| Fungicidal mixtures based on morpholine or piperidine derivatives and oxime ether derivatives -> Monitor Keywords |
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Fungicidal mixtures based on morpholine or piperidine derivatives and oxime ether derivativesRelated Patent Categories: Drug, Bio-affecting And Body Treating Compositions, Designated Organic Active Ingredient Containing (doai), Heterocyclic Carbon Compounds Containing A Hetero Ring Having Chalcogen (i.e., O,s,se Or Te) Or Nitrogen As The Only Ring Hetero Atoms Doai, Hetero Ring Is Six-membered And Includes At Least Nitrogen And Oxygen As Ring Hetero Atoms (e.g., Monocyclic 1,2- And 1,3-oxazines, Etc.), Morpholines (i.e., Fully Hydrogenated 1,4- Oxazines)Fungicidal mixtures based on morpholine or piperidine derivatives and oxime ether derivatives description/claimsThe Patent Description & Claims data below is from USPTO Patent Application 20060154924, Fungicidal mixtures based on morpholine or piperidine derivatives and oxime ether derivatives. Brief Patent Description - Full Patent Description - Patent Application Claims
[0001] The present invention relates to fungicidal mixtures for controlling harmful fungi and to methods for controlling harmful fungi using such mixtures. [0002] WO 97/40673 provides fungicidal mixtures which, inter alia, comprise active compounds of the formulae Ia, Ib and/or Ic in addition to other fungicidally active compounds from the group of the oxime ethers and/or the carbamates. [0003] Other fungicidal mixtures which comprise active compounds of the formulae Ia to Ic are disclosed in EP-A 797386, WO 97/06681, EP-B 425857, EP-B 524496, EP-A 690792, WO 94/22308 and EP-B 645087. [0004] Brighton Crop Protection Conference 1996, Pests and Diseases, pp. 47-52 discloses the active compound of the formula Id: [0005] DE 19722223 describes mixtures of compounds of the formula II and of active compounds from the class of the strobilurins. [0006] It is an object of the present invention to provide other particularly effective mixtures for controlling harmful fungi and, in particular, for certain indications. [0007] We have found that this object is surprisingly achieved with a mixture which, as active compounds, comprises morpholine or piperidine derivatives of the formula I defined at the outset and, as further fungicidally active component, at least one fungicidally active compound of the formula II where the substituents X.sup.1 to X.sup.5 and R.sup.1 to R.sup.4 are as defined below: [0008] X.sup.1 is C.sub.1-C.sub.4-haloalkyl, C.sub.1-C.sub.4-haloalkoxy or halogen [0009] X.sup.2 to X.sup.5 are, independently of one another, hydrogen, halogen, C.sub.1-C.sub.4-alkyl, C.sub.1-C.sub.4-haloalkyl, C.sub.1-C.sub.4-alkoxy or C.sub.1-C.sub.4-haloalkoxy; [0010] R.sup.1 is C.sub.1-C.sub.4-alkyl, C.sub.2-C.sub.6-alkenyl, C.sub.2-C.sub.6-alkynyl, C.sub.1-C.sub.4-alkyl-C.sub.3-C.sub.7-cycloalkyl, where these radicals may carry substituents selected from the group consisting of halogen, cyano and C.sub.1-C.sub.4-alkoxy, [0011] R.sup.2 is a phenyl radical or a 5- or 6-membered saturated or unsaturated heterocyclyl radical having at least one heteroatom selected from the group consisting of N, O and S, where the cyclic radicals may have one to three substituents selected from the group consisting of halogen, C.sub.1-C.sub.4-alkyl, C.sub.1-C.sub.4-alkoxy, C.sub.1-C.sub.4-haloalkyl, C.sub.1-C.sub.4-haloalkoxy, C.sub.1-C.sub.4-alkoxy-C.sub.2-C.sub.4-alkenyl, C.sub.1-C.sub.4-alkoxy-C.sub.2-C.sub.4-alkynyl, [0012] R.sup.3 and R.sup.4 are, independently of one another, hydrogen, C.sub.1-C.sub.4-alkyl, C.sub.1-C.sub.4-alkoxy, C.sub.1-C.sub.4-alkylthio, N-C.sub.1-C.sub.4-alkylamino, C.sub.1-C.sub.4-haloalkyl or C.sub.1-C.sub.4-haloalkoxy [0013] in a synergistically effective amount. [0014] The mixtures according to the invention act synergistically, and they are therefore particularly Suitable for controlling harmful fungi and, in particular, powdery mildew fungi. [0015] In the context of the present invention, halogen is fluorine, chlorine, bromine and iodine and in particular fluorine, chlorine and bromine. [0016] The term "alkyl" includes straight-chain and branched alkyl groups. These are preferably straight-chain or branched C.sub.1-C.sub.12-alkyl groups and in particular C.sub.1-C.sub.6-alkyl groups. Examples of alkyl groups are alkyl, such as, in particular, methyl, ethyl, propyl, 1-methylethyl, butyl, 1-methylpropyl, 2-methylpropyl [lacuna] 1,1-dimethylethyl, n-pentyl, 1-methylbutyl, 2-methylbutyl, 3-methylbutyl, 1,2-dimethylpropyl, 1,1-dimethylpropyl, 2,2-dimethylpropyl, 1-ethylpropyl, n-hexyl, 1-methylpentyl, 2-methylpentyl, 3-methylpentyl, 4-methylpentyl, 1,2-dimethylbutyl, 1,3-dimethylbutyl, 2,3-dimethylbutyl, 1,1-dimethylbutyl, 2,2-dimethylbutyl, 3,3-dimethylbutyl, 1,1,2-trimethylpropyl, 1,2,2-trimethylpropyl, 1-ethylbutyl, 2-ethylbutyl, 1-ethyl-2-methylpropyl, n-heptyl, 1-methylhexyl, 1-ethylpentyl, 2-ethylpentyl, 1-propylbutyl, octyl, decyl, dodecyl. [0017] Haloalkyl is an alkyl group which is defined as above and is partially or fully halogenated by one or more halogen atoms, in particular by fluorine and chlorine. Preferably, there are 1 to 3 halogen atoms present, and particular preference is given to the difluoromethane [sic) and the trifluoromethyl group. [0018] The alkenyl group includes straight-chain and branched C.sub.2-C.sub.6-alkenyl groups. Examples of alkenyl groups are 2-propenyl, 2-butenyl, 3-butenyl, 1-methyl-2-propenyl, 2-methyl-2-propenyl, 2-pentenyl, 3-pentenyl, 4-pentenyl, 1-methyl-2-butenyl, 2-methyl-2-butenyl, 3-methyl-2-butenyl, 1-methyl-3-butenyl, 2-methyl-3-butenyl, 3-methyl-3-butenyl, 1,1-dimethyl-2-propenyl, 1,2-dimethyl-2-propenyl, 1-ethyl-2-propenyl, 2-hexenyl, 3-hexenyl, 4-hexenyl, 5-hexenyl, 1-methyl-2-pentenyl, 2-methyl-2-pentenyl, 3-methyl-2-pentenyl, 4-methyl-2-pentenyl, 1-methyl-3-pentenyl, 2-methyl-3-pentenyl, 3-methyl-3-pentenyl, 4-methyl-3-pentenyl, 1-methyl-4-pentenyl, 2-methyl-4-pentenyl, 3-methyl-4-pentenyl, 4-methyl-4-pentenyl, 1,1-dimethyl-2-butenyl, 1,1-dimethyl-3-butenyl, 1,1-dimethyl-3-butenyl, 1,2-dimethyl-2-butenyl, 1,2-dimethyl-3-butenyl, 1,3-dimethyl-2-butenyl, 1,3-dimethyl-3-butenyl, 2,2-dimethyl-3-butenyl, 2,3-dimethyl-2-butenyl, 2,3-dimethyl-3-butenyl, 1-ethyl-2-butenyl, 1-ethyl-3-butenyl, 2-ethyl-2-butenyl, 2-ethyl-3-butenyl, 1,1,2-trimethyl-2-propenyl, 1-ethyl-1-methyl-2-propenyl and 1-ethyl-2-methyl-2-propenyl, in particular 2-propenyl, 2-butenyl, 3-methyl-2-butenyl and 3-methyl-2-pentenyl. [0019] The alkenyl group may be partially or fully halogenated by one or more halogen atoms, in particular by fluorine and chlorine. It has preferably 1 to 3 halogen atoms. [0020] The alkynyl group includes straight-chain and branched C.sub.3-C.sub.6-alkynyl groups. Examples of alkynyl groups are 2-propynyl, 2-butynyl, 3-butynyl, 1-methyl-2-propynyl, 2-pentynyl, 3-pentynyl, 4-pentynyl, 1-methyl-3-butynyl, 2-methyl-3-butynyl, 1-methyl-2-butynyl, 1,1-dimethyl-2-propynyl, 1-ethyl-2-propynyl, 2-hexynyl, 3-hexynyl, 4-alkynyl, 5-hexynyl, 1-methyl-2-pentynyl, 1-methyl-3-pentynyl, 1-methyl-4-pentynyl, 2-methyl-3-pentynyl, 2-methyl-4-pentynyl, 3-methyl-4-pentynyl, 4-methyl-2-pentynyl, 1,2-dimethyl-2-butynyl, 1,1-dimethyl-3-butynyl, 1,2-dimethyl-3-butynyl, 2,2-dimethyl-3-butynyl, 1-ethyl-2-butynyl, 1-ethyl-3-butynyl, 2-ethyl-3-butynyl and 1-ethyl-1-methyl-2-propynyl. [0021] The C.sub.1-C.sub.4-alkylene-C.sub.3-C.sub.7-cycloalkyl group is a C.sub.3-C.sub.7-cycloalkyl group, such as cyclopropyl, cyclobutyl, cyclopentyl or cyclohexyl, which is attached via a C.sub.1-C.sub.4-alkylene radical. [0022] Suitable substituents R.sup.2 are, in addition to phenyl (unsubstituted or substituted), in particular thienyl, pyrazolyl, pyrrolyl, imidazolyl, thiazolyl, furyl, pyridazinyl and pyrimidinyl. Preferred substituents at these ring systems are halogen (in particular F and Cl), C.sub.1-C.sub.4-alkoxy (in particular methoxy) and C.sub.1-C.sub.4-alkyl (in particular methyl, ethyl). The number of the ring substituents can be from 1 to 3 and is in particular 1 or 2. Particular preference is given to phenyl or substituted phenyl, thienyl, thienyl-C.sub.1-C.sub.4-alkyl, pyrazolyl and pyrazol-C.sub.1-C.sub.4-alkyl. [0023] The substituents R.sup.3 and R.sup.4 are C.sub.1-C.sub.4-alkyl, C.sub.1-C.sub.4-alkoxy, C.sub.1-C.sub.4-alkylthio, N-C.sub.1-C.sub.4-alkylamino, C.sub.1-C.sub.4-haloalkyl or C.sub.1-C.sub.4-haloalkoxy. Preferred substituents R.sup.3 and R.sup.4 are hydrogen, F, Cl, methyl, ethyl, methoxy, thiomethyl and N-methylamino. R.sup.3 and R.sup.4 together may also form a grouping .dbd.O. [0024] The morpholine or piperidine derivatives I (Ia: common name: Fenpropimorph, U.S. Pat. No. 4,202,894; Ib: common name: Fenpropidin, U.S. Pat. No. 4,202,894; Ic: common name: Tridemorph, DE-A 11 64 152), their preparation and their action against harmful fungi are known, and they are commercially available products. [0025] The compounds of the formula II and processes for their preparation are described in WO-A 96/19442 and in the earlier applications DE 1 97 41098.7 and 1 97 41099.5. [0026] Among the compounds of the formula II, preference is given to those where X.sup.1 is a C.sub.1-C.sub.4-haloalkyl, in particular a trifluoromethyl group, a C.sub.1-C.sub.4-haloalkoxy, in particular a difluoromethoxy or trifluoromethoxy group or a halogen, in particular chlorine and X.sup.2 and X.sup.3 are a hydrogen atom or a halogen group, in particular a hydrogen atom. X.sup.4 and X.sup.5 are preferably hydrogen, halogen (in particular Cl or F), C.sub.1-C.sub.4-alkoxy (in particular methoxy or ethoxy), C.sub.1-C.sub.4-haloalkyl (in particular trifluoromethyl) or C.sub.1-C.sub.4-haloalkoxy (in particular trifluoromethoxy). [0027] Preferred substituents R.sup.1 are C.sub.1-C.sub.4-alkyl (methyl, ethyl, n- and isopropyl and t-butyl), C.sub.1-C.sub.4-alkylene-C.sub.3-C.sub.7-cycloalkyl, C.sub.1-C.sub.4-alkenyl (in particular ethenyl, propenyl and butenyl, which may be substituted, in particular by halogen (preferably Cl)), propynyl, cyanomethyl and methoxymethyl. Among the C.sub.1-C.sub.4-alkylene-C.sub.3-C.sub.7-cycloalkyl substituents, methylene-substituted compounds, in particular methylenecyclopropyl, methylenecyclopentyl, methylenecyclohexyl and methylenecyclohexenyl, are particularly preferred. The rings in these substituents may be substituted, preferably by halogen. [0028] Suitable substituents R.sup.2 are, in addition to phenyl (unsubstituted or substituted), in particular thienyl, pyrazolyl, pyrrolyl, imidazolyl, thiazolyl, furyl, pyridazinyl and pyrimidinyl. Preferred substituents at these ring systems are halogen (in particular F and Cl), C.sub.1-C.sub.4-alkoxy (in particular methoxy) and C.sub.1-C.sub.4-alkyl (in particular methyl, ethyl). The number of the ring substituents can be from 1 to 3 and is in particular 1 or 2. Particular preference is given to phenyl or substituted phenyl. [0029] Preferred compounds of the formula II are shown in the tables of WO 96/019442, which has already been mentioned. Among these compounds, in turn, particular preference is given to the compounds listed in Table 1 below (R.sup.3 and R.sup.4 are each hydrogen). TABLE-US-00001 TABLE 1 No. X.sup.1 X.sup.2 X.sup.3 X.sup.4 X.sup.5 R.sup.1 R.sup.2 II.1 CF.sub.3 H H H H ethyl Ph-4-OMe II.2 CF.sub.3 H H H H methyl Ph-4-OMe II.3 CF.sub.3 H H H H --CH.sub.2-cPr 2-thienyl II.4 CF.sub.3 H H H H --CH.sub.2-cPr 3-thienyl II.5 CF.sub.3 H H H H --CH.sub.2-cPr Ph-2,4-F.sub.2 II.6 CF.sub.3 H H H H --CH.sub.2-cPr Ph-2-F II.7 CF.sub.3 H H H H --CH.sub.2-cPr Ph-2-F-4-OMe II.8 CF.sub.3 H H H H --CH.sub.2-cPr Ph-3-Me II.9 CF.sub.3 H H H H --CH.sub.2-cPr Ph-3-Me-4-OMe II.10 CF.sub.3 H H H H --CH.sub.2-cPr Ph-4-F II.11 CF.sub.3 H H H H --CH.sub.2-cPr Ph-4-Me II.12 CF.sub.3 H H H H --CH.sub.2-cPr Ph-4-OMe II.13 CF.sub.3 H H H H --CH.sub.2-cPr Ph II.14 CF.sub.3 H H H H --CH.sub.2--CH.dbd.CH.sub.2 Ph II.15 CF.sub.3 H H H H --CH.sub.2--CH.dbd.CH.sub.2 Ph-4-OMe II.16 CF.sub.3 H H H H --CH.sub.2--CH.dbd.CCl.sub.2 Ph-4-OMe II.17 CF.sub.3 H H H F --CH.sub.2--CH.sub.3 Ph-4-OMe II.18 CF.sub.3 H H H F --CH.sub.2CH.sub.3 Ph II.19 CF.sub.3 H H H F --CH.sub.3 Ph-4-OMe II.20 CF.sub.3 H H H F --CH.sub.2-cPr Ph II.21 CF.sub.3 H H H F --CH.sub.2-cPr Ph-2-F II.22 CF.sub.3 H H H F --CH.sub.2-cPr Ph-2,4-F.sub.2 II.23 CF.sub.3 H H H F --CH.sub.2-cPr Ph-2-F-3-Me II.24 CF.sub.3 H H H F --CH.sub.2-cPr Ph-2-F-4-OMe II.25 CF.sub.3 H H H F --CH.sub.2-cPr Ph-3,5-Me.sub.2 II.26 CF.sub.3 H H H F --CH.sub.2-cPr 3-methylpyrazol-1-yl II.27 CF.sub.3 H H H F --CH.sub.2-cPr 3-methyl-2-thienyl II.28 CF.sub.3 H H H F --CH.sub.2-cPr 2-thienyl II.29 CF.sub.3 H H H F --CH.sub.2-cPr 3-thienyl II.30 CF.sub.3 H H H F --CH.sub.2--CHF.sub.2 Ph-4-OMe II.31 CF.sub.3 H H H F --CH.sub.2--OCH.sub.3 Ph-4-OMe II.32 CF.sub.3 H H H F --CH.sub.2--OCH.sub.3 Ph II.33 CF.sub.3 H H H F --CH.sub.2CN Ph-4-Ome II.34 CF.sub.3 H H H F --CH.sub.2CN Ph II.35 CF.sub.3 H H H F --CH.sub.2--C.dbd.CH Ph II.36 CF.sub.3 H H H F --CH.sub.2--C.dbd.CH Ph-4-OMe II.37 CF.sub.3 H H H F --CH.sub.2--C.dbd.CH Ph-2-F II.38 CF.sub.3 H H H F --CH.sub.2--C.dbd.CH Ph-4-Me II.39 CF.sub.3 H H H F --CH.sub.2--C.dbd.CH 2-thienyl II.40 CF.sub.3 H H H F --CH.sub.2--C.dbd.CH Ph-2-F-4-OMe II.41 CF.sub.3 H H H F i-propyl Ph II.42 CF.sub.3 H H H F n-butyl Ph II.43 CF.sub.3 H H H F n-propyl Ph II.44 CF.sub.3 H H H F t-butyl Ph II.45 CF.sub.3 H H H Cl --CH.sub.3 II.46 CF.sub.3 H H H Cl --CH.sub.2CN Ph-4-OMe II.47 CF.sub.3 H H H Cl --CH.sub.2--OMe Ph-4-OMe II.48 CF.sub.3 H H H Cl --CH.sub.2-cPr Ph II.49 CF.sub.3 H H H Cl --CH.sub.2-cPr 3-methylpyrazol-1-yl II.50 CF.sub.3 H H H Cl --CH.sub.2-cPr 2-thienyl II.51 CF.sub.3 H H H Cl --CH.sub.2-cPr Ph-2,4-F.sub.2 II.52 CF.sub.3 H H H Cl --CH.sub.2--C.dbd.CH Ph-4-OMe II.53 CF.sub.3 H H H CF.sub.3 --CH.sub.3 Ph-4-OMe II.54 CF.sub.3 H H H CF.sub.3 --CH.sub.2CH.sub.2Cl Ph-4-OMe II.55 CF.sub.3 H H H CF.sub.3 --CH.sub.2-cPr 2-thienyl II.56 CF.sub.3 H H H CF.sub.3 --CH.sub.2-cPr Ph-2-F-5-Me II.57 CF.sub.3 H H H CF.sub.3 --CH.sub.2-cPr Ph-4-OMe II.58 CF.sub.3 H H H CF.sub.3 --CH.sub.2-cPr Ph II.59 CF.sub.3 H H H OCH.sub.3 --CH.sub.2CH.sub.3 Ph-4-OMe II.60 CF.sub.3 H H H OCH.sub.3 --CH.sub.2-cPr Ph-4-OMe II.61 CF.sub.3 H H H OCH.sub.3 --CH.sub.2-cPr Ph II.62 CF.sub.3 H H Cl F --CH.sub.2--CH.sub.2Cl Ph II.63 CF.sub.3 H H Cl F --CH.sub.2--CH.dbd.CH.sub.2 Ph-4-OMe II.64 CF.sub.3 H H Cl F --CH.sub.2-cPr 2-thienyl II.65 CF.sub.3 H H Cl F --CH.sub.2-cPr Ph-2-F II.66 CF.sub.3 H H Cl F --CH.sub.2-cPr Ph II.67 CF.sub.3 H H Cl F --CH.sub.2-cPr Ph-2-F-5-Me II.68 CF.sub.3 H H Cl Cl --CH.sub.2--CH.dbd.CH.sub.2 Ph-4-OMe II.69 CF.sub.3 H H Cl Cl --CH.sub.2CH.sub.2Cl Ph II.70 CF.sub.3 H H Cl Cl --CH.sub.2CH.sub.3 Ph-2-F-5-Me II.71 CF.sub.3 H H Cl Cl --CH.sub.2-cPr Ph-3,5-Me.sub.2 II.72 CF.sub.3 H H SCH.sub.3 F --CH.sub.2-cPr Ph-4-OMe II.73 CF.sub.3 H H OCH.sub.3 F --CH.sub.2-cPr Ph-4-OMe II.74 CF.sub.3 H F H H --CH.sub.2-cPr Ph II.75 CF.sub.3 H F H H --CH.sub.2--CH.sub.3 Ph-4-OMe II.76 CF.sub.3 H H F F --CH.sub.2CH.sub.3 Ph II.77 CF.sub.3 H H F F --CH.sub.2--CH.sub.2Cl Ph-2-F-5-Me II.78 CF.sub.3 H H F F --CH.sub.2--OCH.sub.3 Ph-4-OMe II.79 CF.sub.3 H H F F --CH.sub.2-cPr Ph II.80 CF.sub.3 H H F F --CH.sub.2-cPr 3-methylpyrazol-1-yl II.81 CF.sub.3 H H F F --CH.sub.2-cPr 3-methyl-2-thienyl II.82 CF.sub.3 H H F F --CH.sub.2-cPr Ph-2-F-3-Me II.83 CF.sub.3 H H F F --CH.sub.2-cPr Ph-2-F-4-OMe II.84 CF.sub.3 H H F F --CH.sub.2-cPr Ph-2-F-5-Me II.85 CF.sub.3 H H F F --CH.sub.2-cPr Ph-4-OMe II.86 CF.sub.3 H H F F --CH.sub.2-cPr Ph-4F II.87 CF.sub.3 H H F F i-propyl Ph-4-OMe II.88 CF.sub.3 H H F F n-butyl Ph-4-OMe II.89 CF.sub.3 H H F F --CH.sub.2--C.dbd.CH Ph-4-OMe II.90 CF.sub.3 H H CF.sub.3 F --CH.sub.3 Ph-4-OMe II.91 CF.sub.3 H H CF.sub.3 F --CH.sub.2--CH.dbd.CH.sub.2 Ph II.92 CF.sub.3 H H CF.sub.3 F --CH.sub.2-cPr Ph II.93 CF.sub.3 H H Cl Cl --CH.sub.2-cHxe-3 Ph II.94 CF.sub.3 H H F H --CH.sub.2-cPr Ph-4-F II.95 CF.sub.3 H H Cl Cl --CH.sub.2-cHex Ph II.96 CF.sub.3 H H H F --CH.sub.2--SCH.sub.3 Ph II.97 CF.sub.3 H H H F --CH.sub.2--SOCH.sub.3 Ph II.98 CF.sub.3 H H H F --CH.sub.2--SO.sub.2CH.sub.3 Ph II.99 CF.sub.3 H H H F --CH.sub.2--NHMe Ph II.100 CF.sub.3 H H H F CH.sub.2--CONH.sub.2 Ph II.101 CF.sub.3 H H H F CH.sub.2CON(CH.sub.3).sub.2 Ph [0030] In the table above, cPr is cyclopropyl, cHxe-n is cyclohexenyl which is unsaturated in position n, c-Hex is cyclohexyl and Ph is phenyl. 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