New trifluoromethoxy-phenyl substituted tetramic acid-derivatives useful to combat parasites including insects, arachnid, helminth, nematode and mollusk and/or undesirable plant growth and in hygienic sectors
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A compound, meaning technology, applied in the field of Tetramic acid derivatives, can solve the problems that the activity and activity spectrum of the compound are not always completely satisfactory, and the plant compatibility is not always sufficient, etc.
Inactive Publication Date: 2014-05-14
BAYER IP GMBH
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[0007] However, especially at low application rates and concentrations, the activity and activity spectrum of these compounds are not always completely satisfactory
Furthermore, the compatibility of these compounds with some crop plants is not always sufficient
Method used
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Embodiment I-a-1
[0969]
[0970] Under argon, 4.26 g of potassium tert-butoxide (36 mmol) were first added to 10 ml of dimethylacetamide. 8.5 g (16.4 mmol) of the compound of Example II-1 in 15 ml of dimethylacetamide were added dropwise at -20 to -30°C. The mixture was stirred at 20° C. for 1 h (the reaction was monitored by thin layer chromatography). After the reaction, the reaction solution was stirred into 100 ml of ice water, the pH was adjusted to 2 with concentrated hydrochloric acid, and the precipitate was filtered off with suction. The precipitate was redissolved in 40 ml of dichloromethane, and 20 ml of 0.5N NaOH solution was added dropwise. The mixture was stirred at 20 °C for 1 h. The aqueous phase was adjusted to pH 2 and the precipitate was filtered off with suction.
[0971] The product was purified by silica gel column chromatography (dichloromethane:ethyl acetate=5:3).
[0972] Yield: 4.2 g (51% of theory), melting point 259°C.
[0973] In a similar manner to Example...
Embodiment I-b-1
[0982]
[0983] Under argon, first add 0.5 g (1 mmol) of the compound of Example I-a-1 into ethyl acetate, add 0.14 ml of triethylamine and 10 mg of Steglich base, and add the compound dissolved in 5 ml of ethyl acetate dropwise under reflux. 0.1 ml of 2-methylpropanoyl chloride in , and the mixture was stirred under reflux.
[0984] After completion of the reaction (reaction monitored by thin layer chromatography), the mixture was separated by RP column chromatography (water / acetonitrile: 50 / 50→10 / 90).
[0985] Yield: 0.23 g (40% of theory), melting point 219°C.
[0986] In a similar manner to Example (I-b-1) and according to the general description of the preparation, the following compound of formula (I-b) is obtained:
[0987]
[0988]
[0989] 1) 2.61 (m, 1H, C H (C5)); 2.70(m, 1H(C H (CH 3 ) 2 ); 7.31, 7.44 (respectively dd, 1H, Ar H )
[0990] 2) 2.70(m, 1H, CH(C H 3 ) 2 ); 4.79 (m, 1H, CH(C5); 7.47 (dd, 2-H, Ar H )
[0991] 3) 2.62(m, 1H CH(C5); 2.70...
Embodiment I-c-1
[0999]
[1000] Under argon, first add 0.5 g (1 mmol) of the compound of Example I-a-1 into dichloromethane, add 0.14 ml of triethylamine, and add dropwise methyl chloride dissolved in 5 ml of dichloromethane at about 20° C. acid ester (0.1 ml), and the mixture was stirred at 20-30°C.
[1001] After completion of the reaction (reaction monitored by thin layer chromatography), the mixture was separated by RP column chromatography (water / acetonitrile: 50 / 50→10 / 90).
[1002] Yield: 0.415 g (74% of theory), melting point 194°C.
[1003] In a similar manner to Example (I-c-1) and according to the general description of the preparation, the following compound of formula (I-c) is obtained:
[1004]
[1005]
[1006]
[1007] 1) 4.29 (m, 2H, O CH 2 -CH 3 ); 4.81 (m, 1H, C H (C5)); 7.33, 7.47 (dd, 1H, Ar respectively H )
[1008] 2) 2.62(m, 1H, CH (C5)); 4.26 (m, 2H, O CH 2 CH 3 ); 7.32, 7, 45 (respectively dd, 1H, Ar H )
[1009] 3) 4.27(q, 2H, OCH 2 ); 4....
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Abstract
Trifluoromethoxy-phenyl substituted tetramic acid-derivatives (I), are new. Trifluoromethoxy-phenyl substituted tetramic acid-derivatives of formula (I), are new. J1a : trifluoromethoxy; X : H, alkyl, halo, haloalkyl, alkoxy or haloalkoxy; Y1a : H, alkyl or halo, where at least one of J1a, X or Y1a is present at position-2 of the phenyl residue and is at the same time unequally hydrogen; either A : alkyl, alkenyl, alkoxyalkyl, alkylthioalkyl, optionally saturated cycloalkyl (all optionally substituted by halo and at least a ring atom is optionally substituted by a heteroatom), aryl, arylalkyl, hetaryl (all optionally substituted by halo, (halo)alkyl, (halo)alkoxy, cyano or nitro) or H; and B1a : H or alkoxyalkyl; and D : H or a residue optionally substituted by alkyl, alkenyl, alkynyl, alkoxyalkyl, optionally saturated cycloalkyl, in which optionally one or more ring members are substituted by heteroatom, arylalkyl, aryl, hetarylalkyl or hetaryl; or C+A+B1a : optionally saturated, substituted and heteroatom containing cyclic group; or A+D : optionally saturated and at least a heteroatom containing, in A, D-parts optionally substituted cyclic group; G : H, carboxy group of formula (-CO-R 1>) or (-C(=L)-M-R 2>), sulfur dioxide group of formula (-SO 2-R 3>), phosphorus group of formula (-P(R 4>)(R 5>)(=L)), E or (-C(=L)-N(R 6>)(R 7>)); E : an equivalent metal ion or an ammonium ion; L, M : O or S; R 1>optionally halo substituted alkyl, alkenyl, alkoxyalkyl, alkylthioalkyl or polyalkoxyalkyl, optionally halo-, alkyl- or alkoxy substituted cycloalkyl, which is interrupted by at least a heteroatom, optionally substituted phenyl, phenylalkyl, hetaryl, phenoxyalkyl or hetaryloxyalkyl; R 2>optionally halo substituted alkyl, alkenyl, alkoxyalkyl or polyalkoxyalkyl, optionally substituted cycloalkyl, phenyl or benzyl; R 3>-R 5>optionally halo substituted alkyl, alkoxy, alkylamino, dialkylamino, alkylthio, alkenylthio or cycloalkylthio, or optionally substituted phenyl, benzyl, phenoxy or phenylthio; and either R 6>, R 7>optionally halo substituted alkyl, cycloalkyl, alkenyl, alkoxy or alkoxyalkyl, optionally substituted phenyl or benzyl, or H; or NR 6>R 7>cyclic group interrupted optionally by O or S. Independent claims are included for: (1) the preparation of (I); (2) the preparation of an agent to combat parasite and / or undesirable plant growth comprising mixing (I) with a diluent and / or a surface active material; (3) an agent comprising an active agent combination containing (I), at least a compound, which improves the compatibility of cultured plants, e.g. 4-dichloroacetyl-1-oxa-4-aza-spiro[4.5]-decane, 1-dichloroacetyl-hexahydro-3,3,8a-trimethylpyrrolo[1,2-a]-pyrimidin-6 (2H)-one, 4-dichloroacetyl-3,4-dihydro-3-methyl-2H-1,4-benzoxazine, 5-chloro-quinolin-8-oxy-acetic acid-(1-methyl-hexylester), 3-(2-chloro-benzyl)-1-(1-methyl-1-phenyl-ethyl)-urea, alpha -(cyanomethoxyimino)-phenylacetonitrile, diethyl-1-(2,4-dichloro-phen yl)-4,5-dihydro-5-methyl-1H-pyrazol-3,5-dicarboxylate, 2-dichloromethyl-2-methyl-1,3-dioxolane, 2-propenyl-1-oxa-4-azaspiro[ 4.5]decane-4-carbodithioate, 1,8-naphthalic acid anhydride, 1-(2,4-dichloro-phenyl)-5-methyl-1H-pyrazol-3-carboxylic acid-ethylester, 1-(2,4-dichloro-phenyl)-5-isopropyl-1H-pyrazol-3-car boxylic acid-ethylester, 5-chloro-quinolin-8-oxy-acetic acid-1-allyloxy-prop-2-yl-ester, 5-chloro-quinoxalin-8-oxy-acetic acid-methylester, 5-chloro-quinolin-8-oxy-acetic acid-ethylester, 5-chloro-quinoxalin-8-oxy-acetic acid-allylester, 5-chloro-quinolin-8-oxy-acetic acid-2-oxo-prop-1-yl-ester, 5-chloro-quinolin-8-oxy-malonic acid-diethylester, carboxyamide compound of formula (R 1> 6>-CO-N(R 1> 7>)(R 1> 8>)), or a phenyl compound of formula (IId) or (IIe); (4) an N-acylamino acid ester compound of formula (II); (5) a phenyl compound of formula (XV), (XIV) or (XIX); and (6) a phenyl-acetic acid compound of formula (XVII). Either R 1> 7>H, or F, Cl and / or Br substituted 1-6C alkyl, 2-6C alkenyl or 2-6C alkynyl, 1-4C alkoxy-1-4C alkyl, dioxolanyl-1-4C alkyl, furyl, furyl-1-4C alkyl, thienyl, thiazolyl, piperidinyl, or optionally F, Cl and / or Br or 1-4C alkyl substituted phenyl; and R 1> 8>H, optionally F, Cl and / or Br substituted 1-6C alkyl, 2-6C alkenyl or 2-6C alkynyl, 1-4C alkoxy-1-4C alkyl, dioxolanyl-1-4C alkyl, furyl, furyl-1-4C alkyl, thienyl, thiazolyl, piperidinyl, or optionally F, Cl and / or Br or 1-4C alkyl substituted phenyl; or R 1> 7>R 1> 8>optionally 1-4C alkyl substituted phenyl, furyl or annealed benzene ring; or CR 1> 7>R 1> 8>5- or 6-membered carbocyclic (substituted by 3-6C alkandiyl or 2-5C oxaalkandiyl); either R 2> 5>H, optionally cyano, OH, halogen or 1-4C alkoxy substituted 1-6C alkyl, optionally cyano or halo substituted 3-6C alkenyl or 3-6C alkynyl, optionally cyano, halogen or 1-4C alkyl substituted 3-6C cycloalkyl; and R 2> 6>R 2> 5>, optionally nitro, cyano, halo, 1-4C alkyl, 1-4C haloalkyl, 1-4C alkoxy or 1-4C haloalkoxy substituted phenyl; or R 2> 6>R 2> 5>2-6C alkandiyl (substituted optionally with 1-4C alkyl or 2-5C oxaalkandiyl); and R 1> 6>F, Cl and / or Br substituted 1-4C alkyl. [Image] [Image] [Image] [Image] - ACTIVITY : Antiparasitic; Herbicide; Insecticide; Arachnicide; Anthelmintic; Nematocide. - MECHANISM OF ACTION : None given.
Description
[0001] This application is a divisional application of Chinese patent application No. 200780048041.6 filed on October 13, 2007. technical field [0002] The present invention relates to novel trifluoromethoxyphenyl substituted tetramic acid derivatives, various preparation methods thereof and their use as insecticides and / or herbicides. The invention also provides selective herbicidal compositions which firstly contain trifluoromethoxyphenyl-substituted tetramic acid derivatives and secondly a compound which improves crop plant compatibility. [0003] The invention also relates to the enhancement of the action of crop protection compositions having tetramic acid derivatives containing trifluoromethoxyphenyl substitutions by adding ammonium or phosphonium salts and optionally penetrants; Corresponding compositions; to processes for their preparation and to their use in crop protection as insecticides and / or acaricides and / or for preventing unwanted vegetation. Background tech...
Claims
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