# Patent

## Title
Pyridinecarboxamides, useful-plant-protecting composition comprising them and processes for their preparation and their use

## Abstract

Compounds of the formula (I), or salts thereof,




in which R1 to R4 are as defined in formula (I) of claim 1 are suitable as useful-plant-protecting agents for reducing or preventing harmful effects of agrochemicals on the useful plants and their method of preparation are described.

## Background
INCORPORATION BY REFERENCE
The present application is a continuation of U.S. patent application Ser. No. 12/111,419 filed Apr. 29, 2008, which claims benefit under 35 U.S.C. 119(a) of European patent application 07400013.4, filed on Apr. 30, 2007.


Any foregoing applications, including U.S. patent application Ser. No. 12/111,419 and European patent application EP 07400013.4, and all documents cited therein or during their prosecution (“application cited documents”) and all documents cited or referenced in the application cited documents, and all documents cited or referenced herein (“herein cited documents”), and all documents cited or referenced in herein cited documents, together with any manufacturer's instructions, descriptions, product specifications, and product sheets for any products mentioned herein or in any document incorporated by reference herein, are hereby incorporated herein by reference, and may be employed in the practice of the invention.


DESCRIPTION
The present invention relates to useful-plant-protecting compounds and compositions comprising specific compounds as safeners for reducing phytotoxic actions of agrochemicals, in particular of herbicides. The invention relates in particular to pyridone derivatives as safeners and to processes for their preparation.
When controlling unwanted organisms in crops of plants which are useful for agriculture or forestry by using pesticides, the useful plants are frequently also damaged to a greater or lesser extent, by the pesticides employed. This unwanted phytotoxic effect is encountered in particular with the use of a considerable number of herbicides in crops of useful plants such as, for example, corn, rice or cereals- and there primarily in the post-emergence application. In some instances, the useful plants can be protected against the phytotoxic properties of the pesticides by employing safeners or antidotes, without diminishing or substantially impairing the pesticidal activity against the harmful organisms. In some cases, even an improved pesticidal action against harmful organisms such as weeds was observed.
The compounds hitherto known as safeners belong to a large number of different chemical structure classes, their suitability as safeners generally also depending on the chemical structures of the pesticides and on the crops of useful plants.
Known for a long time have been the safener actions of compounds from the group of the phenoxy- or heteroaryloxyalkanecarboxylic acids, provided these compounds are applied in combination with herbicides. Examples of such compounds are MCPA and similar compounds which are at the same time herbicidally active against harmful plants, or cloquintocet-mexyl.
Known are furthermore safeners from the group of the derivatives of N-phenyl-substituted heteroaromatic carboxylic esters having a plurality of heteroatoms in the heterocycle. Examples of such safeners are the safeners mefenpyr-diethyl and isoxadifen-ethyl, which are used in commercial products.
WO 2004/084631 (us 2004-0224844) discloses the use of hydroxyl-substituted aromatic carboxylic acid derivatives. WO 2005/015994 (US 2005-037922) describes specific derivatives of salicylic acid as safeners. These compounds are suitable in particular for use as safeners in crops of corn and soybeans.
Furthermore, WO 2005/112630 (US 2005-256000) discloses 1,2-dihydroquinoxalin-2-one derivatives as safeners.
Active compounds from the chemical class of the pyridones with pesticidal properties are known from the literature. Various biological actions are described; thus, for example, WO 2001/014339 (US 2002-177578) describes the fungicidal action of certain substituted pyridonecarboxamides, WO 2005/042492 (US 2007-196406) and WO 2005/042493 (US 2007-037858) describe inter alia the fungicidal action of heterocyclylcarboxanilides. EP-A-544151 (U.S. Pat. No. 5,344,813) describes the action of hydroxyl-substituted pyridonecarboxamides as herbicides.
Also known are representatives having pharmacological properties. Thus, WO 2001/055115 (U.S. Pat. No. 6,794,397) describes nicotinanilides as inductors of apoptosis, and US 2004/0116479 describes dialkylnicotinamides as inhibitors of angiogenesis.
Furthermore, EP-A-522392 (U.S. Pat. No. 5,235,060) describes 6-trifluoromethyl-substituted pyridonecarboxamides as precursors for the synthesis of herbicidally active sulfonylureas. Helv. Chim. Acta 71 (1988) 596-601 and GB 2305174 mention 1,2-dihydro-2-oxo-6-trifluoromethylpyridine-3-carboxamide, 6-chloro(difluoro)methyl-1,2-dihydro-2-oxopyridine-3-carboxamide and 6-difluoromethyl-1,2-dihydro-2-oxopyridine-3-carboxamide as intermediates in the synthesis of pyranopyridines. WO 2007/041052 mentions 1,2-dihydro-2-oxo-6-trifluoromethylpyridine-3-carboxamide as an intermediate in the synthesis of pharmacologically active spiropiperidines.
The use of such compounds as safeners in combination with certain pesticides has hitherto not been disclosed.
WO 2006/007981 (US 2007-265164) describes a method for identifying compounds which induce the defense of plants against pathogens, where the increase of the expression of plant-endogenous genes is considered to be an indication for the induction.
Here, 1,2-dihydro-2-oxo-6-trifluoromethylpyridine-3-carboxamide is mentioned as part of a group of six compounds which may be referred to as safeners. A safener action confirmed by biological tests on plants has hitherto not been disclosed for this compound, and is also not sufficiently disclosed by WO 2006/007981.
In particular the expression values obtained according to WO 2006/007981 for the compound, which in some cases are at a considerably lower level than those for commercially available safeners also mentioned, lead it to be expected in the best case that, as safeners, they are considerably less suitable, if at all.
When safeners were used to protect useful plants against damage by pesticides, it was found that the known safeners may in many cases have disadvantages. These include:

    
    
        the safener reduces the efficacy of the pesticides, in particular that of herbicides, against the harmful plants,
        the useful-plant-protecting properties are insufficient,
        in combination with a certain herbicide, the spectrum of the useful plants in which the safener/herbicide is to be employed is not sufficiently wide,
        a certain safener can only be combined with a small number of herbicides,
        by using safeners, the application rate to be applied and the amount of formulation is increased, which may cause problems during the application.
    
    


For the reasons mentioned, there is a need to provide alternative compounds having safener action.
The invention provides the use of compounds of the formula (I) or salts thereof




in which

    R1 is a (C1-C6)-haloalkyl radical, preferably a radical of the formula CF3, CF2Cl, CF2H, CF2CF3, CF2CF2H, CF2CF2Cl, CFClCF3, CFHCF3, CF(CF3)2, CH(CF3)2, CF2CF2CF3, or C(CH3)2F and
    R2 is hydrogen or halogen and
    R3 is hydrogen, (C1-C16)-alkyl, (C2-C16-alkenyl or (C2-C16)-alkynyl,
    
        where each of the 3 lastmentioned radicals is unsubstituted or substituted by one or more radicals selected from the group consisting of halogen, hydroxyl, cyano, (C1-C4)-alkoxy, (C1-C4)-haloalkoxy, (C1-C4)-alkylthio, (C1-C4)-alkylamino, di[(C1-C4)-alkyl]amino, [(C1-C4)-alkoxy]-carbonyl, [(C1-C4)-haloalkoxy]-carbonyl, (C3-C6)-cycloalkyl, which is unsubstituted or substituted, phenyl, which is unsubstituted or substituted, and heterocyclyl, which is unsubstituted or substituted,
        or (C3-C6)-cycloalkyl, (C4-C6)-cycloalkenyl, (C3-C6)-cycloalkyl which is condensed at one side of the ring to a 4- to 6-membered saturated or unsaturated carbocyclic ring, or (C4-C6)-cycloalkenyl which is condensed at one side of the ring to a 4- to 6-membered saturated or unsaturated carbocyclic ring,
        where each of the 4 lastmentioned radicals is unsubstituted or substituted by one or more radicals selected from the group consisting of halogen, hydroxyl, cyano, (C1-C4)-alkyl, (C1-C4)-haloalkyl, (C1-C4)-alkoxy, (C1-C4)-haloalkoxy, (C1-C4)-alkylthio, (C1-C4)-alkylamino, di[(C1-C4)-alkyl]amino, [(C1-C4)-alkoxy]-carbonyl, [(C1-C4)-haloalkoxy]-carbonyl, (C3-C6)-cycloalkyl, which is unsubstituted or substituted, phenyl, which is unsubstituted or substituted, and heterocyclyl, which is unsubstituted or substituted,
        and
    
    
    R4 is (C1-C16)-alkyl, (C2-C16)-alkenyl or (C2-C16)-alkynyl,
    
        where each of the 3 lastmentioned radicals is unsubstituted or substituted by one or more radicals selected from the group consisting of halogen, hydroxyl, cyano, (C1-C4)-alkoxy, (C1-C4)-haloalkoxy, (C1-C4)-alkylthio, (C1-C4)-alkylamino, di[(C1-C4)-alkyl]-amino, [(C1-C4)-alkoxy]-carbonyl, [(C1-C4)-haloalkoxy]-carbonyl, (C3-C6)-cycloalkyl, which is unsubstituted or substituted, phenyl, which is unsubstituted or substituted, and heterocyclyl, which is unsubstituted or substituted
        or (C3-C6)-cycloalkyl, (C4-C6)-cycloalkenyl, (C3-C6-cycloalkyl which is condensed at one side of the ring to a 4- to 6-membered saturated or unsaturated carbocyclic ring, or (C4-C6)-cycloalkenyl which is condensed at one side of the ring to a 4- to 6-membered saturated or unsaturated carbocyclic ring,
        where each of the 4 lastmentioned radicals is unsubstituted or substituted by one or more radicals selected from the group consisting of halogen, hydroxyl, cyano, (C1-C4)-alkyl, (C1-C4)-haloalkyl, (C1-C4)-alkoxy, (C1-C4)-haloalkoxy, (C1-C4)-alkylthio, (C1-C4)-alkylamino, [(C1-C4)-alkoxy]-carbonyl, [(C1-C4)-haloalkoxy]-carbonyl, (C3-C6)-cycloalkyl, which is unsubstituted or substituted, phenyl, which is unsubstituted or substituted, and heterocyclyl, which is unsubstituted or substituted,
        or
    
    
    R3 is (C1-C4)-alkoxy, (C2-C4)-alkenyloxy, (C2-C6)-alkynyloxy or (C2-C4)-haloalkoxy and
    R4 is hydrogen or (C1-C4)-alkyl or
    R3 and R4 together with the directly attached nitrogen atom are a four- to eight-membered heterocyclic ring which, in addition to the nitrogen atom, may also comprise further hetero ring atoms, preferably up to two further hetero ring atoms selected from the group consisting of N, O and S, and which is unsubstituted or substituted by one or more radicals selected from the group consisting of halogen, cyano, nitro, (C1-C4)-alkyl, (C1-C4)-haloalkyl, (C1-C4)-alkoxy, (C1-C4)-haloalkoxy and (C1-C4)-alkylthio, or
    R3 and R4 together with the directly attached nitrogen atom are the group —N═CR5—NR6R7, in which
    
        R5 is hydrogen or (C1-C6)-alkyl, with hydrogen being preferred, and
        R6, R7 independently of one another are hydrogen or (C1-C4)-alkyl, preferably (C1-C2)-alkyl, or R6 and R7 together with the directly attached nitrogen atom form a five- to seven-membered, preferably saturated heterocyclic ring, such as, for example, piperidinyl, pyrrolidinyl or morpholinyl,
        or
    
    
    R1 is a (C1-C6)-haloalkyl radical, preferably a radical of the formula CF3, CF2Cl, CF2H, CF2CF3, CF2CF2H, CF2CF2Cl, CFClCF3, CFHCF3, CF(CF3)2, CH(CF3)2, CF2CF2CF3 or C(CH3)2F, more preferably a radical of the formula CF3, CF2Cl, CF2H, CF2CF3, CF2CF2H, CF2CF2Cl, CF2CF2CF3 or C(CH3)2F, in particular CF2Cl, CF2H, CF2CF3, CF2CF2H, CF2CF2Cl, CF2CF2CF3 or C(CH3)2F, even more preferably CF2Cl, CF2H, CF2CF3, CF2CF2H, CF2CF2Cl or CF2CF2CF3,
    R2 is halogen,
    R3 is hydrogen and
    R4 is hydrogen
    
        or
    
    
    R1 is a radical of the formula CF2Cl, CF2H, CF2CF3, CF2CF2H, CF2CF2Cl, CFClCF3, CFHCF3, CF(CF3)2, CH(CF3)2, CF2CF2CF3 or C(CH3)2F, more preferably CF2Cl, CF2H, CF2CF3, CF2CF2H, CF2CF2Cl, CF2CF2CF3 or C(CH3)2F, even more preferably CF2Cl, CF2H, CF2CF3, CF2CF2H, CF2CF2Cl or CF2CF2CF3,
    R2 is hydrogen,
    R3 is hydrogen and
    R4 is hydrogen,

as a useful-plant-protecting agent for reducing or preventing harmful actions of agrochemicals, preferably pesticides, in particular herbicides, on the useful plants.



Hereinbelow, the compounds of the formula (I) and their salts are in some cases also referred to as “compounds (I)” according to the invention or used according to the invention.
The compounds of the formula (I) also include tautomers which can be formed by hydrogen shifts and whose structure is formally not embraced by the formula (I). These tautomers are nevertheless included in the definition of the compounds of the formula (I) according to the invention. The definition of the compounds of the formula (I) includes in particular the tautomeric structures of the formula (Ia) (2-hydroxypyridine-3-carboxamides) or salts thereof




in which
R1, R2, R3 and R4 are as defined in formula (I).
Some compounds of the formula (I) according to the invention or salts thereof are novel and also form part of the subject matter of the invention.
It is noted that in this disclosure and particularly in the claims and/or paragraphs, terms such as “comprises”, “comprised”, “comprising” and the like can have the meaning attributed to it in U.S. patent law, e.g., they can mean “includes”, “included”, “including”, and the like; and that terms such as “consisting essentially of” and “consists essentially of” have the meaning ascribed to them in U.S. patent law, e.g., they allow for elements not explicitly recited, but exclude elements that are found in the prior art or that affect a basic or novel characteristic of the invention.
It is further noted that the invention does not intend to encompass within the scope of the invention any previously disclosed product, process of making the product or method of using the product, which meets the written description and enablement requirements of the USPTO (35 U.S.C. 112, first paragraph) or the EPO (Article 83 of the EPC), such that applicant(s) reserve the right and hereby disclose a disclaimer of any previously described product, method of making the product or process of using the product.
The invention also provides useful-plant-protecting compositions comprising compounds of the formula (I) or salts thereof and formulation auxiliaries. The invention also provides useful-plant-protecting compositions comprising compounds of the formula (I) or salts thereof in combination with further agrochemicals, preferably pesticides, in particular herbicides, and, if appropriate, formulation auxiliaries.
Some compounds of the formula (I) are already described as intermediates for preparing active compounds, see the abovementioned GB-A-2305174 (comp. (I) in which R1═CF3, CF2Cl or CF2H and R3═R4═H). EP-A-522392, which has already been mentioned, described in a general manner inter alia compounds (I) as intermediates for preparing sulfonylureas. The safener actions of the compounds have not been described.
The invention also provides compounds of the formula (I) or salts thereof




in which

    R1 is a (C1-C6)-haloalkyl radical, preferably a radical of the formula CF3, CF2Cl, CF2H, CF2CF3, CF2CF2H, CF2CF2Cl, CFClCF3, CFHCF3, CF(CF3)2, CH(CF3)2, CF2CF2CF3 or C(CH3)2F, in particular a radical of the formula CF3, CF2Cl, CF2H, CF2CF3, CF2CF2H, CF2CF2Cl, CF2CF2CF3 or C(CH3)2F, more preferably CF3, CF2Cl, CF2H, CF2CF3, CF2CF2H, CF2CF2Cl or CF2CF2CF3 and
    R2 is hydrogen or halogen and
    R3 is hydrogen, (C1-C16)-alkyl, (C2-C16)-alkenyl or (C2-C16)-alkynyl,
    
        where each of the 3 lastmentioned radicals is unsubstituted or substituted by one or more radicals selected from the group consisting of halogen, hydroxyl, cyano, (C1-C4)-alkoxy, (C1-C4)-haloalkoxy, (C1-C4)-alkylthio, (C1-C4)-alkylamino, di[(C1-C4)-alkyl]-amino, [(C1-C4)-alkoxy]-carbonyl, and [(C1-C4)-haloalkoxy]-carbonyl,
        or (C3-C6)-cycloalkyl, (C4-C6)-cycloalkenyl, (C3-C6)-cycloalkyl which is condensed at one side of the ring to a 4- to 6-membered saturated or unsaturated carbocyclic ring, or (C4-C6)-cycloalkenyl which is condensed at one side of the ring to a 4- to 6-membered saturated or unsaturated carbocyclic ring,
        where each of the 4 lastmentioned radicals is unsubstituted or substituted by one or more radicals selected from the group consisting of halogen, hydroxyl, cyano, (C1-C4)-alkyl, (C1-C4)-haloalkyl, (C1-C4)-alkoxy, (C1-C4)-haloalkoxy, (C1-C4)-alkylthio, (C1-C4)-alkylamino, di[(C1-C4)-alkyl]-amino, [(C1-C4)-alkoxy]-carbonyl, [(C1-C4)-haloalkoxy]-carbonyl, (C3-C6)-cycloalkyl, which is unsubstituted or substituted, phenyl, which is unsubstituted or substituted, and heterocyclyl, which is unsubstituted or substituted,
        and
    
    
    R4 is (C1-C16)-alkyl, (C2-C26)-alkenyl or (C2-C16)-alkynyl,
    
        where each of the 3 lastmentioned radicals is unsubstituted or substituted by one or more radicals selected from the group consisting of halogen, hydroxyl, cyano, (C1-C4)-alkoxy, (C1-C4)-haloalkoxy, (C1-C4)-alkylthio, (C1-C4)-alkylamino, di[(C1-C4)-alkyl]-amino, [(C1-C4)-alkoxy]-carbonyl, and [(C1-C4)-haloalkoxy]-carbonyl,
        or (C3-C6)-cycloalkyl, (C4-C6)-cycloalkenyl, (C3-C6)-cycloalkyl which is condensed at one side of the ring to a 4- to 6-membered saturated or unsaturated carbocyclic ring, or (C4-C6)-cycloalkenyl which is condensed at one side of the ring to a 4- to 6-membered saturated or unsaturated carbocyclic ring,
        where each of the 4 lastmentioned radicals is unsubstituted or substituted by one or more radicals selected from the group consisting of halogen, hydroxyl, cyano, (C1-C4)-haloalkyl, (C1-C4)-alkoxy, (C1-C4)-haloalkoxy, (C1-C4)-alkylthio, (C1-C4)-alkylamino, [(C1-C4)-alkoxy]-carbonyl, [(C1-C4)-haloalkoxy]-carbonyl, (C3-C6)-cycloalkyl, which is unsubstituted or substituted, phenyl, which is unsubstituted or substituted, and heterocyclyl, which is unsubstituted or substituted,
        or
    
    
    R3 is (C1-C4)-alkoxy, (C2-C4)-alkenyloxy, (C2-C6)-alkynyloxy or (C2-C4)-haloalkoxy and
    R4 is hydrogen or (C1-C4)-alkyl or
    R3 and R4 together with the directly attached nitrogen atom are a four- to eight-membered heterocyclic ring which, in addition to the nitrogen atom, may also comprise further hetero ring atoms, preferably up to two further hetero ring atoms selected from the group consisting of N, O and S, and which is unsubstituted or substituted by one or more radicals selected from the group consisting of halogen, cyano, nitro, (C1-C4)-alkyl, (C1-C4)-haloalkyl, (C1-C4)-alkoxy, (C1-C4)-haloalkoxy and (C1-C4)-alkylthio, or
    R3 and R4 together with the directly attached nitrogen atom are the group —N═CR5—NR6R7 in which
    
        R5 is hydrogen or (C1-C6)-alkyl, with hydrogen being preferred, and
        R6, R7 independently of one another are hydrogen or (C1-C4)-alkyl, preferably (C1-C2)-alkyl, or R6 and R7 together with the directly attached nitrogen atom form a five- to seven-membered, preferably saturated heterocyclic ring, such as, for example, piperidinyl, pyrrolidinyl or morpholinyl,
        or
    
    
    R1 is a (C1-C6)-haloalkyl radical, preferably a radical of the formula CF3, CF2Cl, CF2H, CF2CF3, CF2CF2H, CF2CF2Cl, CFClCF3, CFHCF3, CF(CF3)2, CH(CF3)2, CF2CF2CF3 or C(CH3)2F, more preferably CF3, CF2Cl, CF2H, CF2CF3, CF2CF2H, CF2CF2Cl, CF2CF2CF3 or C(CH3)2F, in particular CF2Cl, CF2H, CF2CF3, CF2CF2H, CF2CF2Cl, CF2CF2CF3 or C(CH3)2F, even more preferably CF2Cl, CF2CF3, CF2CF2Cl or CF2CF2CF3,
    R2 is halogen,
    R3 is hydrogen and
    R4 is hydrogen
    
        or
    
    
    R1 is a radical of the formula CF2CF3, CF2CF2H, CF2CF2Cl, CFClCF3, CFHCF3, CF(CF3)2, CH(CF3)2, CF2CF2CF3 or C(CH3)2F, preferably CF2CF3, CF2CF2H, CF2CF2Cl, CFClCF3, CF2CF2CF3 or C(CH3)2F, in particular CF2CF3, CF2CF2H, CF2CF2Cl, CFClCF3 or CF2CF2CF3i even more preferably CF2CF3, CF2CF2H, CF2CF2Cl or CF2CF2CF3,
    R2 is hydrogen,
    R3 is hydrogen and
    R4 is hydrogen.


Preferably excluded are compounds of the formula (I) and salts thereof in which

    R1 is (C1-C3)-alkyl which is substituted by one to three fluorine atoms,
    R2 is hydrogen,
    R3 is (C1-C2)-alkyl and
    R4 is (C1-C2)-alkyl.


The lastmentioned preferably excluded compounds are described in a general manner in the abovementioned EP-A-0522392 as intermediates for preparing sulfonylureas.
Depending on the nature and the attachment of the substituents, the compounds of the formula (I) may be present as stereoisomers. All possible stereoisomers defined by their specific spatial form, such as enantiomers, diastereomers, Z- and E-isomers, are embraced by the formula (I).
If, for example, one or more alkenyl groups are present, it is possible for diastereomers (Z- and E-isomers) to occur. If, for example, one or more asymmetric carbon atoms are present, it is possible for enantiomers and diastereomers to occur. Stereoisomers can be obtained by customary separation methods, for example by chromatographic separation procedures, from the mixtures obtained in the preparation. It is also possible to selectively prepare stereoisomers by employing stereoselective reactions using optically active starting materials and/or auxiliaries. Thus, the invention also relates to all stereoisomers embraced by the formula (I) but not shown in their specific stereoform and mixtures thereof.
The possibilities of combining the various substituents of the formula (I) are to be understood in such a way that the general principles of the synthesis of chemical compounds are to be observed, i.e. the formula (I) does not embrace compounds which the skilled worker knows to be chemically impossible.
The terms used above and further below are familiar to the person skilled in the art and have in particular the meanings illustrated below:
The term “(C1-C4)-alkyl” is a short notation for open-chain alkyl having 1 to 4 carbon atoms corresponding to the stated range of carbon atoms, i.e. it includes the radicals methyl, ethyl, 1-propyl, 2-propyl, 1-butyl, 2-butyl, 2-methylpropyl and tert-butyl. Correspondingly, general alkyl radicals having a wider stated range of carbon atoms, for example “(C1-C6)-alkyl”, also include straight-chain or branched alkyl radicals having a larger number of carbon atoms, i.e. in the example also the alkyl radicals having 5 and 6 carbon atoms.
Unless specifically indicated, the lower carbon skeletons, for example those having 1 to 6 carbon atoms or, in the case of unsaturated groups, having 2 to 6 carbon atoms, are preferred for the hydrocarbon radicals such as alkyl, alkenyl and alkynyl radicals, including in composite radicals. Alkyl radicals, including in the composite meanings, such as alkoxy, haloalkyl, etc., are, for example, methyl, ethyl, n- or isopropyl, n-, iso, t- or 2-butyl, pentyls, hexyls, such as n-hexyl, isohexyl and 1,3-dimethylbutyl, heptyls, such as n-heptyl, 1-methylhexyl and 1,4-dimethylpentyl; alkenyl and alkynyl radicals have the meanings of the possible unsaturated radicals which correspond to the alkyl radicals; alkenyl is, for example, vinyl, allyl, 1-methyl-2-propenyl, 2-methyl-2-propenyl, 2-butenyl, pentenyl, 2-methylpentenyl or hexenyl, preferably allyl, 1-methylprop-2-en-1-yl, 2-methylprop-2-en-1-yl, but-2-en-1-yl, but-3-en-1-yl, 1-methylbut-3-en-1-yl or 1-methylbut-2-en-1-yl. (C2-C6)-alkynyl is, for example, ethynyl, propargyl, 1-methyl-2-propynyl, 2-methyl-2-propynyl, 2-butynyl, 2-pentynyl or 2-hexynyl, preferably propargyl, but-2-yn-1-yl, but-3-yn-1-yl or 1-methylbut-3-yn-1-yl.
Alkylidene, including, for example, in the form (C1-C10)-alkylidene, is the radical of a straight-chain or branched alkane which is attached via a double bond, where the position of the point of attachment has not yet been fixed. The only possible positions in the case of a branched alkane are, of course, positions in which two hydrogen atoms may be replaced by the double bond; radicals are, for example, ═CH2, ═CH—CH3, ═C(CH3)—CH3, ═C(CH3)—C2H5 or ═C(C2H5)—C2H5.
Cycloalkyl is a carbocyclic saturated ring system having preferably 3-8 carbon atoms, for example cyclopropyl, cyclobutyl, cyclopentyl or cyclohexyl. Substituted cycloalkyl embraces cyclic systems having substituents, substituents having a double bond at the cycloalkyl radical, for example an alkylidene group, such as methylidene, also being included. Substituted cycloalkyl also embraces polycyclic aliphatic systems, such as, for example, bicyclo[1.1.0]butan-1-yl, bicyclo[1.1.0]butan-2-yl, bicyclo[2.1.0]-pentan-1-yl, bicyclo[2.1.0]pentan-2-yl, bicyclo[2.1.0]pentan-5-yl, adamantan-1-yl and adamantan-2-yl.
Cycloalkenyl is a carbocyclic, non-aromatic, partially unsaturated ring system having preferably 4-8 carbon atoms, for example 1-cyclobutenyl, 2-cyclobutenyl, 1-cyclopentenyl, 2-cyclopentenyl, 3-cyclopentenyl, or 1-cyclohexenyl, 2-cyclohexenyl, 3-cyclohexenyl, 1,3-cyclohexadienyl or 1,4-cyclohexadienyl. The explanations given for substituted cycloalkyl apply correspondingly to substituted cycloalkenyl.
The term “halogen” denotes, for example, fluorine, chlorine, bromine or iodine. Haloalkyl, haloalkenyl and haloalkynyl are alkyl, alkenyl and alkynyl, respectively, which are partially or fully substituted by identical or different halogen atoms, preferably from the group consisting of fluorine, chlorine and bromine, in particular from the group consisting of fluorine and chlorine, for example monohaloalkyl, such as CH2CH2Cl, CH2CH2F, CH2ClCH3, CH2FCH3, CH2Cl, CH2F; perhaloalkyl such as CCl3 or CF3 or CF3CF2; polyhaloalkyl, such as CHF2, CH2F, CH2FCHCl, CHCl2, CF2CF2H, CH2CF3, CH2ClCH3, CH2FCH3; haloalkoxy is, for example, OCF3, OCHF2, OCH2F, CF3CF2O, OCH2CF3 and OCH2CH2Cl; this applies correspondingly to haloalkenyl and other halogen-substituted radicals.
If a skeleton is substituted “by one or more radicals” from a list of radicals (=group) or a generically defined group of radicals, this includes in each case the simultaneous substitution by a plurality of identical and/or structurally different radicals.
Substituted radicals, such as a substituted alkyl, alkenyl, alkynyl, cycloalkyl, cycloalkenyl, phenyl, benzyl, heterocyclyl and heteroaryl radical, are, for example, substituted radicals derived from an unsubstituted skeleton, the substituents being, for example, one or more, preferably 1, 2 or 3, radicals from the group consisting of halogen, alkoxy, alkylthio, hydroxyl, amino, nitro, carboxyl, cyano, azido, alkoxycarbonyl, alkylcarbonyl, formyl, carbamoyl, mono- and dialkylaminocarbonyl, substituted amino, such as acylamino, mono- and dialkylamino, trialkylsilyl and optionally substituted cycloalkyl, optionally substituted phenyl, optionally substituted heterocyclyl, where each of the lastmentioned cyclic groups may also be attached via heteroatoms or divalent functional groups as in the alkyl radicals mentioned, and alkylsulfinyl, alkylsulfonyl and, in the case of cyclic radicals (=“cyclic skeleton”), also alkyl, haloalkyl, alkylthioalkyl, alkoxyalkyl, optionally substituted mono- and dialkylaminoalkyl and hydroxyalkyl; the term “substituted radicals”, such as substituted alkyl, etc., includes as substituents, in addition to the saturated hydrocarbon-containing radicals mentioned, the corresponding unsaturated aliphatic and aromatic radicals, such as optionally substituted alkenyl, alkynyl, alkenyloxy, alkynyloxy, phenyl, phenoxy etc. In the case of substituted cyclic radicals having aliphatic moieties in the ring, this also embraces cyclic systems having substituents which are attached to the ring via a double bond, for example substituted by an alkylidene group, such as methylidene or ethylidene, or an oxo group, imino group or substituted imino group.
The substituents mentioned by way of example (“first substituent level”) can, if they contain hydrocarbon-containing moieties, be, if appropriate, substituted further in the moieties (“second substituent level”), for example by one of the substituents as defined for the first substituent level. Corresponding further substituent levels are possible. The term “substituted radical” preferably embraces only one or two substituent levels.
Preferred substituents for the substituent levels are, for example, amino, hydroxyl, halogen, nitro, cyano, mercapto, carboxyl, carboxamide, SF5, aminosulfonyl, alkyl, cycloalkyl, alkenyl, cycloalkenyl, alkynyl, monoalkylamino, dialkylamino, N-alkanoylamino, alkoxy, alkenyloxy, alkynyloxy, cycloalkoxy, cycloalkenyloxy, alkoxycarbonyl, alkenyloxycarbonyl, alkynyloxycarbonyl, aryloxycarbonyl, alkanoyl, alkenylcarbonyl, alkynylcarbonyl, arylcarbonyl, alkylthio, cycloalkylthio, alkenylthio, cycloalkenylthio, alkynylthio, alkylsulfinyl, alkylsulfonyl, monoalkylaminosulfonyl, dialkylaminosulfonyl, N-alkylaminocarbonyl, N,N-dialkyl-aminocarbonyl, N-alkanoylaminocarbonyl, N-alkanoyl-N-alkylaminocarbonyl, aryl, aryloxy, benzyl, benzyloxy, benzylthio, arylthio, arylamino, benzylamino, heterocyclyl and trialkylsilyl.
In the case of radicals having carbon atoms, preference is given to those having 1 to 6 carbon atoms, preferably 1 to 4 carbon atoms, in particular 1 or 2 carbon atoms. Preference is generally given to substituents selected from the group consisting of halogen, for example fluorine and chlorine, (C1-C4)-alkyl, preferably methyl or ethyl, (C1-C4)-haloalkyl, preferably trifluoromethyl, (C1-C4)-alkoxy, preferably methoxy or ethoxy, (C1-C4)-haloalkoxy, nitro and cyano. Here, particular preference is given to the substituents methyl, methoxy, fluorine and chlorine.
Substituted amino, such as mono- or disubstituted amino, denotes a radical from the group of the substituted amino radicals which are N-substituted, for example, by one or two identical or different radicals selected from the group consisting of alkyl, alkoxy, acyl and aryl; preferably mono- and dialkylamino, mono- and diarylamino, acylamino, N-alkyl-N-acylamino, N-alkyl-N-acylamino and saturated N-heterocycles; here, preference is given to alkyl radicals having 1 to 4 carbon atoms; aryl is preferably phenyl or substituted phenyl; for acyl, the definition given further down applies, preference is given to (C1-C4)-alkanoyl. This applies correspondingly to substituted hydroxylamino or hydrazino.
Substituted amino also includes quarternary ammonium compounds (salts) with four organic substituents at the nitrogen atom.
Optionally substituted phenyl is preferably phenyl which is unsubstituted or mono- or polysubstituted, preferably up to trisubstituted, by identical or different radicals from the group consisting of halogen, (C1-C4)-alkyl, (C1-C4)-alkoxy, (C1-C4)-haloalkyl, (C1-C4)-haloalkoxy and nitro, for example o-, m- and p-tolyl, dimethylphenyls, 2-, 3- and 4-chlorophenyl, 2-, 3- and 4-fluorophenyl, 2-, 3- and 4-trifluoromethyl- and -trichloromethylphenyl, 2,4-, 3,5-, 2,5- and 2,3-dichlorophenyl, o-, m- and p-methoxyphenyl.
Optionally substituted cycloalkyl is preferably cycloalkyl which is unsubstituted or mono- or polysubstituted, preferably up to trisubstituted, by identical or different radicals from the group consisting of halogen, (C1-C4)-alkyl, (C1-C4)-alkoxy, (C1-C4)-haloalkyl and (C1-C4)-haloalkoxy, in particular by one or two (C1-C4)-alkyl radicals.
Optionally substituted heterocyclyl is preferably heterocyclyl which is unsubstituted or mono- or polysubstituted, preferably up to trisubstituted, by identical or different radicals from the group consisting of halogen, (C1-C4)-alkyl, (C1-C4)-alkoxy, (C1-C4)-haloalkyl, (C1-C4)-haloalkoxy, nitro and oxo, in particular mono- or polysubstituted by radicals from the group consisting of halogen, (C1-C4)-alkyl, (C1-C4)-alkoxy, (C1-C4)-haloalkyl and oxo, very particularly substituted by one or two (C1-C4)-alkyl radicals.
Acyl denotes a radical of an organic acid which, formally, is formed by removing a hydroxyl group from the acid function, it also being possible for the organic radical in the acid to be attached to the acid function via a heteroatom. Examples of acyl are the radical —CO—R of a carboxylic acid HO—CO—R and radicals of acids derived therefrom, such as thiocarboxylic acid, unsubstituted or N-substituted iminocarboxylic acids or the radical of carbonic acid monoesters, N-substituted carbamic acid, sulfonic acids, sulfinic acids, N-substituted sulfonamido acids, phosphonic acids, phosphinic acids.
Acyl denotes, for example, formyl, alkylcarbonyl such as [(C1-C4)-alkyl]carbonyl, phenylcarbonyl, alkyloxycarbonyl, phenyloxycarbonyl, benzyloxycarbonyl, alkylsulfonyl, alkylsulfinyl, N-alkyl-1-iminoalkyl, N-alkyl- and N,N-dialkylcarbamoyl and other radicals of organic acids. Here, the radicals may in each case be substituted further in the alkyl or phenyl moiety, for example in the alkyl moiety by one or more radicals selected from the group consisting of halogen, alkoxy, phenyl and phenoxy; examples of substituents in the phenyl moiety are the substituents which have already been mentioned further above in a general manner for substituted phenyl.
Acyl denotes preferably an acyl radical in the narrower sense, i.e. a radical of an organic acid where the acid group is attached directly to the carbon atom of an organic radical, for example alkanoyl, such as formyl and acetyl, aroyl, such as phenylcarbonyl, and other radicals of saturated or unsaturated organic acids.
“Aroyl” denotes an aryl radical as defined above which is attached via a carbonyl group, for example the benzoyl group.
If a general radical is defined as “hydrogen”, this means a hydrogen atom.
The “yl-position” of a radical denotes its point of attachment.
In accordance with the general definitions:
“(C1-C6)-alkyl” is a methyl, ethyl, propyl, isopropyl, 1-butyl, 2-butyl, 2-methylpropyl or tert-butyl radical;
“(C1-C10)-alkyl” thus includes the alkyl radicals mentioned above, and also isomeric pentyl radicals, such as n-pentyl, 1,1-dimethylpropyl or 2-methylbutyl, isomeric hexyl, heptyl, octyl, nonyl or decyl radicals.
Accordingly, “(C2-C4)-alkenyl” denotes, for example, the vinyl, allyl, 2-methyl-2-propen-1-yl-, 2- or 3-buten-1-yl group,
accordingly, “(C3-C10)-alkenyl” denotes, for example, the allyl, 2-methyl-2-propen-1-yl, 2- or 3-buten-1-yl, pentenyl, 2-methylpentenyl, hexenyl, heptenyl, octenyl, nonenyl or decenyl group.
“(C2-C4)-Alkynyl” denotes, for example, the ethynyl, propargyl or 2-butyn-1-yl group,
“(C3-C10)-alkynyl” denotes, for example, the propargyl, 2-butyn-1-yl, 2-pentyn-1-yl, 2-methylpentyn-3-yl, hexynyl, heptynyl, octynyl, nonynyl or the decynyl group.
If the carbon chain of an alkyl radical is interrupted by more than one oxygen atom, this means that two oxygen atoms must not be directly adjacent.
“(C3-C6)-Cycloalkyl” denotes the cyclopropyl, cyclobutyl, cyclopentyl or cyclohexyl radical,
“(C3-C10)-cycloalkyl” denotes monocycle alkyl radicals, such as the cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl or cyclodecyl radical, denotes bicyclic alkyl radicals, such as the norbornyl or bicyclo[2.2.2]octyl radical, or denotes fused systems, such as the decahydronaphthyl radical.
“(C4-C10)-Cycloalkenyl” denotes monocycle cycloalkylene radicals, such as the cyclobutenyl, cyclopentenyl, cyclohexenyl, cycloheptenyl, cyclooctenyl or cyclodecenyl radical, denotes bicyclic alkyl radicals, such as the norbornenyl or bicyclo[2.2.2]octenyl radical, or denotes fused systems, such as the tetra-, hexa- or octahydronaphthyl radical.
“(C1-C4)-Alkoxy” and “(C1-C10)-alkoxy” are alkoxy groups whose hydrocarbon radicals have the meanings given under the terms “(C1-C4)-alkyl” and “(C1-C10)-alkyl”.
In particular for reasons of better crop-plant- or useful-plant-protecting action (safener action), better selectivity and/or better preparability, the use according to the invention of compounds of the formula (I) mentioned or salts thereof is of particular interest in which individual radicals have one of the preferred meanings already mentioned or mentioned below, and in particular those which contain a combination of one or more of the preferred meanings already mentioned or mentioned below.
Preferably, if embraced by the above mentioned general definition of formula (I),

    R1 is a (C1-C4)-haloalkyl radical, more preferably CF3, CF2Cl, CF2H, CF2CF3, CF2CF2H, CF2CF2Cl, C(CH3)2F or CF2CF2CF3, more preferably CF3, CF2Cl, CF2H, CF2CF2CF3 or CF2CF3, more preferably CF3, CF2Cl, CF2CF2CF3 or CF2CF3, in particular CF3, CF2Cl or CF2CF3.


Preferably,

    R2 is hydrogen or halogen. Here, halogen is preferably fluorine, chlorine, bromine or iodine, in particular chlorine, bromine or iodine, very particularly chlorine or bromine.


Preferably,

    R3 is hydrogen, (C1-C10)-alkyl, (C2-C10)-alkenyl or (C2-C10)-alkynyl,
    
        where each of the 3 last mentioned radicals is unsubstituted or substituted by one or more radicals selected from the group consisting of halogen, hydroxyl, cyano, (C1-C4)-alkoxy, (C1-C4)-haloalkoxy, (C1-C4)-alkylthio, (C1-C4)-alkylamino, di[(C1-C4)-alkyl]-amino, [(C1-C4)-alkoxy]-carbonyl, [(C1-C4)-haloalkoxy]-carbonyl,
        (C3-C6)-cycloalkyl, which is unsubstituted or substituted by one or more radicals from the group consisting of halogen, (C1-C4)-alkyl and (C1-C4)-haloalkyl, preferably unsubstituted or substituted by (C1-C4)-alkyl,
        phenyl, which is unsubstituted or substituted by one or more radicals selected from the group consisting of halogen, (C1-C4)-alkyl, (C1-C4)-haloalkyl, (C1-C4)-alkoxy, (C1-C4)-haloalkoxy and (C1-C4)-alkylthio, and
        heterocyclyl, which is unsubstituted or substituted by one or more radicals selected from the group consisting of halogen, (C1-C4)-alkyl, (C1-C4)-haloalkyl, (C1-C4)-alkoxy, (C1-C4)-haloalkoxy, (C1-C4)-alkylthio and oxo, preferably unsubstituted or substituted by one or more radicals from the group consisting of (C1-C4)-alkyl (C1-C4)-haloalkyl and (C1-C4)-alkoxy,
        or (C3-C6)-cycloalkyl, (C4-C6)-cycloalkenyl, (C3-C6)-cycloalkyl which is condensed at one side of the ring to a 4- to 6-membered saturated or unsaturated carbocyclic ring, or (C4-C6)-cycloalkenyl which is condensed at one side of the ring to a 4- to 6-membered saturated or unsaturated carbocyclic ring,
        where each of the 4 lastmentioned radicals is unsubstituted or substituted by one or more radicals selected from the group consisting of halogen, hydroxyl, cyano, (C1-C4)-alkyl, (C1-C4)-haloalkyl, (C1-C4)-alkoxy, (C1-C4)-haloalkoxy, (C1-C4)-alkylthio, (C1-C4)-alkylamino, [(C1-C4)-alkoxy]-carbonyl, [(C1-C4)-haloalkoxy]-carbonyl,
        (C3-C6)-cycloalkyl, which is unsubstituted or substituted by one or more radicals selected from the group consisting of halogen, (C1-C4)-alkyl and (C1-C4)-haloalkyl, preferably unsubstituted or substituted by (C1-C4)-alkyl,
        phenyl, which is unsubstituted or substituted by one or more radicals selected from the group consisting of halogen, (C1-C4)-alkyl, (C1-C4)-alkoxy, (C1-C4)-haloalkoxy and (C1-C4)-alkylthio, and
        heterocyclyl, which is unsubstituted or substituted by one or more radicals selected from the group consisting of halogen, (C1-C4)-alkyl, (C1-C4)-haloalkyl, (C1-C4)-alkoxy, (C1-C4)-haloalkoxy, (C1-C4)-alkylthio and oxo, preferably unsubstituted or substituted by one or more radicals from the group consisting of (C1-C4)-alkyl, (C1-C4)-haloalkyl and (C1-C4)-alkoxy,
        more preferably hydrogen, (C1-C6)-alkyl, (C2-C6)-alkenyl or (C2-C6)-alkynyl, where each of the 3 lastmentioned radicals is unsubstituted or substituted by one or more radicals selected from the group consisting of (C1-C4)-alkoxy, (C1-C4)-haloalkoxy, (C1-C4)-alkylthio and (C1-C4)-alkoxycarbonyl,
        more preferably hydrogen or (C1-C4)-alkyl, in particular hydrogen,

and

    
    
    R4 is (C1-C10)-alkyl, (C2-C10)-alkenyl or (C2-C10)-alkynyl,
    
        where each of the 3 lastmentioned radicals is unsubstituted or substituted by one or more radicals selected from the group consisting of halogen, hydroxyl, cyano, (C1-C4)-alkoxy, (C1-C4)-haloalkoxy, (C1-C4)-alkylthio, (C1-C4)-alkylamino, di[(C1-C4)-alkyl]amino, [(C1-C4)-alkoxy]-carbonyl, [(C1-C4)-haloalkoxy]-carbonyl,
        (C3-C6)-cycloalkyl, which is unsubstituted or substituted by one or more radicals selected from the group consisting of halogen, (C1-C4)-alkyl and (C1-C4)-haloalkyl, preferably unsubstituted or substituted by (C1-C4)-alkyl,
        phenyl, which is unsubstituted or substituted by one or more radicals selected from the group consisting of halogen, (C1-C4)-alkyl, (C1-C4)-haloalkyl, (C1-C4)-alkoxy, (C1-C4)-haloalkoxy and (C1-C4)-alkylthio, and
        heterocyclyl, which is unsubstituted or substituted by one or more radicals selected from the group consisting of halogen, (C1-C4)-alkyl, (C1-C4)-haloalkyl, (C1-C4)-alkoxy, (C1-C4)-haloalkoxy, (C1-C4)-alkylthio and oxo, preferably unsubstituted or substituted by one or more radicals selected from the group consisting of (C1-C4)-alkyl (C1-C4)-haloalkyl and (C1-C4)-alkoxy,
        or (C3-C6)-cycloalkyl, (C4-C6)-cycloalkenyl, (C3-C6)-cycloalkyl which is condensed at one side of the ring to a 4- to 6-membered saturated or unsaturated carbocyclic ring, or (C4-C6)-cycloalkenyl which is condensed at one side of the ring to a 4- to 6-membered saturated or unsaturated carbocyclic ring,
        where each of the 4 lastmentioned radicals is unsubstituted or substituted by one or more radicals selected from the group consisting of halogen, hydroxyl, cyano, (C1-C4)-alkyl, (C1-C4)-haloalkyl, (C1-C4)-alkoxy, (C1-C4)-haloalkoxy, (C1-C4)-alkylthio, (C1-C4)-alkylamino, di[(C1-C4)-alkyl]-amino, [(C1-C4)-alkoxy]-carbonyl, [(C1-C4)-haloalkoxy]-carbonyl,
        (C3-C6)-cycloalkyl, which is unsubstituted or substituted by one or more radicals selected from the group consisting of halogen, (C1-C4)-alkyl and (C1-C4)-haloalkyl, preferably unsubstituted or substituted by (C1-C4)-alkyl,
        phenyl, which is unsubstituted or substituted by one or more radicals selected from the group consisting of halogen, (C1-C4)-alkyl, (C1-C4)-haloalkyl, (C1-C4)-alkoxy, (C1-C4)-haloalkoxy and (C1-C4)-alkylthio, and
        heterocyclyl, which is unsubstituted or substituted by one or more radicals selected from the group consisting of halogen, (C1-C4)-alkyl, (C1-C4)-haloalkyl, (C1-C4)-alkoxy, (C1-C4)-haloalkoxy, (C1-C4)-alkylthio and oxo, preferably unsubstituted or substituted by one or more radicals selected from the group consisting of (C1-C4)-alkyl, (C1-C4)-haloalkyl and (C1-C4)-alkoxy.
    
    


Here, heterocyclyl is preferably a heterocyclic 3- to 9-membered, in particular 5- or 6-membered, ring having 1 to 3 hetero ring atoms from the group consisting of N, O and S.
More preferably,

    R3 is hydrogen, (C1-C10)-alkyl, (C2-C10)-alkenyl or (C2-C10)-alkynyl,
    
        where each of the 3 lastmentioned radicals is unsubstituted or substituted by one or more radicals selected from the group consisting of halogen, hydroxyl, cyano, (C1-C4)-alkoxy, (C1-C4)-haloalkoxy, (C1-C4)-alkylthio, (C1-C4)-alkylamino, di[(C1-C4)-alkyl]-amino, [(C1-C4)-alkoxy]-carbonyl, [(C1-C4)-haloalkoxy]-carbonyl,
        (C3-C6)-cycloalkyl, which is unsubstituted or substituted by one or more radicals selected from the group consisting of halogen, (C1-C4)-alkyl and (C1-C4)-haloalkyl, preferably unsubstituted or substituted by (C1-C4)-alkyl,
        phenyl, which is unsubstituted or substituted by one or more radicals selected from the group consisting of halogen, (C1-C4)-alkyl, (C1-C4)-haloalkyl, (C1-C4)-alkoxy, (C1-C4)-haloalkoxy and (C1-C4)-alkylthio, and
        heterocyclyl, which is unsubstituted or substituted by one or more radicals selected from the group consisting of halogen, (C1-C4)-alkyl, (C1-C4)-haloalkyl, (C1-C4)-alkoxy, (C1-C4)-haloalkoxy, (C1-C4)-alkylthio and oxo,
        or (C3-C6)-cycloalkyl or (C3-C6)-cycloalkyl which is condensed at one side of the ring to a 4- to 6-membered saturated or unsaturated carbocyclic ring,
        where each of the 2 lastmentioned radicals is unsubstituted or substituted by one or more radicals selected from the group consisting of (C1-C4)-alkyl,
        more preferably hydrogen, (C1-C6)-alkyl, (C2-C6)-alkenyl or (C2-C6)-alkynyl, where each of the 3 lastmentioned radicals is unsubstituted or substituted by one or more radicals selected from the group consisting of (C1-C4)-alkoxy, (C1-C4)-haloalkoxy, (C1-C4)-alkylthio and (C1-C4)-alkoxycarbonyl,
        more preferably hydrogen or (C1-C4)-alkyl, in particular hydrogen,

and

    
    
    R4 is as already defined above for R4 or preferably (C1-C10)-alkyl, (C2-C10)-alkenyl or (C2-C10)-alkynyl,
    
        where each of the 3 lastmentioned radicals is unsubstituted or substituted by one or more radicals selected from the group consisting of halogen, hydroxyl, cyano, (C1-C4)-alkoxy, (C1-C4)-haloalkoxy, (C1-C4)-alkylthio, (C1-C4)-alkylamino, di[(C1-C4)-alkyl]-amino, [(C1-C4)-alkoxy]-carbonyl, [(C1-C4)-haloalkoxy]-carbonyl,
        (C3-C6)-cycloalkyl, which is unsubstituted or substituted by one or more radicals selected from the group consisting of halogen, (C1-C4)-alkyl and (C1-C4)-haloalkyl, preferably unsubstituted by (C1-C4)-alkyl,
        phenyl, which is unsubstituted or substituted by one or more radicals selected from the group consisting of halogen, (C1-C4)-alkyl, (C1-C4)-haloalkyl, (C1-C4)-alkoxy, (C1-C4)-haloalkoxy and (C1-C4)-alkylthio, and
        heterocyclyl, which is unsubstituted or substituted by one or more radicals selected from the group consisting of halogen, (C1-C4)-alkyl, (C1-C4)-haloalkyl, (C1-C4)-alkoxy, (C1-C4)-haloalkoxy, (C1-C4)-alkylthio and oxo,
        or (C3-C6)-cycloalkyl or (C3-C6)-cycloalkyl which is condensed at one side of the ring to a 4- to 6-membered saturated or unsaturated carbocyclic ring,
        where each of the 2 lastmentioned radicals is unsubstituted or substituted by one or more radicals from the group consisting of (C1-C4)-alkyl.
    
    


More preferably.

    R3 is hydrogen, (C1-C10)-alkyl, (C2-C10)-alkenyl or (C2-C10)-alkynyl,
    
        where each of the 3 lastmentioned radicals is unsubstituted or substituted by one or more radicals selected from the group consisting of (C1-C4)-alkoxy, (C1-C4)-haloalkoxy, (C1-C4)-alkylthio and [(C1-C4)-alkoxy]-carbonyl,
        preferably hydrogen, (C1-C6)-alkyl, (C2-C6)-alkenyl or (C2-C6)-alkynyl, where each of the 3 lastmentioned radicals is unsubstituted or substituted by one or more radicals selected from the group consisting of (C1-C4)-alkoxy, (C1-C4)-haloalkoxy, (C1-C4)-alkylthio and (C1-C4)-alkoxycarbonyl,
        more preferably hydrogen or (C1-C4)-alkyl, in particular hydrogen,

and

    
    
    R4 is as already defined above for R4 or preferably
    
        (C1-C10)-alkyl, (C2-C10)-alkenyl or (C2-C10)-alkynyl,
        where each of the 3 lastmentioned radicals is unsubstituted or substituted by one or more radicals selected from the group consisting of (C1-C4)-alkoxy, (C1-C4)-haloalkoxy, (C1-C4)-alkylthio and [(C1-C4)-alkoxy]-carbonyl,
        preferably (C1-C6)-alkyl, (C2-C6)-alkenyl or (C2-C6)-alkynyl, where each of the 3 lastmentioned radicals is unsubstituted or substituted by one or more radicals selected from the group consisting of (C1-C4)-alkoxy, (C1-C4)-haloalkoxy, (C1-C4)-alkylthio and (C1-C4)-alkoxycarbonyl.
    
    


Particular preference is given to the use according to the invention of compounds of the formula (I) or salts thereof in which

    R1 is CF3, CF2Cl, CF2H, CF2CF2CF3 or CF2CF3, preferably CF3, CF2Cl, CF2CF2CF3 or CF2CF3, in particular CF3, CF2Cl or CF2CF3 and
    R2 is hydrogen or halogen, preferably hydrogen, and
    R3 is hydrogen, (C1-C10)-alkyl, (C1-C10)-alkenyl or (C2-C10)-alkynyl,
    
        where each of the 3 lastmentioned radicals is unsubstituted or substituted by one or more radicals selected from the group consisting of (C1-C4)-alkoxy, (C1-C4)-haloalkoxy, (C1-C4)-alkylthio and (C1-C4)-alkoxycarbonyl,
        preferably hydrogen, (C1-C6)-alkyl, (C2-C6)-alkenyl or (C2-C6)-alkynyl, where each of the 3 lastmentioned radicals is unsubstituted or substituted by one or more radicals selected from the group consisting of (C1-C4)-alkoxy, (C1-C4)-haloalkoxy, (C1-C4)-alkylthio and (C1-C4)-alkoxycarbonyl,
        in particular hydrogen or (C1-C4)-alkyl, and
    
    
    R4 is (C1-C10)-alkyl, (C3-C10)-alkenyl or (C3-C10)-alkynyl,
    
        where each of the 3 lastmentioned radicals is unsubstituted or substituted by one or more radicals selected from the group consisting of halogen, hydroxyl, cyano, (C1-C4)-alkoxy, (C1-C4)-haloalkoxy, (C1-C4)-alkylthio, (C1-C4)-alkylamino, di[(C1-C4)-alkyl]-amino, [(C1-C4)-alkoxy]-carbonyl, [(C1-C4)-haloalkoxy]-carbonyl,
        (C3-C6)-cycloalkyl, which is unsubstituted or substituted by one or more radicals selected from the group consisting of halogen, (C1-C4)-alkyl and (C1-C4)-haloalkyl, preferably unsubstituted or substituted by (C1-C4)-alkyl,
        phenyl, which is unsubstituted or substituted by one or more radicals selected from the group consisting of halogen, (C1-C4)-alkyl, (C1-C4)-haloalkyl, (C1-C4)-alkoxy, (C1-C4)-haloalkoxy and (C1-C4)-alkylthio, and
        heterocyclyl, which is unsubstituted or substituted by one or more radicals selected from the group consisting of halogen, (C1-C4)-alkyl, (C1-C4)-haloalkyl, (C1-C4)-alkoxy, (C1-C4)-haloalkoxy, (C1-C4)-alkylthio and oxo,
        or (C3-C6)-cycloalkyl or (C3-C6)-cycloalkyl which is condensed at one side of the ring to a 4- to 6-membered saturated or unsaturated carbocyclic ring,
        where each of the 2 lastmentioned radicals is unsubstituted or substituted by one or more radicals selected from the group consisting of (C1-C4)-alkyl,
        preferably (C1-C10)-alkyl, (C2-C10)-alkenyl or (C2-C10)-alkynyl,
        where each of the 3 lastmentioned radicals is unsubstituted or substituted by one or more radicals selected from the group consisting of (C1-C4)-alkoxy, (C1-C4)-haloalkoxy, (C1-C4)-alkylthio and (Cr C4)-alkoxycarbonyl,
        more preferably (C1-C6)-alkyl, (C2-C6)-alkenyl or (C2-C6)-alkynyl, where each of the 3 lastmentioned radicals is unsubstituted or substituted by one or more radicals selected from the group consisting of (C1-C4)-alkoxy, (C1-C4)-haloalkoxy, (C1-C4)-alkylthio and (C1-C4)-alkoxycarbonyl,

or

    
    
    R3 and R4 together with the directly attached nitrogen atom are a four- to eight-membered heterocyclic ring, preferably a 5- or 6-membered heterocyclic ring, which, in addition to the nitrogen atom, may also contain further hetero ring atoms, preferably up to two further hetero ring atoms from the group consisting of N, O and S, and which is unsubstituted or substituted by one or more radicals selected from the group consisting of halogen, cyano, nitro, (C1-C4)-alkyl, (C1-C4)-haloalkyl, (C1-C4)-alkoxy, (C1-C4)-haloalkoxy and (C1-C4)-alkylthio,

or

    R3 and R4 together with the directly attached nitrogen atom are the group —N═CR5—NR6R7, in which
    
        R5 is hydrogen or (C1-C4)-alkyl, with hydrogen being preferred, and
        R6, R7 independently of one another are hydrogen or (C1-C4)-alkyl, preferably (C1-C2)-alkyl, or R5 and R7 together with the directly attached nitrogen atom form a five- or six-membered, preferably saturated heterocyclic ring, such as, for example, piperidinyl, pyrrolidinyl or morpholinyl.
    
    


Particular preference is also given to the use according to the invention of compounds of the formula (I) or salts thereof in which

    R1 is a (C1-C6)-haloalkyl radical, preferably from the group consisting of CF3, CF2Cl, CF2H, CF2CF3, CF2CF2H, CF2CF2Cl, CF2CF2CF3 and C(CH3)2F, more preferably CF3, CF2Cl, CF2H, CF2CF2CF3 or CF2CF3, even more preferably CF3, CF2Cl, CF2CF2CF3 or CF2CF3, in particular CF3, CF2CF3 or CF2Cl, and
    R2 is halogen and
    R3 is hydrogen and
    R4 is hydrogen.


Likewise particularly preferred is the use according to the invention of compounds of the formula (I) or salts thereof in which

    R1 is CF2Cl, CF2H, CF2CF3, CF2CF2H or CF2CF2Cl, more preferably CF2Cl or CF2H or CF2CF3, more preferably CF2Cl or CF2CF3, in particular CF2Cl,
    R2 is hydrogen and
    R3 is hydrogen or (C1-C4)-alkyl and
    R4 is hydrogen.


Particular preference is also given to the use according to the invention of compounds of the formula (I) or salts thereof in which the general radicals correspond to the radicals mentioned for R1, R2, R3 and R4, respectively, in the examples given in the tables, or embrace them.
Particular preference is also given to the use according to the invention of novel compounds of the formula (I) or salts thereof in which R1, R2, R3 and R4 furthermore preferably have the meanings mentioned for the preferred uses.
The compounds of the general formula (I) can be prepared, for example, by

    (a) reacting a carboxylic acid of the general formula (II)






    
    
        in which R1 and R2 are as defined for the compound of the formula (I) to be prepared, with an amine of the formula (III) or a salt thereof,
    
    






    
    
        in which R3 and R4 are as defined for the compound of the formula (I) to be prepared, if appropriate in the presence of a carboxylic acid-activating reagent, for example N,N-carbonyldiimidazole (CDI), or a dehydrating agent, for example dicyclohexylcarbodiimide (DCC), to give the compound of the formula (I) or
    
    
    (b) reacting a carboxylic ester of the general formula (IV)






    
    
        in which R1 and R2 are as defined for the compound of the formula (I) to be prepared and “Alkyl” is an alkyl radical, for example methyl or ethyl, with an amine of the formula (III) or a salt thereof,
    
    






    
    
        in which R3 and R4 are as defined for the compound of the formula (I) to be prepared, to give the compound of the formula (I) or
    
    
    (c) reacting a carbonyl halide or a carboxylic anhydride of the general formula (V),






    
    
        in which R1 and R2 are as defined for the compound of the formula (I) to be prepared and Hal is a halogen atom, for example chlorine, or an acyloxy radical, with an amine of the formula (III) or a salt thereof,
    
    






    
    
        in which R3 and R4 are as defined for the compound of the formula (I) to be prepared, to give the compound of the formula (I),
    
    
    (d), if R3 and R4 in the compound of the formula (I) to be prepared are each hydrogen, reacting a compound of the formula (VI),






    
    
        in which R1 is as defined for the compound of the formula (I) to be prepared, and “Alkyl” is an alkyl radical, for example methyl or ethyl,
        with malonamide to give the compound of the formula (I).
    
    


The amide formations according to variant (a) can be carried out, for example, in an inert organic solvent in a temperature range between 0° C. and 150° C., preferably between 0° C. and 50° C. Suitable organic solvents are, for example, polar prone or aprotic solvents, such as ethers, for example diethyl ether, tetrahydrofuran and dioxane, or nitrites, such as acetonitrile, or amides, such as dimethylformamide.
The amide formations according to variant (b) can be carried out, for example, in an inert organic solvent in a temperature range between 0° C. and 150° C., preferably between 50° C. and 100° C. Suitable organic solvents are, for example, polar protic or aprotic solvents, such as ethers, for example tetrahydrofuran and dioxane, or nitriles, such as acetonitrile, or amides, such as dimethylformamide. However, preference is given to the amide formation according to variant (b) at elevated temperatures by reacting the undiluted reactants.
The amide formations according to variant (c) can be carried out, for example, in the presence of an acid binder in an inert organic solvent in a temperature range between 0° C. and 150° C., preferably between 50° C. and 100° C. Suitable organic solvents are, for example, polar protic or aprotic solvents, such as ethers, for example diethyl ether, tetrahydrofuran and dioxane, or nitriles, such as acetonitrile, or amides, such as dimethylformamide. Acid binders are, for example, alkali metal or alkaline earth metal carbonates, such as, for example, sodium carbonate, potassium carbonate or calcium carbonate, alkali metal or alkaline earth metal hydroxides, such as sodium hydroxide, potassium hydroxide or calcium hydroxide, or alkali metal hydrides or amides, such as sodium hydride or potassium hydride or sodium amide or potassium amide, or else organic bases, such as triethylamine, pyridine, dimethylaminopyridine, DBU (1,8-diazabicyclo[5.4.0]-undec-7-ene), DBN (1,5-diazabicyclo[4.3.0]non-5-ene) and 1,4-diaza-bicyclo[2.2.2]octane.
The amide formations according to variant (d) can be carried out analogously to the processes described in EP 522392 and Helv. Chim. Acta 71 (1988) 596-601 and GB 2305174. In general, the malonamide can be converted in an organic anhydrous polar prone or aprotic solvent, for example in an alcohol, with a strong base, such as an alkali metal, alkali metal hydride or alkali metal alkoxide, into a reactive salt, and then be reacted with the compound of the formula (VI). The reaction with the compound (VI) can generally be carried out in a temperature range between 0° C. and the boiling point of the solvent (depending on the solvent up to about 150° C.).
The compounds of the general formulae (II), (III), (IV) and (V) are either commercially available or can be prepared by or analogously to methods known to the person skilled in the art (for example Helv. Chim. Acta 71 (1988) 596; EP 502740 (U.S. Pat. No. 5,393,734); EP 522392).
Thus, for example, the compounds of the formula (IVa)




can be obtained by reacting alkoxyvinyl ethers of the formula (VI) with alkyl malonamides of the formula (VII).





The starting materials of the formula (VI) are either commercially available or can be prepared by known methods (for example Synthesis 2000, 738-742; J. Fluor. Chem., 107, 2001, 285-300; Organometallics 15, 1996, 5374-5379).
The compounds of the formula (IV) in which R2 is a halogen atom can be prepared by customary halogenations from the compounds of the formula (IVa).
Suitable for use as halogenating agents for pyridine are, for example, chlorine (J. Org. Chem. 23, 1958, 1614), bromine (Synth. Commun. 19, 1989, 553-560; U.S. Pat. No. 2,532,055), iodine (Tetrahedron Lett. 45, 2004, 6633-6636), sodium hypochlorite (J. Org. Chem. 49, 1984, 4784-4786; J. Med. Chem. 36, 1993, 2676-2688, U.S. Pat. No. 4,960,896), sodium hypobromite (J. Med. Chem. 32, 1989, 2178-2199), thionyl chloride (Organic Letters, 6, 2004, 3-5), N-chlorosuccinimide (J. Med. Chem. 46, 2003, 702-715), N-bromosuccinimide (Chem. Pharm. Bull. 48, 2000, 1847-1853), N-iodosuccinimide (J. Med. Chem. 36, 1993, 2676-2788).
Furthermore, the compounds of the formula (IV) can be prepared from the compounds of the formula (IVa) by successive nitration (for example J. Med. Chem. 36, 1993, 2676-2688; J. Heterocycl. Chem. 33, 1996, 287-294), reduction (for example J. Med. Chem. 33, 1990, 1859-1865), diazotation and subsequent reaction of the diazonium salts in a Sandmeyer or Schiemann reaction.
The compounds of the formula (I) in which R3 and R4 together with the directly attached nitrogen atom are the group —N═CR5—NR6R7 can be prepared by reacting a compound of the formula (I) in which R3 and R4 are hydrogen with compounds of the formula (VIII) in which R5, R6 and R7 are as defined above




according to known methods (see, for example Synthesis 1980, 119-121; J. Med. Chem., 33, 1990, 2052-2059).

The invention also provides a method for protecting crop plants or useful plants against phytotoxic actions of agrochemicals, such as pesticides or, in particular, herbicides which cause damage to crop plants or useful plants, which method comprises using compounds of the formula (I) or salts thereof as safeners, preferably by applying an effective amount of the compounds of the formula (I) or salts thereof to the plants, to parts of plants or their seeds (or seed).
The compounds (I) (=safeners), together with active compounds (pesticides), are suitable for use in the selective control of harmful organisms in a number of plant crops, for example in crops of economic importance, such as cereals (wheat, barley, triticale, rye, rice, corn, millet), sugar beet, sugar cane, oilseed rape, cotton, sunflower, peas, beans and soybeans. Of particular interest is the use in monocotyledonous crops, such as cereals (wheat, barley, rye, triticale, sorghum), including corn and rice, and monocotyledonous vegetable crops, but also in dicotyledonous crops, such as, for example, soybean, oilseed rape, cotton, grape vines, vegetable plants, fruit plants and ornamental plants. The herbicide/safener combinations with the safeners (I) are also suitable for controlling harmful plants in beds and plots of useful plants and ornamental plants, such as, for example, lawn plots with useful or ornamental lawn, especially lolium, meadow grass or Bermuda grass.
Also of interest from among the useful plants and crop plants in which the herbicide/safener combinations with safeners (I) may be used are mutant crops which are completely or partially tolerant to certain pesticides or completely or partially tolerant transgenic crops, for example corn crops which are resistant to glufosinate or glyphosate, or soybean crops which are resistant to herbicidal imidazolinones. However, the particular advantage of the safeners used in this novel way is their efficient action in crops which normally are insufficiently tolerant to the pesticides being applied.
For the joint use with pesticides, the compounds of the formula (I) according to the invention can be applied simultaneously with the active compounds or in any order, and they are then capable of reducing or completely eliminating harmful side effects of these active compounds in crop plants, without negatively affecting or substantially reducing the activity of these active compounds against unwanted harmful organisms. Here, even damage caused by using a plurality of pesticides, for example a plurality of herbicides or herbicides in combination with insecticides or fungicides, can be reduced substantially or eliminated completely. In this manner, it is possible to extend the field of use of conventional pesticides considerably.
If the compositions according to the invention comprise pesticides, these compositions are, after appropriate dilution, applied either directly to the area under cultivation, to the already germinated harmful and/or useful plants or to the already emerged harmful and/or useful plants. If the compositions according to the invention do not comprise any pesticide, these compositions can be employed by the tank mix method—i.e. the user mixes and dilutes the separately available products (=the pesticide and the agent protecting the useful plants) immediately prior to application to the area to be treated—or prior to the application of a pesticide, or after the application of a pesticide, or for the pretreatment of seed, i.e., for example, for dressing the seed of the useful plants. Preferably, safener and pesticide are applied within a short time of one another, in particular when the safener is applied to the plants after the herbicide.
The advantageous actions of the compounds (I) according to the invention are observed when they are used together with the pesticides by the pre-emergence method or the post-emergence method, for example in the case of simultaneous application as a tank mix or a coformulation or in the case of a separate application, in parallel or in succession (split application). It is also possible to repeat the application a number of times. In some cases, it may be expedient to combine a pre-emergence application with a post-emergence application. In most cases, one option is a post-emergence application to the useful plant or crop plant together with a simultaneous or later application of the pesticide. Also possible is the use of the compounds (I) according to the invention for seed dressing, for (dip) treatment of seedlings (for example rice) or for the treatment of other propagation material (for example potato tubers).
When using the compounds (I) according to the invention in combination with herbicides, in addition to the safener action, enhanced action, in the herbicidal action, against harmful plants is frequently also observed. Furthermore, in many cases, there is an improved growth of the useful plants and crop plants, and it is possible to increase the harvest yields.
The compositions according to the invention may comprise one or more pesticides. Suitable pesticides are, for example, herbicides, insecticides, fungicides, acaricides and nematicides, which, when used on their own, would cause phytotoxic damage to the crop plants or would probably cause damage. Of particular interest are corresponding pesticidally active compounds from the groups of the herbicides, insecticides, acaricides, nematicides and fungicides, in particular herbicides.
The weight ratio of safener to pesticide can be varied within wide limits and is generally in the range from 1:100 to 100:1, preferably from 1:20 to 20:1, in particular from 1:10 to 10:1. The optimum weight ratio of safener to pesticide depends both on the respective safener used and the respective pesticide, and on the type of useful plant or crop plant to be protected. The required application rate of safener can, depending on the pesticide used and the type of useful plant to be protected, be varied within wide limits and is generally in the range from 0.001 to 10 kg, preferably from 0.01 to 1 kg, in particular from 0.05 to 0.5 kg, of safener per hectare. The weight ratios and amounts required for a successful treatment can be determined by simple preliminary experiments.
For seed dressing, for example, from 0.005 to 20 g of safener per kilogram of seed, preferably from 0.01 to 10 g of safener per kilogram of seed, in particular from 0.05 to 5 g of safener per kilogram of seed, are used.
If solutions of safener are used for seed treatment and the seeds or seedlings are wetted with the solutions, the suitable concentration is generally in the range from 1 to 10 000 ppm, preferably from 100 to 1000 ppm, based on the weight. The weight ratios and amounts required for a successful treatment can be determined by simple preliminary experiments.
The safeners can be formulated in the customary manner, separately or together with the pesticides. Accordingly, the present invention also provides the useful-plant-protecting or crop-plant-protecting compositions.
Preferred is the joint application of safener and pesticide, in particular that of safener and herbicide as a readymix or the use by the tankmix method.
Preference is also given to using the safener (I) in the treatment of seed, followed by the application of pesticides, preferably herbicides, after sowing by the pre- or post-emergence method.
The compounds of the formula (I) or their salts, as such or in the form of their preparations (formulations), can be used in combination with other pesticidally active compounds, such as, for example, insecticides, acaricides, nematicides, herbicides, fungicides, safeners, fertilizers and/or growth regulators, for example as finished formulation or as tank mixes. Here, the combination formulations can be prepared based on the formulations mentioned above, taking into account the physical properties and stabilities of the active compounds to be combined. Suitable as combination partners for the active compounds according to the invention in formulations of mixtures or in tank-mixes are, for example, known, preferably herbicidally active compounds whose action is based on the inhibition of, for example, acetolactate synthase, acetyl-coenzyme-A carboxylase, PS I, PS II, HPPDO, phytoene desaturase, protoporphyrinogen oxidase, glutamine synthetase, cellulose biosynthesis, 5-enolpyruvylshikimate 3-phosphate synthetase. Such compounds and also other compounds which can be used, in some cases having an unknown or a different mechanism of action, are described, for example, in Weed Research 26, 441-445 (1986), or in “The Pesticide Manual”, 12th edition 2000, or 13th edition 2003 or 14h edition 2006/2007, or in the corresponding “e-Pesticide Manual”, version 4 (2006), all published by the British Crop Protection Council, (hereinbelow also referred to in short as “PM”), and in the literature cited therein. Lists of “common names” are also available in “The Compendium of Pesticide Common Names” on the Internet. Examples of herbicides known from the literature which may be combined with the compounds of the formula (I) are, for example, the following active compounds (note: the compounds are referred to either by the “common name” according to the International Organization for Standardization (ISO) or by the chemical name, if appropriate together with a customary code number):
acetochlor; acibenzolar-5-methyl; acifluorfen(-sodium); aclonifen; AD-67; AKH 7088, i.e. [[[1-[5-[2-chloro-4-(trifluoromethyl)phenoxy]-2-nitrophenyl]-2-methoxyethylidene]amino]oxy]acetic acid and methyl [[[1-[5-[2-chloro-4-(trifluoromethyl)phenoxy]-2-nitrophenyl]-2-methoxyethylidene]-amino]oxy]acetate; alachlor; alloxydim(-sodium); ametryn; amicarbazone, amidochlor, amidosulfuron; aminopyralid; amitrol; AMS, i.e. ammonium sulfamate; ancimidol; anilofos; asulam; atrazine; aviglycine; azafenidin, azimsulfuron (DPX-A8947); aziprotryn; barban; BAS 516 H, i.e. 5-fluoro-2-phenyl-4H-3,1-benzoxazin-4-one; beflubutamid (UBH-509), benazolin(-ethyl); bencarbazone; benfluralin; benfuresate; benoxacor; bensulfuron(-methyl); bensulide; bentazone; benzfendizone; benzobicyclon, benzofenap; benzofluor; benzoylprop(-ethyl); benzthiazuron; bialaphos; bifenox; bispyribac(-sodium) (KIH-2023); borax; bromacil; bromobutide; bromofenoxim; bromoxynil; bromuron; buminafos; busoxinone; butachlor; butafenacil, butamifos; butenachlor (KH-218); buthidazole; butralin; butroxydim, butylate; cafenstrole (CH-900); carbetamide; carfentrazone(-ethyl); CDAA, i.e. 2-chloro-N,N-di-2-propenylacetamide; CDEC, i.e. 2-chlorallyl diethyldithiocarbamate; chlomethoxyfen; chloramben; chlorazifop-butyl, chlorbromuron; chlorbufam; chlorfenac; chlorfenprop; chlorflurecol(-methyl); chlorflurenol(-methyl); chloridazon; chlorimuron(-ethyl); chlormequat(chloride); chlornitrofen; chlorophthalim (MK-616); chlorotoluron; chloroxuron; chlorpropham; chlorsulfuron; chlorthal-dimethyl; chlorthiamid; chlortoluron, cinidon(-methyl and -ethyl), cinmethylin; cinosulfuron; clefoxydim, clethodim; clodinafop and its ester derivatives (for example clodinafop-propargyl); clofencet; clomazone; clomeprop; cloprop; cloproxydim; clopyralid; clopyrasulfuron(-methyl), cloquintocet(-mexyl); cloransulam(-methyl), cumyluron (JC 940); cyanamide; cyanazine; cycloate; cyclosulfamuron (AC 104); cycloxydim; cycluron; cyhalofop and its ester derivatives (for example the butyl ester, DEH-112); cyperquat; cyprazine; cyprazole; cyprosulfamide; daimuron; 2,4-D, 2,4-DB; dalapon; daminozide; dazomet; n-decanol; desmedipham; desmetryn; di-allate; dicamba; dichlobenil; dichlormid; dichlorprop(-P) salts; diclofop and its esters, such as diclofop-methyl; diclofop-P(-methyl); diclosulam, diethatyl(-ethyl); difenoxuron; difenzoquat(metilsulfate); diflufenican; diflufenzopyr(-sodium); dimefuron; dimepiperate, dimethachlor; dimethametryn; dimethazone; dimethenamid (SAN-582H); dimethenamide-P; dimethylarsinic acid; dimethipin; dimetrasulfuron, dinitramine; dinoseb; dinoterb; diphenamid; dipropetryn; diquat salts; dithiopyr; diuron; DNOC; eglinazine-ethyl; EL 77, i.e. 5-cyano-1-(1,1-dimethylethyl)-N-methyl-1H-pyrazole-4-carboxamide; endothal; epoprodan, EPTC; esprocarb; ethalfluralin; ethametsulfuron-methyl; ethephon; ethidimuron; ethiozin; ethofumesate; ethoxyfen and its esters (for example the ethyl ester, HN-252); ethoxysulfuron, etobenzanid (HW 52); F5231, i.e. N-[2-chloro-4-fluoro-5-[4-(3-fluoropropyl)-4,5-dihydro-5-oxo-1H-tetrazol-1-yl]phenyl]ethanesulfonamide; fenchlorazole(-ethyl); fenclorim; fenoprop; fenoxan, fenoxaprop and fenoxaprop-P and also their esters, for example fenoxaprop-P-ethyl and fenoxaprop-ethyl; fenoxydim; fentrazamide, fenuron; ferrous sulfate; flamprop(-methyl or -isopropyl or -isopropyl-L); flamprop-M(-methyl or -isopropyl); flazasulfuron; florasulam, fluazifop and fluazifop-P and their esters, for example fluazifop-butyl and fluazifop-P-butyl; fluazolate, flucarbazone(-sodium), flucetosulfuron; fluchloralin; flufenacet; flufenpyr(-ethyl); flumetralin; flumetsulam; flumeturon; flumiclorac(-pentyl), flumioxazin (S-482); flumipropyn; fluometuron, fluorochloridone, fluorodifen; fluoroglycofen(-ethyl); flupoxam (KNW-739); flupropacil (UBIC-4243); flupropanoate; flupyrsulfuron(-methyl)(-sodium); flurazole; flurenol(-butyl); fluridone; flurochloridone; fluoroxypyr(-meptyl); flurprimidol, flurtamone; fluthiacet(-methyl) (KIH-9201); fluthiamide, fluxofenim; fomesafen; foramsulfuron, forchlorfenuron; fosamine; furilazole; furyloxyfen; gibberillic acid; glufosinate(-ammonium); glyphosate(-isopropylammonium); halosafen; halosulfuron(-methyl); haloxyfop and its esters; haloxyfop-P(═R-haloxyfop) and its esters; HC-252; hexazinone; imazamethabenz(-methyl); imazamethapyr, imazamox, imazapic, imazapyr; imazaquin and salts, such as the ammonium salt; imazethamethapyr; imazethapyr; imazosulfuron; inabenfide; indanofan; indole-3-acetic acid; 4-indol-3-ylbutyric acid; iodosulfuron-methyl(-sodium); ioxynil; isocarbamid; isopropalin; isoproturon; isouron; isoxaben; isoxachlortole, isoxadifen(-ethyl); isoxaflutole, isoxapyrifop; karbutilate; lactofen; lenacil; linuron; maleic hydrazide (MH), MCPA; MCPB; mecoprop(-P); mefenacet; mefenpyr(diethyl); mefluidid; mepiquat(-chloride); mesosulfuron(-methyl); mesotrione, metam; metamifop; metamitron; metazachlor; methabenzthiazuron; metham; methazole; methoxyphenone; methylarsonic acid; methylcyclopropene; methyldymron; methyl isothiocyanate; methabenzthiazuron; metobenzuron; metobromuron; (alpha-)metolachlor; metosulam (XRD 511); metoxuron; metribuzin; metsulfuron-methyl; molinate; monalide; monocarbamide dihydrogensulfate; monolinuron; monuron; MT 128, i.e. 6-chloro-N-(3-chloro-2-propenyl)-5-methyl-N-phenyl-3-pyridazinamine; MT 5950, i.e. N-[3-chloro-4-(1-methylethyl)phenyl]-2-methylpentanamide; naproanilide; napropamide; naptalam; NC 310, i.e. 4-(2,4-dichlorobenzoyl)-1-methyl-5-benzyloxypyrazole; neburon; nicosulfuron; nipyraclofen; nitralin; nitrofen; nitrophenolate mixture; nitrofluorfen; nonanoic acid; norflurazon; orbencarb; orthasulfamuron; oxabetrinil; oryzalin; oxadiargyl (RP-020630); oxadiazon; oxasulfuron, oxaziclomefone, oxyfluorfen; paclobutrazol; paraquat(dichloride); pebulate; pelargonic acid, pendimethalin; penoxsulam; pentachlorophenol; pentanochlor; pentoxazone, perfluidone; pethoxamid; phenisopham; phenmedipham; picloram; picolinafen, pinoxaden, piperophos; piributicarb; pirifenop-butyl; pretilachlor; primisulfuron(-methyl); probenazole; procarbazone-(sodium), propazine; prodiamine; profluralin; profoxydim; prohexadione(-calcium); prohydrojasmon; proglinazine(-ethyl); prometon; prometryn; propachlor; propanil; propaquizafop; propazine; propham; propisochlor; propoxycarbazone(-sodium) (MKH-6561); n-propyl dihydrojasmonate; propyzamide; prosulfalin; prosulfocarb; prosulfuron (CGA-152005); prynachlor; pyraclonil; pyraflufen(ethyl) (ET-751); pyrasulfotole; pyrazolynate; pyrazon; pyrazosulfuron(-ethyl); pyrazoxyfen; pyribenzoxim, pyributicarb, pyridafol, pyridate; pyriftalid; pyriminobac(-methyl) (KIH-6127); pyrimisulfan (KIH-5996); pyrithiobac(-sodium) (KIH-2031); pyroxasulfone (KIH-485); pyroxofop and its esters (for example the propargyl ester); pyroxsulam; quinclorac; quinmerac; quinoclamine, quinofop and its ester derivatives, quizalofop and quizalofop-P and their ester derivatives, for example quizalofop-ethyl; quizalofop-P-tefuryl and -ethyl; renriduron; rimsulfuron (DPX-E 9636); S 275, i.e. 2-[4-chloro-2-fluoro-5-(2-propynyloxy)phenyl]-4,5,6,7-tetrahydro-2H-indazol; saflufenacil (N′-[2-chloro-4-fluoro-5-(3-methyl-2,6-dioxo-4-(trifluoromethyl)-3,6-dihydro-1(2H)-pyrimidinyl)benzoyl]-N-isopropyl-N-methylsulfamide), secbumeton; sethoxydim; siduron; simazine; simetryn; sintofen; SN 106279, i.e. 2-[[7-[2-chloro-4-(trifluoromethyl)phenoxy]-2-naphthalenyl]oxy]propanoic acid and methyl 2-[[7-[2-chloro-4-(trifluoromethyl)phenoxy]-2-naphthalenyl]oxy]propanoate; sulcotrione, sulfentrazone (FMC-97285, F-6285); sulfazuron; sulfometuron(-methyl); sulfosate (ICI-A0224); sulfosulfuron, TCA; tebutam (GCP-5544); tebuthiuron; tecnacene; tembotrione; tefuryltrione; tepraloxydim, terbacil; terbucarb; terbuchlor; terbumeton; terbuthylazine; terbutryn; TFH 450, i.e. N,N-diethyl-3-[(2-ethyl-6-methylphenyl)sulfonyl]-1H-1,2,4-triazole-1-carboxamide; thenylchlor (NSK-850); thiafluamide, thiazafluoron; thiazopyr (Mon-13200); thidiazimin (SN-24085); thidiazuron; thiencarbazone; thifensulfuron(-methyl); thiobencarb; Ti 35; tiocarbazil; topramezone; tralkoxydim; tri-allate; triasulfuron; triaziflam, triazofenamide; tribenuron(-methyl); triclopyr; tridiphane; trietazine; trifloxysulfuron; trifluralin; triflusulfuron and esters (for example the methyl ester, DPX-66037); trimeturon; trinexapac; tritosulfuron, tsitodef; uniconazole; vernolate; WL 110547, i.e. 5-phenoxy-1-[3-(trifluoromethyl)phenyl]-1H-tetrazole; D-489; LS 82-556; KPP-300; NC-324; NC-330; DPX-N8189; SC-0774; DOWCO-535; DK-8910; V-53482; PP-600 and MBH-001.
Insecticides which may cause damage to plants when used on their own or together with herbicides are, for example, the following:
Organophosphates, for example terbufos (Counter®), fonofos (Dyfonate®), phorate (Thimet®), chlorpyriphos (Reldan®), carbamates, such as carbofuran (Furadan®), pyrethroid insecticides, such as tefluthrin (Force®), deltamethrin (Decis®) and tralomethrin (Scout®), and other insecticidal agents having a different mechanism of action.
Herbicides, whose phytotoxic side effects on crop plants can be reduced using compounds of the formula (I) are, for example, herbicides from the group of the carbamates, thiocarbamates, haloacetanilides, substituted phenoxy-, naphthoxy- and phenoxyphenoxycarboxylic acid derivatives and heteroaryloxyphenoxyalkanecarboxylic acid derivatives, such as quinolyloxy-, quinoxalyloxy-, pyridyloxy-, benzoxazolyloxy- and benzothiazolyloxyphenoxyalkanecarboxylic acid esters, cyclohexanedione oximes, benzoylcyclohexanediones, benzoylisoxazoles, benzoylpyrazoles, imidazolinones, pyrimidinyloxypyridinecarboxylic acid derivatives, pyrimidyloxybenzoic acid derivatives, sulfonylureas, sulfonylaminocarbonyltriazolinones, triazolopyrimidinesulfonamide derivatives, phosphinic acid derivatives and salts thereof, glycine derivatives, triazolinones, triazinones and also S—(N-aryl-N-alkylcarbamoylmethyl)dithiophosphoric esters, pyridinecarboxylic acids, pyridines, pyridinecarboxamides, 1,3,5-triazines and others.
Preference is given here to phenoxyphenoxy- and heteroaryloxyphenoxycarboxylic acid esters and salts, cyclohexanedione oximes, benzoylcyclohexanediones, benzoylisoxazoles, benzoylpyrazoles sulfonylureas, sulfonylaminocarbonyltriazolinones, imidazolinones and mixtures of the active compounds mentioned with one another and/or with active compounds used for broadening the activity spectrum of the herbicides, for example bentazone, cyanazine, atrazine, bromoxynil, dicamba and other leaf-acting herbicides.
Herbicides which are suitable for combination with the safeners according to the invention are, for example:
A) herbicides of the type of the phenoxyphenoxy- and heteroaryloxyphenoxycarboxylic acid derivatives, such as
A1) phenoxyphenoxy- and benzyloxyphenoxycarboxylic acid derivatives, for example methyl 2-(4-(2,4-dichlorophenoxy)phenoxy)propionate (diclofop-methyl),

    methyl 2-(4-(4-bromo-2-chlorophenoxy)phenoxy)propionate (DE-A 26 01 548 (U.S. Pat. No. 4,370,489)),
    methyl 2-(4-(4-bromo-2-fluorophenoxy)phenoxy)propionate (U.S. Pat. No. 4,808,750),
    methyl 2-(4-(2-chloro-4-trifluoromethylphenoxy)phenoxy)propionate (DE-A 24 33 067 (U.S. Pat. No. 4,332,960)),
    methyl 2-(4-(2-fluoro-4-trifluoromethylphenoxy)phenoxy)propionate (U.S. Pat. No. 4,808,750),
    methyl 2-(4-(2,4-dichlorobenzyl)phenoxy)propionate (DE-A 24 17 487 (U.S. Pat. No. 4,088,474)),
    ethyl 4-(4-(4-trifluoromethylphenoxy)phenoxy)pent-2-enoate,
    methyl 2-(4-(4-trifluoromethylphenoxy)phenoxy)propionate (DE-A 24 33 067),
    butyl (R)-2-[4-(4-cyano-2-fluorophenoxy)phenoxy]propionate (cyhalofop-butyl)


A2) “monocyclic” heteroaryloxyphenoxyalkanecarboxylic acid derivatives, for example ethyl 2-(4-(3,5-dichloropyridyl-2-oxy)phenoxy)propionate (EP-A 0 002 925),

    propargyl 2-(4-(3,5-dichloropyridyl-2-oxy)phenoxy)propionate (EP-A 0 003 114 (U.S. Pat. No. 4,300,944)),
    methyl (RS)- or (R)-2-(4-(3-chloro-5-trifluoromethyl-2-pyridyloxy)phenoxy)propionate (haloxyfop-methyl or haloxyfop-P-methyl),
    ethyl 2-(4-(3-chloro-5-trifluoromethyl-2-pyridyloxy)phenoxy)propionate (EP-A 0 003 890 (U.S. Pat. No. 4,840,664)),
    propargyl 2-(4-(5-chloro-3-fluoro-2-pyridyloxy)phenoxy)propionate (clodinafop-propargyl),
    butyl (RS)- or (R)-2-(4-(5-trifluoromethyl-2-pyridyloxy)phenoxy)propionate (fluazifop-butyl or fluazifop-P-butyl),
    (R)-2-[4-(3-chloro-5-trifluoromethyl-2-pyridyloxy)phenoxy]propionic acid


A3) “bicyclic” heteroaryloxyphenoxyalkanecarboxylic acid derivatives, for example methyl and ethyl (RS)- or (R)-2-(4-(6-chloro-2-quinoxalyloxy)phenoxy)propionate (quizalofop-methyl and -ethyl or quizalofop-P-methyl and -P-ethyl),

    methyl 2-(4-(6-fluoro-2-quinoxalyloxy)phenoxy)propionate (see J. Pest. Sci. Vol. 10, 61 (1985)),
    2-isopropylidenaminooxyethyl (R)-2-(4-(6-chloro-2-quinoxalyloxy)phenoxy)propionate (propaquizafop),
    ethyl (RS)- or (R)-2-(4-(6-chlorobenzoxazol-2-yloxy)phenoxy)propionate (fenoxaprop-ethyl or fenoxaprop-P-ethyl),
    ethyl 2-(4-(6-chlorobenzthiazol-2-yloxy)phenoxy)propionate (DE-A-26 40 730 (U.S. Pat. No. 4,130,413)),
    tetrahydro-2-furylmethyl (RS)- or (R)-2-(4-(6-chloroquinoxalyloxy)phenoxy) propionate (EP-A-0 323 727 (U.S. Pat. No. 5,120,348));
    (R)-2-[4-(6-chloro-1,3-benzoxazol-2-yloxy)phenoxy]-2′-fluoro-N-methylpropionanilide (metamifop);


B) herbicides from the group of the sulfonylureas, such as pyrimidinyl- or triazinylaminocarbonyl[benzene-, -pyridine-, -pyrazole-, -thiophene- and -(alkyl-sulfonyl)alkylamino]sulfamides. Preferred substituents on the pyrimidine ring or the triazine ring are alkoxy, alkyl, haloalkoxy, haloalkyl, halogen or dimethylamino, it being possible to combine all substituents independently of one another. Preferred substituents in the benzene, pyridine, pyrazole, thiophene or (alkylsulfonyl)alkylamino moiety are alkyl, alkoxy, halogen, nitro, alkoxycarbonyl, aminocarbonyl, alkylaminocarbonyl, dialkylaminocarbonyl, alkoxyaminocarbonyl, haloalkoxy, haloalkyl, alkylcarbonyl, alkoxyalkyl, (alkanesulfonyl)alkylamino. Such suitable sulfonylureas are, for example,
B1) phenyl- and benzylsulfonylureas and related compounds, for example 1-(2-chlorophenylsulfonyl)-3-(4-methoxy-6-methyl-1,3,5-triazin-2-yl)urea (chlorsulfuron),

    1-(2-ethoxycarbonylphenylsulfonyl)-3-(4-chloro-6-methoxypyrimidin-2-yl)urea (chlorimuron-ethyl),
    1-(2-methoxyphenylsulfonyl)-3-(4-methoxy-6-methyl-1,3,5-triazin-2-yl)urea (metsulfuron-methyl),
    1-(2-chloroethoxyphenylsulfonyl)-3-(4-methoxy-6-methyl-1,3,5-triazin-2-yl)urea (triasulfuron),
    1-(2-methoxycarbonylphenylsulfonyl)-3-(4,6-dimethylpyrimidin-2-yl)urea (sulfumeturon-methyl),
    1-(2-methoxycarbonylphenylsulfonyl)-3-(4-methoxy-6-methyl-1,3,5-triazin-2-yl)-3-methylurea (tribenuron-methyl),
    1-(2-methoxycarbonylbenzylsulfonyl)-3-(4,6-dimethoxypyrimidin-2-yl)urea (bensulfuron-methyl),
    1-(2-methoxycarbonylphenylsulfonyl)-3-(4,6-bis-(difluoromethoxy)pyrimidin-2-yl)urea (primisulfuron-methyl),
    3-(4-ethyl-6-methoxy-1,3,5-triazin-2-yl)-1-(2,3-dihydro-1,1-dioxo-2-methylbenzo[b]thiophene-7-sulfonyl)urea (EP-A 0 079 683 (U.S. Pat. No. 4,492,596),
    3-(4-ethoxy-6-ethyl-1,3,5-triazin-2-yl)-1-(2,3-dihydro-1,1-dioxo-2-methylbenzo[b]-thiophene-7-sulfonyl)urea (EP-A 0 079 683),
    3-(4-methoxy-6-methyl-1,3,5-triazin-2-yl)-1-(2-methoxycarbonyl-5-iodophenylsulfonyl)urea (WO 92/13845 (U.S. Pat. No. 5,463,081)),
    methyl 2-[4-dimethylamino-6-(2,2,2-trifluoroethoxy)-1,3,5-triazin-2-ylcarbamoylsulfamoyl]-3-methylbenzoate (DPX-66037, triflusulfuron-methyl),
    oxetan-3-yl 2-[(4,6-dimethylpyrimidin-2-yl)carbamoylsulfamoyl]benzoate (CGA-277476, oxasulfuron),
    methyl 4-iodo-2-[3-(4-methoxy-6-methyl-1,3,5-triazin-2-yl)ureidosulfonyl]benzoate, sodium salt (iodosulfuron-methyl-sodium),
    methyl 2-[3-(4,6-dimethoxypyrimidin-2-yl)ureidosulfonyl]-4-methanesulfonylaminomethylbenzoate (mesosulfuron-methyl, WO 95/10507 (U.S. Pat. No. 5,648,315)),
    N,N-dimethyl-2-[3-(4,6-dimethoxypyrimidin-2-yl)ureidosulfonyl]-4-formylaminobenzamide (foramsulfuron, WO 95/01344 (U.S. Pat. No. 5,658,854)),
    1-(4,6-dimethoxy-1,3,5-triazin-2-yl)-3-[2-(2-methoxyethoxy)phenylsulfonyl]urea (cinosulfuron),
    methyl 2-[(4-ethoxy-6-methylamino-1,3,5-triazin-2-yl)carbamoylsulfamoyl]benzoate (ethametsulfuron-methyl),
    1-(4-methoxy-6-methyl-1,3,5-triazin-2-yl)-3-[2-(3,3,3-trifluoropropyl)phenylsulfonyl]urea (prosulfuron),
    1-(4-methoxy-6-trifluoromethyl-1,3,5-triazin-2-yl)-3-(2-trifluoromethylbenzenesulfonyl)urea (tritosulfuron);
    N-[(4-methylpyrimidin-2-yl)carbamoyl]-2-nitrobenzenesulfonamide (monosulfuron), methyl-2-[({[4-methoxy-6-(methylthio)pyrimidin-2-yl]carbamoyl}amino)sulfonyl]benzoate


B2) thienylsulfonylureas, for example

    1-(2-methoxycarbonylthiophen-3-yl)-3-(4-methoxy-6-methyl-1,3,5-triazin-2-yl)urea (thifensulfuron-methyl);


B3) pyrazolylsulfonylureas, for example

    1-(4-ethoxycarbonyl-1-methylpyrazol-5-ylsulfonyl)-3-(4,6-dimethoxypyrimidin-2-yl)urea (pyrazosulfuron-ethyl),
    methyl 3-chloro-5-(4,6-dimethoxypyrimidin-2-ylcarbamoylsulfamoyl)-1-methylpyrazole-4-carboxylate (halosulfuron-methyl),
    methyl 5-(4,6-dimethylpyrimidin-2-yl-carbamoylsulfamoyl)-1-(2-pyridyl)pyrazole-4-carboxylate (NC-330, see Brighton Crop Prot. Conference ‘Weeds’ 1991, Vol. 1, p. 45 et seq.),
    1-(4,6-dimethoxypyrimidin-2-yl)-3-[1-methyl-4-(2-methyl-2H-tetrazol-5-yl)pyrazol-5-ylsulfonyl]urea (DPX-A8947, azimsulfuron);
    N-[(4,6-dimethoxypyrimidin-2-yl)carbamoyl]-4-(5,5-dimethyl-4,5-dihydroisoxazol-3-yl)-1,3-dimethyl-1H-pyrazole-5-sulfonamide;


B4) sulfonediamide derivatives, for example

    3-(4,6-dimethoxypyrimidin-2-yl)-1-(N-methyl-N-methylsulfonylaminosulfonyl)urea (amidosulfuron) and its structural analogs (EP-A 0 131 258 (U.S. Pat. No. 4,601,747) and Z. Pfl. Krankh. Pfl. Schutz, special issue XII, 489-497 (1990));


B5) pyridylsulfonylureas, for example

    1-(3-N,N-dimethylaminocarbonylpyridin-2-ylsulfonyl)-3-(4,6-dimethoxypyrimidin-2-yl)urea (nicosulfuron),
    1-(3-ethylsulfonylpyridin-2-ylsulfonyl)-3-(4,6-dimethoxypyrimidin-2-yl)urea (rimsulfuron),
    methyl 2-[3-(4,6-dimethoxypyrimidin-2-yl)ureidosulfonyl]-6-trifluoromethyl-3-pyridinecarboxylate, sodium salt (DPX-KE 459, flupyrsulfuron-methyl-sodium),
    3-(4,6-dimethoxypyrimidin-2-yl)-1-(3-N-methylsulfonyl-N-methylaminopyridin-2-yl)sulfonylurea or its salts (DE-A 40 00 503 (U.S. Pat. No. 5,494,886) and DE-A 40 30 577),
    1-(4,6-dimethoxypyrimidin-2-yl)-3-(3-trifluoromethyl-2-pyridylsulfonyl)urea (flazasulfuron),
    1-(4,6-dimethoxypyrimidin-2-yl)-3-[3-(2,2,2-trifluoroethoxy)-2-pyridylsulfonyl]urea sodium salt (trifloxysulfuron-sodium);
    (1RS,2RS; 1RS,2SR)-1-{3-[(4,6-dimethoxypyrimidin-2-ylcarbamoyl)sulfamoyl]-2-pyridyl}-2-fluoropropyl methoxyacetate (flucetosulfuron);


B6) alkoxyphenoxysulfonylureas, for example

    3-(4,6-dimethoxypyrimidin-2-yl)-1-(2-ethoxyphenoxy)sulfonylurea or its salts (ethoxysulfuron);


B7) imidazolylsulfonylureas, for example

    1-(4,6-dimethoxypyrimidin-2-yl)-3-(2-ethylsulfonylimidazo[1,2-a]pyridin-3-yl)sulfonylurea (MON 37500, sulfosulfuron),
    1-(2-chloroimidazo[1,2-a]pyridin-3-ylsulfonyl)-3-(4,6-dimethoxypyrimidin-2-yl)urea (imazosulfuron);
    2-chloro-N-[(4,6-dimethoxypyrimidin-2-yl)carbamoyl]-6-propylimidazo[1,2-b]pyridazine-3-sulfonamide;


B8) phenylaminosulfonylureas, for example

    1-[2-(cyclopropylcarbonyl)phenylaminosulfonyl]-3-(4,6-dimethoxypyrimidin-2-yl)urea (cyclosulfamuron);
    1-(4,6-dimethoxypyrimidin-2-yl)-3-[2-(dimethylcarbamoyl)phenylsulfamoyl]urea (orthosulfamuron);


C) chloroacetanilides, for example

    acetochlor, alachlor, butachlor, dimethachlor, dimethenamid, dimethenamid-P; metazachlor, metolachlor, S-metolachlor, pethoxamid, pretilachlor, propachlor, propisochlor and thenylchlor;


D) thiocarbamates, for example

    S-ethyl N,N-dipropylthiocarbamate (EPTC),
    S-ethyl N,N-diisobutylthiocarbamate (butylate);
    cycloate, dimepiperate, esprocarb, molinate, orbencarb, pebulate, prosulfocarb, thiobencarb, tiocarbazil, tri-allate and vernolate;


E) cyclohexanedione oximes, for example

    alloxydim, butroxydim, clethodim, cloproxydim, cycloxydim, profoxydim, sethoxydim, tepraloxydim and tralkoxydim;


F) imidazolinones, for example

    imazamethabenz-methyl, imazapic, imazamox, imazapyr, imazaquin and imazethapyr;


G) triazolopyrimidinesulfonamide derivatives, for example

    chloransulam-methyl, diclosulam, florasulam, flumetsulam, metosulam and penoxsulam, i.e. 2-(2,2-difluoroethoxy)-N-(5,8-dimethoxy[1,2,4]triazolo[1,5-c]pyrimidin-2-yl)-6-(trifluoromethyl)benzenesulfonamide, and pyroxsulam, i.e. N-(5,7-dimethoxy[1,2,4]triazolo[1,5-a]pyrimidin-2-yl)-2-methoxy-4-(trifluoromethyl)-3-pyridinesulfonamide;


H) benzoylcyclohexanediones, for example

    2-(2-chloro-4-methylsulfonylbenzoyl)cyclohexane-1,3-dione (SC-0051, sulcotrione),
    2-(2-nitrobenzoyl)-4,4-dimethylcyclohexane-1,3-dione (EP-A 0 274 634),
    2-(2-nitro-3-methylsulfonylbenzoyl)-4,4-dimethylcyclohexane-1,3-dione (WO 91/13548),
    2-[4-(methylsulfonyl)-2-nitrobenzoyl]-1,3-cyclohexanedione (mesotrione)
    2-[2-chloro-3-(5-cyanomethyl-4,5-dihydroisoxazol-3-yl)-4-(ethylsulfonyl)benzoyl]-1,3-cyclohexanedione,
    2-[2-chloro-3-(5-cyanomethyl-4,5-dihydroisoxazol-3-yl)-4-(methylsulfonyl)benzoyl]-1,3-cyclohexanedione,
    2-[2-chloro-3-(5-ethoxymethyl-4,5-dihydroisoxazol-3-yl)-4-(ethylsulfonyl)benzoyl]-1,3-cyclohexanedione,
    2-[2-chloro-3-(5-ethoxymethyl-4,5-dihydroisoxazol-3-yl)-4-(methylsulfonyl)benzoyl]-1,3-cyclohexanedione,
    2-[2-chloro-3-[(2,2,2-trifluoroethoxy)methyl]-4-(ethylsulfonyl)benzoyl]-1,3-cyclohexanedione,
    2-[2-chloro-3-[(2,2,2-trifluoroethoxy)methyl]-4-(methylsulfonyl)benzoyl]-1,3-cyclohexanedione (tembotrione),
    2-[2-chloro-3-[(2,2-difluoroethoxy)methyl]-4-(ethylsulfonyl)benzoyl]-1,3-cyclohexanedione,
    2-[2-chloro-3-[(2,2-difluoroethoxy)methyl]-4-(methylsulfonyl)benzoyl]-1,3-cyclohexanedione,
    2-[2-chloro-3-[(2,2,3,3-tetrafluoropropoxy)methyl]-4-(ethylsulfonyl)benzoyl]-1,3-cyclohexanedione,
    2-[2-chloro-3-[(2,2,3,3-tetrafluoropropoxy)methyl]-4-(methylsulfonyl)benzoyl]-1,3-cyclohexanedione,
    2-[2-chloro-3-(cyclopropylmethoxy)-4-(ethylsulfonyl)benzoyl]-1,3-cyclohexanedione,
    2-[2-chloro-3-(cyclopropylmethoxy)-4-(methylsulfonyl)benzoyl]-1,3-cyclohexanedione,
    2-[2-chloro-3-(tetrahydrofuran-2-ylmethoxymethyl)-4-(ethylsulfonyl)benzoyl]-1,3-cyclohexanedione,
    2-[2-chloro-3-(tetrahydrofuran-2-ylmethoxymethyl)-4-(methylsulfonyl)benzoyl]-1,3-cyclohexanedione (tefuryltrione),
    2-[2-chloro-3-[2-(2-methoxyethoxy)ethoxymethyl]-4-(ethylsulfonyl)benzoyl]-1,3-cyclohexanedione,
    2-[2-chloro-3-[2-(2-methoxyethoxy)ethoxymethyl]-4-(methylsulfonyl)benzoyl]-1,3-cyclohexanedione,
    3-({2-[(2-methoxyethoxy)methyl]-6-(trifluoromethyl)pyridin-3-yl}carbonyl)-bicyclo[12.1]octane-2,4-dione (WO 2001094339);


I) benzoylisoxazoles, for example

    5-cyclopropyl-[2-(methylsulfonyl)-4-(trifluoromethyl)benzoyl]isoxazole (isoxaflutole);
    (4-chloro-2-mesylphenyl)(5-cyclopropyl-1,2-oxazol-4-yl)methanone (isoxachlortole);


j) benzoylpyrazoles, for example

    2-[4-(2,4-dichloro-m-toluoyl)-1,3-dimethylpyrazol-5-yloxy]-4′-methylacetophenone (benzofenap),
    4-(2,4-dichlorobenzoyl)-1,3-dimethylpyrazol-5-yltoluene-4-sulfonate (pyrazolynate),
    2-[4-(2,4-dichlorobenzoyl)-1,3-dimethylpyrazol-5-yloxy]acetophenone (pyrazoxyfen);
    5-hydroxy-1-methyl-4-[2-(methylsulfonyl)-4-trifluoromethylbenzoyl]pyrazole (WO 01/74785 (U.S. Pat. No. 6,420,317)),
    1-ethyl-5-hydroxy-4-[2-(methylsulfonyl)-4-trifluoromethylbenzoyl]pyrazole (WO 01/74785),
    1,3-dimethyl-5-hydroxy-4-[2-(methylsulfonyl)-4-trifluoromethylbenzoyl]pyrazole (WO 01/74785),
    1-ethyl-5-hydroxy-3-methyl-4-[2-(methylsulfonyl)-4-trifluoromethylbenzoyl]pyrazole (pyrasulfotole, WO 01/74785),
    5-hydroxy-1-methyl-4-[-2-chlor-3-(4,5-dihydroisoxazol-3-yl)-4-methylsulfonylbenzoyl]pyrazole (WO 99/58509 (U.S. Pat. No. 6,525,204)),
    5-hydroxy-1-methyl-4-[3-(4,5-dihydroisoxazol-3-yl)-2-methyl-4-methylsulfonylbenzoyl]pyrazole (topramezone, WO 99/58509),
    1-ethyl-5-hydroxy-3-methyl-4-[2-methyl-4-methylsulfonyl-3-(2-methoxyethylamino)benzoyl]pyrazole (WO 96/26206 (U.S. Pat. No. 5,846,907)),
    3-cyclopropyl-5-hydroxy-1-methyl-4-[2-methyl-4-methylsulfonyl-3-(2-methoxy-ethylamino)benzoyl]pyrazole (WO 96/26206),
    5-benzoxy-1-ethyl-4-[2-methyl-4-methylsulfonyl-3-(2-methoxyethylamino)benzoyl]pyrazole (WO 96/26206),
    1-ethyl-5-hydroxy-4-(3-dimethylamino-2-methyl-4-methylsulfonylbenzoyl)pyrazole (WO 96/26206),
    5-hydroxy-1-methyl-4-(2-chloro-3-dimethylamino-4-methylsulfonylbenzoyl)pyrazole (WO 96/26206),
    1-ethyl-5-hydroxy-4-(3-allylamino-2-chloro-4-methylsulfonylbenzoyl)pyrazole (WO 96/26206),
    1-ethyl-5-hydroxy-4-(2-methyl-4-methylsulfonyl-3-morpholinobenzoyl)pyrazole (WO 96/26206),
    5-hydroxy-1-isopropyl-4-(2-chloro-4-methylsulfonyl-3-morpholinobenzoyl)pyrazole (WO 96/26206),
    3-cyclopropyl-5-hydroxy-1-methyl-4-(2-chloro-4-methylsulfonyl-3-morpholinobenzoyl)pyrazole (WO 96/26206),
    1,3-dimethyl-5-hydroxy-4-(2-chloro-4-methylsulfonyl-3-pyrazol-1-ylbenzoyl)pyrazole WO 96/26206),
    1-ethyl-5-hydroxy-3-methyl-4-(2-chloro-4-methylsulfonyl-3-pyrazol-1-ylbenzoyl)pyrazole (WO 96/26206),
    1-ethyl-5-hydroxy-4-(2-chloro-4-methylsulfonyl-3-pyrazol-1-ylbenzoyl)pyrazole (WO 96/26206),
    (5-hydroxy-1-methyl-1H-pyrazol-4-yl)(3,3,4-trimethyl-1,1-dioxido-2,3-dihydro-1-benzothien-5-yl)methanone (US2002/0016262),
    1-methyl-4-[(3,3,4-trimethyl-1,1-dioxido-2,3-dihydro-1-benzothien-5-yl)carbonyl]-1H-pyrazol-5-ylpropane-1-sulfonate (US2002/0016262, WO 2002/015695 (US 2002052296));
    3-(2-chloro-4-mesylbenzoyl)-2-phenylthiobicyclo[3.2.1]oct-2-en-4-one (benzobicyclon);


K) sulfonylaminocarbonyltriazolinones, for example

    4,5-dihydro-3-methoxy-4-methyl-5-oxo-N-(2-trifluoromethoxyphenylsulfonyl)-1H-1,2,4-triazole-1-carboxamide sodium salt (flucarbazone-sodium),
    methyl 2-(4,5-dihydro-4-methyl-5-oxo-3-propoxy-1H-1,2,4-triazol-1-yl)carboxamido-sulfonylbenzoate sodium salt (propoxycarbazone-Na);
    methyl 4-[(4,5-dihydro-3-methoxy-4-methyl-5-oxo-1H-1,2,4-triazol-1-yl)carbonyl-sulfamoyl]-5-methylthiophene-3-carboxylate (thiencarbazone-methyl);


L) triazolinones, for example

    4-amino-N-ten-butyl-4,5-dihydro-3-isopropyl-5-oxo-1,2,4-1H-triazole-1-carboxamide (amicarbazone),
    2-(2,4-dichloro-5-prop-2-ynyloxyphenyl)-5,6,7,8-tetrahydro-1,2,4-triazolo[4,3-a]pyridin-3(2H)-one (azafenidin),
    ethyl (RS)-2-chloro-3-[2-chloro-5-(4-difluoromethyl-4,5-dihydro-3-methyl-5-oxo-1H-1,2,4-triazol-1-yl)-4-fluorophenyl]propionate (carfentrazone-ethyl),
    2′,4′-dichloro-5′-(4-difluoromethyl-4,5-dihydro-3-methyl-5-oxo-1H-1,2,4-triazol-1-yl)-methanesulfonanilide (sulfentrazone);
    4-[4,5-dihydro-4-methyl-5-oxo-3-(trifluoromethyl)-1H-1,2,4-triazol-1-yl]-2-[(ethylsulfonyl)amino]-5-fluorobenzenecarbothioamide (bencarbazone);


M) phosphinic acids and derivatives, for example

    4-[hydroxy(methyl)phosphinoyl]-L-homoalanyl-L-alanyl-L-alanine (bilanafos),
    DL-homoalanin-4-yl(methyl)phosphinic acid ammonium salt (glufosinate-ammonium);


N) glycine derivatives, for example

    N-(phosphonomethyl)glycine and its salts (glyphosate and salts, for example the sodium salt or the isopropylammonium salt),
    N-(phosphonomethyl)glycine trimesium salt (sulfosate);


O) pyrimidinyloxypyridinecarboxylic acid derivatives; pyrimidinyloxybenzoic acid derivatives and pyrimidinylthiobenzoic acid derivatives, for example

    benzyl 3-(4,6-dimethoxypyrimidin-2-yl)oxypyridine-2-carboxylate (EP-A 0 249 707 (U.S. Pat. No. 4,832,729)),
    methyl 3-(4,6-dimethoxypyrimidin-2-yl)oxypyridine-2-carboxylate (EP-A 0 249 707),
    1-(ethoxycarbonyloxyethyl) 2,6-bis[(4,6-dimethoxypyrimidin-2-yl)oxy]benzoate (EP-A 0 472 113 (U.S. Pat. No. 5,154,750)),
    2,6-bis[(4,6-dimethoxypyrimidin-2-yl)oxy]benzoic acid (bispyribac-sodium),
    isopropyl 4-[[[2-[(4,6-dimethoxy-2-pyrimidinyl)oxy]phenyl]methyl]amino]benzoate (pyribambenz-isopropyl, WO 2002034724 (U.S. Pat. No. 6,800,590)),
    propyl 4-[[[2-[(4,6-dimethoxy-2-pyrimidinyl)oxy]phenyl]methyl]amino]benzoate (pyribambenz-propyl, WO 2002034724),
    pyribenzoxim, pyriftalid, pyriminobac-methyl, pyrithiobac-sodium, pyrirmisulfan;


P) S—(N-aryl-N-alkylcarbamoylmethyl)dithiophosphonic acid esters, such as S—[N-(4-chlorophenyl)-N-isopropylcarbamoylmethyl]O,O-dimethyl dithiophosphate (anilophos);
Q) triazinones, for example

    3-cyclohexyl-6-dimethylamino-1-methyl-1,3,5-triazine-2,4-(1H,3H)-dione (hexazinone),
    4-amino-4,5-dihydro-3-methyl-6-phenyl-1,2,4-triazin-5-one (metamitron),
    4-amino-6-tert-butyl-4,5-dihydro-3-methylthio-1,2,4-triazin-5-one (metribuzin);


R) pyridinecarboxylic acids, for example

    aminopyralid, clopyralid, fluoroxypyr, picloram and triclopyr;


S) pyridines, for example

    dithiopyr and thiazopyr;


T) pyridinecarboxamides, for example

    diflufenican and picolinafen;


U) 1,3,5-triazines, for example

    ametryn, atrazine, cyanazine, dimethametrin, prometon, prometryn, propazine, simazine, symetryn, terbumeton, terbuthylazine, terbutryn and trietazine;


V) plant growth regulators, for example

    forchlorfenuron and thidiazuron;


W) ketoenoles, for example

    8-(2,6-diethyl-p-tolyl)-1,2,4,5-tetrahydro-7-oxo-7H-pyrazolo[1,2-d][1,4,5]oxadiazepin-9-yl 2,2-dimethylpropionate (pinoxaden);


X) pyrazoles, for example

    3-[5-(difluoromethoxy)-1-methyl-3-(trifluoromethyl)pyrazol-4-ylmethylsulfonyl]-4,5-dihydro-5,5-dimethyl-1,2-oxazole (pyroxasulfone).


The herbicides of groups A to W are known, for example, from the respective abovementioned publications and from “The Pesticide Manual”, The British Crop Protection Council, 14th Edition, 2006, or the e-Pesticide Manual, Version 4.0, British Crop Protection Council 2006 or else from the “Compendium of Pesticide Common Names”.
When used as active compound formulations or coformulations, they generally comprise, if appropriate, the respective customary tackifiers, wetting agents, dispersing agents, emulsifiers, penetrants, preservatives, antifreeze agents and solvents, fillers, carriers and colorants, antifoams, evaporation inhibitors and pH- and viscosity-modifying agents.
The compounds of the formula I and their combinations with one or more of the abovementioned pesticides can be formulated in various ways, depending on the prevailing physicochemical and biological parameters. Examples of suitable formulation types are:

    
    
        emulsifiable concentrates which are prepared by dissolving the active compounds in an organic solvent, for example butanol, cyclohexanone, dimethylformamide, xylene or else relatively high-boiling hydrocarbons or mixtures of the organic solvents with addition of one or more ionic and/or nonionic surfactants (emulsifiers). Suitable emulsifiers are, for example, calcium alkylarylsulfonates, fatty acid polyglycol esters, alkylaryl polyglycol ethers, fatty alcohol polyglycol ethers, propylene oxide/ethylene oxide condensates, alkyl polyethers, sorbitan esters and polyoxyethylenesorbitan fatty acid esters;
        dusts, which are obtained by grinding the active compounds with finely dispersed solid inorganic or organic substances, for example talc, natural clays, such as kaolin, bentonite and pyrophyllite, diatomaceous earth or meals;
        water- or oil-based suspension concentrates, which can be prepared, for example, by wet grinding using bead mills;
        water-soluble powders;
        water-soluble concentrates;
        granules, such as water-soluble granules, water-dispersible granules and granules for application by broadcasting and soil application;
        wettable powders which, in addition to active compound, also contain diluents or inert substances and surfactants;
        capsule suspensions and microcapsules;
        ultra-low-volume formulations.
    
    


The abovementioned formulation types are known to the person skilled in the art and described, for example, in: K. Martens, “Spray Drying Handbook”, 3rd Ed., G. Goodwin Ltd., London, 1979; W. van Valkenburg, “Pesticide Formulations”, Marcel Dekker, N.Y. 1973; Winnaker-Küchler, “Chemische Technologie” [Chemical Technology], volume 7, C. Hanser Verlag Munich, 4th edition 1986; “Perry's Chemical Engineer's Handbook”, 5th Ed., McGraw-Hill, N.Y. 1973, pages 8-57.
The formulation auxiliaries required, such as inert materials, surfactants, solvents and other additives are also known and are described, for example, in: McCutcheon's “Detergents and Emulsifiers Annual”, MC Publ. Corp., Ridgewood N.J.; C. Marsden, “Solvents Guide”, 2nd Ed., Interscience, N.Y. 1963; H. von Olphen, “Introduction to Clay Colloid Chemistry”, 2nd Ed., J. Wiley & Sons, N.Y.; Schönfeldt, “Grenzflächenaktive Äthylenoxidaddukte” [Surface-active ethylene oxide adducts], Wiss. Verlagsgesellschaft, Stuttgart 1976; Sisley and Wood, “Encyclopedia of Surface Active Agents”, Chem. Publ. Co. Inc., N.Y. 1964; Watkins, “Handbook of Insecticide Dust Diluents and Carriers”, 2nd Ed., Darland Books, Caldwell N.J.; Winnacker-Küchler, “Chemische Technologie” [Chemical Technology], volume 7, C. Hanser Verlag Munich, 4th edition 1986.
In addition to the abovementioned formulation auxiliaries, the useful-plant-protecting compositions may comprise, if appropriate, customary tackifiers, wetting agents, dispersants, penetrants, emulsifiers, preservatives, antifreeze agents, fillers, carriers, colorants, anti-foams, evaporation inhibitors and pH or viscosity regulators.
Depending on the formulation type, the useful-plant-protecting compositions generally comprise 0.1 to 99% by weight, in particular 0.2 to 95% by weight, of one or more safeners of the formula I or a combination of safener and pesticide. Furthermore, they comprise 1 to 99.9, in particular 4 to 99.5,% by weight of one or more solid or liquid additives and 0 to 25, in particular 0.1 to 25,% by weight of a surfactant. In emulsifiable concentrates, the concentration of active compound, i.e. the concentration of safener and/or pesticide, is generally 1 to 90, in particular 5 to 80,% by weight. Dusts usually comprise 1 to 30, preferably 5 to 20,% by weight of active compound. In wettable powders, the concentration of active compound is generally 10 to 90% by weight. In water-dispersible granules, the content of active compound is, for example, between 1 and 95% by weight, preferably between 10 and 80% by weight.
For use, the formulations, which are present in commercially available form, are, if appropriate, diluted in a customary manner, for example in the case of wettable powders, emulsifiable concentrates, dispersions and water-dispersible granules, with water. Preparations in the form of dusts, granules and sprayable solutions are usually not diluted with any further inert substances prior to use. The required application rate of the safeners varies with the external conditions such as, inter alia, temperature, humidity and the type of herbicide used.
In the examples below, which illustrate the invention but do not limit it, the amounts are based on weight, unless defined otherwise.
EXAMPLES
1 Formulation Examples
1.1 Dusting Agent
A dusting agent is obtained by mixing 10 parts by weight of a compound of the formula (I) or of an active compound mixture of a pesticide (eg. herbicide) and a safener of the formula (I) and 90 parts by weight of talc as inert material and comminuting in a hammer mill.
1.2 Water-Dispersible Powder
A wettable powder which is readily dispersible in water is obtained by mixing 25 parts by weight of a compound of the formula (I) or of an active compound mixture of a pesticide (eg. herbicide) and a safener of the formula (I), 64 parts by weight of kaolin-containing quartz as inert material, 10 parts by weight of potassium ligninsulfonate and 1 part by weight of sodium oleoylmethyltaurinate as wetting and dispersing agent, and grinding in a pin mill.
1.3 Water-Dispersible Concentrate
A dispersion concentrate which is readily dispersible in water is obtained by mixing 20 parts by weight of a compound of the formula (I) or of an active compound mixture of a pesticide (eg. herbicide) and a safener of the formula (I) with 6 parts by weight of alkylphenol polyglycol ether (®Triton X 207), 3 parts by weight of isotridecanol polyglycol ether and 71 parts by weight of paraffinic mineral oil and grinding in a ball mill to a fineness of below 5 microns.
1.4 Emulsifiable Concentrate
An emulsifiable concentrate is obtained from 15 parts by weight of a compound of the formula (I) or of an active compound mixture of a pesticide (eg. herbicide) and a safener of the formula (I), 75 parts by weight of cyclohexanone as solvent and 10 parts by weight of ethoxylated nonylphenol as emulsifier.
1.5 Water-Dispersible Granules
Water-dispersible granules are obtained by mixing













75 parts by weight
of a safener of the formula (I) or of a mixture of a



pesticide and a safener of the formula (I),


10 parts by weight
of calcium ligninsulfonate,


 5 parts by weight
of sodium lauryl sulfate,


 3 parts by weight
of polyvinyl alcohol and


 7 parts by weight
of kaolin,









grinding in a pin mill and granulating the powder in a fluidized bed by spraying on water as granulation liquid.

Water-dispersible granules are also obtained by homogenizing













25 parts by weight
of a safener of the formula (I) or of a mixture



of a pesticide and a safener of the formula (I),


 5 parts by weight
of sodium 2,2′-dinaphthylmethane-6,6′-disulfonate,


 2 parts by weight
of sodium oleoylmethyltaurinate,


17 parts by weight
of calcium carbonate,


50 parts by weight
of water and


 1 part by weight
of polyvinyl alcohol









in a colloid mill, comminuting, then grinding in a bead mill and atomizing and drying the resulting suspension in a spray tower using a single-fluid nozzle.

2. Preparation Examples
Example A1




N-Cyclobutyl-2-oxo-6 (trifluoromethyl)-1,2-dihydropyridine-3-carboxamide
A1.1) 4-Butoxy-1,1,1-trifluorobut-3-en-2-one
At 5° C., 79.9 g (0.38 mol) of trifluoroacetic anhydride—dissolved in 100 ml of trichloromethane—were added with stirring to a mixture of 29.9 g (0.38 mol) of pyridine and 50.0 g (0.38 mol) of butyl vinyl ether in 200 ml of trichloromethane. After the addition, stirring was continued at room temperature for another 15 h. 300 ml of water were then added to the mixture, and the organic phase was separated off, dried and concentrated. This gave 59 g (79% of theory) of a yellowish oil.
1H-NMR: [CDCl3] 0.96 (t, 3H); 1.41 (m, 2H); 1.73 (m, 2H); 4.04 (t, 2H); 5.85 (d, 1H); 7.90 (d, 1H).
A1.2) Methyl 2-oxo-6-(trifluoromethyl)-1,2-dihydropyridine-3-carboxylate
2.15 g (94 mmol) of sodium were dissolved in 300 ml of methanol, 15.3 g (78 mmol) of 4-butoxy-1,1,1-trifluorobut-3-en-2-one and 9.13 g (78 mmol) of methyl malonatemonoamide were added and the mixture was heated under reflux for 18 h. The mixture was concentrated, and the residue was taken up in water and washed with dichloromethane. The aqueous phase was then adjusted to pH 2 by addition of 2N hydrochloric acid and extracted with dichloromethane. Drying and concentration of the extract gave 12 g (69% of theory) of a colorless powder.
1H-NMR: [CDCl3] 4.03 (s, 3H); 7.31 (d, 1H); 8.39 (d, 1H).
A1.3) 2-Oxo-6-(trifluoromethyl)-1,2-dihydropyridine-3-carboxylic acid
At room temperature, 4.73 g (21.4 mmol) of methyl 2-oxo-6-(trifluoromethyl)-1,2-dihydropyridine-3-carboxylate were dissolved in 45 ml of methanol and 15 ml of water, 1.80 g (42.8 mmol) of lithium hydroxide monohydrate were added and the mixture was then heated under reflux for 2 h. The mixture was concentrated to about 15 ml and then washed with dichloromethane and the aqueous phase was adjusted to pH 2 by addition of 2N hydrochloric acid. The mixture was again extracted with dichloromethane, and the organic phase was dried and concentrated. This gave 4.2 g (94% of theory) of a colorless powder.
1H-NMR: [DMSO] 7.41 (d, 1H); 8.35 (d, 1H).
A1.4) N-Cyclobutyl-2-oxo-6-(trifluoromethyl)-1,2-dihydropyridine-3-carboxamide
600 mg (2.9 mmol) of 2-oxo-6-(trifluoromethyl)-1,2-dihydropyridine-3-carboxylic acid were dissolved in 5 ml of tetrahydrofuran, 658 mg (4.1 mmol) of N,N-carbonyldiimidazole were added and the mixture was heated initially at room temperature for 30 min and then under reflux for 30 min. A solution of 247 mg (3.5 mmol) of cyclobutylamine in 5 ml tetrahydrofuran was then added dropwise, and the mixture was heated under reflux for a further 2 h. The solution was evaporated to dryness and then taken up in ethyl acetate, washed with 1 N hydrochloric acid and water, dried and concentrated. Purification by column chromatography gave 160 mg (19% of theory) of a light-brown powder.
1H-NMR: [CDCl3] 1.80 (m, 2H); 2.00 (m, 2H); 2.42 (m, 2H); 4.55 (m, 1H); 6.88 (d, 1H); 8.65 (d, 1H); 9.50 (br, 1H).
Example A2




6-[Chloro(difluoro)methyl]-N-(2-methoxyethyl)-2-oxo-1,2-dihydropyridine-3-carboxamide
A2.1) 4-Butoxy-1-chloro-1,1-difluorobut-3-en-2-one
Under stirring at 5° C., 5.0 g (20.2 mmol) of chlorodifluoroacetic anhydride—dissolved in 10 ml of trichloromethane—were added to a mixture of 1.60 g (20.2 mmol) of pyridine and 2.1 g (20.2 mmol) of butyl vinyl ether in 30 ml of trichloromethane. After the addition, stirring was continued at room temperature for another 15 h. 100 ml of water were then added to the mixture, and the organic phase was separated off, dried and concentrated. This gave 3.4 g (80% of theory) of a yellowish oil.
1H-NMR: [DMSO] 0.90 (t, 3H); 1.35 (m, 2H); 1.65 (m, 2H); 4.20 (t, 2H); 6.04 (d, 1H); 8.10 (d, 1H).
A2.2) Methyl 6-[chloro(difluoro)methyl]-2-oxo-1,2-dihydropyridine-3-carboxylate
1.47 g (61 mmol) of sodium were dissolved in 220 ml of methanol, 10 g (47 mmol) of 4-butoxy-1-chloro-1,1-difluorobut-3-en-2-one and 5.51 g (47 mmol) of methyl malonatemonoamide were added and the mixture was heated under reflux for 21 h. The pH was adjusted to 4-5 by addition of 2N hydrochloric acid, and about 200 ml were then distilled off. The solution that remained was extracted with ethyl acetate, and the extract was dried and concentrated. The residue was triturated with diisopropyl ether, filtered off with suction and dried. This gave 7.4 g (66% of theory) of a colorless powder.
1H-NMR: [CDCl3] 4.01 (s, 3H); 7.30 (d, 1H); 8.38 (d, 1H); 11.5 (br, 1H).
A2.3a) 6-[Chloro(difluoro)methyl]-2-oxo-1,2-dihydropyridine-3-carboxylic acid
1.70 g (74 mmol) of sodium were dissolved in 250 ml of methanol, 13.1 g (61.7 mmol) of 4-butoxy-1-chloro-1,1-difluorobut-3-en-2-one and 7.22 g (61.7 mmol) of methyl malonatemonoamide were added and the mixture was heated under reflux for 21 h. 250 ml of water and 2.9 g (67.9 mmol) of lithium hydroxide monohydrate were then added, and heating under reflux was continued for a further 2 h. The mixture was concentrated to about 200 ml and washed with dichloromethane, and the aqueous phase was acidified with 2N hydrochloric acid to pH 2. The precipitated solid was filtered off with suction and dried under reduced pressure. 9.3 g (68% of theory).
A2.3b) 6-[Chloro(difluoro)methyl]-2-oxo-1,2-dihydropyridine-3-carboxylic acid
11.0 g (49.4 mmol) of 6-[chloro(difluoro)methyl]-2-oxo-1,2-dihydropyridine-3-carboxamide were heated in 77 ml of 50% strength sulfuric acid. The mixture was then added to ice water, and the precipitate was filtered off with suction and dried. This gave 7.2 g (65% of theory) of a yellowish powder.
m.p.: 145-147° C.
1H-NMR: [DMSO] 7.36 (d, 1H); 8.34 (d, 1H).
A2.4) 6-[Chloro(difluoro)methyl]-N-(2-methoxyethyl)-2-oxo-1,2-dihydropyridine-3-carboxamide
500 mg (2.2 mmol) of 6-[chloro(difluoro)methyl]-2-oxo-1,2-dihydropyridine-3-carboxylic acid were dissolved in 10 ml of tetrahydrofuran, 508 mg (3.1 mmol) of N,N-carbonyldiimidazole were added and the mixture was then stirred initially at room temperature for 30 min and then under reflux for min. A solution of 202 mg (2.7 mmol) of 2-methoxyethylamine in 2 ml of tetrahydrofuran was then added dropwise, and the mixture was heated under reflux for a further 2 h. The solution was evaporated to dryness, the residue was taken up in ethyl acetate and the solution was washed with 1N hydrochloric acid and water, dried and concentrated. This gave 360 mg (54% of theory) of a light-brown powder.
1H-NMR: [CDCl3] 3.40 (s, 3H); 3.58 (m, 2H); 3.67 (m, 2H); 6.84 (d, 1H), 8.62 (d, 1H); 9.40 (br, 1H).
Example A3




Methyl N-({6-[chloro(difluoro)methyl]2 oxo-1,2-dihydropyridin-3-yl}carbonyl)glycinate
300 mg (1.34 mmol) of 6-[chloro(difluoro)methyl]-2-oxo-1,2-dihydropyridine-3-carboxylic acid were dissolved in 5 ml of tetrahydrofuran, 435 mg (2.68 mmol) of N,N-carbonyldiimidazole were added and the mixture was stirred initially at room temperature for 30 min and then under reflux for 30 min. A mixture of 168 mg (1.34 mmol) of glycine methyl ester hydrochloride in 3 ml of tetrahydrofuran was then added, and the mixture was heated under reflux for a further 2 h. The solution was evaporated to dryness, the residue was taken up in ethyl acetate and the solution was washed with 1N hydrochloric acid and water, dried and concentrated. This gave 92 mg (23% of theory) of a light-brown powder.
1H-NMR: [DMSO] 3.65 (s, 3H); 4.12 (d, 2H); 7.28 (d, br, 1H); 8.42 (d, 1H); 9.25 (t, br, 1H), 13.6 (br, 1H)
Example A4




N-(1-Methylpropyl)-2-oxo-6 (pentafluoroethyl)-1,2-dihydropyridine-3-carboxamide
A4.1) 1-Butoxy-4,4,5,5,5-pentafluoropent-1-en-3-one
With stirring at −10° C., 17.0 g (93.2 mmol) of pentafluoropropionyl chloride—dissolved in 20 ml of dichloromethane—were added to a mixture of 8.11 g (102 mmol) pyridine and 9.33 g (93.2 mmol) of butyl vinyl ether in 200 ml of dichloromethane. After the addition, stirring was continued at room temperature for a further 15 h. 200 ml of water were then added to the mixture, and the organic phase was separated off, dried and concentrated. This gave 18.9 g (82% of theory) of a yellowish oil.
1H-NMR: [DMSO] 0.85 (t, 3H); 1.32 (m, 2H); 1.63 (m, 2H); 4.20 (t, 2H); 6.06 (d, 1H); 8.11 (d, 1H).
A4.2) Ethyl 2-oxo-6-(pentafluoroethyl)-1,2-dihydropyridine-3-carboxylate
0.56 g (24.4 mmol) of sodium was dissolved in 150 ml of ethanol, 5 g (20.3 mmol) of 1-butoxy-4,4,5,5,5-pentafluoropent-1-en-3-one and 2.66 g (20.3 mmol) of methyl malonatemonoamide were added and the mixture was heated under reflux for 6 h. The mixture was concentrated to about 50 ml, 500 ml of 1N hydrochloric acid were added and the mixture was then extracted with ethyl acetate. Drying and concentration gave 2.3 g (40% of theory) of a yellowish resin.
1H-NMR: [CDCl3] 1.45 (t, 3H); 4.50 (q, 2H); 7.35 (d, 1H); 8.40 (d, 1H); 11.4 (br, 1H).
A4.3) N-(1-Methylpropyl)-2-oxo-6-(pentafluoroethyl)-1,2-dihydropyridine-3-carboxamide
At room temperature, 160 mg (0.56 mmol) of ethyl 2-oxo-6-(pentafluoroethyl)-1,2-dihydropyridine-3-carboxylate were stirred in 5 ml of 2-butylamine for 14 h. The pH was then adjusted to 2 by addition of 1N hydrochloric acid, which resulted in the precipitation of a colorless solid. Filtration with suction and drying gave 160 mg (91% of theory) of the product.
1H-NMR: [CDCl3] 0.97 (t, 3H); 1.22 (d, 3H); 1.59 (m, 2H); 4.10 (m, 1H); 6.88 (d, 1H); 8.72 (d, 1H); 9.24 (d, br, 1H); 13.6 (br).
Example A5




2-Oxo-6-(pentafluoroethyl)-1,2-dihydropyridine-3-carboxamide
0.22 g (9.7 mmol) of sodium was dissolved in 50 ml of ethanol, 2 g (8.1 mmol) of 1-butoxy-4,4,5,5,5-pentafluoropent-1-en-3-one and 0.86 g (8.1 mmol) malonamide were added and the mixture was heated under reflux for 7 h. The mixture was concentrated, and 1N hydrochloric acid was added. The resulting precipitate was filtered off with suction and dried. This gave 1.9 g (94% of theory) of a yellow powder.
1H-NMR: [DMSO] 7.45 (d, 1H); 8.15 (br, 1H); 8.45 (br, 1H); 8.50 (d, 1H); 13.7 (br, 1H).
Example A6




N-[(Dimethylamino)methylene]-2-oxo-6-(trifluoromethyl)-1,2-dihydropyridine-3-carboxamide
0.87 g (7.28 mmol) of N,N-dimethylformamide dimethyl acetal was added to 1.00 g (4.85 mmol) of 2-oxo-6-(trifluoromethyl)-1,2-dihydropyridine-3-carboxamide in 5 ml of toluene, and the mixture was heated under reflux for 4 h. After cooling, the resulting precipitate was filtered off with suction and dried: 0.5 g (39% of theory).
1H-NMR: [CDCl3] 3.25 (s, 3H); 3.35 (3. 3H); 7.25 (d, 1H); 8.58 (d, 1H); 8.76 (s, 1H)
13C-NMR. [CDCl3] 35 (NMe2); 106 (C-5); 115 (C-3); 122 (q, CF3); 143 (C-4); 151 (C-6); 164 (N═CN); 167 (C-2); 171 (CON).
Example A7




5-Chloro-2-oxo-6-(trifluoromethyl)-1,2-dihydropyridine-3-carboxamide
At room temperature, 0.39 g (2.9 mmol) of sulfuryl chloride was added to 300 mg (1.46 mmol) of 2-oxo-6-(trifluoromethyl)-1,2-dihydropyridine-3-carboxamide in 5 ml of 1,2-dichloroethane and 2.3 g (0.25 ml) of pyridine, and the mixture was then heated under reflux for 2 h. The mixture was then added to 0.5N hydrochloric acid. The organic phase was removed and then dried and concentrated, which gave 144 mg (41% of theory) of a brownish powder.
1H-NMR: [DMSO] 8.25 (br, 1H); 8.35 (br, 1H); 8.50 (s, 1H); 13.8 (br, 1H)
13C-NMR. [DMSO] 118 (C-5); 120 (C-6); 120.5 (q, CF3); 144 (C-4), 161 (C-2); 166 (COONH2).
Example A8




N-Allyl-5-bromo-2-oxo-6-(trifluoromethyl)-1,2-dihydropyridine-3-carboxamide
A8.1) Methyl 5-bromo-2-oxo-6-(trifluoromethyl)-1,2-dihydropyridine-3-carboxylate
At room temperature, 0.36 g (2.04 mmol) of N-bromosuccinimide was added to a suspension of 0.3 g (1.36 mmol) of methyl 2-oxo-6-(trifluoromethyl)-1,2-dihydropyridine-3-carboxylate in 10 ml of glacial acetic acid, and the mixture was then heated under reflux for 2 days. The reaction mixture was then added to water and extracted with dichloromethane. The extract was concentrated, and the residue was purified further by preparative HPLC. This gave 227 mg (56% of theory) of a colorless powder.
1H-NMR: [DMSO] 3.85 (s, 3H); 8.45 (s, 1H); 12.80 (br, 1H);
13C-NMR. [DMSO] 53 (OCH3); 105 (C-3); 148 (C-4), 161 (C-2); 164 (COOMe).
A8.2) N-Allyl-5-bromo-2-oxo-6-(trifluoromethyl)-1,2-dihydropyridine-3-carboxamide
At room temperature, 250 mg (0.83 mmol) of methyl 5-bromo-2-oxo-6-(trifluoromethyl)-1,2-dihydropyridine-3-carboxylate were stirred in 5 ml of allylamine for 18 h. By addition of 2N hydrochloric acid, the pH was then adjusted to 2, resulting in the precipitation of a colorless solid. Filtration with suction and drying gave 134 mg (50% of theory) of the product.
1H-NMR: [DMSO] 3.94 (t, 2H); 5.18 (dd, 2H); 5.89 (m, 1H); 8.52 (s, 1H); 8.85 (t, br, 1H).
Example A9




6-Difluoromethyl-N-isopropyl-2-oxo-1,2-dihydropyridine-3-carboxamide
A9.1) 4-Butoxy-1,1-difluorobut-3-en-2-one
With stirring at 5° C., 10.0 g (55.7 mmol) of difluoroacetic anhydride were added to a mixture of 4.41 g (4.5 ml, 55.7 mmol) of pyridine and 5.7 g (55.7 mmol) butyl vinyl ether in 330 ml of trichloromethane. After the addition, stirring was continued at room temperature for a further 15 h. 300 ml of water were then added to the mixture, and the organic phase was separated off, dried and concentrated. This gave 5.7 g (57% of theory) of a yellowish oil.
1H-NMR: [CDCl3] 0.95 (t, 3H); 1.42 (m, 2H); 1.72 (m, 2H); 4.00 (t, 2H); 5.78 (t, 1H); 5.90 (d, 1H); 7.85 (d, 1H).
A9.2) Methyl 6-(difluoromethyl)-2-oxo-1,2-dihydropyridine-3-carboxylate
1.21 g (52.9 mmol) of sodium were dissolved in 200 ml of methanol, 7.9 g (44 mmol) of 4-butoxy-1,1-difluorobut-3-en-2-one and 5.3 g (44 mmol) of methyl malonatemonoamide were then added and the mixture was heated under reflux for 15 h. The mixture was concentrated and the residue was then triturated with 100 ml of 1N hydrochloric acid. The solid obtained was filtered off with suction and dried: 7.4 g (82% of theory).
1H-NMR: [DMSO] 3.82 (s, 3H); 6.85 (t, 1H); 7.02 (d, br, 1H); 8.20 (d, 1H); 12.4 (br, 1H).
A9.3) 6-(Difluoromethyl)-2-oxo-1,2-dihydropyridine-3-carboxylic acid
7.4 g (36.4 mmol) of methyl 6-(difluoromethyl)-2-oxo-1,2-dihydropyridine-3-carboxylate were dissolved in 100 ml of methanol, and a solution of 1.3 g (54.6 mmol) of lithium hydroxide in 50 ml of water was added. After two hours of heating under reflux, the mixture was concentrated to a volume of about 50 ml and the solution was washed with dichloromethane. The aqueous phase was then acidified with 2N hydrochloric acid and extracted with ethyl acetate. Drying and concentration of the extract gave 5.6 g (82% of theory) of a brownish powder.
A9.4) 6-(Difluoromethyl)-N-isopropyl-2-oxo-1,2-dihydropyridine-3-carboxamide
After dissolution of 200 mg (1.1 mmol) of 6-(difluoromethyl)-2-oxo-1,2-dihydropyridine-3-carboxylic acid in 25 ml of tetrahydrofuran and addition of 206 mg (1.3 mmol) of N,N-carbonyldiimidazole, the mixture was stirred initially at room temperature for 30 min and then under reflux for 30 min. A solution of 66 mg (1.1 mmol) of isopropylamine in 5 ml of tetrahydrofuran was then added dropwise, and the mixture was heated under reflux for a further 2 h. The solution was evaporated to dryness, the residue was then taken up in ethyl acetate and the mixture was washed with 2N hydrochloric acid and water, dried and concentrated. Purification by column chromatography gave 150 mg (61% of theory) of a colorless powder.
1H-NMR: [CDCl3] 1.25 (d, 6H); 4.22 (m, 1H); 6.55 (t, 1H); 6.69 (d, 1H); 8.64 (d, 1H); 9.42 (d, br, 1H); 13.0 (br, 1H).
Example A10




6-(Heptafluoropropyl)-2-oxo-N-propyl-1,2-dihydropyridine-3-carboxamide
A10.1) 1-Butoxy-4,4,5,5,6,6,6-heptafluorohex-1-en-3-one
With stirring and at −10° C., 21.7 g (93.2 mmol) of heptafluorobutyryl chloride—dissolved in 50 ml of dichloromethane—were added to a mixture of 8.11 g (102 mmol) of pyridine and 9.33 g (93.2 mmol) of butyl vinyl ether in 200 ml of dichloromethane. After the addition, stirring was continued at room temperature for another 15 h. 300 ml of water were then added to the mixture, and the organic phase was separated off, dried and concentrated.
This gave 28.2 g (82% of theory) of a yellowish oil which was reacted further without further purification.
1H-NMR: [CDCl3] 0.96 (t, 3H); 1.40 (m, 2H); 1.75 (m, 2H); 4.04 (t, 2H); 5.95 (d, 1H); 7.93 (d, 1H).
A10.2) Methyl 6-(heptafluoropropyl)-2-oxo-1,2-dihydropyridine-3-carboxylate
After dissolution of 2.63 g (114 mmol) of sodium in 250 ml of methanol, 28.2 g (95.5 mmol) of 1-butoxy-4,4,5,5,6,6,6-heptafluorohex-1-en-3-one and 11.18 g (95.5 mmol) of methyl malonatemonoamide were added, and the mixture was heated under reflux for 18 h. The mixture was concentrated and the residue was then taken up in water and washed with dichloromethane. The aqueous phase was then adjusted to pH 2 by addition of 2N hydrochloric acid and extracted with dichloromethane, Drying, concentration and purification of the extract by column chromatography gave 15.2 g (49% of theory) of a yellow powder.
1H-NMR: [CDCl3] 4.06 (s, 3H); 7.35 (d, 1H); 8.40 (d, 1H); 11.4 (br, 1H).
A10.3) 6-(Heptafluoropropyl) 2 oxo-N-propyl-1,2-dihydropyridine-3-carboxamide
250 mg (0.78 mmol) of methyl 6-(heptafluoropropyl)-2-oxo-1,2-dihydropyridine-3-carboxylate in 5 ml of propylamine were heated under reflux for 5 h. The mixture was then adjusted to pH 2 by addition of 1N hydrochloric acid and extracted with dichloromethane. Drying and concentration gave 240 mg (88% of theory) of a beige powder.
1H-NMR: [DMSO] 0.90 (t, 3H); 1.54 (m, 2H); 3.25 (q, 2H); 7.41 (d, 1H); 8.40 (d, 1H); 8.85 (br, 1H); 13.45 (br, 1H).
Example A11




N-Methyl-2-oxo-6-(1,1,2,2-tetrafluoroethyl)-1,2-dihydropyridine-3-carboxamide
A11.1) 1-Butoxy-4,4,5,5-tetrafluoropent-1-en-3-one
With stirring and at 0° C., 25.0 g (152 mmol) of 3H-tetrafluoropropionyl chloride—dissolved in 20 ml dichloromethane—were added to a mixture of 14.4 g (182 mmol) of pyridine and 15.2 g (152 mmol) of butyl vinyl ether in 250 ml of dichloromethane. After the addition, stirring was continued at room temperature for another 15 h. 250 ml of water were then added to the mixture, and the organic phase was separated off, dried and concentrated. This gave 12.5 g (36% of theory) of a yellowish oil.
1H-NMR: [CDCl3] 0.96 (t, 3H); 1.46 (m, 2H); 1.75 (m, 2H); 4.03 (t, 2H); 6.00 (d, 1H); 6.09 (tt, 1H); 7.90 (d, 1H).
A11.2) Methyl 2-oxo-6-(1,1,2,2-tetrafluoroethyl)-1,2-dihydropyridine-3-carboxylate
After dissolution of 1.39 g (60.3 mmol) of sodium in 500 ml of methanol, 11.5 g (50.3 mmol) of 1-butoxy-4,4,5,5-tetrafluoropent-1-en-3-one and 6.07 g (50.3 mmol) of methyl malonatemonoamide were added, and the mixture was heated under reflux for 6 h. The mixture was concentrated to about 100 ml, 500 ml of 1N hydrochloric acid were then added and the mixture was subsequently extracted with ethyl acetate. Drying and concentration gave 10.3 g (67% of theory) of a yellowish resin.
1H-NMR: [CDCl3] 4.03 (s, 3H); 6.40 (tt, 1H); 7.38 (d, 1H); 8.39 (d, 1H).
A11.3) N-Methyl-2-oxo-6-(1,1,2,2-tetrafluoroethyl)-1,2-dihydropyridine-3-carb oxamide
At room temperature, 300 mg (1.19 mmol) of methyl 2-oxo-6-(1,1,2,2-tetrafluoroethyl)-1,2-dihydropyridine-3-carboxylate were stirred in 3.3 ml of a 40% strength aqueous methylamine solution for 14 h. The pH was then adjusted to 2 by addition of 1N hydrochloric acid, and the mixture was extracted with dichloromethane. Drying and concentration of the extract gave 230 mg (77% of theory) of the product.
1H-NMR: [DMSO] 2.83 (d, 3H); 6.81 (tt, 1H); 7.22 (br, 1H); 8.41 (d, 1H); 9.00 (br, 1H); 13.4 (br, 1H).
Example A12




2-Oxo-N-(2-propynyl)-6-(1,1,2,2-tetrafluoroethyl)-1,2-dihydropyridine-3-carboxamide
At room temperature, 300 mg (1.19 mmol) of methyl 2-oxo-6-(1,1,2,2-tetrafluoroethyl)-1,2-dihydropyridine-3-carboxylate were stirred in 3.3 ml (41 mmol) of propargylamine for 14 h. The pH was then adjusted to 2 by addition of 1N hydrochloric acid, and the mixture was extracted with dichloromethane. Drying and concentration of the extract gave 280 mg (85% of theory) of the product.
1H-NMR: [DMSO] 3.15 (t, 1H); 4.13 (m, 2H); 6.82 (tt, 1H); 7.18 (br, 1H); 8.41 (d, 1H); 9.35 (br, 1H); 13.3 (br, 1H).
Example A13




5-Bromo-6-(difluoromethyl)-N-(2-methoxy-1-methylethyl)-2-oxo-1,2-dihydropyridine-3-carboxamide
A13.1) Methyl 5-bromo-6-(difluoromethyl)-2-oxo-1,2-dihydropyridine-3-carboxylate
4.1 g (20 mmol) of methyl 6-(difluoromethyl)-2-oxo-1,2-dihydropyridine-3-carboxylate were dissolved in 20 ml of N,N-dimethylformamide, and 5.35 g (30 mmol) of N-bromosuccinimide were added at room temperature. After 2 hours of stirring, the reaction mixture was added to water and extracted with tert-butyl methyl ether. The extract was subsequently washed repeatedly with water. Drying and concentration finally gave 3.7 g (65% of theory) of the product.
1H-NMR: [DMSO] 3.83 (s, 3H); 7.07 (t, 1H); 8.34 (s, 1H); 12.5 (s, br, 1H).
A13.2) 5-Bromo-6-(difluoromethyl)-N-(2-methoxy-methylethyl)-2-oxo-1,2-dihydropyridine-3-carboxamide
At room temperature, 334 mg (1.19 mmol) of methyl 5-bromo-6-(difluoromethyl)-2-oxo-1,2-dihydropyridine-3-carboxylate in 3.3 ml (41 mmol) of 2-amino-1-methoxypropane were stirred for 14 h. The pH was then adjusted to 2 by addition of 1N hydrochloric acid, and the mixture was extracted with dichloromethane. Drying and concentration of the extract gave 360 mg (89% of theory) of the product.
1H-NMR: [CDCl3] 1.27 (d, 3H); 3.40 (s, 3H); 3.43 (m, 2H); 4.37 (m, 1H); 6.85 (t, 1H); 8.68 (s, 1H); 9.42 (d, br, 1H); 12.7 (br, 1H).
Example A14




5-Bromo-6-[chloro(difluoro)methyl]-N-(cyclopropylmethyl)-2-oxo-1,2-dihydropyridine-3-carboxamide
A14.1) Methyl 5-bromo-6-[chloro(difluoro)methyl]-2-oxo-1,2-dihydropyridine-3-carboxylate
1.30 g (5.47 mmol) of methyl 6-[chloro(difluoro)methyl]-2-oxo-1,2-dihydropyridinecarboxylate were dissolved in 50 ml of N,N-dimethylformamide, and 1.46 g (8.21 mmol) of N-bromosuccinimide were added at room temperature. After 3 hours of stirring, the reaction mixture was added to water, resulting in the formation of a colorless precipitate. Drying and concentration gave 1.23 g (71% of theory) of the product.
1H-NMR: [DMSO] 3.85 (s, 3H); 8.45 (s, 1H); 12.7 (s, br, 1H).
A14.2) 5-Bromo-6-[chloro(difluoro)methyl]-N-(cyclopropylmethyl)-2-oxo-1,2-dihydropyridine-3-carboxamide
At room temperature, 350 mg (1.11 mmol) of methyl 5-bromo-6-[chloro(difluoro)methyl]-2-oxo-1,2-dihydropyridine-3-carboxylate were dissolved in 5 ml of acetonitrile and stirred with 0.5 ml of aminomethylcyclopropane for 12 h. The reaction mixture was then added to 1N hydrochloric acid, and the resulting precipitate was filtered off with suction. The precipitate was dried, again triturated with 1N hydrochloric acid, filtered off with suction and washed with water. Drying gave 240 mg (62% of theory) of the product.
1H-NMR: [DMSO] 0.25 (m, 2H); 0.46 (m, 2H); 1.04 (m, 1H); 3.20 (t, 2H); 8.55 (s, 1H); 8.82 (t, br, 1H); 13.6 (br, 1H).
Example A15




6-[Chloro(difluoro)methyl]-N-(1-ethylpropyl)-5-iodo-2-oxo-1,2-dihydropyridine-3-carboxamide
A15.1) Methyl 6-[chloro(difluoro)methyl]-5-iodo-2-oxo-1,2-dihydropyridine-3-carboxylate
10.0 g (42.1 mmol) of methyl 6-[chloro(difluoro)methyl]-2-oxo-1,2-dihydropyridinecarboxylate were dissolved in 50 ml of N,N-dimethylformamide, and 6.32 g (63.1 mmol) of calcium carbonate and 20.5 g (126 mmol) of iodine chloride were added at room temperature. After 6 hours of stirring at 50° C., the reaction mixture was added to water, resulting in the formation of a colorless precipitate, which was washed with dilute sodium bisulfite solution and water. Filtration with suction and drying gave 13.6 g (89% of theory) of the product.
1H-NMR: [DMSO] 3.84 (s, 3H); 8.61 (s, 1H); 12.6 (s, br, 1H).
A15.2) 6-[Chloro(difluoro)methyl]-N-(1-ethylpropyl)-5-iodo-2-oxo-1,2-dihydropyridine-3-carboxamide
At room temperature, 400 mg (1.1 mmol) of methyl 6-[chloro(difluoro)methyl]-5-iodo-2-oxo-1,2-dihydropyridine-3-carboxylate were dissolved in 5 ml of acetonitrile and stirred with 0.5 ml of 3-pentylamine for 12 h. The reaction mixture was then added to 1N of hydrochloric acid, and the resulting precipitate was filtered off with suction and washed with water. Drying gave 370 mg (72% of theory) of the product.
1H-NMR: [DMSO] 0.87 (t, 6H); 1.43 (m, 21H); 1.55 (m, 2H); 3.78 (m, 1H); 8.55 (br, 1H); 8.67 (s, 1H); 13.5 (br, 1H).
Example A16




5-Chloro-N,N-diethyl-6-(heptafluoropropyl)-2-oxo-1,2-dihydropyridine-3-carboxamide
A16.1) Methyl 5-chloro-6-(heptafluoropropyl)-2-oxo-1,2-dihydropyridine-3-carboxylate
16.7 g (52 mmol) of methyl 6-(heptafluoropropyl)-2-oxo-1,2-dihydropyridine-3-carboxylate were dissolved in 160 ml of N,N-dimethylformamide, and 7.08 g (52 mmol) of N-chlorosuccinimide were added at room temperature. After 3 hours of stirring at 50° C., the reaction mixture was added to water and extracted repeatedly with ethyl acetate. The organic phase was then separated off, washed with water and dried. The resulting crude product was then purified by preparative RP-HPLC. This gave 10.1 g (54% of theory) of the product as a colorless powder.
1H-NMR: [DMSO] 3.85 (s, 3H); 8.35 (s, 1H); 12.8 (s, br, 1H).
A16.2) 5-Chloro-6-(heptafluoropropyl)-2-oxo-1,2-dihydropyridine-3-carboxylic acid
1.54 g (4.33 mmol) of methyl 5-chloro-6-(heptafluoropropyl)-2-oxo-1,2-dihydropyridine-3-carboxylate were dissolved in 23 ml of methanol, and a solution of 0.16 g (6.5 mmol) of lithium hydroxide in 13 ml of water was added. After two hours of heating under reflux, the methanol was distilled off, and the aqueous solution that remained was washed with dichloromethane. The aqueous phase was then acidified with 2N hydrochloric acid and extracted with dichloromethane. Drying and concentration of the extract gave 1.45 g (98% o of theory) of a brownish powder.
1H-NMR: [DMSO] 8.30 (s, 1H).
A16.3) 5-Chloro-N,N-diethyl-6-(heptafluoropropyl)-2-oxo-1,2-dihydropyridine-3-carboxamide
After dissolution of 355 mg (1.04 mmol) of 5-chloro-6-(heptafluoropropyl)-2-oxo-1,2-dihydropyridine-3-carboxylic acid in 30 ml tetrahydrofuran and addition of 337 mg (2.08 mmol) of N,N-carbonyldiimidazole, the mixture was stirred initially at room temperature for 30 min and then under reflux for 30 min. 152 mg (0.22 ml, 2.08 mmol) of diethylamine were then added, and the mixture was heated under reflux for a further 2 h. The solution was evaporated to dryness and then taken up in dichloromethane, washed with 1N hydrochloric acid and water, dried and concentrated. This gave 300 mg (72% of theory) of the product.
1H-NMR: [DMSO] 1.03 (t, 3H); 1.15 (t, 3H); 3.12 (q, 2H); 3.45 (q, 2H); 8.05 (s, 1H); 12.5 (br, 1H).
Example A17




6-(2-Chloro-1,1,2,2-tetrafluoroethyl)-N-ethyl-2-oxo-1,2-dihydropyridine-3-carboxamide
A17.1) 1-Butoxy-5-chloro-4,4,5,5-tetrafluoropent-1-en-3-one
With stirring and at 0° C., 10.0 g (50.2 mmol) of 3-chlorotetrafluoropropionyl chloride—dissolved in ml of chloroform—were added to a mixture of 3.97 g (50.2 mmol) of pyridine and 5.03 g (50.2 mmol) of butyl vinyl ether in 80 ml of chloroform. After the addition, stirring was continued at room temperature for a further 15 h. 100 ml of water were then added to the mixture, and the organic phase was separated off, dried and concentrated. This gave 10.4 g (78% of theory) of a yellowish oil.
1H-NMR: [CDCl3] 0.96 (t, 3H); 1.43 (m, 2H); 1.75 (m, 2H); 4.04 (t, 2H); 5.97 (d, 1H); 7.91 (d, 1H).
A17.2) Methyl 6-(2-chloro-1,1,2,2-tetrafluoroethyl)-2-oxo-1,2-dihydropyridine-3-carboxylate
0.32 g (13.7 mmol) of sodium were dissolved in 50 ml of methanol, 3.0 g (11.4 mmol) of 1-butoxy-5-chloro-4,4,5,5-tetrafluoropent-1-en-3-one and 1.34 g (11.4 mmol) of methyl malonatemonoamide were added and the mixture was heated under reflux for 6 h. The mixture was concentrated to about ml, 50 ml of 1N hydrochloric acid were then added and the mixture was subsequently extracted repeatedly with ethyl acetate. After drying and concentration, the resulting residue was taken up in diethyl ether and filtered. Concentration of the filtrate gave 1.74 g (52% of theory) of a yellowish powder.
1H-NMR: [DMSO] 3.84 (s, 3H); 7.44 (d, 1H); 8.32 (d, 1H); 12.4 (br, 1H).
A17.3) 6-(2-Chloro-1,1,2,2-tetrafluoroethyl)-N-ethyl-2-oxo-1,2-dihydropyridine-3-carboxamide
At room temperature, 300 mg (1.04 mmol) of methyl 6-(2-chloro-1,1,2,2-tetrafluoroethyl)-2-oxo-1,2-dihydropyridine-3-carboxylate were stirred in 5 ml of aqueous ethylamine solution (70%) for 14 h. The pH was then adjusted to 2 by addition of 1N hydrochloric acid, and the mixture was extracted with dichloromethane. Drying and concentration of the extract gave 310 mg (98% of theory) of the product.
1H-NMR: [CDCl3] 1.27 (t, 3H); 3.50 (m, 2H); 6.88 (d, 1H); 8.68 (d, 1H); 9.32 (br, 1H); 12.6 (br, 1H).
Example A18




5-Bromo-6-(2-chloro-1,1,2,2-tetrafluoroethyl)-2-oxo-1,2-dihydropyridine-3-carboxamide
A18.1) 6-(2-Chloro-1,1,2,2-tetrafluoroethyl)-2-oxo-1,2-dihydropyridine-3-carboxamide
0.53 g (22.8 mmol) of sodium were dissolved in 50 ml of methanol, 5.0 g (19.0 mmol) of 1-butoxy-5-chloro-4,4,5,5-tetrafluoropent-1-en-3-one and 2.0 g (19.0 mmol) of malonamide were then added and the mixture was heated under reflux for 6 h. The mixture was concentrated, and 1N hydrochloric acid was then added. The resulting precipitate was filtered off with suction and dried. This gave 3.8 g (73% of theory) of a brownish powder.
1H-NMR: [DMSO] 7.42 (br, 1H); 8.10 (br, 1H); 8.40 (br, 1H); 8.46 (d, 1H), 13.6 (br, 1H).
A18.2) 5-Bromo-6-(2-chloro-1,1,2,2-tetrafluoroethyl)-2-oxo-1,2-dihydropyridine-3-carboxamide
0.49 g (1.8 mmol) of 6-(2-chloro-1 μl, 2,2-tetrafluoroethyl)-2-oxo-1,2-dihydropyridine-3-carboxamide were dissolved in 5 ml of N,N-dimethylformamide, and 0.48 g (2.7 mmol) of N-bromosuccinimide was added at room temperature. After 2 hours of stirring at room temperature, the reaction mixture was poured into water, resulting in the formation of a precipitate. Filtration with suction, washing with water and drying gave 610 mg (96% of theory) of the product as a yellowish powder.
1H-NMR: [DMSO] 8.25 (br, 1H); 8.35 (br, 1H); 8.61 (s, 1H); 13.7 (br, 1H).
Example A19




6-(1 Chloro-1,2,2,2-tetrafluoroethyl)-2-oxo-1,2-dihydropyridine-3-carboxamide
A19.1) 1-Butoxy-4-chloro-4,5,5,5-tetrafluoropent-1-en-3-one
With stirring and at 0° C., 9.59 g (48.2 mmol) of 2-chlorotetrafluoropropionyl chloride were added dropwise to a mixture of 4.19 g (50.0 mmol) of pyridine and 4.83 g (48.2 mmol) of butyl vinyl ether in 75 ml of dichloromethane. After the addition, stirring was continued at room temperature for another 15 h. The mixture was then washed with 1N hydrochloric acid and 2×100 ml of water, and the organic phase was separated off, dried and concentrated. This gave 6.33 g (50% of theory) of a brown oil.
1H-NMR: [CDCl3] 0.97 (t, 3H); 1.48 (m, 2H); 1.75 (m, 2H); 4.03 (t, 2H); 5.98 (d, 1H); 7.89 (d, 1H).
A19.2) 6-(1-Chloro-1,2,2,2-tetrafluoroethyl)-2-oxo-1,2-dihydropyridine-3-carboxamide
0.33 g (14.4 mmol) of sodium were dissolved in 50 ml of methanol, 3.16 g (12.03 mmol) of 1-butoxy-4-chloro-4,5,5,5-tetrafluoropent-1-en-3-one and 1.27 g (12.03 mmol) of malonamide were added and the mixture was heated under reflux for 7 h. The mixture was concentrated, and 1N hydrochloric acid was then added. The resulting precipitate was filtered off with suction and dried. This gave 380 mg (12% of theory) of a yellowish powder.
1H-NMR: [DMSO] 7.45 (d, 1H); 8.14 (br, 1H); 8.42 (br, 1H); 8.48 (d, 1H); 13.7 (br, 1H).
In an exemplary manner, Table 1 below lists a number of compounds of the general formula (I) which can be obtained in a manner analogous to Examples A1 to A10 above and to the methods mentioned further above.
In the table:
Bu=butyl
Me=methyl
Pr=propyl
i=iso
t=tertiary
Et=ethyl
Ph=phenyl
s=secondary
c=cyclo
This applies correspondingly to composite terms such as
iPr=isopropyl
iBu=isobutyl
sBu=sec-butyl
tBu=tert-butyl
cPr=cyclopropyl
cPentyl=cyclopentyl
cHexyl=cyclohexyl
If an alkyl radical is listed in the tables without further specification, the radical in question is the straight-chain alkyl radical, i.e., for example, Bu=n-Bu=n-butyl.
In the table, the number indices in the formula are not subscript but arranged in the same line height and font size as the symbols for the atoms.
For example, the formula CF3 in the table corresponds to the formula CF3 according to the customary notation with subscript index, or the formula CH2CH(CH2CH3)2 corresponds to the formula CH2CH(CH2CH)2 with subscript indices.
For some compounds (I) in Table 1, physicochemical data (in general 1H-NMR data) are listed in Table 2. Here, the data are assigned to the compounds via the example number according to Table 1.







TABLE 1







Compounds of the formula (I)


(I)








 











Ex.
R1
R2
R3
R4














1
CF3
H
H
Me


2
CF3
H
H
Et


3
CF3
H
H
Pr


4
CF3
H
H
iPr


5
CF3
H
H
cPr


6
CF3
H
H
Bu


7
CF3
H
H
cBu


8
CF3
H
H
tBu


9
CF3
H
Me
Me


10
CF3
H
Me
Et


11
CF3
H
Me
Bu


12
CF3
H
Me
Pr


13
CF3
H
Me
iPr


14
CF3
H
Et
Et


15
CF3
H
Et
Pr


16
CF3
H
Et
iPr


17
CF3
H
Pr
Pr


18
CF3
H
H
cPentyl


19
CF3
H
H
cHexyl


20
CF3
H
H
CH2(CH2)3CH3


21
CF3
H
H
CH2(CH2)4CH3


22
CF3
H
H
CH2—cPr


23
CF3
H
H
CH2—CN


24
CF3
H
H
CH2—C(CH3)3


25
CF3
H
H
CH2CF2CF3


26
CF3
H
H
CH2CF3


27
CF3
H
H
CH2(CF2)2CF3


28
CF3
H
H
CH2CH(CH3)CH2CH3


29
CF3
H
H
CH2C(CH3)2CH2F


30
CF3
H
H
CH2CH(CH3)2


31
CF3
H
H
CH2CH(CH2CH3)2


32
CF3
H
H
CH2CH2CH(CH3)2


33
CF3
H
H
CH2CH2C(CH3)3


34
CF3
H
H
CH2CH═CH2


35
CF3
H
Me
CH2CH═CH2


36
CF3
H
CH2CH═CH2
CH2CH═CH2


37
CF3
H
H
CH2CH═CHCH3


38
CF3
H
H
CH2—C(CH3)═CH2


39
CF3
H
H
CH2—C≡CH


40
CF3
H
Me
CH2—C≡CH


41
CF3
H
H
CH(CH3)CH2CH3


42
CF3
H
H
CH(CH3)cPr


43
CF3
H
H
CH(CH3)(CH2)2CH3


44
CF3
H
H
CH(CH3)(CH2)4CH3


45
CF3
H
H
CH(CH3)(CH2)5CH3


46
CF3
H
H
CH(CH2CH3)(CH2)3CH3


47
CF3
H
H
CH(CH3)CH2CH(CH3)2


48
CF3
H
H
CH(CH3)C(CH3)3


49
CF3
H
H
CH(CH3)CH(CH3)2


50
CF3
H
H
CH(CH3)CH2CH2CH(CH3)2


51
CF3
H
H
CH(CH2CH3)2


52
CF3
H
H
C(CH3)2CH2CH3


53
CF3
H
H
C(CH3)2CH2C(CH3)3


54
CF3
H
H
CH2—CH(OMe)2


55
CF3
H
H
CH2—CH(OEt)2


56
CF3
H
H
CH2CH2—OH


57
CF3
H
H
CH2CH2—OMe


58
CF3
H
Me
CH2CH2—OMe


59
CF3
H
H
CH2CH2—OEt


60
CF3
H
H
CH2CH2—SMe


61
CF3
H
H
CH2CH2—CN


62
CF3
H
H
CH2CH2—NMe2


63
CF3
H
H
CH2CH2-morpholin-4-yl


64
CF3
H
H
CH(CH3)CH2—OMe


65
CF3
H
H
CH(CH3)CH2—NMe2


66
CF3
H
H
CH2CH2CH2—OMe


67
CF3
H
H
CH2CH2CH2—SMe


68
CF3
H
H
CH2CH2CH2—OEt


69
CF3
H
H
CH2CH2CH2—OiPr


70
CF3
H
H
CH2CH2CH2—OBu


71
CF3
H
H
CH2—COOCH3


72
CF3
H
Me
CH2—COOCH3


73
CF3
H
H
CH(CH3)COOMe


74
CF3
H
H
CH(CH3)COOEt


75
CF3
H
H
CH2CH2—COOCH3


76
CF3
H
H
CH(COOCH3)2


77
CF3
H
H
CH(COOEt)CH2—CH(CH3)2


78
CF3
H
H
CH(COOMe)CH(CH3)2


79
CF3
H
H
O—CH2CH3


80
CF3
H
Me
O—CH3


81
CF3
H
H
O—CH2CH═CH2


82
CF3
H
H
O—tBu


83
CF3
H
H
O—Pr


84
CF3
H
H
O—CH2cPr


85
CF3
H
H
O—CH2CH(CH3)2


86
CF3
H
H
O—CH2CF3


87
CF3
H
H
O—CH(CH3)cPr


88
CF3
H
H
O—CH2CH2Cl


89
CF3
H
H
O—CH2C≡CH


90
CF3
H
H
O—CH2C≡CCH3


91
CF3
H
H
O—CH(CH3)C≡CH


92
CF3
H
H
CH2—Ph


93
CF3
H
Me
CH2—Ph


94
CF3
H
H
CH2-pyridin-3-yl


95
CF3
H
H
CH2-6-Cl-pyridin-3-yl


96
CF3
H
H
CH(CH3)Ph


97
CF3
H
H
CH2CH2—Ph


98
CF3
H
H
CH2-2-CF3—Ph


99
CF3
H
H
CH2CH2CHPh2










100
CF3
H
morpholin-4-yl


101
CF3
H
piperidin-1-yl


102
CF3
H
thiazolidin-3-yl


103
CF3
H
pyrrolidin-1-yl


104
CF3
H
2-methylpyrrolidin-1-yl


105
CF3
H
═CH—N(CH3)2


106
CF3
H
═C(CH3)N(CH3)2


107
CF3
H
═CH—N(C2H5)2


108
CF3
H
═C(CH3)N(C2H5)2


109
CF3
H
═CH-piperidine


110
CF3
H
═CH-morpholine


111
CF3
H
═CH-pyrrolidine











112
CF3
H
H
indan-1-yl


113
CF3
H
H
tetrahydrofuran-2-ylmethyl


114
CF2Cl
H
H
H


115
CF2Cl
H
H
Me


116
CF2Cl
H
H
Et


117
CF2Cl
H
H
Pr


118
CF2Cl
H
H
iPr


119
CF2Cl
H
H
cPr


120
CF2Cl
H
H
Bu


121
CF2Cl
H
H
cBu


122
CF2Cl
H
H
tBu


123
CF2Cl
H
Me
Me


124
CF2Cl
H
Me
Et


125
CF2Cl
H
Me
Bu


126
CF2Cl
H
Me
Pr


127
CF2Cl
H
Me
iPr


128
CF2Cl
H
Et
Et


129
CF2Cl
H
Et
Pr


130
CF2Cl
H
Et
iPr


131
CF2Cl
H
Pr
Pr


132
CF2Cl
H
H
cPentyl


133
CF2Cl
H
H
cHexyl


134
CF2Cl
H
H
CH2(CH2)3CH3


135
CF2Cl
H
H
CH2(CH2)4CH3


136
CF2Cl
H
H
CH2—cPr


137
CF2Cl
H
H
CH2—CN


138
CF2Cl
H
H
CH2—C(CH3)3


139
CF2Cl
H
H
CH2CF2CF3


140
CF2Cl
H
H
CH2CF3


141
CF2Cl
H
H
CH2(CF2)2CF3


142
CF2Cl
H
H
CH2CH(CH3)CH2CH3


143
CF2Cl
H
H
CH2C(CH3)2CH2F


144
CF2Cl
H
H
CH2CH(CH3)2


145
CF2Cl
H
H
CH2CH(CH2CH3)2


146
CF2Cl
H
H
CH2CH2CH(CH3)2


147
CF2Cl
H
H
CH2CH2C(CH3)3


148
CF2Cl
H
H
CH2CH═CH2


149
CF2Cl
H
Me
CH2CH═CH2


150
CF2Cl
H
CH2CH═CH2
CH2CH═CH2


151
CF2Cl
H
H
CH2CH═CHCH3


152
CF2Cl
H
H
CH2—C(CH3)═CH2


153
CF2Cl
H
H
CH2—C≡CH


154
CF2Cl
H
Me
CH2—C≡CH


155
CF2Cl
H
H
CH(CH3)CH2CH3


156
CF2Cl
H
H
CH(CH3)cPr


157
CF2Cl
H
H
CH(CH3)(CH2)2CH3


158
CF2Cl
H
H
CH(CH3)(CH2)4CH3


159
CF2Cl
H
H
CH(CH3)(CH3)5CH3


160
CF2Cl
H
H
CH(CH2CH3)(CH2)3CH3


161
CF2Cl
H
H
CH(CH3)CH2CH(CH3)2


162
CF2Cl
H
H
CH(CH3)C(CH3)3


163
CF2Cl
H
H
CH(CH3)CH(CH3)2


164
CF2Cl
H
H
CH(CH3)CH2CH2CH(CH3)2


165
CF2Cl
H
H
CH(CH2CH3)2


166
CF2Cl
H
H
C(CH3)2CH2CH3


167
CF2Cl
H
H
C(CH3)2CH2C(CH3)3


168
CF2Cl
H
H
CH2—CH(OMe)2


169
CF2Cl
H
H
CH2—CH(OEt)2


170
CF2Cl
H
H
CH2CH2—OH


171
CF2Cl
H
H
CH2CH2—OMe


172
CF2Cl
H
Me
CH2CH2—OMe


173
CF2Cl
H
H
CH2CH2—OEt


174
CF2Cl
H
H
CH2CH2—SMe


175
CF2Cl
H
H
CH2CH2—CN


176
CF2Cl
H
H
CH2CH2—NMe2


177
CF2Cl
H
H
CH2CH2-morpholin-4-yl


178
CF2Cl
H
H
CH(CH3)CH2—OMe


179
CF2Cl
H
H
CH(CH3)CH2—NMe2


180
CF2Cl
H
H
CH2CH2CH2—OMe


181
CF2Cl
H
H
CH2CH2CH2—SMe


182
CF2Cl
H
H
CH2CH2CH2—OEt


183
CF2Cl
H
H
CH2CH2CH2—OiPr


184
CF2Cl
H
H
CH2CH2CH2—OBu


185
CF2Cl
H
H
CH2—COOCH3


186
CF2Cl
H
Me
CH2—COOCH3


187
CF2Cl
H
H
CH(CH3)COOMe


188
CF2Cl
H
H
CH(CH3)COOEt


189
CF2Cl
H
H
CH2CH2—COOCH3


190
CF2Cl
H
H
CH(COOCH3)2


191
CF2Cl
H
H
CH(COOEt)CH2—CH(CH3)2


192
CF2Cl
H
H
CH(COOMe)CH(CH3)2


193
CF2Cl
H
H
O—CH2CH3


194
CF2Cl
H
H
O—CH3


195
CF2Cl
H
H
O—CH2CH═CH2


196
CF2Cl
H
H
O—tBu


197
CF2Cl
H
H
O—Pr


198
CF2Cl
H
H
O—CH2cPr


199
CF2Cl
H
H
O—CH2CH(CH3)2


200
CF2Cl
H
H
O—CH2CF3


201
CF2Cl
H
H
O—CH(CH3)cPr


202
CF2Cl
H
H
O—CH2CH2Cl


203
CF2Cl
H
H
O—CH2C≡CH


204
CF2Cl
H
H
O—CH2C≡CCH3


205
CF2Cl
H
H
O—CH(CH3)C≡CH


206
CF2Cl
H
H
CH2—Ph


207
CF2Cl
H
Me
CH2—Ph


208
CF2Cl
H
H
CH2-pyridin-3-yl


209
CF2Cl
H
H
CH2-6-Cl-pyridin-3-yl


210
CF2Cl
H
H
CH(CH3)Ph


211
CF2Cl
H
H
CH2CH2—Ph


212
CF2Cl
H
H
CH2-2-CF3—Ph


213
CF2Cl
H
H
CH2CH2CHPh










214
CF2Cl
H
morpholin-4-yl


215
CF2Cl
H
piperidin-1-yl


216
CF2Cl
H
thiazolidin-3-yl


217
CF2Cl
H
pyrrolidin-1-yl


218
CF2Cl
H
2-methylpyrrolidin-1-yl


219
CF2Cl
H
═CH—N(CH3)2


220
CF2Cl
H
═C(CH3)N(CH3)2


221
CF2Cl
H
═CH—N(C2H5)2


222
CF2Cl
H
═C(CH3)N(C2H5)2


223
CF2Cl
H
═CH-piperidine


224
CF2Cl
H
═CH-morpholine


225
CF2Cl
H
═CH-pyrrolidine











226
CF2Cl
H
H
indan-1-yl


227
CF2Cl
H
H
tetrahydrofuran-2-ylmethyl


228
CHF2
H
H
H


229
CHF2
H
H
Me


230
CHF2
H
H
Et


231
CHF2
H
H
Pr


232
CHF2
H
H
iPr


233
CHF2
H
H
cPr


234
CHF2
H
H
Bu


235
CHF2
H
H
cBu


236
CHF2
H
H
tBu


237
CHF2
H
Me
Me


238
CHF2
H
Me
Et


239
CHF2
H
Me
Bu


240
CHF2
H
Me
Pr


241
CHF2
H
Me
iPr


242
CHF2
H
Et
Et


243
CHF2
H
Et
Pr


244
CHF2
H
Et
iPr


245
CHF2
H
Pr
Pr


246
CHF2
H
H
cPentyl


247
CHF2
H
H
cHexyl


248
CHF2
H
H
CH2(CH2)3CH3


249
CHF2
H
H
CH2(CH2)4CH3


250
CHF2
H
H
CH2—cPr


251
CHF2
H
H
CH2—CN


252
CHF2
H
H
CH2—C(CH3)3


253
CHF2
H
H
CH2CF2CF3


254
CHF2
H
H
CH2CF3


255
CHF2
H
H
CH2(CF2)2CF3


256
CHF2
H
H
CH2CH(CH3)CH2CH3


257
CHF2
H
H
CH2C(CH3)2CH2F


258
CHF2
H
H
CH2CH(CH3)2


259
CHF2
H
H
CH2CH(CH2CH3)2


260
CHF2
H
H
CH2CH2CH(CH3)2


261
CHF2
H
H
CH2CH2C(CH3)3


262
CHF2
H
H
CH2CH═CH2


263
CHF2
H
Me
CH2CH═CH2


264
CHF2
H
CH2CH═CH2
CH2CH═CH2


265
CHF2
H
H
CH2CH═CHCH3


266
CHF2
H
H
CH2—C(CH3)═CH2


267
CHF2
H
H
CH2—C≡CH


268
CHF2
H
Me
CH2—C≡CH


269
CHF2
H
H
CH(CH3)CH2CH3


270
CHF2
H
H
CH(CH3)cPr


271
CHF2
H
H
CH(CH3)(CH2)2CH3


272
CHF2
H
H
CH(CH3)(CH2)4CH3


273
CHF2
H
H
CH(CH3)(CH2)5CH3


274
CHF2
H
H
CH(CH2CH3)(CH2)3CH3


275
CHF2
H
H
CH(CH3)CH2CH(CH3)2


276
CHF2
H
H
CH(CH3)C(CH3)3


277
CHF2
H
H
CH(CH3)CH(CH3)2


278
CHF2
H
H
CH(CH3)CH2CH2CH(CH3)2


279
CHF2
H
H
CH(CH2CH3)2


280
CHF2
H
H
C(CH3)2CH2CH3


281
CHF2
H
H
C(CH3)2CH2C(CH3)3


282
CHF2
H
H
CH2—CH(OMe)2


283
CHF2
H
H
CH2—CH(OEt)2


284
CHF2
H
H
CH2CH2—OH


285
CHF2
H
H
CH2CH2—OMe


286
CHF2
H
H
CH2CH2—OEt


287
CHF2
H
H
CH2CH2—SMe


288
CHF2
H
H
CH2CH2—CN


289
CHF2
H
H
CH2CH2—NMe2


290
CHF2
H
H
CH2CH2-morpholin-4-yl


291
CHF2
H
H
CH(CH3)CH2—OMe


292
CHF2
H
H
CH(CH3)CH2—NMe2


293
CHF2
H
H
CH2CH2CH2—OMe


294
CHF2
H
H
CH2CH2CH2—SMe


295
CHF2
H
H
CH2CH2CH2—OEt


296
CHF2
H
H
CH2CH2CH2—OiPr


297
CHF2
H
H
CH2CH2CH2—OBu


298
CHF2
H
H
CH2—COOCH3


299
CHF2
H
Me
CH2—COOCH3


300
CHF2
H
H
CH(CH3)COOMe


301
CHF2
H
H
CH(CH3)COOEt


302
CHF2
H
H
CH2CH2—COOCH3


303
CHF2
H
H
CH(COOCH3)2


304
CHF2
H
H
CH(COOEt)CH2—CH(CH3)2


305
CHF2
H
H
CH(COOMe)CH(CH3)2


306
CHF2
H
H
O—CH2CH3


307
CHF2
H
H
O—CH3


308
CHF2
H
H
O—CH2CH═CH2


309
CHF2
H
H
O—tBu


310
CHF2
H
H
O—Pr


311
CHF2
H
H
O—CH2cPr


312
CHF2
H
H
O—CH2CH(CH3)2


313
CHF2
H
H
O—CH2CF3


314
CHF2
H
H
O—CH(CH3)cPr


315
CHF2
H
H
O—CH2CH2Cl


316
CHF2
H
H
O—CH2C≡CH


317
CHF2
H
H
O—CH2C≡CCH3


318
CHF2
H
H
O—CH(CH3)C≡CH


319
CHF2
H
H
CH2—Ph


320
CHF2
H
Me
CH2—Ph


321
CHF2
H
H
CH2-pyridin-3-yl


322
CHF2
H
H
CH2-6-Cl-pyridin-3-yl


323
CHF2
H
H
CH(CH3)Ph


324
CHF2
H
H
CH2CH2—Ph


325
CHF2
H
H
CH2-2-CF3—Ph


326
CHF2
H
H
CH2CH2CHPh










327
CHF2
H
morpholin-4-yl


328
CHF2
H
piperidin-1-yl


329
CHF2
H
thiazolidin-3-yl


330
CHF2
H
pyrrolidin-1-yl


331
CHF2
H
2-methylpyrrolidin-1-yl


332
CHF2
H
═CH—N(CH3)2


333
CHF2
H
═C(CH3)N(CH3)2


334
CHF2
H
═CH—N(C2H5)2


335
CHF2
H
═C(CH3)N(C2H5)2


336
CHF2
H
═CH-piperidine


337
CHF2
H
═CH-morpholine


338
CHF2
H
═CH-pyrrolidine











339
CHF2
H
H
indan-1-yl


340
CHF2
H
H
tetrahydrofuran-2-ylmethyl


341
CF2CF3
H
H
H


342
CF2CF3
H
H
Me


343
CF2CF3
H
H
Et


344
CF2CF3
H
H
Pr


345
CF2CF3
H
H
iPr


346
CF2CF3
H
H
cPr


347
CF2CF3
H
H
Bu


348
CF2CF3
H
H
cBu


349
CF2CF3
H
H
tBu


350
CF2CF3
H
Me
Me


351
CF2CF3
H
Me
Et


352
CF2CF3
H
Me
Bu


353
CF2CF3
H
Me
Pr


354
CF2CF3
H
Me
iPr


355
CF2CF3
H
Et
Et


356
CF2CF3
H
Et
Pr


357
CF2CF3
H
Et
iPr


358
CF2CF3
H
Pr
Pr


359
CF2CF3
H
H
cPentyl


360
CF2CF3
H
H
cHexyl


361
CF2CF3
H
H
CH2(CH2)3CH3


362
CF2CF3
H
H
CH2(CH2)4CH3


363
CF2CF3
H
H
CH2—cPr


364
CF2CF3
H
H
CH2—CN


365
CF2CF3
H
H
CH2—C(CH3)3


366
CF2CF3
H
H
CH2CF2CF3


367
CF2CF3
H
H
CH2CF3


368
CF2CF3
H
H
CH2(CF2)2CF3


369
CF2CF3
H
H
CH2CH(CH3)CH2CH3


370
CF2CF3
H
H
CH2C(CH3)2CH2F


371
CF2CF3
H
H
CH2CH(CH3)2


372
CF2CF3
H
H
CH2CH(CH2CH3)2


373
CF2CF3
H
H
CH2CH2CH(CH3)2


374
CF2CF3
H
H
CH2CH2C(CH3)3


375
CF2CF3
H
H
CH2CH═CH2


376
CF2CF3
H
Me
CH2CH═CH2


377
CF2CF3
H
CH2CH═CH2
CH2CH═CH2


378
CF2CF3
H
H
CH2CH═CHCH3


379
CF2CF3
H
H
CH2—C(CH3)═CH2


380
CF2CF3
H
H
CH2—C≡CH


381
CF2CF3
H
Me
CH2—C≡CH


382
CF2CF3
H
H
CH(CH3)CH2CH3


383
CF2CF3
H
H
CH(CH3)cPr


384
CF2CF3
H
H
CH(CH3)(CH2)2CH3


385
CF2CF3
H
H
CH(CH3)(CH2)4CH3


386
CF2CF3
H
H
CH(CH3)(CH2)5CH3


387
CF2CF3
H
H
CH(CH2CH3)(CH2)3CH3


388
CF2CF3
H
H
CH(CH3)CH2CH(CH3)2


389
CF2CF3
H
H
CH(CH3)C(CH3)3


390
CF2CF3
H
H
CH(CH3)CH(CH3)2


391
CF2CF3
H
H
CH(CH3)CH2CH2CH(CH3)2


392
CF2CF3
H
H
CH(CH2CH3)2


393
CF2CF3
H
H
C(CH3)2CH2CH3


394
CF2CF3
H
H
C(CH3)2CH2C(CH3)3


395
CF2CF3
H
H
CH2—CH(OMe)2


396
CF2CF3
H
H
CH2—CH(OEt)2


397
CF2CF3
H
H
CH2CH2—OH


398
CF2CF3
H
H
CH2CH2—OMe


399
CF2CF3
H
Me
CH2CH2—OMe


400
CF2CF3
H
H
CH2CH2—OEt


401
CF2CF3
H
H
CH2CH2—SMe


402
CF2CF3
H
H
CH2CH2—CN


403
CF2CF3
H
H
CH2CH2—NMe2


404
CF2CF3
H
H
CH2CH2-morpholin-4-yl


405
CF2CF3
H
H
CH(CH3)CH2—OMe


406
CF2CF3
H
H
CH(CH3)CH2—NMe2


407
CF2CF3
H
H
CH2CH2CH2—OMe


408
CF2CF3
H
H
CH2CH2CH2—SMe


409
CF2CF3
H
H
CH2CH2CH2—OEt


410
CF2CF3
H
H
CH2CH2CH2—OiPr


411
CF2CF3
H
H
CH2CH2CH2—OBu


412
CF2CF3
H
H
CH2—COOCH3


413
CF2CF3
H
Me
CH2—COOCH3


414
CF2CF3
H
H
CH(CH3)COOMe


415
CF2CF3
H
H
CH(CH3)COOEt


416
CF2CF3
H
H
CH2CH2—COOCH3


417
CF2CF3
H
H
CH(COOCH3)2


418
CF2CF3
H
H
CH(COOEt)CH2—CH(CH3)2


419
CF2CF3
H
H
CH(COOMe)CH(CH3)2


420
CF2CF3
H
H
O—CH2CH3


421
CF2CF3
H
H
O—CH3


422
CF2CF3
H
H
O—CH2CH═CH2


423
CF2CF3
H
H
O—tBu


424
CF2CF3
H
H
O—Pr


425
CF2CF3
H
H
O—CH2cPr


426
CF2CF3
H
H
O—CH2CH(CH3)2


427
CF2CF3
H
H
O—CH2CF3


428
CF2CF3
H
H
O—CH(CH3)cPr


429
CF2CF3
H
H
O—CH2CH2Cl


430
CF2CF3
H
H
O—CH2C≡CH


431
CF2CF3
H
H
O—CH2C≡CCH3


432
CF2CF3
H
H
O—CH(CH3)C≡CH


433
CF2CF3
H
H
CH2—Ph


434
CF2CF3
H
Me
CH2—Ph


435
CF2CF3
H
H
CH2-pyridin-3-yl


436
CF2CF3
H
H
CH2-6-Cl-pyridin-3-yl


437
CF2CF3
H
H
CH(CH3)Ph


438
CF2CF3
H
H
CH2CH2—Ph


439
CF2CF3
H
H
CH2-2-CF3—Ph


440
CF2CF3
H
H
CH2CH2CHPh










441
CF2CF3
H
morpholin-4-yl


442
CF2CF3
H
piperidin-1-yl


443
CF2CF3
H
thiazolidin-3-yl


444
CF2CF3
H
pyrrolidin-1-yl


445
CF2CF3
H
2-methylpyrrolidin-1-yl


446
CF2CF3
H
═CH—N(CH3)2


447
CF2CF3
H
═C(CH3)N(CH3)2


448
CF2CF3
H
═CH—N(C2H5)2


449
CF2CF3
H
═C(CH3)N(C2H5)2


450
CF2CF3
H
═CH-piperidine


451
CF2CF3
H
═CH-morpholine


452
CF2CF3
H
═CH-pyrrolidine











453
CF2CF3
H
H
indan-1-yl


454
CF2CF3
H
H
tetrahydrofuran-2-ylmethyl


455
CF3
Cl
H
H


456
CF3
Cl
H
Me


457
CF3
Cl
H
Et


458
CF3
Cl
H
Pr


459
CF3
Cl
H
iPr


460
CF3
Cl
H
cPr


461
CF3
Cl
H
Bu


462
CF3
Cl
H
cBu


463
CF3
Cl
H
tBu


464
CF3
Cl
Me
Me


465
CF3
Cl
Me
Et


466
CF3
Cl
Me
Bu


467
CF3
Cl
Me
Pr


468
CF3
Cl
Me
iPr


469
CF3
Cl
Et
Et


470
CF3
Cl
Et
Pr


471
CF3
Cl
Et
iPr


472
CF3
Cl
Pr
Pr


473
CF3
Cl
H
cPentyl


474
CF3
Cl
H
cHexyl


475
CF3
Cl
H
CH2(CH2)3CH3


476
CF3
Cl
H
CH2(CH2)4CH3


477
CF3
Cl
H
CH2—cPr


478
CF3
Cl
H
CH2—CN


479
CF3
Cl
H
CH2—C(CH3)3


480
CF3
Cl
H
CH2CF2CF3


481
CF3
Cl
H
CH2CF3


482
CF3
Cl
H
CH2(CF2)2CF3


483
CF3
Cl
H
CH2CH(CH3)CH2CH3


484
CF3
Cl
H
CH2C(CH3)2CH2F


485
CF3
Cl
H
CH2CH(CH3)2


486
CF3
Cl
H
CH2CH(CH2CH3)2


487
CF3
Cl
H
CH2CH2CH(CH3)2


488
CF3
Cl
H
CH2CH2C(CH3)3


489
CF3
Cl
H
CH2CH═CH2


490
CF3
Cl
Me
CH2CH═CH2


491
CF3
Cl
CH2CH═CH2
CH2CH═CH2


492
CF3
Cl
H
CH2CH═CHCH3


493
CF3
Cl
H
CH2—C(CH3)═CH2


494
CF3
Cl
H
CH2—C≡CH


495
CF3
Cl
Me
CH2—C≡CH


496
CF3
Cl
H
CH(CH3)CH2CH3


497
CF3
Cl
H
CH(CH3)cPr


498
CF3
Cl
H
CH(CH3)(CH2)2CH3


499
CF3
Cl
H
CH(CH3)(CH2)4CH3


500
CF3
Cl
H
CH(CH3)(CH2)5CH3


501
CF3
Cl
H
CH(CH2CH3)(CH2)3CH3


502
CF3
Cl
H
CH(CH3)CH2CH(CH3)2


503
CF3
Cl
H
CH(CH3)C(CH3)3


504
CF3
Cl
H
CH(CH3)CH(CH3)2


505
CF3
Cl
H
CH(CH3)CH2CH2CH(CH3)2


506
CF3
Cl
H
CH(CH2CH3)2


507
CF3
Cl
H
C(CH3)2CH2CH3


508
CF3
Cl
H
C(CH3)2CH2C(CH3)3


509
CF3
Cl
H
CH2—CH(OMe)2


510
CF3
Cl
H
CH2—CH(OEt)2


511
CF3
Cl
H
CH2CH2—OH


512
CF3
Cl
H
CH2CH2—OMe


513
CF3
Cl
Me
CH2CH2—OMe


514
CF3
Cl
H
CH2CH2—OEt


515
CF3
Cl
H
CH2CH2—SMe


516
CF3
Cl
H
CH2CH2—CN


517
CF3
Cl
H
CH2CH2—NMe2


518
CF3
Cl
H
CH2CH2-morpholin-4-yl


519
CF3
Cl
H
CH(CH3)CH2—OMe


520
CF3
Cl
H
CH(CH3)CH2—NMe2


521
CF3
Cl
H
CH2CH2CH2—OMe


522
CF3
Cl
H
CH2CH2CH2—SMe


523
CF3
Cl
H
CH2CH2CH2—OEt


524
CF3
Cl
H
CH2CH2CH2—OiPr


525
CF3
Cl
H
CH2CH2CH2—OBu


526
CF3
Cl
H
CH2—COOCH3


527
CF3
Cl
Me
CH2—COOCH3


528
CF3
Cl
H
CH(CH3)COOMe


529
CF3
Cl
H
CH(CH3)COOEt


530
CF3
Cl
H
CH2CH2—COOCH3


531
CF3
Cl
H
CH(COOCH3)2


532
CF3
Cl
H
CH(COOEt)CH2—CH(CH3)2


533
CF3
Cl
H
CH(COOMe)CH(CH3)2


534
CF3
Cl
H
O—CH2CH3


535
CF3
Cl
Me
O—CH3


536
CF3
Cl
H
O—CH2CH═CH2


537
CF3
Cl
H
O—tBu


538
CF3
Cl
H
O—Pr


539
CF3
Cl
H
O—CH2cPr


540
CF3
Cl
H
O—CH2CH(CH3)2


541
CF3
Cl
H
O—CH2CF3


542
CF3
Cl
H
O—CH(CH3)cPr


543
CF3
Cl
H
O—CH2CH2Cl


544
CF3
Cl
H
O—CH2C≡CH


545
CF3
Cl
H
O—CH2C≡CCH3


546
CF3
Cl
H
O—CH(CH3)C≡CH


547
CF3
Cl
H
CH2—Ph


548
CF3
Cl
Me
CH2—Ph


549
CF3
Cl
H
CH2-pyridin-3-yl


550
CF3
Cl
H
CH2-6-Cl-pyridin-3-yl


551
CF3
Cl
H
CH(CH3)Ph


552
CF3
Cl
H
CH2CH2—Ph


553
CF3
Cl
H
CH2-2-CF3—Ph


554
CF3
Cl
H
CH2CH2CHPh










555
CF3
Cl
morpholin-4-yl


556
CF3
Cl
piperidin-1-yl


557
CF3
Cl
thiazolidin-3-yl


558
CF3
Cl
pyrrolidin-1-yl


559
CF3
Cl
2-methylpyrrolidin-1-yl


560
CF3
Cl
═CH—N(CH3)2


561
CF3
Cl
═C(CH3)N(CH3)2


562
CF3
Cl
═CH—N(C2H5)2


563
CF3
Cl
═C(CH3)N(C2H5)2


564
CF3
Cl
═CH-piperidine


565
CF3
Cl
═CH-morpholine


566
CF3
Cl
═CH-pyrrolidine











567
CF3
Cl
H
indan-1-yl


568
CF3
Cl
H
tetrahydrofuran-2-ylmethyl


569
CF2Cl
Cl
H
H


570
CF2Cl
Cl
H
Me


571
CF2Cl
Cl
H
Et


572
CF2Cl
Cl
H
Pr


573
CF2Cl
Cl
H
iPr


574
CF2Cl
Cl
H
cPr


575
CF2Cl
Cl
H
Bu


576
CF2Cl
Cl
H
cBu


577
CF2Cl
Cl
H
tBu


578
CF2Cl
Cl
Me
Me


579
CF2Cl
Cl
Me
Et


580
CF2Cl
Cl
Me
Bu


581
CF2Cl
Cl
Me
Pr


582
CF2Cl
Cl
Me
iPr


583
CF2Cl
Cl
Et
Et


584
CF2Cl
Cl
Et
Pr


585
CF2Cl
Cl
Et
iPr


586
CF2Cl
Cl
Pr
Pr


587
CF2Cl
Cl
H
cPentyl


588
CF2Cl
Cl
H
cHexyl


589
CF2Cl
Cl
H
CH2(CH2)3CH3


590
CF2Cl
Cl
H
CH2(CH2)4CH3


591
CF2Cl
Cl
H
CH2—cPr


592
CF2Cl
Cl
H
CH2—CN


593
CF2Cl
Cl
H
CH2—C(CH3)3


594
CF2Cl
Cl
H
CH2CF2CF3


595
CF2Cl
Cl
H
CH2CF3


596
CF2Cl
Cl
H
CH2(CF2)2CF3


597
CF2Cl
Cl
H
CH2CH(CH3)CH2CH3


598
CF2Cl
Cl
H
CH2C(CH3)2CH2F


599
CF2Cl
Cl
H
CH2CH(CH3)2


600
CF2Cl
Cl
H
CH2CH(CH2CH3)2


601
CF2Cl
Cl
H
CH2CH2CH(CH3)2


602
CF2Cl
Cl
H
CH2CH2C(CH3)3


603
CF2Cl
Cl
H
CH2CH═CH2


604
CF2Cl
Cl
Me
CH2CH═CH2


605
CF2Cl
Cl
CH2CH═CH2
CH2CH═CH2


606
CF2Cl
Cl
H
CH2CH═CHCH3


607
CF2Cl
Cl
H
CH2—C(CH3)═CH2


608
CF2Cl
Cl
H
CH2—C≡CH


609
CF2Cl
Cl
Me
CH2—C≡CH


610
CF2Cl
Cl
H
CH(CH3)CH2CH3


611
CF2Cl
Cl
H
CH(CH3)cPr


612
CF2Cl
Cl
H
CH(CH3)(CH2)2CH3


613
CF2Cl
Cl
H
CH(CH3)(CH2)4CH3


614
CF2Cl
Cl
H
CH(CH3)(CH2)5CH3


615
CF2Cl
Cl
H
CH(CH2CH3)(CH2)3CH3


616
CF2Cl
Cl
H
CH(CH3)CH2CH(CH3)2


617
CF2Cl
Cl
H
CH(CH3)C(CH3)3


618
CF2Cl
Cl
H
CH(CH3)CH(CH3)2


619
CF2Cl
Cl
H
CH(CH3)CH2CH2CH(CH3)2


620
CF2Cl
Cl
H
CH(CH2CH3)2


621
CF2Cl
Cl
H
C(CH3)2CH2CH3


622
CF2Cl
Cl
H
C(CH3)2CH2C(CH3)3


623
CF2Cl
Cl
H
CH2—CH(OMe)2


624
CF2Cl
Cl
H
CH2—CH(OEt)2


625
CF2Cl
Cl
H
CH2CH2—OH


626
CF2Cl
Cl
H
CH2CH2—OMe


627
CF2Cl
Cl
Me
CH2CH2—OMe


628
CF2Cl
Cl
H
CH2CH2—OEt


629
CF2Cl
Cl
H
CH2CH2—SMe


630
CF2Cl
Cl
H
CH2CH2—CN


631
CF2Cl
Cl
H
CH2CH2—NMe2


632
CF2Cl
Cl
H
CH2CH2-morpholin-4-yl


633
CF2Cl
Cl
H
CH(CH3)CH2—OMe


634
CF2Cl
Cl
H
CH(CH3)CH2—NMe2


635
CF2Cl
Cl
H
CH2CH2CH2—OMe


636
CF2Cl
Cl
H
CH2CH2CH2—SMe


637
CF2Cl
Cl
H
CH2CH2CH2—OEt


638
CF2Cl
Cl
H
CH2CH2CH2—OiPr


639
CF2Cl
Cl
H
CH2CH2CH2—OBu


640
CF2Cl
Cl
H
CH2—COOCH3


641
CF2Cl
Cl
Me
CH2—COOCH3


642
CF2Cl
Cl
H
CH(CH3)COOMe


643
CF2Cl
Cl
H
CH(CH3)COOEt


644
CF2Cl
Cl
H
CH2CH2—COOCH3


645
CF2Cl
Cl
H
CH(COOCH3)2


646
CF2Cl
Cl
H
CH(COOEt)CH2—CH(CH3)2


647
CF2Cl
Cl
H
CH(COOMe)CH(CH3)2


648
CF2Cl
Cl
H
O—CH2CH3


649
CF2Cl
Cl
H
O—CH3


650
CF2Cl
Cl
H
O—CH2CH═CH2


651
CF2Cl
Cl
H
O—tBu


652
CF2Cl
Cl
H
O—Pr


653
CF2Cl
Cl
H
O—CH2cPr


654
CF2Cl
Cl
H
O—CH2CH(CH3)2


655
CF2Cl
Cl
H
O—CH2CF3


656
CF2Cl
Cl
H
O—CH(CH3)cPr


657
CF2Cl
Cl
H
O—CH2CH2Cl


658
CF2Cl
Cl
H
O—CH2C≡CH


659
CF2Cl
Cl
H
O—CH2C≡CCH3


660
CF2Cl
Cl
H
O—CH(CH3)C≡CH


661
CF2Cl
Cl
H
CH2—Ph


662
CF2Cl
Cl
Me
CH2—Ph


663
CF2Cl
Cl
H
CH2-pyridin-3-yl


664
CF2Cl
Cl
H
CH2-6-Cl-pyridin-3-yl


665
CF2Cl
Cl
H
CH(CH3)Ph


666
CF2Cl
Cl
H
CH2CH2—Ph


667
CF2Cl
Cl
H
CH2-2-CF3—Ph


668
CF2Cl
Cl
H
CH2CH2CHPh










669
CF2Cl
Cl
morpholin-4-yl


670
CF2Cl
Cl
piperidin-1-yl


671
CF2Cl
Cl
thiazolidin-3-yl


672
CF2Cl
Cl
pyrrolidin-1-yl


673
CF2Cl
Cl
2-methylpyrrolidin-1-yl


674
CF2Cl
Cl
═CH—N(CH3)2


675
CF2Cl
Cl
═C(CH3)N(CH3)2


676
CF2Cl
Cl
═CH—N(C2H5)2


677
CF2Cl
Cl
═C(CH3)N(C2H5)2


678
CF2Cl
Cl
═CH-piperidine


679
CF2Cl
Cl
═CH-morpholine


680
CF2Cl
Cl
═CH-pyrrolidine











681
CF2Cl
Cl
H
indan-1-yl


682
CF2Cl
Cl
H
tetrahydrofuran-2-ylmethyl


683
CHF2
Cl
H
H


684
CHF2
Cl
H
Me


685
CHF2
Cl
H
Et


686
CHF2
Cl
H
Pr


687
CHF2
Cl
H
iPr


688
CHF2
Cl
H
cPr


689
CHF2
Cl
H
Bu


690
CHF2
Cl
H
cBu


691
CHF2
Cl
H
tBu


692
CHF2
Cl
Me
Me


693
CHF2
Cl
Me
Et


694
CHF2
Cl
Me
Bu


695
CHF2
Cl
Me
Pr


696
CHF2
Cl
Me
iPr


697
CHF2
Cl
Et
Et


698
CHF2
Cl
Et
Pr


699
CHF2
Cl
Et
iPr


700
CHF2
Cl
Pr
Pr


701
CHF2
Cl
H
cPentyl


702
CHF2
Cl
H
cHexyl


703
CHF2
Cl
H
CH2(CH2)3CH3


704
CHF2
Cl
H
CH2(CH2)4CH3


705
CHF2
Cl
H
CH2—cPr


706
CHF2
Cl
H
CH2—CN


707
CHF2
Cl
H
CH2—C(CH3)3


708
CHF2
Cl
H
CH2CF2CF3


709
CHF2
Cl
H
CH2CF3


710
CHF2
Cl
H
CH2(CF2)2CF3


711
CHF2
Cl
H
CH2CH(CH3)CH2CH3


712
CHF2
Cl
H
CH2C(CH3)2CH2F


713
CHF2
Cl
H
CH2CH(CH3)2


714
CHF2
Cl
H
CH2CH(CH2CH3)2


715
CHF2
Cl
H
CH2CH2CH(CH3)2


716
CHF2
Cl
H
CH2CH2C(CH3)3


717
CHF2
Cl
H
CH2CH═CH2


718
CHF2
Cl
Me
CH2CH═CH2


719
CHF2
Cl
CH2CH═CH2
CH2CH═CH2


720
CHF2
Cl
H
CH2CH═CHCH3


721
CHF2
Cl
H
CH2—C(CH3)═CH2


722
CHF2
Cl
H
CH2—C≡CH


723
CHF2
Cl
Me
CH2—C≡CH


724
CHF2
Cl
H
CH(CH3)CH2CH3


725
CHF2
Cl
H
CH(CH3)cPr


726
CHF2
Cl
H
CH(CH3)(CH2)2CH3


727
CHF2
Cl
H
CH(CH3)(CH2)4CH3


728
CHF2
Cl
H
CH(CH3)(CH2)5CH3


729
CHF2
Cl
H
CH(CH2CH3)(CH2)3CH3


730
CHF2
Cl
H
CH(CH3)CH2CH(CH3)2


731
CHF2
Cl
H
CH(CH3)C(CH3)3


732
CHF2
Cl
H
CH(CH3)CH(CH3)2


733
CHF2
Cl
H
CH(CH3)CH2CH2CH(CH3)2


734
CHF2
Cl
H
CH(CH2CH3)2


735
CHF2
Cl
H
C(CH3)2CH2CH3


736
CHF2
Cl
H
C(CH3)2CH2C(CH3)3


737
CHF2
Cl
H
CH2—CH(OMe)2


738
CHF2
Cl
H
CH2—CH(OEt)2


739
CHF2
Cl
H
CH2CH2—OH


740
CHF2
Cl
H
CH2CH2—OMe


741
CHF2
Cl
Me
CH2CH2—OMe


742
CHF2
Cl
H
CH2CH2—OEt


743
CHF2
Cl
H
CH2CH2—SMe


744
CHF2
Cl
H
CH2CH2—CN


745
CHF2
Cl
H
CH2CH2—NMe2


746
CHF2
Cl
H
CH2CH2-morpholin-4-yl


747
CHF2
Cl
H
CH(CH3)CH2—OMe


748
CHF2
Cl
H
CH(CH3)CH2—NMe2


749
CHF2
Cl
H
CH2CH2CH2—OMe


750
CHF2
Cl
H
CH2CH2CH2—SMe


751
CHF2
Cl
H
CH2CH2CH2—OEt


752
CHF2
Cl
H
CH2CH2CH2—OiPr


753
CHF2
Cl
H
CH2CH2CH2—OBu


754
CHF2
Cl
H
CH2—COOCH3


755
CHF2
Cl
Me
CH2—COOCH3


756
CHF2
Cl
H
CH(CH3)COOMe


757
CHF2
Cl
H
CH(CH3)COOEt


758
CHF2
Cl
H
CH2CH2—COOCH3


759
CHF2
Cl
H
CH(COOCH3)2


760
CHF2
Cl
H
CH(COOEt)CH2—CH(CH3)2


761
CHF2
Cl
H
CH(COOMe)CH(CH3)2


762
CHF2
Cl
H
O—CH2CH3


763
CHF2
Cl
H
O—CH3


764
CHF2
Cl
H
O—CH2CH═CH2


765
CHF2
Cl
H
O—tBu


766
CHF2
Cl
H
O—Pr


767
CHF2
Cl
H
O—CH2cPr


768
CHF2
Cl
H
O—CH2CH(CH3)2


769
CHF2
Cl
H
O—CH2CF3


770
CHF2
Cl
H
O—CH(CH3)cPr


771
CHF2
Cl
H
O—CH2CH2Cl


772
CHF2
Cl
H
O—CH2C≡CH


773
CHF2
Cl
H
O—CH2C≡CCH3


774
CHF2
Cl
H
O—CH(CH3)C≡CH


775
CHF2
Cl
H
CH2—Ph


776
CHF2
Cl
Me
CH2—Ph


777
CHF2
Cl
H
CH2-pyridin-3-yl


778
CHF2
Cl
H
CH2-6-Cl-pyridin-3-yl


779
CHF2
Cl
H
CH(CH3)Ph


780
CHF2
Cl
H
CH2CH2—Ph


781
CHF2
Cl
H
CH2-2-CF3—Ph


782
CHF2
Cl
H
CH2CH2CHPh










783
CHF2
Cl
morpholin-4-yl


784
CHF2
Cl
piperidin-1-yl


785
CHF2
Cl
thiazolidin-3-yl


786
CHF2
Cl
pyrrolidin-1-yl


787
CHF2
Cl
2-methylpyrrolidin-1-yl


788
CHF2
Cl
═CH—N(CH3)2


789
CHF2
Cl
═C(CH3)N(CH3)2


790
CHF2
Cl
═CH—N(C2H5)2


791
CHF2
Cl
═C(CH3)N(C2H5)2


792
CHF2
Cl
═CH-piperidine


793
CHF2
Cl
═CH-morpholine


794
CHF2
Cl
═CH-pyrrolidine











795
CHF2
Cl
H
indan-1-yl


796
CHF2
Cl
H
tetrahydrofuran-2-ylmethyl


797
CF2CF3
Cl
H
H


798
CF2CF3
Cl
H
Me


799
CF2CF3
Cl
H
Et


800
CF2CF3
Cl
H
Pr


801
CF2CF3
Cl
H
iPr


802
CF2CF3
Cl
H
cPr


803
CF2CF3
Cl
H
Bu


804
CF2CF3
Cl
H
cBu


805
CF2CF3
Cl
H
tBu


806
CF2CF3
Cl
Me
Me


807
CF2CF3
Cl
Me
Et


808
CF2CF3
Cl
Me
Bu


809
CF2CF3
Cl
Me
Pr


810
CF2CF3
Cl
Me
iPr


811
CF2CF3
Cl
Et
Et


812
CF2CF3
Cl
Et
Pr


813
CF2CF3
Cl
Et
iPr


814
CF2CF3
Cl
Pr
Pr


815
CF2CF3
Cl
H
cPentyl


816
CF2CF3
Cl
H
cHexyl


817
CF2CF3
Cl
H
CH2(CH2)3CH3


818
CF2CF3
Cl
H
CH2(CH2)4CH3


819
CF2CF3
Cl
H
CH2—cPr


820
CF2CF3
Cl
H
CH2—CN


821
CF2CF3
Cl
H
CH2—C(CH3)3


822
CF2CF3
Cl
H
CH2CF2CF3


823
CF2CF3
Cl
H
CH2CF3


824
CF2CF3
Cl
H
CH2(CF2)2CF3


825
CF2CF3
Cl
H
CH2CH(CH3)CH2CH3


826
CF2CF3
Cl
H
CH2C(CH3)2CH2F


827
CF2CF3
Cl
H
CH2CH(CH3)2


828
CF2CF3
Cl
H
CH2CH(CH2CH3)2


829
CF2CF3
Cl
H
CH2CH2CH(CH3)2


830
CF2CF3
Cl
H
CH2CH2C(CH3)3


831
CF2CF3
Cl
H
CH2CH═CH2


832
CF2CF3
Cl
Me
CH2CH═CH2


833
CF2CF3
Cl
CH2CH═CH2
CH2CH═CH2


834
CF2CF3
Cl
H
CH2CH═CHCH3


835
CF2CF3
Cl
H
CH2—C(CH3)═CH2


836
CF2CF3
Cl
H
CH2—C≡CH


837
CF2CF3
Cl
Me
CH2—C≡CH


838
CF2CF3
Cl
H
CH(CH3)CH2CH3


839
CF2CF3
Cl
H
CH(CH3)cPr


840
CF2CF3
Cl
H
CH(CH3)(CH2)2CH3


841
CF2CF3
Cl
H
CH(CH3)(CH2)4CH3


842
CF2CF3
Cl
H
CH(CH3)(CH2)5CH3


843
CF2CF3
Cl
H
CH(CH2CH3)(CH2)3CH3


844
CF2CF3
Cl
H
CH(CH3)CH2CH(CH3)2


845
CF2CF3
Cl
H
CH(CH3)C(CH3)3


846
CF2CF3
Cl
H
CH(CH3)CH(CH3)2


847
CF2CF3
Cl
H
CH(CH3)CH2CH2CH(CH3)2


848
CF2CF3
Cl
H
CH(CH2CH3)2


849
CF2CF3
Cl
H
C(CH3)2CH2CH3


850
CF2CF3
Cl
H
C(CH3)2CH2C(CH3)3


851
CF2CF3
Cl
H
CH2—CH(OMe)2


852
CF2CF3
Cl
H
CH2—CH(OEt)2


853
CF2CF3
Cl
H
CH2CH2—OH


854
CF2CF3
Cl
H
CH2CH2—OMe


855
CF2CF3
Cl
Me
CH2CH2—OMe


856
CF2CF3
Cl
H
CH2CH2—OEt


857
CF2CF3
Cl
H
CH2CH2—SMe


858
CF2CF3
Cl
H
CH2CH2—CN


859
CF2CF3
Cl
H
CH2CH2—NMe2


860
CF2CF3
Cl
H
CH2CH2-morpholin-4-yl


861
CF2CF3
Cl
H
CH(CH3)CH2—OMe


862
CF2CF3
Cl
H
CH(CH3)CH2—NMe2


863
CF2CF3
Cl
H
CH2CH2CH2—OMe


864
CF2CF3
Cl
H
CH2CH2CH2—SMe


865
CF2CF3
Cl
H
CH2CH2CH2—OEt


866
CF2CF3
Cl
H
CH2CH2CH2—OiPr


867
CF2CF3
Cl
H
CH2CH2CH2—OBu


868
CF2CF3
Cl
H
CH2—COOCH3


869
CF2CF3
Cl
Me
CH2—COOCH3


870
CF2CF3
Cl
H
CH2CH2—COOCH3


871
CF2CF3
Cl
H
CH(COOCH3)2


872
CF2CF3
Cl
H
CH(COOEt)CH2—CH(CH3)2


873
CF2CF3
Cl
H
CH(COOMe)CH(CH3)2


874
CF2CF3
Cl
H
O—CH2CH3


875
CF2CF3
Cl
H
O—CH3


876
CF2CF3
Cl
H
O—CH2CH═CH2


877
CF2CF3
Cl
H
O—tBu


878
CF2CF3
Cl
H
O—Pr


879
CF2CF3
Cl
H
O—CH2cPr


880
CF2CF3
Cl
H
O—CH2CH(CH3)2


881
CF2CF3
Cl
H
O—CH2CF3


882
CF2CF3
Cl
H
O—CH(CH3)cPr


883
CF2CF3
Cl
H
O—CH2CH2Cl


884
CF2CF3
Cl
H
O—CH2C≡CH


885
CF2CF3
Cl
H
O—CH2C≡CCH3


886
CF2CF3
Cl
H
O—CH(CH3)C≡CH


887
CF2CF3
Cl
H
CH2—Ph


888
CF2CF3
Cl
Me
CH2—Ph


889
CF2CF3
Cl
H
CH2-pyridin-3-yl


890
CF2CF3
Cl
H
CH2-6-Cl-pyridin-3-yl


891
CF2CF3
Cl
H
CH(CH3)Ph


892
CF2CF3
Cl
H
CH2CH2—Ph


893
CF2CF3
Cl
H
CH2-2-CF3—Ph


894
CF2CF3
Cl
H
CH2CH2CHPh










895
CF2CF3
Cl
morpholin-4-yl


896
CF2CF3
Cl
piperidin-1-yl


897
CF2CF3
Cl
thiazolidin-3-yl


898
CF2CF3
Cl
pyrrolidin-1-yl


899
CF2CF3
Cl
2-methylpyrrolidin-1-yl


900
CF2CF3
Cl
═CH—N(CH3)2


901
CF2CF3
Cl
═C(CH3)N(CH3)2


902
CF2CF3
Cl
═CH—N(C2H5)2


903
CF2CF3
Cl
═C(CH3)N(C2H5)2


904
CF2CF3
Cl
═CH-piperidine


905
CF2CF3
Cl
═CH-morpholine


906
CF2CF3
Cl
═CH-pyrrolidine











907
CF2CF3
Cl
H
indan-1-yl


908
CF2CF3
Cl
H
tetrahydrofuran-2-ylmethyl


909
CF3
Br
H
H


910
CF3
Br
H
Me


911
CF3
Br
H
Et


912
CF3
Br
H
Pr


913
CF3
Br
H
iPr


914
CF3
Br
H
cPr


915
CF3
Br
H
Bu


916
CF3
Br
H
cBu


917
CF3
Br
H
tBu


918
CF3
Br
Me
Me


919
CF3
Br
Me
Et


920
CF3
Br
Me
Bu


921
CF3
Br
Me
Pr


922
CF3
Br
Me
iPr


923
CF3
Br
Et
Et


924
CF3
Br
Et
Pr


925
CF3
Br
Et
iPr


926
CF3
Br
Pr
Pr


927
CF3
Br
H
cPentyl


928
CF3
Br
H
cHexyl


929
CF3
Br
H
CH2(CH2)3CH3


930
CF3
Br
H
CH2(CH2)4CH3


931
CF3
Br
H
CH2—cPr


932
CF3
Br
H
CH2—CN


933
CF3
Br
H
CH2—C(CH3)3


934
CF3
Br
H
CH2CF2CF3


935
CF3
Br
H
CH2CF3


936
CF3
Br
H
CH2(CF2)2CF3


937
CF3
Br
H
CH2CH(CH3)CH2CH3


938
CF3
Br
H
CH2C(CH3)2CH2F


939
CF3
Br
H
CH2CH(CH3)2


940
CF3
Br
H
CH2CH(CH2CH3)2


941
CF3
Br
H
CH2CH2CH(CH3)2


942
CF3
Br
H
CH2CH2C(CH3)3


943
CF3
Br
H
CH2CH═CH2


944
CF3
Br
Me
CH2CH═CH2


945
CF3
Br
CH2CH═CH2
CH2CH═CH2


946
CF3
Br
H
CH2CH═CHCH3


947
CF3
Br
H
CH2—C(CH3)═CH2


948
CF3
Br
H
CH2—C≡CH


949
CF3
Br
Me
CH2—C≡CH


950
CF3
Br
H
CH(CH3)CH2CH3


951
CF3
Br
H
CH(CH3)cPr


952
CF3
Br
H
CH(CH3)(CH2)2CH3


953
CF3
Br
H
CH(CH3)(CH2)4CH3


954
CF3
Br
H
CH(CH3)(CH2)5CH3


955
CF3
Br
H
CH(CH2CH3)(CH2)3CH3


956
CF3
Br
H
CH(CH3)CH2CH(CH3)2


957
CF3
Br
H
CH(CH3)C(CH3)3


958
CF3
Br
H
CH(CH3)CH(CH3)2


959
CF3
Br
H
CH(CH3)CH2CH2CH(CH3)2


960
CF3
Br
H
CH(CH2CH3)2


961
CF3
Br
H
C(CH3)2CH2CH3


962
CF3
Br
H
C(CH3)2CH2C(CH3)3


963
CF3
Br
H
CH2—CH(OMe)2


964
CF3
Br
H
CH2—CH(OEt)2


965
CF3
Br
H
CH2CH2—OH


966
CF3
Br
H
CH2CH2—OMe


967
CF3
Br
Me
CH2CH2—OMe


968
CF3
Br
H
CH2CH2—OEt


969
CF3
Br
H
CH2CH2—SMe


970
CF3
Br
H
CH2CH2—CN


971
CF3
Br
H
CH2CH2—NMe2


972
CF3
Br
H
CH2CH2-morpholin-4-yl


973
CF3
Br
H
CH(CH3)CH2—OMe


974
CF3
Br
H
CH(CH3)CH2—NMe2


975
CF3
Br
H
CH2CH2CH2—OMe


976
CF3
Br
H
CH2CH2CH2—SMe


977
CF3
Br
H
CH2CH2CH2—OEt


978
CF3
Br
H
CH2CH2CH2—OiPr


979
CF3
Br
H
CH2CH2CH2—OBu


980
CF3
Br
H
CH2—COOCH3


981
CF3
Br
Me
CH2—COOCH3


982
CF3
Br
H
CH(CH3)COOMe


983
CF3
Br
H
CH(CH3)COOEt


984
CF3
Br
H
CH2CH2—COOCH3


985
CF3
Br
H
CH(COOCH3)2


986
CF3
Br
H
CH(COOEt)CH2—CH(CH3)2


987
CF3
Br
H
CH(COOMe)CH(CH3)2


988
CF3
Br
H
O—CH2CH3


989
CF3
Br
Me
O—CH3


990
CF3
Br
H
O—CH2CH═CH2


991
CF3
Br
H
O—tBu


992
CF3
Br
H
O—Pr


993
CF3
Br
H
O—CH2cPr


994
CF3
Br
H
O—CH2CH(CH3)2


995
CF3
Br
H
O—CH2CF3


996
CF3
Br
H
O—CH(CH3)cPr


997
CF3
Br
H
O—CH2CH2Cl


998
CF3
Br
H
O—CH2C≡CH


999
CF3
Br
H
O—CH2C≡CCH3


1000
CF3
Br
H
O—CH(CH3)C≡CH


1001
CF3
Br
H
CH2—Ph


1002
CF3
Br
Me
CH2—Ph


1003
CF3
Br
H
CH2-pyridin-3-yl


1004
CF3
Br
H
CH2-6-Cl-pyridin-3-yl


1005
CF3
Br
H
CH(CH3)Ph


1006
CF3
Br
H
CH2CH2—Ph


1007
CF3
Br
H
CH2-2-CF3—Ph


1008
CF3
Br
H
CH2CH2CHPh2










1009
CF3
Br
morpholin-4-yl


1010
CF3
Br
piperidin-1-yl


1011
CF3
Br
thiazolidin-3-yl


1012
CF3
Br
pyrrolidin-1-yl


1013
CF3
Br
2-methylpyrrolidin-1-yl


1014
CF3
Br
═CH—N(CH3)2


1015
CF3
Br
═C(CH3)N(CH3)2


1016
CF3
Br
═CH—N(C2H5)2


1017
CF3
Br
═C(CH3)N(C2H5)2


1018
CF3
Br
═CH-piperidine


1019
CF3
Br
═CH-morpholine


1020
CF3
Br
═CH-pyrrolidine











1021
CF3
Br
H
indan-1-yl


1022
CF3
Br
H
tetrahydrofuran-2-ylmethyl


1023
CF2Cl
Br
H
H


1024
CF2Cl
Br
H
Me


1025
CF2Cl
Br
H
Et


1026
CF2Cl
Br
H
Pr


1027
CF2Cl
Br
H
iPr


1028
CF2Cl
Br
H
cPr


1029
CF2Cl
Br
H
Bu


1030
CF2Cl
Br
H
cBu


1031
CF2Cl
Br
H
tBu


1032
CF2Cl
Br
Me
Me


1033
CF2Cl
Br
Me
Et


1034
CF2Cl
Br
Me
Bu


1035
CF2Cl
Br
Me
Pr


1036
CF2Cl
Br
Me
iPr


1037
CF2Cl
Br
Et
Et


1038
CF2Cl
Br
Et
Pr


1039
CF2Cl
Br
Et
iPr


1040
CF2Cl
Br
Pr
Pr


1041
CF2Cl
Br
H
cPentyl


1042
CF2Cl
Br
H
cHexyl


1043
CF2Cl
Br
H
CH2(CH2)3CH3


1044
CF2Cl
Br
H
CH2(CH2)4CH3


1045
CF2Cl
Br
H
CH2—cPr


1046
CF2Cl
Br
H
CH2—CN


1047
CF2Cl
Br
H
CH2—C(CH3)3


1048
CF2Cl
Br
H
CH2CF2CF3


1049
CF2Cl
Br
H
CH2CF3


1050
CF2Cl
Br
H
CH2(CF2)2CF3


1051
CF2Cl
Br
H
CH2CH(CH3)CH2CH3


1052
CF2Cl
Br
H
CH2C(CH3)2CH2F


1053
CF2Cl
Br
H
CH2CH(CH3)2


1054
CF2Cl
Br
H
CH2CH(CH2CH3)2


1055
CF2Cl
Br
H
CH2CH2CH(CH3)2


1056
CF2Cl
Br
H
CH2CH2C(CH3)3


1057
CF2Cl
Br
H
CH2CH═CH2


1058
CF2Cl
Br
Me
CH2CH═CH2


1059
CF2Cl
Br
CH2CH═CH2
CH2CH═CH2


1060
CF2Cl
Br
H
CH2CH═CHCH3


1061
CF2Cl
Br
H
CH2—C(CH3)═CH2


1062
CF2Cl
Br
H
CH2—C≡CH


1063
CF2Cl
Br
Me
CH2—C≡CH


1064
CF2Cl
Br
H
CH(CH3)CH2CH3


1065
CF2Cl
Br
H
CH(CH3)cPr


1066
CF2Cl
Br
H
CH(CH3)(CH2)2CH3


1067
CF2Cl
Br
H
CH(CH3)(CH2)4CH3


1068
CF2Cl
Br
H
CH(CH3)(CH2)5CH3


1069
CF2Cl
Br
H
CH(CH2CH3)(CH2)3CH3


1070
CF2Cl
Br
H
CH(CH3)CH2CH(CH3)2


1071
CF2Cl
Br
H
CH(CH3)C(CH3)3


1072
CF2Cl
Br
H
CH(CH3)CH(CH3)2


1073
CF2Cl
Br
H
CH(CH3)CH2CH2CH(CH3)2


1074
CF2Cl
Br
H
CH(CH2CH3)2


1075
CF2Cl
Br
H
C(CH3)2CH2CH3


1076
CF2Cl
Br
H
C(CH3)2CH2C(CH3)3


1077
CF2Cl
Br
H
CH2—CH(OMe)2


1078
CF2Cl
Br
H
CH2—CH(OEt)2


1079
CF2Cl
Br
H
CH2CH2—OH


1080
CF2Cl
Br
H
CH2CH2—OMe


1081
CF2Cl
Br
Me
CH2CH2—OMe


1082
CF2Cl
Br
H
CH2CH2—OEt


1083
CF2Cl
Br
H
CH2CH2—SMe


1084
CF2Cl
Br
H
CH2CH2—CN


1085
CF2Cl
Br
H
CH2CH2—NMe2


1086
CF2Cl
Br
H
CH2CH2-morpholin-4-yl


1087
CF2Cl
Br
H
CH(CH3)CH2—OMe


1088
CF2Cl
Br
H
CH(CH3)CH2—NMe2


1089
CF2Cl
Br
H
CH2CH2CH2—OMe


1090
CF2Cl
Br
H
CH2CH2CH2—SMe


1091
CF2Cl
Br
H
CH2CH2CH2—OEt


1092
CF2Cl
Br
H
CH2CH2CH2—OiPr


1093
CF2Cl
Br
H
CH2CH2CH2—OBu


1094
CF2Cl
Br
H
CH2—COOCH3


1095
CF2Cl
Br
Me
CH2—COOCH3


1096
CF2Cl
Br
H
CH(CH3)COOMe


1097
CF2Cl
Br
H
CH(CH3)COOEt


1098
CF2Cl
Br
H
CH2CH2—COOCH3


1099
CF2Cl
Br
H
CH(COOCH3)2


1100
CF2Cl
Br
H
CH(COOEt)CH2—CH(CH3)2


1101
CF2Cl
Br
H
CH(COOMe)CH(CH3)2


1102
CF2Cl
Br
H
O—CH2CH3


1103
CF2Cl
Br
Me
O—CH3


1104
CF2Cl
Br
H
O—CH2CH═CH2


1105
CF2Cl
Br
H
O—tBu


1106
CF2Cl
Br
H
O—Pr


1107
CF2Cl
Br
H
O—CH2cPr


1108
CF2Cl
Br
H
O—CH2CH(CH3)2


1109
CF2Cl
Br
H
O—CH2CF3


1110
CF2Cl
Br
H
O—CH(CH3)cPr


1111
CF2Cl
Br
H
O—CH2CH2Cl


1112
CF2Cl
Br
H
O—CH2C≡CH


1113
CF2Cl
Br
H
O—CH2C≡CCH3


1114
CF2Cl
Br
H
O—CH(CH3)C≡CH


1115
CF2Cl
Br
H
CH2—Ph


1116
CF2Cl
Br
Me
CH2—Ph


1117
CF2Cl
Br
H
CH2-pyridin-3-yl


1118
CF2Cl
Br
H
CH2-6-Cl-pyridin-3-yl


1119
CF2Cl
Br
H
CH(CH3)Ph


1120
CF2Cl
Br
H
CH2CH2—Ph


1121
CF2Cl
Br
H
CH2-2-CF3—Ph


1122
CF2Cl
Br
H
CH2CH2CHPh2










1123
CF2Cl
Br
morpholin-4-yl


1124
CF2Cl
Br
piperidin-1-yl


1125
CF2Cl
Br
thiazolidin-3-yl


1126
CF2Cl
Br
pyrrolidin-1-yl


1127
CF2Cl
Br
2-methylpyrrolidin-1-yl


1128
CF2Cl
Br
═CH—N(CH3)2


1129
CF2Cl
Br
═C(CH3)N(CH3)2


1130
CF2Cl
Br
═CH—N(C2H5)2


1131
CF2Cl
Br
═C(CH3)N(C2H5)2


1132
CF2Cl
Br
═CH-piperidine


1133
CF2Cl
Br
═CH-morpholine


1134
CF2Cl
Br
═CH-pyrrolidine











1135
CF2Cl
Br
H
indan-1-yl


1136
CF2Cl
Br
H
tetrahydrofuran-2-ylmethyl


1137
CHF2
Br
H
H


1138
CHF2
Br
H
Me


1139
CHF2
Br
H
Et


1140
CHF2
Br
H
Pr


1141
CHF2
Br
H
iPr


1142
CHF2
Br
H
cPr


1143
CHF2
Br
H
Bu


1144
CHF2
Br
H
cBu


1145
CHF2
Br
H
tBu


1146
CHF2
Br
Me
Me


1147
CHF2
Br
Me
Et


1148
CHF2
Br
Me
Bu


1149
CHF2
Br
Me
Pr


1150
CHF2
Br
Me
iPr


1151
CHF2
Br
Et
Et


1152
CHF2
Br
Et
Pr


1153
CHF2
Br
Et
iPr


1154
CHF2
Br
Pr
Pr


1155
CHF2
Br
H
cPentyl


1156
CHF2
Br
H
cHexyl


1157
CHF2
Br
H
CH2(CH2)3CH3


1158
CHF2
Br
H
CH2(CH2)4CH3


1159
CHF2
Br
H
CH2—cPr


1160
CHF2
Br
H
CH2—CN


1161
CHF2
Br
H
CH2—C(CH3)3


1162
CHF2
Br
H
CH2CF2CF3


1163
CHF2
Br
H
CH2CF3


1164
CHF2
Br
H
CH2(CF2)2CF3


1165
CHF2
Br
H
CH2CH(CH3)CH2CH3


1166
CHF2
Br
H
CH2C(CH3)2CH2F


1167
CHF2
Br
H
CH2CH(CH3)2


1168
CHF2
Br
H
CH2CH(CH2CH3)2


1169
CHF2
Br
H
CH2CH2CH(CH3)2


1170
CHF2
Br
H
CH2CH2C(CH3)3


1171
CHF2
Br
H
CH2CH═CH2


1172
CHF2
Br
Me
CH2CH═CH2


1173
CHF2
Br
CH2CH═CH2
CH2CH═CH2


1174
CHF2
Br
H
CH2CH═CHCH3


1175
CHF2
Br
H
CH2—C(CH3)═CH2


1176
CHF2
Br
H
CH2—C≡CH


1177
CHF2
Br
Me
CH2—C≡CH


1178
CHF2
Br
H
CH(CH3)CH2CH3


1179
CHF2
Br
H
CH(CH3)cPr


1180
CHF2
Br
H
CH(CH3)(CH2)2CH3


1181
CHF2
Br
H
CH(CH3)(CH2)4CH3


1182
CHF2
Br
H
CH(CH3)(CH2)5CH3


1183
CHF2
Br
H
CH(CH2CH3)(CH2)3CH3


1184
CHF2
Br
H
CH(CH3)CH2CH(CH3)2


1185
CHF2
Br
H
CH(CH3)C(CH3)3


1186
CHF2
Br
H
CH(CH3)CH(CH3)2


1187
CHF2
Br
H
CH(CH3)CH2CH2CH(CH3)2


1188
CHF2
Br
H
CH(CH2CH3)2


1189
CHF2
Br
H
C(CH3)2CH2CH3


1190
CHF2
Br
H
C(CH3)2CH2C(CH3)3


1191
CHF2
Br
H
CH2—CH(OMe)2


1192
CHF2
Br
H
CH2—CH(OEt)2


1193
CHF2
Br
H
CH2CH2—OH


1194
CHF2
Br
H
CH2CH2—OMe


1195
CHF2
Br
Me
CH2CH2—OMe


1196
CHF2
Br
H
CH2CH2—OEt


1197
CHF2
Br
H
CH2CH2—SMe


1198
CHF2
Br
H
CH2CH2—CN


1199
CHF2
Br
H
CH2CH2—NMe2


1200
CHF2
Br
H
CH2CH2-morpholin-4-yl


1201
CHF2
Br
H
CH(CH3)CH2—OMe


1202
CHF2
Br
H
CH(CH3)CH2—NMe2


1203
CHF2
Br
H
CH2CH2CH2—OMe


1204
CHF2
Br
H
CH2CH2CH2—SMe


1205
CHF2
Br
H
CH2CH2CH2—OEt


1206
CHF2
Br
H
CH2CH2CH2—OiPr


1207
CHF2
Br
H
CH2CH2CH2—OBu


1208
CHF2
Br
H
CH2—COOCH3


1209
CHF2
Br
Me
CH2—COOCH3


1210
CHF2
Br
H
CH(CH3)COOMe


1211
CHF2
Br
H
CH(CH3)COOEt


1212
CHF2
Br
H
CH2CH2—COOCH3


1213
CHF2
Br
H
CH(COOCH3)2


1214
CHF2
Br
H
CH(COOEt)CH2—CH(CH3)2


1215
CHF2
Br
H
CH(COOMe)CH(CH3)2


1216
CHF2
Br
H
O—CH2CH3


1217
CHF2
Br
Me
O—CH3


1218
CHF2
Br
H
O—CH2CH═CH2


1219
CHF2
Br
H
O—tBu


1220
CHF2
Br
H
O—Pr


1221
CHF2
Br
H
O—CH2cPr


1222
CHF2
Br
H
O—CH2CH(CH3)2


1223
CHF2
Br
H
O—CH2CF3


1224
CHF2
Br
H
O—CH(CH3)cPr


1225
CHF2
Br
H
O—CH2CH2Cl


1226
CHF2
Br
H
O—CH2C≡CH


1227
CHF2
Br
H
O—CH2C≡CCH3


1228
CHF2
Br
H
O—CH(CH3)C≡CH


1229
CHF2
Br
H
CH2—Ph


1230
CHF2
Br
Me
CH2—Ph


1231
CHF2
Br
H
CH2-pyridin-3-yl


1232
CHF2
Br
H
CH2-6-Cl-pyridin-3-yl


1233
CHF2
Br
H
CH(CH3)Ph


1234
CHF2
Br
H
CH2CH2—Ph


1235
CHF2
Br
H
CH2-2-CF3—Ph


1236
CHF2
Br
H
CH2CH2CHPh2










1237
CHF2
Br
morpholin-4-yl


1238
CHF2
Br
piperidin-1-yl


1239
CHF2
Br
thiazolidin-3-yl


1240
CHF2
Br
pyrrolidin-1-yl


1241
CHF2
Br
2-methylpyrrolidin-1-yl


1242
CHF2
Br
═CH—N(CH3)2


1243
CHF2
Br
═C(CH3)N(CH3)2


1244
CHF2
Br
═CH—N(C2H5)2


1245
CHF2
Br
═C(CH3)N(C2H5)2


1246
CHF2
Br
═CH-piperidine


1247
CHF2
Br
═CH-morpholine


1248
CHF2
Br
═CH-pyrrolidine











1249
CHF2
Br
H
indan-1-yl


1250
CHF2
Br
H
tetrahydrofuran-2-yl


1251
CF2CF3
Br
H
H


1252
CF2CF3
Br
H
Me


1253
CF2CF3
Br
H
Ey


1254
CF2CF3
Br
H
Pr


1255
CF2CF3
Br
H
iPr


1256
CF2CF3
Br
H
cPr


1257
CF2CF3
Br
H
Bu


1258
CF2CF3
Br
H
cBu


1259
CF2CF3
Br
H
tBu


1260
CF2CF3
Br
Me
Me


1261
CF2CF3
Br
Me
Et


1262
CF2CF3
Br
Me
Bu


1263
CF2CF3
Br
Me
Pr


1264
CF2CF3
Br
Me
iPr


1265
CF2CF3
Br
Et
Et


1266
CF2CF3
Br
Et
Pr


1267
CF2CF3
Br
Et
iPr


1268
CF2CF3
Br
Pr
Pr


1269
CF2CF3
Br
H
cPentyl


1270
CF2CF3
Br
H
cHexyl


1271
CF2CF3
Br
H
CH2(CH2)3CH3


1272
CF2CF3
Br
H
CH2(CH2)4CH3


1273
CF2CF3
Br
H
CH2—cPr


1274
CF2CF3
Br
H
CH2—CN


1275
CF2CF3
Br
H
CH2—C(CH3)3


1276
CF2CF3
Br
H
CH2CF2CF3


1277
CF2CF3
Br
H
CH2CF3


1278
CF2CF3
Br
H
CH2(CF2)2CF3


1279
CF2CF3
Br
H
CH2CH(CH3)CH2CH3


1280
CF2CF3
Br
H
CH2C(CH3)2CH2F


1281
CF2CF3
Br
H
CH2CH(CH3)2


1282
CF2CF3
Br
H
CH2CH(CH2CH3)2


1283
CF2CF3
Br
H
CH2CH2CH(CH3)2


1284
CF2CF3
Br
H
CH2CH2C(CH3)3


1285
CF2CF3
Br
H
CH2CH═CH2


1286
CF2CF3
Br
Me
CH2CH═CH2


1287
CF2CF3
Br
CH2CH═CH2
CH2CH═CH2


1288
CF2CF3
Br
H
CH2CH═CHCH3


1289
CF2CF3
Br
H
CH2—C(CH3)═CH2


1290
CF2CF3
Br
H
CH2—C≡CH


1291
CF2CF3
Br
Me
CH2—C≡CH


1292
CF2CF3
Br
H
CH(CH3)CH2CH3


1293
CF2CF3
Br
H
CH(CH3)cPr


1294
CF2CF3
Br
H
CH(CH3)(CH2)2CH3


1295
CF2CF3
Br
H
CH(CH3)(CH2)4CH3


1296
CF2CF3
Br
H
CH(CH3)(CH2)5CH3


1297
CF2CF3
Br
H
CH(CH2CH3)(CH2)3CH3


1298
CF2CF3
Br
H
CH(CH3)CH2CH(CH3)2


1299
CF2CF3
Br
H
CH(CH3)C(CH3)3


1300
CF2CF3
Br
H
CH(CH3)CH(CH3)2


1301
CF2CF3
Br
H
CH(CH3)CH2CH2CH(CH3)2


1302
CF2CF3
Br
H
CH(CH2CH3)2


1303
CF2CF3
Br
H
C(CH3)2CH2CH3


1304
CF2CF3
Br
H
C(CH3)2CH2C(CH3)3


1305
CF2CF3
Br
H
CH2—CH(OMe)2


1306
CF2CF3
Br
H
CH2—CH(OEt)2


1307
CF2CF3
Br
H
CH2CH2—OH


1308
CF2CF3
Br
H
CH2CH2—OMe


1309
CF2CF3
Br
Me
CH2CH2—OMe


1310
CF2CF3
Br
H
CH2CH2—OEt


1311
CF2CF3
Br
H
CH2CH2—SMe


1312
CF2CF3
Br
H
CH2CH2—CN


1313
CF2CF3
Br
H
CH2CH2—NMe2


1314
CF2CF3
Br
H
CH2CH2-morpholin-4-yl


1315
CF2CF3
Br
H
CH(CH3)CH2—OMe


1316
CF2CF3
Br
H
CH(CH3)CH2—NMe2


1317
CF2CF3
Br
H
CH2CH2CH2—OMe


1318
CF2CF3
Br
H
CH2CH2CH2—SMe


1319
CF2CF3
Br
H
CH2CH2CH2—OEt


1320
CF2CF3
Br
H
CH2CH2CH2—OiPr


1321
CF2CF3
Br
H
CH2CH2CH2—OBu


1322
CF2CF3
Br
H
CH2—COOCH3


1323
CF2CF3
Br
Me
CH2—COOCH3


1324
CF2CF3
Br
H
CH(CH3)COOMe


1325
CF2CF3
Br
H
CH(CH3)COOEt


1326
CF2CF3
Br
H
CH2CH2—COOCH3


1327
CF2CF3
Br
H
CH(COOCH3)2


1328
CF2CF3
Br
H
CH(COOEt)CH2—CH(CH3)2


1329
CF2CF3
Br
H
CH(COOMe)CH(CH3)2


1330
CF2CF3
Br
H
O—CH2CH3


1331
CF2CF3
Br
Me
O—CH3


1332
CF2CF3
Br
H
O—CH2CH═CH2


1333
CF2CF3
Br
H
O—tBu


1334
CF2CF3
Br
H
O—Pr


1335
CF2CF3
Br
H
O—CH2cPr


1336
CF2CF3
Br
H
O—CH2CH(CH3)2


1337
CF2CF3
Br
H
O—CH2CF3


1338
CF2CF3
Br
H
O—CH(CH3)cPr


1339
CF2CF3
Br
H
O—CH2CH2Cl


1340
CF2CF3
Br
H
O—CH2C≡CH


1341
CF2CF3
Br
H
O—CH2C≡CCH3


1342
CF2CF3
Br
H
O—CH(CH3)C≡CH


1343
CF2CF3
Br
H
CH2—Ph


1344
CF2CF3
Br
Me
CH2—Ph


1345
CF2CF3
Br
H
CH2-pyridin-3-yl


1346
CF2CF3
Br
H
CH2-6-Cl-pyridin-3-yl


1347
CF2CF3
Br
H
CH(CH3)Ph


1348
CF2CF3
Br
H
CH2CH2—Ph


1349
CF2CF3
Br
H
CH2-2-CF3—Ph


1350
CF2CF3
Br
H
CH2CH2CHPh2










1351
CF2CF3
Br
morpholin-4-yl


1352
CF2CF3
Br
piperidin-1-yl


1353
CF2CF3
Br
thiazolidin-3-yl


1354
CF2CF3
Br
pyrrolidin-1-yl


1355
CF2CF3
Br
2-methylpyrrolidin-1-yl


1356
CF2CF3
Br
═CH—N(CH3)2


1357
CF2CF3
Br
═C(CH3)N(CH3)2


1358
CF2CF3
Br
═CH—N(C2H5)2


1359
CF2CF3
Br
═C(CH3)N(C2H5)2


1360
CF2CF3
Br
═CH-piperidine


1361
CF2CF3
Br
═CH-morpholine


1362
CF2CF3
Br
═CH-pyrrolidine











1363
CF2CF3
Br
H
indan-1-yl


1364
CF2CF3
Br
H
tetrahydrofuran-2-ylmethyl


1365
CF2CF3
I
H
H


1366
CF3
I
H
H


1367
CF2CHF2
H
H
H


1368
CF2CHF2
H
H
Me


1369
CF2CHF2
H
H
Et


1370
CF2CHF2
H
H
Pr


1371
CF2CHF2
H
H
iPr


1372
CF2CHF2
H
H
cPr


1373
CF2CHF2
H
H
Bu


1374
CF2CHF2
H
H
cBu


1375
CF2CHF2
H
H
tBu


1376
CF2CHF2
H
Me
Me


1377
CF2CHF2
H
Me
Et


1378
CF2CHF2
H
Me
Bu


1379
CF2CHF2
H
Me
Pr


1380
CF2CHF2
H
Me
iPr


1381
CF2CHF2
H
Et
Et


1382
CF2CHF2
H
Et
Pr


1383
CF2CHF2
H
Et
iPr


1384
CF2CHF2
H
Pr
Pr


1385
CF2CHF2
H
H
cPentyl


1386
CF2CHF2
H
H
cHexyl


1387
CF2CHF2
H
H
CH2(CH2)3CH3


1388
CF2CHF2
H
H
CH2(CH2)4CH3


1389
CF2CHF2
H
H
CH2—cPr


1390
CF2CHF2
H
H
CH2—CN


1391
CF2CHF2
H
H
CH2—C(CH3)3


1392
CF2CHF2
H
H
CH2CF2CF3


1393
CF2CHF2
H
H
CH2CF3


1394
CF2CHF2
H
H
CH2(CF2)2CF3


1395
CF2CHF2
H
H
CH2CH(CH3)CH2CH3


1396
CF2CHF2
H
H
CH2C(CH3)2CH2F


1397
CF2CHF2
H
H
CH2CH(CH3)2


1398
CF2CHF2
H
H
CH2CH(CH2CH3)2


1399
CF2CHF2
H
H
CH2CH2CH(CH3)2


1400
CF2CHF2
H
H
CH2CH2C(CH3)3


1401
CF2CHF2
H
H
CH2CH═CH2


1402
CF2CHF2
H
Me
CH2CH═CH2


1403
CF2CHF2
H
CH2CH═CH2
CH2CH═CH2


1404
CF2CHF2
H
H
CH2CH═CHCH3


1405
CF2CHF2
H
H
CH2—C(CH3)═CH2


1406
CF2CHF2
H
H
CH2—C≡CH


1407
CF2CHF2
H
Me
CH2—C≡CH


1408
CF2CHF2
H
H
CH(CH3)CH2CH3


1409
CF2CHF2
H
H
CH(CH3)cPr


1410
CF2CHF2
H
H
CH(CH3)(CH2)2CH3


1411
CF2CHF2
H
H
CH(CH3)(CH2)4CH3


1412
CF2CHF2
H
H
CH(CH3)(CH2)5CH3


1413
CF2CHF2
H
H
CH(CH2CH3)(CH2)3CH3


1414
CF2CHF2
H
H
CH(CH3)CH2CH(CH3)2


1415
CF2CHF2
H
H
CH(CH3)C(CH3)3


1416
CF2CHF2
H
H
CH(CH3)CH(CH3)2


1417
CF2CHF2
H
H
CH(CH3)CH2CH2CH(CH3)2


1418
CF2CHF2
H
H
CH(CH2CH3)2


1419
CF2CHF2
H
H
C(CH3)2CH2CH3


1420
CF2CHF2
H
H
C(CH3)2CH2C(CH3)3


1421
CF2CHF2
H
H
CH2—CH(OMe)2


1422
CF2CHF2
H
H
CH2—CH(OEt)2


1423
CF2CHF2
H
H
CH2CH2—OH


1424
CF2CHF2
H
H
CH2CH2—OMe


1425
CF2CHF2
H
Me
CH2CH2—OMe


1426
CF2CHF2
H
H
CH2CH2—OEt


1427
CF2CHF2
H
H
CH2CH2—SMe


1428
CF2CHF2
H
H
CH2CH2—CN


1429
CF2CHF2
H
H
CH2CH2—NMe2


1430
CF2CHF2
H
H
CH2CH2-morpholin-4-yl


1431
CF2CHF2
H
H
CH(CH3)CH2—OMe


1432
CF2CHF2
H
H
CH(CH3)CH2—NMe2


1433
CF2CHF2
H
H
CH2CH2CH2—OMe


1434
CF2CHF2
H
H
CH2CH2CH2—SMe


1435
CF2CHF2
H
H
CH2CH2CH2—OEt


1436
CF2CHF2
H
H
CH2CH2CH2—OiPr


1437
CF2CHF2
H
H
CH2CH2CH2—OBu


1438
CF2CHF2
H
H
CH2—COOCH3


1439
CF2CHF2
H
Me
CH2—COOCH3


1440
CF2CHF2
H
H
CH(CH3)COOMe


1441
CF2CHF2
H
H
CH(CH3)COOEt


1442
CF2CHF2
H
H
CH2CH2—COOCH3


1443
CF2CHF2
H
H
CH(COOCH3)2


1444
CF2CHF2
H
H
CH(COOEt)CH2—CH(CH3)2


1445
CF2CHF2
H
H
CH(COOMe)CH(CH3)2


1446
CF2CHF2
H
H
O—CH2CH3


1447
CF2CHF2
H
H
O—CH3


1448
CF2CHF2
H
H
O—CH2CH═CH2


1449
CF2CHF2
H
H
O—tBu


1450
CF2CHF2
H
H
O—Pr


1451
CF2CHF2
H
H
O—CH2cPr


1452
CF2CHF2
H
H
O—CH2CH(CH3)2


1453
CF2CHF2
H
H
O—CH2CF3


1454
CF2CHF2
H
H
O—CH(CH3)cPr


1455
CF2CHF2
H
H
O—CH2CH2Cl


1456
CF2CHF2
H
H
O—CH2C≡CH


1457
CF2CHF2
H
H
O—CH2C≡CCH3


1458
CF2CHF2
H
H
O—CH(CH3)C≡CH


1459
CF2CHF2
H
H
CH2—Ph


1460
CF2CHF2
H
Me
CH2—Ph


1461
CF2CHF2
H
H
CH2-pyridin-3-yl


1462
CF2CHF2
H
H
CH2-6-Cl-pyridin-3-yl


1463
CF2CHF2
H
H
CH(CH3)Ph


1464
CF2CHF2
H
H
CH2CH2—Ph


1465
CF2CHF2
H
H
CH2-2-CF3—Ph


1466
CF2CHF2
H
H
CH2CH2CHPh










1467
CF2CHF2
H
morpholin-4-yl


1468
CF2CHF2
H
piperidin-1-yl


1469
CF2CHF2
H
thiazolidin-3-yl


1470
CF2CHF2
H
pyrrolidin-1-yl


1471
CF2CHF2
H
2-methylpyrrolidin-1-yl


1472
CF2CHF2
H
═CH—N(CH3)2


1473
CF2CHF2
H
═C(CH3)N(CH3)2


1474
CF2CHF2
H
═CH—N(C2H5)2


1475
CF2CHF2
H
═C(CH3)N(C2H5)2


1476
CF2CHF2
H
═CH-piperidine


1477
CF2CHF2
H
═CH-morpholine


1478
CF2CHF2
H
═CH-pyrrolidine











1479
CF2CHF2
H
H
indan-1-yl


1480
CF2CHF2
H
H
tetrahydrofuran-2-ylmethyl


1481
CF2CF2Cl
H
H
H


1482
CF2CF2Cl
H
H
Me


1483
CF2CF2Cl
H
H
Et


1484
CF2CF2Cl
H
H
Pr


1485
CF2CF2Cl
H
H
iPr


1486
CF2CF2Cl
H
H
cPr


1487
CF2CF2Cl
H
H
Bu


1488
CF2CF2Cl
H
H
cBu


1489
CF2CF2Cl
H
H
tBu


1490
CF2CF2Cl
H
Me
Me


1491
CF2CF2Cl
H
Me
Et


1492
CF2CF2Cl
H
Me
Bu


1493
CF2CF2Cl
H
Me
Pr


1494
CF2CF2Cl
H
Me
iPr


1495
CF2CF2Cl
H
Et
Et


1496
CF2CF2Cl
H
Et
Pr


1497
CF2CF2Cl
H
Et
iPr


1498
CF2CF2Cl
H
Pr
Pr


1499
CF2CF2Cl
H
H
cPentyl


1500
CF2CF2Cl
H
H
cHexyl


1501
CF2CF2Cl
H
H
CH2(CH2)3CH3


1502
CF2CF2Cl
H
H
CH2(CH2)4CH3


1503
CF2CF2Cl
H
H
CH2—cPr


1504
CF2CF2Cl
H
H
CH2—CN


1505
CF2CF2Cl
H
H
CH2—C(CH3)3


1506
CF2CF2Cl
H
H
CH2CF2CF3


1507
CF2CF2Cl
H
H
CH2CF3


1508
CF2CF2Cl
H
H
CH2(CF2)2CF3


1509
CF2CF2Cl
H
H
CH2CH(CH3)CH2CH3


1510
CF2CF2Cl
H
H
CH2C(CH3)2CH2F


1511
CF2CF2Cl
H
H
CH2CH(CH3)2


1512
CF2CF2Cl
H
H
CH2CH(CH2CH3)2


1513
CF2CF2Cl
H
H
CH2CH2CH(CH3)2


1514
CF2CF2Cl
H
H
CH2CH2C(CH3)3


1515
CF2CF2Cl
H
H
CH2CH═CH2


1516
CF2CF2Cl
H
Me
CH2CH═CH2


1517
CF2CF2Cl
H
CH2CH═CH2
CH2CH═CH2


1518
CF2CF2Cl
H
H
CH2CH═CHCH3


1519
CF2CF2Cl
H
H
CH2—C(CH3)═CH2


1520
CF2CF2Cl
H
H
CH2—C≡CH


1521
CF2CF2Cl
H
Me
CH2—C≡CH


1522
CF2CF2Cl
H
H
CH(CH3)CH2CH3


1523
CF2CF2Cl
H
H
CH(CH3)cPr


1524
CF2CF2Cl
H
H
CH(CH3)(CH2)2CH3


1525
CF2CF2Cl
H
H
CH(CH3)(CH2)4CH3


1526
CF2CF2Cl
H
H
CH(CH3)(CH2)5CH3


1527
CF2CF2Cl
H
H
CH(CH2CH3)(CH2)3CH3


1528
CF2CF2Cl
H
H
CH(CH3)CH2CH(CH3)2


1529
CF2CF2Cl
H
H
CH(CH3)C(CH3)3


1530
CF2CF2Cl
H
H
CH(CH3)CH(CH3)2


1531
CF2CF2Cl
H
H
CH(CH3)CH2CH2CH(CH3)2


1532
CF2CF2Cl
H
H
CH(CH2CH3)2


1533
CF2CF2Cl
H
H
C(CH3)2CH2CH3


1534
CF2CF2Cl
H
H
C(CH3)2CH2C(CH3)3


1535
CF2CF2Cl
H
H
CH2—CH(OMe)2


1536
CF2CF2Cl
H
H
CH2—CH(OEt)2


1537
CF2CF2Cl
H
H
CH2CH2—OH


1538
CF2CF2Cl
H
H
CH2CH2—OMe


1539
CF2CF2Cl
H
Me
CH2CH2—OMe


1540
CF2CF2Cl
H
H
CH2CH2—OEt


1541
CF2CF2Cl
H
H
CH2CH2—SMe


1542
CF2CF2Cl
H
H
CH2CH2—CN


1543
CF2CF2Cl
H
H
CH2CH2—NMe2


1544
CF2CF2Cl
H
H
CH2CH2-morpholin-4-yl


1545
CF2CF2Cl
H
H
CH(CH3)CH2—OMe


1546
CF2CF2Cl
H
H
CH(CH3)CH2—NMe2


1547
CF2CF2Cl
H
H
CH2CH2CH2—OMe


1548
CF2CF2Cl
H
H
CH2CH2CH2—SMe


1549
CF2CF2Cl
H
H
CH2CH2CH2—OEt


1550
CF2CF2Cl
H
H
CH2CH2CH2—OiPr


1551
CF2CF2Cl
H
H
CH2CH2CH2—OBu


1552
CF2CF2Cl
H
H
CH2—COOCH3


1553
CF2CF2Cl
H
Me
CH2—COOCH3


1554
CF2CF2Cl
H
H
CH(CH3)COOMe


1555
CF2CF2Cl
H
H
CH(CH3)COOEt


1556
CF2CF2Cl
H
H
CH2CH2—COOCH3


1557
CF2CF2Cl
H
H
CH(COOCH3)2


1558
CF2CF2Cl
H
H
CH(COOEt)CH2—CH(CH3)2


1559
CF2CF2Cl
H
H
CH(COOMe)CH(CH3)2


1560
CF2CF2Cl
H
H
O—CH2CH3


1561
CF2CF2Cl
H
H
O—CH3


1562
CF2CF2Cl
H
H
O—CH2CH═CH2


1563
CF2CF2Cl
H
H
O—tBu


1564
CF2CF2Cl
H
H
O—Pr


1565
CF2CF2Cl
H
H
O—CH2cPr


1566
CF2CF2Cl
H
H
O—CH2CH(CH3)2


1567
CF2CF2Cl
H
H
O—CH2CF3


1568
CF2CF2Cl
H
H
O—CH(CH3)cPr


1569
CF2CF2Cl
H
H
O—CH2CH2Cl


1570
CF2CF2Cl
H
H
O—CH2C≡CH


1571
CF2CF2Cl
H
H
O—CH2C≡CCH3


1572
CF2CF2Cl
H
H
O—CH(CH3)C≡CH


1573
CF2CF2Cl
H
H
CH2—Ph


1574
CF2CF2Cl
H
Me
CH2—Ph


1575
CF2CF2Cl
H
H
CH2-pyridin-3-yl


1576
CF2CF2Cl
H
H
CH2-6-Cl-pyridin-3-yl


1577
CF2CF2Cl
H
H
CH(CH3)Ph


1578
CF2CF2Cl
H
H
CH2CH2—Ph


1579
CF2CF2Cl
H
H
CH2-2-CF3—Ph


1580
CF2CF2Cl
H
H
CH2CH2CHPh










1581
CF2CF2Cl
H
morpholin-4-yl


1582
CF2CF2Cl
H
piperidin-1-yl


1583
CF2CF2Cl
H
thiazolidin-3-yl


1584
CF2CF2Cl
H
pyrrolidin-1-yl


1585
CF2CF2Cl
H
2-methylpyrrolidin-1-yl


1586
CF2CF2Cl
H
═CH—N(CH3)2


1587
CF2CF2Cl
H
═C(CH3)N(CH3)2


1588
CF2CF2Cl
H
═CH—N(C2H5)2


1589
CF2CF2Cl
H
═C(CH3)N(C2H5)2


1590
CF2CF2Cl
H
═CH-piperidine


1591
CF2CF2Cl
H
═CH-morpholine


1592
CF2CF2Cl
H
═CH-pyrrolidine











1593
CF2CF2Cl
H
H
indan-1-yl


1594
CF2CF2Cl
H
H
tetrahydrofuran-2-ylmethyl


1595
C3F7
H
H
H


1596
C3F7
H
H
Me


1597
C3F7
H
H
Et


1598
C3F7
H
H
Pr


1599
C3F7
H
H
iPr


1600
C3F7
H
H
cPr


1601
C3F7
H
H
Bu


1602
C3F7
H
H
cBu


1603
C3F7
H
H
tBu


1604
C3F7
H
Me
Me


1605
C3F7
H
Me
Et


1606
C3F7
H
Me
Bu


1607
C3F7
H
Me
Pr


1608
C3F7
H
Me
iPr


1609
C3F7
H
Et
Et


1610
C3F7
H
Et
Pr


1611
C3F7
H
Et
iPr


1612
C3F7
H
Pr
Pr


1613
C3F7
H
H
cPentyl


1614
C3F7
H
H
cHexyl


1615
C3F7
H
H
CH2(CH2)3CH3


1616
C3F7
H
H
CH2(CH2)4CH3


1617
C3F7
H
H
CH2—cPr


1618
C3F7
H
H
CH2—CN


1619
C3F7
H
H
CH2—C(CH3)3


1620
C3F7
H
H
CH2CF2CF3


1621
C3F7
H
H
CH2CF3


1622
C3F7
H
H
CH2(CF2)2CF3


1623
C3F7
H
H
CH2CH(CH3)CH2CH3


1624
C3F7
H
H
CH2C(CH3)2CH2F


1625
C3F7
H
H
CH2CH(CH3)2


1626
C3F7
H
H
CH2CH(CH2CH3)2


1627
C3F7
H
H
CH2CH2CH(CH3)2


1628
C3F7
H
H
CH2CH2C(CH3)3


1629
C3F7
H
H
CH2CH═CH2


1630
C3F7
H
Me
CH2CH═CH2


1631
C3F7
H
CH2CH═CH2
CH2CH═CH2


1632
C3F7
H
H
CH2CH═CHCH3


1633
C3F7
H
H
CH2—C(CH3)═CH2


1634
C3F7
H
H
CH2—C≡CH


1635
C3F7
H
Me
CH2—C≡CH


1636
C3F7
H
H
CH(CH3)CH2CH3


1637
C3F7
H
H
CH(CH3)cPr


1638
C3F7
H
H
CH(CH3)(CH2)2CH3


1639
C3F7
H
H
CH(CH3)(CH2)4CH3


1640
C3F7
H
H
CH(CH3)(CH2)5CH3


1641
C3F7
H
H
CH(CH2CH3)(CH2)3CH3


1642
C3F7
H
H
CH(CH3)CH2CH(CH3)2


1643
C3F7
H
H
CH(CH3)C(CH3)3


1644
C3F7
H
H
CH(CH3)CH(CH3)2


1645
C3F7
H
H
CH(CH3)CH2CH2CH(CH3)2


1646
C3F7
H
H
CH(CH2CH3)2


1647
C3F7
H
H
C(CH3)2CH2CH3


1648
C3F7
H
H
C(CH3)2CH2C(CH3)3


1649
C3F7
H
H
CH2—CH(OMe)2


1650
C3F7
H
H
CH2—CH(OEt)2


1651
C3F7
H
H
CH2CH2—OH


1652
C3F7
H
H
CH2CH2—OMe


1653
C3F7
H
Me
CH2CH2—OMe


1654
C3F7
H
H
CH2CH2—OEt


1655
C3F7
H
H
CH2CH2—SMe


1656
C3F7
H
H
CH2CH2—CN


1657
C3F7
H
H
CH2CH2—NMe2


1658
C3F7
H
H
CH2CH2-morpholin-4-yl


1659
C3F7
H
H
CH(CH3)CH2—OMe


1660
C3F7
H
H
CH(CH3)CH2—NMe2


1661
C3F7
H
H
CH2CH2CH2—OMe


1662
C3F7
H
H
CH2CH2CH2—SMe


1663
C3F7
H
H
CH2CH2CH2—OEt


1664
C3F7
H
H
CH2CH2CH2—OiPr


1665
C3F7
H
H
CH2CH2CH2—OBu


1666
C3F7
H
H
CH2—COOCH3


1667
C3F7
H
Me
CH2—COOCH3


1668
C3F7
H
H
CH(CH3)COOMe


1669
C3F7
H
H
CH(CH3)COOEt


1670
C3F7
H
H
CH2CH2—COOCH3


1671
C3F7
H
H
CH(COOCH3)2


1672
C3F7
H
H
CH(COOEt)CH2—CH(CH3)2


1673
C3F7
H
H
CH(COOMe)CH(CH3)2


1674
C3F7
H
H
O—CH2CH3


1675
C3F7
H
H
O—CH3


1676
C3F7
H
H
O—CH2CH═CH2


1677
C3F7
H
H
O—tBu


1678
C3F7
H
H
O—Pr


1679
C3F7
H
H
O—CH2cPr


1680
C3F7
H
H
O—CH2CH(CH3)2


1681
C3F7
H
H
O—CH2CF3


1682
C3F7
H
H
O—CH(CH3)cPr


1683
C3F7
H
H
O—CH2CH2Cl


1684
C3F7
H
H
O—CH2C≡CH


1685
C3F7
H
H
O—CH2C≡CCH3


1686
C3F7
H
H
O—CH(CH3)C≡CH


1687
C3F7
H
H
CH2—Ph


1688
C3F7
H
Me
CH2—Ph


1689
C3F7
H
H
CH2-pyridin-3-yl


1690
C3F7
H
H
CH2-6-Cl-pyridin-3-yl


1691
C3F7
H
H
CH(CH3)Ph


1692
C3F7
H
H
CH2CH2—Ph


1693
C3F7
H
H
CH2-2-CF3—Ph


1694
C3F7
H
H
CH2CH2CHPh










1695
C3F7
H
morpholin-4-yl


1696
C3F7
H
piperidin-1-yl


1697
C3F7
H
thiazolidin-3-yl


1698
C3F7
H
pyrrolidin-1-yl


1699
C3F7
H
2-methylpyrrolidin-1-yl


1700
C3F7
H
═CH—N(CH3)2


1701
C3F7
H
═C(CH3)N(CH3)2


1702
C3F7
H
═CH—N(C2H5)2


1703
C3F7
H
═C(CH3)N(C2H5)2


1704
C3F7
H
═CH-piperidine


1705
C3F7
H
═CH-morpholine


1706
C3F7
H
═CH-pyrrolidine











1707
C3F7
H
H
indan-1-yl


1708
C3F7
H
H
tetrahydrofuran-2-ylmethyl


1709
CF(CF3)2
H
H
H


1710
C3F7
Cl
H
H


1711
C3F7
Cl
H
Me


1712
C3F7
Cl
H
Et


1713
C3F7
Cl
H
Pr


1714
C3F7
Cl
H
iPr


1715
C3F7
Cl
H
cPr


1716
C3F7
Cl
H
Bu


1717
C3F7
Cl
H
cBu


1718
C3F7
Cl
H
tBu


1719
C3F7
Cl
Me
Me


1720
C3F7
Cl
Et
Et


1721
C3F7
Cl
H
CH2—cPr


1722
C3F7
Cl
H
CH2—C(CH3)3


1723
C3F7
Cl
H
CH2CH(CH3)2


1724
C3F7
Cl
H
CH2CH(CH2CH3)2


1725
C3F7
Cl
H
CH2CH2CH(CH3)2


1726
C3F7
Cl
H
CH2CH2C(CH3)3


1727
C3F7
Cl
H
CH2CH═CH2


1728
C3F7
Cl
H
CH2—C(CH3)═CH2


1729
C3F7
Cl
H
CH2—CCH


1730
C3F7
Cl
Me
CH2—CCH


1731
C3F7
Cl
H
CH(CH3)CH2CH3


1732
C3F7
Cl
H
CH(CH3)cPr


1733
C3F7
Cl
H
CH(CH3)(CH2)2CH3


1734
C3F7
Cl
H
CH(CH3)(CH2)4CH3


1735
C3F7
Cl
H
CH(CH3)CH2CH(CH3)2


1736
C3F7
Cl
H
CH(CH3)C(CH3)3


1737
C3F7
Cl
H
CH(CH3)CH(CH3)2


1738
C3F7
Cl
H
CH(CH2CH3)2


1739
C3F7
Cl
H
CH2—CH(OMe)2


1740
C3F7
Cl
H
CH2—CH(OEt)2


1741
C3F7
Cl
H
CH2CH2—OH


1742
C3F7
Cl
H
CH2CH2—OMe


1743
C3F7
Cl
Me
CH2CH2—OMe


1744
C3F7
Cl
H
CH(CH3)CH2—OMe


1745
C3F7
Cl
H
CH2CH2CH2—OMe


1746
C3F7
Cl
H
CH2—COOCH3


1747
C3F7
Cl
Me
CH2—COOCH3


1748
C3F7
Cl
H
CH(CH3)COOMe


1749
C3F7
Cl
H
CH(CH3)COOEt


1750
C3F7
Cl
H
CH2CH2—COOCH3


1751
C3F7
Br
H
H


1752
C3F7
Br
H
Me


1753
C3F7
Br
H
Et


1754
C3F7
Br
H
Pr


1755
C3F7
Br
H
iPr


1756
C3F7
Br
H
cPr


1757
C3F7
Br
H
Bu


1758
C3F7
Br
H
cBu


1759
C3F7
Br
H
tBu


1760
C3F7
Br
Me
Me


1761
C3F7
Br
Et
Et


1762
C3F7
Br
H
CH2-cPr


1763
C3F7
Br
H
CH2—C(CH3)3


1764
C3F7
Br
H
CH2CH(CH3)2


1765
C3F7
Br
H
CH2CH(CH2CH3)2


1766
C3F7
Br
H
CH2CH2CH(CH3)2


1767
C3F7
Br
H
CH2CH2C(CH3)3


1768
C3F7
Br
H
CH2CH═CH2


1769
C3F7
Br
H
CH2—C(CH3)═CH2


1770
C3F7
Br
H
CH2—CCH


1771
C3F7
Br
Me
CH2—CCH


1772
C3F7
Br
H
CH(CH3)CH2CH3


1773
C3F7
Br
H
CH(CH3)cPr


1774
C3F7
Br
H
CH(CH3)(CH2)2CH3


1775
C3F7
Br
H
CH(CH3)(CH2)4CH3


1776
C3F7
Br
H
CH(CH3)CH2CH(CH3)2


1777
C3F7
Br
H
CH(CH3)C(CH3)3


1778
C3F7
Br
H
CH(CH3)CH(CH3)2


1779
C3F7
Br
H
CH(CH3)CH2CH2CH(CH3)2


1780
C3F7
Br
H
CH(CH2CH3)2


1781
C3F7
Br
H
CH2—CH(OMe)2


1782
C3F7
Br
H
CH2—CH(OEt)2


1783
C3F7
Br
H
CH2CH2—OH


1784
C3F7
Br
H
CH2CH2—OMe


1785
C3F7
Br
H
CH(CH3)CH2—OMe


1786
C3F7
Br
H
CH2CH2CH2—OMe


1787
C3F7
Br
H
CH2—COOCH3


1788
C3F7
Br
Me
CH2—COOCH3


1789
C3F7
Br
H
CH(CH3)COOMe


1790
C3F7
Br
H
CH(CH3)COOEt


1791
C3F7
Br
H
CH2CH2—COOCH3


1792
C3F7
I
H
H


1793
C3F7
I
H
Me


1794
C3F7
I
H
Et


1795
C3F7
I
H
Pr


1796
C3F7
I
H
iPr


1797
C3F7
I
H
cPr


1798
C3F7
I
H
Bu


1799
C3F7
I
H
cBu


1800
C3F7
I
H
tBu


1801
C3F7
I
Me
Me


1802
C3F7
I
Et
Et


1803
C3F7
I
H
CH2—cPr


1804
C3F7
I
H
CH2—C(CH3)3


1805
C3F7
I
H
CH2CH(CH3)2


1806
C3F7
I
H
CH2CH(CH2CH3)2


1807
C3F7
I
H
CH2CH2CH(CH3)2


1808
C3F7
I
H
CH2CH2C(CH3)3


1809
C3F7
I
H
CH2CH═CH2


1810
C3F7
I
H
CH2—C(CH3)═CH2


1811
C3F7
I
H
CH2—CCH


1812
C3F7
I
Me
CH2—CCH


1813
C3F7
I
H
CH(CH3)CH2CH3


1814
C3F7
I
H
CH(CH3)cPr


1815
C3F7
I
H
CH(CH3)(CH2)2CH3


1816
C3F7
I
H
CH(CH3)(CH2)4CH3


1817
C3F7
I
H
CH(CH3)CH2CH(CH3)2


1818
C3F7
I
H
CH(CH3)C(CH3)3


1819
C3F7
I
H
CH(CH3)CH(CH3)2


1820
C3F7
I
H
CH(CH2CH3)2


1821
C3F7
I
H
CH2—CH(OMe)2


1822
C3F7
I
H
CH2—CH(OEt)2


1823
C3F7
I
H
CH2CH2—OH


1824
C3F7
I
H
CH2CH2—OMe


1825
C3F7
I
Me
CH2CH2—OMe


1826
C3F7
I
H
CH(CH3)CH2—OMe


1827
C3F7
I
H
CH2CH2CH2—OMe


1828
C3F7
I
H
CH2—COOCH3


1829
C3F7
I
Me
CH2—COOCH3


1830
C3F7
I
H
CH(CH3)COOMe


1831
C3F7
I
H
CH(CH3)COOEt


1832
C3F7
I
H
CH2CH2—COOCH3


1833
CF3
I
H
Me


1834
CF3
I
H
Et


1835
CF3
I
H
Pr


1836
CF3
I
H
iPr


1837
CF3
I
H
cPr


1838
CF3
I
H
Bu


1839
CF3
I
H
cBu


1840
CF3
I
H
tBu


1841
CF3
I
Me
Me


1842
CF3
I
Et
Et


1843
CF3
I
H
CH2(CH2)3CH3


1844
CF3
I
H
CH2(CH2)4CH3


1845
CF3
I
H
CH2—cPr


1846
CF3
I
H
CH2—C(CH3)3


1847
CF3
I
H
CH2CH(CH3)2


1848
CF3
I
H
CH2CH(CH2CH3)2


1849
CF3
I
H
CH2CH2CH(CH3)2


1850
CF3
I
H
CH2CH2C(CH3)3


1851
CF3
I
H
CH2CH═CH2


1852
CF3
I
H
CH2—C(CH3)═CH2


1853
CF3
I
H
CH2—CCH


1854
CF3
I
H
CH(CH3)CH2CH3


1855
CF3
I
H
CH(CH3)cPr


1856
CF3
I
H
CH(CH3)(CH2)2CH3


1857
CF3
I
H
CH(CH3)(CH2)4CH3


1858
CF3
I
H
CH(CH3)CH2CH(CH3)2


1859
CF3
I
H
CH(CH3)C(CH3)3


1860
CF3
I
H
CH(CH3)CH(CH3)2


1861
CF3
I
H
CH(CH2CH3)2


1862
CF3
I
H
C(CH3)2CH2CH3


1863
CF3
I
H
C(CH3)2CH2C(CH3)3


1864
CF3
I
H
CH2—CH(OMe)2


1865
CF3
I
H
CH2—CH(OEt)2


1866
CF3
I
H
CH2CH2—OH


1867
CF3
I
H
CH2CH2—OMe


1868
CF3
I
Me
CH2CH2—OMe


1869
CF3
I
H
CH(CH3)CH2—OMe


1870
CF3
I
H
CH2CH2CH2—OMe


1871
CF3
I
H
CH2—COOCH3


1872
CF3
I
Me
CH2—COOCH3


1873
CF3
I
H
CH(CH3)COOMe


1874
CF3
I
H
CH(CH3)COOEt


1875
CF3
I
H
CH2CH2—COOCH3


1876
CF2Cl
I
H
H


1877
CF2Cl
I
H
Me


1878
CF2Cl
I
H
Et


1879
CF2Cl
I
H
Pr


1880
CF2Cl
I
H
iPr


1881
CF2Cl
I
H
cPr


1882
CF2Cl
I
H
Bu


1883
CF2Cl
I
H
cBu


1884
CF2Cl
I
H
tBu


1885
CF2Cl
I
Me
Me


1886
CF2Cl
I
H
CH2—cPr


1887
CF2Cl
I
H
CH2—C(CH3)3


1888
CF2Cl
I
H
CH2CH(CH3)2


1889
CF2Cl
I
H
CH2CH(CH2CH3)2


1890
CF2Cl
I
H
CH2CH2CH(CH3)2


1891
CF2Cl
I
H
CH2CH2C(CH3)3


1892
CF2Cl
I
H
CH2CH═CH2


1893
CF2Cl
I
Me
CH2CH═CH2


1894
CF2Cl
I
H
CH2—C(CH3)═CH2


1895
CF2Cl
I
H
CH2—CCH


1896
CF2Cl
I
Me
CH2—CCH


1897
CF2Cl
I
H
CH(CH3)CH2CH3


1898
CF2Cl
I
H
CH(CH3)cPr


1899
CF2Cl
I
H
CH(CH3)(CH2)2CH3


1900
CF2Cl
I
H
CH(CH3)(CH2)4CH3


1901
CF2Cl
I
H
CH(CH3)(CH2)5CH3


1902
CF2Cl
I
H
CH(CH2CH3)(CH2)3CH3


1903
CF2Cl
I
H
CH(CH3)CH2CH(CH3)2


1904
CF2Cl
I
H
CH(CH3)C(CH3)3


1905
CF2Cl
I
H
CH(CH3)CH(CH3)2


1906
CF2Cl
I
H
CH(CH3)CH2CH2CH(CH3)2


1907
CF2Cl
I
H
CH(CH2CH3)2


1908
CF2Cl
I
H
C(CH3)2CH2CH3


1909
CF2Cl
I
H
C(CH3)2CH2C(CH3)3


1910
CF2Cl
I
H
CH2—CH(OMe)2


1911
CF2Cl
I
H
CH2—CH(OEt)2


1912
CF2Cl
I
H
CH2CH2—OH


1913
CF2Cl
I
H
CH2CH2—OMe


1914
CF2Cl
I
Me
CH2CH2—OMe


1915
CF2Cl
I
H
CH2CH2—OEt


1916
CF2Cl
I
H
CH(CH3)CH2—OMe


1917
CF2Cl
I
H
CH2CH2CH2—OMe


1918
CF2Cl
I
H
CH2—COOCH3


1919
CF2Cl
I
Me
CH2—COOCH3


1920
CF2Cl
I
H
CH(CH3)COOMe


1921
CF2Cl
I
H
CH(CH3)COOEt


1922
CF2Cl
I
H
CH2CH2—COOCH3


1923
CF2CF3
I
H
Me


1924
CF2CF3
I
H
Et


1925
CF2CF3
I
H
Pr


1926
CF2CF3
I
H
iPr


1927
CF2CF3
I
H
cPr


1928
CF2CF3
I
H
Bu


1929
CF2CF3
I
H
cBu


1930
CF2CF3
I
H
tBu


1931
CF2CF3
I
Me
Me


1932
CF2CF3
I
Et
Et


1933
CF2CF3
I
H
CH2—cPr


1934
CF2CF3
I
H
CH2—C(CH3)3


1935
CF2CF3
I
H
CH2CH(CH3)2


1936
CF2CF3
I
H
CH2CH(CH2CH3)2


1937
CF2CF3
I
H
CH2CH2CH(CH3)2


1938
CF2CF3
I
H
CH2CH2C(CH3)3


1939
CF2CF3
I
H
CH2CH═CH2


1940
CF2CF3
I
Me
CH2CH═CH2


1941
CF2CF3
I
H
CH2—C(CH3)═CH2


1942
CF2CF3
I
H
CH2—CCH


1943
CF2CF3
I
Me
CH2—CCH


1944
CF2CF3
I
H
CH(CH3)CH2CH3


1945
CF2CF3
I
H
CH(CH3)cPr


1946
CF2CF3
I
H
CH(CH3)(CH2)2CH3


1947
CF2CF3
I
H
CH(CH3)(CH2)4CH3


1948
CF2CF3
I
H
CH(CH3)CH2CH(CH3)2


1949
CF2CF3
I
H
CH(CH3)C(CH3)3


1950
CF2CF3
I
H
CH(CH3)CH(CH3)2


1951
CF2CF3
I
H
CH(CH2CH3)2


1952
CF2CF3
I
H
CH2—CH(OMe)2


1953
CF2CF3
I
H
CH2—CH(OEt)2


1954
CF2CF3
I
HH
CH2CH2—OH


1955
CF2CF3
I
H
CH2CH2—OMe


1956
CF2CF3
I
Me
CH2CH2—OMe


1957
CF2CF3
I
H
CH(CH3)CH2—OMe


1958
CF2CF3
I
H
CH2CH2CH2—OMe


1959
CF2CF3
I
H
CH2—COOCH3


1960
CF2CF3
I
Me
CH2—COOCH3


1961
CF2CF3
I
H
CH(CH3)COOMe


1962
CF2CF3
I
H
CH(CH3)COOEt


1963
CF2CF3
I
H
CH2CH2—COOCH3


1964
CF2CF2Cl
Cl
H
H


1965
CF2CF2Cl
Cl
H
Me


1966
CF2CF2Cl
Cl
H
Et


1967
CF2CF2Cl
Cl
H
Pr


1968
CF2CF2Cl
Cl
H
iPr


1969
CF2CF2Cl
Cl
H
cPr


1970
CF2CF2Cl
Cl
H
Bu


1971
CF2CF2Cl
Cl
H
cBu


1972
CF2CF2Cl
Cl
H
tBu


1973
CF2CF2Cl
Cl
Me
Me


1974
CF2CF2Cl
Cl
Et
Et


1975
CF2CF2Cl
Cl
H
CH2—cPr


1976
CF2CF2Cl
Cl
H
CH2—C(CH3)3


1977
CF2CF2Cl
Cl
H
CH2CH(CH3)2


1978
CF2CF2Cl
Cl
H
CH2CH(CH2CH3)2


1979
CF2CF2Cl
Cl
H
CH2CH2CH(CH3)2


1980
CF2CF2Cl
Cl
H
CH2CH2C(CH3)3


1981
CF2CF2Cl
Cl
H
CH2CH═CH2


1982
CF2CF2Cl
Cl
Me
CH2CH═CH2


1983
CF2CF2Cl
Cl
H
CH2—C(CH3)═CH2


1984
CF2CF2Cl
Cl
H
CH2—CCH


1985
CF2CF2Cl
Cl
Me
CH2—CCH


1986
CF2CF2Cl
Cl
H
CH(CH3)CH2CH3


1987
CF2CF2Cl
Cl
H
CH(CH3)cPr


1988
CF2CF2Cl
Cl
H
CH(CH3)(CH2)2CH3


1989
CF2CF2Cl
Cl
H
CH(CH3)(CH2)4CH3


1990
CF2CF2Cl
Cl
H
CH(CH3)CH2CH(CH3)2


1991
CF2CF2Cl
Cl
H
CH(CH3)C(CH3)3


1992
CF2CF2Cl
Cl
H
CH(CH3)CH(CH3)2


1993
CF2CF2Cl
Cl
H
CH(CH2CH3)2


1994
CF2CF2Cl
Cl
H
CH2—CH(OMe)2


1995
CF2CF2Cl
Cl
H
CH2—CH(OEt)2


1996
CF2CF2Cl
Cl
H
CH2CH2—OH


1997
CF2CF2Cl
Cl
H
CH2CH2—OMe


1998
CF2CF2Cl
Cl
Me
CH2CH2—OMe


1999
CF2CF2Cl
Cl
H
CH(CH3)CH2—OMe


2000
CF2CF2Cl
Cl
H
CH2CH2CH2—OMe


2001
CF2CF2Cl
Cl
H
CH2—COOCH3


2002
CF2CF2Cl
Cl
Me
CH2—COOCH3


2003
CF2CF2Cl
Cl
H
CH(CH3)COOMe


2004
CF2CF2Cl
Cl
H
CH(CH3)COOEt


2005
CF2CF2Cl
Cl
H
CH2CH2—COOCH3


2006
CF2CF2Cl
Br
H
H


2007
CF2CF2Cl
Br
H
Me


2008
CF2CF2Cl
Br
H
Et


2009
CF2CF2Cl
Br
H
Pr


2010
CF2CF2Cl
Br
H
iPr


2011
CF2CF2Cl
Br
H
cPr


2012
CF2CF2Cl
Br
H
Bu


2013
CF2CF2Cl
Br
H
cBu


2014
CF2CF2Cl
Br
H
tBu


2015
CF2CF2Cl
Br
Me
Me


2016
CF2CF2Cl
Br
Et
Et


2017
CF2CF2Cl
Br
H
CH2—cPr


2018
CF2CF2Cl
Br
H
CH2—C(CH3)3


2019
CF2CF2Cl
Br
H
CH2CH(CH3)2


2020
CF2CF2Cl
Br
H
CH2CH(CH2CH3)2


2021
CF2CF2Cl
Br
H
CH2CH2CH(CH3)2


2022
CF2CF2Cl
Br
H
CH2CH2C(CH3)3


2023
CF2CF2Cl
Br
H
CH2CH═CH2


2024
CF2CF2Cl
Br
Me
CH2CH═CH2


2025
CF2CF2Cl
Br
H
CH2—C(CH3)═CH2


2026
CF2CF2Cl
Br
H
CH2—CCH


2027
CF2CF2Cl
Br
Me
CH2—CCH


2028
CF2CF2Cl
Br
H
CH(CH3)CH2CH3


2029
CF2CF2Cl
Br
H
CH(CH3)cPr


2030
CF2CF2Cl
Br
H
CH(CH3)(CH2)2CH3


2031
CF2CF2Cl
Br
H
CH(CH3)(CH2)4CH3


2032
CF2CF2Cl
Br
H
CH(CH3)CH2CH(CH3)2


2033
CF2CF2Cl
Br
H
CH(CH3)C(CH3)3


2034
CF2CF2Cl
Br
H
CH(CH3)CH(CH3)2


2035
CF2CF2Cl
Br
H
CH(CH2CH3)2


2036
CF2CF2Cl
Br
H
CH2—CH(OMe)2


2037
CF2CF2Cl
Br
H
CH2—CH(OEt)2


2038
CF2CF2Cl
Br
H
CH2CH2—OH


2039
CF2CF2Cl
Br
H
CH2CH2—OMe


2040
CF2CF2Cl
Br
Me
CH2CH2—OMe


2041
CF2CF2Cl
Br
H
CH(CH3)CH2—OMe


2042
CF2CF2Cl
Br
H
CH2CH2CH2—OMe


2043
CF2CF2Cl
Br
H
CH2—COOCH3


2044
CF2CF2Cl
Br
Me
CH2—COOCH3


2045
CF2CF2Cl
Br
H
CH(CH3)COOMe


2046
CF2CF2Cl
Br
H
CH(CH3)COOEt


2047
CF2CF2Cl
Br
H
CH2CH2—COOCH3


2048
CF2CF2Cl
I
H
H


2049
CF2CF2Cl
I
H
Me


2050
CF2CF2Cl
I
H
Et


2051
CF2CF2Cl
I
H
Pr


2052
CF2CF2Cl
I
H
iPr


2053
CF2CF2Cl
I
H
cPr


2054
CF2CF2Cl
I
H
Bu


2055
CF2CF2Cl
I
H
cBu


2056
CF2CF2Cl
I
H
tBu


2057
CF2CF2Cl
I
Me
Me


2058
CF2CF2Cl
I
Et
Et


2059
CF2CF2Cl
I
H
CH2—cPr


2060
CF2CF2Cl
I
H
CH2—C(CH3)3


2061
CF2CF2Cl
I
H
CH2CH(CH3)2


2062
CF2CF2Cl
I
H
CH2CH(CH2CH3)2


2063
CF2CF2Cl
I
H
CH2CH2CH(CH3)2


2064
CF2CF2Cl
I
H
CH2CH2C(CH3)3


2065
CF2CF2Cl
I
H
CH2CH═CH2


2066
CF2CF2Cl
I
Me
CH2CH═CH2


2067
CF2CF2Cl
I
H
CH2—C(CH3)═CH2


2068
CF2CF2Cl
I
H
CH2—CCH


2069
CF2CF2Cl
I
Me
CH2—CCH


2070
CF2CF2Cl
I
H
CH(CH3)CH2CH3


2071
CF2CF2Cl
I
H
CH(CH3)cPr


2072
CF2CF2Cl
I
H
CH(CH3)(CH2)2CH3


2073
CF2CF2Cl
I
H
CH(CH3)(CH2)4CH3


2074
CF2CF2Cl
I
H
CH(CH3)CH2CH(CH3)2


2075
CF2CF2Cl
I
H
CH(CH3)C(CH3)3


2077
CF2CF2Cl
I
H
CH(CH3)CH(CH3)2


2078
CF2CF2Cl
I
H
CH(CH2CH3)2


2079
CF2CF2Cl
I
H
CH2—CH(OMe)2


2080
CF2CF2Cl
I
H
CH2—CH(OEt)2


2081
CF2CF2Cl
I
H
CH2CH2—OH


2082
CF2CF2Cl
I
Me
CH2CH2—OMe


2083
CF2CF2Cl
I
H
CH2CH2—OMe


2084
CF2CF2Cl
I
H
CH(CH3)CH2—OMe


2085
CF2CF2Cl
I
H
CH2CH2CH2—OMe


2086
CF2CF2Cl
I
Me
CH2—COOCH3


2087
CF2CF2Cl
I
H
CH2—COOCH3


2088
CF2CF2Cl
I
H
CH(CH3)COOMe


2089
CF2CF2Cl
I
H
CH(CH3)COOEt


2090
CFClCF3
H
H
CH2CH2—COOCH3


2091
CFClCF3
H
H
H


2092
CFClCF3
H
H
Me


2093
CFClCF3
H
H
Et


2094
CFClCF3
H
H
Pr


2095
CFClCF3
H
H
iPr


2096
CFClCF3
H
H
cPr


2097
CFClCF3
H
H
Bu


2098
CFClCF3
H
H
tBu


2099
CFClCF3
H
Me
Me


2100
CFClCF3
H
Et
Et


2101
CFClCF3
H
H
CH2—cPr


2102
CFClCF3
H
H
CH2—C(CH3)3


2103
CFClCF3
H
H
CH2CH(CH3)2


2104
CFClCF3
H
H
CH2CH(CH2CH3)2


2105
CFClCF3
H
H
CH2CH2CH(CH3)2


2106
CFClCF3
H
H
CH2CH2C(CH3)3


2107
CFClCF3
H
H
CH2CH═CH2


2108
CFClCF3
H
Me
CH2CH═CH2


2109
CFClCF3
H
H
CH2—C(CH3)═CH2


2110
CFClCF3
H
H
CH2—CCH


2111
CFClCF3
H
Me
CH2—CCH


2112
CFClCF3
H
H
CH(CH3)CH2CH3


2113
CFClCF3
H
H
CH(CH3)cPr


2114
CFClCF3
H
H
CH(CH3)(CH2)2CH3


2115
CFClCF3
H
H
CH(CH3)(CH2)4CH3


2116
CFClCF3
H
H
CH(CH3)CH2CH(CH3)2


2117
CFClCF3
H
H
CH(CH3)C(CH3)3


2118
CFClCF3
H
H
CH(CH3)CH(CH3)2


2119
CFClCF3
H
H
CH(CH2CH3)2


2120
CFClCF3
H
H
CH—CH(OMe)2


2121
CFClCF3
H
H
CH—CH(OEt)2


2122
CFClCF3
H
H
CH2CH2—OH


2123
CFClCF3
H
H
CH2CH2—OMe


2124
CFClCF3
H
Me
CH2CH2—OMe


2125
CFClCF3
H
H
CH(CH3)CH2—OMe


2126
CFClCF3
H
H
CH2CH2CH2—OMe


2127
CFClCF3
H
H
CH2—COOCH3


2128
CFClCF3
H
Me
CH2—COOCH3


2129
CFClCF3
H
H
CH(CH3)COOMe


2130
CFClCF3
H
H
CH(CH3)COOEt


2131
CFClCF3
H
H
CH2CH2—COOCH3


2132
CFClCF3
Br
H
H


2133
CFClCF3
Br
H
Me


2134
CFClCF3
Br
H
Et


2135
CFClCF3
Br
H
Pr


2136
CFClCF3
Br
H
iPr


2137
CFClCF3
Br
H
cPr


2138
CFClCF3
Br
H
Bu


2139
CFClCF3
Br
H
cBu


2140
CFClCF3
Br
H
tBu


2141
CFClCF3
Br
Me
Me


2142
CFClCF3
Br
Et
Et


2143
CFClCF3
Br
H
CH2—cPr


2144
CFClCF3
Br
H
CH2—C(CH3)3


2145
CFClCF3
Br
H
CH2CH(CH3)2


2146
CFClCF3
Br
H
CH2CH(CH2CH3)2


2147
CFClCF3
Br
H
CH2CH2CH(CH3)2


2148
CFClCF3
Br
H
CH2CH2C(CH3)3


2149
CFClCF3
Br
H
CH2CH═CH2


2150
CFClCF3
Br
Me
CH2CH═CH2


2151
CFClCF3
Br
H
CH2—C(CH3)═CH2


2152
CFClCF3
Br
H
CH2—C≡CH


2153
CFClCF3
Br
Me
CH2—C≡CH


2154
CFClCF3
Br
H
CH(CH3)CH2CH3


2155
CFClCF3
Br
H
CH(CH3)cPr


2156
CFClCF3
Br
H
CH(CH3)(CH2)2CH3


2157
CFClCF3
Br
H
CH(CH3)(CH2)4CH3


2158
CFClCF3
Br
H
CH(CH3)CH2CH(CH3)2


2159
CFClCF3
Br
H
CH(CH3)C(CH3)3


2160
CFClCF3
Br
H
CH(CH3)CH(CH3)2


2161
CFClCF3
Br
H
CH(CH2CH3)2


2162
CFClCF3
Br
H
CH2—CH(OMe)2


2163
CFClCF3
Br
H
CH2—CH(OEt)2


2164
CFClCF3
Br
H
CH2CH2—OH


2165
CFClCF3
Br
H
CH2CH2—OMe


2166
CFClCF3
Br
Me
CH2CH2—OMe


2167
CFClCF3
Br
H
CH(CH3)CH2—OMe


2168
CFClCF3
Br
H
CH2CH2CH2—OMe


2169
CFClCF3
Br
H
CH2—COOCH3


2170
CFClCF3
Br
Me
CH2—COOCH3


2171
CFClCF3
Br
H
CH(CH3)COOMe


2172
CFClCF3
Br
H
CH(CH3)COOEt


2173
CFClCF3
Br
H
CH2CH2—COOCH3
















TABLE 2







NMR data of compounds from Table 1








Ex. No.
1H-NMR data











1
[CDCl3] 3.03 (d, 3H); 6.88 (d, 1H); 8.65 (d, 1H); 9.22 (br, 1H)


2
[CDCl3] 1.25 (t, 3H); 3.5 (m, 2H); 6.92 (d, 1H); 8.72 (d, 1H), 9.33 (br, 1H), 13.4 (br, 1H)


3
[CDCl3] 1.02 (t, 3H); 1.62 (m, 2H); 3.42 (m, 2H); 6.90 (d, 1H); 8.70 (d, 1H); 9.35 (br, 1H);



13.3 (br, 1H)


4
[CDCl3] 1.25 (d, 6H); 4.22 (m, 1H); 6.90 (d, 1H); 8.68 (d, 1H); 9.22 (d, br, 1H)


5
[CDCl3] 0.61 (m, 2H); 0.89 (m, 2H); 3.00 (m, 1H); 6.90 (d, 1H); 8.68 (d, 1H), 9.31 (br, 1H)


6
[CDCl3] 0.96 (t, 3H); 1.41 (m, 2H); 1.61 (m, 2H); 3.48 (q, 2H); 6.90 (d, 1H); 8.70 (d, 1H);



9.31 (br, 1H); 13.3 (br, 1H)


7
[CDCl3] 1.80 (m, 2H); 2.00 (m, 2H); 2.42 (m, 2H); 4.55 (m, 1H); 6.88 (d, 1H); 8.65 (d, 1H);



9.50 (br, 1H)


8
[CDCl3] 1.44 (s, 9H); 6.90 (d, 1H); 8.62 (d, 1H); 9.32 (br, 1H); 13.4 (br, 1H)


9
[CDCl3] 3.05 (s, 6H); 7.10 (d, 1H); 7.77 (d, 1H)


10
[CDCl3] 1.22 (t, 3H); 3.02 (s, 3H); 3.46 (m, 2H); 7.08 (d, 1H); 7.77 (d, 1H)


11
[CDCl3] 0.90 (t, 3H); 1.30 (br, 2H); 1.60 (m, 2H); 3.03 (s, 3H); 3.42 (br, 2H); 7.10 (d, 1H);



7.74 (d, 1H)


13
[CDCl3] 1.20 (d, 6H); 2.90 (s, 3H); 4.05 (m, br, 1H); 7.03 (d, 1H); 8.68 (d, 1H); 11.2 (br)


14
[CDCl3] 1.20 (t, 6H); 3.40 (m, 4H); 7.05 (d, 1H); 8.70 (d, 1H); 11.1 (br)


16
[CDCl3] 1.21 (m, 9H); 3.39 (q, 2H); 4.0 (br, 1H); 7.04 (d, 1H); 7.68 (d, 1H); 10.6 (br, 1H)


18
[CDCl3] 1.5-1.8 (m, 8H); 4.40 (m, 1H); 6.90 (d, 1H); 8.68 (d, 1H); 9.40 (d, br, 1H); 13.5 (br)


19
[CDCl3] 1.2-1.5 (m, 6H); 1.76 (m, 2H); 2.00 (m, 2H); 4.00 (m, 1H); 6.90 (d, 1H); 8.68 (d, 1H);



9.30 (d, br, 1H); 13.4 (br, 1H)


20
[CDCl3] 0.90 (t, 3H); 1.38 (m, 4H); 1.61 (m, 2H); 3.41 (m, 2H); 6.86 (d, 1H); 8.63 (d, 1H);



9.20 (t, 1H)


22
[CDCl3] 0.30 (m, 2H); 0.60 (m, 2H); 1.05 (m, 1H); 3.30 (m, 2H); 6.90 (d, 1H), 8.70 (d, 1H);



9.38 (br, 1H)


24
[CDCl3] 1.00 (s, 9H); 3.28 (d, 2H); 6.90 (d, 1H); 8,73 (d, 1H); 9.4 (br, 1H); 13.2 (br, 1H)


25
[CDCl3] 4.18 (dt, 2H); 6.92 (d, 1H); 8.72 (d, 1H); 9.8 (t, br, 1H)


26
[CDCl3] 4.11 (m, 2H); 6.90 (d, 1H); 8.70 (d, 1H); 9.80 (br, 1H); 12.16 (br, 1H)


27
[CDCl3] 4.22 (dt; 2H); 6.93 (d, 1H); 8.72 (d, 1H); 9.80 (t, br, 1H)


30
[CDCl3] 1.00 (d, 6H); 1.87 (m, 1H); 3.29 (t, 2H); 6.88 (d, 1H); 8.64 (d, 1H); 9.32 (br, 1H);



12.5 (br, 1H)


32
[CDCl3] 0.95 (d, 6H); 1.48 (m, 2H); 1.70 (m, 1H); 3.48 (m, 2H); 6.88 (d, 1H); 8.65 (d, 1H);



9.22 (br, 1H), 12.6 (br)


34
[CDCl3] 4.10 (t, 2H); 5.22 (dd, 2H); 5.95 (m, 1H); 6.90 (d, 1H); 8.70 (d, 1H); 9.40 (br, 1H);



12.7 (br, 1H)


36
[CDCl3] 4.0 (m, 4H); 5.21 (d, 4H); 5.80 (m, 2H); 7.04 (d, 1H); 7.78 (d, 1H); 11.0 (br)


38
[CDCl3] 1.80 (s, 3H); 4.02 (d, 2H); 4.93 (d, 2H); 6.89 (d 1H); 8.70 (d, 1H); 9.43 (br, 1H);



13.2 (br, 1H)


39
[CDCl3] 2.24 (t, 1H); 4.22 (m, 2H); 6.88 (d, 1H); 8.68 (d, 1H); 9.50 (br, 1H)


40
[CDCl3] 2.30 (s, 1H); 3.12 (s, 3H); 4.22 (br, 2H); 7.04 (d, 1H); 7.84 (d, 1H); 10.9 (br)


41
[CDCl3] 0.95 (t, 3H); 1.22 (d, 3H); 1.58 (m, 2H); 4.10 (m, 1H); 6.88 (d, 1H); 8.66 (d, 1H);



9.20 (br, 1H); 13.0 (br, 1H)


43
[DMSO] 0.93 (t, 3H); 1.16 (d, 3H); 1.30 (m, 2H); 1.48 (m, 2H); 4.00 (m, 1H); 7.35 (br, 1H);



7.39 (d, 1H); 8.40 (d, 1H); 13.40 (br)


44
[DMSO] 0.87 (t, 3H); 1.15 (d, 3H); 1.27 (m, 6H); 1.48 (m, 2H); 4.00 (m, 1H); 7.33 (d, 1H);



8.40 (d, 1H); 8.80 (br, 1H), 13.4 (br, 1H)


47
[CDCl3] 0.93 (d, 6H); 1.22 (d, 3H); 1.35 (m, 1H), 1.50 (m, 1H); 1.65 (m, 1H); 4.23 (m, 1H);



6.90 (d, 1H); 8.64 (d, 1H); 9.20 (d, br, 1H); 13.3 (br, 1H)


48
[CDCl3] 0.96 (s, 9H); 1.18 (d, 3H); 4.10 (m, 1H); 6.90 (d, 1H); 8.74 (d, 1H); 9.37 (d, br, 1H),



13.6 (br, 1H)


49
[CDCl3] 0.95 (dt, 6H); 1.20 (d, 3H); 1.80 (m, 1H); 4.07 (m, 1H); 6.90 (d, 1H); 8.70 (d, 1H);



9.30 (d, br, 1H); 13.6 (br)


51
[DMSO] 0.85 (t, 6H); 1.45 (m, 2H); 1.55 (m, 2H); 3.80 (m, 1H); 7.33 (d, br, 1H); 8.38 (d, 1H);



8.65 (br, 1H); 13.5 (br, 1H)


54
[CDCl3] 3.40 (s, 6H); 3.62 (t, 2H); 4.50 (t, 1H); 6.89 (d, 1H); 8.65 (d, 1H); 9.30 (br, 1H);



12.4 (br, 1H)


55
[CDCl3] 1.21 (t, 6H); 3.60 (m, 4H); 3.72 (m, 2H); 4.61 (t, 1H); 6.88 (d, 1H); 8.61 (d, 1H);



9.28 (br, 1H), 12.0 (br)


56
[DMSO] 3.40 (m, 2H); 3.53 (m, 2H); 7.32 (d, br, 1H); 8.45 (d, 1H); 9.05 (br, 1H); 13.6 (br,



1H)


57
[CDCl3] 3.40 (s, 3H); 3.56 (t, 2H); 3.64 (m, 2H); 6.90 (d, 1H), 8.65 (d, 1H); 9.35 (br, 1H)


64
[CDCl3] 1.25 (d, 3H); 3.40 (s, 3H); 3.43 (d, 2H); 4.37 (m, 1H); 6.89 (d, 1H); 8.64 (d, 1H);



9.30 (d, br, 1H); 13.0 (br, 1H)


66
[CDCl3] 1.90 (m, 2H); 3.34 (s, 3H); 3.46 (t, 2H); 3.55 (q, 2H); 6.90 (d, 1H); 8.60 (d, 1H);



9.23 (br, 1H); 12.5 (br)


71
[CDCl3] 3.80 (s, 3H); 4.22 (d, 2H); 6.88 (d, 1H); 8.64 (d, 1H); 9.62 (t, 1H),


72
[CDCl3] 3.10 (s, 3H); 3.75 (s, 3H); 4.25 (s, 2H); 7.18 (d, 1H); 7.80 (d, 1H)


75
[CDCl3] 2.64 (t, 2H); 3.69 (s, 3H); 3.73 (m, 2H); 6.88 (d, 1H); 8.61 (d, 1H); 9.41 (t, br, 1H);



12.2 (br, 1H)


76
[CDCl3] 3.83 (s, 6H); 5.42 (d, 1H); 6.90 (d, 1H); 8.63 (d, 1H), 10.2 (br, 1H),


77
[CDCl3] 0.99 (t, 6H); 1.25 (t, 3H)1.75 (m, 3H); 4.20 (m, 2H); 4.72 (m, 1H); 6.90 (d, 1H);



8.64 (d, 1H); 9.60 (d, br, 1H)


78
[CDCl3] 1.05 (t, 6H); 2.30 (m, 1H); 3.78 (s, 3H); 4.72 (m, 1H); 6.90 (d, 1H); 8.70 (d, 1H);



9.76 (d, br, 1H), 13.6 (br, 1H)


79
[CDCl3] 1.35 (t, 3H); 4.10 (q, 2H); 6.91 (d, 1H); 8.71 (d, 1H); 11.46 (s, 1H)


80
[CDCl3] 3.41 (s, 3H); 3.68 (s, 3H); 7.18 (d, 1H); 8.32 (d, 1H)


81
[CDCl3] 4.50 (d, 2H); 5.3 (m, 2H); 6.0 (m, 1H); 6.90 (d, 1H); 8.70 (d, 1H); 11.43 (s, 1H)


82
[CDCl3] 1.36 (s, 9H); 6.92 (d, 1H); 8.72 (d, 1H); 11.22 (s, 1H); 13.0 (br, 1H)


92
[CDCl3] 4.62 (d, 2H), 6.84 (d, 1H); 7.3 (m, 5H); 8.70 (d, 1H); 9.65 (br, 1H), 13.0 (br, 1H)


93
[CDCl3] 2.95 (s, 3H); 4.65 (br, 2H); 7.05 (d, 1H); 7.3 (m, 5H), 7.82 (d, 1H); 11.7 (br)


94
[DMSO] 4.55 (d, 2H); 7.33 (d, 1H); 7.37 (dd, 1H); 7.75 (dt, 1H); 8.40 (d, 1H); 8.48 (dd, 1H);



8.58 (s, 1H); 9.45 (br, 1H); 13.4 (br, 1H)


95
[DMSO] 4.55 (d, 2H); 7.30 (d, br, 1H); 7.50 (d, 1H); 7.80 (dd, 1H); 8.37 (m, 2H); 9.55 (br,



1H); 13.4 (br, 1H)


96
[CDCl3] 1.59 (d, 3H); 5.25 (m, 1H); 6.88 (d, 1H); 7.2-7.4 (m, 5H); 8.68 (d, 1H); 9.75 (d, br,



1H); 13.5 (br, 1H)


97
[CDCl3] 2.94 (t, 2H); 3.70 (m, 2H); 6.85 (d, 1H); 7.2-7.4 (m, 5H); 8.62 (d, 1H); 9.24 (br, 1H)


98
[CDCl3] 4.81 (d, 2H); 6.85 (d, 1H); 7.40 (t, 1H); 7.52 (t, 1H); 7.61 (d, 1H); 7.67 (d, 1H);



8.68 (d, 1H); 9.68 (t, br, 1H)


99
[DMSO] 2.28 (q, 2H); 3.20 (q, 2H); 4.03 (t, 1H); 7.1-7.4 (m, 11H); 8.35 (d, 1H); 9.0 (br),



13.4 (br, 1H)


100
[CDCl3] 3.45-3.55 (br, 4H); 3.75 (m, 4H); 7.03 (d, 1H); 7.80 (d, 1H); 11.3 (br, 1H)


101
[CDCl3] 1.65 (m, 6H); 3.52 (m, 4H); 7.10 (d, 1H); 7.72 (d, 1H)


102
[CDCl3] 3.06 (t, 2H); 3.90 (m, 2H); 4.65 (m, 2H); 7.08 (d, 1H); 7.90 (d, 1H); 11.0 (br)


103
[CDCl3] 2.00 (m, 4H); 3.67 (m, 4H); 7.20 (d, 1H); 7.97 (d, 1H), 11.7 (br, 1H)


104
[CDCl3] 1.30 (m, 3H); 1.65 (m, 1H); 1.85 (m, 1H); 2.00 (m, 1H); 2.19 (m, 1H); 3.62 (m, 2H);



4.30 (m, 1H); 7.10 (d, 1H); 7.89 (d, 1H)


105
[CDCl3] 3.25 (s, 3H); 3.35 (3.3H); 7.25 (d, 1H); 8.58 (d, 1H); 8.76 (s, 1H)


112
[CDCl3] 1.95 (m, 1H); 2.65 (m, 1H); 2.90 (m, 1H); 3.05 (m, 1H); 5.60 (m, 1H); 6.85 (d, 1H);



7.2-7.4 (m, 4H); 8.68 (d, 1H); 9.52 (d, br, 1H)


113
[CDCl3] 1.60 (m, 1H), 1.90 (m, 2H), 2.01 (m, 1H); 3.42 (m, 1H), 3.65-3.82 (m, 2H), 3.90 (m,



1H), 4.09 (m, 1H); 6.88 (d, 1H); 8.63 (d, 1H); 9.37 (br, 1H)


114
[DMSO] 7.35 (d, 1H); 8.10 (br, 1H); 8.40 (d, 1H); 8.41 (br, 1H); 13.6 (br, 1H)


115
[CDCl3] 3.01 (d, 3H); 6.81 (d, 1H); 8.63 (d, 1H); 9.22 (br, 1H); 11.7 (br, 1H)


116
[CDCl3] 1.25 (t, 3H); 3.5 (m, 2H); 6.85 (d, 1H); 8.66 (d, 1H), 9.33 (br, 1H), 13.0 (br, 1H)


117
[CDCl3] 1.01 (t, 3H); 1.62 (m, 2H); 3.42 (m, 2H); 6.86 (d, 1H); 8.66 (d, 1H); 9.35 (br, 1H);



12.6 (br, 1H)


118
[CDCl3] 1.27 (d, 6H); 4.25 (m, 1H); 6.85 (d, 1H); 8.64 (d, 1H); 9.27 (br, 1H); 13.1 (br, 1H)


119
[CDCl3] 0.62 (m, 2H); 0.85 (m, 2H); 3.02 (m, 1H); 6.84 (d, 1H); 8.78 (d, 1H), 9.33 (br, 1H)


120
[CDCl3] 0.98 (t, 3H); 1.41 (m, 2H); 1.61 (m, 2H); 3.45 (q, 2H); 6.83 (d, 1H); 8.65 (d, 1H);



9.33 (br, 1H); 12.9 (br, 1H)


121
[CDCl3] 1.80 (m, 2H); 2.05 (m, 2H); 2.44 (m, 2H); 4.58 (m, 1H); 6.84 (d, 1H); 8.63 (d, 1H);



9.60 (br, 1H); 13.1 (br)


122
[CDCl3] 1.46 (s, 9H); 6.86 (d, 1H); 8.62 (d, 1H); 9.34 (br, 1H); 13.4 (br, 1H)


123
[CDCl3] 3.08 (s, 6H); 7.06 (d, 1H); 7.79 (d, 1H)


124
[CDCl3] 1.23 (t, 3H); 3.04 (s, 3H); 3.46 (m, 2H); 7.02 (d, 1H); 7.72 (d, 1H)


125
[CDCl3] 0.92 (t, 3H); 1.30 (br, 2H); 1.60 (m, 2H); 3.04 (s, 3H); 3.41 (br, 2H); 7.04 (d, 1H);



7.71 (d, 1H)


127
[CDCl3] 1.20 (d, 6H); 2.90 (s, 3H); 4.05 (m, br, 1H); 7.00 (d, 1H); 7.68 (d, 1H)


128
[CDCl3] 1.20 (t, 6H); 3.41 (m, 4H); 6.98 (d, 1H); 7.66 d, 1H); 11.0 (br)


130
[CDCl3] 1.20 (m, 9H); 3.40 (q, 2H); 4.06 (m, br, 1H); 6.98 (d, 1H); 8.64 (d, 1H); 10.2 (br)


132
[CDCl3] 1.5-1.8 (m, 8H); 4.40 (m, 1H); 6.85 (d, 1H); 8.65 (d, 1H); 9.40 (d, br, 1H); 13.1 (br,



1H)


133
[CDCl3] 1.2-1.7 (m, 6H); 1.80 (m, 2H); 2.00 (m, 2H); 3.98 (m, 1H); 6.85 (d, 1H); 8.64 (d, 1H);



9.30 (d, br, 1H); 13.0 (br)


134
[CDCl3] 0.90 (t, 3H); 1.40 (m, 4H); 1.62 (m, 2H); 3.44 (m, 2H); 6.84 (d, 1H); 8.64 (d, 1H);



9.30 (br, 1H)


136
[CDCl3] 0.30 (m, 2H); 0.59 (m, 2H); 1.05 (m, 1H); 3.32 (m, 2H); 6.86 (d, 1H), 8.65 (d, 1H);



9.40 (br)


138
[CDCl3] 1.00 (s, 9H); 3.26 (d, 2H); 6.86 (d, 1H); 8.70 (d, 1H); 9.42 (br, 1H); 12.5 (br, 1H)


139
[DMSO] 4.25 (dt, 2H); 7.25 (d, 1H); 8.40 (d, 1H); 9.35 (br, 1H); 13.5 (br, 1H)


140
[CDCl3] 4.15 (m, 2H); 6.88 (d, 1H); 8.70 (d, 1H); 9.80 (br, 1H)


141
[CDCl3] 4.20 (dt; 2H); 6.90 (d, 1H); 8.70 (d, 1H); 9.83 (t, br, 1H); 12.80 (br)


144
[CDCl3] 1.00 (d, 6H); 1.90 (m, 1H); 3.30 (t, 2H); 6.83 (d, 1H); 8.65 (d, 1H); 9.35 (br, 1H);



12.2 (br)


146
[CDCl3] 0.96 (d, 6H); 1.50 (m, 2H); 1.70 (m, 1H); 3.48 (m, 2H); 6.83 (d, 1H); 8.67 (d, 1H);



9.30 (br, 1H), 12.9 (br, 1H)


148
[CDCl3] 4.62 (d, 2H); 5.36 (dd, 2H); 5.95 (m, 1H); 7.80 (d, 1H); 8.65 (d, 1H)


150
[CDCl3] 4.0 (m, 4H); 5.22 (d, 4H); 5.80 (m, 2H); 6.93 (d, 1H); 7.72 (d, 1H)


152
[CDCl3] 1.80 (s, 3H); 4.02 (d, 2H); 4.90 (d, 2H); 6.85 (d 1H); 8.68 (d, 1H); 9.48 (br, 1H);



12.8 (br, 1H)


153
[CDCl3] 2.26 (t, 1H); 4.23 (m, 2H); 6.84 (d, 1H); 8.64 (d, 1H); 9.58 (br, 1H); 12.4 (br)


154
[CDCl3] 2.30 (s, 1H); 3.12 (s, 3H); 4.24 (br, 2H); 7.01 (d, 1H); 7.82 (d, 1H); 10.9 (br)


155
[CDCl3] 0.98 (t, 3H); 1.22 (d, 3H); 1.59 (m, 2H); 4.10 (m, 1H); 6.85 (d, 1H); 8.65 (d, 1H);



9.26 (d, br, 1H); 13.4 (br, 1H)


157
[CDCl3] 0.92 (t, 3H); 1.22 (d, 3H); 1.40 (m, 2H); 1.55 (m, 2H); 4.20 (m, 1H); 6.85 (d, 1H);



8.68 (d, 1H); 9.30 (d, br, 1H)


158
[CDCl3] 0.87 (t, 3H); 1.12 (d, 3H); 1.30 (m, 4H); 1.58 (m, 4H); 4.15 (m, 1H); 6.84 (d, 1H);



8.65 (d, 1H); 9.24 (br, 1H), 13.1 (br)


161
[CDCl3] 0.90 (d, 6H); 1.22 (d, 3H), 1.30 (m, 1H); 1.55 (m, 2H); 4.23 (m, 1H); 6.86 (d, 1H);



8.64 (d, 1H); 9.20 (d, br, 1H); 13.0 (br, 1H)


162
[CDCl3] 0.98 (s, 9H); 1.20 (d, 3H); 4.10 (m, 1H); 6.87 (d, 1H); 8.70 (d, 1H); 9.38 (d, br, 1H),



13.2 (br, 1H)


163
[CDCl3] 0.95 (dt, 6H); 1.20 (d, 3H); 1.82 (m, 1H); 4.05 (m, 1H); 6.84 (d, 1H); 8.68 (d, 1H);



9.30 (d, br, 1H); 13.1 (br)


165
[CDCl3] 0.96 (t, 6H); 1.50 (m, 2H); 1.65 (m, 2H); 4.00 (m, 1H); 6.85 (d, 1H); 8.68 (d, 1H);



9.22 (d, br, 1H); 13.5 (br, 1H)


166
[CDCl3] 0.90 (t, 3H); 1.41 (s; 6H); 1.85 (q, 2H); 6.82 (d, 1H); 8.61 (d, 1H); 9.20 (br, 1H);



13.1 (br)


168
[CDCl3] 3.40 (s, 6H); 3.63 (t, 2H); 4.50 (t, 1H); 6.85 (d, 1H); 8.65 (d, 1H); 9.40 (br, 1H);



12.4 (br, 1H)


169
[CDCl3] 1.21 (t, 6H); 3.60 (m, 4H); 3.74 (m, 1H); 4.62 (t, 1H); 6.84 (d, 1H); 8.60 (d, 1H);



9.35 (br, 1H), 11.5 (br)


171
[CDCl3] 3.40 (s, 3H); 3.58 (m, 2H); 3.67 (m, 2H); 6.84 (d, 1H), 8.62 (d, 1H); 9.40 (br, 1H)


178
[CDCl3] 1.24 (d, 3H); 3.40 (s, 3H); 3.42 (d, 2H); 4.40 (m, 1H); 6.86 (d, 1H); 8.64 (d, 1H);



9.35 (br, 1H); 13.0 (br)


180
[DMSO] 1.75 (m, 2H); 3.22 (s, 3H); 3.36 (m, 4H); 7.3 (br, 1H); 8.4 (d, 1H); 9.0 (br); 13.4 (br,



1H)


185
[DMSO] 3.65 (s, 3H); 4.12 (d, 2H); 7.28 (d, br, 1H); 8.42 (d, 1H); 9.25 (t, br, 1H), 13.6 (br,



1H)


189
[CDCl3] 2.66 (t, 2H); 3.70 (s, 3H); 3.76 (m, 2H); 6.83 (d, 1H); 8.61 (d, 1H); 9.51 (t, br, 1H);



12.4 (br, 1H)


193
[CDCl3] 1.37 (t, 3H); 4.08 (q, 2H); 6.88 (d, 1H); 8.69 (d, 1H); 11.48 (s, 1H)


194
[CDCl3] 3.88 (s, 3H); 6.88 (d, 1H); 8.65 (d, 1H); 11.5 (s, 1H)


195
[CDCl3] 4.50 (d, 2H); 5.34 (m, 2H); 6.05 (m, 1H); 6.88 (d, 1H); 8.70 (d, 1H); 11.44 (s, 1H)


196
[CDCl3] 1.39 (s, 9H); 6.88 (d, 1H); 8.70 (d, 1H); 11.22 (s, 1H)


206
[CDCl3] 4.62 (d, 2H), 6.82 (d, 1H); 7.2-7.3 (m, 5H); 8.68 (d, 1H); 9.65 (t, br, 1H), 12.8 (br,



1H)


207
[CDCl3] 2.99 (s, 3H); 4.67 (br, 2H); 7.00 (d, 1H); 7.3-7.4 (m, 5H), 7.78 (d, 1H); 10.2 (br)


210
[CDCl3] 1.60 (d, 3H); 5.30 (m, 1H); 6.85 (d, 1H); 7.2-7.4 (m, 5H); 8.65 (d, 1H); 9.78 (d, br,



1H); 13.2 (br, 1H)


211
[CDCl3] 2.95 (t, 2H); 3.70 (m, 2H); 6.82 (d, 1H); 7.2-7.35 (m, 5H); 8.63 (d, 1H); 9.40 (t, br,



1H); 12.2 (br, 1H)


214
[CDCl3] 3.45-3.55 (br, 4H); 3.75 (m, 4H); 6.96 (d, 1H); 7.78 (d, 1H)


215
[CDCl3] 1.65 (m, 6H); 3.53 (m, 4H); 7.00 (d, 1H); 7.70 (d, 1H)


216
[CDCl3] 3.05 (t, 2H); 3.92 (m, 2H); 4.66 (m, 2H); 7.04 (d, 1H); 7.86 (d, 1H); 10.4 (br)


217
[CDCl3] 2.00 (m, 4H); 3.70 (m, 4H); 7.16 (d, 1H); 7.97 (d, 1H), 11.7 (br, 1H)


218
[CDCl3] 1.30 (m, 3H); 1.65 (m, 1H); 1.85 (m, 1H); 2.04 (m, 1H); 2.20 (m, 1H); 3.63 (m, 2H);



4.33 (m, 1H); 7.12 (d, 1H); 7.89 (d, 1H), 11.5 (br, 1H)


227
[CDCl3] 1.60 (m, 1H), 1.90 (m, 2H), 2.00 (m, 1H); 3.42 (m, 1H), 3.65-3.82 (m, 2H), 3.90 (m,



1H), 4.10 (m, 1H); 6.88 (d, 1H); 8.65 (d, 1H); 9.5 (br, 1H)


228
[DMSO] 6.80 (br, 1H); 6.90 (t, 1H); 7.72 (br, 1H); 8.40 (d, 1H); 8.90 (br, 1H); 13.20 (br, 1H)


229
[DMSO] 2.82 (d, 3H); 6.75 (d, br, 1H); 6.90 (t, 1H); 8.89 (d, 1H); 9.50 (br, 1H); 13.2 (br, 1H)


230
[DMSO] 1.11 (t, 3H); 3.32 (m, 2H); 6.75 (d, br, 1H); 6.90 (t, 1H); 8.39 (d, 1H), 9.60 (br, 1H),



13.2 (br, 1H)


232
[CDCl3] 1.25 (d, 6H); 4.22 (m, 1H); 6.55 (t, 1H); 6.69 (d, 1H); 8.64 (d, 1H); 9.42 (d, br, 1H);



13.0 (br, 1H)


233
[DMSO] 0.51 (m, 2H); 0.74 (m, 2H); 2.84 (m, 1H); 6.79 (d, br, 1H); 6.90 (t, 1H); 8.37 (d, 1H);



9.65 (br, 1H); 13.1 (br, 1H)


250
[DMSO] 0.23 (m, 2H); 0.46 (m, 2H); 1.02 (m, 1H); 3.20 (m, 2H); 6.75 (br, 1H), 6.92 (t, 1H);



8.40 (d, 1H); 9.70 (br, 1H); 13.1 (br, 1H)


252
[DMSO] 0.91 (s, 9H); 3.15 (d, 2H); 6.80 (br, 1H); 6.91 (t, 1H); 8.40 (d, 1H); 9.85 (br, 1H);



13.2 (br, 1H)


258
[DMSO] 0.90 (d, 6H); 1.80 (m, 1H); 3.15 (t, 2H); 6.80 (br, 1H); 6.91 (t, 1H); 8.40 (d, 1H);



9.73 (br, 1H); 13.1 (br, 1H)


262
[DMSO] 3.96 (m, 2H); 5.15 (dd, 2H); 5.94 (m, 1H); 6.80 (br, 1H); 6.92 (t, 1H); 8.40 (d, 1H);



9.75 (br, 1H); 13.2 (br, 1H)


271
[CDCl3] 0.92 (t, 3H); 1.25 (d, 3H); 1.42 (m, 2H); 1.55 (m, 2H); 4.19 (m, 1H); 6.60 (t, 1H);



6.73 (d, 1H); 8.66 (d, 1H); 9.50 (d, br, 1H)


272
[CDCl3] 0.90 (t, 3H); 1.2-1.4 (m, 9H); 1.58 (m, 2H); 4.17 (m, 1H); 6.60 (t, 1H); 6.75 (d, 1H);



8.68 (d, 1H); 9.48 (d, br, 1H)


279
[CDCl3] 0.85 (t, 6H); 1.45 (m, 2H); 1.55 (m, 2H); 3.80 (m, 1H); 6.80 (br, 1H); 6.91 (t, 1H);



8.40 (d, 1H); 9.51 (br, 1H); 13.1 (br, 1H)


280
[DMSO] 0.86 (t, 3H); 1.12 (d, 3H); 1.50 (m, 2H); 3.90 (m, 1H); 6.75 (br, 1H); 6.91 (t, 1H);



8.39 (d, 1H); 9.57 (br, 1H); 13.1 (br, 1H)


285
[DMSO] 3.29 (s, 3H); 3.46 (m, 4H); 6.76 (br, 1H), 6.91 (t, 1H); 8.50 (d, 1H); 9.73 (br, 1H),



13.1 (br, 1H)


291
[DMSO] 1.14 (d, 3H); 3.27 (s, 3H); 3.35 (m, 2H); 4.15 (m, 1H); 6.80 (br, 1H); 6.91 (t, 1H);



8.40 (d, 1H); 9.70 (br, 1H); 13.1 (br, 1H))


293
[DMSO] 1.72 (m, 2H); 3.22 (s, 3H); 3.37 (m, 4H); 6.75 (br, 1H); 6.90 (t, 1H); 8.40 (d, 1H);



9.70 (br, 1H)); 13.2 (br, 1H)


341
[DMSO] 7.45 (d, 1H); 8.15 (br, 1H); 8.45 (br, 1H); 8.50 (d, 1H); 13.7 (br, 1H)


342
[CDCl3] 3.01 (d, 3H); 6.90 (d, 1H); 8.72 (d, 1H); 9.34 (br, 1H)


343
[DMSO] 1.11 (t, 3H); 3.31 (m, 2H); 7.41 (d, 1H); 8.42 (d, 1H); 8.85 (br, 1H), 13.4 (br, 1H)


344
[CDCl3] 1.02 (t, 3H); 1.61 (m, 2H); 3.42 (q, 2H); 6.88 (d, 1H); 8.72 (d, 1H); 9.38 (br, 1H)


345
[CDCl3] 1.25 (d, 6H); 4.25 (m, 1H); 6.90 (d, 1H); 8.72 (d, 1H); 9.30 (d, br, 1H); 13.8 (br, 1H)


346
[CDCl3] 0.60 (m, 2H); 0.88 (m, 2H); 3.02 (m, 1H); 6.90 (d, 1H); 8.72 (d, 1H); 9.42 (br, 1H);



13.4 (br)


347
[DMSO] 0.88 (t, 3H); 1.34 (m, 2H); 1.50 (m, 2H); 3.31 (q, 2H); 7.27 (d, 1H); 8.35 (d, 1H);



9.21 (br, 1H); 12.4 (br, 1H)


348
[DMSO] 1.70 (m, 2H); 2.02 (m, 2H); 2.27 (m, 2H); 4.40 (m, 1H); 7.41 (d, 1H); 8.48 (d, 1H);



9.00 (br, 1H); 13.4 (br, 1H)


349
[DMSO] 1.36 (s, 9H); 7.35 (d, br, 1H); 8.40 (d, 1H); 8.60 (br, 1H); 13.3 (br, 1H)


350
[CDCl3] 3.08 (s, 6H); 7.08 (d, 1H); 7.81 (d, 1H)


355
[CDCl3] 1.21 (t, 6H); 3.42 (m, 4H); 7.04 (d, 1H); 7.71 (d, 1H); 10.8 (br)


363
[DMSO] 0.27 (m, 2H); 0.46 (m, 2H); 1.05 (m, 1H); 3.15 (m, 2H); 7.45 (d, br, 1H); 8.45 (d,



1H); 8.95 (br, 1H); 13.4 (br, 1H)


365
[DMSO] 0.91 (s, 9H); 3.15 (d, 2H); 7.38 (d, br, 1H); 8.40 (d, 1H); 8.83 (br, 1H); 13.4 (br, 1H)


373
[DMSO] 0.90 (d, 6H); 1.42 (m, 2H); 1.63 (m, 1H); 3.33 (m, 2H); 7.40 (d, br, 1H); 8.40 (d,



1H); 8.83 (br, 1H), 13.4 (br, 1H)


375
[DMSO] 3.95 (m, 2H); 5.15 (dd, 2H); 5.90 (m, 1H); 7.40 (d, 1H); 8.41 (d, 1H); 8.98 (br, 1H);



13.4 (br, 1H)


379
[DMSO] 1.73 (s, 3H); 3.88 (m, 2H); 4.75 (d, 2H); 7.40 (d, br, 1H); 8.41 (d, 1H); 8.97 (br, 1H);



13.4 (br, 1H)


380
[DMSO] 3.15 (t, 1H); 4.21 (m, 2H); 7.40 (d, 1H); 8.40 (d, 1H); 9.12 (br, 1H); 13.3 (br, 1H)


382
[CDCl3] 0.97 (t, 3H); 1.22 (d, 3H); 1.59 (m, 2H); 4.10 (m, 1H); 6.88 (d, 1H); 8.72 (d, 1H);



9.24 (d, br, 1H); 13.6 (br)


384
[CDCl3] 0.92 (t, 3H); 1.21 (d, 3H); 1.40 (m, 2H); 1.50 (m, 2H); 4.20 (m, 1H); 6.88 (d, 1H);



8.72 (d, 1H); 9.28 (d, br, 1H)


385
[DMSO] 0.85 (t, 3H); 1.1-1.35 (m, 9H); 1.50 (m, 2H); 4.00 (m, 1H); 7.41 (d, 1H); 8.40 (d,



1H); 8.65 (br, 1H); 13.4 (br, 1H)


388
[DMSO] 0.88 (d, 6H); 1.15 (d, 3H), 1.28 (m, 1H); 1.48 (m, 1H); 1.62 (m, 1H); 4.11 (m, 1H);



7.40 (d, br, 1H); 8.40 (d, 1H); 8.52 (d, br, 1H); 13.4 (br, 1H)


389
[DMSO] 0.90 (s, 9H); 1.10 (d, 3H); 3.90 (m, 1H); 7.38 (d, br, 1H); 8.40 (d, 1H); 8.70 (br, 1H),



13.4 (br, 1H)


390
[DMSO] 0.79 (dt, 6H); 1.10 (d, 3H); 1.75 (m, 1H); 3.87 (m, 1H); 7.40 (d, br, 1H); 8.41 (d,



1H); 8.65 (d, br, 1H); 13.4 (br, 1H)


392
[CDCl3] 0.95 (t, 6H); 1.50 (m, 2H); 1.65 (m, 2H); 4.00 (m, 1H); 6.90 (d, 1H); 8.75 (d, 1H);



9.20 (d, br, 1H); 13.7 (br, 1H)


395
[DMSO] 3.30 (s, 6H); 3.42 (t, 2H); 4.50 (t, 1H); 7.40 (d, br, 1H); 8.45 (d, 1H); 8.90 (br, 1H);



13.4 (br, 1H)


397
[DMSO] 3.38 (m, 2H); 3.52 (m, 2H); 4.80 (t, 1H); 7.40 (d, br, 1H); 8.43 (d, 1H); 8.95 (br,



1H); 13.4 (br, 1H)


398
[CDCl3] 3.38 (s, 3H); 3.58 (m, 2H); 3.65 (m, 2H); 6.88 (d, 1H), 8.70 (d, 1H); 9.43 (br, 1H)


405
[CDCl3] 1.25 (d, 3H); 3.38 (s, 3H); 3.42 (d, 2H); 4.40 (m, 1H); 6.88 (d, 1H); 8.70 (d, 1H);



9.38 (d, br, 1H)


407
[CDCl3] 1.89 (m, 2H); 3.32 (s, 3H); 3.48 (t, 2H); 3.58 (m, 2H); 6.92 (d, 1H); 8.64 (d, 1H);



9.30 (br, 1H)


455
[DMSO] 8.25 (br, 1H); 8.35 (br, 1H); 8.50 (s, 1H); 13.8 (br, 1H)


456
[DMSO] 2.84 (d, 3H); 8.40 (s, 1H); 8.72 (d, br, 1H)


457
[DMSO] 1.12 (t, 3H); 3.35 (q, 2H); 8.40 (s, 1H); 8.75 (t, br, 1H); 13.5 (br, 1H)


458
[DMSO] 0.89 (t, 3H); 1.52 (m, 2H); 3.25 (m, 2H); 8.41 (s, 1H); 8.73 (t, br, 1H); 13.4 (br, 1H)


459
[DMSO] 1.19 (d, 6H); 4.08 (m, 1H); 8.43 (s, 1H); 8.59 (d, br, 1H); 13.4 (br, 1H)


460
[DMSO] 0.59 (m, 2H); 0.75 (m, 2H); 2.87 (m, 1H); 8.39 (s, 1H); 8.73 (d, br, 1H)


461
[DMSO] 0.90 (t, 3H); 1.32 (m, 2H); 1.50 (m, 2H); 3.30 (m, 2H); 8.41 (s, 1H); 8.74 (t, br, 1H);



13.5 (br, 1H)


462
[DMSO] 1.70 (m, 2H); 2.03 (m, 2H); 2.25 (m, 2H); 4.40 (m, 1H); 8.41 (s, 1H); 8.90 (d, br,



1H); 13.5 (br, 1H)


477
[DMSO] 0.25 (m, 2H); 0.47 (m, 2H); 1.02 (m, 1H); 3.19 (t, 2H); 8.45 (s, 1H); 8.80 (t, br, 1H)


479
[DMSO] 0.90 (s, 9H); 3.14 (d, 2H); 8.38 (s, 1H); 8.60 (t, br, 1H); 13.7 (br, 1H)


485
[DMSO] 0.89 (d, 6H); 1.82 (m, 1H); 3.13 (t, 2H); 8.40 (s, 1H); 8.72 (t, br, 1H)


487
[DMSO] 0.90 (d, 6H); 1.41 (q, 2H); 1.62 (m, 1H); 3.32 (m, 2H); 8.40 (s, 1H); 8.72 (t, br, 1H);



13.5 (br, 1H)


489
[CDCl3] 4.10 (d, 2H); 5.25 (dd, 2H); 5.93 (m, 1H); 8.60 (s, 1H); 9.10 (br, 1H); 12.4 (br, 1H)


493
[DMSO] 1.71 (s, 3H); 3.86 (d, 2H); 4.84 (d, 2H); 8.40 (s, 1H); 8.85 (t, br, 1H); 13.5 (br)


494
[DMSO] 3.17 (m, 1H); 4.11 (m, 2H); 8.39 (s, 1H); 8.98 (t, br, 1H), 13.4 (br)


496
[CDCl3] 0.95 (t, 3H); 1.25 (d, 3H); 1.60 (m, 2H); 4.12 (m, 1H); 8.48 (s, 1H); 8.52 (br, 1H)


498
[CDCl3] 0.95 (t, 3H); 1.25 (d, 3H); 1.40 (m, 2H); 1.55 (m, 2H); 4.17 (m, 1H); 8.53 (s, 1H);



8.70 (br, 1H)


499
[CDCl3] 0.87 (t, 3H); 1.21 (d, 3H); 1.32 (m, 6H); 1.53 (m, 2H); 4.15 (m, 1H); 8.62 (s, 1H);



8.99 (d, br, 1H); 13.0 (br)


502
[CDCl3] 0.91 (d, 6H); 1.23 (d, 3H); 1.35 (m, 1H); 1.48 (m, 1H); 1.66 (m, 1H); 4.25 (m, 1H);



8.62 (s, 1H); 8.96 (d, br, 1H); 12.9 (br, 1H)


504
[CDCl3] 0.95 (m, 6H); 1.18 (d, 3H); 1.81 (m, 1H); 4.07 (m, 1H); 8.61 (s, 1H); 8.97 (d, br,



1H); 12.9 (br, 1H)


506
[CDCl3] 0.94 (t, 6H); 1.50 (m, 2H); 1.65 (m, 2H), 4.00 (m, 1H); 8.56 (s, 1H); 8.73 (d, br, 1H)


512
[DMSO] 3.28 (s, 3H); 3.48 (m, 4H); 8.42 (s, 1H); 8.78 (br, 1H); 13.7 (br, 1H)


519
[DMSO] 1.16 (d, 3H); 3.30 (s, 3H); 3.42 (m, 2H); 4.18 (m, 1H); 8.42 (s, 1H); 8.60 (d, br, 1H);



13.7 (br, 1H)


521
[DMSO] 1.74 (m, 2H); 3.26 (s, 3H); 3.39 (m, 4H); 8.40 (s, 1H); 8.80 (t, br, 1H); 13.6 (br, 1H)


569
[DMSO] 8.25 (br, 1H); 8.35 (br, 1H); 8.50 (s, 1H); 13.7 (br, 1H)


570
[DMSO] 2.82 (d, 3H); 8.40 (s, 1H); 8.71 (br, 1H); 13.5 (br, 1H)


571
[DMSO] 1.12 (t, 3H); 3.35 (q, 2H); 8.40 (s, 1H); 8.75 (t, br, 1H); 13.7 (br, 1H)


572
[DMSO] 0.89 (t, 3H); 1.52 (m, 2H); 3.26 (m, 2H); 8.39 (s, 1H); 8.82 (br, 1H)


573
[DMSO] 1.18 (d, 6H); 4.09 (m, 1H); 8.42 (s, 1H); 8.53 (d, br, 1H); 13.5 (br, 1H)


574
[DMSO] 0.59 (m, 2H); 0.74 (m, 2H); 2.85 (m, 1H); 8.37 (s, 1H); 8.72 (d, br, 1H)


575
[DMSO] 0.89 (t, 3H); 1.35 (m, 2H); 1.50 (m, 2H); 3.35 (m, 2H); 8.39 (s, 1H); 8.75 (br, 1H)


576
[DMSO] 1.70 (m, 2H); 2.05 (m, 2H); 2.25 (m, 2H); 4.40 (m, 1H); 8.40 (s, 1H); 8.94 (br, 1H)


591
[DMSO] 0.25 (m, 2H); 0.45 (m, 2H); 1.03 (m, 1H); 3.21 (t, 2H); 8.40 (s, 1H); 8.84 (br, 1H)


599
[DMSO] 0.89 (d, 6H); 1.82 (m, 1H); 3.14 (m, 2H); 8.38 (s, 1H); 8.74 (br, 1H)


601
[CDCl3] 0.96 (d, 6H); 1.51 (m, 2H); 1.70 (m, 1H); 3.49 (m, 2H); 8.59 (s, 1H); 9.02 (br, 1H);



12.2 (br)


603
[DMSO] 3.95 (t, 2H); 5.18 (dd, 2H); 5.89 (m, 1H); 8.40 (s, 1H); 8.85 (t, br, 1H); 13.6 (br, 1H)


612
[CDCl3] 0.91 (t, 3H); 1.24 (d, 3H); 1.40 (m, 2H); 1.54 (m, 2H); 4.18 (m, 1H); 8.57 (s, 1H);



8.90 (d, br, 1H); 12.2 (br, 1H)


620
[CDCl3] 0.94 (t, 6H); 1.51 (m, 2H); 1.67 (m, 2H); 3.99 (m, 1H); 8.57 (s, 1H); 8.82 (d, br, 1H)


626
[DMSO] 3.29 (s, 3H); 3.48 (m, 4H); 8.41 (s, 1H); 8.78 (br, 1H); 13.7 (br, 1H)


633
[CDCl3] 1.28 (d, 3H); 3.40 (s, 3H); 3.45 (m, 2H); 4.37 (m, 1H); 8.48 (s, 1H); 8.78 (br, 1H)


635
[DMSO] 1.75 (m, 2H); 3.25 (s, 3H); 3.39 (m, 4H); 8.40 (s, 1H); 8.81 (br, 1H); 13.6 (br, 1H)


797
[DMSO] 8.27 (br, 1H); 8.38 (br, 1H); 8.52 (s, 1H); 13.7 (br, 1H)


798
[DMSO] 2.82 (d, 3H); 8.40 (s, 1H); 8.75 (d, br, 1H); 13.6 (br, 1H)


799
[DMSO] 1.12 (t, 3H); 3.33 (m, 2H); 8.41 (s, 1H); 8.78 (t, br, 1H); 13.6 (br, 1H)


800
[DMSO] 0.89 (t, 3H); 1.52 (m, 2H); 3.27 (q, 2H); 8.41 (s, 1H); 8.76 (t, br, 1H); 13.5 (br, 1H)


801
[DMSO] 1.18 (d, 6H); 4.09 (m, 1H); 8.42 (s, 1H); 8.60 (d, br, 1H)


802
[DMSO] 0.55 (m, 2H); 0.75 (m, 2H); 2.85 (m, 1H); 8.31 (s, 1H); 9.24 (br, 1H); 13.4 (br, 1H)


803
[DMSO] 0.89 (t, 3H); 1.33 (m, 2H); 1.51 (m, 2H); 3.30 (m, 2H); 8.40 (s, 1H); 8.75 (t, br, 1H),



13.4 (br)


804
[DMSO] 1.70 (m, 2H); 2.04 (m, 2H); 2.25 (m, 2H); 4.39 (m, 1H); 8.43 (s, 1H); 8.95 (d, br,



1H); 13.4 (br, 1H)


806
[DMSO] 2.82 (s, 3H); 2.98 (s, 3H); 8.06 (s, 1H); 12.6 (s, br, 1H)


811
[CDCl3] 1.24 (t, 6H); 3.44 (m, 4H); 7.72 (s, 1H)


819
[DMSO] 0.25 (m, 2H); 0.46 (m, 2H); 1.03 (m, 1H); 3.20 (t, 2H); 8.45 (s, 1H); 8.87 (t, br, 1H);



13.4 (br, 1H)


821
[DMSO] 0.90 (s, 9H); 3.13 (d, 2H); 8.37 (s, 1H); 8.61 (t, br, 1H); 13.4 (br, 1H)


827
[DMSO] 0.88 (d, 6H); 1.82 (m, 1H); 3.13 (t, 2H); 8.40 (s, 1H); 8.76 (t, br, 1H); 13.5 (br, 1H)


829
[DMSO] 0.90 (d, 6H); 1.42 (m, 2H); 1.61 (m, 1H); 3.30 (m, 2H); 8.41 (s, 1H); 8.76 (t, br, 1H);



13.5 (br, 1H)


831
[DMSO] 3.95 (t, 2H); 5.19 (dd, 2H); 5.89 (m, 1H); 8.41 (s, 1H); 8.88 (t, br, 1H); 13.5 (br, 1H)


835
[DMSO] 1.72 (s, 3H); 3.87 (d, 2H); 4.86 (d, 2H); 8.39 (s, 1H); 8.90 (t, br, 1H); 13.4 (br, 1H)


836
[DMSO] 3.18 (m, 1H); 4.10 (m, 2H); 8.36 (s, 1H); 9.01 (t, br, 1H); 13.4 (br, 1H)


838
[DMSO] 0.88 (t, 3H); 1.14 (d, 3H); 1.51 (m, 2H); 3.91 (m, 1H); 8.41 (s, 1H); 8.54 (d, br, 1H);



13.5 (br, 1H)


840
[DMSO] 0.88 (t, 3H); 1.14 (d, 3H); 1.33 (m, 2H); 1.47 (m, 2H); 4.01 (m, 1H); 8.42 (s, 1H);



853 (d, br, 1H); 13.5 (br, 1H)


841
[DMSO] 0.85 (t, 3H); 1.14 (d, 3H); 1.28 (m, 6H); 1.49 (m, 2H); 3.98 (m, 1H); 8.41 (s, 1H);



8.60 (d, br, 1H); 13.5 (br, 1H)


844
[DMSO] 0.87 (d, 6H); 1.14 (d, 3H); 1.27 (m, 1H); 1.48 (m, 1H); 1.62 (m, 1H); 4.09 (m, 1H);



8.41 (s, 1H); 8.52 (d, br, 1H); 13.5 (br, 1H)


845
[DMSO] 0.90 (s, 9H); 1.08 (d, 3H); 3.90 (m, 1H); 8.35 (s, 1H); 8.38 (d, br, 1H); 13.4 (br)


846
[DMSO] 0.89 (d, 6H); 1.12 (d, 3H); 1.75 (m, 1H); 3.87 (m, 1H); 8.40 (s, 1H); 8.50 (d, br, 1H);



13.5 (br)


848
[DMSO] 0.87 (t, 6H); 1.44 (m, 2H); 1.55 (m, 2H); 3.79 (m, 1H); 8.40 (s, 1H); 8.42 (d, br,



1H); 13.4 (br, 1H)


851
[CDCl3] 3.42 (s, 6H); 3.63 (t, 2H); 4.50 (t, 1H); 8.55 (s, 1H); 8.95 (t, br, 1H); 12.1 (br, 1H)


853
[CDCl3] 3.65 (m, 2H); 3.86 (m, 2H); 8.47 (s, 1H); 8.98 (br, 1H)


854
[CDCl3] 3.39 (s, 3H); 3.58 (m, 2H); 3.69 (m, 2H); 8.49 (s, 1H); 8.80 (br, 1H); 11.9 (br, 1H)


861
[CDCl3] 1.28 (d, 3H); 3.38 (s, 3H); 3.45 (m, 2H); 4.39 (m, 1H); 8.51 (s, 1H); 8.85 (br, 1H);



12.4 (br, 1H)


863
[CDCl3] 1.90 (m, 2H); 3.40 (s, 3H); 3.57 (m, 4H); 8.30 (s, 1H); 8.70 (br, 1H)


868
[CDCl3] 3.80 (s, 3H); 4.25 (d, 2H); 8.52 (s, 1H); 9.16 (br, 1H)


909
[DMSO] 8.22 (br, 1H); 8.32 (br, 1H); 8.61 (s, 1H); 13.8 (br, 1H)


910
[DMSO] 2.83 (d, 3H); 8.51 (s, 1H); 8.74 (br, 1H); 13.7 (br, 1H)


911
[DMSO] 1.12 (t, 3H); 3.32 (q, 2H); 8.54 (s, 1H); 8.75 (t, br, 1H); 13.7 (br, 1H)


912
[DMSO] 0.89 (t, 3H); 1.52 (m, 2H); 3.25 (q, 2H); 8.54 (s, 1H); 8.75 (t, br, 1H); 13.6 (br, 1H)


913
[CDCl3] 1.25 (d, 6H); 4.25 (m, 1H); 8.54 (br, 1H); 8.70 (s, 1H)


914
[DMSO] 0.58 (m, 2H); 0.75. (m, 2H); 2.86 (m, 1H); 8.50 (s, 1H); 8.75 (d, 1H); 13.6 (br, 1H)


915
[DMSO] 0.89 (t, 3H); 1.32 (m, 2H); 1.50 (m, 2H); 3.32 (m, 2H); 8.53 (s, 1H); 8.74 (t, br, 1H),



13.5 (br)


916
[DMSO] 1.70 (m, 2H); 2.05 (m, 2H); 2.25 (m, 2H); 4.40 (m, 1H); 8.52 (s, 1H); 8.98 (d, br,



1H); 13.5 (br, 1H)


917
[CDCl3] 1.50 (s, 9H); 8.65 (s, 1H); 8.80 (s, br, 1H); 12.3 (br, 1H)


918
[DMSO] 2.82 (s, 3H); 2.99 (s, 3H); 8.14 (s, 1H); 12.6 (br, 1H)


923
[DMSO] 1.02 (t, 3H); 1.12 (t, 3H); 3.10 (q, 2H); 3.40 (9, 2H); 8.15 (s, 1H); 12.5 (br, 1H)


931
[DMSO] 0.24 (m, 2H); 0.46 (m, 2H); 1.04 (m, 1H); 3.18 (t, 2H); 8.55 (s, 1H); 8.82 (t, br, 1H)


933
[DMSO] 0.90 (s, 9H); 3.13 (d, 2H); 8.50 (s, 1H); 8.61 (t, br, 1H)


939
[DMSO] 0.88 (d, 6H); 1.83 (m, 1H); 3.14 (t, 2H); 8.52 (s, 1H); 8.72 (t, br, 1H); 13.6 (br, 1H)


941
[DMSO] 0.90 (d, 6H); 1.43 (m, 2H); 1.62 (m, 1H); 3.35 (m, 2H); 8.52 (s, 1H); 8.72 (t, br, 1H);



13.5 (br, 1H)


943
[DMSO] 3.94 (t, 2H); 5.18 (dd, 2H); 5.89 (m, 1H); 8.52 (s, 1H); 8.85 (t, br, 1H)


947
[DMSO] 1.72 (s, 3H); 3.87 (d, 2H); 4.85 (d, 2H); 8.51 (s, 1H); 8.87 (t, br, 1H); 13.5 (br)


948
[DMSO] 3.18 (m, 1H); 4.12 (m, 2H); 8.50 (s, 1H); 9.00 (t, br, 1H)


950
[DMSO] 0.92 (t, 3H); 1.21 (d, 3H); 1.57 (m, 2H); 3.97 (m, 1H); 8.55 (d, br, 1H); 8.60 (s, 1H);



13.7 (br, 1H)


952
[CDCl3] 0.90 (t, 3H); 1.24 (d, 3H); 1.40 (m, 2H); 1.55 (m, 2H); 4.18 (m, 1H); 8.72 (s, 1H);



8.90 (d, br, 1H)


953
[DMSO] 0.77 (t, 3H); 1.15 (d, 3H); 1.27 (m, 6H); 1.49 (m, 2H); 3.99 (m, 1H); 8.50 (d, br, 1H);



8.55 (s, 1H); 13.6 (br)


956
[DMSO] 0.88 (d, 6H); 1.15 (d, 3H); 1.27 (m, 1H); 1.48 (m, 1H); 1.62 (m, 1H); 4.10 (m, 1H);



8.50 (d, br, 1H); 8.55 (s, 1H); 13.6 (br, 1H)


957
[DMSO] 0.91 (s, 9H); 1.09 (d, 3H); 3.80 (m, 1H); 8.39 (d, br, 1H); 8.49 (s, 1H); 13.6 (br, 1H)


958
[DMSO] 0.89 (d, 6H); 1.11 (d, 3H); 1.75 (m, 1H); 3.86 (m, 1H); 8.48 (d, br, 1H); 8.52 (s, 1H);



13.6 (br)


960
[CDCl3] 0.95 (t, 6H); 1.50 (m, 2H); 1.62 (m, 2H); 4.00 (m, 1H); 8.73 (s, 1H); 8.90 (d, br, 1H)


963
[CDCl3] 3.43 (s, 6H); 3.65 (t, 2H); 4.50 (t, 1H); 8.62 (s, 1H); 8.78 (br, 1H)


965
[DMSO] 3.40 (m, 2H); 3.52 (m, 2H); 8.57 (s, 1H); 8.78 (t, br, 1H); 13.6 (br, 1H)


966
[DMSO] 3.29 (s, 3H); 3.48 (m, 4H); 8.54 (s, 1H); 8.78 (br, 1H); 13.6 (br, 1H)


973
[CDCl3] 1.29 (d, 3H); 3.40 (s, 3H); 3.45 (m, 2H); 4.36 (m, 1H); 8.60 (s, 1H); 8.72 (br, 1H)


975
[DMSO] 1.75 (m, 2H); 3.20 (s, 3H); 3.38 (m, 4H); 8.51 (s, 1H); 8.81 (t, br, 1H); 13.6 (br)


1023
[DMSO] 8.22 (br, 1H); 8.35 (br, 1H); 8.61 (s, 1H); 13.8 (br, 1H)


1024
[DMSO] 2.82 (d, 3H); 8.50 (s, 1H); 8.75 (br, 1H); 13.7 (br, 1H)


1025
[DMSO] 1.13 (t, 3H); 3.35 (m, 2H); 8.52 (s, 1H); 8.75 (br, 1H); 13.5 (br, 1H)


1026
[DMSO] 0.90 (t, 3H); 1.53 (m, 2H); 3.25 (m, 2H); 8.52 (s, 1H); 8.75 (t, br, 1H); 13.5 (br, 1H)


1027
[DMSO] 1.18 (d, 6H); 4.08 (m, 1H); 8.54 (s, 1H); 8.56 (br, 1H)


1028
[DMSO] 0.58 (m, 2H); 0.75 (m, 2H); 3.86 (m, 1H); 8.48 (s, 1H); 8.75 (br, 1H)


1029
[DMSO] 0.89 (t, 3H); 1.34 (m, 2H); 1.50 (m, 2H); 3.26 (m, 2H); 8.51 (s, 1H); 8.81 (br, 1H);



13.6 (br, 1H)


1030
[DMSO] 1.70 (m, 2H); 2.04 (m, 2H); 2.25 (m, 2H); 4.39 (m, 1H); 8.53 (s, 1H); 8.91 (d, br,



1H); 13.4 (br, 1H)


1031
[CDCl3] 1.46 (s, 9H); 8.63 (s, 1H); 8.83 (br, 1H); 111.9 (br, 1H)


1032
[DMSO] 2.82 (s, br, 3H); 2.96 (s, br, 3H); 8.11 (s, 1H); 12.5 (br, 1H)


1037
[CDCl3] 1.23 (t, 6H); 3.42 (br, 4H); 7.88 (s, 1H)


1045
[DMSO] 0.25 (m, 2H); 0.46 (m, 2H); 1.04 (m, 1H); 3.20 (t, 2H); 8.55 (s, 1H); 8.82 (t, br, 1H);



13.6 (br, 1H)


1047
[DMSO] 0.90 (s, 9H); 3.13 (d, 2H); 8.48 (s, 1H); 8.61 (t, br, 1H)


1053
[DMSO] 0.90 (d, 6H); 1.82 (m, 1H); 3.13 (m, 2H); 8.50 (s, 1H); 8.75 (br, 1H); 13.5 (br, 1H)


1055
[DMSO] 0.89 (d, 6H); 1.41 (m, 2H); 1.61 (m, 1H); 3.31 (m, 2H); 8.49 (s, 1H); 8.90 (br, 1H);



13.5 (br, 1H)


1057
[DMSO] 3.95 (t, 2H); 5.18 (dd, 2H); 5.90 (m, 1H); 8.50 (s, 1H); 8.85 (t, br, 1H)


1061
[CDCl3] 1.80 (s, 3H); 4.03 (d, 2H); 4.93 (d, 2H); 8.76 (s, 1H); 9.22 (t, br, 1H);


1062
[DMSO] 3.18 (m, 1H); 4.10 (m, 2H); 8.48 (s, 1H); 9.00 (br, 1H)


1064
[DMSO] 0.88 (t, 3H); 1.16 (d, 3H); 1.51 (m, 2H); 3.93 (m, 1H); 8.50 (d, br, 1H); 8.55 (s, 1H);



13.6 (br, 1H)


1066
[DMSO] 0.86 (t, 3H); 1.15 (d, 3H); 1.30 (m, 2H); 1.48 (m, 2H); 4.00 (m, 1H); 8.50 (d, br,



1H); 8.52 (s, 1H); 13.6 (br, 1H)


1067
[CDCl3] 0.86 (t, 3H); 1.22 (d, 3H); 1.25 (m, 6H); 1.48 (m, 2H); 4.16 (m, 1H); 8.62 (s, 1H);



8.68 (br, 1H)


1070
[CDCl3] 0.93 (d, 6H); 1.23 (d, 3H); 1.27 (m, 1H); 1.50 (m, 1H); 1.70 (m, 1H); 4.25 (m, 1H);



8.63 (br, 2H)


1071
[CDCl3] 0.95 (s, 9H); 1.17 (d, 3H); 4.08 (m, 1H); 8.70 (s, 1H); 9.00 (d, br, 1H)


1072
[CDCl3] 0.95 (m, 6H); 1.20 (d, 3H); 1.82 (m, 1H); 4.07 (m, 1H); 8.76 (s, 1H); 9.13 (br, 1H)


1074
[CDCl3] 0.92 (t, 6H); 1.50 (m, 2H); 1.65 (m, 2H); 3.96 (m, 1H); 8.72 (s, 1H); 9.00 (d, br, 1H)


1077
[CDCl3] 3.42 (s, 6H); 3.62 (t, 2H); 4.50 (t, 1H); 8.62 (s, 1H); 8.90 (br, 1H)


1079
[CDCl3] 3.65 (m, 2H); 3.85 (m, 2H); 8.64 (s, 1H); 9.22 (br, 1H)


1080
[DMSO] 3.30 (s, 3H); 3.46 (m, 4H); 8.52 (s, 1H); 8.75 (br, 1H)


1087
[CDCl3] 1.29 (d, 3H); 3.39 (s, 3H); 3.45 (m, 2H); 4.37 (m, 1H); 8.66 (s, 1H); 8.98 (br, 1H);



12.50 (br, 1H)


1089
[DMSO] 1.75 (m, 2H); 3.23 (s, 3H); 3.38 (m, 4H); 8.52 (s, 1H); 8.80 (t, br, 1H)


1094
[CDCl3] 3.80 (s, 3H); 4.24 (d, 2H); 8.61 (s, 1H); 9.19 (br, 1H)


1138
[DMSO] 2.83 (d, 3H); 7.07 (t, 1H); 8.40 (s, 1H); 8.94 (br, 1H); 13.4 (br, 1H)


1139
[DMSO] 1.12 (t, 3H); 3.33 (m, 2H); 7.08 (t, 1H); 8.40 (s, 1H); 9.00 (br, 1H); 13.4 (br, 1H)


1171
[DMSO] 3.90 (t, 2H); 5.15 (dd, 2H); 5.90 (m, 1H); 7.10 (t, 1H); 8.40 (s, 1H); 9.16 (br, 1H);



13.4 (br, 1H)


1178
[CDCl3] 0.95 (t, 3H); 1.21 (d, 3H); 1.58 (m, 2H); 4.08 (m, 1H); 6.86 (t, 1H); 8.70 (s, 1H);



9.34 (d, br, 1H); 12.9 (br, 1H)


1180
[CDCl3] 0.93 (t, 3H); 1.21 (d, 3H); 1.40 (m, 2H); 1.52 (m, 2H); 4.16 (m, 1H); 6.87 (t, 1H);



8.70 (s, 1H); 9.31 (d, br, 1H); 12.9 (br, 1H)


1188
[CDCl3] 0.92 (t, 6H); 1.50 (m, 2H); 1.65 (m, 2H); 3.98 (m, 1H); 6.86 (t, 1H); 8.71 (s, 1H);



9.28 (d, br, 1H); 12.9 (br, 1H)


1201
[CDCl3] 1.27 (d, 3H); 3.40 (s, 3H); 3.43 (m, 2H); 4.37 (m, 1H); 6.85 (t, 1H); 8.68 (s, 1H);



9.42 (d, br, 1H); 12.7 (br, 1H)


1251
[DMSO] 8.26 (br, 1H), 8.42 (br, 1H); 8.62 (s, 1H)


1252
[CDCl3] 3.00 (d, 3H); 8.66 (s, 1H); 8.82 (br, 1H)


1253
[CDCl3] 1.24 (t, 3H); 3.50 (m, 2H); 8.68 (s, 1H); 8.86 (br, 1H)


1254
[CDCl3] 1.00 (t, 3H); 1.62 (m, 2H); 3.42 (m, 2H); 8.67 (s, 1H); 8.90 (br, 1H)


1255
[CDCl3] 1.25 (d, 6H); 4.25 (m, 1H); 8.70 (s, 1H); 8.84 (br, 1H)


1256
[CDCl3] 0.60 (m, 2H); 0.89. (m, 2H); 3.00 (m, 1H); 8.70 (s, 1H); 9.00 (br, 1H)


1257
[CDCl3] 0.96 (t, 3H); 1.42. (m, 2H); 1.60 (m, 2H); 3.45 (m, 2H); 8.70 (s, 1H); 8.88 (br, 1H);



12.1 (br, 1H)


1258
[CDCl3] 1.77 (m, 2H); 1.98. (m, 2H); 2.43 (m, 2H); 4.55 (m, 1H); 8.68 (s, 1H); 9.13 (br, 1H);



12.5 (br, 1H)


1259
[CDCl3] 1.45 (s, 9H); 8.67 (s, 1H); 8.78 (br, 1H); 12.4 (br, 1H)


1260
[CDCl3] 3.11 (s, 6H); 7.95 (s, 1H)


1265
[CDCl3] 1.25 (t, 6H); 3.45 (br, 4H); 7.89 (s, 1H)


1273
[CDCl3] 0.27 (m, 2H); 0.56. (m, 2H); 1.04 (m, 1H); 3.32 (m, 2H); 8.67 (s, 1H); 8.92 (br, 1H);



12.3 (br, 1H)


1275
[CDCl3] 0.97 (s, 9H); 3.29 (d, 2H); 8.73 (s, 1H); 9.00 (br, 1H); 11.9 (br, 1H)


1281
[CDCl3] 0.98 (d, 6H); 1.89 (m, 1H); 3.29 (t, 2H); 8.70 (s, 1H); 8.98 (br, 1H); 12.1 (br, 1H)


1283
[CDCl3] 0.95 (d, 6H); 1.50 (m, 2H); 1.68 (m 1H); 3.46 (m, 2H); 8.69 (s, 1H); 8.83 (br, 1H);



12.1 (br, 1H)


1285
[CDCl3] 4.09 (t, 2H); 5.22 (dd, 2H); 5.91 (m, 1H); 8.70 (s, 1H); 9.01 (br, 1H); 12.2 (br, 1H)


1289
[DMSO] 0.26 (m, 2H); 0.47 (m, 2H); 1.05 (m, 1H); 3.20 (m, 2H); 6.85 (tt, 1H); 7.25 (br, 1H);



8.45 (d, 1H); 9.15 (br, 1H), 13.4 (br, 1H)


1290
[CDCl3] 2.25 (m, 1H); 4.23 (m, 2H); 8.72 (s, 1H); 9.20 (br, 1H), 12.0 (br, 1H)


1292
[CDCl3] 0.95 (t, 3H); 1.21 (d, 3H); 1.55 (m 2H); 4.10 (m, 1H); 8.70 (s, 1H); 8.82 (br, 1H)


1294
[CDCl3] 0.93 (t, 3H); 1.22 (d, 3H); 1.38 (m, 2H); 1.52 (m, 2H); 4.18 (m, 1H); 8.70 (s, 1H);



8.79 (br, 1H); 12.4 (br, 1H)


1295
[CDCl3] 0.89 (t, 3H); 1.20 (d, 3H); 1.25-1.4 (m, 6H); 1.50 (m, 2H); 4.16 (m, 1H); 8.70 (s,



1H); 8.75 (br, 1H)


1298
[CDCl3] 0.92 (t, 6H); 1.40 (d, 3H); 1.32 (m, 1H); 1.45 (m, 1H); 1.55 (m, 1H); 4.25 (m, 1H);



8.70 (s, 1H); 8.75 (br, 1H); 12.4 (br, 1H)


1299
[CDCl3] 0.95 (s, 9H); 1.15 (d, 3H); 4.10 (m, 1H); 8.72 (s, 1H); 8.88 (br, 1H); 11.9 (br, 1H)


1300
[CDCl3] 0.95 (m, 6H); 1.15 (d, 3H); 1.77 (m, 1H); 4.05 (m, 1H); 8.71 (s, 1H); 8.85 (br, 1H)


1302
[CDCl3] 0.93 (t, 6H); 1.48 (m, 2H); 1.65 (m, 2H); 3.99 (m, 1H); 8.71 (s, 1H); 8.76 (br, 1H);



12.4 (br, 1H)


1305
[CDCl3] 3.40 (s, 6H); 3.62 (t, 2H); 4.50 (t, 1H); 8.60 (s, 1H); 8.74 (br, 1H); 11.7 (br, 1H)


1307
[CDCl3] 3.65 (m, 2H); 3.87 (m, 2H); 4.50 (t, 1H); 8.66 (s, 1H); 9.11 (br, 1H)


1308
[CDCl3] 3.40 (s, 3H); 3.58 (m, 2H); 3.67 (m, 2H); 8.60 (s, 1H); 8.75 (br, 1H); 11.7 (br, 1H)


1315
[CDCl3] 1.48 (d, 3H); 3.38 (s, 3H); 3.44 (m, 2H); 4.38 (m, 1H); 8.62 (s, 1H); 8.72 (br, 1H);



12.1 (br, 1H)


1317
[CDCl3] 1.90 (m, 2H); 3.40 (s, 3H); 3.58 (m, 4H); 8.39 (s, 1H); 8.62 (br, 1H)


1322
[CDCl3] 3.79 (s, 3H); 4.25 (d, 2H); 8.65 (s, 1H); 9.18 (br, 1H)


1365
[DMSO] 8.24 (br, 1H), 8.42 (br, 1H); 8.81 (s, 1H); 13.6 (br, 1H)


1366
[DMSO] 8.19 (br, 1H), 8.34 (br, 1H); 8.78 (s, 1H); 13.7 (br, 1H)


1368
[DMSO] 2.83 (d, 3H); 6.81 (tt, 1H); 7.22 (br, 1H); 8.41 (d, 1H); 9.00 (br, 1H); 13.4 (br, 1H)


1369
[DMSO] 1.12 (t, 3H); 3.35 (m, 2H); 6.85 (tt, 1H); 7.20 (br, 1H); 8.41 (d, 1H); 9.20 (br, 1H);



13.4 (br, 1H)


1370
[DMSO] 0.89 (t, 3H); 1.52 (m, 2H); 3.27 (q, 2H); 6.82 (tt, 1H); 7.20 (br, 1H); 8.40 (d, 1H);



9.20 (br, 1H); 13.4 (br, 1H)


1371
[DMSO] 1.18 (d, 6H); 4.09 (m, 1H); 6.82 (tt, 1H); 7.20 (br, 1H); 8.42 (d, 1H); 8.95 (br, 1H);



13.4 (br, 1H)


1372
[DMSO] 0.56 (m, 2H); 0.75 (m, 2H); 2.85 (m, 1H); 6.83 (tt, 1H); 7.21 (br, 1H); 8.40 (d, 1H);



9.05 (br, 1H); 13.4 (br, 1H)


1373
[DMSO] 0.89 (t, 3H); 1.32 (m, 2H); 1.50 (m, 2H); 3.30 (q, 2H); 6.84 (tt, 1H); 7.20 (br, 1H);



8.41 (d, 1H); 9.10 (br, 1H); 13.4 (br, 1H)


1389
[DMSO] 0.26 (m, 2H); 0.47 (m, 2H); 1.05 (m, 1H); 3.20 (m, 2H); 6.85 (tt, 1H); 7.25 (br, 1H);



8.45 (d, 1H); 9.15 (br, 1H), 13.4 (br, 1H)


1391
[DMSO] 0.91 (s, 9H); 3.16 (d, 2H); 6.82 (tt, 1H); 7.10 (br, 1H); 8.41 (d, 1H); 9.20 (br, 1H);



13.3 (br, 1H)


1397
[DMSO] 0.90 (d, 6H); 1.82 (m, 1H); 3.15 (m, 2H); 6.82 (tt, 1H); 7.20 (br, 1H); 8.40 (d, 1H);



9.15 (br, 1H), 13.4 (br, 1H)


1401
[DMSO] 3.95 (m, 2H); 5.18 (dd, 2H); 5.92 (m, 1H); 6.82 (tt, 1H); 7.20 (d, 1H); 8.42 (d, 1H);



9.20 (br, 1H); 13.3 (br, 1H)


1406
[DMSO] 3.15 (t, 1H); 4.13 (m, 2H); 6.82 (tt, 1H); 7.18 (br, 1H); 8.41 (d, 1H); 9.35 (br, 1H);



13.3 (br, 1H)


1408
[DMSO] 0.87 (t, 3H); 1.14 (d, 3H); 1.51 (m, 2H); 3.92 (m, 1H); 6.82 (tt, 1H); 7.20 (br, 1H);



8.41 (d, 1H); 8.90 (br, 1H), 13.4 (br, 1H)


1410
[DMSO] 0.86 (t, 3H); 1.15 (d, 3H); 1.30 (m, 2H); 1.48 (m, 2H); 4.02 (m, 1H); 6.83 (tt, 1H);



7.20 (br, 1H); 8.42 (d, 1H); 8.90 (br, 1H), 13.4 (br, 1H)


1411
[DMSO] 0.88 (t, 3H); 1.15 (d, 3H); 1.27 (m, 6H); 1.49 (m, 2H); 4.00 (m, 1H); 6.82 (tt, 1H);



7.20 (br, 1H); 8.42 (d, 1H); 8.92 (br, 1H), 13.4 (br, 1H)


1414
[DMSO] 0.88 (d, 6H); 1.15 (d, 3H); 1.28 (m, 1H); 1.46 (m, 1H); 1.60 (m, 1H); 4.10 (m, 1H);



6.81 (tt, 1H); 7.20 (br, 1H); 8.42 (d, 1H); 8.90 (br, 1H), 13.4 (br, 1H)


1418
[CDCl3] 0.93 (t, 6H); 1.50 (m, 2H); 1.65 (m, 2H); 4.00 (m, 1H); 6.83 (d, 1H); 8.69 (d, 1H);



9.21 (d, br, 1H); 13.0 (br, 1H)


1421
[CDCl3] 3.41 (s, 6H); 3.52 (t, 2H); 4.50 (t, 1H); 6.12 (tt, 1H); 6.81 (d, 1H); 8.64 (d, 1H);



9.41 (br, 1H); 12.5 (br, 1H)


1424
[CDCl3] 3.37 (s, 3H); 3.56 (m, 2H); 3.67 (m, 2H); 6.11 (tt, 1H); 6.84 (d, 1H); 8.65 (d, 1H);



9.46 (br, 1H), 12.2 (br, 1H)


1431
[CDCl3] 1.28 (d, 3H); 3.39 (s, 3H); 3.45 (m, 2H); 4.40 (m, 1H); 6.10 (tt, 1H); 6.83 (d, 1H);



8.67 (d, 1H); 9.39 (d, br, 1H); 13.0 (br, 1H)


1433
[DMSO] 1.75 (m, 2H); 3.24 (s, 3H); 3.38 (m, 4H); 6.83 (tt, 1H); 7.20 (br, 1H); 8.42 (d, 1H);



9.15 (br, 1H), 13.4 (br, 1H)


1481
[DMSO] 7.42 (br, 1H); 8.10 (br, 1H); 8.40 (br, 1H); 8.46 (d, 1H), 13.6 (br, 1H)


1482
[CDCl3] 3.01 (d, 3H); 6.88 (d, 1H); 8.67 (d, 1H); 9.34 (br, 1H); 12.5 (br, 1H)


1483
[CDCl3] 1.27 (t, 3H); 3.50 (m, 2H); 6.88 (d, 1H); 8.68 (d, 1H); 9.32 (br, 1H); 12.6 (br, 1H)


1484
[CDCl3] 1.00 (t, 3H); 1.63 (m, 2H); 3.41 (m, 2H); 6.88 (d, 1H); 8.70 (d, 1H); 9.38 (br, 1H);



12.9 (br, 1H)


1485
[CDCl3] 1.25 (d, 6H); 4.27 (m, 1H); 6.88 (d, 1H); 8.70 (d, 1H); 9.30 (d, br, 1H); 13.4 (br, 1H)


1486
[CDCl3] 0.62 (m, 2H); 0.86 (m, 2H); 3.01 (m, 1H); 6.88 (d, 1H); 8.70 (d, 1H); 9.41 (br, 1H);



12.6 (br, 1H)


1487
[CDCl3] 0.95 (t, 3H); 1.44 (m, 2H); 1.61 (m, 2H); 3.45 (m, 2H); 6.88 (d, 1H); 8.70 (d, 1H);



9.35 (t, br, 1H); 12.7 (br, 1H)


1488
[CDCl3] 1.78 (m, 2H); 2.00 (m, 2H); 2.42 (m, 2H); 4.58 (m, 1H); 6.88 (d, 1H); 8.68 (d, 1H);



9.60 (d, br, 1H); 13.3 (br, 1H)


1503
[CDCl3] 0.26 (m, 2H); 0.55 (m, 2H); 1.06 (m, 1H); 3.33 (m, 2H); 6.88 (d, 1H); 8.70 (d, 1H);



9.45 (br, 1H); 12.9 (br, 1H)


1505
[CDCl3] 0.98 (s, 9H); 3.30 (d, 2H); 6.88 (d, 1H); 8.72 (d, 1H); 9.43 (t, br, 1H); 12.5 (br, 1H)


1511
[CDCl3] 0.98 (d, 6H); 1.90 (m, 1H); 3.30 (m, 2H); 6.88 (d, 1H); 8.70 (d, 1H); 9.42 (t, br, 1H)


1513
[CDCl3] 0.85 (d, 6H); 1.51 (m, 2H); 1.70 (m, 1H); 3.47 (m, 2H); 6.88 (d, 1H); 8.70 (d, 1H);



9.32 (t, br, 1H); 12.7 (br, 1H)


1515
[CDCl3] 4.10 (t, 2H); 5.25 (dd, 2H); 5.91 (m, 1H); 6.88 (d, 1H); 8.70 (d, 1H); 9.47 (br, 1H);



12.8 (br, 1H)


1519
[DMSO] 1.71 (s, 3H); 3.88 (d, 2H); 4.84 (d, 2H); 7.35 (br, 1H); 8.41 (d, 1H); 9.02 (br, 1H);



13.4 (br, 1H)


1520
[DMSO] 3.15 (m, 1H); 4.12 (m, 2H); 7.36 (d, br, 1H); 8.42 (d, 1H); 9.15 (br, 1H), 13.4 (br,



1H)


1522
[CDCl3] 0.95 (t, 3H); 1.22 (d, 3H); 1.59 (m, 2H); 4.11 (m, 1H); 6.88 (d, 1H); 8.71 (d, 1H);



9.28 (d, br, 1H); 13.4 (br, 1H)


1524
[CDCl3] 0.92 (t, 3H); 1.23 (d, 3H); 1.40 (m, 2H); 1.52 (m, 2H); 4.20 (m, 1H); 6.89 (d, 1H);



8.71 (d, 1H); 9.27 (d, br, 1H); 13.4 (br, 1H)


1525
[CDCl3] 0.88 (t, 3H); 1.23 (d, 3H); 1.25-1.4 (m, 6H); 1.55 (m, 2H); 4.18 (m, 1H); 7.89 (d,



1H); 8.70 (d, 1H); 9.28 (br, 1H); 13.2 (br, 1H)


1528
[CDCl3] 0.92 (d, 6H); 1.22 (d, 3H), 1.35 (m, 1H); 1.50 (m, 1H); 1.68 (m, 1H); 4.28 (m, 1H);



6.89 (d, 1H); 8.71 (d, 1H); 9.26 (d, br, 1H); 13.3 (br, 1H)


1529
[CDCl3] 0.95 (s, 9H); 1.17 (d, 3H); 4.12 (m, 1H); 6.89 (d, 1H); 8.73 (d, 1H); 9.30 (d, br, 1H),



12.8 (br, 1H)


1530
[CDCl3] 0.95 (dt, 6H); 1.17 (d, 3H); 1.82 (m, 1H); 4.08 (m, 1H); 6.89 (d, 1H); 8.72 (d, 1H);



9.31 (d, br, 1H); 13.2 (br, 1H)


1532
[CDCl3] 0.95 (t, 6H); 1.50 (m, 2H); 1.66 (m, 2H); 4.00 (m, 1H); 6.89 (d, 1H); 8.72 (d, 1H);



9.21 (d, br, 1H); 13.3 (br, 1H)


1535
[DMSO] 3.32 (s, 6H); 3.45 (t, 2H); 4.50 (t, 1H); 7.33 (d, br, 1H); 8.43 (d, 1H); 8.92 (br, 1H);



13.4 (br, 1H)


1537
[DMSO] 3.38 (m, 2H); 3.52 (m, 2H); 4.80 (br, 1H); 7.37 (br, 1H); 8.45 (d, 1H); 8.96 (br, 1H);



13.4 (br, 1H)


1538
[DMSO] 3.25 (s, 3H); 3.49 (m, 4H); 7.37 (d, br, 1H); 8.44 (d, 1H); 8.97 (br, 1H); 13.5 (br, 1H)


1545
[DMSO] 1.15 (d, 3H); 3.27 (s, 3H); 3.40 (m, 2H); 4.19 (m, 1H); 7.35 (d, br, 1H); 8.43 (d, 1H);



8.82 (br, 1H); 13.4 (br, 1H)


1547
[DMSO] 1.75 (m, 2H); 3.25 (s, 3H); 3.40 (m, 4H); 7.38 (br, 1H); 8.40 (d, 1H); 8.94 (br, 1H);



13.4 (br, 1H)


1595
[DMSO] 7.45 (d, 1H); 8.15 (br, 1H); 8.40 (br, 1H); 8.50 (d, 1H); 13.7 (br, 1H)


1596
[DMSO] 2.82 (d, 3H); 7.42 (d, 1H); 8.41 (d, 1H); 8.80 (br, 1H); 13.4 (br, 1H)


1597
[DMSO] 1.12 (t, 3H); 3.31 (m, 2H); 7.41 (d, 1H); 8.41 (d, 1H); 8.85 (br, 1H); 13.45 (br, 1H)


1598
[DMSO] 0.90 (t, 3H); 1.54 (m, 2H); 3.25 (q, 2H); 7.41 (d, 1H); 8.40 (d, 1H); 8.85 (br, 1H);



13.45 (br)


1599
[DMSO] 1.17 (d, 6H); 4.10 (m, 1H); 7.40 (d, 1H); 8.41 (d, 1H); 8.67 (d, br, 1H); 13.4 (br, 1H)


1600
[DMSO] 0.57 (m, 2H); 0.75 (m, 2H); 2.86 (m, 1H); 7.41 (d, 1H); 8.37 (d, 1H); 8.80 (br, 1H);



13.35 (br, 1H)


1601
[CDCl3] 0.95 (t, 3H); 1.40 (m, 2H); 1.60 (m, 2H); 3.45 (q, 2H); 6.88 (d, 1H); 8.71 (d, 1H);



9.28 (br, 1H); 12.9 (br, 1H)


1602
[CDCl3] 1.78 (m, 2H); 1.95 (m, 2H); 2.40 (m, 2H); 4.57 (m, 1H); 6.86 (d, 1H); 8.70 (d, 1H);



9.45 (d, br, 1H); 12.9 (br, 1H)


1603
[CDCl3] 1.45 (s, 9H); 6.85 (d, 1H); 8.67 (d, 1H); 9.15 (br, 1H); 12.6 (br, 1H)


1604
[CDCl3] 3.05 (s, 6H); 7.07 (d, 1H); 7.80 (d, 1H)


1609
[CDCl3] 1.22 (t, 6H); 3.40 (m, 4H); 7.02 (d, 1H); 7.72 (d, 1H)


1617
[DMSO] 0.25 (m, 2H), 0.46 (m, 2H); 1.05 (m, 1H); 3.22 (m, 2H); 7.45 (d, br, 1H); 8.45 (d,



1H); 8.95 (br, 1H); 13.4 (br, 1H)


1619
[DMSO] 0.90 (s, 9H), 3.15 (d, 2H); 7.38 (d, br, 1H); 8.40 (d, 1H); 8.80 (br, 1H); 13.4 (br, 1H)


1625
[DMSO] 0.90 (d, 6H); 1.82 (m, 1H); 3.14 (t, 2H); 7.39 (d, 1H); 8.40 (d, 1H); 8.91 (t, br, 1H)


1627
[CDCl3] 0.92 (d, 6H); 1.49 (m, 2H); 1.68 (m, 1H); 3.46 (m, 2H); 6.87 (d, 1H); 8.70 (d, 1H);



9.22 (br, 1H); 12.8 (br, 1H)


1629
[DMSO] 3.95 (m, 2H); 5.15 (dd, 2H); 5.90 (m, 1H); 7.40 (d, 1H); 8.40 (d, 1H); 8.95 (br, 1H);



13.4 (br, 1H)


1633
[CDCl3] 1.78 (s, 3H); 4.02 (d, 2H); 4.88 (d, 2H); 6.87 (d 1H); 8.72 (d, 1H); 9.42 (br, 1H);



12.7 (br, 1H)


1634
[CDCl3] 2.23 (m, 1H); 4.23 (m, 2H); 6.88 (d, 1H); 8.73 (d, 1H); 9.51 (br, 1H), 12.8 (br, 1H)


1636
[DMSO] 0.89 (t, 3H); 1.14 (d, 3H); 1.51 (m, 2H); 3.95 (m, 1H); 7.41 (d, 1H); 8.40 (d, 1H);



8.60 (br, 1H); 13.6 (br, 1H)


1638
[DMSO] 0.87 (t, 3H); 1.15 (d, 3H); 1.32 (m, 2H); 1.46 (m, 2H); 4.03 (m, 1H); 7.40 (d, 1H);



8.40 (d, 1H); 8.51 (br, 1H); 13.4 (br, 1H)


1639
[CDCl3] 0.88 (t, 3H); 1.21 (d, 3H); 1.32 (m, 6H); 1.50 (m, 2H); 4.18 (m, 1H); 6.88 (d, 1H);



8.71 (d, 1H); 9.12 (d, br, 1H), 12.9 (br, 1H)


1642
[CDCl3] 0.92 (t, 6H); 1.20 (d, 3H); 1.32 (m, 1H); 1.46 (m, 1H); 1.67 (m, 1H); 4.27 (m, 1H);



6.88 (d, 1H); 8.71 (d, 1H); 9.12 (d, br, 1H), 12.9 (br, 1H)


1643
[CDCl3] 0.93 (s, 9H); 1.15 (d, 3H); 4.12 (m, 1H); 6.88 (d, 1H); 8.72 (d, 1H); 9.22 (d, br, 1H)


1644
[CDCl3] 0.95 (m, 6H); 1.15 (d, 3H); 1.78 (m, 1H); 4.05 (m, 1H); 6.88 (d, 1H); 8.72 (d, 1H);



9.18 (d, br, 1H); 12.7 (br, 1H)


1646
[DMSO] 0.87 (t, 6H); 1.45 (m, 2H); 1.55 (m, 2H); 3.81 (m, 1H); 7.40 (d, 1H); 8.40 (d, 1H);



8.52 (d, br, 1H); 13.4 (br, 1H)


1649
[CDCl3] 3.40 (s, 6H); 3.61 (t, 2H); 4.50 (t, 1H); 6.87 (d, 1H); 8.69 (d, 1H); 9.32 (br, 1H);



12.3 (br, 1H)


1651
[CDCl3] 3.63 (m, 2H); 3.84 (m, 2H); 6.88 (d, 1H); 8.68 (d, 1H); 9.60 (br, 1H)


1652
[DMSO] 3.25 (s, 3H); 3.50 (m, 4H); 7.40 (d, br, 1H); 8.45 (d, 1H); 8.92 (br, 1H); 13.5 (br, 1H)


1659
[DMSO] 1.15 (d, 3H); 3.25 (s, 3H); 3.38 (m, 2H); 4.17 (m, 1H); 7.40 (d, br, 1H); 8.43 (d, 1H);



8.75 (br, 1H); 13.5 (br, 1H)


1661
[DMSO] 1.74 (m, 2H); 3.22 (s, 3H); 3.37 (m, 4H); 7.42 (d, br, 1H); 8.42 (d, 1H); 8.90 (br,



1H); 13.4 (br, 1H)


1666
[CDCl3] 3.77 (s, 3H); 4.23 (d, 2H); 6.87 (d, 1H); 8.67 (d, 1H); 9.65 (br, 1H); 12.1 (br, 1H)


1711
[DMSO] 2.83 (d, 3H); 8.39 (s, 1H); 8.72 (d, br, 1H); 13.5 (br)


1712
[DMSO] 1.11 (t, 3H); 3.30 (m, 2H); 8.40 (s, 1H); 8.75 (t, br, 1H)


1713
[CDCl3] 0.99 (t, 3H); 1.62 (m, 2H); 3.41 (q, 2H); 8.56 (s, 1H); 9.00 (br, 1H)


1714
[CDCl3] 1.24 (d, 6H); 4.22 (m, 1H); 8.41 (s, 1H); 9.17 (br, 1H)


1715
[CDCl3] 0.61 (m, 2H); 0.90 (m, 2H); 2.95 (m, 1H); 8.57 (s, 1H); 9.02 (br, 1H)


1716
[CDCl3] 0.94 (t, 3H); 1.41 (m, 2H); 1.58 (m, 2H); 3.45 (m, 2H); 8.54 (s, 1H); 9.05 (br, 1H)


1717
[CDCl3] 1.80 (m, 2H); 1.98 (m, 2H); 2.42 (m, 2H); 4.55 (m, 1H); 8.55 (s, 1H); 9.01 (br, 1H);



12.0 (br, 1H)


1719
[DMSO] 2.83 (s, 3H); 2.97 (s, 3H); 8.04 (s, 1H); 12.6 (br, 1H)


1720
[DMSO] 1.03 (t, 3H); 1.15 (t, 3H); 3.12 (q, 2H); 3.45 (q, 2H); 8.05 (s, 1H); 12.5 (br, 1H)


1721
[CDCl3] 0.25 (m, 2H); 0.55 (m, 2H); 1.05 (m, 1H); 3.32 (m, 2H); 8.57 (s, 1H); 8.93 (br, 1H);



12.1 (br, 1H)


1722
[CDCl3] 0.96 (s, 9H); 3.28 (d, 2H); 8.59 (s, 1H); 9.05 (br, 1H)


1723
[CDCl3] 0.95 (d, 6H); 1.90 (m, 1H); 3.29 (t, 2H); 8.59 (s, 1H); 9.00 (br, 1H); 12.0 (br, 1H)


1725
[CDCl3] 0.94 (d, 6H); 1.49 (q, 2H); 1.65 (m, 1H); 3.45 (m, 2H); 8.59 (s, 1H); 8.93 (br, 1H);



12.1 (br, 1H)


1727
[CDCl3] 4.08 (m, 2H); 5.21 (dd, 2H); 5.90 (m, 1H); 8.60 (s, 1H); 9.05 (br, 1H); 12.1 (br, 1H)


1728
[CDCl3] 1.78 (s, 3H); 4.01 (d, 2H); 4.90 (d, 2H); 8.61 (s, 1H); 9.09 (bt, 1H); 11.9 (br, 1H)


1729
[CDCl3] 2.25 (m, 1H); 4.23 (m, 2H); 8.63 (s, 1H); 9.23 (br, 1H); 11.9 (br, 1H)


1731
[CDCl3] 0.95 (t, 3H); 1.23 (d, 3H); 1.58 (m, 2H); 4.11 (m, 1H); 8.55 (s, 1H); 8.60 (br, 1H)


1733
[CDCl3] 0.92 (t, 3H); 1.23 (d, 3H); 1.39 (m, 2H); 1.52 (m, 2H); 4.20 (m, 1H); 8.55 (s, 1H);



8.66 (br, 1H)


1734
[CDCl3] 0.87 (t, 3H); 1.22 (d, 3H); 1.35 (m, 6H); 1.52 (m, 2H); 4.17 (m, 1H); 8.52 (s, 1H);



8.61 (br, 1H)


1735
[CDCl3] 0.94 (m, 6H); 1.23 (d, 3H); 1.33 (m, 1H); 1.45 (m, 1H); 1.65 (m, 1H); 4.27 (m, 1H);



8.56 (s, 1H); 8.63 (br, 1H); 11.9 (br)


1736
[CDCl3] 0.96 (s, 9H); 1.17 (d, 3H); 4.08 (m, 1H); 8.57 (s, 1H); 8.80 (d, br, 1H)


1737
[CDCl3] 0.95 (m, 6H); 1.18 (d, 3H); 1.80 (m, 1H); 4.05 (m, 1H); 8.57 (s, 1H); 8.73 (d, br, 1H)


1738
[DMSO] 0.87 (t, 6H), 1.45 (m, 2H), 1.55 (m, 2H); 3.80 (m, 1H); 8.40 (s, 1H); 8.42 (d, br, 1H);



13.4 (br, 1H)


1739
[CDCl3] 3.42 (s, 6H); 3.63 (t, 2H); 4.50 (t, 1H); 8.49 (s, 1H); 8.74 (br, 1H); 11.4 (br, 1H)


1741
[CDCl3] 3.65 (m, 2H); 3.85 (m, 2H); 8.55 (s, 1H); 9.16 (br, 1H)


1742
[CDCl3] 3.40 (s, 3H); 3.57 (m, 2H); 3.67 (m, 2H); 8.47 (s, 1H); 8.75 (br, 1H); 11.5 (br, 1H)


1744
[CDCl3] 1.27 (d, 3H); 3.39 (s, 3H); 3.45 (m, 2H); 4.37 (m, 1H); 8.45 (s, 1H); 8.57 (br, 1H);



11.6 (br, 1H)


1745
[CDCl3] 1.90 (m, 2H); 3.40 (s, 3H); 3.56 (m, 4H); 8.27 (s, 1H); 8.65 (br, 1H); 11.8 (br, 1H)


1746
[DMSO] 3.67 (s, 3H); 4.13 (d, 2H); 8.38 (s, 1H); 9.12 (br, 1H); 13.6 (br, 1H)


1751
[DMSO] 8.24 (br, 1H); 8.38 (br, 1H); 8.61 (br, 1H); 13.7 (br, 1H)


1752
[CDCl3] 3.00 (d, 3H); 8.71 (s, 1H); 8.91 (br, 1H); 12.2 (br, 1H)


1753
[CDCl3] 1.23 (t, 3H); 3.49 (m, 2H); 8.71 (s, 1H); 8.89 (br, 1H); 12.1 (br, 1H)


1754
[CDCl3] 0.98 (t, 3H); 1.62 (m, 2H); 3.40 (q, 2H); 8.70 (s, 1H); 8.90 (br, 1H)


1755
[CDCl3] 1.25 (d, 6H); 4.25 (m, 1H); 8.68 (br, 2H); 12.0 (br, 1H)


1756
[CDCl3] 0.61 (m, 2H); 0.89 (m, 2H); 2.95 (m, 1H); 8.70 (s, 1H); 8.97 (br, 1H)


1757
[CDCl3] 0.94 (t, 3H); 1.40 (m, 2H); 1.58 (m, 2H); 3.45 (m, 2H); 8.69 (s, 1H); 8.88 (br, 1H);



12.0 (br, 1H)


1758
[CDCl3] 1.80 (m, 2H); 1.98 (m, 2H); 2.41 (m, 2H); 4.55 (m, 1H); 8.67 (s, 1H); 8.98 (br, 1H);



12.1 (br, 1H)


1759
[CDCl3] 1.32 (s, 9H); 8.50 (br, 1H); 8.60 (s, 1H)


1760
[CDCl3] 3.12 (s, 6H); 7.99 (s, 1H)


1761
[CDCl3] 1.24 (t, 6H); 3.43 (m, 4H); 7.89 (s, 1H)


1762
[CDCl3] 0.28 (m, 2H); 0.55 (m, 2H); 1.03 (m, 1H); 3.31 (m, 2H); 8.67 (s, 1H); 8.85 (br, 1H);



11.9 (br, 1H)


1763
[CDCl3] 0.96 (s, 9H); 3.27 (d, 2H); 8.71 (s, 1H); 9.00 (br, 1H)


1764
[CDCl3] 0.95 (d, 6H); 1.89 (m, 1H); 3.28 (t, 2H); 8.70 (s, 1H); 8.97 (br, 1H)


1766
[CDCl3] 0.95 (d, 6H); 1.48 (q, 2H); 1.65 (m, 1H); 3.45 (m, 2H); 8.69 (s, 1H); 8.85 (br, 1H);



12.0 (br, 1H)


1768
[CDCl3] 4.08 (m, 2H); 5.21 (dd, 2H); 5.89 (m, 1H); 8.71 (s, 1H); 9.02 (br, 1H); 12.1 (br, 1H)


1769
[CDCl3] 1.77 (s, 3H); 4.01 (d, 2H); 4.87 (d, 2H); 8.71 (s, 1H); 9.03 (br, 1H)


1770
[CDCl3] 2.23 (m, 1H); 4.23 (m, 2H); 8.72 (s, 1H); 9.20 (br, 1H); 12.0 (br, 1H)


1772
[CDCl3] 0.95 (t, 3H); 1.21 (d, 3H); 1.55 (m, 2H); 4.10 (m, 1H); 8.67 (br, 1H); 8.70 (s, 1H);



12.1 (br, 1H)


1774
[CDCl3] 0.91 (t, 3H); 1.21 (d, 3H); 1.38 (m, 2H); 1.50 (m, 2H); 4.19 (m, 1H); 8.64 (br, 1H);



8.69 (s, 1H); 12.0 (br, 1H)


1775
[CDCl3] 0.89 (t, 3H); 1.21 (d, 3H); 1.33 (m, 6H); 1.51 (m, 2H); 4.17 (m, 1H); 8.60 (br, 1H);



8.68 (s, 1H)


1776
[CDCl3] 0.90 (m, 6H); 1.21 (d, 3H); 1.31 (m, 1H); 1.45 (m, 1H); 1.64 (m, 1H); 4.25 (m, 1H);



8.60 (br, 1H); 8.69 (s, 1H)


1777
[CDCl3] 0.94 (s, 9H); 1.15 (d, 3H); 4.08 (m, 1H); 8.69 (s, 1H); 8.79 (br, 1H)


1778
[CDCl3] 0.93 (m, 6H); 1.17 (d, 3H); 1.79 (m, 1H); 4.05 (m, 1H); 8.67 (s, 1H); 8.71 (br, 1H)


1780
[CDCl3] 0.92 (t, 6H); 1.48 (m, 2H); 1.62 (m, 2H); 3.96 (m, 1H); 8.61 (s, 1H); 9.16 (d, br, 1H)


1781
[CDCl3] 3.40 (s, 6H); 3.61 (t, 2H); 4.50 (t, 1H); 8.63 (s, 1H); 8.76 (br, 1H)


1783
[CDCl3] 3.64 (m, 2H); 3.86 (m, 2H); 8.68 (s, 1H); 9.17 (br, 1H)


1784
[CDCl3] 3.49 (s, 3H); 3.55 (m, 2H); 3.66 (m, 2H); 8.62 (s, 1H); 8.77 (br, 1H)


1785
[CDCl3] 1.27 (d, 3H); 3.39 (s, 3H); 3.44 (m, 2H); 4.37 (m, 1H); 8.56 (br, 1H); 8.60 (s, 1H);



11.9 (br, 1H)


1786
[CDCl3] 1.90 (m, 2H); 3.40 (s, 3H); 3.58 (m, 4H); 8.40 (s, 1H); 8.65 (br, 1H)


1787
[CDCl3] 3.78 (s, 3H); 4.24 (d, 2H); 8.69 (s, 1H); 9.25 (br, 1H); 11.5 (br, 1H)


1792
[DMSO] 8.22 (br, 1H); 8.37 (br, 1H); 8.81 (br, 1H); 13.7 (br, 1H)


1793
[CDCl3] 3.00 (d, 3H); 8.80 (s, br, 2H); 12.0 (br, 1H)


1794
[CDCl3] 1.24 (t, 3H); 3.49 (m, 2H); 8.40 (s, br, 2H); 12.0 (br, 1H)


1795
[DMSO] 0.89 (t, 3H); 1.53 (m, 2H); 3.26 (q, 2H); 8.72 (s, 1H); 8.78 (t, br, 1H); 13.4 (br, 1H)


1796
[DMSO] 1.18 (d, 6H); 4.08 (m, 1H); 8.60 (d, br, 2H); 13.4 (br, 1H)


1797
[DMSO] 0.60 (m, 2H); 0.75 (m, 2H); 2.88 (m, 1H); 8.68 (s, 1H); 8.77 (d, br, 1H); 13.3 (br,



1H)


1798
[CDCl3] 0.94 (t, 3H); 1.40 (m, 2H); 1.59 (m, 2H); 3.44 (m, 2H); 8.79 (s, br, 2H)


1799
[DMSO] 1.70 (m, 2H); 2.05 (m, 2H); 2.27 (m, 2H); 4.39 (m, 1H); 8.71 (s, 1H); 8.95 (d, br,



1H); 13.4 (br, 1H)


1800
[CDCl3] 1.43 (s, 9H); 8.70 (br, 1H); 8.85 (s, 1H); 11.5 (br)


1801
[CDCl3] 3.10 (s, 6H); 8.20 (s, 1H)


1802
[CDCl3] 1.23 (t, 6H); 3.43 (m, br, 4H); 8.12 (s, 1H)


1803
[DMSO] 0.26 (m, 2H); 0.50 (m, 2H); 1.05 (m, 1H); 3.19 (t, 2H); 8.76 (s, 1H); 8.87 (br, 1H);



13.5 (br, 1H)


1804
[DMSO] 0.91 (s, 9H); 3.13 (d, 2H); 8.61 (t, br, 1H); 8.68 (s, 1H); 13.4 (br, 1H)


1805
[DMSO] 0.89 (d, 6H); 1.84 (m, 1H); 3.14 (t, 2H); 8.70 (s, 1H); 8.75 (t, br, 1H); 13.4 (br, 1H)


1807
[DMSO] 0.89 (d, 6H); 1.40 (q, 2H); 1.62 (m, 1H); 3.30 (m, 2H); 8.71 (s, 1H); 8.73 (t, br, 1H);



13.4 (br, 1H)


1809
[DMSO] 3.93 (m, 2H); 5.18 (dd, 2H); 5.90 (m, 1H); 8.71 (s, 1H); 8.89 (t, br, 1H); 13.4 (br,



1H)


1810
[DMSO] 1.72 (s, 3H); 3.87 (d, 2H); 4.85 (d, 2H); 8.71 (s, 1H); 8.87 (t, br, 1H); 13.3 (br, 1H)


1811
[DMSO] 3.18 (m, 1H); 4.10 (m, 2H); 8.69 (s, 1H); 9.01 (t, br, 1H); 13.4 (br, 1H)


1813
[DMSO] 0.87 (t, 3H); 1.14 (d, 3H); 1.50 (m, 2H); 3.90 (m, 1H); 8.52 (d, br, 1H); 8.72 (s, 1H);



13.4 (br, 1H)


1815
[DMSO] 0.89 (t, 3H); 1.15 (d, 3H); 1.30 (m, 2H); 1.47 (m, 2H); 4.00 (m, 1H); 8.54 (br, 1H);



8.72 (s, 1H); 13.4 (br, 1H)


1816
[CDCl3] 0.89 (t, 3H); 1.20 (d, 3H); 1.27-1.37 (m, 6H); 1.51 (m, 2H); 4.16 (m, 1H); 8.75 (br,



1H); 8.90 (s, 1H); 12.1 (br, 1H)


1817
[CDCl3] 0.91 (m, 6H); 1.20 (d, 3H); 1.32 (m, 1H); 1.45 (m, 1H); 1.65 (m, 1H); 4.25 (m, 1H);



8.66 (br, 1H); 8.90 (s, 1H); 11.9 (br, 1H)


1818
[CDCl3] 0.94 (s, 9H); 1.14 (d, 3H); 4.07 (m, 1H); 8.85 (br, 1H); 8.90 (s, 1H)


1819
[CDCl3] 0.95 (m, 6H); 1.18 (d, 3H); 1.79 (m, 1H); 4.04 (m, 1H); 8.75 (br, 1H); 8.89 (s, 1H)


1820
[CDCl3] 0.93 (t, 6H); 1.48 (m, 2H); 1.64 (m, 2H); 3.98 (m, 1H); 8.63 (br, 1H); 8.90 (s, 1H);



11.6 (br, 1H)


1821
[CDCl3] 3.40 (s, 6H); 3.60 (t, 2H); 4.49 (t, 1H); 8.85 (s, br, 2H); 11.4 (br, 1H)


1823
[CDCl3] 3.63 (m, 2H); 3.83 (m, 2H); 8.86 (s, 1H); 9.17 (br, 1H)


1824
[CDCl3] 3.38 (s, 3H); 3.55 (m, 2H); 3.65 (m, 2H); 8.82 (s, 1H); 8.84 (br, 1H); 11.4 (br, 1H)


1826
[CDCl3] 1.25 (d, 3H); 3.39 (s, 3H); 3.43 (m, 2H); 4.38 (m, 1H); 8.67 (br, 1H); 8.82 (s, 1H);



11.5 (br, 1H)


1827
[CDCl3] 1.89 (m, 2H); 3.40 (s, 3H); 3.55 (m, 4H); 8.67 (s, 1H); 8.74 (br, 1H); 11.8 (br, 1H)


1828
[CDCl3] 3.78 (s, 3H); 4.24 (d, 2H); 8.89 (s, 1H); 9.30 (br, 1H)


1833
[DMSO] 2.85 (d, 3H); 8.69 (s, 1H); 8.71 (br, 1H); 13.5 (br, 1H)


1834
[DMSO] 1.12 (t, 3H); 3.30 (m, 2H); 8.70 (s, 1H); 8.75 (t, br, 1H); 13.5 (br, 1H)


1835
[DMSO] 0.89 (t, 3H); 1.52 (m, 2H); 3.25 (q, 2H); 8.70 (s, 1H); 8.75 (t, br, 1H); 13.5 (br, 1H)


1837
[DMSO] 0.59 (m, 2H); 0.76 (m, 2H); 2.86 (m, 1H); 8.66 (s, 1H); 8.76 (br, 1H); 13.3 (br)


1838
[CDCl3] 0.95 (t, 3H); 1.42 (m, 2H); 1.60 (m, 2H); 3.45 (m, 2H); 8.86 (s, 1H); 8.95 (br, 1H)


1839
[CDCl3] 1.81 (m, 2H); 2.00 (m, 2H); 2.42 (m, 2H); 4.54 (m, 1H); 8.84 (s, 1H); 9.17 (d, br,



1H); 12.2 (br, 1H)


1845
[CDCl3] 0.29 (m, 2H); 0.57 (m, 2H); 1.05 (m, 1H); 3.32 (t, 2H); 8.87 (s, 1H); 9.05 (br, 1H);



12.3 (br, 1H)


1847
[CDCl3] 1.00 (d, 6H); 1.90 (m, 1H); 3.30 (t, 2H); 8.85 (s, 1H); 9.00 (br, 1H)


1849
[CDCl3] 0.95 (d, 6H); 1.51 (q, 2H); 1.68 (m, 1H); 3.46 (m, 2H); 8.85 (s, 1H); 8.91 (br, 1H)


1851
[DMSO] 3.94 (m, 2H); 5.16 (dd, 2H); 5.90 (m, 1H); 8.70 (s, 1H); 8.85 (t, br, 1H); 13.4 (br,



1H)


1852
[CDCl3] 1.79 (s, 3H); 4.02 (m, 2H); 4.92 (m, 2H); 8.88 (s, 1H); 9.10 (t, br, 1H)


1853
[CDCl3] 2.26 (m, 1H); 4.22 (m, 2H); 8.86 (s, 1H); 9.25 (br, 1H)


1854
[DMSO] 0.87 (t, 3H); 1.13 (d, 3H); 1.50 (m, 2H); 3.91 (m, 1H); 8.55 (d, br, 1H); 8.70 (br,



1H); 13.5 (br, 1H)


1856
[DMSO] 0.89 (t, 3H); 1.15 (d, 3H); 1.30 (m, 2H); 1.49 (m, 2H); 4.01 (m, 1H); 8.51 (d, br, 1H);



8.71 (s, 1H); 13.6 (br, 1H)


1857
[CDCl3] 0.87 (t, 3H); 1.22 (8, 3H); 1.25-1.35 (m, 6H); 1.53 (m, 2H); 4.14 (m, 1H); 8.81 (d,



br, 1H); 8.88 (s, 1H)


1858
[CDCl3] 0.92 (m, 6H); 1.22 (d, 3H); 1.33 (m, 1H); 1.48 (m, 1H); 1.65 (m, 1H); 4.25 (m, 1H);



8.84 (br, 1H); 8.88 (s, 1H); 12.3 (br, 1H)


1860
[CDCl3] 0.95 (m, 6H); 1.18 (d, 3H); 1.81 (m, 1H); 4.05 (m, 1H); 8.90 (s, 1H); 9.01 (d, br, 1H)


1861
[DMSO] 0.88 (t, 6H); 1.45 (m, 2H); 1.55 (m, 2H); 3.79 (m, 1H); 8.40 (d, br, 1H); 8.70 (s, 1H);



13.5 (br, 1H)


1867
[DMSO] 3.29 (s, 3H); 3.47 (m, 4H); 8.73 (s, 1H); 8.79 (br, 1H); 13.6 (br, 1H)


1869
[CDCl3] 1.28 (d, 3H); 3.39 (s, 3H); 3.45 (m, 2H); 4.35 (m, 1H); 8.81 (s, 1H); 8.86 (br, 1H);



12.0 (br, 1H)


1870
[CDCl3] 1.90 (m, 2H); 3.41 (s, 3H); 3.56 (m, 4H); 8.62 (s, 1H); 8.76 (br, 1H); 11.9 (br, 1H)


1876
[DMSO] 8.18 (br, 1H); 8.35 (br, 1H); 8.79 (s, 1H); 13.7 (br, 1H)


1877
[DMSO] 2.83 (d, 3H); 8.70 (br, 2H); 13.5 (br, 1H)


1878
[DMSO] 1.12 (t, 3H); 3.32 (m, 2H); 8.71 (s, 1H); 8.76 (t, br, 1H); 13.4 (br, 1H)


1879
[DMSO] 0.90 (t, 3H); 1.51 (m, 2H); 3.25 (q, 2H); 8.70 (s, 1H); 8.78 (t, br, 1H); 13.5 (br, 1H)


1880
[DMSO] 1.18 (d, 6H); 4.07 (m, 2H); 8.57 (d, br, 1H); 8.72 (s, 1H); 13.4 (br, 1H)


1881
[DMSO] 0.58 (m, 2H); 0.74 (m, 2H); 2.85 (m, 1H); 8.66 (s, 1H); 8.74 (br, 1H); 13.4 (br, 1H)


1882
[DMSO] 0.89 (t, 3H); 1.31 (m, 2H); 1.50 (m, 2H); 3.30 (m, 2H); 8.70 (s, 1H); 8.75 (br, 1H)


1883
[DMSO] 1.69 (m, 2H); 2.02 (m, 2H); 2.25 (m, 2H); 4.39 (m, 1H); 8.70 (s, 1H); 8.95 (br, 1H)


1884
[CDCl3] 1.47 (s, 9H); 8.87 (s, 1H); 9.02 (br, 1H); 12.2 (br, 1H)


1885
[CDCl3] 3.12 (s, 6H); 8.16 (s, 1H)


1886
[DMSO] 0.23 (m, 2H); 0.45 (m, 2H); 1.02 (m, 1H); 3.19 (t, 2H); 8.72 (s, 1H); 8.83 (br, 1H);



13.4 (br, 1H)


1887
[DMSO] 0.90 (s, 9H); 3.14 (d, 2H); 8.72 (br, 1H); 8.67 (s, 1H); 13.4 (br, 1H)


1888
[DMSO] 0.90 (d, 6H); 1.84 (m, 1H); 3.12 (t, 2H); 8.68 (s, 1H); 8.73 (t, br, 1H); 13.4 (br, 1H)


1890
[DMSO] 0.90 (d, 6H); 1.41 (m, 2H); 1.60 (m, 1H); 3.30 (m, 2H); 8.69 (s, 1H); 8.72 (t, br, 1H);



13.5 (br, 1H)


1892
[DMSO] 3.94 (m, 2H); 5.15 (dd, 2H); 5.89 (m, 1H); 8.70 (s, 1H); 8.85 (t, br, 1H)


1894
[DMSO] 1.70 (s, 3H); 3.86 (d, 2H); 4.84 (d, 2H); 8.68 (s, 1H); 8.95 (br, 1H); 13.4 (br, 1H)


1895
[DMSO] 3.10 (t, 1H); 4.05 (m, 2H); 8.25 (br, 1H); 8.30 (s, 1H); 11.5 (br, 1H)


1897
[CDCl3] 0.95 (t, 3H); 1.24 (d, 3H); 1.60 (m, 2H); 4.10 (m, 1H); 8.87 (br, 2H)


1899
[CDCl3] 0.92 (t, 3H); 1.23 (d, 3H); 1.40 (m, 2H); 1.52 (m, 2H); 4.17 (m, 1H); 8.88 (s, 1H);



8.91 (br, 1H)


1900
[DMSO] 0.86 (t, 3H); 1.15 (d, 3H); 1.25 (m, 6H); 1.48 (m, 2H); 4.00 (m, 1H); 8.53 (d, br, 1H);



8.71 (s, 1H); 13.4 (br, 1H)


1903
[DMSO] 0.89 (d, 6H); 1.13 (d, 3H); 1.27 (m, 1H); 1.48 (m, 1H); 1.62 (m, 1H); 4.09 (m, 1H);



8.50 (d, br, 1H); 8.71 (s, 1H); 13.5 (br, 1H)


1904
[DMSO] 0.81 (s, 9H); 1.07 (d, 3H); 3.90 (m, 1H); 8.43 (d, br, 1H); 8.67 (s, 1H); 13.4 (br, 1H)


1905
[DMSO] 0.88 (d, 6H); 1.10 (d, 3H); 1.75 (m, 1H); 1.48 (m, 1H); 3.85 (m, 1H); 8.49 (d, br,



1H); 8.70 (s, 1H); 13.5 (br, 1H)


1907
[DMSO] 0.87 (t, 6H); 1.43 (m, 2H); 1.55 (m, 2H); 3.78 (m, 1H); 8.55 (br, 1H); 8.67 (s, 1H);



13.5 (br, 1H)


1910
[CDCl3] 3.41 (s, 6H); 3.62 (t, 2H); 4.50 (t, 1H); 8.82 (s, 1H); 8.95 (br, 1H); 11.2 (br, 1H)


1912
[DMSO] 3.39 (m, 2H); 3.52 (m, 2H); 4.83 (br, 1H); 8.76 (s, 1H); 8.80 (t, br, 1H); 13.6 (br, 1H)


1913
[DMSO] 3.26 (s, 3H); 3.47 (m, 4H); 8.71 (s, 1H); 8.79 (br, 1H)


1916
[CDCl3] 1.27 (d, 3H); 3.39 (s, 3H); 3.44 (m, 2H); 4.38 (m, 1H); 8.83 (s, 1H); 8.95 (br, 1H);



12.1 (br, 1H)


1917
[DMSO] 1.75 (m, 2H); 3.24 (s, 3H); 3.39 (m, 4H); 8.70 (s, 1H); 8.81 (br, 1H); 13.4 (br, 1H)


1918
[DMSO] 3.66 (s, 3H); 4.12 (d, 2H); 8.71 (s, 1H); 9.02 (t, br, 1H), 13.5 (br, 1H)


1923
[DMSO] 2.81 (d, 3H); 8.72 (s, 1H); 8.77 (br, 1H); 13.4 (br)


1924
[DMSO] 1.14 (t, 3H); 3.35 (m, 2H); 8.74 (s, 1H); 8.82 (t, br, 1H); 13.4 (br)


1925
[DMSO] 0.89 (t, 3H); 1.53 (m, 2H); 3.28 (q, 2H); 8.73 (s, 1H); 8.80 (t, br, 1H)


1926
[DMSO] 1.18 (d, 6H); 4.10 (m, 1H); 8.63 (d, br, 1H); 8.75 (s, 1H); 13.4 (br, 1H)


1927
[DMSO] 0.60 (m, 2H); 0.75 (m, 2H); 2.87 (m, 1H); 8.69 (s, 1H); 8.80 (br, 1H)


1928
[DMSO] 0.89 (t, 3H); 1.34 (m, 2H); 1.51 (m, 2H); 3.30 (m, 2H); 8.72 (s, 1H); 8.79 (br, 1H)


1929
[DMSO] 1.72 (m, 2H); 2.05 (m, 2H); 2.27 (m, 2H); 4.38 (m, 1H); 8.73 (s, 1H); 9.00 (d, br,



1H); 13.3 (br)


1930
[DMSO] 1.37 (s, 9H); 8.30 (br, 1H); 8.66 (s, 1H); 13.4 (br)


1931
[DMSO] 2.80 (s, 3H); 2.96 (s, 3H); 8.27 (s, 1H); 12.4 (br, 1H)


1932
[DMSO] 1.01 (t, 3H); 1.11 (t, 3H); 3.10 (q, 2H); 3.42 (q, 2H); 8.25 (s, 1H); 12.3 (br, 1H)


1933
[DMSO] 0.26 (m, 2H); 0.47 (m, 2H); 1.04 (m, 1H); 3.20 (m, 2H); 8.77 (s, 1H); 8.87 (t, br,



1H); 13.5 (br, 1H)


1934
[DMSO] 0.90 (s, 9H); 3.13 (d, 2H); 8.62 (t, br, 1H); 8.70 (s, 1H); 13.3 (br, 1H)


1935
[DMSO] 0.90 (d, 6H); 1.85 (m, 1H); 3.13 (m, 2H); 8.71 (s, 1H); 8.75 (t, br, 1H); 13.4 (br, 1H)


1937
[CDCl3] 0.94 (d, 6H); 1.49 (q, 2H); 1.66 (m, 1H); 3.46 (m, 2H); 8.75 (br, 1H); 8.85 (s, 1H);



11.5 (br)


1939
[DMSO] 3.93 (m, 2H); 5.19 (dd, 2H); 5.89 (m, 1H); 8.72 (s, 1H); 8.90 (t, br, 1H); 13.3 (br,



1H)


1941
[DMSO] 1.72 (s, 3H); 3.87 (d, 2H); 4.87 (d, 2H); 8.73 (s, 1H); 8.89 (t, br, 1H); 13.3 (br)


1942
[DMSO] 3.18 (m, 1H); 4.10 (m, 2H); 8.70 (s, 1H); 9.04 (t, br, 1H); 13.3 (br, 1H)


1944
[DMSO] 0.89 (t, 3H); 1.14 (d, 3H); 1.51 (m, 2H); 3.91 (m, 1H); 8.55 (d, br, 1H); 8.75 (s, 1H);



13.4 (br, 1H)


1946
[DMSO] 0.89 (t, 3H); 1.15 (d, 3H); 1.31 (m, 2H); 1.47 (m, 2H); 4.01 (m, 1H); 8.56 (br, 1H);



8.74 (s, 1H); 13.4 (br, 1H)


1947
[DMSO] 0.85 (t, 3H); 1.15 (d, 3H); 1.20-1.35 (m, 6H); 1.49 (m, 2H); 4.00 (m, 1H); 8.58 (d,



br, 1H); 8.74 (s, 1H); 13.4 (br, 1H)


1948
[DMSO] 0.88 (d, 6H); 1.15 (d, 3H); 1.27 (m, 1H); 1.48 (m, 1H); 1.61 (m, 1H); 4.10 (m, 1H);



8.56 (d, br, 1H); 8.74 (s, 1H); 13.5 (br, 1H)


1949
[CDCl3] 0.94 (s, 1H); 1.15 (d, 3H); 4.09 (m, 1H); 8.89 (br, 1H); 8.91 (s, 1H)


1950
[CDCl3] 0.94 (m, 6H); 1.17 (d, 3H); 1.80 (m, 1H); 4.05 (m, 1H); 8.88 (br, 1H); 8.92 (s, 1H)


1951
[CDCl3] 0.92 (t, 6H); 1.49 (m, 2H); 1.65 (m, 2H); 3.99 (m, 1H); 8.78 (br, 1H); 8.92 (s, 1H)


1952
[CDCl3] 3.41 (s, 6H); 3.61 (t, 2H); 4.50 (t, 1H); 8.84 (s, br, 2H); 11.4 (br, 1H)


1954
[DMSO] 3.39 (m, 2H); 3.52 (m, 2H); 4.80 (br, 1H); 8.79 (s, 1H); 8.82 (t, br, 1H); 13.5 (br, 1H)


1955
[CDCl3] 3.38 (s, 3H); 3.55 (m, 2H); 3.66 (m, 2H); 8.78 (s, br, 1H); 8.82 (s, 1H); 11.5 (br)


1957
[CDCl3] 1.27 (d, 3H); 3.38 (s, 3H); 3.42 (m, 2H); 4.38 (m, 1H); 8.75 (br, 1H); 8.84 (s, 1H);



12.3 (br, 1H)


1958
[CDCl3] 1.89 (m, 2H); 3.41 (s, 3H); 3.56 (m, 4H); 8.61 (s, 1H); 8.68 (br, 1H); 11.8 (br, 1H)


1959
[DMSO] 3.67 (s, 3H); 4.12 (d, 2H); 8.73 (s, 1H); 9.04 (t, br, 1H); 13.5 (br, 1H)


1964
[DMSO] 8.25 (br, 1H); 8.37 (br, 1H); 8.47 (s, 1H); 13.7 (br, 1H)


1965
[DMSO] 2.82 (d, 3H); 8.37 (s, 1H); 8.72 (d, br, 1H); 13.5 (br, 1H)


1966
[DMSO] 1.13 (t, 3H); 3.34 (m, 2H); 8.39 (s, 1H); 8.76 (t, br, 1H); 13.5 (br, 1H)


1967
[DMSO] 0.90 (t, 3H); 1.53 (m, 2H); 3.26 (q, 2H); 8.39 (s, 1H); 8.75 (t, br, 1H); 13.5 (br, 1H)


1968
[DMSO] 1.18 (d, 6H); 4.09 (m, 1H); 8.41 (s, 1H); 8.58 (d, br, 1H); 13.5 (br, 1H)


1969
[DMSO] 0.59 (m, 2H); 0.75 (m, 2H); 2.86 (m, 1H); 8.34 (s, 1H); 8.73 (d, br, 1H); 13.4 (br,



1H)


1970
[DMSO] 0.89 (t, 3H); 1.33 (m, 2H); 1.51 (m, 2H); 3.31 (m, 2H); 8.39 (s, 1H); 8.73 (t, br, 1H);



13.5 (br, 1H)


1971
[DMSO] 1.70 (m, 2H); 2.04 (m, 2H); 2.25 (m, 2H); 4.38 (m, 1H); 8.39 (s, 1H); 8.92 (d, br,



1H); 13.4 (br, 1H)


2006
[DMSO] 8.25 (br, 1H); 8.35 (br, 1H); 8.61 (s, 1H); 13.7 (br, 1H)


2007
[DMSO] 2.82 (d, 3H); 8.51 (s, 1H); 8.74 (d, br, 1H); 13.5 (br, 1H)


2008
[DMSO] 1.13 (t, 3H); 3.33 (m, 2H); 8.53 (s, 1H); 8.78 (t, br, 1H); 13.5 (br, 1H)


2009
[DMSO] 0.89 (t, 3H); 1.53 (m, 2H); 3.26 (q, 2H); 8.51 (s, 1H); 8.76 (t, br, 1H); 13.5 (br, 1H)


2010
[DMSO] 1.18 (d, 6H); 4.07 (m, 1H); 8.53 (s, 1H); 8.61 (d, br, 1H); 13.5 (br, 1H)


2011
[DMSO] 0.58 (m, 2H); 0.74 (m, 2H); 2.86 (m, 1H); 8.48 (s, 1H); 8.77 (d, br, 1H); 13.4 (br,



1H)


2012
[DMSO] 0.90 (t, 3H); 1.33 (m, 2H); 1.51 (m, 2H); 3.30 (m, 2H); 8.52 (s, 1H); 8.77 (t, br, 1H);



13.5 (br, 1H)


2013
[DMSO] 1.72 (m, 2H); 2.05 (m, 2H); 2.25 (m, 2H); 4.39 (m, 1H); 8.51 (s, 1H); 8.95 (d, br,



1H); 13.4 (br, 1H)


2014
[DMSO] 1.37 (s, 9H); 8.31 (br, 1H); 8.45 (s, 1H); 13.4 (br, 1H)


2015
[DMSO] 2.82 (s, 3H); 2.95 (s, 3H); 8.12 (s, 1H); 12.5 (br, 1H)


2017
[DMSO] 0.26 (m, 2H); 0.47 (m, 2H); 1.04 (m, 1H); 3.30 (m, 2H); 8.56 (s, 1H); 8.86 (t, br,



1H); 13.5 (br, 1H)


2018
[DMSO] 0.91 (s, 9H); 3.13 (d, 2H); 8.47 (s, 1H); 8.63 (t, br, 1H); 13.5 (br, 1H)


2019
[DMSO] 0.90 (d, 6H); 1.83 (m, 1H); 3.13 (m, 2H); 8.50 (s, 1H); 8.73 (t, br, 1H); 13.4 (br, 1H)


2021
[DMSO] 0.89 (d, 6H); 1.42 (q, 2H); 1.62 (m, 1H); 3.31 (m, 2H); 8.51 (s, 1H); 8.75 (t, br, 1H);



13.5 (br, 1H)


2023
[DMSO] 3.94 (m, 2H); 5.18 (dd, 2H); 5.89 (m, 1H); 8.52 (s, 1H); 8.88 (t, br, 1H); 13.4 (br,



1H)


2025
[DMSO] 1.72 (s, 3H); 3.86 (d, 2H); 4.85 (d, 2H); 8.50 (s, 1H); 8.87 (t, br, 1H); 13.4 (br, 1H)


2026
[DMSO] 3.18 (m, 1H); 4.10 (m, 2H); 8.48 (s, 1H); 9.02 (t, br, 1H); 13.3 (br, 1H)


2030
[CDCl3] 0.93 (t, 3H); 1.23 (d, 3H); 1.40 (m, 2H); 1.52 (m, 2H); 4.21 (m, 1H); 8.74 (s, 1H);



8.97 (d, br, 1H); 12.9 (br, 1H)


2031
[DMSO] 0.85 (t, 3H); 1.15 (d, 3H); 1.20-1.35 (m, 6H); 1.48 (m, 2H); 3.99 (m, 1H); 8.52 (s,



1H); 8.54 (d, br, 1H); 13.5 (br, 1H)


2032
[DMSO] 0.88 (d, 6H); 1.14 (d, 3H); 1.27 (m, 1H); 1.48 (m, 1H); 1.62 (m, 1H); 4.10 (m, 1H);



8.51 (s, 1H); 8.53 (d, br, 1H); 13.5 (br, 1H)


2035
[DMSO] 0.86 (t, 6H); 1.45 (m, 2H); 1.55 (m, 2H); 3.78 (m, 1H); 8.82 (d, br, 1H); 8.51 (s, 1H);



13.5 (br, 1H)


2036
[CDCl3] 3.41 (s, 6H); 3.61 (t, 2H); 4.50 (t, 1H); 8.67 (s, 1H); 9.00 (br, 1H); 11.7 (br, 1H)


2038
[DMSO] 3.35 (m, 2H); 3.53 (m, 2H); 4.81 (br, 1H); 8.56 (s, 1H); 8.80 (t, br, 1H); 13.6 (br, 1H)


2039
[CDCl3] 3.38 (s, 3H); 3.56 (m, 2H); 3.65 (m, 2H); 8.65 (s, 1H); 9.01 (s, 1H); 11.8 (br, 1H)


2041
[DMSO] 1.15 (d, 3H); 3.30 (s, 3H); 3.40 (m, 2H); 4.18 (m, 1H); 8.52 (s, 1H); 8.64 (d, br, 1H);



13.4 (br, 1H)


2048
[DMSO] 8.20 (br, 1H); 8.37 (br, 1H); 8.81 (s, 1H); 13.7 (br, 1H)


2090
[DMSO] 7.45 (d, 1H); 8.14 (br, 1H); 8.42 (br, 1H); 8.48 (d, 1H); 13.7 (br, 1H)


2091
[DMSO] 2.84 (d, 3H); 7.42 (d, 1H); 8.41 (d, 1H); 8.79 (br, 1H); 13.4 (br, 1H)


2092
[DMSO] 1.12 (t, 3H); 3.32 (m, 2H); 7.42 (d, 1H); 8.42 (d, 1H); 8.83 (br, 1H); 13.4 (br, 1H)


2093
[DMSO] 0.89 (t, 3H); 1.54 (m, 2H); 3.27 (q, 2H); 7.42 (d, 1H); 8.41 (d, 1H); 8.82 (br, 1H);



13.4 (br, 1H)


2094
[DMSO] 1.18 (d, 6H); 4.11 (m, 1H); 7.41 (d, 1H); 8.41 (d, 1H); 8.63 (br, 1H); 13.4 (br, 1H)


2095
[CDCl3] 0.61 (m, 2H); 0.88 (m, 2H); 3.00 (m, 1H); 6.89 (d, 1H); 8.68 (d, 1H); 9.35 (br, 1H);



12.5 (br, 1H)


2096
[DMSO] 0.89 (t, 3H); 1.33 (m, 2H); 1.52 (m, 2H); 3.32 (m, 2H); 7.42 (d, 1H); 8.41 (d, 1H);



8.81 (br, 1H); 13.3 (br, 1H)


2097
[DMSO] 1.72 (m, 2H); 2.05 (m, 2H); 2.46 (m, 2H); 4.41 (m, 1H); 7.43 (d, 1H); 8.39 (d, 1H);



8.96 (br, 1H); 13.3 (br, 1H)


2101
[DMSO] 0.26 (m, 2H), 0.47 (m, 2H); 1.06 (m, 1H); 3.22 (m, 2H); 7.45 (d, 1H); 8.45 (d, 1H);



8.91 (br, 1H); 13.4 (br, 1H)


2102
[DMSO] 0.92 (s, 9H); 3.15 (d, 2H); 7.40 (d, 1H); 8.41 (d, 1H); 8.75 (br, 1H); 13.3 (br, 1H)


2103
[DMSO] 0.90 (d, 6H); 1.83 (m, 1H); 3.14 (t, 2H); 7.40 (d, 1H); 8.40 (d, 1H); 8.81 (t, br, 1H);



13.3 (br, 1H)


2105
[DMSO] 0.90 (d, 6H); 1.42 (m, 2H); 1.62 (m, 1H); 3.33 (m, 2H); 7.41 (d, 1H); 8.40 (d, 1H);



8.80 (br, 1H); 13.3 (br, 1H)


2107
[DMSO] 3.95 (t, 2H); 5.17 (dd, 2H); 5.90 (m, 1H); 7.41 (d, 1H); 8.41 (d, 1H); 8.93 (br, 1H);



13.3 (br, 1H)


2109
[DMSO] 1.72 (s, 3H); 3.88 (d, 2H); 4.85 (d, 2H); 7.42 (d 1H); 8.42 (d, 1H); 8.94 (br, 1H);



13.3 (br, 1H)


2110
[DMSO] 3.17 (m, 1H); 4.11 (m, 2H); 7.41 (d, 1H); 8.40 (d, 1H); 9.06 (br, 1H), 13.3 (br, 1H)


2112
[DMSO] 0.89 (t, 3H); 1.15 (d, 3H); 1.53 (m, 2H); 3.95 (m, 1H); 7.42 (d, 1H); 8.42 (d, 1H);



8.60 (br, 1H); 13.4 (br, 1H)


2114
[DMSO] 0.88 (t, 3H); 1.15 (d, 3H); 1.32 (m, 2H); 1.48 (m, 2H); 4.04 (m, 1H); 7.42 (d, 1H);



8.41 (d, 1H); 8.59 (br, 1H); 13.4 (br, 1H)


2115
[DMSO] 0.85 (t, 3H); 1.16 (d, 3H); 1.20-1.35 (m, 6H); 1.50 (m, 2H); 4.02 (m, 1H); 7.42 (d,



1H); 8.44 (d, 1H); 8.62 (d, br, 1H), 13.4 (br, 1H)


2116
[DMSO] 0.88 (d, 6H); 1.14 (d, 3H); 1.25 (m, 1H); 1.48 (m, 1H); 1.63 (m, 1H); 4.21 (m, 1H);



6.92 (d, 1H); 8.42 (d, 1H); 8.59 (d, br, 1H), 13.4 (br, 1H)


2122
[DMSO] 3.40 (m, 2H); 3.52 (m, 2H); 4.82 (br, 1H); 7.44 (d, 1H); 8.46 (d, 1H); 8.88 (br, 1H);



13.4 (br, 1H)


2133
[DMSO] 2.83 (d, 3H); 8.58 (s, 1H); 8.82 (d, br, 1H); 13.4 (br, 1H)


2134
[DMSO] 1.14 (t, 3H); 3.34 (m, 2H); 8.60 (s, 1H); 8.86 (t, br, 1H); 13.5 (br, 1H)


2135
[DMSO] 0.89 (t, 3H); 1.54 (m, 2H); 3.26 (q, 2H); 8.59 (s, 1H); 8.85 (t, br, 1H); 13.5 (br, 1H)


2137
[DMSO] 0.60 (m, 2H); 0.75 (m, 2H); 2.88 (m, 1H); 8.55 (s, 1H); 8.85 (d, br, 1H); 13.4 (br,



1H)


2138
[DMSO] 0.90 (t, 3H); 1.33 (m, 2H); 1.51 (m, 2H); 3.31 (m, 2H); 8.59 (s, 1H); 8.84 (t, br, 1H);



13.4 (br, 1H)


2139
[DMSO] 1.71 (m, 2H); 2.05 (m, 2H); 2.25 (m, 2H); 4.40 (m, 1H); 8.62 (s, 1H); 9.04 (d, br,



1H); 13.4 (br, 1H)


2143
[DMSO] 0.26 (m, 2H); 0.47 (m, 2H); 1.05 (m, 1H); 3.20 (m, 2H); 8.63 (s, 1H); 8.94 (t, br,



1H); 13.4 (br, 1H)


2144
[DMSO] 0.91 (s, 9H); 3.15 (d, 2H); 8.55 (s, 1H); 8.66 (t, br, 1H); 13.3 (br, 1H)









3. Biological Examples
3.1 Scoring of the Damage
The damage to the plants is scored visually using a scale of 0-100%, in comparison to control plants:
0%=no noticeable effect compared to the untreated plant
100%=the treated plants dies.
3.2 Post-Emergence Herbicide Action and Safener Action
Seeds or rhizome pieces of monocotyledonous and dicotyledonous harmful plants and crop plants are placed in sandy loam soil in plastic pots, covered with soil and cultivated in the greenhouse under good growth conditions. Alternatively, harmful plants encountered in paddy rice cultivation are cultivated in pots in which the surface of the soil is covered by up to 2 cm of water. Three weeks after sowing, the test plants are treated at the three-leaf stage. The herbicide/safener active compound combinations according to the invention, formulated as emulsion concentrates, and in parallel tests the individual active compounds formulated in a corresponding manner, are sprayed at various dosages at a water application rate of 3001 l/ha (converted) onto the green parts of the plants, and, after the test plants were left to stand in the greenhouse for about 2 to 3 weeks under optimum growth conditions, the effect of the preparations is scored visually in comparison to untreated controls. In the case of rice or harmful plants encountered in the cultivation of rice, the active compounds are also added directly to the irrigation water (application analogously to the so-called granule application) or sprayed onto the plants and into the irrigation water.
The tests show that the safeners according to the invention in combination with herbicides, in a herbicides:safener ratio of from 2:1 to 1:20, considerably reduce the damage caused by the herbicide to crop plants such as corn, rice, wheat or barley or other cereals or dicotyledonous crop plants such as soybeans or oilseed rape compared to the application of the individual herbicides without safener, such that from 30% up to 100% less damage to the crop plant is observed. At the same time, the action of the herbicide against economically important harmful plants is not, or not essentially, adversely affected, so that good herbicidal post-emergence action against a broad spectrum of weed grasses and broad-leaved weeds can be achieved.
In barley, for example, a good safener action for the herbicide mesosulfuron-methyl could be achieved using the compounds Nos. 1, 2, 3, 5, 7, 9, 10, 13, 14, 22, 25, 26, 30, 34, 36, 40, 57, 64, 66, 79, 100, 101, 102, 105, 114, 115, 116, 117, 119, 123, 124, 128, 130, 134, 136, 138, 140, 146, 148, 153, 154, 155, 157, 163, 165, 168, 169, 171, 178, 193, 194, 214, 341, 342, 344, 345, 346, 382, 384, 392, 398, 405, 407, 455, 457, 489, 496, 498, 571, 909, 910, 911, 913, 943, 950, 960, 1023, 1026, 1029, 1030, 1201, 1481, 1487, 1598, 1599, 1600, 1636, 1907.
In corn, for example, a good safener action for the herbicide tembotrione could be achieved using the following compounds from Table 1: 4, 6, 9, 10, 14, 24, 32, 34, 36, 43, 64, 66, 71, 75, 79, 105, 114, 118, 140, 146, 148, 153, 169, 178, 210, 214, 345, 51, 95, 341, 456, 457, 489, 496, 498, 909, 911, 913, 943, 960, 1026, 1139, 1368, 1371, 1485, 1488, 1596, 1597, 1598, 1599, 1600, 1604, 1619, 1625, 1629, 1636, 1638, 1646, 1758.
In rice, for example, the following compounds from Table 1 achieved good safener action for fenoxaprop-P-ethyl and thiencarbazone or thiencarbazone-methyl:
1, 2, 3, 4, 9, 16, 20, 22, 34, 41, 47, 54, 57, 75, 76, 79, 80, 81, 101, 103, 105, 114, 115, 117, 118, 120, 127, 128, 130, 153, 154, 157, 162, 165, 169, 171, 178, 218, 271, 341, 342, 344, 345, 346, 350, 355, 392, 398, 405, 407, 456, 973, 1482, 1596, 1597, 1598, 1600, 1603, 1609, 1625, 1638, 1646, 1659.
3.3 Pre-Emergence Herbicide Action and Safener Action
Seeds or rhizome pieces of monocotyledonous and dicotyledonous weed plants and crop plants were placed in sandy loam soil in plastic pots and covered with soil. The herbicide/safener active compound combinations according to the invention, formulated as suspension emulsion concentrates, and in parallel tests the individual active compounds formulated in a corresponding manner, were then, at various dosages at a water application rate of 600 to 800 l/ha (converted), applied to the surface of the covering soil.
After the treatment, the pots were placed in the greenhouse and kept under good growth conditions for the weeds and the crop plants. Visual scoring of the plant damage or emergence damage was carried out after the test plants had emerged after a test period of 3 to 4 weeks, in comparison to untreated controls. The test results showed that the compounds according to the invention prevented or reduced herbicide damage to the crop plants without reducing, or reducing substantially, the herbicide action against the harmful plants.
For example, example Nos. 2, 19, 39, 72, 104, 122, 155, 193, 194, 217, 232, 271, 341, 380, 392, 1368, 1597, 1625, 1636 of Table 1 showed in the test in combination with the herbicide isoxaflutol a good safener action in corn. The herbicidal action of the herbicidally active compounds used was not adversely affected.
Accordingly, in many cases, the safeners, combined with herbicides, are suitable for the selective control of harmful plants in the pre-emergence treatment of crops of useful plants.
3.4 Seed Treatment
Seeds of crop plants were mixed in bottles with the safeners according to the invention, formulated as suspension or emulsion concentrates, and water, and the mixture was shaken well so that the seeds were coated evenly with the formulation of the safener in question. The seeds or the emerged plants were then tested with herbicides in the pre- or post-emergence method according to the tests of examples 3.3 and 3.2, respectively.
In the treatment of seed, too, the safeners showed good activity. The herbicidal action of the herbicidally active compounds used was not adversely affected.
Having thus described in detail various embodiments of the present invention, it is to be understood that the invention defined by the above paragraphs is not to be limited to particular details set forth in the above description as many apparent variations thereof are possible without departing from the spirit or scope of the present invention.

## Claims

1. A compound of the formula (I) or a salt thereof,




wherein the identities of R1, R2, R3, and R4 for the compound of formula (I) are selected from the group consisting of (A), (B), and (C);
wherein in (A):
R1 is a (C1-C6)-haloalkyl radical;
R2 is hydrogen or halogen; and
the identities of R3 and R4 are selected from the group consisting of (i), (ii) (iii), and (iv);
where for (i):
R3 is:
(a) hydrogen, (C1-C16)-alkyl, (C2-C16)-alkenyl, or (C2-C16)-alkynyl;
where each of the 3 last mentioned radicals is unsubstituted or substituted by one or more radicals selected from the group consisting of halogen, hydroxyl, cyano, (C1-C4)-alkoxy, (C1-C4)-haloalkoxy, (C1-C4)-alkylthio, (C1-C4)-alkylamino, di[(C1-C4)-alkyl]amino, [(C1-C4)-alkoxy]-carbonyl, and [(C1-C4)-haloalkoxy]-carbonyl; or

(b) (C3-C6)-cycloalkyl, (C4-C6)-cycloalkenyl, (C3-C6)-cycloalkyl which is condensed at one side of the ring to a 4- to 6-membered saturated or unsaturated carbocyclic ring, or (C4-C6)-cycloalkenyl which is condensed at one side of the ring to a 4- to 6-membered saturated or unsaturated carbocyclic ring;
where each of the 4 lastmentioned radicals is unsubstituted or substituted by one or more radicals selected from the group consisting of halogen, hydroxyl, cyano, (C1-C4)-alkyl, (C1-C4)-haloalkyl, (C1-C4)-alkoxy, (C1-C4)-haloalkoxy, (C1-C4)-alkylthio, (C1-C4)-alkylamino, di[(C1-C4)-alkyl]-amino, [(C1-C4)-alkoxy]-carbonyl, [(C1-C4)-haloalkoxy]-carbonyl, (C3-C6)-cycloalkyl, which is unsubstituted or substituted, phenyl, which is unsubstituted or substituted, and heterocyclyl, which is unsubstituted or substituted; and


R4 is:
(a) (C1-C16)-alkyl, (C2-C16)-alkenyl, or (C2-C16)-alkynyl;
where each of the 3 lastmentioned radicals is unsubstituted or substituted by one or more radicals selected from the group consisting of halogen, hydroxyl, cyano, (C1-C4)-alkoxy, (C1-C4)-haloalkoxy, (C1-C4)-alkylthio, (C1-C4)-alkylamino, di[(C1-C4)-alkyl]-amino, [(C1-C4)-alkoxy]-carbonyl, and [(C1-C4)-haloalkoxy]-carbonyl; or

(b) (C3-C6)-cycloalkyl, (C4-C6)-cycloalkenyl, (C3-C6)-cycloalkyl which is condensed at one side of the ring to a 4- to 6-membered saturated or unsaturated carbocyclic ring, or (C4-C6)-cycloalkenyl which is condensed at one side of the ring to a 4- to 6-membered saturated or unsaturated carbocyclic ring;
where each of the 4 lastmentioned radicals is unsubstituted or substituted by one or more radicals selected from the group consisting of halogen, hydroxyl, cyano, (C1-C4)-alkyl, (C1-C4)-haloalkyl, (C1-C4)-alkoxy, (C1-C4)-haloalkoxy, (C1-C4)-alkylthio, (C1-C4)-alkylamino, di[(C1-C4)-alkyl]-amino, [(C1-C4)-alkoxy]-carbonyl, [(C1-C4)-haloalkoxy]-carbonyl, (C3-C6)-cycloalkyl, which is unsubstituted or substituted, phenyl, which is unsubstituted or substituted, and heterocyclyl, which is unsubstituted or substituted; and




where for (ii):
R3 is (C1-C4)-alkoxy, (C2-C4)-alkenyloxy, (C2-C6)-alkynyloxy, or (C2-C4)-haloalkoxy; and
R4 is hydrogen or (C1-C4)-alkyl; or and

where for (iii) R3 and R4 together with the directly attached nitrogen atom are a four- to eight-membered heterocyclic ring which, in addition to the nitrogen atom, may also comprise further hetero ring atoms, and which is unsubstituted or substituted by one or more radicals selected from the group consisting of halogen, cyano, nitro, (C1-C4)-alkyl, (C1-C4)-haloalkyl, (C1-C4)-alkoxy, (C1-C4)-haloalkoxy, and (C1-C4)-alkylthio; and
where for (iv) R3 and R4 together with the directly attached nitrogen atom are the group —N═CR5—NR6R7 in which:
R5 is hydrogen or (C1-C6)-alkyl, and
R6, R7 independently of one another are hydrogen or (C1-C4)-alkyl, or
R6 and R7 together with the directly attached nitrogen atom form a five- to seven-membered heterocyclic ring; and

wherein in (B):
R1 is a (C1-C6)-haloalkyl radical;
R2 is halogen;
R3 is hydrogen; and
R4 is hydrogen; and

wherein in (C):
R1 is a radical of the formula CF2CF3, CF2CF2H, CF2CF2Cl, CFClCF3, CFHCF3, CF(CF3)2, CH(CF3)2, CF2CF2CF3, or C(CH3)2F;
R2 is hydrogen;
R3 is hydrogen; and
R4 is hydrogen.

2. A process for preparing compounds of the general formula (I) or salts thereof as defined in claim 1, which comprises:
(a) reacting a carboxylic acid of the general formula (II) with an amine of the formula (III) or a salt thereof to give the compound of the formula (I);
wherein the general formula (II) is:







where R1 and R2 are as defined for the compound of the formula (I) to be prepared;

wherein the formula (III) is:







where R3 and R4 are as defined for the compound of the formula (I) to be prepared; or


(b) reacting a carboxylic ester of the general formula (IV) with an amine of the formula (III) or a salt thereof to give the compound of the formula (I);
wherein the general formula (IV) is:







where R1 and R2 are as defined for the compound of the formula (I) to be prepared and “Alkyl” is an alkyl radical;

wherein the formula (III) is:







where R3 and R4 are as defined for the compound of the formula (I) to be prepared; or


(c) reacting a carbonyl halide or a carboxylic anhydride of the general formula (V) with an amine of the formula (III) or a salt thereof to give the compound of the formula (I);
wherein the general formula (V) is:







where R1 and R2 are as defined for the compound of the formula (I) to be prepared and Hal is a halogen atom or an acyloxy radical;

wherein the formula (III) is:







where R3 and R4 are as defined for the compound of the formula (I) to be prepared; or


(d) if R3 and R4 in the compound of the formula (I) to be prepared are each hydrogen, reacting a compound of the formula (VI) with malonamide to give the compound of the formula (I);
wherein the formula (VD is:







where R1 is as defined for the compound of the formula (I) to be prepared, and “Alkyl” is an alkyl radical.

3. A crop protection composition comprising:
one or more compounds of the formula (I) or salts thereof as defined in claim 1; and
formulation auxiliaries.

4. A crop protection composition comprising:
one or more compounds of the formula (I) or salts thereof as defined in claim 1; and
one or more agrochemicals and, optionally, formulation auxiliaries.

5. The compound as claimed in claim 1;
wherein R3 is:
(a) hydrogen, (C1-C10)-alkyl, (C1-C10)-alkenyl, or (C2-C10)-alkynyl;
where each of the 3 lastmentioned radicals is unsubstituted or substituted by one or more radicals selected from the group consisting of halogen, hydroxyl, cyano, (C1-C4)-alkoxy, (C1-C4)-haloalkoxy, (C1-C4)-alkylthio, (C1-C4)-alkylamino, [(C1-C4)-alkoxy]-carbonyl, and [(C1-C4)-haloalkoxy]-carbonyl; or

(b) (C3-C6)-cycloalkyl, (C4-C6)-cycloalkenyl, (C3-C6)-cycloalkyl which is condensed at one side of the ring to a 4- to 6-membered saturated or unsaturated carbocyclic ring, or (C4-C6)-cycloalkenyl which is condensed at one side of the ring to a 4- to 6-membered saturated or unsaturated carbocyclic ring;
where each of the 4 lastmentioned radicals is unsubstituted or substituted by one or more radicals selected from the group consisting of:
halogen, hydroxyl, cyano, (C1-C4)-alkyl, (C1-C4)-haloalkyl, (C1-C4)-alkoxy, (C1-C4)-haloalkoxy, (C1-C4)-alkylthio, (C1-C4)-alkylamino, di[(C1-C4)-alkyl]-amino, [(C1-C4)-alkoxy]-carbonyl, and [(C1-C4)-haloalkoxy]-carbonyl;
(C3-C6)-cycloalkyl, which is unsubstituted or substituted by one or more radicals selected from the group consisting of halogen, (C1-C4)-alkyl and (C1-C4)-haloalkyl;
phenyl, which is unsubstituted or substituted by one or more radicals selected from the group consisting of halogen, (C1-C4)-alkyl, (C1-C4)-haloalkyl, (C1-C4)-alkoxy, (C1-C4)-haloalkoxy and (C1-C4)-alkylthio; and
heterocyclyl, which is unsubstituted or substituted by one or more radicals selected from the group consisting of halogen, (C1-C4)-alkyl, (C1-C4)-haloalkyl, (C1-C4)-alkoxy, (C1-C4)-haloalkoxy, (C1-C4)-alkylthio and oxo; and



wherein R4 is:
(a) (C1-C10)-alkyl, (C2-C10)-alkenyl, or (C2-C10)-alkynyl;
where each of the 3 lastmentioned radicals is unsubstituted or substituted by one or more radicals selected from the group consisting of halogen, hydroxyl, cyano, (C1-C4)-alkoxy, (C1-C4)-haloalkoxy, (C1-C4)-alkylthio, (C1-C4)-alkylamino, di[(C1-C4)-alkyl]-amino, [(C1-C4)-alkoxy]-carbonyl, and [(C1-C4)-haloalkoxy]-carbonyl; or

(b) (C3-C6)-cycloalkyl, (C4-C6)-cycloalkenyl, (C3-C6)-cycloalkyl which is condensed at one side of the ring to a 4- to 6-membered saturated or unsaturated carbocyclic ring, or (C4-C6)-cycloalkenyl which is condensed at one side of the ring to a 4- to 6-membered saturated or unsaturated carbocyclic ring;
where each of the 4 lastmentioned radicals is unsubstituted or substituted by one or more radicals selected from the group consisting of:
halogen, hydroxyl, cyano, (C1-C4)-alkyl, (C1-C4)-haloalkyl, (C1-C4)-alkoxy, (C1-C4)-haloalkoxy, (C1-C4)-alkylthio, (C1-C4)-alkylamino, di[(C1-C4)-alkyl]-amino, [(C1-C4)-alkoxy]-carbonyl, and [(C1-C4)-haloalkoxy]-carbonyl;
(C3-C6)-cycloalkyl, which is unsubstituted or substituted by one or more radicals selected from the group consisting of halogen, (C1-C4)-alkyl and (C1-C4)-haloalkyl;
phenyl, which is unsubstituted or substituted by one or more radicals selected from the group consisting of halogen, (C1-C4)-alkyl, (C1-C4)-haloalkyl, (C1-C4)-alkoxy, (C1-C4)-haloalkoxy and (C1-C4)-alkylthio; and
heterocyclyl, which is unsubstituted or substituted by one or more radicals selected from the group consisting of halogen, (C1-C4)-alkyl, (C1-C4)-haloalkyl, (C1-C4)-alkoxy, (C1-C4)-haloalkoxy, (C1-C4)-alkylthio and oxo.

6. The compound as claimed in claim 1;
wherein R3 is:
hydrogen, (C1-C10)-alkyl, (C2-C10)-alkenyl, or (C2-C10)-alkynyl;
where each of the 3 lastmentioned radicals is unsubstituted or substituted by one or more radicals selected from the group consisting of halogen, hydroxyl, cyano, (C1-C4)-alkoxy, (C1-C4)-haloalkoxy, (C1-C4)-alkylthio, (C1-C4)-alkylamino, di[(C1-C4)-alkyl]-amino, [(C1-C4)-alkoxy]-carbonyl, and [(C1-C4)-haloalkoxy]-carbonyl; or

(C3-C6)-cycloalkyl or (C3-C6)-cycloalkyl which is condensed at one side of the ring to a 4- to 6-membered saturated or unsaturated carbocyclic ring;
where each of the 2 lastmentioned radicals is unsubstituted or substituted by one or more radicals selected from the group consisting of (C1-C4)-alkyl; and


wherein R4 is:
(C1-C10)-alkyl, (C2-C10)-alkenyl, or (C2-C10)-alkynyl;
where each of the 3 lastmentioned radicals is unsubstituted or substituted by one or more radicals selected from the group consisting of halogen, hydroxyl, cyano, (C1-C4)-alkoxy, (C1-C4)-haloalkoxy, (C1-C4)-alkylthio, (C1-C4)-alkylamino, di[(C1-C4)-alkyl]-amino, [(C1-C4)-alkoxy]-carbonyl, and [(C1-C4)-haloalkoxy]-carbonyl; or

(C3-C6)-cycloalkyl or (C3-C6)-cycloalkyl which is condensed at one side of the ring to a 4- to 6-membered saturated or unsaturated carbocyclic ring;
where each of the 2 lastmentioned radicals is unsubstituted or substituted by one or more radicals selected from the group consisting of (C1-C4)-alkyl.

7. The compound as claimed in claim 1;
wherein R3 is hydrogen, (C1-C10)-alkyl, (C2-C10)-alkenyl, or (C2-C10)-alkynyl;
where each of the 3 lastmentioned radicals is unsubstituted or substituted by one or more radicals selected from the group consisting of (C1-C4)-alkoxy, (C1-C4)-haloalkoxy, (C1-C4)-alkylthio, and [(C1-C4)-alkoxy]-carbonyl; and

wherein R4 is (C1-C10)-alkyl, (C2-C10)-alkenyl, or (C2-C10)-alkynyl;
where each of the 3 lastmentioned radicals is unsubstituted or substituted by one or more radicals selected from the group consisting of (C1-C4)-alkoxy, (C1-C4)-haloalkoxy, (C1-C4)-alkylthio, and [(C1-C4)-alkoxy]-carbonyl.

8. The compound as claimed in claim 1;
wherein R1 is CF3, CF2Cl, CF2H, CF2CF3, CF2CF2H, CF2CF2Cl, CF2CF2CF3, or C(CH3)2F; and
wherein R2 is hydrogen or halogen.

9. The compound as claimed in claim 1;
wherein R1 is a (C1-C6)-haloalkyl radical;
wherein R2 is halogen;
wherein R3 is hydrogen; and
wherein R4 is hydrogen.

10. The compound as claimed in claim 1;
wherein R1 is a radical of the formula CF2Cl, CF2H, CF2CF3, CF2CF2H, CF2CF2Cl, CFClCF3, CFHCF3, CF(CF3)2, CH(CF3)2, CF2CF2CF3, or C(CH3)2F;
wherein R2 is hydrogen;
wherein R3 is hydrogen; and
wherein R4 is hydrogen.

11. A method for protecting useful plants against phytotoxic side effects of agrochemicals, the method comprising:
applying an effective amount of one or more compounds as defined in claim 1 before, after, or simultaneously with the agrochemicals to the plants, parts of the plants, the plant seeds, or seed of the plants.

12. The method as claimed in claim 11;
wherein one or more compounds of the formula (I) or salts thereof are used together with one or more agrochemicals which, applied on their own, cause damage to the useful plants, optionally in the presence of formulation auxiliaries.

13. The method as claimed in claim 11;
wherein the application is by the post-emergence method.

14. The method as claimed in claim 11;
wherein the application of the compound of the formula (I) or a salt thereof is by treating the plant seeds or seed of the plants.

15. The method as claimed in claim 11;
wherein the application is by the pre-emergence method.

16. A method for the selective control of harmful plants in crops of useful plants, the method comprising:
applying an effective amount of one or more compounds of the formula (I) or salts thereof as defined in claim 1 before, after, or simultaneously with one or more herbicides to the plants, parts of plants, plant seeds, or seed of the plants.

17. The method as claimed in claim 16, further comprising:
treating the seed of the plants with one or more compounds of the formula (I) or salts thereof and applying the herbicide after sowing by the pre-emergence method or by the post-emergence method.