# Patent

## Title
N-phenyl-4-(4-pyridyl)-2-pyrimidineamine derivatives

## Abstract

The present invention relates to a method of protecting plants against attack or infestation by phytopathogenic organisms, such as nematodes or especially microorganisms, preferably fungi, bacteria and viruses, or combinations of two or more of these organisms, by applying at least one compound of the formula (I): wherein n is 0 or 1, R1 is halogen, alkoxy, haloalkyl, haloalkoxy or alkyl, R2 is hydrogen, halogen, alkyl, haloalkyl, alkoxy or haloalkoxy, each of R3, R4 and R5 is, independently of the others, hydrogen, lower alkyl or halogen, and R6 is as defined in claim 1. The invention also relates to new compounds of formula (I), their preparation, use and compositions comprising said compound

## Background
This application is a 371 of International Application No. PCT/EP01/06389, filed Jun. 6, 2001, the contents of which are incorporated herein by reference.
The present invention relates to a method of protecting plants against attack or infestation by phytopathogenic organisms, such as nematodes or especially microorganisms, preferably fungi, bacteria and viruses, or combinations of two or more of these organisms, by administering an N-phenyl-4-(4-pyridyl)-2-pyrimidineamine derivative as specified hereinafter to a part and/or to the site of a plant, the use of said derivative for protecting plants against said organisms and compositions comprising said derivative. It further relates to novel N-phenyl-4-(4-pyridyl)-2-pyrimidineamine derivatives, their preparation, their use as mentioned above and compositions comprising them.
Certain N-phenyl-4-(4-pyridyl)-2-pyrimidineamine derivatives have already been described in PCT applications WO 95/09851 and WO 95/09853, useful for example for treating tumours.
Surprisingly, it has now been found that these and the additional new N-phenyl-4-(4-pyridyl)-2-pyrimidineamine are effective in plant protection and related areas, showing advantageous properties in the treatment of plant diseases caused by organisms.
The N-phenyl-4-(4-pyridyl)-2-pyrimidineamine derivatives to be used according to the invention are those of the formula I,




wherein

n is 0 or 1,
R1 is halogen, alkoxy, haloalkyl, haloalkoxy or alkyl,
R2 is hydrogen, halogen, alkyl, haloalkyl, alkoxy or haloalkoxy,
each of R3, R4 and R5 is, independently of the others, hydrogen, lower alkyl or halogen, and
R6 is

    a) hydrazino, that is unsubstituted or one- to threefold substituted by optionally substituted alkyl and/or optionally substituted acyl,
    b) cyclohexylamino, tetrahydro-4H-pyranyl-4-amino, pyrrolidine-3-amino, 2- or 3-tetrahydro-furylamino, all optionally substituted by amino, hydroxy, alkoxy, alkyl or alkoxyalkyl,
    c) piperazinyl that is optionally substituted by amino, amino-lower alkyl, hydroxy, alkoxy, alkyl or alkoxyalkyl,
    d) morpholinyl that is optionally substituted by amino, amino-lower alkyl, hydroxy, alkoxy, alkyl or alkoxyalkyl,
    e) oxazolidinyl that is optionally substituted by amino, amino-lower alkyl, hydroxy, hydroxy-lower alkyl, alkoxy, alkyl or alkoxyalkyl,
    f) thiazolidinyl that is optionally substituted by amino, amino-lower alkyl, hydroxy, hydroxy-lower alkyl, alkoxy, alkyl or alkoxyalkyl,
    g) imidazolidinyl that is optionally substituted by amino, amino-lower alkyl, hydroxy, hydroxy-lower alkyl, alkoxy, alkyl or alkoxyalkyl,
    h) amino or mono- or di-(lower alkyl)amino wherein the lower alkyl moieties are unsubstituted or substituted by one or more (preferably 1 to 3, especially 1 or 2) substitutents independently selected from the group consisting of unsubstituted amino, N-mono- or N,N-di-(lowe ralkyl)-amino, (lower alkoxy)-lower alk-oxy, lower alkoxycarbonylamino, hydroxy-lower alkoxycarbonylamino, lower alkoxy-lower alkoxycarbonylamino, morpholinyl, hydroxy-lower alkylamino, cyano, halogen, oxo, hydroximino, alkoximino, optionally substituted hydrazono, lower alkenyl, lower alkynyl, guanidyl, lower alkanoylamino, hydroxy-lower alkanoylamino, lower alkoxy-lower alkanoylamino, halo-lower alkanoylamino, lower alkylaminocarbonylamino, hydroxy-lower alkylaminocarbonylamino, lower alkoxy-lower alkylaminocarbonylamino, amidino, di-lower-alkylamino-cyclohexyl, carboxy, lower alkoxycarbonyl, hydroxy-lower alkoxycarbonyl, lower alkoxy-lower alkoxycarbonyl, lower alkylcarbonyldioxy (=lower alkoxycarbonyloxy), hydroxy-lower alkoxycarbonyloxy, lower alkoxy-lower alkoxycarbonyloxy, lower alkanoyloxy, halo-lower alkanoyloxy, hydroxy-lower alkanoyloxy, lower alkoxy-lower alkanoyloxy, carbamoyl, N-mono- or N,N-di-lower alkylcarbamoyl, N-(hydroxy-lower alkyl)carbamoyl, N-lower alkyl-N-hydroxy-lower alkylcarbamoyl, N,N-di-(hydroxy-lower alkyl)-carbamoyl, N-hydroxy-carbamoyl, hydroxy, lower alkoxy, lower alkenyloxy, lower alkinyloxy, lower haloalkoxy, lower alkylthio, lower alkylsulfoxyl, lower alkylsulfonyl, lower alkoxysilyl, 4-tetrahydro-4H-pyranyl, 3-pyrrolidinyl, 2- or 3-tetrahydrofuryl, 2- or 3-dihydrofuryl, piperazinyl, lower alkanoyl-piperazinyl (including formylpiperazinyl), optionally substituted heteroaryl and optionally substituted heteroaryloxy
    i) optionally substituted alkanoylamino, optionally substituted alkenoylamino, optionally substituted alkynoylamino, optionally substituted mono- or di-alkylaminocarbonylamino, optionally substituted alkoxycarbonylamino, optionally substituted mono- or di-alkylaminosulfonylamino, optionally substituted mono- or di-alkylaminosulfoxylamino,
    j) N-(optionally substituted alkyl)-N-(optionally substituted lower alkanoyl)-amino,
    k) N-(optionally substituted alkyl)-N-(optionally substituted alkoxycarbonyl)-amino,
    l) N-(optionally substituted alkyl)-N-(N′,N′-mono- or di-[optionally substituted alkyl]-aminocarbonyl)-amino, or
    m) N═C(R7,R8) wherein R7 is hydrogen, alkyl, amino, mono- or di-alkylamino and R8 is amino, mono- or dialkylamino or wherein R7 and R8, together with the binding carbon atom, form a saturated five- to seven-membered ring with 0, 1 or 2 ring nitrogen atoms that is optionally substituted by one or more substituents, preferably 1 to 3 substituents, especially lower alkyl;

or a salt thereof.



The general symbols and expressions used above preferably are defined as below:
Halogen is fluorine, bromine, iodine or preferably chlorine.
Alkoxy is preferably C1–C16alkoxy, more preferably C1–C8alkoxy, especially lower alkoxy, and is linear or branched. Lower alkoxy is preferably methoxy or ethoxy.
Haloalkyl is preferably C1–C16alkyl, more preferably C1–C8alkyl, especially lower alkyl, that is linear or branched and is substituted by one or more, for example in the case of halo-ethyl up to six, halogen atoms, especially fluorine. Preferred is trifluoromethyl or 2,2,2-trifluoroethyl.
Haloalkoxy is preferably C1–C16alkoxy, more preferably C1–C8alkoxy, especially lower alkoxy, that is linear or branched and that is substituted by one or more, for example in the case of halo-ethyl up to five, halogen atoms, especially fluorine; trifluoromethoxy and 1,1,2,2-tetrafluoroethoxy are especially preferred.
Alkyl—as a group per se se and as a structural element of other groups and compounds, such as alkylamino, alkanoylamino, alkanoyloxy, alkylthio, alkylsulfoxyl, alkylsulfonyl—is preferably C0–C16alkyl, more preferably C1–C8alkyl, especially lower alkyl, and is linear i.e. methyl, ethyl, propyl, butyl, pentyl or hexyl, or branched one or more times, e.g. isopropyl, isobutyl, sec.-butyl, tert.-butyl, isopentyl, neopentyl or isohexyl. Lower alkyl is preferably methyl or ethyl.
Optionally substituted means that the respective moiety is unsubstituted (=bearing only hydrogen instead of a substitutent) or substituted by one or more, especially 1 to 3, substituents independently selected from the group consisting of amino, N-mono- or N,N-di-(lower alkyl)-amino, (lower alkoxy)-lower alk-oxy, lower alkoxycarbonylamino, hydroxy-lower alkoxycarbonylamino, lower alkoxy-lower alkoxycarbonylamino, morpholinyl, hydroxy-lower alkylamino, cyano, halogen, oxo bound to a carbon that is not directly bound to a heteroatom, hydroximino, alkoximino, optionally substituted hydrazono, lower alkenyl, lower alkynyl, guanidyl, lower alkanoylamino, hydroxy-lower alkanoylamino, lower alkoxy-lower alkanoylamino, halo-lower alkanoylamino, lower alkylaminocarbonylamino, hydroxy-lower alkylaminocarbonylamino, lower alkoxy-lower alkylaminocarbonylamino, amidino, di-lower-alkylamino-cyclohexyl, carboxy, lower alkoxycarbonyl, hydroxy-lower alkoxycarbonyl, lower alkoxy-lower alkoxycarbonyl, lower alkylcarbonyldioxy (=lower alkoxycarbonyloxy), hydroxy-lower alkoxycarbonyloxy, lower alkoxy-lower alkoxycarbonyloxy, lower alkanoyloxy, halo-lower alkanoyloxy, hydroxy-lower alkanoyloxy, lower alkoxy-lower alkanoyloxy, carbamoyl, N-mono- or N,N-di-lower alkylcarbamoyl, N-(hydroxy-lower alkyl)carbamoyl, N-lower alkyl-N-hydroxy-lower alkyl-carbamoyl, N,N-di-(hydroxy-lower alkyl)-carbamoyl, N-hydroxy-carbamoyl, hydroxy, lower alkoxy, lower alkenyloxy, lower alkinyloxy, lower haloalkoxy, lower alkylthio, lower alkylsulfinyl, lower alkylsulfonyl, lower alkoxysilyl, 4-tetrahydro-4H-pyranyl, 3-pyrrolidinyl, 2- or 3-tetrahydrofuryl, 2- or 3-dihydrofuryl, piperazinyl, lower alkanoyl-piperazinyl (including formylpiperazinyl), optionally substituted heteroaryl and optionally substituted heteroaryloxy (with the proviso that in the case of optionally substituted heteroaryl and optionally substituted heteroaryloxy a heteroaryl substituent is preferably not substituted by substituted heteroaryloxy). Preferred substituents are lower alkoxy, hydroxy and/or halogen, if not mentioned otherwise.
For example, substituents in the optionally substituted alkyl group are one or more substitutents independently selected from the group of substituents mentioned in the last paragraph.
Alkenyl—as a group per se se and as a structural element of other groups and compounds, such as alkenoylamino—is preferably C2–C16-, more preferably C2–C8-, especially C3–C8-, very especially C3–C7-, for example C3–C4-alkenyl, and is either straight-chained, for example vinyl, 1-methylvinyl, allyl, 1-butenyl or 2-hexenyl, or branched, for example isopropenyl. Preferably (for reasons of chemical stability) the C-atoms in alkenyl that are bonded to a heteroatom (e.g. N, O or S) do not carry the double bond.
Alkynyl—as a group per se and as a structural element of other groups and compounds, such as alkynoylamino—is preferably C2–C16-, more preferably C2–C8-, especially C3–C8-, very especially C3–C7-, for example C3–C4-alkenyl, and is either straight-chained, for example propargyl, 2-butynyl or 5-hexynyl, or branched, for example 2-ethynylpropyl or 2-propargyl-isopropyl. Preferably (for reasons of chemical stability) the C-atoms in alkynyl that are bonded to a heteroatom (e.g. N, O or S) do not carry the triple bond.
One—to threefold substituted hydrazino preferably carries one to three substituents independently selected from the group consisting of alkyl, haloalkyl, such as trifluoromethyl, hydroxyalkyl, such as 2-hydroxyethyl, hydroxymethyl or 1-hydroxymethyl-n-propyl, alkoxyalkyl, such as 2-methoxyethyl, ethoxymethyl or 1-methoxymethyl-n-propyl, and acyl. Optionally substitued alkyl is preferably as defined above.
Acyl is preferably C1–C16alkanoyl, more preferably lower alkanoyl, and is linear or branched. Lower alkanoyl is preferably formyl, acetyl or in a broader sense of the invention propionyl or butyryl.
Substitutents in the optionally substituted acyl group are preferably one or more substituents independently selected from halogen (more preferably fluorine), hydroxy or alkoxy (more preferably methoxy or ethoxy), e.g. in trifluoroacetyl or pentafluoropropionyl.
Substituted hydrazinyl is preferably hydroxy-lower alkyl-hydrazino; 2-hydroxyethyl is an especially preferred substituent of the hydrazino group.
Cyclohexyl-amino substituted by amino is preferably 2- or 4-amino-cyclohexyl-amino.
Piperazinyl is preferably 1-piperazinyl. As substituted piperazinyl, piperazinyl substituted by amino-lower alkyl is preferred, especially 4-(2-amino-ethyl)-piperazin-1-yl.
Morpholinyl is preferably 4-morpholinyl (=morpholino). Lower alkylamino R6 substituted by morpholinyl is preferably 2-morpholin-4-yl-ethylamino. Substituted morpholinyl is preferably 3-alkyl- or 3,5-dialkylmorpholino, more preferably 3-methyl- or 3,5-dimethylmorpholino.
Formyl-piperazinyl is preferably 4-formyl-piperazinyl.
Lower alkyl that is substituted by unsubstituted mono- or di-(lower alkyl)-amino in mono- or di-(lower alkyl)-amino R6 with one or (if two are present) both moieties substituted is preferably lower alkyl that is substituted by N-mono- or N,N-di-(lower alkyl)amino, preferably dimethylamino; preferred is lower alkylamino that is substituted by N-mono- or N,N-di-(lower alkyl)amino, most preferably 3-(dimethylamino)-1-methyl-n-propylamino.
Lower alkyl substituted by amino in mono- or di-(lower alkyl)-amino R6 with one or (if two are present) both lower alkyl moieties substituted is preferably lower alkyl substituted by one or two amino groups; preferred is mono-lower alkyl that is substituted by one or more, especially 1 or 2, amino groups, especially 2-amino-ethylamino or 3-amino-n-propylamino.
(Lower alkoxy)-lower alkoxy as substituent of a substituted lower alkyl moiety of mono- or di-(lower alkyl)-amino is preferably (methoxy)-methoxy.
A preferred di-(lower alkyl)amino R6 wherein the lower alkyl moieties are substituted by (lower alkoxy)-lower alkoxy and lower alkoxy is N-(methoxymethyl)-N-{2-[(methoxy)-methoxy]-1-methyl-ethyl}-amino.
Hydroxy-lower alkylamino is preferably hydroxy-lower alkyl that carries one or more, especially one or two, hydroxy groups, more preferably 2-hydroxy-ethylamino. Lower alkylamino substituted by hydroxy-lower alkylamino is preferably 3-(2-hydroxy-ethyl-amino)-prop-1-yl-amino
Oxo is not bonded to a carbon atom that is bound to a heteroatom, such as nitrogen, sulfur or oxygen, in order to avoid overlap with acyl substituents.
Lower alkylamino-carbonylamino is preferably methylamino-carbonyl-amino.
Di-lower alkylamino is preferably dimethylamino.
Alkoximino is preferably C1–C16-, more preferably C1–C8-, most preferably lower alkoximino.
Optionally substituted hydrazono is preferably hydrazono or hydrazono substituted with one of the substituents defined above for “optionally substituted”. Hydrazono or N-lower alkylhydrazono is preferred.
Lower alkyl substituted by hydroxy in mono- or di-(lower alkyl)-amino R6 with one or (if two are present) both lower alkyl moieties substituted is preferably lower alkylamino that carries one or more hydroxy substituents, especially 1 or 2 hydroxy substituents, preferred is mono-lower alkyl-amino that is substituted by one or two hydroxy groups, especially 2- or 3-hydroxy-n-propylamino, 1,1-dimethyl-3-hydroxy-n-propylamino, 1-n-propyl-2-hydroxy-ethylamino, 1,1-dimethyl-2-hydroxy-ethylamino, 1-ethyl-2-hydroxy-ethylamino, 2-hydroxy-1-(hydroxy-methyl)-ethylamino, 2-hydroxy-1-methyl-ethylamino or 2-hydroxy-1-(sec-butyl)-ethylamino.
Lower alkyl substituted by lower alkoxy in mono- or di-lower alkylamino R6 with one or (if two are present) both lower alkyl moieties substituted is preferably lower alkyl that is substituted by one or more, especially 1 or 2, lower alkoxy groups; preferred is mono-lower alkylamino R6 wherein the lower alkyl moieties are substituted by lower alkoxy, especially 2-methoxy-ethylamino, 1-ethyl-2-methoxy-ethylamino, 2-methoxy-1-methyl-ethylamino, 2-methoxy-2-methyl-ethylamino, 1,1-dimethyl-2-methoxy-ethylamino, 1,1-dimethyl-3-methoxy-n-propylamino or 3-methoxy-propylamino.
Lower alkyl substituted by carboxy in mono- or di-lower alkylamino R6 with one or (if two are present) both lower alkyl moieties substituted is preferably carboxymethyl.
Lower alkoxycarbonyl-amino is preferably ethoxycarbonyl-amino. Preferred is mono-lower alkylamino R6 that is substituted by lower alkoxycarbonylamino, especially 3-[N-(ethoxycarbonyl)-amino]-n-propylamino.
Lower alkyl substituted by cyano, guanidyl, lower alkanoyl-amino, lower alkylaminocarbonylamino, amidino, di-lower alkylamino-cyclohexyl, lower alkoxycarbonyl, carbamoyl, N-hydroxy-carbamoyl, piperazinyl, lower alkanoyl-piperazinyl, formylpiperazinyl, tetrahydro-4H-pyranyl-4-amino, pyrrolidine-3-amino, 2- or 3-tetrahydrofurylamino, optionally substituted heteroaryl or optionally substituted heteroaryloxy is preferably di- or tri-methyleneamino substituted by those substituents, the substituents preferably being in the ω-position. The same holds true for other substitutents of lower alkyl in substituted mono- or di-lower alkylamino that are not defined in more detail.
Heteroaryl (in the term heteroaryl and heteroaryloxy) is a cyclic aromatic group with one or two rings with a total of 5 to 12 ring members, 1 to 3 members of which are hetero atoms, preferably selected from the group consisting of oxygen, sulphur and nitrogen. 1 to 2 benzene rings may be condensed onto the heterocycle, whereby the binding to the residual molecule takes place either via the hetero or the benzene moiety. Preferably, heteroaryl is benzimidazolyl, benzisoxazolyl, benzisothiazolyl, benzocoumarinyl, benzofuryl, benzothiadiazolyl, benzothiazolyl, benzothienyl, benzoxazolyl, benzoxdiazolyl, quinazolinyl, quinolyl, quinoxalinyl, carbazolyl, dihydrobenzofuryl, furyl (especially 2- or 3-furyl), imidazolyl (especially 1-imidazolyl), indazolyl, indolyl, isoquinolinyl, isothiazolyl, isoxazolyl, methylenedioxyphenyl, ethylenedioxyphenyl, naphthyridinyl, oxazolyl, phenanthridinyl, phthalazinyl, pteridinyl, purinyl, pyrazinyl, pyrazolyl, pyridazinyl, pyrazolo[3,4-b]pyridyl, pyridyl (especially 2-, 3- or 4-pyridyl), pyrimidyl, pyrrolyl, tetrazolyl (especially tetrazol-1-yl), oxadiazolyl, thiadiazolyl, thiazolyl (especially 2-, 4- or 5-thiazolyl), thienyl (especially 2- or 3-thienyl), triazinyl (especially 1,3,5-triazinyl) and triazolyl (especially 1,2,4-triazol-1-yl). Furyl, pyridyl, imidazolyl and triazolyl are preferred.
The heteroaryl and heteroryloxy moiety may be substituted by one or more, preferably one to three identical or different substitutents selected from the group comprising halogen, C1–C6-alkyl, C3–C6-cycloalkyl, halogen-C1–C6-alkyl, hydroxy, C1–C6-alkoxy, halogen-C1–C6-alkoxy, C1–C6-alkylthio, halogen-C1–C6-alkylthio, C1–C6-alkyll, halogen-C1–C6-alkyll, C1–C6-alkylsulfinyl, halogen-C1–C6-alkylsulfinyl, C1–C6-alkylsulfonyl, halogen-C1–C6-alkylsulfonyl, C1–C6-alkyl-carbonyl, halogen-C1–C6-alkylcarbonyl, carboxyl, C1–C6-alkoxycarbonyl, halogen-C1–C6-alkoxycarbonyl, aminocarbonyl, C1–C6-alkylaminocarbonyl, di-(C1–C6-alkyl)-aminocarbonyl, whereby the alkyl groups may be identical or different, amino, C1–C6-alkylamino, di-(C1–C6-alkyl)-amino, NO2, CN, C2–C6-alkenyl or C2–C6-alkynyl.
Alkanoylamino is preferably C1–C16alkanoylamino, more preferably C1–C6-alkanoylamino, most preferably lower alkanoylamino, especially formylamino, acetylamino, propionylamino, butanoylamino and pentanoylamino. Preferred substituents of the alkanoyl group are one or more, especially 1 to five, substituents independently selected from the group consisting of fluorine, hydroxy and methoxy. Especially preferred are trifluoroacetylamino and 2-hydroxy-propionylamino.
A five- to seven-membered ring with 0, 1 or 2 ring nitrogen atoms formed from R7 and R8 together with the binding carbon atom preferably has 2 ring nitrogen atoms that are immediately adjacent (=bound) to the binding carbon atom, for example forming an imidazolidin-2-ylidene, tetrahydropyrimidin-2-ylidene or hexahydro-1,3-diazepin-2-ylidene moiety, and is optionally substituted, especially unsubstituted or substituted by one to three lower alkyl moieties, especially methyl, etyhl, propyl or isopropyl, which may be bound to carbon or nitrogen ring atoms.
As substituents R6, those mentioned specifically in Table A given below and/or in the Examples are especially preferred and can be combined with the other moieties R1 to R5 in formula I.
Within the scope of this text, the term “lower” denotes radicals having up to and including 7, preferably up to and including 4, carbon atoms. Unless otherwise indicated in the context concerned, lower alkyl is preferably methyl or ethyl. In the case of alkenyl or alkinyl, “lower” means C2–C7-, more preferably C3–C7-, such as C3–C4-alkenyl or -alkinyl, and the double- or triple bond preferably does not start from a heteroatom, especially S, N or O, most especially one carrying a hydrogen, such as NH, OH or SH.
The compounds of formula I can form acid addition salts, for example with inorganic acids, such as hydrochloric acid, sulfuric acid or a phosphoric acid, or with suitable organic carboxylic or sulfonic acids, for example aliphatic mono- or di-carboxylic acids, such as trifluoroacetic acid, acetic acid, propionic acid, glycolic acid, succinic acid, maleic acid, fumaric acid, hydroxymaleic acid, malic acid, tartaric acid, citric acid, oxalic acid or amino acids, such as arginine or lysine, aromatic carboxylic acids, such as benzoic acid, 2-phenoxy-benzoic acid, 2-acetoxy-benzoic acid, salicylic acid, 4-aminosalicylic acid, aromatic-aliphatic carboxylic acids, such as mandelic acid or cinnamic acid, heteroaromatic carboxylic acids, such as nicotinic acid or isonicotinic acid, aliphatic sulfonic acids, such as methane-, ethane- or 2-hydroxy-ethane-sulfonic acid, or aromatic sulfonic acids, for example benzene-, p-toluene- or naphthalene-2-sulfonic acid. Mono, di- or, if other basic groups, such as amino or guanidyl groups, are present in the radical R6, poly-acid addition salts can be formed.
Compounds of formula I having acidic groups, for example a free carboxy group in the radical R6, can form metal or ammonium salts, such as alkali metal or alkaline earth metal salts, for example sodium, potassium, magnesium or calcium salts, or ammonium salts with ammonia or suitable organic amines, such as tertiary monoamines, for example triethylamine or tri(2-hydroxyethyl)amine, or heterocyclic bases, for example N-ethyl-piperidine or N,N′-dimethyl-piperazine.
Compounds of formula I that possess both acidic and basic groups can form internal salts.
The pyridine-N-oxides of formula I (n=1) can form acid addition salts with strong acids, such as hydrochloric acid, nitric acid, phosphoric acid or sulfonic acids, such as benzene-sulfonic acid. The compounds of formula I with n=1 are new and thus form an especially preferred embodiment of the invention, as their use and process of manufacture.
Formula I is meant to include all the possible isomeric forms, as well as mixtures, e.g. racemic mixtures, and any [E/Z] mixtures.
In view of the close relationship between the compounds of formula I in free form and in the form of their salts, including also salts that can be used as intermediates, for example in the purification of the compounds of formula I or in order to identify those compounds, herein-before and hereinafter any reference to the (free) compounds is to be understood as including also the corresponding salts, where appropriate and expedient.
Where hereinbefore and hereinafter reference is made that “compounds can be used according to the invention” or a “method for applying a compound of formula I” or to “compounds to be used according to the invention, this refers to the fact that the invention relates to any one or more of

    (i) the use of a compound of the formula I, or a salt thereof, for protection of a plant against attack by a phytopathogenic organism or the treatment of a plant infested by a phytopathogenic organism, said use comprising the administration of a compound of the formula I or a salt thereof, or a composition comprising said compound or salt and a carrier material acceptable for agricultural purposes, to any one or more selected from the group consisting of a plant, a part of a plant, seeds and the locus of a plant;
    (ii) a method of protecting a plant against attack by a phytopathogenic organism and/or the treatment of a plant infested by a phytopathogenic organism, said method comprising administering a compound of the formula I or a salt thereof, or a composition comprising said compound or salt and a carrier material acceptable for agricultural purposes, to any one or more selected from the group consisting of a plant, a part of a plant, seeds and the locus of a plant, preferably if in need of such treatment;
    (iii) a process for protecting a plant against attack by a phytopathogenic organism and/or the treatment of a plant infested by a phytopathogenic organism, said process comprising administering a compound of the formula I or a salt thereof, or a composition comprising said compound or salt and a carrier material acceptable for agricultural purposes, to any one or more selected from the group consisting of a plant, a part of a plant, seeds and the locus of a plant; and/or
    (iv) a composition (useful) for protecting a plant against attack by a phytopathogenic organisms and/or the treatment of a plant infested by a phytopathogenic organism, said composition comprising a compound of the formula I or a salt thereof and a carrier material acceptable for agricultural purposes.
    Any of these uses, methods, processes or compositions is meant as preferred part of the invention where the respective reference given above in citation marks is/are made.


In the preferred or more specific embodiments of the invention given above and below, the definitions given above can be used instead of more general terms, thus leading to preferred embodiments of the invention.
The compounds of formula I may be used preventatively and/or curatively in the agrarian sector and related fields as active ingredients for controlling plant pests. The active ingredients of formula I according to the invention are notable for their good activity even at low concentrations, for their good plant tolerance and for their environmentally friendly nature. They have very advantageous, especially systemic, properties and may be used to protect a plurality of cultivated plants. Using the active ingredients of formula I on plants or plant parts (fruit, flowers, leaves, stems, tubers, roots) of various crops, the pests appearing can be controlled or destroyed, whereby the parts of plants which grow later also remain protected, e.g. from phytopathogenic micro-organisms.
The compounds of formula I may additionally be used as a dressing to treat seeds (fruits, tubers, corms) and plant cuttings to protect against fungal infections and against phytopathogenic fungi occurring in the soil.
The compounds of formula I are effective for example against the following classes of related phytopathogenic fungi: Fungi imperfecti (e.g. Botrytis, Pyricularia, Helminthosporium, Fusarium, Septoria, Cercospora and Altemaria); Basidiomycetes (e.g. Rhizoctonia, Hemileia, Puccinia); Ascomycetes (e.g. Venturia and Erysiphe, Podosphaera, Monilinia, Uncinula) and Oomycetes (e.g. Phytophthora, Pythium, Plasmopara).
Target crops for the plant-protecting usage in terms of the invention are for example the following plant cultivars: cereals (wheat, barley, rye, oats, rice, maize, sorghum and related species); beet (sugar beet and fodder beet); pome, stone and berry fruit (apples, pears, plums, peaches, almonds, cherries, strawberries, raspberries and blackberries); legumes (beans, lentils, peas, soya); oil crops (rape, mustard, poppy, olives, sunflowers, coconut, castor oil, cocoa, peanut); cucumber plants (squashes, cucumber, melons); citrus fruits (oranges, lemons, grapefruits, mandarines); vegetables (spinach, lettuce, asparagus, cabbage varieties, carrots, onions, tomatoes, potatoes, paprika); laurels (avocado, cinnamonium, camphor) and plants such as tobacco, nuts, coffee, aubergines, sugar cane, tea, pepper, vines, hops, bananas and natural rubber plants, as well as ornamental plants.
Further areas of application for the active ingredients according to the invention are the protection of stores and material, where the storage matter is protected against putrescence and mould.
The compounds of formula I are used in unchanged form or preferably together with customary excipients in formulation techniques. To this end, they are conveniently processed in known manner e.g. into emulsion concentrates, coatable pastes, directly sprayable or diluable solutions, diluted emulsions, wettable powders, soluble powders, dusts or granules, e.g. by encapsulation into for example polymeric materials. As with the type of medium, the application processes, such as spraying, atomizing, dusting, scattering, coating or pouring are similarly chosen according to the desired aims and the prevailing conditions.
Suitable substrates and additives may be solid or liquid and are useful substances in formulation techniques, e.g. natural or regenerated mineral substances, dissolving aids, dispersants, wetting agents, tackifiers, thickeners, binding agents or fertilizers.
The compounds of formula I may be mixed with further active ingredients, e.g. fertilizers, ingredients providing trace elements or other plant protection compositions, especially further fungicides. In doing so, unexpected synergistic effects may occur.
Preferred additions to the mixture are:

    Azoles, such as azaconazole, bitertanol, bromuconazole, cyproconazole, difenoconazole, diniconazole, epoxiconazole, fenbuconazole, fluquinconazole, flusilazole, flutriafol, hexaconazole, imazalil, imibenconazole, ipconazole, metconazole, myclobutanil, pefurazoate, penconazole, pyrifenox, prochloraz, propiconazole, tebuconazole, tetraconazole, triadimefon, triadimenol, triflumizole, triticonazole;
    pyrimidinyl carbinoles, such as ancymidol, fenarimol, nuarimol;
    2-amino-pyrimidines, such as bupirimate, dimethirimol, ethirimol;
    morpholines, such as dodemorph, fenpropidine, fenpropimorph, spiroxamin, tridemorph;
    anilinopyrimidines, such as cyprodinil, mepanipyrim, pyrimethanil;
    pyrroles, such as fenpiclonil, fludioxonil;
    phenylamides, such as benalaxyl, furalaxyl, metalaxyl, r-metalaxyl, ofurace, oxadixyl;
    benzimidazoles, such as benomyl, carbendazim, debacarb, fuberidazole, thiabendazole;
    dicarboximides, such as chlozolinate, dichlozoline, iprodione, myclozoline, procymidone, vinclozoline;
    carboxamides, such as carboxin, fenfuram, flutolanil, mepronil, oxycarboxin, thifluzamide;
    guanidines, such as guazatine, dodine, iminoctadine;
    strobilurines, such as azoxystrobin, kresoxim-methyl, metominostrobin, SSF-129, trifloxystrobin;
    dithiocarbamates, such as ferbam, mancozeb, maneb, metiram, propineb, thiram, zineb, ziram;
    N-halomethylthio, such as captafol, captan, dichlofluanid, fluoromides, folpet, tolyfluanid;
    Cu compounds, such as Bordeaux mixture, copper hydroxide, copper oxychloride, copper sulfate, cuprous oxide, mancopper, oxine-copper;
    nitrophenol-derivatives, such as dinocap, nitrothal-isopropyl;
    organo-p-derivatives, such as edifenphos, iprobenphos, isoprothiolane, phosdiphen, pyrazophos, tolclofos-methyl;

Various others, such as acibenzolar-S-methyl, anilazine, blasticidin-S, chinomethionate, chloroneb, chlorothalonil, cymoxanil, dichlone, diclomezine, dicloran, diethofencarb, dimethomorph, dithianon, etridiazole, famoxadone, fenamidone, fentin, ferimzone, fluazinam, flusulfamide, fenhexamid, fosetyl-aluminium, hymexazol, iprovalicarb, IKF-916, kasugamycin, methasulfocarb, pencycuron, phthalide, polyoxins, probenazole, propamocarb, pyroquilon, quinoxyfen, quintozene, sulfur, triazoxide, tricyclazole, triforine, validamycin.



One preferred method of application of an active ingredient of formula I or of an agrochemical composition containing at least one of these active ingredients is foliar application. The frequency and amount of application depend on the severity of the attack by the pathogen in question. However, the active ingredients I may also reach the plants through the root system via the soil (systemic action) by drenching the locus of the plant with a liquid preparation or by incorporating the substances into the soil in solid form, e.g. in the form of granules (soil application). In rice cultivations, these granules may be dispensed over the flooded paddy field. The compounds I may however also be applied to seed grain to treat seed material (coating), whereby the grains or tubers are either drenched in a liquid preparation of the active ingredient or coated with a solid preparation.
The compositions are produced in known manner, e.g. by intimately mixing and/or grinding the active ingredient with extenders such as solvents, solid carriers and optionally surfactants.
The agrochemical compositions normally contain 0.1 to 99 percent by weight, especially 0.1 to 95 percent by weight, of active ingredient of formula I, 99.9 to 1 percent by weight, especially 99.8 to 5 percent by weight, of a solid or liquid additive and 0 to 25 percent by weight, especially 0.1 to 25 percent by weight, of a surfactant.
Favourable application rates are in general 1 g to 2 kg of active substance (AS) per hectare (ha), preferably 10 g to 1 kg AS/ha, especially 20 g to 600 g AS/ha. For usage as a seed dressing, it is advantageous to use dosages of 10 mg to 1 g active substance per kg of seed grain.
While concentrated compositions are preferred for commercial usage, the end user normally uses diluted compositions.
The compositions may also contain further additives, such as stabilizers, anti-foaming agents, viscosity regulators, binding agents or tackifiers, as well as fertilizers or other active ingredients to achieve special effects.
Formulations may be prepared analogously to those described for example in WO 97/33890.
In the following, examples for test systems that demonstrate the efficiency of the compounds of the formula I (designated as “active ingredient” or “test compounds”) in plant protection are provided:
BIOLOGICAL ASSAYS
Assay B-1: Effect against Puccinia graminis on Wheat (Brownrust on Wheat)
a) Residual Protective Activity
1 week old wheat plants cv. Arina are treated with the formulated testcompound (0.02% active substance) in a spray chamber. Two days after application wheat plants are inoculated by spraying a spore suspension (1×105 uredospores/ml) on the test plants. After an incubation period of 1 day at 20° C. and 95% relative atmospheric humidity (r. h.) plants are kept for 9 days at 20° C. and 60% r.h.in a greenhouse. The disease incidence is assessed 10 days after inoculation.
b) Systemic Activity
An aqueous spray liquor prepared from the formulated testcompound (0.002% active substance, based on the volume of soil) is poured onto wheat plants 5 days after sowing. Care is taken that the spray liquor does not come into contact with the above-ground parts of the plant. 48 hours later, the plants are inoculated with a spore suspension of the fungus. After an incubation period of 48 hours (95 to 100% r.h. at 20° C.), the plants are placed in a greenhouse at 20° C. 12 days after infection, the disease incidence is evaluated.
Assay B-2: Effect Against Phytophthora infestans on Tomatoes (Late Blight on Potato)
a) Residual Protective Activity
3 week old tomato plants cv. Roter Gnom are treated with the formulated testcompound (0.02% active substance) in a spray chamber. Two day after application the plants are inoculated by spraying a sporangia suspension (2×104 sporangia/ml) on the test plants. After an incubation period of 4 days at 18° C. and 95% r. h. in a growth chamber the disease incidence is assessed.
b) Systemic Activity
An aqueous suspension prepared from the formulated test compound (0.002% active substance, based on the volume of soil) is poured onto tomato plants which have been cultivated for three weeks. Care is taken that the spray liquor does not come into contact with the above-ground parts of the plant. 48 hours later, the plants are inoculated with a sporangia suspension of the fungus. Evaluation of the disease incidence takes place 5 days after infection, during which period conditions of 90 to 100% r.h. and 20° C. are maintained.
Assay B-3: Effect Against Phytophthora infestans/Potato (Late Blight on Potato)
5 week old potato plants cv. Bintje are treated with the formulated testcompound (0.02% active substance) in a spray chamber. Two days after application the plants are inoculated by spraying a sporangia suspension (1.4×105 sporangia/ml) on the test plants. After an incubation period of 4 days at 18° C. and 95% r. h. in a growth chamber the disease incidence is assessed.
Assay B-4: Effect Against Plasmopara viticola on Grapevine (Grape Downy Mildew)
5 week old grape seedlings cv. Gutedel are treated with the formulated testcompound (0.02% active substance) in a spray chamber. One day after application grape plants are inoculated by spraying a sporangia suspension (4×104 sporangia/ml) on the lower leaf side of the test plants. After an incubation period of 6 days at 22° C. and 95% r. h. in a greenhouse the disease incidence is assessed.
Assay B-5: Residual Protective Activity Against Venturia inaegualis on Apples (Scab on Apple)
4 week old apple seedlings cv. McIntosh are treated with the formulated testcompound (0.02% active substance) in a spray chamber. One day after application apple plants are inoculated by spraying a spore suspension (4×105 conidia/ml) on the test plants. After an incubation period of 4 days at 21° C. and 95% r. h. the plants are placed for 4 days at 21° C. and 60% r. h. in a greenhouse. After another 4 day incubation period at 21° C. and 95% r. h. the disease incidence is assessed.
Assay B-6: Effect Against Erysiphe graminis on Barley (Powdery Mildew on Barley)
a) Residual Protective Activity
Barley plants of approximately 8 cm height are sprayed to drip point with an aqueous spray liquor prepared from wettable powder of the active ingredient (0.02% active substance), and dusted 3 to 4 hours later with conidia of the fungus. The infected plants are placed in a greenhouse at 22°. 12 days after infection, the fungal attack is evaluated.
b) Systemic Activity
An aqueous spray liquor prepared from the formulated test compound (0.002% active substance, based on the volume of soil) is poured onto barley plants of approximately 8 cm height. Care is taken that the spray liquor does not come into contact with the abouve-ground parts of the plant. 48 hours later, the plants are dusted with conidia of the fungus. The infected plants are placed in a greenhouse at 22° C. 12 days after infection, the disease incidence is evaluated.
Assay B-7: Botrytis cinerea/Grape (Botrytis on Grapes)
5 week old grape seedlings cv. Gutedel are treated with the formulated testcompound (0.02% active substance) in a spray chamber. Two days after application grape plants are inoculated by spraying a spore suspension (1×106 conidia/ml) on the test plants. After an incubation period of 4 days at 21° C. and 95% r. h. in a greenhouse the disease incidence is assessed.
Assay B-8: Effect Against Botrytis cinerea/Tomato (Botrytis on Tomatoes)
4 week old tomato plants cv. Roter Gnom are treated with the formulated testcompound 0.02% active substance) in a spray chamber. Two days after application tomato plants are inoculated by spraying a spore suspension (1×105 conidia/ml) on the test plants. After an incubation period of 4 days at 20° C. and 95% r. h. in a greenhouse the disease incidence is assessed.
Assay B-9: Effect Against Pyricularia oryzae/Rice (Rice Blast)
3 week old rice plants cv. Sasanishiki are treated with the formulated testcompound (0.02% active substance) in a spray chamber. Two days after application rice plants are inoculated by spraying a spore suspension (1×105 conidia/ml) on the test plants. After an incubation period of 6 days at 25° C. and 95% r. h. the disease incidence is assessed.
Assay B-10: Effect Against Pyrenophora teres (Helminthosporium)/Barley (Net Blotch on Barley)
1 week old barley plants cv. Regina are treated with a formulated testcompound (0.02% active substance) in a spray chamber. Two days after application barley plants are inoculated by spraying a spore suspension (3×104 conidia/ml) on the test plants. After an incubation period of 2 days at 20° C. and 95% r.h. plants are kept for 2 days at 20° C. and 60% r.h. in a greenhouse. The disease incidence is assessed 4 days after inoculation.
Assay B-11: Effect Against Fusarium culmorum/Wheat (Fusarium Head Blight on Wheat)
A conidia suspension of F. culmorum (7×105 conidia/ml) is mixed with the formulated test compound (0.002% active substance). The mixture is applied into a pouch which has been equipped before with a filter paper. After the application wheat seeds (cv. Orestis) are sown into the upper fault of the filter paper. The prepared pouches are then incubated for 11 days at approx. 10–18° C. and a relative humidity of 100% with a light period of 14 hours. The evaluation is made by assessing the degree of disease occurrence in the form of brown lesions on the roots.
Assay B-12: Effect Against Septoria nodorum/Wheat (Septoria Leaf Spot on Wheat)
1 week old wheat plants cv. Arina are treated with a formulated test compound (0.02% active substance) in a spray chamber. One day after application wheat plants are inoculated by spraying a spore suspension (5×105 conidia/ml) on the test plants. After an incubation period of 1 day at 20° C. and 95% r.h. plants are kept for 10 days at 20° C. and 60% r.h. in a greenhouse. The disease incidence is assessed 11 days after inoculation.
Preferred among the compounds to be used according to the invention is a compound of the following tables.







TABLE 1





Compounds of the general formula I.1, in which R1 is fluorine, R2 and


R3 are hydrogen, n is 0, and R6 corresponds in each case to one of


the lines of Table A.

















(I)















Table 2

Compounds of the general formula I.1, in which R1 is chlorine, R2 and R3 are hydrogen, n is 0, and R6 corresponds in each case to one of the lines of Table A.
Table 3
Compounds of the general formula I.1, in which R1 is bromine, R2 and R3 are hydrogen, n is 0, and R6 corresponds in each case to one of the lines of Table A.
Table 4
Compounds of the general formula I.1, in which R1 is trifluoromethyl, R2 and R3 are hydrogen, n is 0, and R6 corresponds in each case to one of the lines of Table A.
Table 5
Compounds of the general formula I.1, in which R1 is trifluoromethoxy, R2 and R3 are hydrogen, n is 0, and R6 corresponds in each case to one of the lines of Table A.
Table 6
Compounds of the general formula I.1, in which R1 is chlorodifluoromethoxy, R2 and R3 are hydrogen, n is 0, and R6 corresponds in each case to one of the lines of Table A.
Table 7
Compounds of the general formula I.1, in which R1 is 2,2,2-trifluoroethoxy, R2 and R3 are hydrogen, n is 0, and R6 corresponds in each case to one of the lines of Table A.
Table 8
Compounds of the general formula I.1, in which R1 is 1,1,2,2-tetrafluoroethoxy, R2 and R3 are hydrogen, n is 0, and R6 corresponds in each case to one of the lines of Table A.
Table 9
Compounds of the general formula I.1, in which R1 is fluorine, R2 is methyl, R3 is hydrogen, n is 0, and R6 corresponds in each case to one of the lines of Table A.
Table 10
Compounds of the general formula I.1, in which R1 is chlorine, R2 is methyl, R3 is hydrogen, n is 0, and R6 corresponds in each case to one of the lines of Table A.
Table 11
Compounds of the general formula I.1, in which R1 is bromine, R2 is methyl, R3 is hydrogen, n is 0, and R6 corresponds in each case to one of the lines of Table A.
Table 12
Compounds of the general formula I.1, in which R1 is tritluoromethoxy, R2 is methyl, R3 is hydrogen, n is 0, and R6 corresponds in each case to one of the lines of Table A.
Table 13
Compounds of the general formula I.1, in which R1 is chlorodifluoromethoxy, R2 is methyl, R3 is hydrogen, n is 0, and R6 corresponds in each case to one of the lines of Table A.
Table 14
Compounds of the general formula I.1, in which R1 is 2,2,2-trifluoroethoxy, R2 is methyl, R3 is hydrogen, n is 0, and R6 corresponds in each case to one of the lines of Table A.
Table 15
Compounds of the general formula I.1, in which R1 is 1,1,2,2-tetrafluoroethoxy, R2 is methyl, R3 is hydrogen, n is 0, and R6 corresponds in each case to one of the lines of Table A.
Table 16
Compounds of the general formula I.1, in which R1 and R3 are fluorine, R2 is hydrogen, n is 0, and R6 corresponds in each case to one of the lines of Table A.
Table 17
Compounds of the general formula I.1, in which R1 is chlorine, R2 is hydrogen, R3 is fluorine, n is 0, and R6 corresponds in each case to one of the lines of Table A.
Table 18
Compounds of the general formula I.1, in which R1 is bromine, R2 is hydrogen, R3 is fluorine, n is 0, and R6 corresponds in each case to one of the lines of Table A.
Table 19
Compounds of the general formula I.1, in which R1 is trifluoromethoxy, R2 is hydrogen, R3 is fluorine, n is 0, and R6 corresponds in each case to one of the lines of Table A.
Table 20
Compounds of the general formula I.1, in which R1 is chlorodifluoromethoxy, R2 is hydrogen, R3 is fluorine, n is 0, and R6 corresponds in each case to one of the lines of Table A.
Table 21
Compounds of the general formula I.1, in which R1 is 2,2,2-trifluoroethoxy, R2 is hydrogen, R3 is fluorine, n is 0, and R6 corresponds in each case to one of the lines of Table A.
Table 22
Compounds of the general formula I.1, in which R1 is 1,1,2,2-tetrafluoroethoxy, R2 is hydrogen, R3 is fluorine, n is 0, and R6 corresponds in each case to one of the lines of Table A.
Table 23
Compounds of the general formula I.1, in which R1 and R3 are chlorine, R2 is hydrogen, n is 0, and R6 corresponds in each case to one of the lines of Table A.
Table 24
Compounds of the general formula I.1, in which R1 is fluorine, R2 is hydrogen, R3 is chlorine, n is 0, and R6 corresponds in each case to one of the lines of Table A.
Table 25
Compounds of the general formula I.1, in which R1 is bromine, R2 is hydrogen, R3 is chlorine, n is 0, and R6 corresponds in each case to one of the lines of Table A.
Table 26
Compounds of the general formula I.1, in which R1 is trifluoromethoxy, R2 is hydrogen, R3 is chlorine, n is 0, and R6 corresponds in each case to one of the lines of Table A.
Table 27
Compounds of the general formula I.1, in which R1 is chlorodifluoromethoxy, R2 is hydrogen, R3 is chlorine, n is 0, and R6 corresponds in each case to one of the lines of Table A.
Table 28
Compounds of the general formula I.1, in which R1 is 2,2,2-trifluoroethoxy, R2 is hydrogen, R3 is chlorine, n is 0, and R6 corresponds in each case to one of the lines of Table A.
Table 29
Compounds of the general formula I.1, in which R1 is 1,1,2,2-tetrafluoroethoxy, R2 is hydrogen, R3 is chlorine, n is 0, and R6 corresponds in each case to one of the lines of Table A.
Table 30
Compounds of the general formula I.1, in which R1 is fluorine, R2 and R3 are hydrogen, n is 1, and R6 corresponds in each case to one of the lines of Table A.
Table 31
Compounds of the general formula I.1, in which R1 is chlorine, R2 and R3 are hydrogen, n is 1, and R6 corresponds in each case to one of the lines of Table A.
Table 32
Compounds of the general formula I.1, in which R1 is bromine, R2 and R3 are hydrogen, n is 1, and R6 corresponds in each case to one of the lines of Table A.
Table 33
Compounds of the general formula I.1, in which R1 is trifluoromethyl, R2 and R3 are hydrogen, n is 1, and R6 corresponds in each case to one of the lines of Table A.
Table 34
Compounds of the general formula I.1, in which R1 is trifluoromethoxy, R2 and R3 are hydrogen, n is 1, and R6 corresponds in each case to one of the lines of Table A.
Table 35
Compounds of the general formula I.1, in which R1 is chlorodifluoromethoxy, R2 and R3 are hydrogen, n is 1, and R6 corresponds in each case to one of the lines of Table A.
Table 36
Compounds of the general formula I.1, in which R1 is 2,2,2-trifluoroethoxy, R2 and R3 are hydrogen, n is 1, and R6 corresponds in each case to one of the lines of Table A.
Table 37
Compounds of the general formula I.1, in which R1 is 1,1,2,2-tetrafluoroethoxy, R2 and R3 are hydrogen, n is 1, and R6 corresponds in each case to one of the lines of Table A.
Table 38
Compounds of the general formula I.1, in which R1 is fluorine, R2 is methyl, R3 is hydrogen, n is 1, and R6 corresponds in each case to one of the lines of Table A.
Table 39
Compounds of the general formula I.1, in which R1 is chlorine, R2 is methyl, R3 is hydrogen, n is 1, and R6 corresponds in each case to one of the lines of Table A.
Table 40
Compounds of the general formula I.1, in which R1 is bromine, R2 is methyl, R3 is hydrogen, n is 1, and R6 corresponds in each case to one of the lines of Table A.
Table 41
Compounds of the general formula I.1, in which R1 is trifluoromethoxy, R2 is methyl, R3 is hydrogen, n is 1, and R6 corresponds in each case to one of the lines of Table A.
Table 42
Compounds of the general formula I.1, in which R1 is chlorodifluoromethoxy, R2 is methyl, R3 is hydrogen, n is 1, and R6 corresponds in each case to one of the lines of Table A.
Table 43
Compounds of the general formula I.1, in which R1 is 2,2,2-trifluoroethoxy, R2 is methyl, R3 is hydrogen, n is 1, and R6 corresponds in each case to one of the lines of Table A.
Table 44
Compounds of the general formula I.1, in which R1 is 1,1,2,2-tetrafluoroethoxy, R2 is methyl, R3 is hydrogen, n is 1, and R6 corresponds in each case to one of the lines of Table A.
Table 45
Compounds of the general formula I.1, in which R1 and R3 are fluorine, R2 is hydrogen, n is 1, and R6 corresponds in each case to one of the lines of Table A.
Table 46
Compounds of the general formula I.1, in which R1 is chlorine, R2 is hydrogen, R3 is fluorine, n is 1, and R6 corresponds in each case to one of the lines of Table A.
Table 47
Compounds of the general formula I.1, in which R1 is bromine, R2 is hydrogen, R3 is fluorine, n is 1, and R6 corresponds in each case to one of the lines of Table A.
Table 48
Compounds of the general formula I.1, in which R1 is trifluoromethoxy, R2 is hydrogen, R3 is fluorine, n is 1, and R6 corresponds in each case to one of the lines of Table A.
Table 49
Compounds of the general formula I.1, in which R1 is chlorodifluoromethoxy, R2 is hydrogen, R3 is fluorine, n is 1, and R6 corresponds in each case to one of the lines of Table A.
Table 50
Compounds of the general formula I.1, in which R1 is 2,2,2-trifluoroethoxy, R2 is hydrogen, R3 is fluorine, n is 1, and R6 corresponds in each case to one of the lines of Table A.
Table 51
Compounds of the general formula I.1, in which R1 is 1,1,2,2-tetrafluoroethoxy, R2 is hydrogen, R3 is fluorine, n is 1, and R6 corresponds in each case to one of the lines of Table A.
Table 52
Compounds of the general formula I.1, in which R1 and R3 are chlorine, R2 is hydrogen, n is 1, and R6 corresponds in each case to one of the lines of Table A.
Table 53
Compounds of the general formula I.1, in which R1 is fluorine, R2 is hydrogen, R3 is chlorine, n is 1, and R6 corresponds in each case to one of the lines of Table A.
Table 54
Compounds of the general formula I.1, in which R1 is bromine, R2 is hydrogen, R3 is chlorine, n is 1, and R6 corresponds in each case to one of the lines of Table A.
Table 55
Compounds of the general formula I.1, in which R1 is trifluoromethoxy, R2 is hydrogen, R3 is chlorine, n is 1, and R6 corresponds in each case to one of the lines of Table A.
Table 56
Compounds of the general formula I.1, in which R1 is chlorodifluoromethoxy, R2 is hydrogen, R3 is chlorine, n is 1, and R6 corresponds in each case to one of the lines of Table A.
Table 57
Compounds of the general formula I.1, in which R1 is 2,2,2-trifluoroethoxy, R2 is hydrogen, R3 is chlorine, n is 1, and R6 corresponds in each case to one of the lines of Table A.
Table 58
Compounds of the general formula I.1, in which R1 is 1,1,2,2-tetrafluoroethoxy, R2 is hydrogen, R3 is chlorine, n is 1, and R6 corresponds in each case to one of the lines of Table A.








TABLE A





No.
R6
















1.
NHNH2


2.
NHNHCH3


3.
NHNHCH2CH3


4.
NHNH(CH2)2CH3


5.
NHNH(CH2)3CH3


6.
NHNHCH(CH3)2


7.
NHNHC(CH3)3


8.
NHN(CH3)2


9.
NHN(CH2CH3)2


10.
NHN[(CH2)2CH3]2


11.
NHN[(CH2)3CH3]2


12.
NHN[CH(CH3)2]2


13.
NHN(CH3)C(CH3)3


14.
NHN(CH3)CH2CH3


15.
N(CH3)NH2


16.
N(CH3)NHCH3


17.
N(CH3)NHCH2CH3


18.
N(CH3)NH(CH2)2CH3


19.
N(CH3)NH(CH2)3CH3


20.
N(CH3)NHCH(CH3)2


21.
N(CH3)NHC(CH3)3


22.
N(CH3)N(CH3)2


23.
N(CH3)N(CH2CH3)2


24.
N(CH3)N[(CH2)2CH3]2


25.
N(CH3)N[(CH2)3CH3]2


26.
N(CH3)N[CH(CH3)2]2


27.
N(CH3)N(CH3)C(CH3)3


28.
N(CH3)N(CH3)CH2CH3


29.
N(CH2CH3)NH2


30.
N(CH2CH3)NHCH3


31.
N(CH2CH3)NHCH2CH3


32.
N(CH2CH3)NH(CH2)2CH3


33.
N(CH2CH3)NH(CH2)3CH3


34.
N(CH2CH3)NHCH(CH3)2


35.
N(CH2CH3)NHC(CH3)3


36.
N(CH2CH3)N(CH3)2


37.
N(CH2CH3)N(CH2CH3)2


38.
N(CH2CH3)N[(CH2)2CH3]2


39.
N(CH2CH3)N[(CH2)3CH3]2


40.
N(CH2CH3)N[CH(CH3)2]2


41.
N(CH2CH3)N(CH3)CH2CH3


42.
N(CH2CF3)NH2


43.
N(CH2CF3)NHCH3


44.
N(CH2CF3)NHCH2CH3


45.
N(CH2CF3)NH(CH2)2CH3


46.
N(CH2CF3)NH(CH2)3CH3


47.
N(CH2CF3)NHCH(CH3)2


48.
N(CH2CF3)NHC(CH3)3


49.
N(CH2CF3)N(CH3)2


50.
N(CH2CF3)N(CH2CH3)2


51.
N(CH2CF3)N[(CH2)2CH3]2


52.
N(CH2CF3)N[(CH2)3CH3]2


53.
N(CH2CF3)N[CH(CH3)2]2


54.
N(CH2CF3)N(CH3)CH2CH3


55.
NHNHCH2CF3


56.
NHN(CH3)CH2CF3


57.
NHN(CH2CH3)CH2CF3


58.
NHN(CH2CF3)2


59.
N(CH3)NHCH2CF3


60.
N(CH3)N(CH3)CH2CF3


61.
N(CH3)N(CH2CH3)CH2CF3


62.
N(CH3)N(CH2CF3)2


63.
N(CH2CH3)NHCH2CF3


64.
N(CH2CH3)N(CH3)CH2CF3


65.
N(CH2CH3)N(CH2CH3)CH2CF3


66.
N(CH2CH3)N(CH2CF3)2


67.
N(CH2CF3)NHCH2CF3


68.
N(CH2CF3)N(CH2CF3)2


69.
N(CH2CH2OH)NH2


70.
N(CH2CH2OH)NHCH3


71.
N(CH2CH2OH)NHCH2CH3


72.
N(CH2CH2OH)NH(CH2)2CH3


73.
N(CH2CH2OH)NH(CH2)3CH3


74.
N(CH2CH2OH)NHCH(CH3)2


75.
N(CH2CH2OH)NHC(CH3)3


76.
N(CH2CH2OH)N(CH3)2


77.
N(CH2CH2OH)N(CH2CH3)2


78.
N(CH2CH2OH)N[(CH2)2CH3]2


79.
N(CH2CH2OH)N[(CH2)3CH3]2


80.
N(CH2CH2OH)N[CH(CH3)2]2


81.
N(CH2CH2OH)N(CH3)CH2CH3


82.
NHNHCH2CH2OH


83.
NHN(CH3)CH2CH2OH


84.
NHN(CH2CH3)CH2CH2OH


85.
NHN(CH2CH2OH)2


86.
N(CH3)NHCH2CH2OH


87.
N(CH3)N(CH3)CH2CH2OH


88.
N(CH3)N(CH2CH3)CH2CH2OH


89.
N(CH3)N(CH2CH2OH)2


90.
N(CH2CH3)NHCH2CH2OH


91.
N(CH2CH3)N(CH3)CH2CH2OH


92.
N(CH2CH3)N(CH2CH3)CH2CH2OH


93.
N(CH2CH3)N(CH2CH2CH)2


94.
N(CH2CH2CH)NHCH2CH2CH


95.
N(CH2CH2CH)N(CH2CH2CH)2


96.
N(CH2CH2OCH3)NH2


97.
N(CH2CH2OCH3)NHCH3


98.
N(CH2CH2OCH3)NHCH2CH3


99.
N(CH2CH2OCH3)NH(CH2)2CH3


100.
N(CH2CH2OCH3)NH(CH2)3CH3


101.
N(CH2CH2OCH3)NHCH(CH3)2


102.
N(CH2CH2OCH3)NHC(CH3)3


103.
N(CH2CH2OCH3)N(CH3)2


104.
N(CH2CH2OCH3)N(CH2CH3)2


105.
N(CH2CH2OCH3)N[(CH2)2CH3]2


106.
N(CH2CH2OCH3)N[(CH2)3CH3]2


107.
N(CH2CH2OCH3)N[CH(CH3)2]2


108.
N(CH2CH2OCH3)N(CH3)CH2CH3


109.
NHNHCH2CH2OCH3


110.
NHN(CH3)CH2CH2OCH3


111.
NHN(CH2CH3)CH2CH2OCH3


112.
NHN(CH2CH2OCH3)2


113.
N(CH3)NHCH2CH2OCH3


114.
N(CH3)N(CH3)CH2CH2OCH3


115.
N(CH3)N(CH2CH3)CH2CH2OCH3


116.
N(CH3)N(CH2CH2OCH3)2


117.
N(CH2CH3)NHCH2CH2OCH3


118.
N(CH2CH3)N(CH3)CH2CH2OCH3


119.
N(CH2CH3)N(CH2CH3)CH2CH2OCH3


120.
N(CH2CH3)N(CH2CH2OCH3)2


121.
N(CH2CH2OCH3)NH—CH2CH2OCH3


122.
N(CH2CH2OCH3)N—(CH2CH2OCH3)2


123.
NHNHCH2CH


124.
NHNHCH2OCH3


125.
NHNHCH2OCH2CH3


126.
NHN(CH3)CH2OH


127.
NHN(CH3)CH2OCH3


128.
NHN(CH3)CH2OCH2CH3


129.
N(CH3)NHCH2CH


130.
N(CH3)NHCH2OCH3


131.
N(CH3)NHCH2OCH2CH3


132.
N(CH3)N(CH3)CH2OH


133.
N(CH3)N(CH3)CH2OCH3


134.
N(CH3)N(CH3)CH2OCH2CH3


135.
N(CH2CH)NHCH2CH


136.
N(CH2OCH3)NHCH2OCH3


137.
N(CH2OCH2CH3)NH—CH2OCH2CH3


138.
N(CH2CH)N(CH3)CH2OH


139.
N(CH2OCH3)N(CH3)CH2OCH3


140.
N(CH2OCH2CH3)—N(CH3)CH2OCH3CH3


141.
NHNHCH(CH3)CH2OH


142.
NHN(CH3)CH(CH3)CH2OH


143.
N(CH3)NHCH(CH3)CH2OH


144.
N(CH3)N(CH3)CH(CH3)CH2OH


145.
NHNHCH(CH3)CH2OCH3


146.
NHN(CH3)CH(CH3)CH2OCH3


147.
N(CH3)NHCH(CH3)CH2OCH3


148.
N(CH3)N(CH3)CH(CH3)CH2OCH3


149.
NHNHCH(CH2CH3)CH2OH


150.
NHN(CH3)CH(CH2CH3)CH2OH


151.
N(CH3)NHCH(CH2CH3)CH2OH


152.
N(CH3)N(CH3)—CH(CH2CH3)CH2OH


153.
NHNHCH(CH2CH3)CH2OCH3


154.
NHN(CH3)CH(CH2CH3)CH2OCH3


155.
N(CH3)NHCH(CH2CH3)CH2OCH3


156.
N(CH3)N(CH2CH3)—CH(CH2CH3)CH2OCH3


157.
NHN(CH2CH3)—CH(CH2CH3)CH2OH


158.
N(CH3)N(CH2CH3)—CH(CH2CH3)CH2OH


159.
NHN(CH2CH3)—CH(CH2CH3)CH2OCH3


160.
N(CH3)N(CH2CH3)—CH(CH2CH3)CH2OCH3


161.
NHNHCHO


162.
NHNHC(O)CH3


163.
NHNHC(O)CH2CH3


164.
NHNHC(O)CH2CH2OCH3


165.
NHNHC(O)CF3


166.
NHNHC(O)CF2CF3


167.
NHNHC(O)(CF2)2CF3


168.
N(CHO)NH2


169.
N[C(O)CH3]NH2


170.
N[C(O)CH2CH3]NH2


171.
N[C(O)CH2CH2OCH3]NH2


172.
N[C(O)CF3]NH2


173.
N[C(O)CF2CF3]NH2


174.
N[C(O)(CF2)2CF3]NH2


175.
N(CHO)NH(CHO)


176.
N[C(O)CH3]NH[C(O)CH3)


177.
N[C(O)CH2CH3]NH[C(O)CH2CH3]


178.
N[C(O)CH2CH2OCH3]NH—[C(O)CH2CH2OCH3]


179.
N[C(O)CF3]NH[C(O)CF3]


180.
N[C(O)CF2CF3]NH[C(O)CF2CF3]


181.
N[C(O)(CF2)2CF3]NH—[C(O)(CF2)2CF3]


182.
NHN(CHO)2


183.
NHN[C(O)CH3]2


184.
NHN[C(O)CH2CH3]2


185.
NHN[C(O)CH2CH2OCH3]2


186.
NHN[C(O)CF3]2


187.
NHN[C(O)CF2CF3]2


188.
NHN[C(O)(CF2)2CF3]2


189.
N(CH3)NHCHO


190.
N(CH3)NHC(O)CH3


191.
N(CH3)NHC(O)CH2CH3


192.
N(CH3)NHC(O)CH2CH2OCH3


193.
N(CH3)NHC(O)CF3


194.
N(CH3)NHC(O)CF2CF3


195.
N(CH3)NHC(O)(CF2)2CF3


196.
N(CHO)NH(CH3)


197.
N[C(O)CH3]NH(CH3)


198.
N[C(O)CH2CH3]NH(CH3)


199.
N[C(O)CH2CH2OCH3]NH(CH3)


200.
N[C(O)CF3]NH(CH3)


201.
N[C(O)CF2CF3]NH(CH3)


202.
N[C(O)(CF2)2CF3]NH(CH3)


203.
N(CHO)N(CH3)(CHO)


204.
N[C(O)CH3]N(CH3)[C(O)CH3]


205.
N[C(O)CH2CH3]—N(CH3)[C(O)CH2CH3]


206.
N[C(O)CH2CH2OCH3]N(CH3)—[C(O)CH2CH2OCH3]


207.
N[C(O)CF3]N(CH3)[C(O)CF3]


208.
N[C(O)CF2CF3]—N(CH3)[C(O)CF2CF3]


209.
N[O(O)(CF2)2CF3]N(CH3)—[C(O)(CF2)2CF3]


210.
N(CH3)N(CHO)2


211.
N(CH3)N[C(O)CH3]2


212.
N(CH3)N[O(O)CH2CH3]2


213.
N(CH3)N[C(O)CH2CH2OCH3]2


214.
N(CH3)N[C(O)CF3]2


215.
N(CH3)N[C(O)CF2CF3]2


216.
N(CH3)N[C(O)(CF2)2CF3]2


217.
N(CH3)N(CH3)CHO


218.
N(CH3)N(CH3)C(O)CH3


219.
N(CH3)N(CH3)C(O)CH2CH3


220.
N(CH3)N(CH3)C(O)CH2CH2OCH3


221.
N(CH3)N(CH3)C(O)CF3


222.
N(CH3)N(CH3)C(O)CF2CF3


223.
N(CH3)N(CH3)C(O)(CF2)2CF3


224.
N(CHO)N(CH3)2


225.
N[C(O)CH3]N(CH3)2


226.
N[C(O)CH2CH3]N(CH3)2


227.
N[C(O)CH2CH2OCH3]N(CH3)2


228.
N[C(O)CF3]N(CH3)2


229.
N[C(O)CF2CF3]N(CH3)2


230.
N[C(O)(CF2)2CF3]N(CH3)2


 


231.






 


232.






 


233.






 


234.






 


235.






 


236.






 


237.






 


238.






 


239.






 


240.






 


241.
NH2


242.
NH(CH3)


243.
NH(CH2CH3)


244.
NH[(CH2)2CH3]


245.
NH[(CH2)3CH3]


246.
NH[(CH2)4CH3]


247.
NH[CH(CH3)2]


248.
NH[CH(CH2CH3)2]


249.
NH[C(CH3)3]


250.
NH[CH(CH3)CH2CH3]


251.
NH[CH2CH(CH3)2]


252.
N(CH3)2


253.
NCH3(CH2CH3)


254.
NCH3[(CH2)2CH3]


255.
NCH3[(CH2)3CH3]


256.
NCH3[(CH2)4CH3]


257.
NCH3[CH(CH3)2]


258.
NCH3[CH(CH2CH3)2]


259.
NCH3[C(CH3)3]


260.
NCH3[CH(CH3)CH2CH3]


261.
NCH3[CH2CH(CH3)2]


262.
NCH3(CH2CH3)


263.
N(CH2CH3)2


264.
NCH2CH3[(CH2)2CH3]


265.
NCH2CH3[(CH2)3CH3]


266.
NCH2CH3[(CH2)4CH3]


267.
NCH2CH3[CH(CH3)2]


268.
NCH2CH3[CH(CH2CH3)2]


269.
NCH2CH3[C(CH3)3]


270.
NCH2CH3[CH(CH3)CH2CH3]


271.
NCH2CH3[CH2CH(CH3)2]


272.
NH(CH2CH2NH2)


273.
NH[(CH2)3NH2]


274.
NH[CH(CH3)CH2NH2]


275.
NH[CH(CH3)CH2CH2NH2


276.
NH[CH(CH2CH3)CH2NH2]


277.
NH[CH(i-propyl)CH2NH2]


278.
NH(CH2CH2NHCH3)


279.
NH[(CH2)3NHCH3]


280.
NH[CH(CH3)CH2CH2NHCH3


281.
NH[CH(CH3)CH2NHCH3]


282.
NH[CH(CH2CH3)CH2NHCH3]


283.
NH[CH(i-propyI)CH2NHCH3]


284.
NH(CH2CH2N(CH3)2)


285.
NH[(CH2)3N(CH3)2]


286.
NH[CH(CH3)CH2CH2N(CH3)2


287.
NH[CH(CH3)CH2N(CH3)2]


288.
NH[CH(CH2CH3)CH2N(CH3)2]


289.
NH[CH(i-propyl)CH2N(CH3)2]


290.
NCH3(CH2CH2NH2)


291.
NCH3[(CH2)3NH2]


292.
NCH3[CH(CH3)CH2NH2]


293.
NCH3[CH(CH3)CH2CH2NH2


294.
NCH3[CH(CH2CH3)CH2NH2]


295.
NCH3[CH(i-propyl)CH2NH2]


296.
NCH3(CH2CH2NHCH3)


297.
NCH3[(CH2)3NHCH3]


298.
NCH3[CH(CH3)CH2NHCH3]


299.
NCH3[CH(CH3)CH2CH2NHCH3]


300.
NCH3[CH(CH2CH3)CH2NHCH3]


301.
NCH3[CH(i-propyl)CH2NHCH3)


302.
NCH3(CH2CH2N(CH3)2)


303.
NCH3[(CH2)3N(CH3)2]


304.
NCH3[CH(CH3)CH2N(CH3)2]


305.
NCH3[CH(CH3)CH2CH2N(CH3)2]


306.
NCH3[CH(CH2CH3)CH2N(CH3)2]


307.
NCH3[CH(i-propyl)CH2N(CH3)2]


308.
NH[CH2CH2OCH2OCH3]


309.
NH[CH(CH3)CH2OCH2OCH3]


310.
NH[CH2CH2OCH2OCH2CH3]


311.
NH[CH(CH3)CH2OCH2OCH2CH3]


312.
NH[CH(CH2CH3)CH2OCH2OCH3]


313.
NH[CH(CH2CH3)CH2O—CH2OCH2CH3]


314.
NCH3[CH2CH2OCH2OCH3]


315.
NCH3[CH(CH3)CH2OCH2OCH3]


316.
NCH3[CH2CH2OCH2OCH2CH3]


317.
NCH3[CH(CH3)CH2O—CH2OCH2CH3]


318.
NCH3[CH(CH2CH3)CH2O—CH2OCH3]


319.
NCH3[CH(CH2CH3)CH2O—CH2OCH2CH3]


320.
NCH2OCH3[CH2CH2OCH2OCH3]


321.
NCH2OCH3[CH(CH3)CH2O—CH2OCH3]


322.
NCH2OCH3[CH2CH2O—CH2OCH2CH3]


323.
NCH2OCH3[CH(CH3)CH2O—CH2OCH2CH3]


324.
NCH2OCH3[CH(CH2CH3)CH2O—CH2OCH3]


325.
NCH2OCH3[CH(CH2CH3)CH2O—CH2OCH2CH3]


326.
NHCH2CH2NHCH2CH2OH


327.
NHCH(CH3)CH2NHCH2CH2OH


328.
NHCH(CH2CH3)CH2NH—CH2CH2OH


329.
NHCH(CH(CH3)2)CH2NH—CH2CH2OH


330.
NHCH2CH2NH(CH2)3OH


331.
NHCH(CH3)CH2NH(CH2)3OH


332.
NHCH(CH2CH3)CH2NH—(CH2)3OH


333.
NHCH(CH(CH3)2)CH2NH—(CH2)3OH


334.
NHCH2CH2NHCH(CH3)CH2OH


335.
NHCH(CH3)CH2NH—CH(CH3)CH2OH


336.
NHCH(CH2CH3)CH2NH—CH(CH3)CH2OH


337.
NHCH(CH(CH3)2)CH2NH—CH(CH3)CH2OH


338.
NHCH2CH2NHCH2CH(CH3)OH


339.
NHCH(CH3)CH2NH—CH2CH(CH3)OH


340.
NHCH(CH2CH3)CH2NH—CH2CH(CH3)OH


341
NHCH(CH(CH3)2)CH2NH—CH2CH(CH3)OH


342.
NHCH2CN


343.
NH(CH2)2CN


344.
NH(CH2)3CN


345.
NH(CH2)4CN


346.
NHCH(CH3)CN


347.
NHCH(CH3)CH2CN


348.
NHCH(CH2CH3)CN


349.
NHCH(CH2CH3)CH2CN


350.
NHCH(CH(CH3)2)CN


351.
NHCH(CH(CH3)2)CH2CN


352.
N(CH3)CH2CN


353.
N(CH3)(CH2)2CN


354.
N(CH3)(CH2)3CN


355.
N(CH3)(CH2)4CN


356.
N(CH3)CH(CH3)CN


357.
N(CH3)CH(CH3)CH2CN


358.
N(CH3)CH(CH2CH3)CN


359.
N(CH3)CH(CH2CH3)CHCN


360.
N(CH3)CH(CH(CH3)2)CN


361.
N(CH3)CH(CH(CH3)2)CH2CN


362.
N(CH2CN)2


363.
N(CH2CH2CN)2


364.
NHCH2F


365.
NHCH2CH2F


366.
NHCH2CF3


367.
NHCH2CF2CF3


368.
N(CH3)CH2F


369.
N(CH3)CH2CH2F


370.
N(CH3)CH2CF3


371.
N(CH3)CH2CF2CF3


372.
N(CHO)CH2F


373.
N(CHO)CH2CH2F


374.
N(CHO)CH2CF3


375.
N(CHO)CH2CF2CF3


376.
N(COCH3)CH2F


377.
N(COCH3)CH2CH2F


378.
N(COCH3)CH2CF3


379.
N(COCH3)CH2CF2CF3


380.
N(CH2F)2


381.
N(CH2CH2F)2


382.
N(CH2CF3)2


383.
N(CH2CF2CF3)2


384.
NH(CH2CH═CH2)


385.
NH(CH2CH═CHCH3)


386.
NH(CH2CH═C(CH3)2)


387.
NH(CH(CH3)CH═CH2)


388.
NH(CH(CH3)CH═CHCH3)


389.
NH(CH(CH3)CH═C(CH3)2)


390.
NH(CH(CH2CH3)CH═CH2)


391.
NH(CH(CH2CH3)CH═CHCH3)


392.
NH(CH(CH2CH3)CH═C(CH3)2)


393.
NH(CH[CH(CH3)2]CH═CH2)


394.
NH(CH[CH(CH3)2]CH═CHCH3)


395.
NH(CH[CH(CH3)2]CH═C(CH3)2)


396.
N(CH3)(CH2CH═CH2)


397.
N(CH3)(CH2CH═CHCH3)


398.
N(CH3)(CH2CH═C(CH3)2)


399.
N(CH3)(CH(CH3)CH═CH2)


400.
N(CH3)(CH(CH3)CH═CHCH3)


401.
N(CH3)(CH(CH3)CH═C(CH3)2)


402.
N(CH3)(CH(CH2CH3)CH═CH2)


403.
N(CH3)(CH(CH2CH3)CH═CHCH3)


404.
N(CH3)—(CH(CH2CH3)CH═C(CH3)2)


405.
N(CH3)(CH[CH(CH3)2]CH═CH2)


406.
N(CH3)(CH[CH(CH3)2]CH═CHCH3)


407.
N(CH3)—(CH[CH(CH3)2]CH═C(CH3)2)


408.
NH(CH2C≡CH)


409.
NH(CH2C≡CCH3)


410.
NH(CH(CH3)C≡CH)


411.
NH(CH(CH3)C≡CCH3)


412.
NH(CH(CH2CH3)C≡CH)


413.
NH(CH(CH2CH3)C≡CCH3)


414.
NH(CH[CH(CH3)2]C≡CH)


415.
NH(CH[CH(CH3)2]C≡CCH3)


416.
N(CH3)(CH2C≡CH)


417.
N(CH3)(CH2C≡CCH3)


418.
N(CH3)(CH(CH3)C≡CH)


419.
N(CH3)(CH(CH3)C≡CCH3)


420.
N(CH3)(CH(CH2CH3)C≡CH)


421.
N(CH3)(CH(CH2CH3)C≡CCH3)


422.
N(CH3)(CH[CH(CH3)2]C≡CH)


423.
N(CH3)(CH[CH(CH3)2]C≡CCH3)


424.
N(CH3)—(CH[CH(CH3)2]C≡C(CH3)2)


425.
NHCH2CH2NHC(O)H


426.
NHCH2CH2NHC(O)CH3


427.
NHCH2CH2NH—C(O)CH2CH3


428.
NHCH2CH2NH—C(O)CF3


429.
NHCH2CH2NH—C(O)(CH2)2CH3


430.
NHCH2CH2NH—C(O)CH2OH


431.
NHCH2CH2NH—C(O)CH2OCH3


432.
NHCH2CH2NH—C(O)CH(CH3)OH


433.
NHCH2CH2NH—C(O)CH(CH3)OCH3


434.
NHCH2CH2NH—C(O)CH2CH(CH3)OH


435.
NHCH2CH2NH—C(O)CH2CH(CH3)OCH3


436.
NNCH2CH2NH—C(O)CH(CH3)CH2OH


437.
NHCH2CH2NH



C(O)CH(CH3)CH2OCH3


438.
NHCH2CH2CH2NHC(O)H


439.
NHCH2CH2CH2NH—C(O)CH3


440.
NHCH2CH2CH2NH—C(O)CH2CH3


441.
NHCH2CH2CH2NH—C(O)CF3


442.
NHCH2CH2CH2NH—C(O)(CH2)2CH3


443.
NHCH2CH2CH2NH—C(O)CH2OH


444.
NHCH2CH2CH2NH—C(O)CH2OCH3


445.
NHCH2CH2CH2NH—C(O)CH(CH3)OH


446.
NHCH2CH2CH2NH—C(O)CH(CH3)OCH3


447.
NHCH2CH2CH2NH—C(O)CH2CH(CH3)OH


448.
NHCH2CH2CH2NH—C(O)CH2CH(CH3)OCH3


449.
NHCH2CH2CH2NH—C(O)CH(CH3)CH2OH


450.
NHCH2CH2CH2NH—C(O)CH(CH3)CH2OCH3


451.
NHCH(CH3)CH2NHC(O)H


452.
NHCH(CH3)CH2NH—C(O)CH3


453.
NHCH(CH3)CH2NH—C(O)CH2CH3


454.
NHCH(CH3)CH2NH—C(O)CF3


455.
NHCH(CH3)CH2NH—C(O)(CH2)2CH3


456.
NHCH(CH3)CH2NH—C(O)CH2OH


457.
NHCH(CH3)CH2NH—C(O)CH2OCH3


458.
NHCH(CH3)CH2NH—C(O)CH(CH3)OH


459.
NHCH(CH3)CH2NH—C(O)CH(CH3)OCH3


460.
NHCH(CH3)CH2NH—C(O)CH2CH(CH3)OH


461.
NHCH(CH3)CH2NH—C(O)CH2CH(CH3)OCH3


462.
NHCH(CH3)CH2NH—C(O)CH(CH3)CH2OH


463.
NHCH(CH3)CH2NH—C(O)CH(CH3)CH2OCH3


464.
NHCH(CH3)CH2CH2NH—C(O)H


465.
NHCH(CH3)CH2CH2NH—C(O)CH3


466.
NHCH(CH3)CH2CH2NH—C(O)CH2CH3


467.
NHCH(CH3)CH2CH2NH—C(O)CF3


468.
NHCH(CH3)CH2CH2NH—C(O)(CH2)2CH3


469.
NHCH(CH3)CH2CH2NH—C(O)CH2OH


470.
NHCH(CH3)CH2CH2NH—C(O)CH2OCH3


471.
NHCH(CH3)CH2CH2NH—C(O)CH(CH3)OH


472.
NHCH(CH3)CH2CH2NH—C(O)CH(CH3)OCH3


473.
NHCH(CH3)CH2CH2NH—C(O)CH2CH(CH3)OH


474.
NHCH(CH3)CH2CH2NH—C(O)CH2CH(CH3)OCH3


475.
NHCH(CH3)CH2CH2NH—C(O)CH(CH3)CH2OH


476.
NHCH(CH3)CH2CH2NH—C(O)CH(CH3)CH2OCH3


477.
NHCH(CH2CH3)CH2NHC(O)H


478.
NHCH(CH2CH3)CH2NH—



C(O)CH3


479.
NHCH(CH2CH3)CH2NH—



C(O)CH2CH3


480.
NHCH(CH2CH3)CH2NH—



C(O)CF3


481.
NHCH(CH2CH3)CH2NH—



C(O)(CH2)2CH3


482.
NHCH(CH2CH3)CH2NH—



C(O)CH2OH


483.
NHCH(CH2CH3)CH2NH—



C(O)CH2OCH3


484.
NHCH(CH2CH3)CH2NH—



C(O)CH(CH3)OH


485.
NHCH(CH2CH3)CH2NH—



C(O)CH(CH3)OCH3


486.
NHCH(CH2CH3)CH2NH—



C(O)CH2CH(CH3)OH


487.
NHCH(CH2CH3)CH2NH—



C(O)CH2CH(CH3)OCH3


488.
NHCH(CH2CH3)CH2NH—



C(O)CH(CH3)CH2OH


489.
NHCH(CH2CH3)CH2NH—



C(O)CH(CH3)CH2OCH3


490.
NHCH(CH2CH3)CH2CH2NH—



C(O)H


491.
NHCH(CH2CH3)CH2CH2NH—



C(O)CH3


492.
NHCH(CH2CH3)CH2CH2NH—



C(O)CH2CH3


493.
NHCH(CH2CH3)CH2CH2NH—



C(O)CF3


494.
NHCH(CH2CH3)CH2CH2NH—



C(O)(CH2)2CH3


495.
NHCH(CH2CH3)CH2CH2NH—



C(O)CH2OH


496.
NHCH(CH2CH3)CH2CH2NH—



C(O)CH2OCH3


497.
NHCH(CH2CH3)CH2CH2NH—



C(O)CH(CH3)OH


498.
NHCH(CH2CH3)CH2CH2NI-I—



C(O)CH(CH3)OCH3


499.
NHCH(CH2CH3)CH2CH2NH—



C(O)CH2CH(CH3)OH


500.
NHCH(CH2CH3)CH2CH2NH—



C(O)CH2CH(CH3)OCH3


501.
NHCH(CH2CH3)CH2CH2NH—



C(O)CH(CH3)CH2OH


502.
NHCH(CH2CH3)CH2CH2NH—



C(O)CH(CH3)CH2OCH3


503.
NHCH(CH2CH2CH3)CH2NHC(O)H


504.
NHCH(CH2CH2CH3)CH2NH—



C(O)CH3


505.
NHCH(CH2CH2CH3)CH2NH—



C(O)CH2CH3


506.
NHCH(CH2CH2CH3)CH2NH—



C(O)CF3


507.
NHCH(CH2CH2CH3)CH2NH—



C(O)(CH2)2CH3


508.
NHCH(CH2CH2CH3)CH2NH—



C(O)CH2OH


509.
NHCH(CH2CH2CH3)CH2NH—



C(O)CH2OCH3


510.
NHCH(CH2CH2CH3)CH2NH—



C(O)CH(CH3)OH


511.
NHCH(CH2CH2CH3)CH2NH—



C(O)CH(CH3)OCH3


512.
NHCH(CH2CH2CH3)CH2NH—



C(O)CH2CH(CH3)OH


513.
NHCH(CH2CH2CH3)CH2NH—



C(O)CH2CH(CH3)OCH3


514.
NHCH(CH2CH2CH3)CH2NH—



C(O)CH(CH3)CH2OH


515.
NHCH(CH2CH2CH3)CH2NH—



C(O)CH(CH3)CH2OCH3


516.
NHCH(CH2CH2CH3)CH2CH2NH—



C(O)H


517.
NHCH(CH2CH2CH3)CH2CH2NH—



C(O)CH3


518.
NHCH(CH2CH2CH3)CH2CH2NH—



C(O)CH2CH3


519.
NHCH(CH2CH2CH3)CH2CH2NH—



C(O)CF3


520.
NHCH(CH2CH2CH3)CH2CH2NH—



C(O)(CH2)2CH3


521.
NHCH(CH2CH2CH3)CH2CH2NH—



C(O)CH2OH


522.
NHCH(CH2CH2CH3)CH2CH2NH—



C(O)CH2OCH3


523.
NHCH(CH2CH2CH3)CH2CH2NH—



C(O)CH(CH3)OH


524.
NHCH(CH2CH2CH3)CH2CH2NH—



C(O)CH(CH3)OCH3


525.
NHCH(CH2CH2CH3)CH2CH2NH—



C(O)CH2CH(CH3)OH


526.
NHCH(CH2CH2CH3)CH2CH2NH—



C(O)CH2CH(CH3)OCH3


527.
NHCH(CH2CH2CH3)CH2CH2NH—



C(O)CH(CH3)CH2OH


528.
NHCH(CH2CH2CH3)CH2CH2NH—



C(O)CH(CH3)CH2OCH3


529.
NHCH(CH(CH3)2)CH2NHC(O)H


530.
NHCH(CH(CH3)2)CH2NH—



C(O)CH3


531.
NHCH(CH(CH3)2)CH2NH—



C(O)CH2CH3


532.
NHCH(CH(CH3)2)CH2NH—



C(O)CF3


533.
NHCH(CH(CH3)2)CH2NH—



C(O)(CH2)2CH3


534.
NHCH(CH(CH3)2)CH2NH—



C(O)CH2OH


535.
NHCH(CH(CH3)2)CH2NH—



C(O)CH2OCH3


536.
NHCH(CH(CH3)2)CH2NH—



C(O)CH(CH3)OH


537.
NHCH(CH(CH3)2)CH2NH—



C(O)CH(CH3)OCH3


538.
NHCH(CH(CH3)2)CH2NH—



C(O)CH2CH(CH3)OH


539.
NHCH(CH(CH3)2)CH2NH—



C(O)CH(CH(CH3)2)OCH3


540.
NHCH(CH(CH3)2)CH2NH—



C(O)CH(CH3)CH2OH


541.
NHCH(CH(CH3)2)CH2NH—



C(O)CH(CH3)CH2OCH3


542.
NHCH(CH(CH3)2)CH2CH2NH—



C(O)H


543.
NHCH(CH(CH3)2)CH2CH2NH—



C(O)CH3


544.
NHCH(CH(CH3)2)CH2CH2NH—



C(O)CH2CH3


545.
NHCH(CH(CH3)2)CH2CH2NH—



C(O)CF3


546.
NHCH(CH(CH3)2)CH2CH2NH—



C(O)(CH2)2CH3


547.
NHCH(CH(CH3)2)CH2CH2NH—



C(O)CH2OH


548.
NHCH(CH(CH3)2)CH2CH2NH—



C(O)CH2OCH3


549.
NHCH(CH(CH3)2)CH2CH2NH—



C(O)CH(CH3)OH


550.
NHCH(CH(CH3)2)CH2CH2NH—



C(O)CH(CH3)OCH3


551.
NHCH(CH(CH3)2)CH2CH2NH—



C(O)CH2CH(CH3)OH


552.
NHCH(CH(CH3)2)CH2CH2NH—



C(O)CH2CH(CH3)OCH3


553.
NHCH(CH(CH3)2)CH2CH2NH—



C(O)CH(CH3)CH2OH


554.
NHCH(CH(CH3)2)CH2CH2NH—



C(O)CH(CH3)CH2OCH3


555.
NHCH2CH2NHC(O)OCH3


556.
NHCH2CH2NH—



C(O)OCH2CH3


557.
NHCH2CH2NH—



C(O)O(CH2)2CH3


558.
NHCH2CH2NH—



C(O)OCH(CH3)OH


559.
NHCH2CH2NH—C(O)OCH(CH3)OCH3


560.
NHCH2CH2NH—



C(O)OCH2CH(CH3)OH


561.
NHCH2CH2NH—



C(O)OCH2CH(CH3)OCH3


562.
NHCH2CH2NH—



O(O)OCH(CH3)CH2OH


563.
NHCH2CH2NH



C(O)OCH(CH3)CH2OCH3


564.
NHCH2CH2CH2NH—



C(O)OCH3


565.
NHCH2CH2CH2NH—



C(O)OCH2CH3


566.
NHCH2CH2CH2NH—C(O)O(CH2)2CH3


567.
NHCH2CH2CH2NH—



C(O)OCH(CH3)OH


568.
NHCH2CH2CH2NH—



C(O)OCH(CH3)OCH3


569.
NHCH2CH2CH2NH—



C(O)OCH2CH(CH3)OH


570.
NHCH2CH2CH2NH—



C(O)OCH2CH(CH3)OCH3


571.
NHCH2CH2CH2NH—



C(O)OCH(CH3)CH2OH


572.
NHCH2CH2CH2NH—



C(O)OCH(CH3)CH2OCH3


573.
NHCH(CH3)CH2NH—



C(O)OCH3


574.
NHCH(CH3)CH2NH—



C(O)OCH2CH3


575.
NHCH(CH3)CH2NH—



C(O)O(CH2)2CH3


576.
NHCH(CH3)CH2NH—



C(O)OCH(CH3)OH


577.
NHCH(CH3)CH2NH—



C(O)OCH(CH3)OCH3


578.
NHCH(CH3)CH2NH—



C(O)OCH2CH(CH3)OH


579.
NHCH(CH3)CH2NH—



C(O)OCH2CH(CH3)OCH3


580.
NHCH(CH3)CH2NH—



C(O)OCH(CH3)CH2OH


581.
NHCH(CH3)CH2NH—



C(O)OCH(CH3)CH2OCH3


582.
NHCH(CH3)CH2CH2NH—



C(O)OCH3


583.
NHCH(CH3)CH2CH2NH—



C(O)OCH2CH3


584.
NHCH(CH3)CH2CH2NH—



C(O)O(CH2)2CH3


585.
NHCH(CH3)CH2CH2NH—



C(O)OCH(CH3)OH


586.
NHCH(CH3)CH2CH2NH—



C(O)OCH(CH3)OCH3


587.
NHCH(CH3)CH2CH2NH—



C(O)OCH2CH(CH3)OH


588.
NHCH(CH3)CH2CH2NH—



C(O)OCH2CH(CH3)OCH3


589.
NHCH(CH3)CH2CH2NH—



C(O)OCH(CH3)CH2OH


590.
NHCH(CH3)CH2CH2NH—



C(O)OCH(CH3)CH2OCH3


591.
NHCH(CH2CH3)CH2NH—



C(O)OCH3


592.
NHCH(CH2CH3)CH2NH—



C(O)OCH2CH3


593.
NHCH(CH2CH3)CH2NH—



C(O)O(CH2)2CH3


594.
NHCH(CH2CH3)CH2NH—



C(O)OCH(CH3)OH


595.
NHCH(CH2CH3)CH2NH—



C(O)OCH(CH3)OCH3


596.
NHCH(CH2CH3)CH2NH—



C(O)OCH2CH(CH3)OH


597.
NHCH(CH2CH3)CH2NH—



C(O)OCH2CH(CH3)OCH3


598.
NHCH(CH2CH3)CH2NH—



C(O)OCH(CH3)CH2OH


599.
NHCH(CH2CH3)CH2NH—



C(O)OCH(CH3)CH2OCH3


600.
NHCH(CH2CH3)CH2CH2NH—



C(O)OCH3


601.
NHCH(CH2CH3)CH2CH2NH—



C(O)OCH2CH3


602.
NHCH(CH2CH3)CH2CH2NH—



C(O)O(CH2)2CH3


603.
NHCH(CH2CH3)CH2CH2NH—



C(O)OCH(CH3)OH


604.
NHCH(CH2CH3)CH2CH2NH—



C(O)OCH(CH3)OCH3


605.
NHCH(CH2CH3)CH2CH2NH—



C(O)OCH2CH(CH3)OH


606.
NHCH(CH2CH3)CH2CH2NH—



C(O)OCH2CH(CH3)OCH3


607.
NHCH(CH2CH3)CH2CH2NH—



C(O)OCH(CH3)CH2OH


608.
NHCH(CH2CH3)CH2CH2NH—



C(O)OCH(CH3)CH2OCH3


609.
NHCH(CH2CH2CH3)CH2NH—



C(O)OCH3


610.
NHCH(CH2CH2CH3)CH2NH—



C(O)OCH2CH3


611.
NHCH(CH2CH2CH3)CH2NH—



C(O)O(CH2)2CH3


612.
NHCH(CH2CH2CH3)CH2NH—



C(O)OCH2OCH3


613.
NHCH(CH2CH2CH3)CH2NH—



C(O)OCH(CH3)OH


614.
NHCH(CH2CH2CH3)CH2NH—



C(O)OCH(CH3)OCH3


615.
NHCH(CH2CH2CH3)CH2NH—



C(O)OCH2CH(CH3)OH


616.
NHCH(CH2CH2CH3)CH2NH—



C(O)OCH2CH(CH3)OCH3


617.
NHCH(CH2CH2CH3)CH2NH—



C(O)OCH(CH3)CH2OH


618.
NHCH(CH2CH2CH3)CH2NH—



C(O)OCH(CH3)CH2OCH3


619.
NHCH(CH2CH2CH3)CH2CH2NH—



C(O)OCH3


620.
NHCH(CH2CH2CH3)CH2CH2NH—



C(O)OCH2CH3


621.
NHCH(CH2CH2CH3)CH2CH2NH—



C(O)O(CH2)2CH3


622.
NHCH(CH2CH2CH3)CH2CH2NH—



C(O)OCH(CH3)OH


623.
NHCH(CH2CH2CH3)CH2CH2NH—



C(O)OCH(CH3)OCH3


624.
NHCH(CH2CH2CH3)CH2CH2NH—



C(O)OCH2CH(CH3)OH


625.
NHCH(CH2CH2CH3)CH2CH2NH—



C(O)OCH2CH(CH3)OCH3


626.
NHCH(CH2CH2CH3)CH2CH2NH—



C(O)OCH(CH3)CH2OH


627.
NHCH(CH2CH2CH3)CH2CH2NH—



C(O)OCH(CH3)CH2OCH3


628.
NHCH(CH(CH3)2)CH2NH—



C(O)OCH3


629.
NHCH(CH(CH3)2)CH2NH—



C(O)OCH2CH3


630.
NHCH(CH(CH3)2)CH2NH—



C(O)O(CH2)2CH3


631.
NHCH(CH(CH3)2)CH2NH—



C(O)OCH(CH3)OCH3


632.
NHCH(CH(CH3)2)CH2NH—



C(O)OCH2CH(CH3)OH


633.
NHCH(CH(CH3)2)CH2NH—



C(O)OCH(CH(CH3)2)OCH3


634.
NHCH(CH(CH3)2)CH2NH—



C(O)OCH(CH3)CH2OH


635.
NHCH(CH(CH3)2)CH2NH—



C(O)OCH(CH3)CH2OCH3


636.
NHCH(CH(CH3)2)CH2CH2NH—



C(O)OCH3


637.
NHCH(CH(CH3)2)CH2CH2NH—



C(O)OCH2CH3


638.
NHCH(CH(CH3)2)CH2CH2NH—



C(O)O(CH2)2CH3


639.
NHCH(CH(CH3)2)CH2CH2NH—



C(O)OCH(CH3)OCH3


640.
NHCH(CH(CH3)2)CH2CH2NH—



C(O)OCH2CH(CH3)OH


641.
NHCH(CH(CH3)2)CH2CH2NH—



C(O)OCH2CH(CH3)OCH3


642.
NHCH(CH(CH3)2)CH2CH2NH—



C(O)OCH(CH3)CH2OH


643.
NHCH(CH(CH3)2)CH2CH2NH—



C(O)OCH(CH3)CH2OCH3


644.
NHCH2CH2NHC(O)NHCH3


645.
NHCH2CH2NH—



C(O)NHCH2CH3


646.
NHCH2CH2NH—



C(O)NH(CH2)2CH3


647.
NHCH2CH2NH—



C(O)NHCH(CH3)OH


648.
NHCH2CH2NH—



C(O)NHCH(CH3)OCH3


649.
NHCH2CH2NH—



C(O)NHCH2CH(CH3)OH


650.
NHCH2CH2NH—



C(O)NHCH2CH(CH3)OCH3


651.
NHCH2CH2NH—



C(O)NHCH(CH3)CH2OH


652.
NHCH2CH2NH



C(O)NHCH(CH3)CH2OCH3


653.
NHCH2CH2CH2NH—



C(O)NHCH3


654.
NHCH2CH2CH2NH—



C(O)NHCH2CH3


655.
NHCH2CH2CH2NH—



C(O)NH(CH2)2CH3


656.
NHCH2CH2CH2NH—



C(O)NHCH(CH3)OH


657.
NHCH2CH2CH2NH—



C(O)NHCH(CH3)OCH3


658.
NHCH2CH2CH2NH—



C(O)NHCH2CH(CH3)OH


659.
NHCH2CH2CH2NH—



C(O)NHCH2CH(CH3)OCH3


660.
NHCH2CH2CH2NH—



C(O)NHCH(CH3)CH2OH


661.
NHCH2CH2CH2NH—



C(O)NHCH(CH3)CH2OCH3


662.
NHCH(CH3)CH2NH—



C(O)NHCH3


663.
NHCH(CH3)CH2NH—



C(O)NHCH2CH3


664.
NHCH(CH3)CH2NH—



C(O)NH(CH2)2CH3


665.
NHCH(CH3)CH2NH—



C(O)NHCH(CH3)OH


666.
NHCH(CH3)CH2NH—



C(O)NHCH(CH3)OCH3


667.
NHCH(CH3)CH2NH—



C(O)NHCH2CH(CH3)OH


668.
NHCH(CH3)CH2NH—



C(O)NHCH2CH(CH3)OCH3


669.
NHCH(CH3)CH2NH—



C(O)NHCH(CH3)CH2OH


670.
NHCH(CH3)CH2NH—



C(O)NHCH(CH3)CH2OCH3


671.
NHCH(CH3)CH2CH2NH—



C(O)NHCH3


672.
NHCH(CH3)CH2CH2NH—



C(O)NHCH2CH3


673.
NHCH(CH3)CH2CH2NH—



C(O)NH(CH2)2CH3


674.
NHCH(CH3)CH2CH2NH—



C(O)NHCH(CH3)OH


675.
NHCH(CH3)CH2CH2NH—



C(O)NHCH(CH3)OCH3


676.
NHCH(CH3)CH2CH2NH—



C(O)NHCH2CH(CH3)OH


677.
NHCH(CH3)CH2CH2NH—



C(O)NHCH2CH(CH3)OCH3


678.
NHCH(CH3)CH2CH2NH—



C(O)NHCH(CH3)CH2OH


679.
NHCH(CH3)CH2CH2NH—



C(O)NHCH(CH3)CH2OCH3


680.
NHCH(CH2CH3)CH2NH—



C(O)NHCH3


681.
NHCH(CH2CH3)CH2NH—



C(O)NHCH2CH3


682.
NHCH(CH2CH3)CH2NH—



C(O)NH(CH2)2CH3


683.
NHCH(CH2CH3)CH2NH—



C(O)NHCH(CH3)OH


684.
NHCH(CH2CH3)CH2NH—



C(O)NHCH(CH3)OCH3


685.
NHCH(CH2CH3)CH2NH—



C(O)NHCH2CH(CH3)OH


686.
NHCH(CH2CH3)CH2NH—



C(O)NHCH2CH(CH3)OCH3


687.
NHCH(CH2CH3)CH2NH—



C(O)NHCH(CH3)CH2OH


688.
NHCH(CH2CH3)CH2NH—



C(O)NHCH(CH3)CH2OCH3


689.
NHCH(CH2CH3)CH2CH2NH—



C(O)NHCH3


690.
NHCH(CH2CH3)CH2CH2NH—



C(O)NHCH2CH3


691.
NHCH(CH2CH3)CH2CH2NH—



C(O)NH(CH2)2CH3


692.
NHCH(CH2CH3)CH2CH2NH—



C(O)NHCH2OCH3


693.
NHCH(CH2CH3)CH2CH2NH—



C(O)NHCH(CH3)OH


694.
NHCH(CH2CH3)CH2CH2NH—



C(O)NHCH(CH3)OCH3


695.
NHCH(CH2CH3)CH2CH2NH—



C(O)NHCH2CH(CH3)OH


696.
NHCH(CH2CH3)CH2CH2NH—



C(O)NHCH2CH(CH3)OCH3


697.
NHCH(CH2CH3)CH2CH2NH—



C(O)NHCH(CH3)CH2ON


698.
NHCH(CH2CH3)CH2CH2NH—



C(O)NHCH(CH3)CH2OCH3


699.
NHCH(CH2CH2CH3)CH2NH—



C(O)NHCH3


700.
NHCH(CH2CH2CH3)CH2NH—



C(O)NHCH2CH3


701.
NHCH(CH2CH2CH3)CH2NH—



C(O)NH(CH2)2CH3


702.
NHCH(CH2CH2CH3)CH2NH—



C(O)NHCH(CH3)OH


703.
NHCH(CH2CH2CH3)CH2NH—



C(O)NHCH(CH2)OCH3


704.
NHCH(CH2CH2CH3)CH2NH—



C(O)NHCH2CH(CH3)OH


705.
NHCH(CH2CH2CH3)CH2NH—



C(O)NHCH2CH(CH3)OCH3


706.
NHCH(CH2CH2CH3)CH2NH—



C(O)NHCH(CH3)CH2OH


707.
NHCH(CH2CH2CH3)CH2NH—



C(O)NHCH(CH3)CH2OCH3


708.
NHCH(CH2CH2CH3)CH2CH2NH—



C(O)NHCH3


709.
NHCH(CH2CH2CH3)CH2CH2NH—



C(O)NHCH2CH3


710.
NHCH(CH2CH2CH3)CH2CH2NH—



C(O)NH(CH2)2CH3


711.
NHCH(CH2CH2CH3)CH2CH2NH—



C(O)NHCH(CH3)OH


712.
NHCH(CH2CH2CH3)CH2CH2NH—



C(O)NHCH(CH3)OCH3


713.
NHCH(CH2CH2CH3)CH2CH2NH—



C(O)NHCH2CH(CH3)OH


714.
NHCH(CH2CH2CH3)CH2CH2NH—



C(O)NHCH2CH(CH3)OCH3


715.
NHCH(CH2CH2CH3)CH2CH2NH—



C(O)NHCH(CH3)CH2OH


716.
NHCH(CH2CH2CH3)CH2CH2NH—



C(O)NHCH(CH3)CH2OCH3


717.
NHCH(CH(CH3)2)CH2NH—



C(O)NHCH3


718.
NHCH(CH(CH3)2)CH2NH—



C(O)NHCH2CH3


719.
NHCH(CH(CH3)2)CH2NH—



C(O)NH(CH2)2CH3


720.
NHCH(CH(CH3)2)CH2NH—



C(O)NHCH(CH3)OCH3


721.
NHCH(CH(CH3)2)CH2NH—



C(O)NHCH2CH(CH3)OH


722.
NHCH(CH(CH3)2)CH2NH—



C(O)NHCH(CH(CH3)2)OCH3


723.
NHCH(CH(CH3)2)CH2NH—



C(O)NHCH(CH3)CH2OH


724.
NHCH(CH(CH3)2)CH2NH—



C(O)NHCH(CH3)CH2OCH3


725.
NHCH(CH(CH3)2)CH2CH2NH—



C(O)NHCH3


726.
NHCH(CH(CH3)2)CH2CH2NH—



C(O)NHCH2CH3


727.
NHCH(CH(CH3)2)CH2CH2NH—



C(O)NH(CH2)2CH3


728.
NHCH(CH(CH3)2)CH2CH2NH—



C(O)NHCH(CH3)OCH3


729.
NHCH(CH(CH3)2)CH2CH2NH—



C(O)NHCH2CH(CH3)OH


730.
NHCH(CH(CH3)2)CH2CH2NH—



C(O)NHCH2CH(CH3)OCH3


731.
NHCH(CH(CH3)2)CH2CH2NH—



C(O)NHCH(CH3)CH2OH


732.
NHCH(CH(CH3)2)CH2CH2NH—



C(O)NHCH(CH3)CH2OCH3


733.
NHCH2CH2OC(O)H


734.
NHCH2CH2OC(O)CH3


735.
NHCHCH2O—



C(O)CH2CH3


736.
NHCH2CH2O—



C(O)CF3


737.
NHCH2CH2O—



C(O)(CH2)2CH3


738.
NHCH2CH2O—



C(O)CH2OH


739.
NHCH2CH2O—



C(O)CH2OCH3


740.
NHCH2CH2O—



C(O)CH(CH3)OH


741.
NHCH2CH2OC(O)CH(CH3)OCH3


742.
NHCH2CH2O—C(O)CH2CH(CH3)OH


743.
NHCH2CH2O—



C(O)CH2CH(CH3)OCH3


744.
NHCH2CH2O—C(O)CH(CH3)CH2OH


745.
NHCH2CH2O—



C(O)CH(CH3)CH2OCH3


746.
NHCH2CH2CH2OC(O)H


747.
NHCH2CH2CH2OC(O)CH3


748.
NHCH2CH2CH2O—



C(O)CH2CH3


749.
NHCH2CH2CH2OC(O)CF3


750.
NHCH2CH2CH2OC(O)(CH2)2CH3


751.
NHCH2CH2CH2OC(O)CH2OH


752.
NHCH2CH2CH2O—



C(O)CH2OCH3


753.
NHCH2CH2CH2O—C(O)CH(CH3)OH


754.
NHCH2CH2CH2O—



C(O)CH(CH3)OCH3


755.
NHCH2CH2CH2O—



C(O)CH2CH(CH3)OH


756.
NHCH2CH2CH2O—



C(O)CH2CH(CH3)OCH3


757.
NHCH2CH2CH2O—



C(O)CH(CH3)CH2OH


758.
NHCH2CH2CH2O—



C(O)CH(CH3)CH2OCH3


759.
NHCH(CH3)CH2OC(O)H


760.
NHCH(CH3)CH2OC(O)CH3


761.
NHCH(CH3)CH2OC(O)CH2CH3


762.
NHCH(CH3)CH2OC(O)CF3


763.
NHCH(CH3)CH2OC(O)(CH2)2CH3


764.
NHCH(CH3)CH2OC(O)CH2OH


765.
NHCH(CH3)CH2OC(O)CH2OCH3


766.
NHCH(CH3)CH2OC(O)CH(CH3)OH


767.
NHCH(CH3)CH2O—



C(O)CH(CH3)OCH3


768.
NHCH(CH3)CH2O—



C(O)CH2CH(CH3)OH


769.
NHCH(CH3)CH2O—



C(O)CH2CH(CH3)OCH3


770.
NHCH(CH3)CH2O—



C(O)CH(CH3)CH2OH


771.
NHCH(CH3)CH20—



C(O)CH(CH3)CH2OCH3


772.
NHCH(CH3)CH2CH2OC(O)H


773.
NHCH(CH3)CH2CH2OC(O)CH3


774.
NHCH(CH3)CH2CH2O—C(O)CH2CH3


775.
NHCH(CH3)CH2CH2OC(O)CF3


776.
NHCH(CH3)CH2CH2O—



C(O)(CH2)2CH3


777.
NHCH(CH3)CH2CH2OC(O)CH2OH


778.
NHCH(CH3)CH2CH2O—



C(O)CH2OCH3


779.
NHCH(CH3)CH2CH2O—



C(O)CH(CH3)OH


780.
NHCH(CH3)CH2CH2O—



C(O)CH(CH3)OCH3


781.
NHCH(CH3)CH2CH2O—



C(O)CH2CH(CH3)OH


782.
NHCH(CH3)CH2CH2O—



C(O)CH2CH(CH3)OCH3


783.
NHCH(CH3)CH2CH2O—



C(O)CH(CH3)CH2OH


784.
NHCH(CH3)CH2CH2O—



C(O)CH(CH3)CH2OCH3


785.
NHCH(CH2CH3)CH2OC(O)H


786.
NHCH(CH2CH3)CH2OC(O)CH3


787.
NHCH(CH2CH3)CH20—



C(O)CH2CH3


788.
NHCH(CH2CH3)CH2O—



C(O)CF3


789.
NHCH(CH2CH3)CH2O—



C(O)(CH2)2CH3


790.
NHCH(CH2CH3)CH2O—C(O)CH2OH


791.
NHCH(CH2CH3)CH2O—



C(O)CH2OCH3


792.
NHCH(CH2CH3)CH2O—



C(O)CH(CH3)OH


793.
NHCH(CH2CH3)CH2O—



C(O)CH(CH3)OCH3


794.
NHCH(CH2CH3)CH2O—



C(O)CH2CH(CH3)OH


795.
NHCH(CH2CH3)CH2O—



C(O)CH2CH(CH3)OCH3


796.
NHCH(CH2CH3)CH2O—



C(O)CH(CH3)CH2OH


797.
NHCH(CH2CH3)CH2O—



C(O)CH(CH3)CH2OCH3


798.
NHCH(CH2CH3)CH2CH2O—



C(O)H


799.
NHCH(CH2CH3)CH2CH2O—



C(O)CH3


800.
NHCH(CH2CH3)CH2CH2O—



C(O)CH2CH3


801.
NHCH(CH2CH3)CH2CH2O—C(O)CF3


802.
NHCH(CH2CH3)CH2CH2O—



C(O)(CH2)2CH3


803.
NHCH(CH2CH3)CH2CH2O—



C(O)CH2OH


804.
NHCH(CH2CH3)CH2CH2O—



C(O)CH2OCH3


805.
NHCH(CH2CH3)CH2CH2O—



C(O)CH(CH3)OH


806.
NHCH(CH2CH3)CH2CH2O—



C(O)CH(CH3)OCH3


807.
NHCH(CH2CH3)CH2CH2O—



C(O)CH2CH(CH3)OH


808.
NHCH(CH2CH3)CH2CH2O—



C(O)CH2CH(CH3)OCH3


809.
NHCH(CH2CH3)CH2CH2O—



C(O)CH(CH3)CH2OH


810.
NHCH(CH2CH3)CH2CH2O—



C(O)CH(CH3)CH2OCH3


811.
NHCH(CH2CH2CH3)CH2OC(O)H


812.
NHCH(CH2CH2CH3)CH2O—



C(O)CH3


813.
NHCH(CH2CH2CH3)CH2O—



C(O)CH2CH3


814.
NHCH(CH2CH2CH3)CH2O—



C(O)CF3


815.
NHCH(CH2CH2CH3)CH2O—



C(O)(CH2)2CH3


816.
NHCH(CH2CH2CH3)CH2O—



C(O)CH2OH


817.
NHCH(CH2CH2CH3)CH2O—



C(O)CH2OCH3


818.
NHCH(CH2CH2CH3)CH2O—



C(O)CH(CH3)OH


819.
NHCH(CH2CH2CH3)CH2O—



C(O)CH(CH3)OCH3


820.
NHCH(CH2CH2CH3)CH2O—



C(O)CH2CH(CH3)OH


821.
NHCH(CH2CH2CH3)CH2O—



C(O)CH2CH(CH3)OCH3


822.
NHCH(CH2CH2CH3)CH2O—



C(O)CH(CH3)CH2OH


823.
NHCH(CH2CH2CH3)CH2O—



C(O)CH(CH3)CH2OCH3


824.
NHCH(CH2CH2CH3)CH2CH2O—



C(O)H


825.
NHCH(CH2CH2CH3)CH2CH2O—



C(O)CH3


826.
NHCH(CH2CH2CH3)CH2CH2O—



C(O)CH2CH3


827.
NHCH(CH2CH2CH3)CH2CH2O—



C(O)CF3


828.
NHCH(CH2CH2CH3)CH2CH2O—



C(O)(CH2)2CH3


829.
NHCH(CH2CH2CH3)CH2CH2O—



C(O)CH2OH


830.
NHCH(CH2CH2CH3)CH2CH2O—



C(O)CH2OCH3


831.
NHCH(CH2CH2CH3)CH2CH2O—



C(O)CH(CH3)OH


832.
NHCH(CH2CH2CH3)CH2CH2O—



C(O)CH(CH3)OCH3


833.
NHCH(CH2CH2CH3)CH2CH2O—



C(O)CH2CH(CH3)OH


834.
NHCH(CH2CH2CH3)CH2CH2O—



C(O)CH2CH(CH3)OCH3


835.
NHCH(CH2CH2CH3)CH2CH2O—



C(O)CH(CH3)CH2OH


836.
NHCH(CH2CH2CH3)CH2CH2O—



C(O)CH(CH3)CH2OCH3


837.
NHCH(CH(CH3)2)CH2OC(O)H


838.
NHCH(CH(CH3)2)CH2OC(O)CH3


839.
NHCH(CH(CH3)2)CH2O—



C(O)CH2CH3


840.
NHCH(CH(CH3)2)CH2OC(O)CF3


841.
NHCH(CH(CH3)2)CH2O—



C(O)(CH2)2CH3


842.
NHCH(CH(CH3)2)CH2O—



C(O)CH2OH


843.
NHCH(CH(CH3)2)CH2O—



C(O)CH2OCH3


844.
NHCH(CH(CH3)2)CH2O—



C(O)CH(CH3)OH


845.
NHCH(CH(CH3)2)CH2O—



C(O)CH(CH3)OCH3


846.
NHCH(CH(CH3)2)CH2O—



C(O)CH2CH(CH3)OH


847.
NHCH(CH(CH3)2)CH2O—



C(O)CH(CH(CH3)2)OCH3


848.
NHCH(CH(CH3)2)CH2O—



C(O)CH(CH3)CH2OH


849.
NHCH(CH(CH3)2)CH2O—



C(O)CH(CH3)CH2OCH3


850.
NHCH(CH(CH3)2)CH2CH2O—



C(O)H


851.
NHCH(CH(CH3)2)CH2CH2O—



C(O)CH3


852.
NHCH(CH(CH3)2)CH2CH2O—



C(O)CH2CH3


853.
NHCH(CH(CH3)2)CH2CH2O—



C(O)CF3


854.
NHCH(CH(CH3)2)CH2CH2O—



C(O)(CH2)2CH3


855.
NHCH(CH(CH3)2)CH2CH2O—



C(O)CH2OH


856.
NHCH(CH(CH3)2)CH2CH2O—



C(O)CH2OCH3


857.
NHCH(CH(CH3)2)CH2CH2O—



C(O)CH(CH3)OH


858.
NHCH(CH(CH3)2)CH2CH2O—



C(O)CH(CH3)OCH3


859.
NHCH(CH(CH3)2)CH2CH2O—



C(O)CH2CH(CH3)OH


860.
NHCH(CH(CH3)2)CH2CH2O—



C(O)CH2CH(CH3)OCH3


861.
NHCH(CH(CH3)2)CH2CH2O—



C(O)CH(CH3)CH2OH


862.
NHCH(CH(CH3)2)CH2CH2O—



C(O)CH(CH3)CH2OCH3


863.
NHCH2CH2OC(O)OCH3


864.
NHCH2CH2OC(O)OCH2CH3


865.
NHCH2CH2OC(O)O(CH2)2CH3


866.
NHCH2CH2OC(O)OCH(CH3)OH


867.
NHCH2CH2OC(O)OCH(CH3)OCH3


868.
NHCH2CH2O—C(O)OCH2CH(CH3)OH


869.
NHCH2CH2O—



C(O)OCH2CH(CH3)OCH3


870.
NHCH2CH2O—C(O)OCH(CH3)CH2OH


871.
NHCH2CH2O—



C(O)OCH(CH3)CH2OCH3


872.
NHCH2CH2CH2OC(O)OCH3


873.
NHCH2CH2CH2OC(O)OCH2CH3


874.
NHCH2CH2CH2O—C(O)O(CH2)2CH3


875.
NHCH2CH2CH2O—C(O)OCH(CH3)OH


876.
NHCH2CH2CH2O—



C(O)OCH(CH3)OCH3


877.
NHCH2CH2CH2O—



C(O)OCH2CH(CH3)OH


878.
NHCH2CH2CH2O—



C(O)OCH2CH(CH3)OCH3


879.
NHCH2CH2CH2O—



C(O)OCH(CH3)CH2OH


880.
NHCH2CH2CH2O—



C(O)OCH(CH3)CH2OCH3


881.
NHCH(CH3)CH2OC(O)OCH3


882.
NHCH(CH3)CH2OC(O)OCH2CH3


883.
NHCH(CH3)CH2O—C(O)O(CH2)2CH3


884.
NHCH(CH3)CH2O—



C(O)OCH(CH3)OH


885.
NHCH(CH3)CH2O—



C(O)OCH(CH3)OCH3


886.
NHCH(CH3)CH2O—



C(O)OCH2CH(CH3)OH


887.
NHCH(CH3)CH2O—



C(O)OCH2CH(CH3)OCH3


888.
NHCH(CH3)CH2O—



C(O)OCH(CH3)CH2OH


889.
NHCH(CH3)CH2O—



C(O)OCH(CH3)CH2OCH3


890.
NHCH(CH3)CH2CH2O—



C(O)OCH3


891.
NHCH(CH3)CH2CH2O—



C(O)OCH2CH3


892.
NHCH(CH3)CH2CH2O—



C(O)O(CH2)2CH3


893.
NHCH(CH3)CH2CH2O—



C(O)OCH(CH3)OH


894.
NHCH(CH3)CH2CH2O—



C(O)OCH(CH3)OCH3


895.
NHCH(CH3)CH2CH2O—



C(O)OCH2CH(CH3)OH


896.
NHCH(CH3)CH2CH2O—



C(O)OCH2CH(CH3)OCH3


897.
NHCH(CH3)CH2CH2O—



C(O)OCH(CH3)CH2OH


898.
NHCH(CH3)CH2CH2O—



C(O)OCH(CH3)CH2OCH3


899.
NHCH(CH2CH3)CH2OC(O)OCH3


900.
NHCH(CH2CH3)CH2O—



C(O)OCH2CH3


901.
NHCH(CH2CH3)CH2O—



C(O)O(CH2)2CH3


902.
NHCH(CH2CH3)CH2O—



C(O)OCH(CH3)OH


903.
NHCH(CH2CH3)CH2O—



C(O)OCH(CH3)OCH3


904.
NHCH(CH2CH3)CH2O—



C(O)OCH2CH(CH3)OH


905.
NHCH(CH2CH3)CH2O—



C(O)OCH2CH(CH3)OCH3


906.
NHCH(CH2CH3)CH2O—



C(O)OCH(CH3)CH2OH


907.
NHCH(CH2CH3)CH2O—



C(O)OCH(CH3)CH2OCH3


908.
NHCH(CH2CH3)CH2CH2O—



C(O)OCH3


909.
NHCH(CH2CH3)CH2CH2O—



C(O)OCH2CH3


910.
NHCH(CH2CH3)CH2CH2O—



C(O)O(CH2)2CH3


911.
NHCH(CH2CH3)CH2CH2O—



C(O)OCH(CH3)OH


912.
NHCH(CH2CH3)CH2CH2O—



C(O)OCH(CH3)OCH3


913.
NHCH(CH2CH3)CH2CH2O—



C(O)OCH2CH(CH3)OH


914.
NHCH(CH2CH3)CH2CH2O—



C(O)OCH2CH(CH3)OCH3


915.
NHCH(CH2CH3)CH2CH2O—



C(O)OCH(CH3)CH2OH


916.
NHCH(CH2CH3)CH2CH2O—



C(O)OCH(CH3)CH2OCH3


917.
NHCH(CH2CH2CH3)CH2O—



C(O)OCH3


918.
NHCH(CH2CH2CH3)CH2O—



C(C)OCH2CH3


919.
NHCH(CH2CH2CH3)CH2O—



C(O)O(CH2)2CH3


920.
NHCH(CH2CH2CH3)CH2O—



C(O)OCH2OCH3


921.
NHCH(CH2CH2CH3)CH2O—



C(O)OCH(CH3)OH


922.
NHCH(CH2CH2CH3)CH2O—



C(O)OCH(CH3)OCH3


923.
NHCH(CH2CH2CH3)CH2O—



C(O)OCH2CH(CH3)OH


924.
NHCH(CH2CH2CH3)CH2O—



C(O)OCH2CH(CH3)OCH3


925.
NHCH(CH2CH2CH3)CH2O—



C(O)OCH(CH3)CH2OH


926.
NHCH(CH2CH2CH3)CH2O—



C(O)OCH(CH3)CH2OCH3


927.
NHCH(CH2CH2CH3)CH2CH2O—



C(O)OCH3


928.
NHCH(CH2CH2CH3)CH2CH2O—



C(O)OCH2CH3


929.
NHCH(CH2CH2CH3)CH2CH2O—



C(O)O(CH2)2CH3


930.
NHCH(CH2CH2CH3)CH2CH2O—



C(O)OCH(CH3)OH


931.
NHCH(CH2CH2CH3)CH2CH2O—



C(O)OCH(CH3)OCH3


932.
NHCH(CH2CH2CH3)CH2CH2O—



C(O)OCH2CH(CH3)OH


933.
NHCH(CH2CH2CH3)O—



C(O)OCH2CH(CH3)OCH3


934.
NHCH(CH2CH2CH3)CH2CH2O—



C(O)OCH(CH3)CH2OH


935.
NHCH(CH2CH2CH3)CH2CH2O—



C(O)OCH(CH3)CH2OCH3


936.
NHCH(CH(CH3)2)CH2O—



C(O)OCH3


937.
NHCH(CH(CH3)2)CH2O—



C(O)OCH2CH3


938.
NHCH(CH(CH3)2)CH2O—



C(O)O(CH2)2CH3


939.
NHCH(CH(CH3)2)CH2O—



C(O)OCH(CH3)OCH3


940.
NHCH(CH(CH3)2)CH2O—



C(O)OCH2CH(CH3)OH


941.
NHCH(CH(CH3)2)CH2O—



C(O)OCH(CH(CH3)2)OCH3


942.
NHCH(CH(CH3)2)CH2O—



C(O)OCH(CH3)CH2OH


943.
NHCH(CH(CH3)2)CH2O—



C(O)OCH(CH3)CH2OCH3


944.
NHCH(CH(CH3)2)CH2CH2O—



C(O)OCH3


945.
NHCH(CH(CH3)2)CH2CH2O—



C(O)OCH2CH3


946.
NHCH(CH(CH3)2)CH2CH2O—



C(O)O(CH2)2CH3


947.
NHCH(CH(CH3)2)CH2CH2O—



C(O)OCH(CH3)OCH3


948.
NHCH(CH(CH3)2)CH2CH2O—



C(O)OCH2CH(CH3)OH


949.
NHCH(CH(CH3)2)CH2CH2O—



C(O)OCH2CH(CH3)OCH3


950.
NHCH(CH(CH3)2)CH2CH2O—



C(O)OCH(CH3)CH2OH


951.
NHCH(CH(CH3)2)CH2CH2O—



C(O)OCH(CH3)CH2OCH3


952.
NHCH2COOH


953.
NHCH2C(O)OCH3


954.
NHCH2C(O)OCH2CH3


955.
NHCH2C(O)O(CH2)2CH3


956.
NHCH2C(O)OCH(CH3)OH


957.
NHCH2C(O)OCH(CH3)OCH3


958.
NHCH2C(O)OCH2CH(CH3)OH


959.
NHCH2C(O)OCH2CH(CH3)OCH3


960.
NHCH2C(O)OCH(CH3)CH2OH


961.
NHCH2C(O)OCH(CH3)CH2OCH3


962.
NHCH2C(O)NH2


963.
NHCH2C(O)NHOH


964.
NHCH2C(NH)NH2


965.
NHCH2C(O)NHCH3


966.
NHCH2C(O)NHCH2CH3


967.
NHCH2C(O)NH(CH2)2CH3


968.
NHCH2C(O)NHCH(CH3)OH


969.
NHCH2C(O)NHCH(CH3)OCH3


970.
NHCH2C(O)NHCH2CH(CH3)OH


971.
NHCH2C(O)NHCH2CH(CH3)OCH3


972.
NHCH2C(O)NHCH(CH3)CH2OH


973.
NHCH2C(O)NHCH(CH3)CH2OCH3


974.
NHCH2C(O)N(CH3)2


975.
NHCH2C(O)N(CH2CH3)2


976.
NHCH(CH3)COOH


977.
NHCH(CH3)C(O)OCH3


978.
NHCH(CH3)C(O)OCH2CH3


979.
NHCH(CH3)C(O)O(CH2)2CH3


980.
NHCH(CH3)C(O)OCH(CH3)OH


981.
NHCH(CH3)C(O)OCH(CH3)OCH3


982.
NHCH(CH3)C(O)OCH2CH(CH3)OH


983.
NHCH(CH3)C(O)—



OCH2CH(CH3)OCH3


984.
NHCH(CH3)C(O)OCH(CH3)CH2OH


985.
NHCH(CH3)C(O)—



OCH(CH3)CH2OCH3


986.
NHCH(CH3)C(O)NH2


987.
NHCH(CH3)C(O)NHOH


988.
NHCH(CH3)C(NH)NH2


989.
NHCH(CH3)C(O)NHCH3


990.
NHCH(CH3)C(O)NHCH2CH3


991.
NHCH(CH3)C(O)NH(CH2)2CH3


992.
NHCH(CH3)C(O)NHCH(CH3)OH


993.
NHCH(CH3)C(O)NHCH(CH3)OCH3


994.
NHCH(CH3)C(O)—



NHCH2CH(CH3)OH


995.
NHCH(CH3)C(O)—



NHCH2CH(CH3)OCH3


996.
NHCH(CH3)C(O)—



NHCH(CH3)CH2OH


997.
NHCH(CH3)C(O)—



NHCH(CH3)CH2OCH3


998.
NHCH(CH3)C(O)N(CH3)2


999.
NHCH(CH3)C(O)N(CH2CH3)2


1000.
NHCH2CH2COOH


1001.
NHCH2CH2C(O)OCH3


1002.
NHCH2CH2C(O)OCH2CH3


1003.
NHCH2CH2C(O)O(CH2)2CH3


1004.
NHCH2CH2C(O)OCH(CH3)OH


1005.
NHCH2CH2C(O)OCH(CH3)OCH3


1006.
NHCH2CH2C(O)OCH2CH(CH3)OH


1007.
NHCH2CH2C(O)—



OCH2CH(CH3)OCH3


1008.
NHCH2CH2C(O)OCH(CH3)CH2OH


1009.
NHCH2CH2C(O)—



OCH(CH3)CH2OCH3


1010.
NHCH2CH2C(O)NH2


1011.
NHCH2CH2C(O)NHOH


1012.
NHCH2CH2C(NH)NH2


1013.
NHCH2CH2C(O)NHCH3


1014.
NHCH2CH2C(O)NHCH2CH3


1015.
NHCH2CH2C(O)NH(CH2)2CH3


1016.
NHCH2CH2C(O)NHCH(CH3)OH


1017.
NHCH2CH2C(O)NHCH(CH3)OCH3


1018.
NHCH2CH2C(O)—NHCH2CH(CH3)OH


1019.
NHCH2CH2C(O)—



NHCH2CH(CH3)OCH3


1020.
NHCH2CH2C(O)—NHCH(CH3)CH2OH


1021.
NHCH2CH2C(O)—



NHCH(CH3)CH2OCH3


1022.
NHCH2CH2C(O)N(CH3)2


1023.
NHCH2CH2C(O)N(CH2CH3)2


1024.
NHCH2OCH3


1025.
NHCH2OCH2CH3


1026.
NHCH2O(CH2)2CH3


1027.
NHCH2OCH(CH3)2


1028.
NHCH2OCH2OCH3


1029.
NHCH2CH2OH


1030.
NHCH2CH2OCH3


1031.
NHCH2CH2OCH2CH3


1032.
NHCH2CH2O(CH2)2CH3


1033.
NHCH2CH2OCH(CH3)2


1034.
NHCH2CH2OCH2OCH3


1035.
NHCH2CH2CH2OH


1036.
NHCH2CH2CH2OCH3


1037.
NHCH2CH2CH2OCH2CH3


1038.
NHCH2CH2CH2O(CH2)2CH3


1039.
NHCH2CH2CH2OCH(CH3)2


1040.
NHCH2CH2CH2OCH2OCH3


1041.
NHCH(CH3)OCH3


1042.
NHCH(CH3)OCH2CH3


1043.
NHCH(CH3)O(CH2)2CH3


1044.
NHCH(CH3)OCH(CH3)2


1045.
NHCH(CH3)OCH2OCH3


1046.
NHC[(CH3)2]OCH3


1047.
NHC[(CH3)2]PCH2CH3


1048.
NHC[(CH3)2]O(CH2)2CH3


1049.
NHC[(CH3)2]OCH(CH3)2


1050.
NHC[(CH3)2]OCH2OCH3


1051.
NHCH(CH2CH3)OCH3


1052.
NHCH(CH2CH3)OCH2CH3


1053.
NHCH(CH2CH3)O(CH2)2CH3


1054.
NHCH(CH2CH3)OCH(CH3)2


1055.
NHCH(CH2CH3)OCH2OCH3


1056.
NHCH(CH2CH)OCH3


1057.
NHCH(CH2CH)OCH2CH3


1058.
NHCH(CH2CH)O(CH2)2CH3


1059.
NHCH(CH2CH)OCH(CH3)2


1060.
NHCH(CH2CH)OCH2OCH3


1061.
NHCH(CH2OCH3)OCH3


1062.
NHCH(CH2OCH3)OCH2CH3


1063.
NHCH(CH2OCH3)O(CH2)2CH3


1064.
NHCH(CH2OCH3)OCH(CH3)2


1065.
NHCH(CH2OCH3)OCH2OCH3


1066.
NHCH[CH(CH3)2]OCH3


1067.
NHCH[CH(CH3)2]OCH2CH3


1068.
NHCH[CH(CH3)2]O(CH2)2CH3


1069.
NHCH{CH(CH3)2]OCH(CH3)2


1070.
NHCH[CH(CH3)2]OCH2OCH3


1071.
NHCH(CH(CH2CH3)CH3)OCH3


1072.
NHCH(CH(CH2CH3)CH3)—OCH2CH3


1073.
NHCH(CH(CH2CH3)CH3)—



O(CH2)2CH3


1074.
NHCH(CH(CH2CH3)CH3)—



OCH(CH3)2


1075.
NHCH(CH(CH2CH3)CH3)—



OCH2OCH3


1076.
NHCH(CH2CH2CH3)OCH3


1077.
NHCH(CH2CH2CH3)OCH2CH3


1078.
NHCH(CH2CH2CH3)O(CH2)2CH3


1079.
NHCH(CH2CH2CH3)OCH(CH3)2


1080.
NHCH(CH2CH2CH3)OCH2OCH3


1081.
NHCH(CH3)CH2OH


1082.
NHCH(CH3)CH2OCH3


1083.
NHCH(CH3)CH2OCH2CH3


1084.
NHCH(CH3)CH2O(CH2)2CH3


1085.
NHCH(CH3)CH2OCH(CH3)2


1086.
NHCH(CH3)CH2OCH2OCH3


1087.
NHCH(CH2CH3)CH2OH


1088.
NHCH(CH2CH3)CH2OCH3


1089.
NHCH(CH2CH3)CH2OCH2CH3


1090.
NHCH(CH2CH3)CH2O(CH2)2CH3


1091.
NHCH(CH2CH3)CH2OCH(CH3)2


1092.
NHCH(CH2CH3)CH2OCH2OCH3


1093.
NHC[(CH3)2]CH2OH


1094.
NHC[(CH3)2]CH2OCH3


1095.
NHC[(CH3)2]CH2OCH2CH3


1096.
NHC[(CH3)2]CH2O(CH2)2CH3


1097.
NHC[(CH3)2]CH2OCH(CH3)2


1098.
NHC[(CH3)2]CH2OCH2OCH3


1099.
NHCH(CH2CH)CH2OH


1100.
NHCH(CH2CH)CH2OCH3


1101.
NHCH(CH2CH)CH2OCH2CH3


1102.
NHCH(CH2CH)CH2O(CH2)2CH3


1103.
NHCH(CH2CH)CH2OCH(CH3)2


1104.
NHCH(CH2CH)CH2OCH2OCH3


1105.
NHCH(CH2OCH3)CH2OH


1106.
NHCH(CH2OCH3)CH2OCH3


1107.
NHCH(CH2OCH3)CH2OCH2CH3


1108.
NHCH(CH2OCH3)CH2O—(CH2)2CH3


1109.
NHCH(CH2OCH3)CH2OCH(CH3)2


1110.
NHCH(CH2OCH3)CH2OCH2OCH3


1111.
NHCH2CH(CH3)OH


1112.
NHCH2CH(CH3)OCH3


1113.
NHCH2CH(CH3)OCH2CH3


1114.
NHCH2CH(CH3)O(CH2)2CH3


1115.
NHCH2CH(CH3)OCH(CH3)2


1116.
NHCH2CH(CH3)OCH2OCH3


1117.
NHCH2CH(CH2CH3)OH


1118.
NHCH2CH(CH2CH3)OCH3


1119.
NHCH2CH(CH2CH3)OCH2CH3


1120.
NHCH2CH(CH2CH3)O(CH2)2CH3


1121.
NHCH2CH(CH2CH3)OCH(CH3)2


1122.
NHCH2CH(CH2CH3)OCH2OCH3


1123.
NHCH2CH(CH2CH)OH


1124.
NHCH2CH(CH2CH)OCH3


1125.
NHCH2CH(CH2CH)OCH2CH3


1126.
NHCH2C(CH2CH)(CH2CH)O—



(CH2)2CH3


1127.
NHCH2CH(CH2CH)OCH(CH3)2


1128.
NHCH2CH(CH2CH)OCH2OCH3


1129.
NHCH2CH(CH2OCH3)OH


1130.
NHCH2CH(CH2OCH3)OCH3


1131.
NHCH2CH(CH2OCH3)OCH2CH3


1132.
NHCH2CH(CH2OCH3)O—



(CH2)2CH3


1133.
NHCH2CH(CH2OCH3)OCH(CH3)2


1134.
NHCH2CH(CH2OCH3)OCH2OCH3


1135.
NHCH(CH3)CH2CH2OH


1136.
NHCH(CH3)CH2CH2OCH3


1137.
NHCH(CH3)CH2CH2OCH2CH3


1138.
NHCH(CH3)CH2CH2O(CH2)2CH3


1139.
NHCH(CH3)CH2CH2OCH(CH3)2


1140.
NHCH(CH3)CH2CH2OCH2OCH3


1141.
NHCH(CH2CH3)CH2CH2OH


1142.
NHCH(CH2CH3)CH2CH2OCH3


1143.
NHCH(CH2CH3)CH2CH2O–CH2CH3


1144.
NHCH(CH2CH3)CH2CH2O—



(CH2)2CH3


1145.
NHCH(CH2CH3)CH2CH2O—CH(CH3)2


1146.
NHCH(CH2CH3)CH2CH2O—CH2OCH3


1147.
NHC[(CH3)2]CH2CH2OH


1148.
NHC[(CH3)2]CH2CH2OCH3


1149.
NHC[(CH3)2]CH2CH2OCH2CH3


1150.
NHC[(CH3)2]CH2CH2O(CH2)2CH3


1151.
NHC[(CH3)2]CH2CH2OCH(CH3)2


1152.
NHC[(CH3)2]CH2CH2OCH2OCH3


1153.
NHCH(CH2CH)CH2CH2OH


1154.
NHCH(CH2CH)CH2CH2OCH3


1155.
NHCH(CH2CH)CH2CH2OCH2CH3


1156.
NHCH(CH2CH)CH2CH2O—(CH2)2CH3


1157.
NHCH(CH2CH)CH2CH2O—CH(CH3)2


1158.
NHCH(CH2CH)CH2CH2O—CH2OCH3


1159.
NHCH(CH2OCH3)CH2CH2OH


1160.
NHCH(CH2OCH3)CH2CH2OCH3


1161.
NHCH(CH2OCH3)CH2CH2O—CH2CH3


1162.
NHCH(CH2OCH3)CH2CH2O—



(CH2)2CH3


1163.
NHCH(CH2OCH3)CH2CH2O—



CH(CH3)2


1164.
NHCH(CH2OCH3)CH2CH2O—



CH2OCH3


1165.
NHCH(CH3)CH(CH3)OH


1166.
NHCH(CH3)CH(CH3)OCH3


1167.
NHCH(CH3)CH(CH3)OCH2CH3


1168.
NHCH(CH3)CH(CH3)O(CH2)2CH3


1169.
NHCH(CH3)CH(CH3)OCH(CH3)2


1170.
NHCH(CH3)CH(CH3)OCH2OCH3


1171.
NHCH(CH2CH3)CH(CH3)OH


1172.
NHCH(CH2CH3)CH(CH3)OCH3


1173.
NHCH(CH2CH3)CH(CH3)O—CH2CH3


1174.
NHCH(CH2CH3)CH(CH3)O—



(CH2)2CH3


1175.
NHCH(CH2CH3)CH(CH3)O—



CH(CH3)2


1176.
NHCH(CH2CH3)CH(CH3)O—



CH2OCH3


1177.
NHC[(CH3)2)CH(CH3)OH


1178.
NHC[(CH3)2]CH(CH3)OCH3


1179.
NHC[(CH3)2]CH(CH3)OCH2CH3


1180.
NHC[(CH3)2]CH(CH3)O(CH2)2CH3


1181.
NHC[(CH3)2]CH(CH3)OCH(CH3)2


1182.
NHC[(CH3)2]CH(CH3)OCH2OCH3


1183.
NHCH(CH2CH)CH(CH3)OH


1184.
NHCH(CH2CH)CH(CH3)OCH3


1185.
NHCH(CH2CH)CH(CH3)OCH2CH3


1186.
NHCH(CH2CH)CH(CH3)O—



(CH2)2CH3


1187.
NHCH(CH2CH)CH(CH3)O—CH(CH3)2


1188.
NHCH(CH2CH)CH(CH3)O—CH2OCH3


1189.
NHCH(CH2OCH3)CH(CH3)OH


1190.
NHCH(CH2OCH3)CH(CH3)OCH3


1191.
NHCH(CH2OCH3)CH(CH3)O—



CH2CH3


1192.
NHCH(CH2OCH3)CH(CH3)O—



(CH2)2CH3


1193.
NHCH(CH2OCH3)CH(CH3)O—



CH(CH3)2


1194.
NHCH(CH2OCH3)CH(CH3)O—



CH2OCH3


1195.
N(CH3)CH2OCH3


1196.
N(CH3)CH2OCH2CH3


1197.
N(CH3)CH2O(CH2)2CH3


1198.
N(CH3)CH2OCH(CH3)2


1199.
N(CH3)CH2OCH2OCH3


1200.
N(CH3)CH2CH2OH


1201.
N(CH3)CH2CH2OCH3


1202.
N(CH3)CH2CH2OCH2CH3


1203.
N(CH3)CH2CH2O(CH2)2CH3


1204.
N(CH3)CH2CH2OCH(CH3)2


1205.
N(CH3)CH2CH2OCH2OCH3


1206.
N(CH3)CH2CH2CH2OH


1207.
N(CH3)CH2CH2CH2OCH3


1208.
N(CH3)CH2CH2CH2OCH2CH3


1209.
N(CH3)CH2CH2CH2O(CH2)2CH3


1210.
N(CH3)CH2CH2CH2OCH(CH3)2


1211.
N(CH3)CH2CH2CH2OCH2OCH3


1212.
N(CH3)CH(CH3)OCH3


1213.
N(CH3)CH(CH3)OCH2CH3


1214.
N(CH3)CH(CH3)O(CH2)2CH3


1215.
N(CH3)CH(CH3)OCH(CH3)2


1216.
N(CH3)CH(CH3)OCH2OCH3


1217.
N(CH3)CH(CH2CH)O(CH2)2CH3


1218.
N(CH3)CH(CH2CH)OCH(CH3)2


1219.
N(CH3)CH(CH2CH)OCH2OCH3


1220.
N(CH3)CH(CH2OCH3)OCH3


1221.
N(CH3)CH(CH2OCH3)OCH2CH3


1222.
N(CH3)CH(CH2OCH3)O—(CH2)2CH3


1223.
N(CH3)CH(CH2OCH3)OCH(CH3)2


1224.
N(CH3)CH(CH2OCH3)OCH2OCH3


1225.
N(CH3)CH(CH3)CH2OH


1226.
N(CH3)CH(CH3)CH2OCH3


1227.
N(CH3)CH(CH3)CH2OCH2CH3


1228.
N(CH3)CH(CH3)CH2O(CH2)2CH3


1229.
N(CH3)CH(CH3)CH2OCH(CH3)2


1230.
N(CH3)CH(CH3)CH2OCH2OCH3


1231.
N(CH3)CH(CH2CH3)CH2OH


1232.
N(CH3)CH(CH2CH3)CH2OCH3


1233.
N(CH3)CH(CH2CH3)CH2OCH2CH3


1234.
N(CH3)CH(CH2CH3)CH2O—



(CH2)2CH3


1235.
N(CH3)CH(CH2CH3)CH2O—CH(CH3)2


1236.
N(CH3)CH(CH2CH3)CH2O—CH2OCH3


1237.
N(CH3)CH(CH2CH)CH2OH


1238.
N(CH3)CH(CH2CH)CH2OCH3


1239.
N(CH3)CH(CH2CH)CH2OCH2CH3


1240.
N(CH3)CH(CH2CH)CH2O—(CH2)2CH3


1241.
N(CH3)CH(CH2CH)CH2O—CH(CH3)2


1242.
N(CH3)CH(CH2CH)CH2O—CH2OCH3


1243.
N(CH3)CH(CH2OCH3)CH2OH


1244.
N(CH3)CH(CH2OCH3)CH2OCH3


1245.
N(CH3)CH(CH2OCH3)CH2O—CH2CH3


1246.
N(CH3)CH(CH2OCH3)CH2O—



(CH2)2CH3


1247.
N(CH3)CH(CH2OCH3)CH2O—



CH(CH3)2


1248.
N(CH3)CH(CH2OCH3)CH2O—



CH2OCH3


1249.
N(CH3)CH2CH(CH3)OH


1250.
N(CH3)CH2CH(CH3)OCH3


1251.
N(CH3)CH2CH(CH3)OCH2CH3


1252.
N(CH3)CH2CH(CH3)O(CH2)2CH3


1253.
N(CH3)CH2CH(CH3)OCH(CH3)2


1254.
N(CH3)CH2CH(CH3)OCH2OCH3


1255.
N(CH3)CH2CH(CH2CH3)OH


1256.
N(CH3)CH2CH(CH2CH3)OCH3


1257.
N(CH3)CH2CH(CH2CH3)OCH2CH3


1258.
N(CH3)CH2CH(CH2CH3)O—



(CH2)2CH3


1259.
N(CH3)CH2CH(CH2CH3)O—CH(CH3)2


1260.
N(CH3)CH2CH(CH2CH3)O—CH2OCH3


1261.
N(CH3)CH2CH(CH2CH)OH


1262.
N(CH3)CH2CH(CH2CH)OCH3


1263.
N(CH3)CH2CH(CH2CH)OCH2CH3


1264.
N(CH3)CH2CH(CH2CH)(CH2CH)—



O(CH2)2CH3


1265.
N(CH3)CH2CH(CH2CH)—OCH(CH3)2


1266.
N(CH3)CH2CH(CH2CH)O—CH2OCH3


1267.
N(CH3)CH2CH(CH2OCH3)OH


1268.
N(CH3)CH2CH(CH2OCH3)OCH3


1269.
N(CH3)CH2CH(CH2OCH3)O—CH2CH3


1270.
N(CH3)CH2CH(CH2OCH3)O—



(CH2)2CH3


1271.
N(CH3)CH2CH(CH2OCH3)O—



CH(CH3)2


1272.
N(CH3)CH2CH(CH2OCH3)O—



CH2OCH3


1273.
N(CH3)CH(CH3)CH2CH2OH


1274.
N(CH3)CH(CH3)CH2CH2OCH3


1275.
N(CH3)CH(CH3)CH2CH2OCH2CH3


1276.
N(CH3)CH(CH3)CH2CH2O—



(CH2)2CH3


1277.
N(CH3)CH(CH3)CH2CH2O—CH(CH3)2


1278.
N(CH3)CH(CH3)CH2CH2O—CH2OCH3


1279.
N(CH3)CH(CH2CH3)CH2CH2OH


1280.
N(CH3)CH(CH2CH3)CH2CH2OCH3


1281.
N(CH3)CH(CH2CH3)CH2CH2O—



CH2CH3


1282.
N(CH3)CH(CH2CH3)CH2CH2O—



(CH2)2CH3


1283.
N(CH3)CH(CH2CH3)CH2CH2O—



CH(CH3)2


1284.
N(CH3)CH(CH2CH3)CH2CH2O—



CH2OCH3


1285.
N(CH3)C[(CH3)2]CH2CH2OH


1286.
N(CH3)C[(CH3)2]CH2CH2OCH3


1287.
N(CH3)C[(CH3)2]CH2CH2O—CH2CH3


1288.
N(CH3)C[(CH3)2]CH2CH2O—



(CH2)2CH3


1289.
N(CH3)C[(CH3)2]CH2CH2O—CH(CH3)2


1290.
N(CH3)C[(CH3)2]CH2CH2O—



CH2OCH3


1291.
N(CH3)CH(CH2CH)CH2CH2OH


1292.
N(CH3)CH(CH2CH)CH2CH2OCH3


1293.
N(CH3)CH(CH2CH)—



CH2CH2OCH2CH3


1294.
N(CH3)CH(CH2CH)CH2CH2O—



(CH2)2CH3


1295.
N(CH3)CH(CH2CH)CH2CH2O—



CH(CH3)2


1296.
N(CH3)CH(CH2CH)CH2CH2O—



CH2OCH3


1297.
N(CH3)CH(CH2OCH3)CH2CH2OH


1298.
N(CH3)CH(CH2OCH3)—CH2CH2OCH3


1299.
N(CH3)CH(CH2OCH3)CH2CH2O—



CH2CH3


1300.
N(CH3)CH(CH2OCH3)CH2CH2O—



(CH2)2CH3


1301.
N(CH3)CH(CH2OCH3)CH2CH2O—



CH(CH3)2


1302.
N(CH3)CH(CH2OCH3)CH2CH2O—



CH2OCH3


1303.
N(CH2CH3)CH2OCH3


1304.
N(CH2CH3)CH2OCH2CH3


1305.
N(CH2CH3)CH2O(CH2)2CH3


1306.
N(CH2CH3)CH2OCH(CH3)2


1307.
N(CH2CH3)CH2OCH2OCH3


1308.
N(CH2CH3)CH2CH2OH


1309.
N(CH2CH3)CH2CH2OCH3


1310.
N(CH2CH3)CH2CH2OCH2CH3


1311.
N(CH2CH3)CH2CH2O(CH2)2CH3


1312.
N(CH2CH3)CH2CH2OCH(CH3)2


1313.
N(CH2CH3)CH2CH2OCH2OCH3


1314.
N(CH2CH3)CH2CH2CH2OH


1315.
N(CH2CH3)CH2CH2CH2OCH3


1316.
N(CH2CH3)CH2CH2CH2OCH2CH3


1317.
N(CH2CH3)CH2CH2CH2O—(CH2)2CH3


1318.
N(CH2CH3)CH2CH2CH2O—CH(CH3)2


1319.
N(CH2CH3)CH2CH2CH2O—CH2OCH3


1320.
N(CH2CH3)CH(CH3)OCH3


1321.
N(CH2CH3)CH(CH3)OCH2CH3


1322.
N(CH2CH3)CH(CH3)O(CH2)2CH3


1323.
N(CH2CH3)CH(CH3)OCH(CH3)2


1324.
N(CH2CH3)CH(CH3)OCH2OCH3


1325.
N(CH2CH3)CH(CH2CH)O—(CH2)2CH3


1326.
N(CH2CH3)CH(CH2CH)O—CH(CH3)2


1327.
N(CH2CH3)CH(CH2CH)O—CH2OCH3


1328.
N(CH2CH3)CH(CH2OCH3)OCH3


1329.
N(CH2CH3)CH(CH2OCH3)O—CH2CH3


1330.
N(CH2CH3)CH(CH2OCH3)O—



(CH2)2CH3


1331.
N(CH2CH3)CH(CH2OCH3)O—



CH(CH3)2


1332.
N(CH2CH3)CH(CH2OCH3)O—



CH2OCH3


1333.
N(CH2CH3)CH(CH3)CH2OH


1334.
N(CH2CH3)CH(CH3)CH2OCH3


1335.
N(CH2CH3)CH(CH3)CH2OCH2CH3


1336.
N(CH2CH3)CH(CH3)CH2O—



(CH2)2CH3


1337.
N(CH2CH3)CH(CH3)CH2O—CH(CH3)2


1338.
N(CH2CH3)CH(CH3)CH2O—CH2OCH3


1339.
N(CH2CH3)CH(CH2CH3)CH2OH


1340.
N(CH2CH3)CH(CH2CH3)CH2OCH3


1341.
N(CH2CH3)CH(CH2CH3)CH2O—



CH2CH3


1342.
N(CH2CH3)CH(CH2CH3)CH2O—



(CH2)2CH3


1343.
N(CH2CH3)CH(CH2CH3)CH2O—



CH(CH3)2


1344.
N(CH2CH3)CH(CH2CH3)CH2O—



CH2OCH3


1345.
N(CH2CH3)CH(CH2CH)CH2OH


1346.
N(CH2CH3)CH(CH2CH)CH2OCH3


1347.
N(CH2CH3)CH(CH2CH)CH2O—



CH2CH3


1348.
N(CH2CH3)CH(CH2CH)CH2O—



(CH2)2CH3


1349.
N(CH2CH3)CH(CH2CH)CH2O—



CH(CH3)2


1350.
N(CH2CH3)CH(CH2CH)CH2O—



CH2OCH3


1351.
N(CH2CH3)CH(CH2OCH3)CH2OH


1352.
N(CH2CH3)CH(CH2OCH3)CH2O—CH3


1353.
N(CH2CH3)CH(CH2OCH3)CH2O—



CH2CH3


1354.
N(CH2CH3)CH(CH2OCH3)CH2O—



(CH2)2CH3


1355.
N(CH2CH3)CH(CH2OCH3)CH2O—



CH(CH3)2


1356.
N(CH2CH3)CH(CH2OCH3)CH2O—



CH2OCH3


1357.
N(CH2CH3)CH2CH(CH3)OH


1358.
N(CH2CH3)CH2CH(CH3)OCH3


1359.
N(CH2CH3)CH2CH(CH3)OCH2CH3


1360.
N(CH2CH3)CH2CH(CH3)O—



(CH2)2CH3


1361.
N(CH2CH3)CH2CH(CH3)O—CH(CH3)2


1362.
N(CH2CH3)CH2CH(CH3)O—CH2OCH3


1363.
N(CH2CH3)CH2CH(CH2CH3)OH


1364.
N(CH2CH3)CH2CH(CH2CH3)OCH3


1365.
N(CH2CH3)CH2CH(CH2CH3)O—



CH2CH3


1366.
N(CH2CH3)CH2CH(CH2CH3)O—



(CH2)2CH3


1367.
N(CH2CH3)CH2CH(CH2CH3)O—



CH(CH3)2


1368.
N(CH2CH3)CH2CH(CH2CH3)O—



CH2OCH3


1369.
N(CH2CH3)CH2CH(CH2CH)OH


1370.
N(CH2CH3)CH2CH(CH2CH)OCH3


1371.
N(CH2CH3)CH2CH(CH2CH)O—



CH2CH3


1372.
N(CH2CH3)CH2C(CH2CH)(CH2CH)O—



(CH2)2CH3


1373.
N(CH2CH3)CH2CH(CH2CH)—



OCH(CH3)2


1374.
N(CH2CH3)CH2CH(CH2CH)O—



CH2OCH3


1375.
N(CH2CH3)CH2CH(CH2OCH3)OH


1376.
N(CH2CH3)CH2CH(CH2OCH3)O—CH3


1377.
N(CH2CH3)CH2CH(CH2OCH3)O—



CH2CH3


1378.
N(CH2CH3)CH2CH(CH2OCH3)O—



(CH2)2CH3


1379.
N(CH2CH3)CH2CH(CH2OCH3)O—



CH(CH3)2


1380.
N(CH2CH3)CH2CH(CH2OCH3)O—



CH2OCH3


1381.
N(CH2CH3)CH(CH3)CH2CH2OH


1382.
N(CH2CH3)CH(CH3)CH2CH2OCH3


1383.
N(CH2CH3)CH(CH3)CH2CH2O—



CH2CH3


1384.
N(CH2CH3)CH(CH3)CH2CH2O—



(CH2)2CH3


1385.
N(CH2CH3)CH(CH3)CH2CH2O—



CH(CH3)2


1386.
N(CH2CH3)CH(CH3)CH2CH2O—



CH2OCH3


1387.
N(CH2CH3)CH(CH2CH3)—CH2CH2OH


1388.
N(CH2CH3)CH(CH2CH3)—



CH2CH2OCH3


1389.
N(CH2CH3)CH(CH2CH3)—



CH2CH2OCH2CH3


1390.
N(CH2CH3)CH(CH2CH3)—



CH2CH2O(CH2)2CH3


1391.
N(CH2CH3)CH(CH2CH3)—



CH2CH2OCH(CH3)2


1392.
N(CH2CH3)CH(CH2CH3)—



CH2CH2OCH2OCH3


1393.
N(CH2CH3)C[(CH3)2)CH2CH2OH


1394.
N(CH2CH3)C[(CH3)2)—CH2CH2OCH3


1395.
N(CH2CH3)C[(CH3)2]CH2CH2O—



CH2CH3


1396.
N(CH2CH3)C[(CH3)2]CH2CH2O—



(CH2)2CH3


1397.
N(CH2CH3)C[(CH3)2]CH2CH2O—



CH(CH3)2


1398.
N(CH2CH3)C[(CH3)2]CH2CH2O—



CH2OCH3


1399.
N(CH2CH3)CH(CH2CH)—CH2CH2OH


1400.
N(CH2CH3)CH(CH2CH)—



CH2CH2OCH3


1401.
N(CH2CH3)CH(CH2CH)—



CH2CH2OCH2CH3


1402.
N(CH2CH3)CH(CH2CH)—



CH2CH2O(CH2)2CH3


1403.
N(CH2CH3)CH(CH2CH)—



CH2CH2OCH(CH3)2


1404.
N(CH2CH3)CH(CH2CH)—



CH2CH2OCH2OCH3


1405.
N(CH2CH3)CH(CH2OCH3)—



CH2CH2OH


1406.
N(CH2CH3)CH(CH2OCH3)—



CH2CH2OCH3


1407.
N(CH2CH3)CH(CH2OCH3)—



CH2CH2OCH2CH3


1408.
N(CH2CH3)CH(CH2OCH3)—



CH2CH2O(CH2)2CH3


1409.
N(CH2CH3)CH(CH2OCH3)—



CH2CH2OCH(CH3)2


1410.
N(CH2CH3)CH(CH2OCH3)—



CH2CH2OCH2OCH3


1411.
N(CH2OCH3)CH2OCH3


1412.
N(CH2OCH3)CH2OCH2CH3


1413.
N(CH2OCH3)CH2O(CH2)2CH3


1414.
N(CH2OCH3)CH2OCH(CH3)2


1415.
N(CH2OCH3)CH2OCH2OCH3


1416.
N(CH2OCH3)CH2CH2OH


1417.
N(CH2OCH3)CH2CH2OCH3


1418.
N(CH2OCH3)CH2CH2OCH2CH3


1419.
N(CH2OCH3)CH2CH2O(CH2)2CH3


1420.
N(CH2OCH3)CH2CH2OCH(CH3)2


1421.
N(CH2OCH3)CH2CH2OCH2OCH3


1422.
N(CH2OCH3)CH2CH2CH2OH


1423.
N(CH2OCH3)CH2CH2CH2OCH3


1424.
N(CH2OCH3)CH2CH2CH2O—CH2CH3


1425.
N(CH2OCH3)CH2CH2CH2O—



(CH2)2CH3


1426.
N(CH2OCH3)CH2CH2CH2O—



CH(CH3)2


1427.
N(CH2OCH3)CH2CH2CH2O—



CH2OCH3


1428.
N(CH2OCH3)CH(CH3)OCH3


1429.
N(CH2OCH3)CH(CH3)OCH2CH3


1430.
N(CH2OCH3)CH(CH3)O—(CH2)2CH3


1431.
N(CH2OCH3)CH(CH3)OCH(CH3)2


1432.
N(CH2OCH3)CH(CH3)OCH2OCH3


1433.
N(CH2OCH3)CH(CH2CH)O—



(CH2)2CH3


1434.
N(CH2OCH3)CH(CH2CH)O—



CH(CH3)2


1435.
N(CH2OCH3)CH(CH2CH)O—



CH2OCH3


1436.
N(CH2OCH3)CH(CH2OCH3)OCH3


1437.
N(CH2OCH3)CH(CH2OCH3)O—



CH2CH3


1438.
N(CH2OCH3)CH(CH2OCH3)O—



(CH2)2CH3


1439.
N(CH2OCH3)CH(CH2OCH3)O—



CH(CH3)2


1440.
N(CH2OCH3)CH(CH2OCH3)O—



CH2OCH3


1441.
N(CH2OCH3)CH(CH3)CH2OH


1442.
N(CH2OCH3)CH(CH3)CH2OCH3


1443.
N(CH2OCH3)CH(CH3)CH2O—CH2CH3


1444.
N(CH2OCH3)CH(CH3)CH2O—



(CH2)2CH3


1445.
N(CH2OCH3)CH(CH3)CH2O—



CH(CH3)2


1446.
N(CH2OCH3)CH(CH3)CH2O—



CH2OCH3


1447.
N(CH2OCH3)CH(CH2CH3)CH2OH


1448.
N(CH2OCH3)CH(CH2CH3)—CH2OCH3


1449.
N(CH2CH3)CH(CH2CH3)CH2O—



CH2CH3


1450.
N(CH2OCH3)CH(CH2CH3)CH2O—



(CH2)2CH3


1451.
N(CH2OCH3)CH(CH2CH3)CH2O—



CH(CH3)2


1452.
N(CH2OCH3)CH(CH2CH3)CH2O—



CH2OCH3


1453.
N(CH2OCH3)CH(CH2CH)CH2OH


1454.
N(CH2OCH3)CH(CH2CH)—CH2OCH3


1455.
N(CH2OCH3)CH(CH2CH)CH2O—



CH2CH3


1456.
N(CH2OCH3)CH(CH2CH)CH2O—



(CH2)2CH3


1457.
N(CH2OCH3)CH(CH2CH)CH2O—



CH(CH3)2


1458.
N(CH2OCH3)CH(CH2CH)CH2O—



CH2OCH3


1459.
N(CH2OCH3)CH(CH2OCH3)—CH2OH


1460.
N(CH2OCH3)CH(CH2OCH3)CH2O—



CH3


1461.
N(CH2OCH3)CH(CH2OCH3)CH2O—



CH2CH3


1462.
N(CH2OCH3)CH(CH2OCH3)CH2O—



(CH2)2CH3


1463.
N(CH2OCH3)CH(CH2OCH3)CH2O—



CH(CH3)2


1464.
N(CH2OCH3)CH(CH2OCH3)CH2O—



CH2OCH3


1465.
N(CH2OCH3)CH2CH(CH3)OH


1466.
N(CH2OCH3)CH2CH(CH3)OCH3


1467.
N(CH2OCH3)CH2CH(CH3)O—CH2CH3


1468.
N(CH2OCH3)CH2CH(CH3)O—



(CH2)2CH3


1469.
N(CH2OCH3)CH2CH(CH3)O—



CH(CH3)2


1470.
N(CH2OCH3)CH2CH(CH3)O—



CH2OCH3


1471.
N(CH2OCH3)CH2CH(CH2CH3)OH


1472.
N(CH2OCH3)CH2CH(CH2CH3)—OCH3


1473.
N(CH2OCH3)CH2CH(CH2CH3)O—



CH2CH3


1474.
N(CH2OCH3)CH2CH(CH2CH3)O—



(CH2)2CH3


1475.
N(CH2OCH3)CH2CH(CH2CH3)O—



CH(CH3)2


1476.
N(CH2OCH3)CH2CH(CH2CH3)O—



CH2OCH3


1477.
N(CH2OCH3)CH2CH(CH2CH)OH


1478.
N(CH2OCH3)CH2CH(CH2CH)—OCH3


1479.
N(CH2OCH3)CH2CH(CH2CH)O—



CH2CH3


1480.
N(CH2OCH3)CH2CH(CH2CH)—



(CH2CH)O—(CH2)2CH3


1481.
N(CH2OCH3)CH2CH(CH2CH)—



OCH(CH3)2


1482.
N(CH2OCH3)CH2CH(CH2CH)O—



CH2OCH3


1483.
N(CH2OCH3)CH2CH(CH2OCH3)—OH


1484.
N(CH2OCH3)CH2CH(CH2OCH3)O—



CH3


1485.
N(CH2OCH3)CH2CH(CH2OCH3)O—



CH2CH3


1486.
N(CH2OCH3)CH2CH(CH2OCH3)O—



(CH2)2CH3


1487.
N(CH2OCH3)CH2CH(CH2OCH3)O—



CH(CH3)2


1488.
N(CH2OCH3)CH2CH(CH2OCH3)O—



CH2OCH3


1489.
N(CH2OCH3)CH(CH3)CH2CH2OH


1490.
N(CH2OCH3)CH(CH3)—CH2CH2OCH3


1491.
N(CH2OCH3)CH(CH3)CH2CH2O—



CH2CH3


1492.
N(CH2OCH3)CH(CH3)CH2CH2O—



(CH2)2CH3


1493.
N(CH2OCH3)CH(CH3)CH2CH2O—



CH(CH3)2


1494.
N(CH2OCH3)CH(CH3)CH2CH2O—



CH2OCH3


1495.
N(CH2OCH3)CH(CH2CH3)—



CH2CH2OH


1496.
N(CH2OCH3)CH(CH2CH3)—



CH2CH2OCH3


1497.
N(CH2OCH3)CH(CH2CH3)—



CH2CH2OCH2CH3


1498.
N(CH2OCH3)CH(CH2CH3)—



CH2CH2O(CH2)2CH3


1499.
N(CH2OCH3)CH(CH2CH3)—



CH2CH2OCH(CH3)2


1500.
N(CH2OCH3)CH(CH2CH3)—



CH2CH2OCH2OCH3


1501.
N(CH2OCH3)C[(CH3)2]CH2CH2OH


1502.
N(CH2OCH3)C[(CH3)2—



CH2CH2OCH3


1503.
N(CH2OCH3)C[(CH3)2]CH2CH2O—



CH2CH3


1504.
N(CH2OCH3)C[(CH3)2]CH2CH2O—



(CH2)2CH3


1505.
N(CH2OCH3)C[(CH3)2]CH2CH2O—



CH(CH3)2


1506.
N(CH2OCH3)C[(CH3)2]CH2CH2O—



CH2OCH3


1507.
N(CH2OCH3)CH(CH2CH)—



CH2CH2OH


1508.
N(CH2OCH3)CH(CH2CH)—



CH2CH2OCH3


1509.
N(CH2OCH3)CH(CH2CH)—



CH2CH2OCH2CH3


1510.
N(CH2OCH3)CH(CH2CH)—



CH2CH2O(CH2)2CH3


1511.
N(CH2OCH3)CH(CH2CH)—



CH2CH2OCH(CH3)2


1512.
N(CH2OCH3)CH(CH2CH)—



CH2CH2OCH2OCH3


1513.
N(CH2OCH3)CH(CH2OCH3)—



CH2CH2OH


1514.
N(CH2OCH3)CH(CH2OCH3)—



CH2CH2OCH3


1515.
N(CH2OCH3)CH(CH2OCH3)—



CH2CH2OCH2CH3


1516.
N(CH2OCH3)CH(CH2OCH3)—



CH2CH2O(CH2)2CH3


1517.
N(CH2OCH3)CH(CH2OCH3)—



CH2CH2OCH(CH3)2


1518.
N(CH2OCH3)CH(CH2OCH3)—



CH2CH2OCH2OCH3


1519.
NHCH2CH(OCH3)2


1520.
NHCH2CH(OCH2CH3)2


1521.
NHCH(CH3)CH(OCH3)2


1522.
NHCH(CH3)CH(OCH2CH3)2


1523.
NHCH(CH2CH3)CH(OCH3)2


1524.
NHCH(CH2CH3)CH(OCH2CH3)2


1525.
NHCH(CH2CH2CH3)CH(OCH3)2


1526.
NHCH(CH2CH2CH3)-CH(OCH2CH3)2


1527.
NHCH2CH2CH(OCH3)2


1528.
NHCH2CH2CH(OCH2CH3)2


1529.
NHCH(CH3)CH2CH(OCH3)2


1530.
NHCH(CH3)CH2CH(OCH2CH3)2


1531.
NHCH(CH2CH3)CH2CH(OCH3)2


1532.
NHCH(CH2CH3)-CH2CH(OCH2CH3)2


1533.
NHCH(CH2CH2CH3)—CH2CH(OCH3)2


1534.
NHCH(CH2CH2CH3)—



CH2CH(OCH2CH3)2


1535.
NHCH2C(CH3)(OCH3)2


1536.
NHCH2C(CH3)(OCH2CH3)2


1537.
NHCH(CH3)C (CH3)(OCH3)2


1538.
NHCH(CH3)C(CH3)(OCH2CH3)2


1539.
NHCH(CH2CH3)C(CH3)(OCH3)2


1540.
NHCH(CH2CH3)-C(CH3)(OCH2CH3)2


1541.
NHCH(CH2CH2CH3)-C(CH3)(OCH3)2


1542.
NHCH(CH2CH2CH3)—



C(CH3)(OCH2CH3)2


1543.
NHCH2CH2C(CH3)(OCH3)2


1544.
NHCH2CH2C(CH3)(OCH2CH3)2


1545.
NNCH(CH3)CH2C(CH3)(OCH3)2


1546.
NHCH(CH3)—CH2C(CH3)(OCH2CH3)2


1547.
NHCH(CH2CH3)—CH2C(CH3)(OCH3)2


1548.
NHCH(CH2CH3)—



CH2C(CH3)(OCH2CH3)2


1549.
NHCH(CH2CH2CH3)—



CH2C(CH3)(OCH3)2


1550.
NHCH(CH2CH2CH3) —



CH2C(CH3)(OCH2CH3)2


1551.
NHCH2CH(SCH3)2


1552.
NHCH2CH(SCH2CH3)2


1553.
NHCH(CH3)CH(SCH3)2


1554.
NHCH(CH3)CH(SCH2CH3)2


1555.
NHCH(CH2CH3)CH(SCH3)2


1556.
NHCH(CH2CH3)CH(SCH2CH3)2


1557.
NHCH(CH2CH2CH3)CH(SCH3)2


1558.
NHCH(CH2CH2CH3)—CH(SCH2CH3)2


1559.
NHCH2CH2CH(SCH3)2


1560.
NHCH2CH2CH(SCH2CH3)2


1561.
NHCH(CH3)CH2CH(SCH3)2


1562.
NHCH(CH3)CH2CH(SCH2CH3)2


1563.
NHCH(CH2CH3)CH2CH(SCH3)2


1564.
NHCH(CH2CH3)—CH2CH(SCH2CH3)2


1565.
NHCH(CH2CH2CH3)—CH2CH(SCH3)2


1566.
NHCH(CH2CH2CH3) —



CH2CH(SCH2CH3)2


1567.
NHCH2CH2SCH3


1568.
NHCH2CH2SCH2CH3


1569.
NHCH2CH2S(CH2)2CH3


1570.
NHCH2CH2SCH(CH3)2


1571.
NHCH2CH2CH2SCH3


1572.
NHCH2CH2CH2SCH2CH3


1573.
NKCH2CH2CH2S(CH2)2CH3


1574.
NHCH2CH2CH2SCH(CH3)2


1575.
NHCH(CH3)CH2SCH3


1576.
NHCH(CH3)CH2SCH2CH3


1577.
NHCH(CH3)CH2S(CH2)2CH3


1578.
NHCH(CH3)CH2SCH(CH3)2


1579.
NHCH(CH3)CH2CH2SCH3


1580.
NHCH(CH3)CH2CH2SCH2CH3


1581.
NHCH(CH3)CH2CH2S(CH2)2CH3


1582.
NHCH(CH3)CH2CH2SCH(CH3)2


1583.
NHC[(CH3)2]CH2SCH3


1584.
NHC[(CH3)2]CH2SCH2CH3


1585.
NHC[(CH3)2]CH2S(CH2)2CH3


1586.
NHC[(CH3)2]CH2SCH(CH3)2


1587.
NHC[(CH3)2]CH2CH2SCH3


1588.
NHC[(CH3)2]CH2CH2SCH2CH3


1589.
NHC[(CH3)2]CH2CH2S(CH2)2CH3


1590.
NHC[(CH3)2]CH2CH2SCH(CH3)2


1591.
NHCH2CH2S(O)CH3


1592.
NHCH2CH2S(O)CH2CH3


1593.
NHCH2CH2S(O)(CH2)2CH3


1594.
NHCH2CH2S(O)CH(CH3)2


1595.
NHCH2CH2CH2S(O)CH3


1596.
NHCH2CH2CH2S(O)CH2CH3


1597.
NHCH2CH2CH2S(O)(CH2)2CH3


1598.
NHCH2CH2CH2S(O)CH(CH3)2


1599.
NHCH(CH3)CH2S(O)CH3


1600.
NHCH(CH3)CH2S(O)CH2CH3


1601.
NHCH(CH3)CH2S(O)(CH2)2CH3


1602.
NHCH(CH3)CH2S(O)CH(CH3)2


1603.
NHCH(CH3)CH2CH2S(O)CH3


1604.
NHCH(CH3)CH2CH2S(O)CH2CH3


1605.
NHCH(CH3)CH2CH2S(O)—(CH2)2CH3


1606.
NHCH(CH3)CH2CH2S(O)—CH(CH3)2


1607.
NHC[(CH3)2]CH2S(O)CH3


1608.
NHC[(CH3)23CH2S(O)CH2CH3


1609.
NHC[(CH3)2]CH2S(O)(CH2)2CH3


1610.
NHC[(CH3)2]CH2S(O)CH(CH3)2


1611.
NHC[(CH3)2]CH2CH2S(O)CH3


1612.
NHC[(CH3)2]CH2CH2S(O)CH2CH3


1613.
NHC[(CH3)2]CH2CH2S(O)—(CH2)2CH3


1614.
NHC[(CH3)2]CH2CH2S(O)—CH(CH3)2


1615.
NHCH2CH2S(O)2CH3


1616.
NHCH2CH2S(O)2CH2CH3


1617.
NHCH2CH2S(O)2(CH2)2CH3


1618.
NHCH2CH2S(O)2CH(CH3)2


1619.
NHCH2CH2CH2S(O)2CH3


1620.
NHCH2CH2CH2S(O)2CH2CH3


1621.
NHCH2CH2CH2S(O)2(CH2)2CH3


1622.
NHCH2CH2CH2S(O)2CH(CH3)2


1623.
NHCH(CH3)CH2S(O)2CH3


1624.
NHCH(CH3)CH2S(O)2CH2CH3


1625.
NHCH(CH3)CH2S(O)2(CH2)2CH3


1626.
NHCH(CH3)CH2S(O)2CH(CH3)2


1627.
NHCH(CH3)CH2CH2S(O)2CH3


1628.
NHCH(CH3)CH2CH2S(O)2CH2CH3


1629.
NHCH(CH3)CH2CH2S(O)2—(CH2)2CH3


1630.
NHCH(CH3)CH2CH2S(O)_CH(CH3)2


1631.
NHC[(CH3)2]CH2S(O)2CH3


1632.
NHC[(CH3)2)CH2S(O)2CH2CH3


1633.
NHC[(CH3)2]CH2S(O)2(CH2)2CH3


1634.
NHC[(CH3)2JCH2S(O)2CH(CH3)2


1635.
NHC[(CH3)2]CH2CH2S(O)2CH3


1636.
NHC[(CH3)2]CH2CH2S(O)2—CH2CH3


1637.
NHC[(CH3)2]CH2CH2S(O)2—



(CH2)2CH3


1638.
NHC[(CH3)2]CH2CH2S(O)2—CH(CH3)2


1639.
NHCH2CH2Si(OCH3)3


1640.
NHCH2CH2Si(OCH2CH3)3


1641.
NHCH(CH3)CH2Si(OCH3)3


1642.
NHCH(CH3)CH2Si(OCH2CH3)3


1643.
NHCH2CH2CH2Si(OCH3)3


1644.
NHCH2CH2CH2Si(OCH2CH3)3


1645.
NHCH(CH3)CH2CH2Si(OCH3)3


1646.
NHCH(CH3)CH2CH2-Si(OCH2CH3)3


 


1647.






 


1648.






 


1649.






 


1650.






 


1651.






 


1652.






 


1653.






 


1654.






 


1655.






 


1656.






 


1657.






 


1658.






 


1659.






 


1660.






 


1661.






 


1662.






 


1663.






 


1664.






 


1665.






 


1666.






 


1667.






 


1668.






 


1669.






 


1670.






 


1671.






 


1672.






 


1673.






 


1674.






 


1675.






 


1676.






 


1677.






 


1678.






 


1679.






 


1680.






 


1681.






 


1682.
HNCH2N═C(NH2)NH2


1683.
HNCH2CH2N═C(NH2)NH2


1684.
HNCH2CH2CH2N═C(NH2)NH2


1685.
HNCH(CH3)N═C(NH2)NH2


1686.
HNCH(CH3)CH2N═C(NH2)NH2


1687.
HNCH(CH3)CH2CH2N═C(NH2)NH2


1688.
HNCH2CH(CH3)N═C(NH2)NH2


1689.
HNCH2CH2CH(CH3)N═C(NH2)NH2


1690.
HNCH(CH3)CH(CH3)—N═C(NH2)NH2


1691.
HNCH(CH3)CH2CH(CH3)—



N═C(NH2)NH2


1692.
NHCH2-(2-pyridyl)


1693.
NHCH2CH2-(2-pyridyl)


1694.
NHCH2CH2CH2-(2-pyridyl)


1695.
NHCH(CH3)—(2-pyridyl)


1696.
NHCH(CH3)CH2-(2-pyridyl)


1697.
NHCH(CH3)CH2CH2-(2-pyridyl)


1698.
NHCH(CH2CH3)—(2-pyridyl)


1699.
NHCH(CH2CH3)CH2-(2-pyridyl)


1700.
NHCH(CH2CH3)CH2CH2-



(2-pyridyl)


1701.
NHCH2CH2O-(2-pyridyl)


1702.
NHCH2CH2CH2O-(2-pyridyl)


1703.
NHCH(CH3)O-(2-pyridyl)


1704.
NHCH(CH3)CH2O-(2-pyridyl)


1705.
NHCH(CH3)CH2CH2O-(2-pyridyl)


1706.
NHCH(CH2CH3)O-(2-pyridyl)


1707.
NHCH(CH2CH3)CH2O-(2-pyridyl)


1708.
NHCH(CH2CH3)CH2CH2O—



(2-pyridyl)


1709.
NHCH2-(3-pyridyl)


1710.
NHCH2CH2-(3-pyridyl)


1711.
NHCH2CH2CH2-(3-pyridyl)


1712.
NHCH(CH3)-(3-pyridyl)


1713.
NHCH(CH3)CH2-(3-pyridyl)


1714.
NHCH(CH3)CH2CH2-(3-pyridyl)


1715.
NHCH(CH2CH3)-(3-pyridyl)


1716.
NHCH(CH2CH3)CH2-(3-pyridyl)


1717.
NHCH(CH2CH3)CH2CH-



(3-pyridyl)


1718.
NHCH2CH2O-(3-pyridyl)


1719.
N HCH2CH2CH2O-(3-pyridyi)


1720.
NHCH(CH3)O-(3-pyridyl)


1721.
NHCH(CH3)CH2O-(3-pyridyl)


1722.
NHCH(CH3)CH2CH2O-(3-pyridyl)


1723.
NHCH(CH2CH3)O-(3-pyridyl)


1724.
NHCH(CH2CH3)CH2O-(3-pyridyl)


1725.
NHCH(CH2CH3)CH2CH2O-



(3-pyridyl)


1726.
NHCH2-(4-pyridyl)


1727.
NHCH2CH2-(4-pyridyl)


1728.
NHCH2CH2CH2-(4-pyridyl)


1729.
NHCH(CH3)—(4-pyridyl)


1730.
NHCH(CH3)CH2-(4-pyridyl)


1731.
N HCH(CH3)CH2CH2-(4-pyridyl)


1732.
NHCH(CH2CH3)-(4-pyridyl)


1733.
NHCH(CH2CH3)CH2-(4-pyridyl)


1734.
NHCH(CH2CH3)CH2CH2-



(4-pyridyl)


1735.
NHCH2CH2O-(4-pyridyl)


1736.
NHCH2CH2CH2O-(4-pyridyl)


1737.
NHCH(CH3)O-(4-pyridyl)


1738.
NHCH(CH3)CH2O-(4-pyridyl)


1739.
NHCH(CH3)CH2CH2O-(4-pyridyl)


1740.
NHCH(CH2CH3)O-(4-pyridyl)


1741.
NHCH(CH2CH3)CH2O-(4-pyridyl)


1742.
NHCH(CH2CH3)CH2CH2O-



(4-pyridyl)


1743.
NHCH2-(2-pyrimidyl)


1744.
NHCH2CH2-(2-pyrimidyl)


1745.
NHCH2CH2CH2-(2-pyrimidyl)


1746.
NHCH(CH3)-(2-pyrimidyl)


1747.
NHCH(CH3)CH2-(2-pyrimidyl)


1748.
NHCH(CH3)CH2CH2-(2-pyrimidyl)


1749.
NHCH(CH2CH3)-(2-pyrimidyl)


1750.
NHCH(CH2CH3)CH2-(2-pyrimidyl)


1751.
NHCH(CH2CH3)CH2CH2-



(2-pyrimidyl)


1752.
NHCH2CH2O-(2-pyrimidyl)


1753.
NHCH2CH2CH2O-(2-pyrimidyl)


1754.
NHCH(CH3)O-(2-pyrimidyl)


1755.
NHCH(CH3)CH2O-(2-pyrimidyl)


1756.
NHCH(CH3)CH2CH2O-(2-pyrimidyl)


1757.
NHCH(CH2CH3)O-(2-pyrimidyl)


1758.
NHCH(CH2CH3)CH2O-(2-pyrimidyl)


1759.
NHCH(CH2CH3)CH2CH2O-



(2-pyrimidyl)


1760.
NHCH2-(4-pyrimidyl)


1761.
NHCH2CH2-(4-pyrimidyl)


1762.
NHCH2CH2CH2-(4-pyrimidyl)


1763.
NHCH(CH3)-(4-pyrimidyl)


1764.
NHCH(CH3)CH2-(4-pyrimidyl)


1765.
NHCH(CH3)CH2CH2-(4-pyrimidyl)


1766.
NHCH(CH2CH3)-(4-pyrimidyl)


1767.
NHCH(CH2CH3)CH2-(4-pyrimidyl)


1768.
NHCH(CH2CH3)CH2CH2-



(4-pyrimidyl)


1769.
NHCH2CH2O-(4-pyrimidyl)


1770.
NHCH2CH2CH2O-(4-pyrimidyl)


1771.
NHCH(CH3)O-(4-pyrimidyl)


1772.
NHCH(CH3)CH2O-(4-pyrimidyl)


1773.
NHCH(CH3)CH2CH2O-(4-pyrimidyl)


1774.
NHCH(CH2CH3)O-(4-pyrimidyl)


1775.
NHCH(CH2CH3)CH2O-(4-pyrimidyl)


1776.
NHCH(CH2CH3)CH2CH2O-



(4-pyrimidyl)


1777.
NHCH2-(5-pyrimidyl)


1778.
NHCH2CH2-(5-pyrimidyl)


1779.
NHCH2CH2CH2-(5-pyrimidyl)


1780.
NHCH(CH3)-(5-pyrimidyl)


1781.
NHCH(CH3)CH2-(5-pyrimidyl)


1782.
NHCH(CH3)CH2CH2-(5-pyrimidyl)


1783.
NHCH(CH2CH3)—(5-pyrimidyl)


1784.
NHCH(CH2CH3)CH2-(5-pyrimidyl)


1785.
NHCH(CH2CH3)CH2CH2-



(5-pyrimidyl)


1786.
NHCH2CH2O-(5-pyrimidyl)


1787.
NHCH2CH2CH2O-(5-pyrimidyl)


1788.
NHCH(CH3)O-(5-pyrimidyl)


1789.
NHCH(CH3)CH2O-(5-pyrimidyl)


1790.
NHCH(CH3)CH2CH2O-(5-pyrimidyl)


1791.
NHCH(CH2CH3)O-(5-pyrimidyl)


1792.
NHCH(CH2CH3)CH2O-(5-pyrimidyl)


1793.
NHCH(CH2CH3)CH2CH2O-



(5-pyrimidyl)


1794.
NHCH2-(1,3,5-triazinyl)


1795.
NHCH2CH2-(1,3,5-triazinyl)


1796.
NHCH2CH2CH2-(1,3,5-triazinyl)


1797.
NHCH(CH3)—(1,3,5-triazinyl)


1798.
NHCH(CH3)CH2-(1,3,5-triazinyl)


1799.
NHCH(CH3)CH2CH2-



(1,3,5-triazinyl)


1800.
NHCH(CH2CH3)-(1,3,5-triazinyl)


1801.
NHCH(CH2CH3)CH2-



(1,3,5-triazinyl)


1802.
NHCH(CH2CH3)CH2CH2-



(1,3,5-triazinyl)


1803.
NHCH2CH2O-(1,3,5-triazinyl)


1804.
NHCH2CH2CH2O-(1,3,5-triazinyl)


1805.
NHCH(CH3)O-(1,3,5-triazinyl)


1806.
NHCH(CH3)CH2O-(1,3,5-triazinyl)


1807.
NHCH(CH3)CH2CH2O-



(1,3,5-triazinyl)


1808.
NHCH(CH2CH3)O-(1,3,5-triazinyl)


1809.
NHCH(CH2CH3)CH2O-



(1,3,5-triazinyl)


1810.
NHCH(CH2CH3)CH2CH2O-



(1,3,5-triazinyl)


1811.
NHCH2-(2-thiazolyl)


1812.
NHCH2CH2-(2-thiazolyl)


1813.
NHCH2CH2CH2-(2-thiazolyl)


1814.
NHCH(CH3)-(2-thiazolyl)


1815.
NHCH(CH3)CH2-(2-thiazolyl)


1816.
NHCH(CH3)CH2CH2-(2-thiazolyl)


1817.
NHCH(CH2CHs)—(2-thiazolyl)


1818.
NHCH(CH2CH3)CH2-(2-thiazolyl)


1819.
NHCH(CH2CH3)CH2CH2-



(2-thiazolyl)


1820.
NHCH2CH2O-(2-thiazolyl)


1821.
NHCH2CH2CH2O-(2-thiazolyl)


1822.
NHCH(CH3)O-(2-thiazolyl)


1823.
NHCH(CH3)CH2O-(2-thiazolyl)


1824.
NHCH(CH3)CH2CH2O-(2-thiazolyl)


1825.
NHCH(CH2CH3)O-(2-thiazolyl)


1826.
NHCH(CH2CH3)CH2O-(2-thiazolyl)


1827.
NHCH(CH2CH3)CH2CH2O-



(2-thiazolyl)


1828.
NHCH2-(4-thiazolyl)


1829.
NHCH2CH2-(4-thiazolyl)


1830.
NHCH2CHaCH2-(4-thiazolyl)


1831.
NHCH(CH3)-(4-thiazolyl)


1832.
NHCH(CH3)CH2-(4-thiazolyl)


1833.
NHCH(CH3)CH2CH2-(4-thiazolyl)


1834.
NHCH(CH2CH3)—(4-thiazolyl)


1835.
NHCH(CH2CH3)CH2-(4-thiazolyl)


1836.
NHCH(C H2CH3)CH2CH2-



(4-thiazolyl)


1837.
NHCH2CH2O-(4-thiazolyl)


1838.
NHCH2CH2CH2O-(4-thiazolyl)


1839.
NHCH(CH3)O-(4-thiazolyl)


1840.
NHCH(CH3)CH2O-(4-thiazolyl)


1841.
NHCH(CH3)CH2CH2O-(4-thiazolyl)


1842.
NHCH(CH2CH3)O-(4-thiazolyl)


1843.
NHCH(CH2CH3)CH2O-(4-thiazolyl)


1844.
NHCH(CH2CH3)CH2CH2O-



(4-thiazolyl)


1845.
NHCH2-(5-thiazolyl)


1846.
NHCH2CH2-(5-thiazolyl)


1847.
NHCH2CH2CH2-(5-thiazolyl)


1848.
NHCH(CH3)-(5-thiazolyl)


1849.
NHCH(CH3)CH2-(5-thiazolyl)


1850.
NHCH(CH3)CH2CH2-(5-thiazolyl)


1851.
NHCH(CH2CH3)-(5-thiazolyl)


1852.
NHCH(CH2CH3)CH2-(5-thiazolyl)


1853.
NHCH(CH2CH3)CH2CH2-



(5-thiazolyl)


1854.
NHCH2CH2O-(5-thiazolyl)


1855.
NHCH2CH2CH2O-(5-thiazolyl)


1856.
NHCH(CH3)O-(5-thiazolyl)


1857.
NHCH(CH3)CH2O-(5-thiazolyl)


1858.
NHCH(CH3)CH2CH2O-(5-thiazolyl)


1859.
NHCH(CH2CH3)O-(5-thiazolyl)


1860.
NHCH(CH2CH3)CH2O-(5-thiazolyl)


1861.
NHCH(CH2CH3)CH2CH2O-



(5-thiazolyl)


1862.
NHCH2-(2-furyl)


1863.
NHCH2CH2-(2-furyl)


1864.
NHCH2CH2CH2-(2-furyl)


1865.
NHCH(CH3)—(2-furyl)


1866.
NHCH(CH3)CH2-(2-furyl)


1867.
NHCH(CH3)CH2CH2-(2-furyl)


1868.
NHCH(CH2CH3)-(2-furyl)


1869.
NHCH(CH2CH3)CH2-(2-furyl)


1870.
NHCH(CH2CH3)CH2CH2-



(2-furyl)


1871.
NHCH2CH2O-(2-furyl)


1872.
NHCH2CH2CH2O-(2-furyl)


1873.
NHCH(CH3)O-(2-furyl)


1874.
NHCH(CH3)CH2O-(2-furyl)


1875.
NHCH(CH3)CH2CH2O-(2-furyl)


1876.
NHCH(CH2CH3)O-(2-furyl)


1877.
NHCH(CH2CH3)CH2O-(2-furyl)


1878.
NHCH(CH2CH3)CH2CH2O-



(2-furyl)


1879.
NHCH2-(3-furyl)


1880.
NHCH2CH2-(3-furyl)


1881.
NHCH2CH2CH2-(3-furyl)


1882.
NHCH(CH3)—(3-furyl)


1883.
NHCH(CH3)CH2-(3-furyl)


1884.
NHCH(CH3)CH2CH2-(3-furyl)


1885.
NHCH(CH2CH3)—(3-furyl)


1886.
NHCH(CH2CH3)CH2-(3-furyl)


1887.
NHCH(CH2CH3)CH2CH2-



(3-furyl)


1888.
NHCH2CH2O-(3-furyl)


1889.
NHCH2CH2CH2O-(3-furyl)


1890.
NHCH(CH3)O-(3-furyl)


1891.
NHCH(CH3)CH2O-(3-furyl)


1892.
NHCH(CH3)CH2CH2O-(3-furyl)


1893.
NHCH(CH2CHs)O-(3-furyl)


1894.
NHCH(CH2CH3)CH2O-(3-furyl)


1895.
NHCH(CH2CH3)CH2CH2O-



(3-furyl)


1896.
NHCH2-(2-thienyl)


1897.
NHCH2CH2-(2-thienyl)


1898.
NHCH2CH2CH2-(2-thienyl)


1899.
NHCH(CH3)—(2-thienyl)


1900.
NHCH(CH3)CH2-(2-thienyl)


1901.
NHCH(CH3)CH2CH2-(2-thienyl)


1902.
NHCH(CH2CH3)—(2-thienyl)


1903.
NHCH(CH2CH3)CH2-(2-thienyl)


1904.
NHCH(CH2CH3)CH2CH2-



(2-thienyl)


1905.
NHCH2CH2O-(2-thienyl)


1906.
NHCH2CH2CH2O-(2-thienyl)


1907.
NHCH(CH3)O-(2-thienyl)


1908.
NHCH(CH3)CH2O-(2-thienyl)


1909.
NHCH(CH3)CH2CH2O-(2-thienyl)


1910.
NHCH(CH2CH3)O-(2-thienyl)


1911.
NHCH(CH2CH3)CH2O-(2-thienyl)


1912.
NHCH(CH2CH3)CH2CH2O-



(2-thienyl)


1913.
NHCH2-(3-thienyl)


1914.
NHCH2CH2-(3-thienyl)


1915.
NHCH2CH2CH2-(3-thienyl)


1916.
NHCH(CH3)—(3-thienyl)


1917.
NHCH(CH3)CH2-(3-thienyl)


1918.
NHCH(CH3)CH2CH2-(3-thienyl)


1919.
NHCH(CH2CH3)—(3-thienyl)


1920.
NHCH(CH2CH3)CH2-(3-thienyl)


1921.
NHCH(CH2CH3)CH2CH2-



(3-thienyl)


1922.
NHCH2CH2O-(3-thienyl)


1923.
NHCH2CH2CH2O-(3-thienyl)


1924.
NHCH(CH3)O-(3-thienyl)


1925.
NHCH(CH3)CH2O-(3-thienyl)


1926.
NHCH(CH3)CH2CH2O-(3-thienyl)


1927.
NHCH(CH2CH3)O-(3-thienyl)


1928.
NHCH(CH2CH3)CH2O-(3-thienyl)


1929.
NHCH(CH2CH3)CH2CH2O-



(3-thienyl)


1930.
NHCH2-(1-imidazolyl)


1931.
NHCH2CH2-(1-imidazolyl)


1932.
NHCH2CH2CH2-(1-imidazolyl)


1933.
NHCH(CH3)—(1 -imidazolyl)


1934.
NHCH(CH3)CH2-(1 -imidazolyl)


1935.
NHCH(CH3)CH2CH2-(1 -imidazolyl)


1936.
NHCH2CH(CH)3CH2-(1 -imidazolyl)


1937.
NHCH2CH2CH(CH)3-(1-imidazolyl)


1938.
NHCH(CH2CH3)-(1-imidazolyl)


1939.
NHCH(CH2CH3)CH2-(1 -imidazolyl)


1940.
NHCH(CH2CH3)CH2CH2-



(1-imidazolyl)


1941.
NHCH2CH2O-(1-imidazolyl)


1942.
NHCH2CH2CH2O-(1-imidazolyl)


1943.
NHCH(CH3)O-(1-imidazolyl)


1944.
NHCH(CH3)CH2O-(1-imidazolyl)


1945.
NHCH(CH3)CH2CH2O-



(1-imidazolyl)


1946.
NHCH(CH2CH3)O-(1-imidazolyl)


1947.
NHCH(CH2CH3)CH2O-



(1-imidazolyl)


1948.
NHCH(CH2CH3)CH2CH2O-



(1-imidazolyl)


1949.
NHCH2-(1-[1,2,4-triazolyl])


1950.
NHCH2CH2-(1-[1,2,4-triazolyl])


1951.
NHCH2CH2CH2-(1-[1,2,4-triazolyl])


1952.
NHCH(CH3)-(1-[1,2,4-triazolyl])


1953.
NHCH(CH3)CH2-(1-[1,2,4-triazolyl])


1954.
NHCH(CH3)CH2CH2-



(1-[1,2,4-triazolyl])


1955.
NHCH(CH2CH3)-(1-[1,2,4-triazolyl])


1956.
NHCH(CH2CH3)CH2-



(1-[1,2,4-triazolyl])


1957.
NHCH(CH2CH3)CH2CH2-



(1-[1,2,4-triazolyl])


1958.
NHCH2CH(CH)3CH2-



(1-[1,2,4-triazolyl])


1959.
NHCH2CH2CH(CH)3-



(1-[1,2,4-triazolyl])


1960.
NHCH2CH2O-(1-[1,2,4-triazolyl])


1961.
NHCH2CH2CH2O-



(1-[1,2,4-triazolyl])


1962.
NHCH(CH3)O-(1-[1,2,4-triazolyl])


1963.
NHCH(CH3)CH2O-



(1-[1,2,4-triazolyl])


1964.
NHCH(CH3)CH2CH2O-



(1-[1,2,4-triazolyl])


1965.
NHCH(CH2CH3)O-(1-[1,2,4-



triazolyl])


1966.
NHCH(CH2CH3)CH2O-



(1-[1,2,4-triazolyl])


1967.
NHCH(CH2CH3)CH2CH2O-



(1-[1,2,4-triazolyl])


1968.
NHCH2-(1-tetrazolyl)


1969.
NHCH2CH2-(1-tetrazolyl)


1970.
NHCH2CH2CH2-(1-tetrazolyl)


1971.
NHCH(CH3)-(1-tetrazolyl)


1972.
NHCH(CH3)CH2-(1-tetrazolyl)


1973.
NHCH(CH3)CH2CH2-(1-tetrazolyl)


1974.
NHCH(CH2CH3)—(1-tetrazolyl)


1975.
NHCH(CH2CH3)CH2-(1-tetrazolyl)


1976.
NHCH(CH2CH3)CH2CH2-



(1-tetrazolyl)


1977.
NHCH2CH2O-(1-tetrazolyl)


1978.
NHCH2CH2CH2O-(1-tetrazolyl)


1979.
NHCH(CH3)O-(1-tetrazolyl)


1980.
NHCH(CH3)CH2O-(1-tetrazolyl)


1981.
NHCH(CH3)CH2CH2O-



(1-tetrazolyl)


1982.
NHCH(CH2CH3)O-(1-tetrazolyl)


1983.
NHCH(CH2CH3)CH2O-



(1-tetrazolyl)


1984.
NHCH(CH2CH3)CH2CH2O-



(1-tetrazolyl)


1985.
NHCHO


1986.
NHCOCH3


1987.
NHCOCH2CH3


1988.
NHCO(CH2)2CH3


1989.
NHCO(CH2)3CH3


1990.
NHCOCH(CH3)2


1991.
NHCOCH2CH(CH3)2


1992.
NHCOC(CH3)3


1993.
NHCOCF3


1994.
NHCOCF2CF3


1995.
NHCO(CF2)2CF3


1996.
NHCOCH(CH)CH3


1997.
NHCOCH(OCH3)CH3


1998.
NHCOCH2CH(CH)CH3


1999.
NHCOCH2CH(OCH3)CH3


2000.
NHCOCH═CH2


2001.
NHCOCH═CHCH3


2002.
NHCOCH2CH═CH2


2003.
NHCOCH(CH3)CH═CH2


2004.
NHCOC≡OH


2005.
NHCOC≡CCH3


2006.
NHCOCH2C≡OH


2007.
NHCOCH(CH3)C≡OH


2008.
NHCOC≡CCl


2009.
NHCOC≡CCH2OH


2010.
NHCOC≡CCH2OCH3


2011.
N(CH3)CHO


2012.
N(CH3)COCH3


2013.
N(CH3)COCH2CH3


2014.
N(CH3)CO(CH2)2CH3


2015.
N(CH3)CO(CH2)3CH3


2016.
N(CH3)COCH(CH3)2


2017.
N(CH3)COCH2CH(CH3)2


2018.
N(CH3)COC(CH3)3


2019.
N(CH3)COCF3


2020.
N(CH3)COCF2CF3


2021.
N(CH2CH3)CHO


2022.
N(CH2CH3)COCH3


2023.
N(CH2CH3)COCH2CH3


2024.
N(CH2CH3)CO(CH2)2CH3


2025.
N(CH2CH3)CO(CH2)2CH3


2026.
N(CH2CH3)COCH(CH3)2


2027.
N(CH2CH3)COCH2CH(CH3)2


2028.
N(CH2CH3)COC(CH3)3


2029.
N(CH2CH3)COCF3


2030.
N(CH2CH3)COCF2CF3


2031.
N(CH(CH3)2)CHO


2032.
N(CH(CH3)2)COCH3


2033.
N(CH(CH3)2)COCH2CH3


2034.
N(CH(CH3)2)CO(CH2)2CH3


2035.
N(CH(CH3)2)CO(CH2)3CH3


2036.
N(CH(CH3)2)COCH(CH3)2


2037.
N(CH(CH3)2)COCH2CH(CH3)2


2038.
N(CH(CH3)2)COO(CH3)3


2039.
N(CH(CH3)2)COCF3


2040.
N(CH(CH3)2COCF2CF3


2041.
N(CH(CH2CH)CH3)CHO


2042.
N(CH(CH2CH)CH3)COCH3


2043.
N(CH(CH2CH)CH3)COCH2CH3


2044.
N(CH(CH2CH)CH3)CO(CH2)2CH3


2045.
N(CH(CH2CH)CH3)CO(CH2)3CH3


2046.
N(CH(CH2CH)CH3)COCH(CH3)2


2047.
N(CH(CH2CH)CH3)COCH2CH—(CH3)2


2048.
N(CH(CH2CH)CH3)COC(CH3)3


2049.
N(CH(CH2CH)CH3)COCF3


2050.
N(CH(CH2CH)CH3)COCF2CF3


2051.
N(CH(CH2OCH3)CH3)CHO


2052.
N(CH(CH2OCH3)CH3)COCH3


2053.
N(CH(CH2OCH3)CH3)COCH2CH3


2054.
N(CH(CH2OCH3)CH3)CO—(CH2)2CH3


2055.
N(CH(CH2OCH3)CH3)CO—(CH2)3CH3


2056.
N(CH(CH2OCH3)CH3)CO—CH(CH3)2


2057.
N(CH(CH2OCH3)CH3)CO—



CH2CH(CH3)2


2058.
N(CH(CH2OCH3)CH3)COC(CH3)3


2059.
N(CH(CH2OCH3)CH3)COCF3


2060.
N(CH(CH2OCH3)CH3)COCF2CF3


2061.
NHCOOCH3


2062.
NHCOOCH2CH3


2063.
NHCOO(CH2)2CH3


2064.
NHCOO(CH2)3CH3


2065.
NHCOOCH(CH3)2


2066.
NHCOOCH2CH(CH3)2


2067.
NHCOOC(CH3)3


2068.
NHCOOCH2CF3


2069.
NHCOOCH2CHOCH3


2070.
N(CH3)COOCH3


2071.
N(CH3)COOCH2CH3


2072.
N(CH3)COO(CH2)2CH3


2073.
N(CH3)COO(CH2)3CH3


2074.
N(CH3)COOCH(CH3)2


2075.
N(CH3)COOCH2CH(CH3)2


2076.
N(CH3)COOC(CH3)3


2077.
N(CH3)COOCH2CF3


2078.
N(CH3)COOCH2CHOCH3


2079.
N(CH2CH3)COOCH3


2080.
N(CH2CH3)COOCH2CH3


2081.
N(CH2CH3)COO(CH2)2CH3


2082.
N(CH2CH3)COO(CH2)3CH3


2083.
N(CH2CH3)COOCH(CH3)2


2084.
N(CH2CH3)COOCH2CH(CH3)2


2085.
N(CH2CH3)COOC(CH3)3


2086.
N(CH2CH3)COOCH2CF3


2087.
N(CH2CH3)COOCH2CHOCH3


2088.
N(CH(CH3)2)COOCH3


2089.
N(CH(CH3)2)COOCH2CH3


2090.
N(CH(CH3)2)COO(CH2)2CH3


2091.
N(CH(CH3)2)COO(CH2)3CH3


2092.
N(CH(CH3)2)COOCH(CH3)2


2093.
N(CH(CH3)2)COOCH2CH(CH3)2


2094.
N(CH(CH3)2)COOC(CH3)3


2095.
N(CH(CH3)2)COOCH2CF3


2096.
N(CH(CH3)2)COOCH2CHOCH3


2097.
N(CH(CH2CH)CH3)COOCH3


2098.
N(CH(CH2CH)CH3)COOCH2CH3


2099.
N(CH(CH2CH)CH3)COO—(CH2)2CH3


2100.
N(CH(CH2CH)CH3)COO—(CH2)3CH3


2101.
N(CH(CH2CH)CH3)COOCH(CH3)2


2102.
N(CH(CH2CH)CH3)COO—



CH2CH(CH3)2


2103.
N(CH(CH2CH)CH3)COOC(CH3)3


2104.
N(CH(CH2CH)CH3)COOCH2CF3


2105.
N(CH(CH2CH)CH3)COO—



CH2CHOCH3


2106.
N(CH(CH2OCH3)CH3)COOCH3


2107.
N(CH(CH2OCH3)CH3)COO—CH2CH3


2108.
N(CH(CH2OCH3)CH3)COO—



(CH2)2CH3


2109.
N(CH(CH2OCH3)CH3)COO—



(CH2)3CH3


2110.
N(CH(CH2OCH3)CH3)COO—



CH(CH3)2


2111.
N(CH(CH2OCH3)CH3)COO—



CH2CH(CH3)2


2112.
N(CH(CH2OCH3)CH3)COO—C(CH3)3


2113.
N(CH(CH2OCH3)CH3)COO—CH2CF3


2114.
N(CH(CH2OCH3)CH3)COO—



CH2CHOCH3


2115.
NHCONHCH3


2116.
NHCONHCH2CH3


2117.
NHCONH(CH2)2CH3


2118.
NHCONH(CH2)3CH3


2119.
NHCONHCH(CH3)2


2120.
NHCONHCH2CH(CH3)2


2121.
NHCONHC(CH3)3


2122.
NHCONHCH2CF3


2123.
NHCONHCH2CHOCH3


2124.
N(CH3)CONHCH3


2125.
N(CH3)CONHCH2CH3


2126.
N(CH2CH3)CONHCH3


2127.
N(CH2CH3)CONHCH2CH3


2128.
N(CH(CH3)2)CONHCH3


2129.
N(CH(CH3)2)CONHCH2CH3


2130.
N(CH(CH2CH)CH3)CONHCH3


2131.
N(CH(CH2CH)CH3)CONHCH2CH3


2132.
N(CH(CH2OCH3)CH3)CONHCH3


2133.
N(CH(CH2OCH3)CH3)CONH—



CH2CH3


2134.
NHCON(CH3)2


2135.
NHCON(CH2CH3)2


2136.
NHCON(CH3)(CH2)2CH3


2137.
NHCON(CH3)(CH2)3CH3


2138.
NHCON(CH3)CH(CH3)2


2139.
NHCON(CH3)CH2CH(CH3)2


2140.
NHCON(CH3)C(CH3)3


2141.
NHCON(CH2CF3)2


2142.
NHCON(CH2CHOCH3)2


2143.
NHSONHCH3


2144.
NHSONHCH2CH3


2145.
NHSONH(CH2)2CH3


2146.
NHSONH(CH2)3CH3


2147.
NHSONHCH(CH3)2


2148.
NHSONHCH2CH(CH3)2


2149.
NHSONHC(CH3)3


2150.
NHSONHCH2CF3


2151.
NHSONHCH2CHOCH3


2152.
NHSON(CH3)2


2153.
NHSON(CH2CH3)2


2154.
NHSON(CH3)(CH2)2CH3


2155.
NHSON(CH3)(CH2)3CH3


2156.
NHSON(CH3)CH(CH3)2


2157.
NHSON(CH3)CH2CH(CH3)2


2158.
NHSON(CH3)C(CH3)3


2159.
NHSON(CH2CF3)2


2160.
NHSON(CH2CHOCH3)2


2161.
NHS(O)2NHCH3


2162.
NHS(O)2NHCH2CH3


2163.
NHS(O)2NH(CH2)2CH3


2164.
NHS(O)2NH(CH2)3CH3


2165.
NHS(O)2NHCH(CH3)2


2166.
NHS(O)2NHCH2CH(CH3)2


2167.
NHS(O)2NHC(CH3)3


2168.
NHS(O)2NHCH2CF3


2169.
NHS(O)2NHCH2CHOCH3


2170.
NHS(O)2N(CH3)2


2171.
NHS(O)2N(CH2CH3)2


2172.
NHS(O)2N(CH3)(CH2)2CH3


2173.
NHS(O)2N(CH3)(CH2)3CH3


2174.
NHS(O)2N(CH3)CH(CH3)2


2175.
NHS(O)2N(CH3)CH2CH(CH3)2


2176.
NHS(O)2N(CH3)C(CH3)3


2177.
NHS(O)2N(CH2CF3)2


2178.
NHS(O)2N(CH2CHOCH3)2


 


2179.






 


2180.






 


2181.






 


2182.






 


2183.
N═CHNH2


2184.
N═CHNH(CH3)


2185.
N═CHN(CH3)2


2186.
N═CHNH(CH2CH3)


2187.
N═CHN(CH2CH3)2


2188.
N═CHNCH3(CH2CH3)


2189.
N═C(CH3)NH2


2190.
N═C(CH3)NH(CH3)


2191.
N═C(CH3)N(CH3)2


2192.
N═C(CH3)NH(CH2CH3)


2193.
N═C(CH3)N(CH2CH3)2


2194.
N═C(CH3)NCH3(CH2CH3)


2195.
N═C(CH2CH3)NH2


2196.
N═C(CH2CH3)NH(CH3)


2197.
N═C(CH2CH3)N(CH3)2


2198.
N═C(CH2CH3)NH(CH2CH3)


2199.
N═C(CH2CH3)N(CH2CH3)2


2200.
N═C(CH2CH3)NCH3(CH2CH3)


2201.
N═C(NH2)NH2


2202.
N═C(NH2)NH(CH3)


2203.
N═C(NH2)N(CH3)2


2204.
N═C(NH2)NH(CH2CH3)


2205.
N═C(NH2)N(CH2CH3)2


2206.
N═C(NH2)NCH3(CH2CH3)


2207.
N═C(NH(CH3))NH(CH3)


2208.
N ̃C(NH(CH3))N(CH3)2


2209.
N═C(NH(CH3))NH(CH2CH3)


2210.
N ̃C(NH(CH3))N(CH2CH3)2


2211.
N═C(NH(CH3))NCH3(CH2CH3)


2212.
N═C(NH(CH2CH3))NH(CH3)


2213.
N═C(NH(CH2CH3))N(CH3)2


2214.
N═C(NH(CH2CH3))NH(CH2CH3)


2215.
N═C(NH(CH2CH3))N(CH2CH3)2


2216.
N═C(NH(CH2CH3))NCH3(CH2CH3)


 


2217.






 


2218.






 


2219.






 


2220.






 


2221.






 


2222.






 


2223.






 


2224.






 


2225.






 


2226.






 


2227.






 


2228.






 


2229.






 


2230.






 


2231.






 


2232.






 


2233.






 


2234.






 


2235.






 


2236.






 


2237.













The invention especially relates to a the use of at least one compound of the formula I or a salt thereof for protecting a plant against attack or infestation by a phytopathogenic organism, especially a microorganism, especially a fungal organism (preferably selected from the group consisting of Ascomycetes, Basidiomycetes, Oomycetes and Fungi imperfecti), a bacterium, a virus or a nematode; said compound or salt being selected from the compounds given in Table A or especially in table 59, comprising administering said compound and/or salt to one or more selected from the group consisting of a plant, a part of a plant, seeds and the site of a plant.
Preferred are compounds of formula I, wherein n=0, R1=halogen or haloalkoxy, each of R2 to R5 is hydrogen and R6 is lower alkylamino wherein the lower alkyl moiety is substituted by one or more (preferably 1 to 3, especially 1 or 2) substitutents independently selected from the group consisting of unsubstituted amino, N-mono- or N,N-di-(lower alkyl)-amino, (lower alkoxy)-lower alkoxy, lower alkoxycarbonylamino, hydroxy-lower alkoxycarbonylamino, lower alkoxy-lower alkoxycarbonylamino, morpholinyl, hydroxy-lower alkylamino, hydroximino, alkoximino, guanidyl, lower alkanoylamino, hydroxy-lower alkanoylamino, lower alkoxy-lower alkanoylamino, halo-lower alkanoylamino, lower alkylaminocarbonylamino, hydroxy-lower alkylaminocarbonylamino, lower alkoxy-lower alkylaminocarbonylamino, amidino, lower alkylcarbonyldioxy (=lower alkoxycarbonyloxy), hydroxy-lower alkoxycarbonyloxy, lower alkoxy-lower alkoxycarbonyloxy, lower alkanoyloxy, halo-lower alkanoyloxy, hydroxy-lower alkanoyloxy, lower alkoxy-lower alkanoyloxy, hydroxy, lower alkoxy, lower alkenyloxy, lower alkinyloxy, lower haloalkoxy, piperazinyl, lower alkanoyl-piperazinyl (including formylpiperazinyl) and optionally substituted heteroaryloxy, or a salt thereof.
More preferred is a compound of formula I, wherein n=0, R1=chlorine or haloalkoxy, each of R2 to R5 is hydrogen and R6 is alkoxyalkylamino, or a salt thereof.
Especially preferred are compounds 4, 5, 12, 13, 14, 15, 32 and 40 of table 59.
The present invention also relates to the novel compounds of formula I mentioned hereinbefore and hereinafter, or salts thereof;
Especially preferred are the compounds with n=1 (N-oxides) of formula I, or the salts thereof.
Especially preferred is also a compound of formula I selected from the group of compounds provided in tables 1 to 58, or a salt thereof, or that total group of compounds, with the exception of

    N-(3-trifluoromethyl-phenyl)-4-[2-(3-hydroxy-propyl-amino)-4-pyridyl]-2-pyrimidine-amine,
    N-(3-chloro-phenyl)-4-[2-(3-hydroxy-propyl-amino)-4-pyridyl]-2-pyrimidine-amine,
    N-(3-chloro-phenyl)-4-[2-(2-hydroxy-propyl-amino)-4-pyridyl]-2-pyrimidine-amine,
    N-(3-chloro-phenyl)-4-[2-(2-carboxy-ethyl-amino)-4-pyridyl]-2-pyrimidine-amine,
    N-(3-chloro-phenyl)-4-[2-(2-carbamoyl-ethyl-amino)-4-pyridyl]-2-pyrimidine-amine,
    N-(3-chloro-phenyl)-4-[2-(2-ethoxycarbonyl-ethyl-amino)-4-pyridyl]-2-pyrimidine-amine,
    N-(3-trifluoromethyl-phenyl)-4-[2-(2-hydroxy-propyl-amino)-4-pyridyl]-2-pyrimidine-amine,
    N-(3-trifluoromethyl-phenyl)-4-[2-(2-carboxy-ethyl-amino)-4-pyridyl]-2-pyrimidine-amine,
    N-(3-trifluoromethyl-phenyl)-4-[2-(2-carbamoyl-ethyl-amino)-4-pyridyl]-2-pyrimidine-amine,
    N-(3-trifluoromethyl-phenyl)-4-[2-(2-ethoxycarbonyl-ethyl-amino)-4-pyridyl]-2-pyrimidine-amine,
    N-(3-chloro-phenyl)-4-[2-(2-imidazol-1-yl-ethyl-amino)-4-pyridyl]-2-pyrimidine-amine,
    N-(3-chloro-phenyl)-4-[2-(2-acetamido-ethyl-amino)-4-pyridyl]-2-pyrimidine-amine,
    N-(3-chloro-phenyl)-4-(2-hydrazino-4-pyridyl)-2-pyrimidine-amine,
    N-(3-chloro-phenyl)-4-[2-(2-guanidyl-ethyl-amino)-4-pyridyl]-2-pyrimidine-amine,
    N-(3-chloro-phenyl)-4-[2-{2-(methylamino-carbonylamino)-ethyl-amino}-4-pyridyl]-2-pyrimidine-amine,
    N-(3-chloro-phenyl)-4-[2-(2-amidino-ethyl-amino)-4-pyridyl]-2-pyrimidine-amine,
    N-(3-chloro-phenyl)-4-[2-{2-(N-hydroxy-carbamoyl)-ethyl-amino}-4-pyridyl]-2-pyrimidine-amine,
    N-(3-trifluormethyl-phenyl)-4-[2-{2-(N-hydroxy-carbamoyl)-ethyl-amino}-4-pyridyl]-2-pyrimidine-amine,
    N-(3-chloro-phenyl)-4-[2-(2-amino-ethyl-amino)-4-pyridyl]-2-pyrimidine-amine,
    N-(3-trifluoromethyl-phenyl)-4-[2-(2-amino-ethyl-amino)-4-pyridyl]-2-pyrimidine-amine,
    N-(3-chloro-phenyl)-4-[2-(2-hydroxy-ethyl-amino)-4-pyridyl]-2-pyrimidine-amine,
    N-(3-chloro-phenyl)-4-[2-(1-piperazinyl)-4-pyridyl]-2-pyrimidine-amine,
    N-(3-chloro-phenyl)-4-[2-{2-(4-morpholinyl)-ethyl-amino}-4-pyridyl]-2-pyrimidine-amine,
    N-(3-chloro-phenyl)-4-[2-(4-morpholinyl)-4-pyridyl]-2-pyrimidine-amine,
    N-(3-chloro-phenyl)-4-(2-n-propylamino-4-pyridyl)-2-pyrimidine-amine,
    N-(3-chloro-phenyl)-4-[2-(n-1-butylamino)-4-pyridyl]-2-pyrimidine-amine,
    N-(3-chloro-phenyl)-4-(2-amino-4-pyridyl)-2-pyrimidine-amine, and
    N-(3-chloro-phenyl)-4-(2-dimethylamino-4-pyridyl)-2-pyrimidine-amine, or a salt thereof.


Preferred is also a compound of the formula I selected from the compounds mentioned in tables 2, 4, 5, 8, 31, 33, 34 and 37, or a salt thereof, or the whole group of compounds mentioned in said table.
Especially preferred is a compound of the formula I selected from the compounds of formula I mentioned in table 59, or a salt thereof, or the whole group of compounds in that table, or a salt of any thereof, with the exception of

    N-(3-chloro-phenyl)-4-[2-(3-hydroxy-propyl-amino)-4-pyridyl]-2-pyrimidine-amine,
    N-(3-chloro-phenyl)-4-[2-(2-hydroxy-propyl-amino)-4-pyridyl]-2-pyrimidine-amine,
    N-(3-chloro-phenyl)-4-[2-(2-imidazol-1-yl-ethyl-amino)-4-pyridyl]-2-pyrimidine-amine,
    N-(3-chloro-phenyl)-4-(2-hydrazino-4-pyridyl)-2-pyrimidine-amine,
    N-(3-chloro-phenyl)-4-[2-(2-amino-ethyl-amino)-4-pyridyl]-2-pyrimidine-amine,
    N-(3-chloro-phenyl)-4-[2-(2-hydroxy-ethyl-amino)-4-pyridyl]-2-pyrimidine-amine,
    N-(3-chloro-phenyl)-4-[2-(1-piperazinyl)-4-pyridyl]-2-pyrimidine-amine,
    N-(3-chloro-phenyl)-4-[2-{2-(4-morpholinyl)-ethyl-amino}-4-pyridyl]-2-pyrimidine-amine,
    N-(3-chloro-phenyl)-4-[2-(4-morpholinyl)-4-pyridyl]-2-pyrimidine-amine,
    N-(3-chloro-phenyl)-4-(2-n-propylamino-4-pyridyl)-2-pyrimidine-amine,
    N-(3-chloro-phenyl)-4-(2-amino-4-pyridyl)-2-pyrimidine-amine, and
    N-(3-chloro-phenyl)-4-(2-dimethylamino-4-pyridyl)-2-pyrimidine-amine, or a salt thereof.


The compounds useful according to the invention are prepared according to methods that are, per se, known in the art (this does mean, however, that, where novel compounds are produced, the respective process of manufacture is also novel) especially by reacting a compound of the formula (II),




    (or a salt thereof) wherein X is a leaving group, especially halo, for example fluoro, chloro, bromo or iodo, and the other moieties have the meanings given for a compound of the formula I1, with a hydrazino, amino or imino compound of the formula (III)

H—R6  (III)

    (or a salt thereof) wherein R6 has the meanings given for a compound of the formula I under a) where hydrazino is unsubstituted or mono to threefold substituted by optionally substituted alkyl, b), c) where piperazinyl is bound via a nitrogen atom, d) where morpholinyl is morpholino, or especially e),
    or by reacting a compound of the formula (IV)






    wherein n and R1 to R5 have the meanings given for a compound of the formula I and wherein R6* is hydrogen or optionally substituted alkyl as defined above, with a halogenide (Va) or an anhydride (Vb)

Hal-R9  (Va)

O(R9)2  (Vb)

    wherein Hal is chloro, bromo or iodo, especially chloro or bromo and R9 has the meanings of the carboxyl, sulfoxyl and sulfonyl moieties for a compound of the formula I under R6=f), g), h) or i);
    or by reacting a compound of the formula IV with an acetal of an amide (Vc), or any other form of an activated amide

(R10)2N—C(R7)—(OR11)2  (Vc)

    wherein the term (R10)2N is R8 as defined under formula I and R11 is alkyl or C(OR11)2 has the meaning of a cyclic acetal, such as dioxolanyl or dioxanyl for a compound of the formula I under R6=g), wherein R7 is hydrogen or alkyl,
    or by reacting a compound of the formula IV with a S-alkyl thiourea derivative (Vd), or any other form of an activated urea

R10N═C(R7)—SR11  (Vd)

    wherein the term R10N is R8 and R11 is alkyl for a compound of the formula I under R6=g), wherein R7 is amino, mono- or dialkylamino,
    or by reacting a compound of the formula IV with an aldehyde analogue of an unsubstituted or substituted lower alkyl compound that carries an aldehyde (—CHO) instead of the binding methylene group (—CH2—) of the corresponding unsubstituted or substituted lower alkyl as described above as substituent R6 “unsubstituted or substituted mono- or di-(lower alkyl)amino” wherein the substituents are as defined above in a final product of formula I in the presence of a reducing agent, preferably sodium cyanoborohydride for a compound of the formula I, wherein R6 is mono- or di-(lower alkyl)amino wherein the lower alkyl moieties are unsubstituted or substituted by one or more substituents independently selected from the group consisting of amino, N-mono- or N,N-di-(lower alkyl)-amino, (lower alkoxy)-lower alk-oxy, lower alkoxycarbonylamino, hydroxy-lower alkoxycarbonylamino, lower alkoxy-lower alkoxycarbonylamino, morpholinyl, hydroxy-lower alkylamino, cyano, halogen, oxo bound to a carbon that is not directly bound to a heteroatom, hydroximino, alkoximino, optionally substituted hydrazono, lower alkenyl, lower alkynyl, guanidyl, lower alkanoylamino, hydroxy-lower alkanoylamino, lower alkoxy-lower alkanoylamino, halo-lower alkanoylamino, lower alkylaminocarbonylamino, hydroxy-lower alkylaminocarbonylamino, lower alkoxy-lower alkylaminocarbonylamino, amidino, di-lower-alkylamino-cyclohexyl, carboxy, lower alkoxycarbonyl, hydroxy-lower alkoxycarbonyl, lower alkoxy-lower alkoxycarbonyl, lower alkylcarbonyldioxy (=lower alkoxycarbonyloxy), hydroxy-lower alkoxycarbonyloxy, lower alkoxy-lower alkoxycarbonyloxy, lower alkanoyloxy, halo-lower alkanoyloxy, hydroxy-lower alkanoyloxy, lower alkoxy-lower alkanoyloxy, carbamoyl, N-mono- or N,N-di-lower alkylcarbamoyl, N-(hydroxy-lower alkyl)carbamoyl, N-lower alkyl-N-hydroxy-lower alkylcarbamoyl, N,N-di-(hydroxy-lower alkyl)-carbamoyl, N-hydroxy-carbamoyl, hydroxy, lower alkoxy, lower alkenyloxy, lower alkinyloxy, lower haloalkoxy, lower alkylthio, lower alkylsulfinyl, lower alkylsulfonyl, lower alkoxysilyl, 4-tetrahydro-4H-pyranyl, 3-pyrrolidinyl, 2- or 3-tetrahydrofuryl, 2- or 3-dihydrofuryl, piperazinyl, lower alkanoyl-piperazinyl (including formylpiperazinyl), optionally substituted heteroaryl and optionally substituted heteroaryloxy;
    or (to obtain substituted hydrazino R6 in accordance with the definition under a) for a compound of formula I) by reacting a compound of the formula (VI)






    wherein n and R1 to R5 have the meanings given for a compound of the formula I, with a halogenide (Va) or an anhydride (Vb)

Hal-R9  (Va)

O(R7)9  (Vb)

    wherein Hal is chloro, bromo or iodo, especially chloro or bromo and R9 has the meanings of
    the acyl moiety for a compound of the formula I under R6=a),
    or (to obtain substituted hydrazino R6 in accordance with the definition under a) for a compound of formula I) by reacting a comound of the formula (VII a–d)






    wherein n and R1 to R5 have the meanings given for a compound of the formula I and R9 has the meanings of the acyl moiety for a compound of the formula I under R6=a), with a halogenide of the formula (VIII)

Hal-R12  VIII

    wherein Hal is chloro, bromo or iodo, especially chloro or bromo and R12 has the meanings of the alkyl moiety for a compound of the formula I under R6=a),
    and, if desired, a compound of the formula I thus obtained is converted into a salt thereof, or an obtained salt is converted into a free compound and/or into a different salt, or a compound of formula I is converted into a different compound of formula I,
    where functional groups in a starting material of the formula II and/or III, where necessary, are present in protected form, and any protecting groups present are removed in order to obtain the final product.


The compounds of the formula I thus obtainable and the remaining compounds of the formula I can, mutatis mutandis, also be prepared in accordance with manufacturing processes described in WO 95/09853, or in analogy to the methods described therein—therefor WO 95/09853 is herewith incorporated by reference. Also appropriate protecting groups, their introduction and removal are described in WO 95/09853. The characteristic of protecting groups in the strict sense is that they are not present in the final compounds of formula I.
A compound of the formula II can be obtained preferably by reacting a compound of the formula (IX)




(or—if n is 0—a salt thereof) wherein L is a leaving group, especially alkoxy, such as lower alkoxy, esterified OH (especially tosyloxy), or di-(lower alkylamino), X is a leaving group (preferably halo, such as chloro, bromo or iodo) and the other moieties are defined as for a compound of the formula I, with a guanidino compound of the formula (XI),





(or a salt thereof) wherein R1 is as defined for a compound of the formula I.

The reaction preferably takes place under conditions analogous to those mentioned in PCT application WO 95/09583, that is, in a suitable solvent or dispersing agent, for example a suitable alcohol, such as isopropanpol, or 2-butanol, at a temperature from room temperature (approximately 20° C.) to 150° C., e.g. under reflux.
The compound of the formula (IX) are known or can be obtained in accordance with methods that are known in the art, e.g. by reacting a compound of the formula (XII),




wherein the moieties R2, R3, R3 and R5 have the meanings given for a compound of the formula I and wherein X is a leaving group, preferably as defined for a compound of the formula (IX), either (i) under Claisen or analogue condensation reaction conditions (leading to a free hydroxy instead of the leaving group L in a compound of the formula IV; this free hydroxy group can then be converted into a leaving group, for example by ether formation with an alkylalkohol (“Alkoxy-H”;), yielding alkoxy as L, such as lower alkoxy, or by reaction with an acid or an active ester derivative, e.g. an acid chloride, yielding esterified OH (especially tosyloxy); or to alkoxy L, depending on the reaction conditions), or (ii) preferably by reaction with an N,N-di-(lower alkyl)-formamide di-lower alkylacetal, especially N,N-di-(methyl)formamide di-methylacetal, analogous to the procedure described in European Patent Application EP 0 233 461, which is incorporated by reference, e.g. by reaction in the respective N,N-di-(lower alkyl)-formamide di-lower alkylacetal at a temperature between room temperature and the boiling point of the reaction mixture, especially under reflux conditions.

An intermediate of the formula (XII) can, for example, be obtained by reaction of a metallated alkyl derivative of the formula (XIII),

R2—CH2-Metal  (XIII)

wherein R2 is as defined for a compound of the formula I (preferably it is hydrogen or alkyl) and Metal stands preferably for Mg—Hal (Hal=halogen) or Li, with a pyridine acid derivative of the formula (XIV),





wherein R3 to R5 have the meanings given for a compound of the formula I, X is a leaving group, preferably as defined for a compound of the formula (II), and Y is a leaving group, preferably N-lower alkyl-N-lower alkoxy-amino or halogen, under standard conditions for alkylation reactions.

Alternatively, an intermediate of the formula (XII), wherein n is 0, can be obtained by reaction of a metallated pyridine derivative of the formula (XV),




wherein R3 to R5 have the meanings given for a compound of the formula I, X is a leaving group, preferably as defined for a compound of the formula (IX), and Metal stands for Mg—Hal (Hal=halogen) or Li, under standard conditions for alkylation reactions with an acyl equivalent of the formula (XVI),




wherein R2 is as defined for a compound of formula I and Z is halo, or forms with the rest of the molecule an amide, an alkoxyamide, an anhydride or the like; or Z is hydrogen (meaning that the compound (XVI) is an aldehyde), resulting after the reaction in an alcohol that is then oxidised with a selective oxidant, for example in the presence of oxalylchloride and dimethyl sulfoxide, to the ketone intermediate of the formula (XII).

A starting material of the formula III is known, can be prepared by methods known in the art or is commercially available.
A starting material of the formula (XI) can be prepared (preferably obtaining an acid addition salt) by reaction of an aniline derivative of the formula (XVII),




wherein R1 is as defined for a compound of formula I, with cyanamide (NC—NH2) in a suitable solvent, e.g. an alcohol, such as a lower alkanol, for example (i) in the presence of equimolar amounts of the salt-forming acid, for example nitric acid, or (ii) in the presence of a clear, for example 60%, excess of a mineral acid, such as hydrochloric acid, where an ammonium salt of the desired salt-forming acid is added when the reaction is complete; at a temperature between room temperature and 150° C., e.g. under reflux.

Compounds of the formulae XIII, XIV, XV and XVI can be prepared according to methods that are known in the art.
The synthesis of many of the starting materials and intermediates can also be done as described in or in analogy to the processes described in WO 95/09853.
In all intermediates, functional groups that shall not participate in the reaction can be protected and deprotected at appropriate stages in order to avoid side reactions—appropriate protecting groups, their introduction and removal can be found e.g. in WO 95/09853.
The present invention also relates to novel starting materials and/or intermediates and to processes for the preparation thereof. The starting materials used and the reaction conditions chosen are preferably such that the compounds shown in this disclosure as being especially preferred or to be used preferably are obtained. Especially preferred among the process conditions are those described in the examples below, or analogous procedures.
The invention also relates to compositions which comprise the compounds of the formula I, or a salt thereof, as an active component, in particular plant-protecting compositions, and also to their use in the agricultural sector or related areas.
Active compounds of the formula I are customarily used in the form of compositions and may be added, simultaneously or successively, to the surface or plant to be treated together with additional active compounds. These additional active compounds may be either fertilizers, trace element-supplying agents or other preparations which influence plant growth. It is also possible, in this context, to use selective herbicides, such as insecticides, fungicides, bactericides, nematicides or molluscicides, or mixtures of several of these preparations, additionally, where appropriate, together with excipients, surfactants or other administration-promoting additives which are customary in formulation technology (designated collectively as carrier materials herein).
Suitable excipients and additives may be solid or liquid and are those substances which are appropriate in formulation technology, for example natural or regenerated minerals, solvents, dispersants, wetting agents, adhesives, thickening agents, binding agents or fertilizers.
A preferred method for applying a compound of formula I, or an agrochemical composition which comprises at least one of these compounds, is administration to the leaves (foliar application). The frequency and rate of aministration depend upon the risk of infestation by the corresponding pathogen. The compounds of formula II can, however, also penetrate the plant through the roots via the soil (systemic action). If the locus of the plant is impregnated with a liquid formulation or if the substances are introduced in solid form into the soil, e.g. in the form of granules (soil application). In paddy rice crops, such granules can be applied in metered amounts to the flooded rice fields. In order to treat seeds, the compounds of formula I can, however, also be applied to the seeds (coating), either by impregnating the grains or tubers with a liquid formulation of the active ingredient, or by coating them with a solid formulation.
Advantageous rates of application are in normally from 5 g to 2 kg of active ingredient (a.i.) per hectare (ha), preferably from 10 g to 1 kg of a.i./ha, especially from 20 g to 600 g a.i./ha. When the compound are used as seed dressings, dosages of from 10 mg to 1 g of active ingredient per kg seed are advantageous employed. The agrochemical compositions generally comprise 0.1 to 99% by weight, preferably 0.1 to 95% by weight, of a compound of formula I, 99.9 to 1% by weight, preferably 99.8 to 5% by weight, of a solid or liquid adjuvant and 0 to 25% by weight, preferably 0.1 to 25% by weight, of a surfactant. Whereas commercial products will preferably be formulated as concentrates, the end user will normally employ dilute formulations.
The compositions may also comprise further auxiliaries, such as stabilizers, antifoams, viscosity regulators, binders or tackifiers, as well as fertilizers or other active ingredients for obtaining special effects.


EXAMPLES
The subsequent examples are intended to illustrate the invention, without affecting the scope thereof.
Preparative Examples
Synthesis Example 1
(3-Chloro-phenyl)-{4-[2-(2-methoxy-1-methyl-ethylamino)-pyridin-4-yl]-pyrimidin-2-yl}-amine
A mixture of (3-chloro-phenyl)-[4-(2-chloro-pyridin-4-yl)-pyrimidin-2-yl]-amine (10.0 g, 0.03 mol) and 2-amino-1-methoxypropane (14.0 g, 0.16 mol) in dioxane (75 ml) is heated in an autoclave at 195° C. for 12 hours. The reaction mixture is partitioned between ethyl acetate and water. The organic phase is separated, dried over magnesium sulfate, filtered and evaporated under reduced presssure. The residue is purified by silicagel chromatography to give the title compound, m.p. 143–144° C.
Synthesis Example 2
(3-Chloro-phenyl)-[4-(2-hydrazino-pyridin-4-yl)-pyrimidin-2-yl]-amine
A mixture of (3-chloro-phenyl)-[4-(2-chloro-pyridin-4-yl)-pyrimidin-2-yl]-amine (4.8 g, 0.015 mol) in hydrazine (20 ml, 0.41 mol) is refluxed for 90 minutes. The reaction is poured into ethanol (300 ml) with efficient stirring. The resulting precipitate is filtered with suction to yield the title compound, m.p. 201–203° C.
Synthesis Example 3
{4-[2-(1-Acetoxybutyl-2-amino)-pyridin-4-yl]-pyrimidin-2-yl}-(3-chloro-phenyl)-amine
Step 1:
A mixture of (3-chloro-phenyl)-[4-(2-chloro-pyridin-4-yl)-pyrimidin-2-yl]-amine (10.0 g, 0.03 mol) and 2-amino-1-hydroxybutane (30.0 g, 0.3 mol) is heated at 180° C. for 18 hours. The reaction mixture is partitioned between ethyl acetate and water. The organic phase is separated, dried over magnesium sulfate, filtered and evaporated under reduced presssure. The residue is purified by silicagel chromatography to give the title compound, m.p. 99–101° C.
Step 2:
{4-[2-(1-Hydroxybutyl-2-amino)-pyridin-4-yl]-pyrimidin-2-yl}-(3-chloro-phenyl)-amine (1.24 g, 3.3 mmol) and acetic anhydride (0.41 g, 4.0 mmol) are refluxed in dimethoxyethane (20 ml) in the presence of a catalytic amount of DMAP for 30 minutes. The reaction mixture is evaporated under reduced pressure. The residue is crystallized by adding crushed ice. The solid is filtered and dried to give the title compound, m.p. 125–126° C.
Synthesis Example 4
{4-[3-Chloro-2-(2-methoxy-ethylamino)-pyridin-4-yl]-pyrimidin-2-yl}-(3-chloro-phenyl)-amine
Step 1:
A solution of 2,3-dichloropyridine (7.4 g, 0.05 mol) in THF (15 ml) is added at −60° C. to a solution of lithium diisopropylamine (0.07 mmol) in THF/hexane (1:1, 100 ml). After stirring for one hour at the same temperature a cooled solution of acetaldehyde in THF (8 ml) is added dropwise. The reaction mixture is allowed to warm to −20° C. and is then quenched with an aqueous saturated solution of ammonium chloride. The organic phase is separated, dried over magnesium sulfate, filtered and evaporated under reduced pressure to give a clear oil, that is used in the next step without further purification.
Step 2 (Swern Oxidation):
The product described under step 1 is added carefully at −60° C. to a solution prepared from oxalyl chloride (6.0 ml, 0.07 mol) and dimethylsulfoxide (8.5 ml, 0.12 mol) in methylene chloride (150 ml) at the same temperature. After stirring the reaction mixture for 30 minutes at −60° C. triethylamine (49 ml, 0.35 mol) is added and then allowed to reach room temperature. Brine is added and the methylene chloride is evaporated under reduced pressure. The product is extracted with ether, dried over magnesium sulfate, filtered and distilled under reduced pressure to give the product as a colorless oil, b.p. 90–93/2 mm.
Step 3:
The product described under step 2 is refluxed in dimethylformamide diethylacetal (15 ml) for 15 minutes. The still hot reaction mixture is diluted with hexane and the resulting crystalline product filtered. This intermediate is refluxed with 3-chlorophenylguanidine hydrogencarbonate (11.5 g, 0.05 mol) in 2-butanol (200 ml) for 14 hours. Diluting the reaction mixture with hexane and filtering gives the intermediate in form of yellow crystals.
Step 4:
The product prepared in step 3 (1.0 g, 2.8 mmol) is refluxed in 2-methoxyethylamine (5 ml) for 8 hours. The reaction mixture is partitioned between ethyl acetate and water. The organic phase is separated, dried, filtered and evaporated under reduced pressure to give the title compound, m.p. 172° C.
Synthesis Example 5
{4-[2-Chloro-6-(2-methoxy-1-methyl-ethylamino)-pyridin-4-yl]-pyrimidin-2-yl}-(3-chloro-phenyl)-amino
Step 1:
A suspension of 2,6-dichloroisonicotinic acid (20.0 g, 0.10 mol) and oxalylchloride (11.2 ml, 0.13 mol) in methylenechloride (100 ml) is stirred at room temperature in the presence of a katalytic amount of dimethylformamide for 2 hours to give a clear solution. The solvent is evaporated under reduced pressure and the residue is added to a well stirred solution of N,O-dimethylhydroxylamine (12.0 g, 0.2 mol) and triethylamine (10.2 g, 0.1 mol) at 0–5° C. After stirring for 2 hours at room temperature the reaction mixture is washed with water. The organic phase is dried over magnesium sulfate, filtered and evaporated under reduced pressure to give 2,6-dichloro-N-methoxy-N-methyl-isonicotinamide in form of colorless crystals, m.p. 69–70° C.
Step 2:
To a solution of 2,6-dichloro-N-methoxy-N-methyl-isonicotinamide (20 g, 0.085 mol) in THF (150 ml) is added at −30° C. a solution of methyl magnesium chloride in THF (0.2 mol) at such a rate that the temperature does not exceed −20° C. After stirring the mixture for an additional hour at −20° C. the mixture is poured on an aqueous, saturated solution of ammonium chloride. The organic phase is separated, dried over magnesium sulfate, filtered and evaporated to dryness.
Step 3:
The crystalline product obtained in step 2 is refluxed in dimethylformamide diethyl acetal (20 ml) for 10 minutes. The reaction mixture is evaporated under reduced pressure to give a dark red oil. The intermediate is refluxed with 3-chlorophenylguanidine hydrogencarbonate (16.2 g, 0.07 mol) in 2-butanol (250 ml) for 1 hour. The product is crystallizing during this time. The crystals are filtered and washed with ether: yellow crystals, m.p. 239–240° C.
Step 4:
The intermediate obtained in step 3 (0.5 g, 1.4 mmol) in 1-methoxy-2-aminopropane (2 ml) is refluxed for 16 hours. The crude product mixture is purified by flash column chromatography to give the crystalline title compound, m.p. 128–129° C.
Synthesis Example 6
[4-(2-Amino-pyridin-4-yl)-pyrimidin-2-yl]-(3-chloro-phenyl)-amine
A suspension of (3-chloro-phenyl)-[4-(2-chloro-pyridin-4-yl)-pyrimidin-2-yl]-amine (10.0 g, 0.03 mol) in dioxane (150 ml) and ammonia (20 g) is heated in an autoclave at 200° C. for 48 hours. The reaction mixture is partitioned between ethyl acetate and water. The organic phase is evaporated under reduced pressure and the product is purified by chromatography on silicagel.
Synthesis Example 7
N′-{4-[2-(3-Chloro-phenylamino)-pyrimidin-4-yl]-pyridin-2-yl}-.N.,.N.-dimethyl-formamidine
A mixture of [4-(2-amino-pyridin-4-yl)-pyrimidin-2-yl]-(3-chloro-phenyl)-amine (0.3 g, 1 mmol) and N,N-dimethylformamid diethylacetal (0.3 g, 2 mmol) are heated in dimethylformamide (5 ml) at 120° C. for 1 hour. The temperature is raised to 140° C. and the liberated ethanol is allowed to distill of. After cooling the reaction mixture to room temperature, diethylether is added and the resulting crystals are filtered with suction to give the title compound, m.p. 194–195° C.
Synthesis Example 8
N-{4-[2-(3-Chloro-phenylamino)-pyrimidin-4-yl]-pyridin-2-yl}-propionamide
Propionic acid anhydride (0.26 g, 2.0 mmol) is added to a solution of [4-(2-amino-pyridin-4-yl)-pyrimidin-2-yl]-(3-chloro-phenyl)-amine (0.5 g, 1.68 mmol) and a catalytic amount of DMAP in dimethoxyethane (10 ml) at 95° C. Heating is continued for 1 hour. On cooling the products starts to crystallize. Diethylether is added and the product is filtered of and washed with ether to give the title compound, m.p. 215–216° C.
Synthesis Example 9
{4-[2-(3-Chloro-phenylamino)-pyrimidin-4-yl]-pyridin-2-ylamino}-acetic acid
A mixture of (3-chloro-phenyl)-[4-(2-chloro-pyridin-4-yl)-pyrimidin-2-yl]-amine (10.0 g, 0.03 mol) and glycine (4.8 g, 0.06 ml) in DBU (100 ml) is heated at 150° C. under an atmosphere of argon for 40 hours. The still hot reaction mixture is poured into water. After washing the aqueous phase with ethyl acetate the pH is adjusted to 5 by adding citric acid. The resulting precipiate is filtered and recrystallized from dimethylformamide/ethanol to give the product in form of yellow crystals, m.p. 136–138° C. (with decomposition).
Synthesis Example 10
[4-(2-Allylamino-1-oxy-pyridin-4-yl)-pyrimidin-2-yl]-(3-chloro-phenyl)-amine
To a suspension of [4-(2-allylamino-pyridin-4-yl)-pyrimidin-2-yl]-(3-chloro-phenyl)-amine (1.0 g, 3 mmol) in methylene chloride (10 ml) is added a solution of m-chloroperbenzoic acid (0.73 g, 70%, 3 mmol) in methylen chloride (5 ml) at 5° C. The reaction mixture is stirred at room temperature for 30 minutes, washed with bicarbonate solution and evaporated under reduced pressure. The residue is purified by chromatography to give the title compound, m.p. 223–224° C.
Synthesis Example 11
(3-Chloro-phenyl)-{4-[2-(ethyl-methoxymethyl-amino)-pyridin-4-yl]-pyrimidin-2-yl}-amine
Solid potassium-t-butoxide (0.27 g, 2.5 mmol) is added at room temperature to a solution of (3-chloro-phenyl)-[4-(2-ethylamino-pyridin-4-yl)-pyrimidin-2-yl]-amine (0.5 g,1.5 mmol) in dry tetrahydrofurane (15 ml). The resulting solution is cooled to 0° C. and chloromethylmethylether (0.16 g, 2.0 mmol) is added at such a rate that the temperature does not exceed 5° C. After stirring the mixture for 2 hours at room temperature, the solvent is evaporated under reduced pressure and the product is purified by chromatography. The product is obtained in form of slightly yellow crystals, m.p. 114–115° C.
Analogously to the above examples the compounds of tables 1 to 58 and those of the following table 59 may be prepared.







TABLE 59













 






















Addition



CN
R1
R2
R3
R4
R5
R6
Salt
m.p.


















1.
Cl
H
H
H
H
NHCH2CH2NH2

151–156


2.
Cl
H
H
H
H
NH-(3-tetrahydrofuryl)

184–185


3.
Cl
H
H
H
H
NHCH2COOH

136–138


4.
Cl
H
H
H
H
NHCH(CH2CH3)CH2OCH3

Oil


5.
OCF2CHF2
H
H
H
H
NHCH(CH3)CH2OCH3

116–117


6.
Cl
H
H
H
Cl
NHCH2CH2OCH3

172


7.
Cl
H
F
H
H
NHCH(CH3)CH2OCH3

103–105


8.
Cl
H
H
H
H
NHCH2CH2CH2-(4-morpholinyl)

187–188


9.
Cl
H
H
Cl
F
NHCH(CH3)CH2OCH3

100–101


10.
Cl
CH3
Cl
H
H
NHCH(CH3)CH2OCH3

100–101


11.
Cl
H
Cl
H
H
NHCH(CH3)CH2OCH3

128–129


12.
Cl
H
H
H
H
NHCH(CH3)CH2OCH3
HCl
104–105 (d)


13.
Cl
H
H
H
H
NHCH(CH3)CH2OCH3
Citric
80–90 (d)









acid


14.
Cl
H
H
H
H
NHCH(CH3)CH2OCH3
PhSO3H
103–104 (d)


15.
Cl
H
H
H
H
NHCH(CH3)CH2OCH3
MeSO3H
111–112 (d)


16.
Cl
H
H
H
H
NHCH(CH3)CH2CH2-(1-imidazolyl)

150–151


17.
Cl
H
H
H
H
4-morpholinyl

175–176


18.
Cl
H
H
H
H
NH-(1-amino-2-cyclohexyl)

>215


19.
Cl
H
H
H
H
NHCH(CH3)CH2CH2N(CH3)2

147–148


20.
Cl
H
H
H
H
NHCH2CH2-(4-morpholinyl)

171–172


21.
Cl
H
H
H
H
1-piperazinyl

103–104


22.
Cl
H
H
H
H
NHNH2

201–203


23.
Cl
H
H
H
H
NHC(CH3)2CH2CH2OH

129–130


24.
Cl
H
H
H
H
NHC(CH3)2CH2CH2OCH3


25.
Cl
H
H
H
H
NHC(CH3)2CH2CH2OCH2CH3


26.
Cl
H
H
H
H
NHCH2CH2OCH2CH3

Oil


27.
Cl
H
H
H
H
NHCH(CH2CH2CH3)CH2OH

63–64


28.
Cl
H
H
H
H
NHC(CH3)2CH2OH

139–140


29.
Cl
H
H
H
H
NHCH2CH(CH3)OCH3


30.
Cl
H
H
H
H
NH CH2CH(CH3)CH2-(1-imidazolyl)

203–204


31.
Cl
H
H
H
H
NHCH(CH2CH3)CH2OH

90–91


32.
Cl
H
H
H
H
NHCH(CH3)CH2OCH3

143–144


33.
Cl
H
H
H
H
NHCH2CH2-(1-imidazolyl)


34.
Cl
H
H
H
H
NHCH2CH2OCH3

161–162


35.
Cl
H
H
H
H
NHCH(CH2OH)2

129–130


36.
Cl
H
H
H
H
NHCH2CH2CH(CH3)-(1-imidazolyl)

130


37.
Cl
H
H
H
H
NHCH2CH2OH

190–191


38.
Cl
H
H
H
H
N(CH2OCH3)CH(CH3)CH2OCH2OCH3)

oil


39.
Cl
H
H
H
H
NHCH(CH3)CH2OH

83–85


40.
Cl
H
H
H
H
NHC(CH3)2CH2OCH3

109


41.
Cl
H
H
H
H
NHCH(CH[CH3]CH2CH3)CH2OH

oil


42.
Cl
H
H
H
H
NHCH2CH2CH2NH2

140


43.
Cl
H
H
H
H
NHCH2CH2CH2-(1-imidazolyl)

176–177


44.
Cl
H
H
H
H
NHCH2CH2-(1,2,4)-triazol-1-yl


45.
Cl
H
H
H
H
NHCH2CH2CH2NHCOOCH2CH3

150–151


46.
Cl
H
H
H
H
NHCH2CH2CH2OH

135–142


47.
Cl
H
H
H
H
NHCH2CH2CH2OCH3


48.
Cl
H
H
H
H
NHCH2CH2CH2NH2
MeSO3H


49.
Cl
H
H
H
H
NHCH2CH2CH2-(1-imidazolyl)
MeSO3H


50.
Cl
H
H
H
H
NHCH(CH3)CH2Oac

137–138


51.
Cl
H
H
H
H
NHCH(CH2CH3)CH2OAc

125–126


52.
Cl
H
H
H
H
NHCH2CH2OAc

128–129


53.
Cl
H
H
H
H
NHCH(CH2CH2CH3)CH2OAc

oil


54.
Cl
H
H
H
H
NHCH(CH3)CH2OCH2CH3


55.
Cl
H
H
H
H
NHCH(CH3)CH(CH3)OCH3


56.
Cl
H
H
H
H
NHCH2CH(CH3)OCH3


57.
Cl
H
H
H
H
NHCH2CH2OCH2OCH3


58.
Cl
H
H
H
H
NH2

214–215


59.
Cl
H
H
H
H
N(CH3)2

178–179


60.
Cl
H
H
H
H
NHCH2CH3

201


61.
Cl
H
H
H
H
NHCOCH3

245–247


62.
Cl
H
H
H
H
NHCOCH2CH2CH2CH3

185–186


63.
Cl
H
H
H
H
NHCOCF3

180–181


64.
Cl
H
H
H
H
NHCH3

196–197


65.
Cl
H
H
H
H
NHCH(CH3)CH(OCH3)2

121–122


66.
Cl
H
H
H
H
N═C(CH3)N(CH3)2

Oil*


67.
Cl
H
H
H
H
NHCH2CH2CH2CH3

165–166


68.
Cl
H
H
H
H
NHCH(CH3)2

184–185


69.
Cl
H
H
H
H
NHCH2CH═CH2

179–180


70.
Cl
H
H
H
H
NHC(CH3)3

125–126


71.
Cl
H
H
H
H
NHCH(CH3)CH2CH2-(2-pyridyl)

136–137


72.
Cl
H
H
H
H
N(CH3)NH2

181–183


73.
Cl
H
H
H
H
NHCH2CH2SO2CH3

164–165


74.
Cl
H
H
H
H
NHCH2CH2SOCH3

167–168


75.
Cl
H
H
H
H
NHCH2-(2-tetrahydrofuryl)

151–152


76.
Cl
H
H
H
H
NHCH2CH(CH3)OH

152–153


77.
Cl
H
H
H
H
NHCOCH(OH)CH3

169–170


78.
Cl
H
H
H
H
NHCH2-(2-furyl)

185–186


79.
Cl
H
H
H
H
NHCH2-(2-pyridyl)

145–146


80.
Cl
H
H
H
H
NH-(3-pyrrolidyl)

129–130


81.
Cl
H
H
H
H
NHCH2CH═C(CH3)2

141–143


82.
Cl
H
H
H
H
NHCH(CH3)2
HCl
88–89


83.
Cl
H
H
H
H
NH-(4-tetrahydropyranyl)

166–167


84.
Cl
H
H
H
H
NHCH2-(3-tetrahydrofuryl)

184–185


85.
Cl
H
H
H
H
NHCH2CH(CH)3CH2CH3

162–164


86.
Cl
H
H
H
H
NHCH2CH2OCH2CH3

123–124


87.
Cl
H
H
H
H
NHCH2CH(OCH3)2

148–149


88.
Cl
H
H
H
H
NCH3NHCH3


89.
Cl
H
H
H
H
NHCH2CH2NHCOOCH2CH3

148–150


90.
Cl
H
H
H
H
NHCH2CH2-(2-pyridyl)

164–165


91.
Cl
H
H
H
H
N(CH3)CH2OCH3


92.
Cl
H
H
H
H
NHCOCF2CF2CF3

149–150


93.
Cl
H
H
H
H
NHCOCF2CF3

172–174


94.
Cl
H
H
H
H
NHCH2CH2CH2O-(2-pyrimidinyl)

93–95


95.
Cl
H
H
H
H
NHCH(CH3)CH2O-(2-pyrimidinyl)

79–80


96.
Cl
H
H
H
H
NHCOCH2CH3

215–216


97.
Cl
H
H
H
H
N═CHN(CH3)2

194–195


98.
Cl
H
H
H
H
N(CH2CH3)CH2OCH3

114–115


99.
Cl
H
H
H
H
NHCH(CH3)CH2CH3

198–199


100.
Cl
H
H
H
H
NHCH2CH2CH2Si(OCH3)3

144–146


101.
Cl
H
H
H
H
N(NH2) CH2CH2OH


102.
Cl
H
H
H
H
NHCH2-(3-pyridyl)

166–167


103.
Cl
H
H
H
H
NHCH2CF3

222–223


104.
Cl
H
H
H
H
N(CH3)N(Ac)2

197–199


105.
Cl
H
H
H
H
N(CH3)NHAc

210–212


106.
Cl
H
H
H
H
NHCH2CH2CH2OCOCH2CH3


107.
Cl
H
H
H
H
NHCH(CH3)CH2SCH3

149–150


108.
Cl
H
H
H
H
NHCH2CH2SCH3

148–149


109.
Cl
H
H
H
H
NHCH(CH3)CH2SOCH3


110.
Cl
H
H
H
H
N═C(CH3)N(CH2CH3)2


111.
Cl
H
H
H
H
N═C(CH3)N(CH3)CH2CH3


112.
Cl
H
H
H
H
N═C(CH3)N(CH2CH3)2


113.
Cl
H
H
H
H
NHS(O)N(CH3)2


114.
Cl
H
H
H
H
NHC(O)N(CH3)2


115.
Cl
H
H
H
H
NHCH(CH3)C═CHCH3


116.
Cl
H
H
H
H
NHCH(CH3)C═C(CH3)2


117.
Cl
H
H
H
H
NHCH2C≡CH


118.
Cl
H
H
H
H
NHCH(CH3)C≡CH


119.
Cl
H
H
H
H
NHCON(CH2CH3)2


120.
Cl
H
H
H
H
NHCOOCH3


121.
Cl
H
H
H
H
NHCOOCH2CH3

247–248


122.
Cl
H
H
H
H
N═C(NH2)NH2


123.
Cl
H
H
H
H
N═CHN(CH2CH3)2


124.
Cl
H
H
H
H
NHC(CH3)2CH2SCH3


125.
Cl
H
H
H
H
NH-(3-tetrahydrofuryl)
HCl
215–216


126.
Cl
H
H
H
H
NHCH2-(3-furyl)

174–177


127.
Cl
H
H
H
H
NHCH(CH3)2
MeSO3H


128.
Cl
H
H
H
H
NHCH(CH3)2
Cltric









acid


 


129.
Cl
H
H
H
H





138–139


 


130.
Cl
H
H
H
H
NHCH2CH(CH2CH3)CH2CH2CH2CH3

140–141


131.
Cl
H
H
H
H
NHCH2CH2-(4-imidazolyl)
Tartaric
solid









acid


132.
Cl
H
H
H
H
NHCH2CH2C(CH3)2OH

solid


133.
Cl
H
H
H
H
NHCH2CH2CO (1-[4-








ETHYLPIPERAZINYL])


 


134.
Cl
H
H
H
H





solid


 


135.
Cl
H
H
H
H





solid


 


136.
Cl
H
H
H
H
NHCH2CH2COOMe

solid


 


137.
Cl
H
H
H
H





solid


 


138.
Cl
H
H
H
H
NHCH2CH2CONHC(CH3)3

solid


139.
Cl
H
H
H
H
NHCH2CH2CONHCH2CH3

solid


140.
Cl
H
H
H
H
NHCH2CH2CONH(CH2CH3)2

solid


141.
Cl
H
H
H
H
NHCH2CH2COOCH(CH3)2

solid


 


142.
Cl
H
H
H
H





solid


 


143.
Cl
H
H
H
H





solid


 


144.
Cl
H
H
H
H





solid


 


145.
Cl
H
H
H
H
NHCH2CH2COOCH2CH3

solid


146.
Cl
H
H
H
H
NHCH2CH2CH2COOH

solid


147.
Cl
H
H
H
H
NHCH2CH2-(2-thienyl)

solid


148.
Cl
H
H
H
H
N(CH3)CH2CH2NH2

solid


149.
Cl
H
H
H
H
NHCH2CH2N(CH(CH3)2)2

solid


150.
Cl
H
H
H
H
NHCH2CH2CONHOCH3

solid


151.
Cl
H
H
H
H
NHCH2CH2CH2CH2NH2

solid


152.
Cl
H
H
H
H
NHCH2CH2SO3H

solid


153.
Cl
H
H
H
H
NHCH2CH2NHCH3
MeSO3H
solid


154.
Cl
H
H
H
H
NHCH2CH2NH2
MeSO3H
solid


 


155.
Cl
H
H
H
H





solid


 


156.
Cl
H
H
H
H
NHCH2CH2NHCH(CH3)2

solid


157.
Cl
H
H
H
H
NHCH2CH2NHCH2CH3
MeSO3H
solid


158.
Cl
H
H
H
H
NHCH2CH2CH2(4-triazolyl)
MeSO3H
solid


159.
Cl
H
H
H
H
NH-cyclohexyl

191–192


 


160.
Cl
H
H
H
H





240–241


 


161.
Cl
H
H
H
H
NHCH2CH2CH2NHCOCF3

solid


162.
Cl
H
H
H
H
NHCH2CH2CH2NH(2-pyrimidyl)

186–188


163.
Cl
H
H
H
H
NHCH2CH2CH2NHCOCH2CH3

171–172


164.
Cl
H
H
H
H
NHCH2CH3
MeSO3H
solid


165.
Cl
H
H
H
H
NHCH(CH3)CH2OCOOCH2CH3

102–103


166.
Cl
H
H
H
H
NHCH2CH2CH2(1-triazolyl)

149–150


 


167.
Cl
H
H
H
H





90–91


 


168.
Cl
H
H
H
H





139–140


 


169.
Cl
H
H
H
H
N(CH3)CH2OCH3


170.
Cl
H
H
H
H
NHCH2CH2CH3


 



Cl
H
H
H
H





214–215


 


171.
Cl
H
H
H
H





solid


 


172.
Cl
H
H
H
H





oil


 


173.
Cl
H
H
Cl
F
N(CH3)2

138–139


174.
Cl
H
H
H
Cl
N(CH3)2

165–167


175.
Cl
H
F
H
H
NHCH(CH3)2

174–175


 


176.
Cl
H
H
H
H





143–144


 


177.
Cl
H
H
H
H





178–179


 


178.
Cl
H
H
H
H





123–124


 


179.
Cl
H
H
H
H





119–120


 


180.
Cl
H
H
H
H
NH(CH2)5CO2CH3

112–115


181.
Cl
H
H
H
H
NHCH(CH3)CH2OCO2CH3

112–113


182.
Cl
H
H
H
H
NHNHCOCH3

205


183.
Cl
H
H
H
H
NHCH(CH3)CO2CH3

oil


184.
Cl
H
H
H
H
NHCH2CH2C(CH3)3

176–178


185.
Cl
H
H
H
H
NHCH2CH2CH(CH3)CH2C(CH3)3

155–156


186.
Cl
H
H
H
H
NHCH(CH3)CH2OCHO

119–121


187.
Cl
H
H
H
H
NHCOCH2OCH3

164


188.
Cl
H
H
H
H
NHSO2CH3

245


189.
Cl
H
H
H
H
NHCH(CH3)CO2CH(CH3)2

oil


190.
Cl
H
H
H
H
N[(CH2)3OCO2CH2CH3]CO2CH2CH3

solid


191.
Cl
H
H
H
H
CH2CH2COOH


192.
Cl
H
H
H
H
NHCH2CH2NHCH2CH3


193.
Cl
H
H
H
H
NHCH2CH2CH2-(1,2,4)-triazol-1 -yl


194.
Cl
H
H
H
H
NHCH2CO2CH3

164


195.
Cl
H
H
H
H
NHCH(CH3)CO2CH2CH3

oil


196.
Cl
H
H
H
H
NHCH2CH(CH3)CO2CH2CH3

oil


 


197.
Cl
H
H
H
H





155–161


 


198.
Cl
H
H
H
H





193–197


 


199.
Cl
H
H
H
H
NHCH2CH(CH3)CO2CH3

oil


200.
Cl
H
H
H
H
NHCH2CH2CH(OH)CH(OH)CH2OH

133–139


201.
Cl
H
H
H
H
NHCH(CH3)CO2CH2CH3

136–137


202.
Cl
H
H
H
H
NHCH2CONHCH3

191–192


203.
Cl
H
H
H
H
NHCH(CH3)CONHCH3

205


204.
Cl
H
H
H
H
NH(CH2)4OH


 


205.
Cl
H
H
H
H






 


206.
Cl
H
H
H
H
NH(CH2)3NHCH2CH2OH


207.
Cl
H
H
H
H
NHCH2CH2-(4-imidazolyl)


208.
Cl
H
H
H
H
NH(CH2)5OH


209.
Cl
H
H
H
H
N[(CH2)3OCONH2]CONH2


210.
Cl
H
H
H
H
N(CH3)CH2CH2OH


211.
Cl
H
H
H
H
N(CH2CH2OH)2


 


212.
Cl
H
H
H
H






 


213.
Cl
H
H
H
H
NH(CH2)3OCH(CH3)2


214.
Cl
H
H
H
H
NH(CH2)3N(CH3)2


215.
Cl
H
H
H
H
NH(CH2)3OCH2CH3


 


216.
Cl
H
H
H
H






 


217.
Cl
H
H
H
H
NHCH2-(4-pyridyl)


218.
Cl
H
H
H
H
NHCH2CH2-(1-piperidinyl)


219.
Cl
H
H
H
H
NH(CH2)3N(CH2CH3)2


220.
Cl
H
H
H
H
NH(CH2)2N(CH2CH3)2


221.
Cl
H
H
H
H
NH(CH2)2N(CH3)2


222.
Cl
H
H
H
H
NHCH2CH2-(1-pyrrolidinyl)


223.
Cl
H
H
H
H
NHCH2CH2CONH2


224.
Cl
H
H
H
H
NHCH2CH2CON(CH3)2


 


225.
Cl
H
H
H
H






 


226.
Cl
H
H
H
H
NHCH2CH2CONHCH2CH2CH3


227.
Cl
H
H
H
H
NHCH2CH2CONHCH2Ph


228.
Cl
H
H
H
H
NHCH2CH2CONH(c-Hexyl)


 


229.
Cl
H
H
H
H






 


230.
Cl
H
H
H
H
NHCH2CON(CH2CH3)2


 


231.
Cl
H
H
H
H






 


232.
Cl
H
H
H
H
NHCH2CH2CONHOH


233.
Cl
H
H
H
H
NHCH2CH2NHCH3


234.
Cl
H
H
H
H
NHCH2CH2CH2NHSO2CH3


235.
Cl
H
H
H
H
NHCH2CH2CH2NHCOCH3


236.
Cl
H
H
H
H
NHCH2CH2CH2NHCOOH(CH3)2


237.
Cl
H
H
H
H
NHCH2CH2CH2NHCONH2


238.
Cl
H
H
H
H
NHCH(CH3)CONHCH2CH3

173–174


 


239.
Cl
H
H
H
H





130


 


240.
Cl
H
H
H
H
NHCH(CH3)CH2OH

122–123


241.
Cl
H
H
H
H
N(COCF3)CH(CH3)CH2OCH3

oil


242.
Cl
H
H
H
H
N(CO2CH3)CH(CH3)CH2OCH3


243.
Cl
H
H
H
H
N(CHO)N(CH3)CO2C(CH3)3

solid


244.
Cl
H
H
H
H
NHN(CH3)COCH3

solid


245.
Cl
H
H
H
H
NHCH2CH2NHAc


246.
Cl
H
H
H
H
NHCH2CH2-(3-pyridyl)


247.
Cl
H
H
H
H
NH(CH2)3OH
MeSO3H


248.
Cl
H
H
H
H
NHCH2CH2COOH
Na


249.
Cl
H
H
H
H
NH(CH2)3NHCH2CH2OH
MeSO3H


250.
Cl
H
H
H
H
NHCH2CH2-(1-imidazolyl)
MeSO3H


251.
Cl
H
H
H
H
NHCH2CH2NHCH(CH3)2
MeSO3H


 


252.
Cl
H
H
H
H






 


253.
Cl
H
H
H
H






 


254.
Br
H
H
H
H
NH(CH2)3OH

144–146


255.
Br
H
H
H
H
NH(CH2)3OCH3 

132–134


256.
F
H
H
H
H
NH(CH2)3OH

153–156


257.
CH3
H
H
H
H
NH(CH2)3OH

128–130


258.
CF3
H
H
H
H
NH(CH2)3OH

155–156


259.
CH3O
H
H
H
H
NH(CH2)3OH

126–129


260.
CH3S
H
H
H
H
NH(CH2)3OH

 98–1 00


261.
NO2
H
H
H
H
NH(CH2)3OH

152–155


262.
Ac
H
H
H
H
NH(CH2)3OH

125–128


263.
CF3
H
H
H
H
NH(CH2)3OCH3

144–147


264.
ClCF2O
H
H
H
H
NHCH(CH3)CH2OCH3


265.
ClCF2O
H
H
H
H
NHCH2CH2OH

151–153


266.
OCF2CHF2
H
H
H
H
NH(CH2)3OH


267.
OCF2CHF2
H
H
H
H
NH(CH2)3OCH3


268.
CF3
H
H
H
H
NH(CH2)2NH2


269.
OCF2CHF2
H
H
H
H
NH(CH2)4NH2


270.
CO2H
H
H
H
H
NH(CH2)3OH


271
CO2CH3
H
H
H
H
NH(CH2)3OH


272
CF3
H
H
H
H
NHCH(CH3)CH2OH

142–143


273
AcNH
H
H
H
H
NHCH(CH3)CH2OAc

163


274
CH3
H
H
H
H
NHCH(CH3)CH2OH

80–81


275
CH3
H
H
H
H
NHCH2CH3


276
OCF2CHF2
H
H
H
H
NHCH2CH2OH


 


277
Cl
H
H
H
H





201–205


 


278
Cl
H
H
H
H
NHN(COCH3)2

210


 


279
Cl
H
H
H
H





166–167


 


280
Cl
H
H
H
H
NHCH2CH2CH2OCOOCH2CH3

148–150





(d) = under decomposition; CN = compound number






Biological Examples
Using the biological assays B-1 to B-12 described above, the tests are carried out employing compounds, or their salts, from Table 59 given above. Plus “+” in the following table means that the activity observed in the corresponding test system is 70% or more.

















TABLE 60





CN
B1
B2
B5
B6
B7
B8
B9
B10
B11
B12

























1







+




2
+






+

+


3





+

+

+


4



+

+
+

+
+


5







+
+
+


6


7


+
+



+


8



+

+


9


10


11


12
+

+
+
+
+
+
+

+


13
+

+
+
+
+

+

+


14



+
+
+

+

+


15
+


+
+
+

+

+


16





+

+

+


17


18


19





+


20



+

+

+

+


21


22







+


23


24


25


26




+
+

+

+


27




+
+

+

+


28


+

+
+

+

+


29


30


+


+

+

+


31
+
+
+

+
+

+
+


32
+

+
+
+
+
+
+

+


33


34




+
+

+
+
+


35


+

+
+

+


36







+


37


+
+
+
+
+
+

+


38


+




+

+


39
+



+
+
+
+

+


40


41


+

+


+


42





+

+

+


43




+
+
+
+

+


44


45


46
+





+
+

+


47


48





+

+

+


49




+
+

+

+


50


+
+
+
+
+
+

+


51







+

+


52







+

+


53





+


54


55


56


57


58
+

+
+
+
+
+
+

+


59



+



+

+


60
+

+

+
+

+

+


61








+


62







+

+


63


+

+
+
+
+

+


64

+



+

+

+


65


+
+
+
+
+
+

+


66


+

+
+
+
+
+
+


67


68
+




+

+
+
+


69


+

+
+

+

+


70





+

+

+


71







+

+


72


73


74









+


75
+

+

+
+

+

+


76







+

+


77


78





+


79





+

+


80


81



+

+

+

+


82
+




+

+

+


83





+

+
+
+


84





+

+

+


85


86


87







+

+


88


89


90





+

+


91







+

+


92


93




+
+

+


94
+




+

+


95


+




+

+


96


+




+

+


97





+

+

+


98







+


99


100





+


101


102





+

+


103



+



+

+


104


105


106





+

+

+


107


108


109


110


111


112


113


114


115


116


117


118


119


120


121






+
+


122


123


124


125





+
+
+

+

## Claims

1. A process for protecting a plant against attack or infestation by a phytopathogenic organism, comprising applying at least one compound of the formula I,




wherein
n is 0 or 1,
R1 is halogen, alkoxy, haloalkyl, haloalkoxy or alkyl,
R2 is hydrogen, halogen, alkyl, haloalkyl, alkoxy or haloalkoxy,
each of R3, R4 and R5 is, independently of the others, hydrogen, lower alkyl or halogen, and
R6 is
a) hydrazino, that is unsubstituted or one- to threefold substituted by optionally substituted alkyl and/or optionally substituted acyl,
b) cyclohexylamino, tetrahydro-4H-pyranyl-4-amino, pyrrolidine-3-amino, 2- or 3-tetrahydrofurylamino, all optionally substituted by amino, hydroxy, alkoxy, alkyl or alkoxyalkyl,
c) piperazinyl that is optionally substituted by amino, amino-lower alkyl, hydroxy, alkoxy, alkyl or alkoxyalkyl,
d) morpholinyl that is optionally substituted by amino, amino-lower alkyl, hydroxy, alkoxy, alkyl or alkoxyalkyl,
e) oxazolidinyl that is optionally substituted by amino, amino-lower alkyl, hydroxy, hydroxy-lower alkyl, alkoxy, alkyl or alkoxyalkyl,
f) thiazolidinyl that is optionally substituted by amino, amino-lower alkyl, hydroxy, hydroxy-lower alkyl, alkoxy, alkyl or alkoxyalkyl,
g) imidazolidinyl that is optionally substituted by amino, amino-lower alkyl, hydroxy, hydroxy-lower alkyl, alkoxy, alkyl or alkoxyalkyl,
h) amino or mono- or di-(lower alkyl)amino wherein the lower alkyl moieties are unsubstituted or substituted by one or more substituents independently selected from the group consisting of unsubstituted amino, N-mono- or N,N-di-(lower alkyl)-amino, (lower alkoxy)-lower alk-oxy, lower alkoxycarbonylamino, hydroxy-lower alkoxycarbonylamino, lower alkoxy-lower alkoxycarbonylamino, morpholinyl, hydroxy-lower alkylamino, cyano, halogen, oxo bound to a carbon that is not directly bound to a heteroatom, hydroximino, alkoximino, optionally substituted hydrazono, lower alkenyl, lower alkynyl, guanidyl, lower alkanoylamino, hydroxy-lower alkanoylamino, lower alkoxy-lower alkanoylamino, halo-lower alkanoylamino, lower alkylaminocarbonylamino, hydroxy-lower alkylaminocarbonylamino, lower alkoxy-lower alkylaminocarbonylamino, amidino, di-lower-alkylamino-cyclohexyl, carboxy, lower alkoxycarbonyl, hydroxy-lower alkoxycarbonyl, lower alkoxy-lower alkoxycarbonyl, lower alkylcarbonyldioxy (=lower alkoxycarbonyloxy), hydroxy-lower alkoxycarbonyloxy, lower alkoxy-lower alkoxycarbonyloxy, lower alkanoyloxy, halo-lower alkanoyloxy, hydroxy-lower alkanoyloxy, lower alkoxy-lower alkanoyloxy, carbamoyl, N-mono- or N,N-di-lower alkylcarbamoyl, N-(hydroxy-lower alkyl)carbamoyl, N-lower alkyl-N-hydroxy-lower alkyl-carbamoyl, N,N-di-(hydroxy-lower alkyl)-carbamoyl, N-hydroxy-carbamoyl, hydroxy, lower alkoxy, lower alkenyloxy, lower alkinyloxy, lower haloalkoxy, lower alkylthio, lower alkylsulfinyl, lower alkylsulfonyl, lower alkoxysilyl, 4-tetrahydro-4H-pyranyl, 3-pyrrolidinyl, 2- or 3-tetrahydrofuryl, 2- or 3-dihydrofuryl, piperazinyl, lower alkanoyl-piperazinyl, formylpiperazinyl, optionally substituted heteroaryl and optionally substituted heteroaryloxy,
i) optionally substituted alkanoylamino, optionally substituted alkenoylamino, optionally substituted alkynoylamino, optionally substituted mono- or di-alkylaminocarbonylamino, optionally substituted alkoxycarbonylamino, optionally substituted mono- or di-alkylamino sulfonylamino, optionally substituted mono- or di-alkylaminosulfoxylamino,
j) N-(optionally substituted alkyl)-N-(optionally substituted lower alkanoyl)-amino,
k) N-(optionally substituted alkyl)-N-(optionally substituted alkoxycarbonyl)-amino,
l) N-(optionally substituted alkyl)-N—(N′,N′-mono- or di-[optionally substituted alkyl]-aminocarbonyl)-amino, or
m) N═C(R7,R8) wherein R7 is hydrogen, alkyl, amino, mono- or di-alkylamino and R8 is amino, mono- or dialkylamino or wherein R7 and R8, together with the binding carbon atom, form a saturated five- to seven-membered ring with 0, 1 or 2 ring nitrogen atoms that is optionally substituted by one or more substituents;


or a salt thereof;
to one or more loci selected from the group consisting of a plant, a part of a plant, seeds and the site of a plant.

2. A process according to claim 1, wherein the phytopathogenic organism is a fungal organism.

3. A process according to claim 1, wherein the fungal organism is one or more selected from the group of classes consisting of Ascomycetes, Basidiomycetes, Oomycetes and Fungi imperfecti.

4. A process according to claim 1 wherein the phytopathogenic organism is a bacterium.

5. A process according to claim 1 wherein the phytopathogenic organism is a virus.

6. A process according to claim 1 wherein the phytopathogenic organism is a nematode.

7. A process according to claim 1 wherein a compound of formula I is applied wherein
n is 0 or 1,
R1 is halogen, haloalkyl or haloalkoxy,
R2 is hydrogen or alkyl,
each of R3, R4 and R5 is, independently of the others, hydrogen, lower alkyl or halogen, and
R6 is as defined in claim 1.

8. A process according claim 1 wherein a compound of formula I is applied wherein
n is 0 or 1,
R1 is halogen, haloalkyl or haloalkoxy,
R2 is hydrogen or alkyl,
each of R3, R4 and R5 is hydrogen, and
R6 is as defined in claim 1.

9. A process according to claim 1 wherein a compound of formula I is applied wherein
n is 0
R1 is chloro, trifluoromethyl, trifluoromethoxy or 1,1,2,2-tetrafluoroethoxy
R2, R3, R4 and R5 are hydrogen, and
R6 is
(a) hydrazino, that is unsubstituted or one- to threefold substituted by optionally substituted alkyl and/or optionally substituted acyl,
(e) amino or mono- or di-(lower alkyl)amino wherein the lower alkyl moieties are unsubstituted or substituted by one or more substitutents independently selected from the group con-sisting of unsubstituted amino, N-mono- or N,N-di-(lower alkyl)-amino, (lower alkoxy)-lower alk-oxy, lower alkoxycarbonylamino, hydroxy-lower alkoxycarbonylamino, lower alkoxy-lower alkoxycarbonylamino, morpholinyl, hydroxy-lower alkylamino, cyano, halogen, oxo bound to a carbon that is not directly bound to a heteroatom, hydroximino, alkoximino, optionally substituted hydrazono, lower alkenyl, lower alkynyl, guanidyl, lower alkanoylamino, hydroxy-lower alkanoylamino, lower alkoxy-lower alkanoylamino, halo-lower alkanoylamino, lower alkylaminocarbonylamino, hydroxy-lower alkylaminocarbonylamino, lower alkoxy-lower alkylaminocarbonylamino, amidino, di-lower-alkylamino-cyclohexyl, carboxy, lower alkoxycarbonyl, hydroxy-lower alkoxycarbonyl, lower alkoxy-lower alkoxycarbonyl, lower alkylcarbonyldioxy (=lower alkoxycarbonyloxy), hydroxy-lower alkoxycarbonyloxy, lower alkoxy-lower alkoxycarbonyloxy, lower alkanoyloxy, halo-lower alkanoyloxy, hydroxy-lower alkanoyloxy, lower alkoxy-lower alkanoyloxy, carbamoyl, N-mono- or N,N-di-lower alkylcarbamoyl, N-(hydroxy-lower alkyl)carbamoyl, N-lower alkyl-N-hydroxy-lower alkyl-carbamoyl, N,N-di-(hydroxy-lower alkyl)-carbamoyl, N-hydroxy-carbamoyl, hydroxy, lower alkoxy, lower alkenyloxy, lower alkinyloxy, lower haloalkoxy, lower alkylthio, lower alkylsulfinyl, lower alkylsulfonyl, lower alkoxysilyl, 4-tetrahydro-4H-pyranyl, 3-pyrrolidinyl, 2- or 3-tetrahydrofuryl, 2- or 3-dihydrofuryl, piperazinyl, lower alkanoyl-piperazinyl, formylpiperazinyl, optionally substituted heteroaryl and optionally substituted heteroaryloxy,
f) optionally substituted alkanoylamino, optionally substituted alkenoylamino, optionally substituted alkynoylamino, optionally substituted mono- or di-alkylaminocarbonylamino, optionally substituted alkoxycarbonylamino, optionally substituted mono- or di-alkylaminosulfonylamino, optionally substituted mono- or di-alkylaminosulfoxylamino,
g) N-(optionally substituted alkyl)-N-(optionally substituted lower alkanoyl)-amino,
h) N-(optionally substituted alkyl)-N-(optionally substituted alkoxycarbonyl)-amino,
i) N-(optionally substituted alkyl)-N—(N′,N′-mono- or di-[optionally substituted alkyl]-aminocarbonyl)-amino, or
j) N═C(R7, R8) wherein R7 is hydrogen, alkyl, amino, mono- or di-alkylamino and R8 is amino, mono- or dialkylamino or wherein R7 and R8, together with the binding carbon atom, form a saturated five- to seven-membered ring with 0, 1 or 2 ring nitrogen atoms that is optionally substituted by one or more substituents;


or a salt thereof.

10. A compound of the formula I,




wherein
n is 1,
R1 is halogen, alkoxy, haloalkyl, haloalkoxy or alkyl,
R2 is hydrogen, halogen, alkyl, haloalkyl, alkoxy or haloalkoxy,
each of R3, R4 and R5 is, independently of the others, hydrogen, lower alkyl or halogen, and
R6 is
a) hydrazino, that is unsubstituted or one- to threefold substituted by optionally substituted alkyl and/or optionally substituted acyl,
b) cyclohexylamino, tetrahydro-4H-pyranyl-4-amino, pyrrolidine-3-amino, 2- or 3-tetrahydrofurylamino, all optionally substituted by amino, hydroxy, alkoxy, alkyl or alkoxyalkyl,
c) piperazinyl that is optionally substituted by amino, amino-lower alkyl, hydroxy, alkoxy, alkyl or alkoxyalkyl,
d) morpholinyl that is optionally substituted by amino, amino-lower alkyl, hydroxy, alkoxy, alkyl or alkoxyalkyl,
e) oxazolidinyl that is optionally substituted by amino, amino-lower alkyl, hydroxy, hydroxy-lower alkyl, alkoxy, alkyl or alkoxyalkyl,
f) thiazolidinyl that is optionally substituted by amino, amino-lower alkyl, hydroxy, hydroxy-lower alkyl, alkoxy, alkyl or alkoxyalkyl,
g) imidazolidinyl that is optionally substituted by amino, amino-lower alkyl, hydroxy, hydroxy-lower alkyl, alkoxy, alkyl or alkoxyalkyl,
h) amino or mono- or di-(lower alkyl)amino wherein the lower alkyl moieties are unsubstituted or substituted by one or more substitutents independently selected from the group consisting of unsubstituted amino, N-mono- or N,N-di-(lower alkyl)-amino, (lower alkoxy)-lower alkoxy, lower alkoxycarbonylamino, hydroxy-lower alkoxycarbonylamino, lower alkoxy-lower alkoxycarbonylamino, morpholinyl, hydroxy-lower alkylamino, cyano, halogen, oxo bound to a carbon that is not directly bound to a heteroatom, hydroximino, alkoximino, optionally substituted hydrazono, lower alkenyl, lower alkynyl, guanidyl, lower alkanoylamino, hydroxy-lower alkanoylamino, lower alkoxy-lower alkanoylamino, halo-lower alkanoylamino, lower alkylaminocarbonylamino, hydroxy-lower alkylaminocarbonylamino, lower alkoxy-lower alkylaminocarbonylamino, amidino, di-lower-alkylamino-cyclohexyl, carboxy, lower alkoxycarbonyl, hydroxy-lower alkoxycarbonyl, lower alkoxy-lower alkoxycarbonyl, lower alkylcarbonyldioxy (=lower alkoxycarbonyloxy), hydroxy-lower alkoxycarbonyloxy, lower alkoxy-lower alkoxycarbonyloxy, lower alkanoyloxy, halo-lower alkanoyloxy, hydroxy-lower alkanoyloxy, lower alkoxy-lower alkanoyloxy, carbamoyl, N-mono- or N,N-di-lower alkylcarbamoyl, N-(hydroxy-lower alkyl)carbamoyl, N-lower alkyl-N-hydroxy-lower alkyl-carbamoyl, N,N-di-(hydroxy-lower alkyl)-carbamoyl, N-hydroxy-carbamoyl, hydroxy, lower alkoxy, lower alkenyloxy, lower alkinyloxy, lower haloalkoxy, lower alkylthio, lower alkylsulfinyl, lower alkylsulfonyl, lower alkoxysilyl, 4-tetrahydro-4H-pyranyl, 3-pyrrolidinyl, 2- or 3-tetrahydrofuryl, 2- or 3-dihydrofuryl, piperazinyl, lower alkanoyl-piperazinyl formylpiperazinyl, optionally substituted heteroaryl and optionally substituted heteroaryloxy,
i) optionally substituted alkanoylamino, optionally substituted alkenoylamino, optionally substituted alkynoylamino, optionally substituted mono- or di-alkylaminocarbonylamino, optionally substituted alkoxycarbonylamino, optionally substituted mono- or di-alkylaminosulfonylamino, optionally substituted mono- or di-alkylaminosulfoxylamino,
j) N-(optionally substituted alkyl)-N-(optionally substituted lower alkanoyl)-amino,
k) N-(optionally substituted alkyl)-N-(optionally substituted alkoxycarbonyl)-amino,
l) N-(optionally substituted alkyl)-N—(N′,N′-mono- or di-[optionally substituted alkyl]-aminocarbonyl)-amino, or
m) N═C(R7,R8) wherein R7 is hydrogen, alkyl, amino, mono- or di-alkylamino and R8 is amino, mono- or dialkylamino or wherein R7 and R8, together with the binding carbon atom, form a saturated five- to seven-membered ring with 0, 1 or 2 ring nitrogen atoms that is optionally substituted by one or more substituents;


or a salt thereof.