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WO2007112844A1 - Nouvelles modifications cristallines de 3-chloro-n2-[(1s)-1-méthyl-2-(méthylsulfonyl)éthyl]-n1-{2-méthyl-4-[1,2,2,2-tétrafluoro-1-(trifluorométhyl)-éthyl]phényl}phtalamide - Google Patents

Nouvelles modifications cristallines de 3-chloro-n2-[(1s)-1-méthyl-2-(méthylsulfonyl)éthyl]-n1-{2-méthyl-4-[1,2,2,2-tétrafluoro-1-(trifluorométhyl)-éthyl]phényl}phtalamide Download PDF

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Publication number
WO2007112844A1
WO2007112844A1 PCT/EP2007/002388 EP2007002388W WO2007112844A1 WO 2007112844 A1 WO2007112844 A1 WO 2007112844A1 EP 2007002388 W EP2007002388 W EP 2007002388W WO 2007112844 A1 WO2007112844 A1 WO 2007112844A1
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WO
WIPO (PCT)
Prior art keywords
methyl
ethyl
phthalamide
chloro
phenyl
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Ceased
Application number
PCT/EP2007/002388
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German (de)
English (en)
Inventor
Britta Olenik
Rüdiger Fischer
Christian Funke
Lorna Elisabeth Davies
Gerhard Thielking
Sergiy Pazenok
Hiroto Harayama
Hayami Nakao
Michihiko Kawaguchi
Masanori Tohnishi
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Bayer CropScience AG
Original Assignee
Bayer CropScience AG
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Priority claimed from DE200610014491 external-priority patent/DE102006014491A1/de
Priority claimed from DE200610031647 external-priority patent/DE102006031647A1/de
Application filed by Bayer CropScience AG filed Critical Bayer CropScience AG
Publication of WO2007112844A1 publication Critical patent/WO2007112844A1/fr
Anticipated expiration legal-status Critical
Ceased legal-status Critical Current

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C317/00—Sulfones; Sulfoxides
    • C07C317/26—Sulfones; Sulfoxides having sulfone or sulfoxide groups and nitrogen atoms, not being part of nitro or nitroso groups, bound to the same carbon skeleton
    • C07C317/28—Sulfones; Sulfoxides having sulfone or sulfoxide groups and nitrogen atoms, not being part of nitro or nitroso groups, bound to the same carbon skeleton with sulfone or sulfoxide groups bound to acyclic carbon atoms of the carbon skeleton
    • 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
    • A01N41/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a sulfur atom bound to a hetero atom
    • A01N41/02—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a sulfur atom bound to a hetero atom containing a sulfur-to-oxygen double bond
    • A01N41/10—Sulfones; Sulfoxides

Definitions

  • the present invention relates to novel crystalline modifications of 3-chloro-N 2 - [(1S) -l-methyl-2- (methylsulfonyl) ethyl] -N 1 - ⁇ 2-methyl-4-[1,2] 2,2-tetrafluoro-1- (trifluoromethyl) ethyl] phenyl ⁇ phthalamide (hereinafter referred to as CMP, see formula (A)), processes for their preparation and their use in agrochemical preparations.
  • CMP 3-chloro-N 2 - [(1S) -l-methyl-2- (methylsulfonyl) ethyl] -N 1 - ⁇ 2-methyl-4-[1,2] 2,2-tetrafluoro-1- (trifluoromethyl) ethyl] phenyl ⁇ phthalamide
  • CMP is known as a racemate from EP-A 1 006 107 and as a pure enantiomer from unpublished Japanese patent application JP 2005-239974.
  • CMP can be synthesized by the methods described therein. Another method is described in International Patent Application PCT / EP05 / 00894.
  • the invention therefore relates to the crystalline modification I of CMP, which is characterized in that it has an X-ray powder diffractogram with the reflective layers given in Table 1 (2 theta,> 20% relative intensity).
  • the powder X-ray diffraction pattern of the crystalline modification I is also shown in FIG.
  • the most intense signals (2 theta) of the X-ray powder diffraction pattern of the crystalline modification I are thus at 19.42 °, 12.93 °, 19.91 °, 18.51 °, 14.39 °, 13.24 °, 14.76 ° and 18.81 ° (each ⁇ 0.2 °).
  • the invention likewise relates to the crystalline modification II of CMP, which is characterized in that it has an X-ray powder diffractogram with the reflective layers specified in Table 2 below (2 theta,> 20% relative intensity).
  • the powder X-ray diffractogram of the crystalline modification II is also shown in FIG.
  • the most intense signals (2 theta) of the X-ray powder diffraction pattern of the crystalline modification ⁇ are thus at 14.74 °, 10.29 °, 16.43 °, 23.89 °, 15.28 °, 11.61 °, 15.84 ° and 18.50 ° (each ⁇ 0, 2 °).
  • the invention likewise provides the crystalline modification III of CMP, which is characterized in that it has an X-ray powder diffractogram with the reflective layers (2 theta,> 20% relative intensity) given in Table 3 below.
  • the powder X-ray diffraction pattern of the crystalline modification III is also shown in FIG.
  • the most intense signals (2 theta) of the X-ray powder diffraction pattern of the crystalline modification ⁇ i are therefore 21.84 °, 15.52 °, 9.50 °, 14.57 °, 13.43 °, 25.79 °, 16.50 ° and 23.22 ° (each ⁇ 0.2 °).
  • weak is preferably understood an intensity of 20 to 40% of the most intense signal in the spectrum, “medium” an intensity of> 40 to 60% of the most intense signal in the spectrum under “strong” an intensity of> 60 to 80 % of the most intense signal in the spectrum and under “very strong” an intensity of> 80 to 100% of the most intense signal in the spectrum
  • weak is preferably understood an intensity of 20 to 40% of the most intense signal in the spectrum, “medium” an intensity of> 40 to 60% of the most intense signal in the spectrum under “strong” an intensity of> 60 to 80 % of the most intense signal in the spectrum and under “very strong” an intensity of> 80 to 100% of the most intense signal in the spectrum
  • weak is preferably understood an intensity of 20 to 40% of the most intense signal in the spectrum, “medium” an intensity of> 40 to 60% of the most intense signal in the spectrum under “strong” an intensity of> 60 to 80 % of the most intense signal in the spectrum and under “very strong” an intensity of> 80 to 100% of the most intense signal in the spectrum
  • the known crystalline modification IV of CMP is characterized in that it has an X-ray powder diffractogram with the reflective layers given in Table 4 below (2 theta,> 20% relative intensity).
  • the powder X-ray diffraction pattern of the crystalline modification IV is also shown in FIG.
  • weak is preferably understood an intensity of 20 to 40% of the most intense signal in the spectrum, “medium” an intensity of> 40 to 60% of the most intense signal in the spectrum under “strong” an intensity of> 60 to 80 % of the most intense signal in the spectrum and under “very strong” an intensity of> 80 to 100% of the most intense signal in the spectrum
  • the crystalline modifications of CMP according to the invention can also be characterized by BR spectroscopy.
  • the ER spectra contain the following band maxima listed in Table 5 (crystalline modification I), Table 6 (crystalline modification II) and Table 7 (crystalline modification III) (measured on FTIR Tensor 37, Bruker, Bremen, Germany using a Golden Gate ATR unit for solids):
  • the known crystalline modification IV of CMP can also be characterized by IR spectroscopy.
  • the IR spectrum contains the following band maxima listed in Table 8 (measured on FTIR Tensor 37, Bruker, Bremen, Germany using a Golden Gate ATR unit for solids):
  • the crystalline modifications of the invention can also be characterized by Raman spectroscopy.
  • the band maxima (measured on a Raman R100 / S, Bruker, Breyer men, Germany) are listed in Table 9 (crystalline modification I), Table 10 (crystalline modification II) and Table 1 1 (crystalline modification HI):
  • the known crystalline modification IV can also be characterized by Raman spectroscopy.
  • the band maxima (measured on a Raman R100 / S, Bruker, Bremen, Germany) are listed in Table 12: Table 12
  • CMP of the crystalline modification I is surprisingly stable and does not convert to any other crystalline modifications even after prolonged storage.
  • the crystalline modification I has a much lower tendency to absorb water from the air. For these reasons, it is excellently suitable for the production of solid formulations. Its stability gives these formulations the desired long-term storage stability. With the crystalline modification I can thus be defined and produced specifically stable solid preparations of CMP.
  • CMP of crystalline modification II or FV is suspended in at least one apolar organic solvent and heated.
  • CMP of crystalline modification II or IV is suspended in a mixture of at least one apolar organic solvent and at least one polar solvent and heated. After recrystallization, the precipitate is isolated and dried.
  • apolar organic solvent is preferably a branched, unbranched or cyclic hydrocarbon, more preferably an unbranched or cyclic hydrocarbon, most preferably n-pentane, n-hexane, n-heptane, cyclohexane, n-octane, n-nonane or n Decane, and particularly preferably n-octane or heptane.
  • Preferred polar solvents are esters (such as, for example, methyl acetate, ethyl acetates or propyl acetates), nitriles (such as, for example, acetonitrile, butyronitrile or benzonitrile), ethers (such as, for example, dimethoxoethanes, diglyme, THF, dioxanes, NMP, sulpholane or DMAA), Alcohols (such as methanol, ethanol or isopropanol) or acetic acid used.
  • esters such as, for example, methyl acetate, ethyl acetates or propyl acetates
  • nitriles such as, for example, acetonitrile, butyronitrile or benzonitrile
  • ethers such as, for example, dimethoxoethanes, diglyme, THF, dioxanes, NMP, sulpholane or DM
  • the mixing ratio (organic solvent: polar solvent, v / v) is generally from 1000: 1 to 30: 1, more preferably 500: 1 to 25: 1, more preferably 400: 1 to 20: 1 and most preferably 300: 1 to 15: 1.
  • the CMP of the crystalline modification FV is preferably used in a concentration of 10 to 500 g / l, more preferably in a concentration of 25 to 300 g / l and particularly preferably in a concentration of 50 to 250 g / l.
  • the recrystallization time can be varied within a wide range. It is preferably 1 to 24 hours, more preferably 2 to 12 hours and most preferably 4 to 8 hours.
  • the recrystallization can be carried out in a wide temperature range. Preferably, it is at the boiling point of the solvent mixture under reflux at 80 - from 150 0 C, preferably at 90 - 12O 0 C and most preferably at 100-120 0 C.
  • the reaction mixture may be added with CMP of the crystalline modification I as a seed for improving the yield or shortening the necessary recrystallization time.
  • CMP of crystalline modification IV is heated in a mixture of apolar organic solvent and ethyl acetate.
  • apolar organic solvent is preferably a branched, unbranched or cyclic hydrocarbon, more preferably an unbranched or cyclic hydrocarbon, most preferably n-pentane, n-hexane, cyclohexane, n-heptane, n-octane and especially preferably cyclohexane or n -Hexan used.
  • the two solvents are preferably in a mixing ratio (OLM: EA, v / v) of 1000: 1 to 1: 2, particularly preferred 500: 1 to 1: 1, most preferably 200: 1 to 1: 1 and particularly preferably 100: 1 to 2: 1 used.
  • ODM organic solvent
  • EA ethyl acetate
  • the recrystallization for the preparation of the crystalline modification I by the process B according to the invention is preferably carried out in a mixture of n-hexane and ethyl acetate.
  • CMP of the crystalline modification IV is preferably used in a concentration of 10 to 500 g / l, more preferably in a concentration of 25 to 300 g / l and particularly preferably in a concentration of 50 to 200 g / l.
  • the recrystallization time can be varied within a wide range. It is preferably 0.5 to 24 hours, more preferably 1 to 12 hours and most preferably 2 to 8 hours.
  • Step 1 of the method B according to the invention can be carried out in a wide temperature range. It is preferably carried out under reflux at the boiling point of the solvent mixture, as long as the boiling point does not exceed 100 ° C. In a solvent mixture having a boiling point of more than 100 0 C, it is carried out at a temperature of 60 0 C to 100 0 C, preferably at 70 0 C to 100 0 C and particularly preferably at 70 to 90 0 C.
  • the reaction mixture may be added with CMP of the crystalline modification I as a seed for improving the yield or shortening the necessary recrystallization time.
  • step 2 The mixture is then cooled, the product is filtered off and dried. step 2
  • step 1 The Maieriai obtained from step 1 is stirred in water with heating, cooled Anlagen ⁇ itriert. Subsequently, the material is dried.
  • the material obtained from step 1 is introduced in water as suspension in a concentration of 10 to 500 g / l, preferably 20 to 250 g / l, particularly preferably 50 to 200 g / l.
  • Step 2 of the process B according to the invention can be carried out in a wide temperature range (bounded above by the boiling point of water). Preferably, it is carried out above 70 0 C, more preferably above 8O 0 C and most preferably in boiling water (100 0 C).
  • step 2 can be varied within a wide range.
  • step 2 is carried out between 0.5 and 24 hours, more preferably between 1 and 12 hours and most preferably between 2 and 6 hours.
  • the product is preferably obtained after the implementation of step 2 by filtration and then dried (for example in a drying oven or in a desiccator over a drying agent such as P 2 O 5 or CaCl 2 ).
  • the recrystallization can be carried out in a wide temperature range (limited above by the boiling point of water).
  • the recrystallization reaction is preferably carried out above 40 ° C., more preferably above 60 ° C., and most preferably in boiling water (100 ° C.).
  • step 2 is carried out between 0.5 and 24 hours, more preferably between 1 and 12 hours, and most preferably between 1 and 6 hours.
  • CMP of the crystalline modification II is introduced for the process C according to the invention in water as a suspension in a concentration of 10 to 500 g / l, preferably 20 to 250 g / l, particularly preferably 50 to 200 g / l.
  • CMP of the crystalline modification HI can be obtained by the following method:
  • CMP of crystalline modification IV is heated in a mixture of an apolar organic solvent and an alcohol, and the resulting precipitate formed by suitable known methods, e.g. Filtration, isolated.
  • the apolar organic solvent (OLM) used is preferably a branched or unbranched hydrocarbon, particularly preferably an unbranched hydrocarbon, very particularly preferably n-pentane, n-hexane, n-heptane, n-octane and particularly preferably n-hexane.
  • the alcohol (AL) used is preferably a branched or unbranched alcohol having two to five carbon atoms, particularly preferably ethanol, n-propanol, isopropanol, n-butanol, isobutanol or t-butanol, most preferably n-propanol.
  • the recrystallization is carried out in a mixture of n-hexane and n-propanol.
  • the solvents used for the recrystallization are preferably in a mixing ratio (OLM: AL, v / v) of 200: 1 to 1: 2, more preferably 100: 1 to 1: 1, most preferably 20: 1 to 1: 1 and more preferably 5: 1 to 1: 1 used.
  • OLM a mixing ratio
  • the recrystallization can be carried out in a wide temperature range, preferably at 70-130 ° C.
  • the duration of the recrystallization can be varied within a wide range. Preference is first heated under reflux, then without reflux. The heating under reflux is generally carried out for 5 minutes to 6 hours, preferably 5 minutes to 2 hours and particularly preferably 10 to 60 minutes. The subsequent heating without reflux is generally carried out for 10 minutes to 6 hours, preferably for 20 minutes to 3 hours, particularly preferably for 30 minutes to 2 hours. Subsequently, the recrystallization solution is left to stand without heating until the recrystallized material has precipitated. This resting phase generally lasts 1 to 48 hours, preferably 3 to 24 hours, more preferably 6 to 18 hours.
  • CMP of the crystalline modification IV is introduced for the process D according to the invention in a concentration of 10 to 500 g / l, preferably 20 to 250 g / l, particularly preferably 50 to 200 g / l.
  • concentration 10 to 500 g / l, preferably 20 to 250 g / l, particularly preferably 50 to 200 g / l.
  • the crystalline modification I of CMP was obtained by suspending CMP of crystalline modification IV, as obtained from the known synthesis process, in n-octane / ethyl acetate (100: 1 v / v) at a concentration of 165 g / l, and was stirred at 1 15 to 120 0 C for six hours. Thereafter, the precipitate was isolated by filtration and dried in vacuo. It was obtained in a yield of 97 to 99%, a material having a melting point of 168 - 17O 0 C, which consisted of 90 to 95% of the crystalline modification I.
  • the crystalline modification I of CMP was obtained by CMP fication of the crystalline medi- IV, as it is recovered from the known synthesis process, l suspended in n-octane in a concentration of 147 g / and six hours at 1 15 to 120 0 C was stirred. Thereafter, the precipitate was isolated by filtration and dried in vacuo. There was a yield of 97 to 99%, the crystalline modification I of CMP with a melting point 168-170 0 C. (proportion of crystal modification I 90 to 95%).
  • the crystalline modification I of CMP was obtained by reacting CMP of the crystalline modification IV, as obtained from the known synthesis process, in hexane / ethyl acetate
  • the crystalline modification I of CMP was obtained by subjecting CMP of the crystalline modification rv, as obtained from the synthesis process described, in hexane / ethyl acetate (3: 1 v / v) in a concentration of 83 g / l for 2 hours Reflux was stirred. Subsequently, the batch was cooled and the precipitated material was recovered by filtration. The The material obtained was stirred at a concentration of 172 g / l in water for about 3 hours under reflux and the precipitated material was recovered by filtration. The desiccator was finally dried over CaCl 2 . The crystalline modification I of CMP with a melting point of 169 ° C. was obtained with a yield of 83%.
  • the crystalline modification IE of CMP was obtained by reacting CMP of the crystalline modification IV, as obtained from the described synthesis process, in a mixture of n-hexane and n-propanol (3: 1, v / v) in a concentration of 50 g / l was dissolved and heated under reflux for 20 minutes. The reaction solution was heated for a further hour without reflux and then allowed to stand for 12 hours without stirring. The formed precipitate was filtered off. There was a yield of 48%, the crystalline modification III of CMP with a melting point of 140 - 143 obtained 0C.
  • a formulation of CMP in the form of a soluble concentrate (SC) is prepared.
  • the particle size immediately after production was about 1.5 ⁇ m (FIG. 5 a). It was then stored at 54 ° C for six weeks. After this storage, a formulation using only about 50% Modification I showed significant crystal growth and an average particle size of about 8 ⁇ m ( Figure 5 b).
  • a formulation containing about 80-85% of modification I showed particle sizes of about 6 ⁇ m ( Figure 5 c).
  • formulations containing active ingredient> 90% Modification I showed almost no crystal growth at particle sizes of approximately 1.8 ⁇ m ( Figure 5 d).

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Agronomy & Crop Science (AREA)
  • Pest Control & Pesticides (AREA)
  • Plant Pathology (AREA)
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Abstract

La présente invention concerne des modifications cristallines définies de 3-chloro-N<SUP>2</SUP>-[(1S)-1-méthyl-2-(méthylsulfonyl)éthyl]-N<SUP>1</SUP>-{2-méthyl-4-[1,2,2,2-tétrafluoro-1-(trifluorométhyl)-éthyl]phényl}phtalamide de formule (A), leurs procédés de fabrication et leur utilisation dans des compositions agrochimiques.
PCT/EP2007/002388 2006-03-29 2007-03-19 Nouvelles modifications cristallines de 3-chloro-n2-[(1s)-1-méthyl-2-(méthylsulfonyl)éthyl]-n1-{2-méthyl-4-[1,2,2,2-tétrafluoro-1-(trifluorométhyl)-éthyl]phényl}phtalamide Ceased WO2007112844A1 (fr)

Applications Claiming Priority (4)

Application Number Priority Date Filing Date Title
DE200610014491 DE102006014491A1 (de) 2006-03-29 2006-03-29 Neue kristalline Modifikationen von3-Chlor-N2-[(1S)-1-methyl-2-(methyl-sulfonyl)ethyl]-N1-{2-methyl-4-[1,2,2,2-tetrafluor-1(trifluormethyl)-ethyl]}phthalamid
DE102006014491.0 2006-03-29
DE102006031647.9 2006-07-08
DE200610031647 DE102006031647A1 (de) 2006-07-08 2006-07-08 Neue kristalline Modifikationen von 3-Chlor-N2-[(1S)-1-methyl-2-(methyl-sulfonyl)ethyl]-N1-{2-methyl-4[1,2,2,2-tetrafluor-1-(trifluormethyl)-ethyl]phenyl}phthalamid

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WO2007112844A1 true WO2007112844A1 (fr) 2007-10-11

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PCT/EP2007/002388 Ceased WO2007112844A1 (fr) 2006-03-29 2007-03-19 Nouvelles modifications cristallines de 3-chloro-n2-[(1s)-1-méthyl-2-(méthylsulfonyl)éthyl]-n1-{2-méthyl-4-[1,2,2,2-tétrafluoro-1-(trifluorométhyl)-éthyl]phényl}phtalamide

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AR (1) AR060135A1 (fr)
TW (1) TW200811092A (fr)
WO (1) WO2007112844A1 (fr)

Cited By (16)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2011067203A1 (fr) 2009-12-04 2011-06-09 Syngenta Participations Ag Composes chimiques et leur utilisation comme pesticides
WO2011067131A1 (fr) 2009-12-04 2011-06-09 Syngenta Participations Ag Derives spiroheterocycliques de dione utilises comme pesticides
WO2011067240A1 (fr) 2009-12-04 2011-06-09 Syngenta Participations Ag Derives de 1 -amino - piperidine pyrrolidine dione spiro fusionnes a activite pesticide
WO2011095462A1 (fr) 2010-02-03 2011-08-11 Syngenta Participations Ag Composés insecticides
WO2011113756A1 (fr) 2010-03-18 2011-09-22 Syngenta Participations Ag Composés insecticides
WO2011151194A1 (fr) 2010-05-31 2011-12-08 Syngenta Participations Ag Dérivés de 1,8-diazaspiro[4.5]décane-2,4-dione, utiles en tant que pesticides
WO2011151199A1 (fr) 2010-05-31 2011-12-08 Syngenta Participations Ag Pesticides à base de dérivés de pyrrolidine spirohétérocyclique
WO2011151197A1 (fr) 2010-05-31 2011-12-08 Syngenta Participations Ag Dérivés de 1,8-diazaspiro[4.5]décane-2,4-dione, utiles en tant que pesticides
WO2012069366A1 (fr) 2010-11-23 2012-05-31 Syngenta Participations Ag Composés insecticides
WO2012175474A1 (fr) 2011-06-20 2012-12-27 Syngenta Participations Ag Pesticides à base de 1,2,3-triazole
WO2012175666A1 (fr) 2011-06-22 2012-12-27 Syngenta Participations Ag Dérivés n-oxy pyrazolo-triazépine-dione
WO2013079350A1 (fr) 2011-11-29 2013-06-06 Syngenta Participations Ag Dérivés de triazinone insecticides
WO2013127768A1 (fr) 2012-03-01 2013-09-06 Syngenta Participations Ag Pesticides à base de pyridinecarboxamide
WO2013127780A1 (fr) 2012-03-01 2013-09-06 Syngenta Participations Ag Composés chimiques
EP2647626A1 (fr) 2012-04-03 2013-10-09 Syngenta Participations AG. Dérivés de 1-aza-spiro[4.5]déc-3-ène and 1,8-diaza-spiro[4.5]déc-3-ène en tant que pesticides
WO2014023531A1 (fr) 2012-08-07 2014-02-13 Syngenta Participations Ag Trifluorométhylpyridine carboxamides comme pesticides

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Publication number Priority date Publication date Assignee Title
EP1006107A2 (fr) * 1998-11-30 2000-06-07 Nihon Nohyaku Co., Ltd. Dérivés de phtalamide ou leur sels, insecticides pour l'agriculture et l'horticulture et procédé pour leur mise en oeuvre
WO2006022225A1 (fr) * 2004-08-23 2006-03-02 Nihon Nohyaku Co., Ltd. Dérivé optiquement actif de phtalimide, insecticide pour l'agriculture ou l'horticulture et procédé d'utilisation de celui-ci
JP2006089469A (ja) * 2004-08-23 2006-04-06 Nippon Nohyaku Co Ltd 光学活性フタルアミド誘導体及び農園芸用殺虫剤並びにその使用方法

Patent Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP1006107A2 (fr) * 1998-11-30 2000-06-07 Nihon Nohyaku Co., Ltd. Dérivés de phtalamide ou leur sels, insecticides pour l'agriculture et l'horticulture et procédé pour leur mise en oeuvre
WO2006022225A1 (fr) * 2004-08-23 2006-03-02 Nihon Nohyaku Co., Ltd. Dérivé optiquement actif de phtalimide, insecticide pour l'agriculture ou l'horticulture et procédé d'utilisation de celui-ci
JP2006089469A (ja) * 2004-08-23 2006-04-06 Nippon Nohyaku Co Ltd 光学活性フタルアミド誘導体及び農園芸用殺虫剤並びにその使用方法
EP1782689A1 (fr) * 2004-08-23 2007-05-09 Nihon Nohyaku Co., Ltd. Dérivé optiquement actif de phtalimide, insecticide pour l'agriculture ou l'horticulture et procédé d'utilisation de celui-ci

Cited By (18)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2011067203A1 (fr) 2009-12-04 2011-06-09 Syngenta Participations Ag Composes chimiques et leur utilisation comme pesticides
WO2011067131A1 (fr) 2009-12-04 2011-06-09 Syngenta Participations Ag Derives spiroheterocycliques de dione utilises comme pesticides
WO2011067240A1 (fr) 2009-12-04 2011-06-09 Syngenta Participations Ag Derives de 1 -amino - piperidine pyrrolidine dione spiro fusionnes a activite pesticide
WO2011067135A1 (fr) 2009-12-04 2011-06-09 Syngenta Participations Ag Derives de 1 -amino - piperidine pyrrolidine dione spiro fusionnes a activite pesticide
WO2011095462A1 (fr) 2010-02-03 2011-08-11 Syngenta Participations Ag Composés insecticides
WO2011113756A1 (fr) 2010-03-18 2011-09-22 Syngenta Participations Ag Composés insecticides
WO2011151194A1 (fr) 2010-05-31 2011-12-08 Syngenta Participations Ag Dérivés de 1,8-diazaspiro[4.5]décane-2,4-dione, utiles en tant que pesticides
WO2011151199A1 (fr) 2010-05-31 2011-12-08 Syngenta Participations Ag Pesticides à base de dérivés de pyrrolidine spirohétérocyclique
WO2011151197A1 (fr) 2010-05-31 2011-12-08 Syngenta Participations Ag Dérivés de 1,8-diazaspiro[4.5]décane-2,4-dione, utiles en tant que pesticides
WO2012069366A1 (fr) 2010-11-23 2012-05-31 Syngenta Participations Ag Composés insecticides
WO2012175474A1 (fr) 2011-06-20 2012-12-27 Syngenta Participations Ag Pesticides à base de 1,2,3-triazole
WO2012175666A1 (fr) 2011-06-22 2012-12-27 Syngenta Participations Ag Dérivés n-oxy pyrazolo-triazépine-dione
WO2013079350A1 (fr) 2011-11-29 2013-06-06 Syngenta Participations Ag Dérivés de triazinone insecticides
WO2013127768A1 (fr) 2012-03-01 2013-09-06 Syngenta Participations Ag Pesticides à base de pyridinecarboxamide
WO2013127780A1 (fr) 2012-03-01 2013-09-06 Syngenta Participations Ag Composés chimiques
EP2647626A1 (fr) 2012-04-03 2013-10-09 Syngenta Participations AG. Dérivés de 1-aza-spiro[4.5]déc-3-ène and 1,8-diaza-spiro[4.5]déc-3-ène en tant que pesticides
WO2013150015A1 (fr) 2012-04-03 2013-10-10 Syngenta Participations Ag Dérivés de 1-aza-spiro[4.5]déc-3-ène et de 1,8-diaza-spiro[4.5]déc-3-ène en tant que pesticides
WO2014023531A1 (fr) 2012-08-07 2014-02-13 Syngenta Participations Ag Trifluorométhylpyridine carboxamides comme pesticides

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