one inert ingredient (auxiliary) by usual means, e. g. by the means given for the compositions of compounds I.
  • the mixtures of active substances according to the present invention are suitable as fungi- cides, as are the compounds of formula I. They are distinguished by an outstanding effective- ness against a broad spectrum of phytopathogenic fungi, especially from the classes of the As- comycetes, Basidiomycetes, Deuteromycetes and Peronosporomycetes (syn. Oomycetes). In addition, it is referred to the explanations regarding the fungicidal activity of the compounds and the compositions containing compounds I, respectively. Synthesis examples
  • the compounds of the formula I can be prepared according to the methods outlined below.
  • reaction mixture was quenched with 200 ml aq. NH4CI-solution and extracted with methyl-t-butylether, the organic layer was dried over sodium sulfate and concentrated.
  • the residue was purified by column-chromatog- raphy using petrolether/methyl-t-butylether-mixtures to give 12.5 g (73% of theory) 5-cyclopro- pyl-2-isobutyl-2-methyl-pent-4-ynoate as yellow oil.
  • reaction mixture was concen- trated, the residue was dissolved in dichloromethane and this solution was dropped into a solu- tion of 0,474 g (3,21 mmol) 1 -cyclopropyl-4, 6-dimethyl-hept-1-yn-4-amine and 0,432 g (4,28 mmol) triethylamine in dichloromethane.
  • the reaction mixture was stirred for 16 h at 40°C. Then water was added, the phases were separated and the aqueous layer was extracted with di- chloromethane. The combined organic layers were dried over sodium sulfate and concentrated.
  • reaction mixture was concentrated, the residue was dissolved in dichloromethane and this solution was dropped into a solution of 0,536 g (2,8 mmol) 4,4-dimethyl-1-phenyl-pent-1-yn-3- amine and 0,808 g (8 mmol) triethylamine in dichloromethane at 0°C.
  • the reaction mixture was stirred for 16 h. Then water was added, the phases were separated and the aqueous layer was extracted with dichloromethane. The combined organic layers were dried over sodium sulfate and concentrated.
  • the compound was dissolved in a mixture of acetone and/or dimethylsulfoxide and the wetting agent/emulsifier Wettol, which is based on ethoxylated alkylphenoles, in a ratio (volume) solvent- emulsifier of 99 to 1 to give a total volume of 5 ml. Subsequently, water was added to total volume of 100 ml.
  • Wettol which is based on ethoxylated alkylphenoles
  • This stock solution was then diluted with the described solvent-emulsifier-water mixture to the final concentration given in the table below.
  • Example 1- Preventative fungicidal control of Botrytis cinerea on leaves of green pepper
  • Young seedlings of green pepper were grown in pots to the 4 to 5 leaf stage. These plants were sprayed to run-off with previously described spray solution, containing the concentration of active ingredient or mixture mentioned in the table below. Seven days later the plants were inoculated with an aqueous DOB solution (or a DOB solution containing 10 percent glycerine), containing the spore suspension of Botrytis cinerea. Then the plants were immediately transferred to a humid chamber. After 5 days at 22 to 24 C and a saturated relative humidity, the extent of fungal attack on the leaves was visually assessed as % diseased leaf area.
  • aqueous DOB solution or a DOB solution containing 10 percent glycerine

Abstract

La présente invention concerne l'utilisation de composés de formule I, dans laquelle les variables sont telles que définies dans la description et les revendications. L'invention concerne en outre les composés I et une composition pour des composés de formule I.
PCT/EP2020/064579 2019-06-06 2020-05-26 Nouveaux carboxamides de pyridine carbocycliques WO2020244970A1 (fr)

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Citations (154)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3296272A (en) 1965-04-01 1967-01-03 Dow Chemical Co Sulfinyl- and sulfonylpyridines
US3325503A (en) 1965-02-18 1967-06-13 Diamond Alkali Co Polychloro derivatives of mono- and dicyano pyridines and a method for their preparation
EP0141317A2 (fr) 1983-10-21 1985-05-15 BASF Aktiengesellschaft 7-Amino-azolo[1,5-a]pyrimidines et fongicides les contenant
EP0152031A2 (fr) 1984-02-03 1985-08-21 Shionogi & Co., Ltd. Dérivés azolyl cycloalkanols et fongicides agricoles
EP0226917A1 (fr) 1985-12-20 1987-07-01 BASF Aktiengesellschaft Esters acryliques et fongicides contenant ces composés
EP0243970A1 (fr) 1986-05-02 1987-11-04 Stauffer Chemical Company Imidates de pyridyle fongicides
EP0256503A2 (fr) 1986-08-12 1988-02-24 Mitsubishi Kasei Corporation Dérivés de pyridinecarboxamide et leur utilisation comme fongicides
EP0428941A1 (fr) 1989-11-10 1991-05-29 Agro-Kanesho Co., Ltd. Dérivés de l'hexahydrotriazine et insecticides
EP0532022A1 (fr) 1991-09-13 1993-03-17 Ube Industries, Ltd. Composés acryliques, procédé pour leur préparation et fongicides les contenant
WO1994001546A1 (fr) 1992-07-01 1994-01-20 Cornell Research Foundation, Inc. Inducteur de la reponse hypersensible chez des plantes
EP0816331A1 (fr) * 1996-06-28 1998-01-07 Rohm And Haas Company Composés N-acétonylbenzamides ayant une activité fongicide
DE19650197A1 (de) 1996-12-04 1998-06-10 Bayer Ag 3-Thiocarbamoylpyrazol-Derivate
WO1998044140A1 (fr) 1997-04-03 1998-10-08 Dekalb Genetics Corporation Lignees de mais resistantes aux glyphosates
WO1998046608A1 (fr) 1997-04-14 1998-10-22 American Cyanamid Company Trifluoromethylalkylamino-triazolopyrimidines fongicides
WO1999014187A1 (fr) 1997-09-18 1999-03-25 Basf Aktiengesellschaft Derives de benzamidoxime, produits intermediaires et procedes pour les preparer et les utiliser comme fongicides
WO1999024413A2 (fr) 1997-11-12 1999-05-20 Bayer Aktiengesellschaft Amides d'acide isothiazol carboxylique et leur utilisation pour la protection de plantes
WO1999027783A1 (fr) 1997-12-04 1999-06-10 Dow Agrosciences Llc Compositions fongicides, procedes correspondants, composes et procedes concourant a leur elaboration
EP0943602A1 (fr) 1998-03-16 1999-09-22 Rohm And Haas Company Procédé amélioré pour la préparation de chloroalkynes et d'alkynylamines
WO2000026356A1 (fr) 1998-11-03 2000-05-11 Aventis Cropscience N. V. Riz tolerant au glufosinate
WO2000026345A1 (fr) 1998-11-03 2000-05-11 Aventis Cropscience N.V. Riz tolerant au glufosinate
WO2000029404A1 (fr) 1998-11-17 2000-05-25 Kumiai Chemical Industry Co., Ltd. Derives de pyrimidinylbenzimidazole et de triazinylbenzimidazole et bactericides agricoles/horticoles
WO2000046148A1 (fr) 1999-02-02 2000-08-10 Sintokogio, Ltd. Gel de silice a photocatalyseur fortement concentre a base d'oxyde de titane et procede de fabrication correspondant
EP1028125A1 (fr) 1998-11-30 2000-08-16 Isagro Ricerca S.r.l. Dipeptides ayant une activité fungizide et leur utilisation agronomique
EP1035122A1 (fr) 1999-03-11 2000-09-13 Rohm And Haas Company Isoxazolidines substituées par des hétérocycles et leur utilisation comme fongicides
WO2000065913A1 (fr) 1999-04-28 2000-11-09 Takeda Chemical Industries, Ltd. Derives de sulfamide
WO2001031042A2 (fr) 1999-10-29 2001-05-03 Aventis Cropscience N.V. Plantes brassica male sterile et procedes de production de ces plantes
WO2001041558A1 (fr) 1999-12-08 2001-06-14 Aventis Cropscience N.V. Colza oleagineux d'hiver hybrides et son procede de production
DE10021412A1 (de) 1999-12-13 2001-06-21 Bayer Ag Fungizide Wirkstoffkombinationen
WO2001054501A2 (fr) 2000-01-25 2001-08-02 Syngenta Participations Ag Composition herbicide
EP1122244A1 (fr) 2000-02-04 2001-08-08 Sumitomo Chemical Company, Limited Composés d'uracile et leur usage
WO2001056358A2 (fr) 2000-01-28 2001-08-09 Rohm And Haas Company Pesticides dotes de proprietes accrues
CN1309897A (zh) 2000-02-24 2001-08-29 沈阳化工研究院 不饱和肟醚类杀菌剂
WO2002022583A2 (fr) 2000-09-18 2002-03-21 E. I. Du Pont De Nemours And Company Pyridinyl-amides et pyridinyl-imides utilisés comme fongicides
EP1201648A1 (fr) 1999-08-05 2002-05-02 Kumiai Chemical Industry Co., Ltd. Derives de carbamate et bactericides destines a l'agriculture et a l'horticulture
WO2002034946A2 (fr) 2000-10-25 2002-05-02 Monsanto Technology Llc Mecanisme biochimique de plant de coton pv-ghgt07(1445), compositions et techniques de detection de celui-ci
WO2002036831A2 (fr) 2000-10-30 2002-05-10 Monsanto Technology Llc Colza canola pv-bngt(rt73), compositions et procedes de detection correspondants
WO2002040431A2 (fr) 2000-11-17 2002-05-23 Dow Agrosciences Llc Composes presentant une activite fongicide et leurs procedes de preparation et d'utilisation
US20020102582A1 (en) 2000-09-13 2002-08-01 Levine Elaine B. Corn event MON810 and compositions and methods for detection thereof
JP2002316902A (ja) 2001-04-20 2002-10-31 Sumitomo Chem Co Ltd 植物病害防除剤組成物
WO2002100163A2 (fr) 2001-06-11 2002-12-19 Monsanto Technology Llc Evenement mon15985 du coton et compositions et procedes servant a sa detection
WO2003010149A1 (fr) 2001-07-25 2003-02-06 Bayer Cropscience Ag Carboxanilides de pyrazolyle utilises comme fongicides
WO2003011853A1 (fr) 2001-07-30 2003-02-13 Dow Agrosciences Llc 6-aryl-4-aminopicolinates et leur utilisation comme herbicides
WO2003013224A2 (fr) 2001-08-06 2003-02-20 Bayer Bioscience N.V. Cotonniers avec tolerance aux herbicides et procedes de production et d'identification de ces cotonniers
WO2003014103A1 (fr) 2001-08-03 2003-02-20 Bayer Cropscience S.A. Derives de iodobenzopyran-4-one presentant une activite fongicide
WO2003016286A1 (fr) 2001-08-17 2003-02-27 Sankyo Agro Company, Limited Derive de 3-phenoxy-4-pyridazinol et composition herbicide le contenant
WO2003016303A1 (fr) 2001-08-20 2003-02-27 Dainippon Ink And Chemicals, Inc. Derive de tetrazoyle oxime et produit chimique agricole contenant ledit derive comme principe actif
US20030126634A1 (en) 1990-08-09 2003-07-03 Dekalb Genetics Corporation Methods and compositions for the increase of yield in plants
WO2003053145A1 (fr) 2001-12-21 2003-07-03 Nissan Chemical Industries, Ltd. Composition bactericide
WO2003061388A1 (fr) 2002-01-18 2003-07-31 Sumitomo Chemical Takeda Agro Company, Limited Compose de sulfonyluree heterocyclique fusionne, herbicide contenant ce compose et procede de controle de plantes nuisibles au moyen de cet herbicide
WO2003064572A1 (fr) 2002-01-31 2003-08-07 Exxonmobil Research And Engineering Company Compositions d'huile lubrifiante a proprietes de reduction du frottement ameliorees
WO2003066609A1 (fr) 2002-02-04 2003-08-14 Bayer Cropscience Aktiengesellschaft Thiazolylcarboxanilides disubstitues et leur utilisation comme microbicides
WO2003074491A1 (fr) 2002-03-05 2003-09-12 Syngenta Participations Ag O-cyclopropyle-carboxanilides et leur utilisation comme fongicides
CN1456054A (zh) 2003-03-25 2003-11-19 浙江省化工研究院 甲氧基丙烯酸甲酯类化合物杀菌剂
WO2004011601A2 (fr) 2002-07-29 2004-02-05 Monsanto Technology, Llc Mais pv-zmir13 designe mon863, composition et procedes de detection
WO2004039986A1 (fr) 2002-10-29 2004-05-13 Syngenta Participations Ag Coton insecticide cot102
WO2004049804A2 (fr) 2002-11-29 2004-06-17 Syngenta Participations Ag Combinaisons fongicides pour proteger des cultures
WO2004072235A2 (fr) 2003-02-12 2004-08-26 Monsanto Technology Llc Evenement mon 88913 de plant de coton et procedes de detection correspondants
WO2004074492A1 (fr) 2003-02-20 2004-09-02 Kws Saat Ag Betteraves sucrieres tolerant le glyphosate
WO2004083193A1 (fr) 2003-03-17 2004-09-30 Sumitomo Chemical Company, Limited Compose amide et composition bactericide contenant ledit compose
WO2004099447A2 (fr) 2003-05-02 2004-11-18 Dow Agrosciences Llc Mais tc1507 et procedes de detection de celui-ci
WO2005059103A2 (fr) 2003-12-15 2005-06-30 Monsanto Technology Llc Plant de mais mon88017, compositions et procedes de detection associes
WO2005061720A2 (fr) 2003-12-11 2005-07-07 Monsanto Technology Llc Compositions de mais a haute teneur en lysine et methodes de detection correspondantes
WO2005063721A1 (fr) 2003-12-19 2005-07-14 E.I. Dupont De Nemours And Company Pyrimidines herbicides
WO2005087772A1 (fr) 2004-03-10 2005-09-22 Basf Aktiengesellschaft 5,6-dialkyl-7-amino-triazolopyrimidines, procedes pour leur production, leur utilisation pour lutter contre des champignons nuisibles, ainsi qu'agents les contenant
WO2005087773A1 (fr) 2004-03-10 2005-09-22 Basf Aktiengesellschaft 5,6-dialkyl-7-amino-triazolopyrimidines, procedes pour leur production, leur utilisation pour lutter contre des champignons nuisibles, ainsi qu'agents les contenant
WO2005103266A1 (fr) 2004-03-26 2005-11-03 Dow Agrosciences Llc Lignees de coton transgeniques cry1f et cry1ac et leur identification specifique a l'evenement
WO2005103301A2 (fr) 2004-03-25 2005-11-03 Syngenta Participations Ag Mais mir604
WO2005120234A2 (fr) 2004-06-03 2005-12-22 E.I. Dupont De Nemours And Company Melanges fongicides de composes d'amidinylphenyle
WO2005123689A1 (fr) 2004-06-18 2005-12-29 Basf Aktiengesellschaft 1-methyl-3-trifluoromethyl-pyrazol-4-acide carboxylique-(ortho-phenyl)-anilides et leur utilisation comme fongicides
WO2005123690A1 (fr) 2004-06-18 2005-12-29 Basf Aktiengesellschaft (ortho-phenyl)-anilides d'acide 1-methyl-3-difluormethyl-pyrazol-4-carboxylique et leur utilisation comme fongicides
WO2006015866A1 (fr) 2004-08-12 2006-02-16 Syngenta Participations Ag Procédé servant à protéger des plantes utiles ou une matière de propagation de plante
WO2006039376A2 (fr) 2004-09-29 2006-04-13 Pioneer Hi-Bred International, Inc. Evenement de mais das-59122-7, et procedes de detection correspondants
WO2006087343A1 (fr) 2005-02-16 2006-08-24 Basf Aktiengesellschaft Anilides d'acide carboxylique pyrazole, procedes de production associes et agents les contenant pour la lutte antifongique
WO2006087325A1 (fr) 2005-02-16 2006-08-24 Basf Aktiengesellschaft 5-alkoxyalkyl-6-alkyl-7-amino-azolopyrimidines, procede de fabrication de ces composes, utilisation dans la lutte contre des champignons parasites et agents les contenant
DE102005009458A1 (de) 2005-03-02 2006-09-07 Bayer Cropscience Ag Pyrazolylcarboxanilide
WO2006098952A2 (fr) 2005-03-16 2006-09-21 Syngenta Participations Ag Mais 3272 et procedes pour le detecter
WO2006108675A2 (fr) 2005-04-11 2006-10-19 Bayer Bioscience N.V. Evenement elite a5547-127 et procedes et trousses pour l'identification d'un tel evenement dans des echantillons biologiques
WO2006108674A2 (fr) 2005-04-08 2006-10-19 Bayer Bioscience N.V. Evenement elite a2704-12 et procedes et trousses permettant d'identifier cet evenement dans des prelevements biologiques
WO2006128573A2 (fr) 2005-06-02 2006-12-07 Syngenta Participations Ag Coton insecticide ce43-67b
WO2006130436A2 (fr) 2005-05-27 2006-12-07 Monsanto Technology Llc Evenement de soja mon89788 et procedes de detection de celui-ci
WO2007006670A1 (fr) 2005-07-07 2007-01-18 Basf Aktiengesellschaft Composes de n-thio-anthranilamide et utilisations comme pesticides
CN1907024A (zh) 2005-08-03 2007-02-07 浙江化工科技集团有限公司 取代甲氧基丙烯酸甲酯类化合物杀菌剂
WO2007017186A1 (fr) 2005-08-08 2007-02-15 Bayer Bioscience N.V. Cotonniers tolerants aux herbicides et leurs procedes d'identification
WO2007082098A2 (fr) 2006-01-13 2007-07-19 Dow Agrosciences Llc 6-(poly-aryl substituté)-4-aminopicolinates et utilisations de ceux-ci comme herbicides
WO2007090624A2 (fr) 2006-02-09 2007-08-16 Syngenta Participations Ag Procede de protection d'une matiere de propagation vegetale, d'un vegetal et/ou d'un organisme vegetal
WO2007129454A1 (fr) 2006-05-08 2007-11-15 Kumiai Chemical Industry Co., Ltd. Derive 1,2-benzisothiazole et agent luttant contre une maladie de plante agricole ou horticole
WO2007140256A1 (fr) 2006-05-26 2007-12-06 Monsanto Technology, Llc Plant et semence de maïs correspondant au produit transgénique mon89034, procédés de détection et utilisation associés
WO2007142840A2 (fr) 2006-06-03 2007-12-13 Syngenta Participations Ag Événement de transformation de maïs mir162
US20070292854A1 (en) 2000-06-22 2007-12-20 Behr Carl F Corn event PV-ZMGT32(nk603) and compositions and methods for detection thereof
WO2008002872A2 (fr) 2006-06-28 2008-01-03 Pioneer Hi-Bred International, Inc. Événement de soja 3560.4.3.5 et compositions et procedes d'identification et/ou de détection de celui-ci
WO2008013622A2 (fr) 2006-07-27 2008-01-31 E. I. Du Pont De Nemours And Company Amides azocycliques fongicides
WO2008054747A2 (fr) 2006-10-31 2008-05-08 E. I. Du Pont De Nemours And Company Événement de soja dp-305423-1, leurs compositions et leurs procédés d'identification et/ou de détection
WO2008081017A1 (fr) * 2007-01-03 2008-07-10 Bayer Cropscience Ag Nouveaux dérivés de n-alkynylcarboxamide
WO2008112019A2 (fr) 2006-10-30 2008-09-18 Pioneer Hi-Bred International, Inc. Evènement dp-098140-6 du maïs et compositions et procédés pour son identification et/ou sa détection
WO2008122406A1 (fr) 2007-04-05 2008-10-16 Bayer Bioscience N.V. Plants de coton résistant aux insectes et leurs procédés d'identification
WO2008151780A1 (fr) 2007-06-11 2008-12-18 Bayer Bioscience N.V. Cotonniers résistant aux insectes comprenant un événement élite ee-gh6 et leurs procédés d'identification
US20080319080A1 (en) * 2005-10-27 2008-12-25 Takashi Komori Amide Compounds and Their Use
WO2009064652A1 (fr) 2007-11-15 2009-05-22 Monsanto Technology Llc Plante et graine de soja correspondant à l'événement transgénique mon87701 et procédés pour les détecter
WO2009090181A2 (fr) 2008-01-15 2009-07-23 Bayer Cropscience Sa Composition pesticide comprenant un dérivé de tétrazolyloxime et une substance active fongicide ou insecticide
WO2009094442A2 (fr) 2008-01-22 2009-07-30 Dow Agrosciences Llc Dérivés de 5-fluoropyrimidine
WO2009102873A1 (fr) 2008-02-15 2009-08-20 Monsanto Technology Llc Plante de soja et graine correspondant à l’évènement transgénique mon87769 et leurs procédés de détection
WO2009103049A2 (fr) 2008-02-14 2009-08-20 Pioneer Hi-Bred International, Inc. Evénement spt flanquant l'adn génomique végétal et procédés d'identification de l'événement spt
WO2009111263A1 (fr) 2008-02-29 2009-09-11 Monsanto Technology Llc Plant de maïs correspondant au produit transgénique mon87460 et compositions et procédés de détection associés
WO2010037016A1 (fr) 2008-09-29 2010-04-01 Monsanto Technology Llc Événement transgénique de soja t mon87705 et procédés pour la détection de celui-ci
WO2010069882A1 (fr) 2008-12-17 2010-06-24 Syngenta Participations Ag Dérivés d'isoxazole en tant que fongicides
WO2010077816A1 (fr) 2008-12-16 2010-07-08 Syngenta Participations Ag Evénement transgénique du maïs 5307
WO2010080829A1 (fr) 2009-01-07 2010-07-15 Basf Agrochemical Products B.V. Évènement de soja 127 et procédés apparentés
WO2010139271A1 (fr) 2009-06-05 2010-12-09 中国中化股份有限公司 Composés ester phénylacrylique de type e contenant un groupe anilinopyrimidine substitué et leurs utilisations
WO2011022469A2 (fr) 2009-08-19 2011-02-24 Dow Agrosciences Llc Événement das-40278-9 d'aad-1, lignées transgéniques de maïs connexes et identification spécifique d'événement de celui-ci
WO2011028657A1 (fr) 2009-09-01 2011-03-10 Dow Agrosciences Llc Compositions fongicides synergiques contenant un dérivé de 5-fluoropyrimidine pour la lutte contre les champignons dans des céréales
WO2011034704A1 (fr) 2009-09-17 2011-03-24 Monsanto Technology Llc Variété transgénique mon 87708 du soja et ses méthodes d'utilisation
WO2011062904A1 (fr) 2009-11-23 2011-05-26 Monsanto Technology Llc Événement du maïs transgénique mon 87427 et échelle de développement relative
WO2011066384A1 (fr) 2009-11-24 2011-06-03 Dow Agrosciences Llc Événement 416 de la transformation aad-12, lignées de soja transgéniques associées, et leur identification spécifique à l'événement
WO2011077514A1 (fr) 2009-12-22 2011-06-30 三井化学アグロ株式会社 Composition permettant de lutter contre des maladies végétales et procédé de lutte contre des maladies végétales par application de la composition
WO2011081174A1 (fr) 2010-01-04 2011-07-07 日本曹達株式会社 Compose heterocyclique contenant de l'azote et germicide agricole/horticole
WO2011084621A1 (fr) 2009-12-17 2011-07-14 Pioneer Hi-Bred International, Inc. Evénement de transformation dp-004114-3 du maïs et son procédé de détection
WO2011135827A1 (fr) 2010-04-27 2011-11-03 Sumitomo Chemical Company, Limited Composition pesticide et utilisation associée
WO2011135833A1 (fr) 2010-04-28 2011-11-03 Sumitomo Chemical Company, Limited Composition phytosanitaire et utilisation associée
WO2011153186A1 (fr) 2010-06-04 2011-12-08 Monsanto Technology Llc Evénement mon 88032 d'une plante transgénique du genre brassica et ses procédés d'utilisation
WO2012051199A2 (fr) 2010-10-12 2012-04-19 Monsanto Technology Llc Plante et semence de soja correspondant à l'événement transgénique mon87712 et procédé pour les détecter
WO2012082548A2 (fr) 2010-12-15 2012-06-21 Syngenta Participations Ag Soja comprenant le mécanisme de transformation syht04r, et compositions et procédés de détection de ce mécanisme
WO2012084812A1 (fr) 2010-12-20 2012-06-28 Isagro Ricerca S.R.L. Amides d'aminoindanes présentant une forte activité fongicide et leurs compositions phytosanitaires
WO2012134808A1 (fr) 2011-03-30 2012-10-04 Monsanto Technology Llc Événement transgénique mon 88701 du coton et ses procédés d'utilisation
WO2012165511A1 (fr) 2011-05-31 2012-12-06 クミアイ化学工業株式会社 Procédé de lutte contre des maladies dans une plante de riz
WO2012168188A1 (fr) 2011-06-07 2012-12-13 Bayer Intellectual Property Gmbh Combinaisons de composés actifs
WO2013003558A1 (fr) 2011-06-30 2013-01-03 Monsanto Technology Llc Plante et graine de luzerne correspondant à l'événement transgénique kk 179-2 et procédés pour la détection de celui-ci
WO2013007767A1 (fr) 2011-07-13 2013-01-17 Basf Se Composés fongicides 2-[2-halogenalkyl-4-(phenoxy)-phenyl]-1-[1,2,4]triazol-1-yl-ethanol substitués
WO2013010862A1 (fr) 2011-07-15 2013-01-24 Basf Se Composés fongicides de 2-[2-chloro-4-(4-chloro-phénoxy)-phényl]-1-[1,2,4]triazol-1-yl-éthanol substitué par alkyle
WO2013016516A1 (fr) 2011-07-26 2013-01-31 Dow Agrosciences Llc Evénement combiné de sélection résistant aux insectes et tolérant à un herbicide d'un événement de soja pdab9582.814.19.1 et pdab4468.04.16.1
WO2013024009A1 (fr) 2011-08-12 2013-02-21 Basf Se Composés n-thio-anthranilamides et leur utilisation comme pesticides
WO2013024010A1 (fr) 2011-08-12 2013-02-21 Basf Se Composés n-thio-anthranilamides et leur utilisation comme pesticides
WO2013047441A1 (fr) 2011-09-26 2013-04-04 日本曹達株式会社 Composition bactéricide pour l'agriculture et l'horticulture
WO2013047749A1 (fr) 2011-09-29 2013-04-04 三井化学アグロ株式会社 Procédé de fabrication de dérivé de 4,4-difluoro-3,4-dihydroisoquinoléine
WO2013092224A1 (fr) 2011-12-21 2013-06-27 Basf Se Utilisation de composés de type strobilurine pour combattre des champignons phytopathogènes résistants aux inhibiteurs du site qo
WO2013112527A1 (fr) 2012-01-23 2013-08-01 Dow Agrosciences Llc Coton résistant aux herbicides évènement pdab4468.19.10.3
WO2013116251A2 (fr) 2012-02-01 2013-08-08 E. I. Du Pont De Nemours And Company Mélanges de pyrazole fongicides
WO2013127704A1 (fr) 2012-02-27 2013-09-06 Bayer Intellectual Property Gmbh Associations de composés actifs contenant une thiazoylisoxazoline et un fongicide
WO2013162072A1 (fr) 2012-04-27 2013-10-31 Sumitomo Chemical Company, Limited Composés de tétrazolinone et leur utilisation en tant que pesticides
CN103387541A (zh) 2012-05-10 2013-11-13 中国中化股份有限公司 一种取代吡唑醚类化合物的制备方法
WO2013169923A2 (fr) 2012-05-08 2013-11-14 Monsanto Technology Llc Événement de maïs mon 87411
WO2014060177A1 (fr) 2012-10-16 2014-04-24 Syngenta Participations Ag Compositions fongicides
WO2014116854A1 (fr) 2013-01-25 2014-07-31 Pioneer Hi-Bred International, Inc. Événement de maïs dp-033121-3 et ses procédés de détection
WO2014178910A1 (fr) 2013-05-02 2014-11-06 J.R. Simplot Company Cultivar de pomme de terre e12
WO2014201235A2 (fr) 2013-06-14 2014-12-18 Monsanto Technology Llc Événement transgénique de soja mon87751 et procédés de détection et d'utilisation de celui-ci
WO2015053998A1 (fr) 2013-10-09 2015-04-16 Monsanto Technology Llc Événement de maïs transgénique mon87403 et procédés pour la détection de celui-ci
EP2865265A1 (fr) 2014-02-13 2015-04-29 Bayer CropScience AG Combinaisons de composés actifs comprenant des composés phénylamidine et agents de lutte biologique
WO2015065922A1 (fr) 2013-10-28 2015-05-07 Dexcom, Inc. Dispositifs utilisés en relation avec une surveillance continue de substances à analyser pour fournir une ou plusieurs notifications à un utilisateur, et procédés associés
JP2015089883A (ja) 2013-11-06 2015-05-11 アグロカネショウ株式会社 ２−アミノニコチン酸ベンジルエステル誘導体およびこれを有効成分とする殺菌剤
JP2015120675A (ja) 2013-12-25 2015-07-02 アグロカネショウ株式会社 ６−置換ニコチン酸エステル誘導体およびこれを有効成分とする殺菌剤
WO2015119246A1 (fr) 2014-02-07 2015-08-13 日産化学工業株式会社 Composition bactéricide ou de stérilisation et méthode de lutte contre les maladies
WO2015142571A1 (fr) 2014-03-20 2015-09-24 Monsanto Technology Llc Événement transgénique de maïs mon 87419 et méthodes d'utilisation de celui-ci
WO2016183445A1 (fr) 2015-05-14 2016-11-17 J.R. Simplot Company Cultivar de pomme de terre v11
WO2017062825A1 (fr) 2015-10-08 2017-04-13 J.R. Simplot Company Cultivar de pomme de terre y9
WO2017062831A1 (fr) 2015-10-08 2017-04-13 J.R. Simplot Company Cultivar de pomme de terre x17

Patent Citations (158)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3325503A (en) 1965-02-18 1967-06-13 Diamond Alkali Co Polychloro derivatives of mono- and dicyano pyridines and a method for their preparation
US3296272A (en) 1965-04-01 1967-01-03 Dow Chemical Co Sulfinyl- and sulfonylpyridines
EP0141317A2 (fr) 1983-10-21 1985-05-15 BASF Aktiengesellschaft 7-Amino-azolo[1,5-a]pyrimidines et fongicides les contenant
EP0152031A2 (fr) 1984-02-03 1985-08-21 Shionogi & Co., Ltd. Dérivés azolyl cycloalkanols et fongicides agricoles
EP0226917A1 (fr) 1985-12-20 1987-07-01 BASF Aktiengesellschaft Esters acryliques et fongicides contenant ces composés
EP0243970A1 (fr) 1986-05-02 1987-11-04 Stauffer Chemical Company Imidates de pyridyle fongicides
EP0256503A2 (fr) 1986-08-12 1988-02-24 Mitsubishi Kasei Corporation Dérivés de pyridinecarboxamide et leur utilisation comme fongicides
EP0428941A1 (fr) 1989-11-10 1991-05-29 Agro-Kanesho Co., Ltd. Dérivés de l'hexahydrotriazine et insecticides
US20030126634A1 (en) 1990-08-09 2003-07-03 Dekalb Genetics Corporation Methods and compositions for the increase of yield in plants
EP0532022A1 (fr) 1991-09-13 1993-03-17 Ube Industries, Ltd. Composés acryliques, procédé pour leur préparation et fongicides les contenant
WO1994001546A1 (fr) 1992-07-01 1994-01-20 Cornell Research Foundation, Inc. Inducteur de la reponse hypersensible chez des plantes
EP0816331A1 (fr) * 1996-06-28 1998-01-07 Rohm And Haas Company Composés N-acétonylbenzamides ayant une activité fongicide
DE19650197A1 (de) 1996-12-04 1998-06-10 Bayer Ag 3-Thiocarbamoylpyrazol-Derivate
WO1998044140A1 (fr) 1997-04-03 1998-10-08 Dekalb Genetics Corporation Lignees de mais resistantes aux glyphosates
WO1998046608A1 (fr) 1997-04-14 1998-10-22 American Cyanamid Company Trifluoromethylalkylamino-triazolopyrimidines fongicides
WO1999014187A1 (fr) 1997-09-18 1999-03-25 Basf Aktiengesellschaft Derives de benzamidoxime, produits intermediaires et procedes pour les preparer et les utiliser comme fongicides
WO1999024413A2 (fr) 1997-11-12 1999-05-20 Bayer Aktiengesellschaft Amides d'acide isothiazol carboxylique et leur utilisation pour la protection de plantes
WO1999027783A1 (fr) 1997-12-04 1999-06-10 Dow Agrosciences Llc Compositions fongicides, procedes correspondants, composes et procedes concourant a leur elaboration
EP0943602A1 (fr) 1998-03-16 1999-09-22 Rohm And Haas Company Procédé amélioré pour la préparation de chloroalkynes et d'alkynylamines
WO2000026356A1 (fr) 1998-11-03 2000-05-11 Aventis Cropscience N. V. Riz tolerant au glufosinate
WO2000026345A1 (fr) 1998-11-03 2000-05-11 Aventis Cropscience N.V. Riz tolerant au glufosinate
WO2000029404A1 (fr) 1998-11-17 2000-05-25 Kumiai Chemical Industry Co., Ltd. Derives de pyrimidinylbenzimidazole et de triazinylbenzimidazole et bactericides agricoles/horticoles
EP1028125A1 (fr) 1998-11-30 2000-08-16 Isagro Ricerca S.r.l. Dipeptides ayant une activité fungizide et leur utilisation agronomique
WO2000046148A1 (fr) 1999-02-02 2000-08-10 Sintokogio, Ltd. Gel de silice a photocatalyseur fortement concentre a base d'oxyde de titane et procede de fabrication correspondant
EP1035122A1 (fr) 1999-03-11 2000-09-13 Rohm And Haas Company Isoxazolidines substituées par des hétérocycles et leur utilisation comme fongicides
WO2000065913A1 (fr) 1999-04-28 2000-11-09 Takeda Chemical Industries, Ltd. Derives de sulfamide
EP1201648A1 (fr) 1999-08-05 2002-05-02 Kumiai Chemical Industry Co., Ltd. Derives de carbamate et bactericides destines a l'agriculture et a l'horticulture
WO2001031042A2 (fr) 1999-10-29 2001-05-03 Aventis Cropscience N.V. Plantes brassica male sterile et procedes de production de ces plantes
WO2001041558A1 (fr) 1999-12-08 2001-06-14 Aventis Cropscience N.V. Colza oleagineux d'hiver hybrides et son procede de production
DE10021412A1 (de) 1999-12-13 2001-06-21 Bayer Ag Fungizide Wirkstoffkombinationen
WO2001054501A2 (fr) 2000-01-25 2001-08-02 Syngenta Participations Ag Composition herbicide
WO2001056358A2 (fr) 2000-01-28 2001-08-09 Rohm And Haas Company Pesticides dotes de proprietes accrues
EP1122244A1 (fr) 2000-02-04 2001-08-08 Sumitomo Chemical Company, Limited Composés d'uracile et leur usage
CN1309897A (zh) 2000-02-24 2001-08-29 沈阳化工研究院 不饱和肟醚类杀菌剂
US20070292854A1 (en) 2000-06-22 2007-12-20 Behr Carl F Corn event PV-ZMGT32(nk603) and compositions and methods for detection thereof
US20020102582A1 (en) 2000-09-13 2002-08-01 Levine Elaine B. Corn event MON810 and compositions and methods for detection thereof
WO2002022583A2 (fr) 2000-09-18 2002-03-21 E. I. Du Pont De Nemours And Company Pyridinyl-amides et pyridinyl-imides utilisés comme fongicides
WO2002034946A2 (fr) 2000-10-25 2002-05-02 Monsanto Technology Llc Mecanisme biochimique de plant de coton pv-ghgt07(1445), compositions et techniques de detection de celui-ci
WO2002036831A2 (fr) 2000-10-30 2002-05-10 Monsanto Technology Llc Colza canola pv-bngt(rt73), compositions et procedes de detection correspondants
WO2002040431A2 (fr) 2000-11-17 2002-05-23 Dow Agrosciences Llc Composes presentant une activite fongicide et leurs procedes de preparation et d'utilisation
JP2002316902A (ja) 2001-04-20 2002-10-31 Sumitomo Chem Co Ltd 植物病害防除剤組成物
WO2002100163A2 (fr) 2001-06-11 2002-12-19 Monsanto Technology Llc Evenement mon15985 du coton et compositions et procedes servant a sa detection
WO2003010149A1 (fr) 2001-07-25 2003-02-06 Bayer Cropscience Ag Carboxanilides de pyrazolyle utilises comme fongicides
WO2003011853A1 (fr) 2001-07-30 2003-02-13 Dow Agrosciences Llc 6-aryl-4-aminopicolinates et leur utilisation comme herbicides
WO2003014103A1 (fr) 2001-08-03 2003-02-20 Bayer Cropscience S.A. Derives de iodobenzopyran-4-one presentant une activite fongicide
WO2003013224A2 (fr) 2001-08-06 2003-02-20 Bayer Bioscience N.V. Cotonniers avec tolerance aux herbicides et procedes de production et d'identification de ces cotonniers
WO2003016286A1 (fr) 2001-08-17 2003-02-27 Sankyo Agro Company, Limited Derive de 3-phenoxy-4-pyridazinol et composition herbicide le contenant
WO2003016303A1 (fr) 2001-08-20 2003-02-27 Dainippon Ink And Chemicals, Inc. Derive de tetrazoyle oxime et produit chimique agricole contenant ledit derive comme principe actif
WO2003053145A1 (fr) 2001-12-21 2003-07-03 Nissan Chemical Industries, Ltd. Composition bactericide
WO2003061388A1 (fr) 2002-01-18 2003-07-31 Sumitomo Chemical Takeda Agro Company, Limited Compose de sulfonyluree heterocyclique fusionne, herbicide contenant ce compose et procede de controle de plantes nuisibles au moyen de cet herbicide
WO2003064572A1 (fr) 2002-01-31 2003-08-07 Exxonmobil Research And Engineering Company Compositions d'huile lubrifiante a proprietes de reduction du frottement ameliorees
WO2003066609A1 (fr) 2002-02-04 2003-08-14 Bayer Cropscience Aktiengesellschaft Thiazolylcarboxanilides disubstitues et leur utilisation comme microbicides
WO2003074491A1 (fr) 2002-03-05 2003-09-12 Syngenta Participations Ag O-cyclopropyle-carboxanilides et leur utilisation comme fongicides
WO2004011601A2 (fr) 2002-07-29 2004-02-05 Monsanto Technology, Llc Mais pv-zmir13 designe mon863, composition et procedes de detection
WO2004039986A1 (fr) 2002-10-29 2004-05-13 Syngenta Participations Ag Coton insecticide cot102
WO2004049804A2 (fr) 2002-11-29 2004-06-17 Syngenta Participations Ag Combinaisons fongicides pour proteger des cultures
WO2004072235A2 (fr) 2003-02-12 2004-08-26 Monsanto Technology Llc Evenement mon 88913 de plant de coton et procedes de detection correspondants
WO2004074492A1 (fr) 2003-02-20 2004-09-02 Kws Saat Ag Betteraves sucrieres tolerant le glyphosate
WO2004083193A1 (fr) 2003-03-17 2004-09-30 Sumitomo Chemical Company, Limited Compose amide et composition bactericide contenant ledit compose
CN1456054A (zh) 2003-03-25 2003-11-19 浙江省化工研究院 甲氧基丙烯酸甲酯类化合物杀菌剂
WO2004099447A2 (fr) 2003-05-02 2004-11-18 Dow Agrosciences Llc Mais tc1507 et procedes de detection de celui-ci
WO2005061720A2 (fr) 2003-12-11 2005-07-07 Monsanto Technology Llc Compositions de mais a haute teneur en lysine et methodes de detection correspondantes
WO2005059103A2 (fr) 2003-12-15 2005-06-30 Monsanto Technology Llc Plant de mais mon88017, compositions et procedes de detection associes
WO2005063721A1 (fr) 2003-12-19 2005-07-14 E.I. Dupont De Nemours And Company Pyrimidines herbicides
WO2005087772A1 (fr) 2004-03-10 2005-09-22 Basf Aktiengesellschaft 5,6-dialkyl-7-amino-triazolopyrimidines, procedes pour leur production, leur utilisation pour lutter contre des champignons nuisibles, ainsi qu'agents les contenant
WO2005087773A1 (fr) 2004-03-10 2005-09-22 Basf Aktiengesellschaft 5,6-dialkyl-7-amino-triazolopyrimidines, procedes pour leur production, leur utilisation pour lutter contre des champignons nuisibles, ainsi qu'agents les contenant
WO2005103301A2 (fr) 2004-03-25 2005-11-03 Syngenta Participations Ag Mais mir604
WO2005103266A1 (fr) 2004-03-26 2005-11-03 Dow Agrosciences Llc Lignees de coton transgeniques cry1f et cry1ac et leur identification specifique a l'evenement
WO2005120234A2 (fr) 2004-06-03 2005-12-22 E.I. Dupont De Nemours And Company Melanges fongicides de composes d'amidinylphenyle
WO2005123690A1 (fr) 2004-06-18 2005-12-29 Basf Aktiengesellschaft (ortho-phenyl)-anilides d'acide 1-methyl-3-difluormethyl-pyrazol-4-carboxylique et leur utilisation comme fongicides
WO2005123689A1 (fr) 2004-06-18 2005-12-29 Basf Aktiengesellschaft 1-methyl-3-trifluoromethyl-pyrazol-4-acide carboxylique-(ortho-phenyl)-anilides et leur utilisation comme fongicides
WO2006015866A1 (fr) 2004-08-12 2006-02-16 Syngenta Participations Ag Procédé servant à protéger des plantes utiles ou une matière de propagation de plante
WO2006039376A2 (fr) 2004-09-29 2006-04-13 Pioneer Hi-Bred International, Inc. Evenement de mais das-59122-7, et procedes de detection correspondants
WO2006087343A1 (fr) 2005-02-16 2006-08-24 Basf Aktiengesellschaft Anilides d'acide carboxylique pyrazole, procedes de production associes et agents les contenant pour la lutte antifongique
WO2006087325A1 (fr) 2005-02-16 2006-08-24 Basf Aktiengesellschaft 5-alkoxyalkyl-6-alkyl-7-amino-azolopyrimidines, procede de fabrication de ces composes, utilisation dans la lutte contre des champignons parasites et agents les contenant
DE102005009458A1 (de) 2005-03-02 2006-09-07 Bayer Cropscience Ag Pyrazolylcarboxanilide
WO2006098952A2 (fr) 2005-03-16 2006-09-21 Syngenta Participations Ag Mais 3272 et procedes pour le detecter
WO2006108674A2 (fr) 2005-04-08 2006-10-19 Bayer Bioscience N.V. Evenement elite a2704-12 et procedes et trousses permettant d'identifier cet evenement dans des prelevements biologiques
WO2006108675A2 (fr) 2005-04-11 2006-10-19 Bayer Bioscience N.V. Evenement elite a5547-127 et procedes et trousses pour l'identification d'un tel evenement dans des echantillons biologiques
WO2006130436A2 (fr) 2005-05-27 2006-12-07 Monsanto Technology Llc Evenement de soja mon89788 et procedes de detection de celui-ci
WO2006128573A2 (fr) 2005-06-02 2006-12-07 Syngenta Participations Ag Coton insecticide ce43-67b
WO2007006670A1 (fr) 2005-07-07 2007-01-18 Basf Aktiengesellschaft Composes de n-thio-anthranilamide et utilisations comme pesticides
CN1907024A (zh) 2005-08-03 2007-02-07 浙江化工科技集团有限公司 取代甲氧基丙烯酸甲酯类化合物杀菌剂
WO2007017186A1 (fr) 2005-08-08 2007-02-15 Bayer Bioscience N.V. Cotonniers tolerants aux herbicides et leurs procedes d'identification
US20080319080A1 (en) * 2005-10-27 2008-12-25 Takashi Komori Amide Compounds and Their Use
WO2007082098A2 (fr) 2006-01-13 2007-07-19 Dow Agrosciences Llc 6-(poly-aryl substituté)-4-aminopicolinates et utilisations de ceux-ci comme herbicides
WO2007090624A2 (fr) 2006-02-09 2007-08-16 Syngenta Participations Ag Procede de protection d'une matiere de propagation vegetale, d'un vegetal et/ou d'un organisme vegetal
WO2007129454A1 (fr) 2006-05-08 2007-11-15 Kumiai Chemical Industry Co., Ltd. Derive 1,2-benzisothiazole et agent luttant contre une maladie de plante agricole ou horticole
WO2007140256A1 (fr) 2006-05-26 2007-12-06 Monsanto Technology, Llc Plant et semence de maïs correspondant au produit transgénique mon89034, procédés de détection et utilisation associés
WO2007142840A2 (fr) 2006-06-03 2007-12-13 Syngenta Participations Ag Événement de transformation de maïs mir162
WO2008002872A2 (fr) 2006-06-28 2008-01-03 Pioneer Hi-Bred International, Inc. Événement de soja 3560.4.3.5 et compositions et procedes d'identification et/ou de détection de celui-ci
WO2008013622A2 (fr) 2006-07-27 2008-01-31 E. I. Du Pont De Nemours And Company Amides azocycliques fongicides
WO2008112019A2 (fr) 2006-10-30 2008-09-18 Pioneer Hi-Bred International, Inc. Evènement dp-098140-6 du maïs et compositions et procédés pour son identification et/ou sa détection
WO2008054747A2 (fr) 2006-10-31 2008-05-08 E. I. Du Pont De Nemours And Company Événement de soja dp-305423-1, leurs compositions et leurs procédés d'identification et/ou de détection
WO2008081017A1 (fr) * 2007-01-03 2008-07-10 Bayer Cropscience Ag Nouveaux dérivés de n-alkynylcarboxamide
WO2008122406A1 (fr) 2007-04-05 2008-10-16 Bayer Bioscience N.V. Plants de coton résistant aux insectes et leurs procédés d'identification
WO2008151780A1 (fr) 2007-06-11 2008-12-18 Bayer Bioscience N.V. Cotonniers résistant aux insectes comprenant un événement élite ee-gh6 et leurs procédés d'identification
WO2009064652A1 (fr) 2007-11-15 2009-05-22 Monsanto Technology Llc Plante et graine de soja correspondant à l'événement transgénique mon87701 et procédés pour les détecter
WO2009090181A2 (fr) 2008-01-15 2009-07-23 Bayer Cropscience Sa Composition pesticide comprenant un dérivé de tétrazolyloxime et une substance active fongicide ou insecticide
WO2009094442A2 (fr) 2008-01-22 2009-07-30 Dow Agrosciences Llc Dérivés de 5-fluoropyrimidine
WO2009103049A2 (fr) 2008-02-14 2009-08-20 Pioneer Hi-Bred International, Inc. Evénement spt flanquant l'adn génomique végétal et procédés d'identification de l'événement spt
WO2009102873A1 (fr) 2008-02-15 2009-08-20 Monsanto Technology Llc Plante de soja et graine correspondant à l’évènement transgénique mon87769 et leurs procédés de détection
WO2009111263A1 (fr) 2008-02-29 2009-09-11 Monsanto Technology Llc Plant de maïs correspondant au produit transgénique mon87460 et compositions et procédés de détection associés
WO2010037016A1 (fr) 2008-09-29 2010-04-01 Monsanto Technology Llc Événement transgénique de soja t mon87705 et procédés pour la détection de celui-ci
WO2010077816A1 (fr) 2008-12-16 2010-07-08 Syngenta Participations Ag Evénement transgénique du maïs 5307
WO2010069882A1 (fr) 2008-12-17 2010-06-24 Syngenta Participations Ag Dérivés d'isoxazole en tant que fongicides
WO2010080829A1 (fr) 2009-01-07 2010-07-15 Basf Agrochemical Products B.V. Évènement de soja 127 et procédés apparentés
WO2010139271A1 (fr) 2009-06-05 2010-12-09 中国中化股份有限公司 Composés ester phénylacrylique de type e contenant un groupe anilinopyrimidine substitué et leurs utilisations
WO2011022469A2 (fr) 2009-08-19 2011-02-24 Dow Agrosciences Llc Événement das-40278-9 d'aad-1, lignées transgéniques de maïs connexes et identification spécifique d'événement de celui-ci
WO2011028657A1 (fr) 2009-09-01 2011-03-10 Dow Agrosciences Llc Compositions fongicides synergiques contenant un dérivé de 5-fluoropyrimidine pour la lutte contre les champignons dans des céréales
WO2011034704A1 (fr) 2009-09-17 2011-03-24 Monsanto Technology Llc Variété transgénique mon 87708 du soja et ses méthodes d'utilisation
WO2011062904A1 (fr) 2009-11-23 2011-05-26 Monsanto Technology Llc Événement du maïs transgénique mon 87427 et échelle de développement relative
WO2011066384A1 (fr) 2009-11-24 2011-06-03 Dow Agrosciences Llc Événement 416 de la transformation aad-12, lignées de soja transgéniques associées, et leur identification spécifique à l'événement
WO2011084621A1 (fr) 2009-12-17 2011-07-14 Pioneer Hi-Bred International, Inc. Evénement de transformation dp-004114-3 du maïs et son procédé de détection
WO2011077514A1 (fr) 2009-12-22 2011-06-30 三井化学アグロ株式会社 Composition permettant de lutter contre des maladies végétales et procédé de lutte contre des maladies végétales par application de la composition
WO2011081174A1 (fr) 2010-01-04 2011-07-07 日本曹達株式会社 Compose heterocyclique contenant de l'azote et germicide agricole/horticole
WO2011135827A1 (fr) 2010-04-27 2011-11-03 Sumitomo Chemical Company, Limited Composition pesticide et utilisation associée
WO2011135833A1 (fr) 2010-04-28 2011-11-03 Sumitomo Chemical Company, Limited Composition phytosanitaire et utilisation associée
WO2011153186A1 (fr) 2010-06-04 2011-12-08 Monsanto Technology Llc Evénement mon 88032 d'une plante transgénique du genre brassica et ses procédés d'utilisation
WO2012051199A2 (fr) 2010-10-12 2012-04-19 Monsanto Technology Llc Plante et semence de soja correspondant à l'événement transgénique mon87712 et procédé pour les détecter
WO2012082548A2 (fr) 2010-12-15 2012-06-21 Syngenta Participations Ag Soja comprenant le mécanisme de transformation syht04r, et compositions et procédés de détection de ce mécanisme
WO2012084812A1 (fr) 2010-12-20 2012-06-28 Isagro Ricerca S.R.L. Amides d'aminoindanes présentant une forte activité fongicide et leurs compositions phytosanitaires
WO2012134808A1 (fr) 2011-03-30 2012-10-04 Monsanto Technology Llc Événement transgénique mon 88701 du coton et ses procédés d'utilisation
WO2012165511A1 (fr) 2011-05-31 2012-12-06 クミアイ化学工業株式会社 Procédé de lutte contre des maladies dans une plante de riz
WO2012168188A1 (fr) 2011-06-07 2012-12-13 Bayer Intellectual Property Gmbh Combinaisons de composés actifs
WO2013003558A1 (fr) 2011-06-30 2013-01-03 Monsanto Technology Llc Plante et graine de luzerne correspondant à l'événement transgénique kk 179-2 et procédés pour la détection de celui-ci
WO2013007767A1 (fr) 2011-07-13 2013-01-17 Basf Se Composés fongicides 2-[2-halogenalkyl-4-(phenoxy)-phenyl]-1-[1,2,4]triazol-1-yl-ethanol substitués
WO2013010862A1 (fr) 2011-07-15 2013-01-24 Basf Se Composés fongicides de 2-[2-chloro-4-(4-chloro-phénoxy)-phényl]-1-[1,2,4]triazol-1-yl-éthanol substitué par alkyle
WO2013016516A1 (fr) 2011-07-26 2013-01-31 Dow Agrosciences Llc Evénement combiné de sélection résistant aux insectes et tolérant à un herbicide d'un événement de soja pdab9582.814.19.1 et pdab4468.04.16.1
WO2013016527A1 (fr) 2011-07-26 2013-01-31 Dow Agrosciences Llc Evénement de soja 9582.814.19.1 résistant aux insectes et tolérant aux herbicides
WO2013024009A1 (fr) 2011-08-12 2013-02-21 Basf Se Composés n-thio-anthranilamides et leur utilisation comme pesticides
WO2013024010A1 (fr) 2011-08-12 2013-02-21 Basf Se Composés n-thio-anthranilamides et leur utilisation comme pesticides
WO2013047441A1 (fr) 2011-09-26 2013-04-04 日本曹達株式会社 Composition bactéricide pour l'agriculture et l'horticulture
WO2013047749A1 (fr) 2011-09-29 2013-04-04 三井化学アグロ株式会社 Procédé de fabrication de dérivé de 4,4-difluoro-3,4-dihydroisoquinoléine
WO2013092224A1 (fr) 2011-12-21 2013-06-27 Basf Se Utilisation de composés de type strobilurine pour combattre des champignons phytopathogènes résistants aux inhibiteurs du site qo
WO2013112527A1 (fr) 2012-01-23 2013-08-01 Dow Agrosciences Llc Coton résistant aux herbicides évènement pdab4468.19.10.3
WO2013116251A2 (fr) 2012-02-01 2013-08-08 E. I. Du Pont De Nemours And Company Mélanges de pyrazole fongicides
WO2013127704A1 (fr) 2012-02-27 2013-09-06 Bayer Intellectual Property Gmbh Associations de composés actifs contenant une thiazoylisoxazoline et un fongicide
WO2013162072A1 (fr) 2012-04-27 2013-10-31 Sumitomo Chemical Company, Limited Composés de tétrazolinone et leur utilisation en tant que pesticides
WO2013169923A2 (fr) 2012-05-08 2013-11-14 Monsanto Technology Llc Événement de maïs mon 87411
CN103387541A (zh) 2012-05-10 2013-11-13 中国中化股份有限公司 一种取代吡唑醚类化合物的制备方法
WO2014060177A1 (fr) 2012-10-16 2014-04-24 Syngenta Participations Ag Compositions fongicides
WO2014116854A1 (fr) 2013-01-25 2014-07-31 Pioneer Hi-Bred International, Inc. Événement de maïs dp-033121-3 et ses procédés de détection
WO2014178910A1 (fr) 2013-05-02 2014-11-06 J.R. Simplot Company Cultivar de pomme de terre e12
WO2014178941A1 (fr) 2013-05-02 2014-11-06 J.R. Simplot Company Cultivar de pomme de terre j3
WO2014179276A1 (fr) 2013-05-02 2014-11-06 J.R. Simplot Company Cultivar de pomme de terre j55
WO2014178913A1 (fr) 2013-05-02 2014-11-06 J.R. Simplot Company Cultivar de pomme de terre f10
WO2014201235A2 (fr) 2013-06-14 2014-12-18 Monsanto Technology Llc Événement transgénique de soja mon87751 et procédés de détection et d'utilisation de celui-ci
WO2015053998A1 (fr) 2013-10-09 2015-04-16 Monsanto Technology Llc Événement de maïs transgénique mon87403 et procédés pour la détection de celui-ci
WO2015065922A1 (fr) 2013-10-28 2015-05-07 Dexcom, Inc. Dispositifs utilisés en relation avec une surveillance continue de substances à analyser pour fournir une ou plusieurs notifications à un utilisateur, et procédés associés
JP2015089883A (ja) 2013-11-06 2015-05-11 アグロカネショウ株式会社 ２−アミノニコチン酸ベンジルエステル誘導体およびこれを有効成分とする殺菌剤
JP2015120675A (ja) 2013-12-25 2015-07-02 アグロカネショウ株式会社 ６−置換ニコチン酸エステル誘導体およびこれを有効成分とする殺菌剤
WO2015119246A1 (fr) 2014-02-07 2015-08-13 日産化学工業株式会社 Composition bactéricide ou de stérilisation et méthode de lutte contre les maladies
EP2865265A1 (fr) 2014-02-13 2015-04-29 Bayer CropScience AG Combinaisons de composés actifs comprenant des composés phénylamidine et agents de lutte biologique
WO2015142571A1 (fr) 2014-03-20 2015-09-24 Monsanto Technology Llc Événement transgénique de maïs mon 87419 et méthodes d'utilisation de celui-ci
WO2016183445A1 (fr) 2015-05-14 2016-11-17 J.R. Simplot Company Cultivar de pomme de terre v11
WO2017062825A1 (fr) 2015-10-08 2017-04-13 J.R. Simplot Company Cultivar de pomme de terre y9
WO2017062831A1 (fr) 2015-10-08 2017-04-13 J.R. Simplot Company Cultivar de pomme de terre x17

Non-Patent Citations (31)

* Cited by examiner, † Cited by third party
Title
"Technical Monograph", May 2008, CROPLIFE INTERNATIONAL, article "Catalogue of pesticide formulation types and international coding system"
ANGEW. CHEM. INT. ED., 2012, pages 9173 - 9175
AUST. J. CHEM., 1973, pages 1591 - 3
CAN. J. PLANT SCI., vol. 48, no. 6, 1968, pages 587 - 94
CHEM. REV., 2010, pages 3600 - 3740
CHEM. SOC. REV., 2009, pages 606 - 631
ENVIRON MICROBIOL, vol. 16, 2014, pages 2253 - 66
J. AM. CHEM. SOC., vol. 123, no. 25, 2001, pages 5962 - 5973
J. HETEROCYC. CHEM., vol. 18, no. 7, 1981, pages 1305 - 8
J. HETEROCYCL. CHEM., 1981, pages 1305 - 8
J. MED. CHEM., vol. 38, no. 11, 1995, pages 1892 - 903
J. ORG. CHEM., 1984, pages 4212 - 4216
J. ORG. CHEM., vol. 79, 2014, pages 1254 - 1264
JOURNAL OF PLANT DISEASES AND PROTECTION, vol. 125, pages 21 - 26
KNOWLES: "Adjuvants and additives, Agrow Reports DS256", 2006, T&F INFORMA UK
KNOWLES: "Agrow Reports DS243", 2005, T&F INFORMA, article "New developments in crop protection product formulation"
MCCUTCHEON: "Emulsifiers & Detergents", vol. 1, 2008, MCCUTCHEON'S DIRECTORIES
MOLLETGRUBE-MANN: "Formulation technology", 2001, WILEY VCH
ORG. LETT., 2005, pages 2787 - 2790
ORG. LETT., 2014, pages 4296 - 4299
PEST MANAG SCI, vol. 70, 2014, pages 378 - 388
PEST MANAG SCI, vol. 72, no. 121, 2016, pages 1 - 1215
PEST MANAG SCI, vol. 74, 2018, pages 672 - 681
PHYTOPATHOL, vol. 106, 2016, pages 1278 - 1284
PHYTOPATHOL, vol. 93, 2003, pages 891 - 900
PHYTOPATHOL, vol. 98, 2008, pages 397 - 404
SDHI, vol. 58, 2002, pages 876 - 88
SMITHMARCH: "March's Advanced Organic Chemistry", 2007, WILEY
SYNLETT, vol. 10, 2004, pages 1691 - 1694
SYNTHESIS, 2011, pages 1477 - 1483
TETRAHEDRON, 2005, pages 10827 - 10852

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