MXPA00008383A - N-sulphonyl and n-sulphinyl phenylglycinamide___________________ - Google Patents

N-sulphonyl and n-sulphinyl phenylglycinamide___________________

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Publication number
MXPA00008383A
MXPA00008383A MXPA/A/2000/008383A MXPA00008383A MXPA00008383A MX PA00008383 A MXPA00008383 A MX PA00008383A MX PA00008383 A MXPA00008383 A MX PA00008383A MX PA00008383 A MXPA00008383 A MX PA00008383A
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carbon atoms
phenyl
alkyl
tab
formula
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MXPA/A/2000/008383A
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Spanish (es)
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Zeller Martin
Jeanguenat Andre
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Syngenta Participations Ag
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Publication of MXPA00008383A publication Critical patent/MXPA00008383A/en

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Abstract

Novel&agr;-amino acid amides of formula (I) as well as possible isomers and mixtures of isomers thereof, wherein the substituents are defined as follows:n is the number zero or one;R1 is optionally substituted alkyl, alkenyl, alkynyl, cycloalkyl, cycloalkylalkyl, aryl or arylalkyl;or a group NRaRb wherein Ra and Rb are each independently of the other hydrogen, alkyl or form together an alkylene bridge;R2 is hydrogen or alkyl;R3 is optionally substituted aryl or heteroaryl;A is alkylene;and B is optionally substituted aryl;with the exception of the following compounds 2-phenyl-N- (1-phenyl-ethyl)- 2-(4-methylphenyl)- sulfonylamino-acetamide, 2-phenyl- N-(1-phenyl-ethyl)- 2-(4-chlorophenyl)- sulfonylamino-acetamide, 2-phenyl- N-(1-phenyl-ethyl)- 2-(4-nitrolphenyl)- sulfonylamino-acetamide, 2-phenyl- N-(1-phenyl-ethyl)- 2-(4-methoxyphenyl)- sulfonylamino-acetamide, 2-phenyl- N-(1-phenyl-ethyl)- 2-(4-fluorophenyl)- sulfonylamino-acetamide, 2-phenyl- N-(1-phenyl-ethyl)- 2-phenyl-sulfonylamino- acetamide and 2-phenyl-N-(1-phenyl-ethyl)-2-methane-sulfonylamino-acetamide. The novel compounds have plant-protective properties and are suitable for protecting plants against infestations by phytopathogenic microorganisms, in particular fungi.

Description

INTERNATIONAL APPLICATION PUBLISHED ACCORDING TO THE TREATY OF COOPERATION IN MATTERS OF PATENTS N-SULFONIL- AND N-SULFINIL-PHENYLGLYCINAMIDE The present invention relates to novel a-amino acid amides of the formula I below. It relates to the preparation of these substances, and to agrochemical compositions comprising at least one of these compounds as an active ingredient. The invention also relates to the preparation of these compositions, and to the use of the active ingredients or compositions in the control or prevention of infestation of plants by phytopathogenic microorganisms, especially fungi. The compounds according to the invention correspond to the general formula I: as well as the possible isomers and mixtures of isomers thereof, wherein the substituents are as defined below: n is the number 0 6 1; Ri is optionally substituted alkyl, alkenyl, alkynyl, cycloalkyl, cycloalkylalkyl, aryl or arylalkyl; or a group NRaRb, where Ra and Rb are each independently of the other, hydrogen, alkyl, or together form an alkylene bridge; R2 is hydrogen or alkyl; R3 is optionally substituted aryl or heteroaryl; A is alkylene; and B is optionally substituted aryl; with the exception of the following compounds: 2-phenyl-N- (1-phenyl-ethyl) -2- (4-methylphenyl) -sulfonylamino-acetamide, 2-phenyl-N- (1-phenyl-ethyl) -2- (4-chlorophenyl) -sulfonylamino-ace-amide, 2-phenyl-N- (1-phenyl-ethyl) -2- (-nitrophenyl) -sulfonylamino-acetamide, 2-phenyl-N- (1-phenyl-ethyl) - 2- (4-methoxyphenyl) -sulfonylamino-acetamide, 2-phenyl-N- (1-phenylethyl) -2- (4-fluorophenyl) -sulfonylamino-acetamide, 2-phenyl-N- (1-phenyl-ethyl) ) -2-phenyl-sulfonylamino-acetamide, and 2-phenyl-N- (1-phenyl-ethyl) -2-methansulfonlamino-acetamide.
The above alkyl, alkenyl, alkynyl, cycloalkyl, cycloalkylalkyl, aryl, arylalkyl or heteroaryl groups can carry one or more substituents identical or different. Normally no more than five substituents are present in each of these groups at the same time. Examples of the substituents of these groups are alkyl, alkenyl, alkyl, cycloalkyl, cycloalkylalkyl, phenyl and phenylalkyl, it being possible in turn that all the above groups bear one or more identical or different halogen atoms; alkoxy; alkenyloxy; alkynyloxy; alkyl alkox, haloalkoxy; thioalkyl, halothioalkyl, alkylsulfonyl; formyl, alkanoyl; hydroxyl; halogen, cyano; nitro; ammo; alkylamino; dialkylamino; carboxyl; alkoxycarbonyl; alkenyloxycarbonyl; alkynyloxycarbonyl. In formula I above, "halogen" includes fluorine, chlorine, bromine, and iodine, preferably fluorine, chlorine, or bromine. The alkyl, alkenyl, and alkynyl radicals may be straight or branched chain, this also applying to the alkyl, alkenyl, or alkynyl moiety of other alkyl, alkenyl, or alkynyl containing groups. Depending on the number of carbon atoms mentioned, alkyl by itself, or as part of another substituent, it should be understood, for example, as methyl, ethyl, propyl, butyl, pentyl, normal hexyl, normal heptyl, normal octyl, normal decyl, normal dodecyl and its isomers, such as isopropyl, isobutyl, tertiary butyl, secondary butyl, tertiary amyl, 1-et? l-hexyl, normal octyl, normal nonyl, or normal decyl. Cycloalkyl denotes, depending on the number of carbon atoms mentioned, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, or cyclooctyl. It will be understood that alkenyl means straight or branched chain alkenyl, such as allyl, vinyl, methallyl, 1-methylvinyl, but-2-en-1-yl, pent-2-en-1-yl, or hex-2-en -l-ilo.
Preferred alkenyl radicals contain from 3 to A carbon atoms in the chain. In the same way, alkynyl, according to the number of carbon atoms, can be straight or branched chain, and is usually propargyl, but-2-yl-l-yl, but-1-yn-3-yl, pent-2-yn-l-yl, or hex-2-yn-l-yl. The preferred meaning is propargyl. A haloalkyl group may have one or more halogen atoms (identical or different), such as, for example, CHC12, CH2F, CC13, CC1F2, CH2C1, CHF2, CF3, CH2CH2Br, CH2CF3, CH2CH2F, C2C15, CH2Br, CHBrCl, CH2CH2CF3 , etc. Alkoxy is usually methoxy, ethoxy, propyloxy, isopropyloxy, normal butyloxy, isobutyloxy, secondary butyloxy, and tertiary butyloxy. Methoxy and ethoxy are preferred. Thioalkyl is usually thiomethyl or thioethyl. Haloalkoxy is any alkoxy substituted with one or more halogen atoms. Typical examples are difluoromethoxy, trifluoromethoxy, 2,2-trifluoroethoxy, 1,1,2,2-tetrafluoroethoxy, 2-fluoroethoxy, 2-chloroethoxy, and 2,2-d? Fluoroethoxy? Lo. Aryl can be, for example, phenyl or naphthyl. Arylalkyl can be, for example, benzyl, 2-phenol-ethyl, or 3-phenol-propyl. Heteroappo means aromatic ring systems comprising mono-, bi-, or tri-cyclic systems, wherein at least one oxygen, nitrogen, or sulfur atom is present as a ring member. Examples are furyl, thienyl, pyrrolyl, imidazolyl, pyrazolyl, thiazolyl, isothiazolyl, oxazolyl, isoxazolyl, oxadiazolyl, thiadiazolyl, triazolyl, tetrazolyl, pyridyl, pyridazinyl, pyrimidyl, pyrazyl, triazinyl, tetrazinyl, indolyl, benzothiophenyl, benzofuranyl, benzimidazolyl, mdazolyl, benzotriazolyl, benzothiazolyl, benzoxazolyl, quinolinyl, isoquinolyl, phthalazinyl, quinoxalimyl, quinazolinyl, cinolmyl, and naphthipdinyl. Alkanoyl, according to the number of carbon atoms encompassed, is straight or branched chain. Typical examples are formyl, acetyl, propionyl, butyl, or pivaloyl. As a result of the presence of at least one asymmetric carbon atom, and / or at least one asymmetric sulfur atom, in the compounds of formula I, the compounds may be in the form of optical isomers. Due to the presence of a double bond -C = C- aliphatic, geometrical isomerism can also occur. Formula I is intended to cover all possible isomeric forms and mixtures thereof. Preference is given to the compounds of formula I wherein: n is the number zero or one; Ri is alkyl of 1 to 10 carbon atoms, alkenyl of 2 to 10 carbon atoms, alkynyl of 2 to 10 carbon atoms, cycloalkyl of 3 to 8 carbon atoms, cycloalkyl of 3 to 8 carbon atoms-alkyl of 1 to 6 carbon atoms, aryl of 6 to 10 carbon atoms, or aryl of 6 to 10 carbon atoms-alkyl of 1 to 6 carbon atoms which are optionally mono- or poly-substituted by alkyl of 1 to 8 carbon atoms carbon, alkoxy of 1 to 8 carbon atoms, thioalkyl of 1 to 8 carbon atoms, alkylsulfonyl of 1 to 8 carbon atoms, cycloalkyl of 3 to 8 carbon atoms, alkoxycarbonyl of 1 to 8 carbon atoms, alkenyloxycarbonyl of 3 to 8 carbon atoms, alkynyloxycarbonyl of 3 to 8 carbon atoms, cycloalkyl of 3 to 8 carbon atoms-alkyl of 1 to 6 carbon atoms, alkenyl of 2 to 8 carbon atoms, alkynyl of 2 to 8 carbon atoms , alkenyloxy of 3 to 8 carbon atoms, alkynyloxy of 3 to 8 carbon atoms, alkynyl anionic of 1 to 8 carbon atoms (wherein all these groups containing alkyl, alkenyl, alkynyl, or cycloalkyl, may be partially or completely halogenated), halogen, cyano, or nitro; or a group NRaRb, wherein Ra and b are each independently of the other, hydrogen, alkyl of 1 to 8 carbon atoms, or together they are alkylene of 2 to 7 carbon atoms; R2 is hydrogen or alkyl of 1 to 8 carbon atoms; R3 is phenyl, naphthyl, or heteroaryl formed by 1 or 2 5 or 6 membered rings containing from 1 to 4 identical or different heteroatoms cted from oxygen, nitrogen, or sulfur, and are optionally mono- or poly-substituted by alkyl of 1 to 8 carbon atoms, alkenyl of 2 to 8 carbon atoms, alkynyl of 2 to 8 carbon atoms, alkoxy of 1 to 8 carbon atoms, thioalkyl of 1 to 8 carbon atoms, alkylsulfonyl of 1 to 8 carbon atoms, cycloalkyl of 3 to 8 carbon atoms, cycloalkyl of 3 to 8 carbon atoms-alkyl of 1 to 6 carbon atoms, alkylenedioxy of 1 to 4 carbon atoms, alkoxycarbonyl of 1 to 8 carbon atoms, alkenyloxycarbonyl from 3 to 8 carbon atoms, alkynyloxycarbonyl of 3 to 8 carbon atoms, cycloalkyloxy of 3 to 8 carbon atoms, alkenyloxy of 3 to 8 carbon atoms, alkynyloxy of 3 to 8 carbon atoms, alkanoyl of 1 to 8 atoms of carbon, dialkylamino of 1 to 8 á carbon atoms, alkylamino of 1 to 8 carbon atoms (wherein all these groups containing alkyl, alkenyl, alkynyl, or cycloalkyl may be partially or completely halogenated), halogen, nitro, cyano, hydroxyl, or amino; A is alkylene of 1 to 8 carbon atoms; and B is optionally mono- or poly-substituted phenyl alkyl of 1 to 8 carbon atoms, alkenyl of 2 to 8 carbon atoms, alkynyl of 2 to 8 carbon atoms, alkoxy of 1 to 8 carbon atoms, thioalkyl of 1 to 8 carbon atoms, alkylsulfonyl of 1 to 8 carbon atoms, cycloalkyl of 3 to 8 carbon atoms, cycloalkyl of 3 to 8 carbon atoms-alkyl of 1 to 6 carbon atoms, alkoxycarbonyl of 1 to 8 carbon atoms, alkenyloxycarbonyl of 3 to 8 carbon atoms, alkynyloxy carbolyl of 3 to 8 carbon atoms, cycloalkyloxy of 3 to 8 carbon atoms, alkenyloxy of 3 to 8 carbon atoms, alkyloxy of 3 to 8 carbon atoms, alkanoyl of 1 to 8 carbon atoms, dialkylammon of 1 to 8 carbon atoms, alkylammon of 1 to 8 carbon atoms, aryloxyl of 6 to 10 carbon atoms, aryl of 6 to 10 carbon atoms-alkoxy of 1 to 6 carbon atoms, aryl of 6 to 10 carbon atoms-alchemloxyl from 1 to 6 carbon atoms, aryl of 6 to 10 carbon atoms-alkyloxyls from 1 to 6 carbon atoms, alkanoyloxy of 1 to 8 carbon atoms (wherein all these groups containing alkyl, alkenyl, alkynyl, or cycloalkyl, may be partially or completely halogenated, and wherein all the aryl containing groups may be optionally mono- or poly-substituted by alkyl of 1 to 8 carbon atoms, alkenyl of 2 to 8 carbon atoms, cycloalkyl of 3 to 8 carbon atoms, alkoxy of 1 to 8 carbon atoms, thioalkyl of 1 to 8 carbon atoms, alkoxycarbonyl of 1 to 8 carbon atoms, haloalkyl of 1 to 8 carbon atoms, haloalkoxy of 1 to 8 carbon atoms, halotioalkyl of 1 to 8 carbon atoms, halogen, nitro, or cyano), halogen, nitro, cyano, hydroxyl, amino, or the phenyl group may be substituted in two positions adjacent by alkylenedioxyl of 1 to 4 carbon atoms, wherein the alkylene part may be substituted by halogen (subgroup A). Within the scope of subgroup A, special mention must be made of those compounds of formula I wherein: n is a zero or one number; Ri is alkyl of 1 to 10 carbon atoms, alkenyl of 2 to 10 carbon atoms, cycloalkyl of 3 to 8 carbon atoms which are optionally mono- or poly-substituted by alkyl of 1 to 8 carbon atoms, alkoxy of 1 to 8 carbon atoms, thioalkyl of 1 to 8 carbon atoms, alkanoyl of 1 to 8 carbon atoms, alkoxycarbonyl of 1 to 8 carbon atoms, haloalkyl of 1 to 8 carbon atoms, haloalkoxy of 1 to 8 carbon atoms , halotioalkyl of 1 to 8 carbon atoms, halogen, nitro, or cyano; or a group NRaRb, wherein Ra and Rb are each independently of the other, hydrogen, alkyl of 1 to 8 carbon atoms, or are together tetramethylene or pentamethylene; R2 is hydrogen or methyl; R3 is phenyl, naphthyl, furyl, thienyl, imidazolyl, thiazolyl, oxazolyl, pyridyl, pyrimidinyl, benzothiophenyl, benzothiazolyl, quinolinyl, pyrazolyl, indolyl. benzimidazolyl, or pyrrolyl, optionally substituted by 1 to 3 substituents selected from alkyl of 1 to 8 carbon atoms, alkenyl of 2 to 8 carbon atoms, cycloalkyl of 3 to 8 carbon atoms, alkoxyl of 1 to 8 carbon atoms, carbon, thioalkyl of 1 to 8 carbon atoms, alkoxycarbonyl of 1 to 8 carbon atoms, haloalkyl of 1 to 8 carbon atoms, haloalkoxy of 1 to 8 carbon atoms, halotioalkyl of 1 to 8 carbon atoms, halogen, hydroxyl , nitro, or cyano; A is alkylene of 1 to 4 carbon atoms; and B is phenyl optionally substituted by 1 to 3 substituents selected from alkyl of 1 to 8 carbon atoms, alkoxy of 1 to 8 carbon atoms, alkenyloxy of 3 to 8 carbon atoms, alkynyloxy of 3 to 8 carbon atoms , phenylalkyloxy of 1 to 6 carbon atoms, phenylalkenyloxy of 3 to 6 carbon atoms, phenylalkynyloxy of 3 to 6 carbon atoms, thioalkyl of 1 to 8 carbon atoms, alkoxycarbonyl of 1 to 8 carbon atoms, haloalkoxy of 1 to 8 carbon atoms, haloalkenyloxy of 3 to 8 carbon atoms, halogen, hydroxyl, nitro, or cyano (wherein all phenyl-containing groups may be optionally substituted by 1 to 3 substituents selected from alkyl of 1 to 8 atoms carbon, alkoxy of 1 to 8 carbon atoms, thioalkyl of 1 to 8 carbon atoms, haloalkyl of 1 to 8 carbon atoms, haloalkoxy of 1 to 8 carbon atoms, halotioalkyl of 1 to 8 carbon atoms, halogen, or cyano) (subgroup B). An important group is formed by the compounds of the formula I wherein: n is the number one; Ri is alkyl of 1 to 6 carbon atoms, alkenyl of 2 to 10 carbon atoms, cycloalkyl of 5 to 6 carbon atoms, which are optionally mono- or poly-substituted by alkyl of 1 to 8 carbon atoms, alkoxy 1 to 8 carbon atoms, alkoxycarbonyl of 1 to 8 carbon atoms, haloalkyl of 1 to 8 carbon atoms, haloalkoxy of 1 to 8 carbon atoms, halogen, or cyano; or a group NRaRb, wherein Ra and Rb are each independently of the other, methyl or ethyl; R2 is hydrogen; R3 is phenyl optionally substituted by 1 to 3 substituents selected from alkyl of 1 to 8 carbon atoms, alkenyl of 2 to 8 carbon atoms, cycloalkyl of 3 to 8 carbon atoms, alkoxy of 1 to 8 carbon atoms, thioalkyl of 1 to 8 carbon atoms, alkoxycarbonyl of 1 to 8 carbon atoms, haloalkyl of 1 to 8 carbon atoms, haloalkoxy of 1 to 8 carbon atoms, halotioalkyl of 1 to 8 carbon atoms, halogen, hydroxyl, nitro , or cyano; A is ethylene; and B is phenyl optionally substituted by 2 to 3 substituents selected from alkyl of 1 to 8 atoms of carbon, alkoxy of 1 to 8 carbon atoms, alkenyloxy of 3 to 8 carbon atoms, alkynyloxy of 3 to 8 carbon atoms, phenylalkyloxy of 1 to 6 carbon atoms, phenylalkenyloxy of 3 to 6 carbon atoms, phenylalkynyloxy 3 to 6 carbon atoms, thioalkyl of 1 to 8 carbon atoms, alkoxycarbonyl of 1 to 8 carbon atoms, haloalkoxy of 1 to 8 carbon atoms, haloalkenyloxy of 3 to 8 carbon atoms, halogen, hydroxyl, nitro, or cyano (SQ where all phenyl-containing groups may be optionally substituted by 1 to 3 substituents selected from alkyl of 1 to 8 carbon atoms, alkoxy of 1 to 8 carbon atoms, thioalkyl of 1 to 8 carbon atoms, haloalkyl of 1 to 8 carbon atoms, haloalkoxy of 1 to 8 carbon atoms, halotioalkyl of 1 to 8 carbon atoms, halogen, or cyano) (subgroup C). A special group within the scope of subgroup C comprises compounds of formula I wherein: n is number one; Ri is alkyl of 1 to 4 carbon atoms optionally mono- or poly-substituted by fluorine, chlorine, bromine, or dimethylamine; R2 is hydrogen; R3 is phenyl optionally substituted by 1 to 3 substituents selected from alkyl of 1 to 8 carbon atoms, alkenyl of 2 to 8 carbon atoms, cycloalkyl of 3 to 8 carbon atoms, alkoxy of 1 to 8 carbol atoms. . thioalkyl of 1 to 8 carbon atoms, alkoxycarbonyl of 1 to 8 carbon atoms, haloalkyl of 1 to 8 carbon atoms, haloalkoxy of 1 to 8 carbon atoms, halotioalkyl of 1 to 8 carbon atoms, halogen, nitro, or cyano; A is ethylene; and B is a group: wherein: Rβ is alkyl of 1 to 4 carbon atoms, and Rg is alkyl of 1 to 8 carbon atoms, alkenyl of 3 to 8 carbon atoms, alkynyl of 3 to 8 carbon atoms, phenylalkyl of 1 to 6 atoms of carbon, phenylalkenyl of 3 to 6 carbon atoms, phenylalkynyl of 3 to 6 carbon atoms, haloalkyl of 1 to 8 carbon atoms, haloalkenyl of 3 to 8 carbon atoms (wherein all phenyl-containing groups may optionally be substituted by 1 to 3 substituents selected from alkyl of 1 to 8 carbon atoms, alkoxy of 1 to 8 carbon atoms, thioalkyl of 1 to 8 carbon atoms, haloalkyl of 1 to 8 carbon atoms, haloalkoxy of 1 to 8 carbon atoms, halotioalkyl of 1 to ~ carbon atoms, halogen, or cyc.o) (subgroup Ca). Have already been proposed c ---: i: s derivatives of a-amino acid which have a different structure class, for the control of fungi that destroy plants (for example, in Patent Numbers EP-398,072, EP-425925, DE-40, 26, 966, EP-477,639, EP-493,683, DE -40,35,851, EP-487,154, EP-496239, EP-550,788 and EP-554729). However, these compositions are not satisfactory in their action. Surprisingly, with the structure of the compound of formula I, new classes of microbicides having a high activity have been found.
Description of the process for the preparation of the compounds according to the invention The compounds of the formula I can be prepared by one of the following processes: a) - ° S-X * H, N-? J_COOH »-. R-S "NH-I * COOH P) p." PaS? A (0) n R, lll? V "Step B 3 | ++ H, N-A» -EB * O II 7 R.-S-NH- 'II < ° > n -H »P N.H-A-B Faso B: An amino acid of formula II, or a derivative activated by carboxyl ie an amino acid of the formula II, wherein Ri, n, R2, and R3 have the meaning defined above, is reacted with an amine of formula V, wherein A and B have the meaning defined above, optionally in the presence of a base, and optionally in the presence of a diluting agent. Any carboxyl-activated derivatives are suitable as carboxyl-activated derivatives of the amino acid of formula II, such as acid halides, for example acid chlorides or fluorides; symmetrical or mixed anhydrides, for example the mixed O-carboxylic acid anhydrides; activated esters, for example p-nitrophenyl esters or N-hydroxysuccinimide esters, and the activated forms of amino acid II produced in situ using condensation agents (for example, dicyclohexylcarbodiimide, carbonyldiimidazole, hexafluorophosphate 0- (benzotriaz-1) -il) -N, N, N ', N' -bis (pentamethylene) uronium, 0- (benzotriaz-1-yl) -N, N, N ', N'-bis (tetramethylene) uronium hexafluorophosphate, hexafluorophosphate (benzotriazol-1-yloxy) tripyrrolidinophosphonium, (benzotriazol-1-yloxy) -tris (dimethylamino) phosphonium hexafluorophosphate, or O- (benzotriazol-1-yl) -N, N, N ', N' -tetramethyluronium hexafluorophosphate) . The acid halides corresponding to the amino acid of the formula II can be prepared by reacting the amino acid of the formula II in a manner known per se with a halogenating agent, for example phosphorus pentachloride. thionyl chloride, oxalyl chloride, cyanuric fluoride, or diethylaminosulfur trifluoride. The mixed anhydrides corresponding to the amino acid of formula II can be prepared by reacting the amino acid of formula II with esters of chloroformic acid, for example alkyl esters of chloroformic acid, preferably isobutyl ester of chloroformic acid, in the absence or in the presence of an acid binding agent, such as an inorganic or organic base, for example a tertiary amine, for example triethylamine, pyridine, N-methylpiperidine, or N-methylmorpholine. Step: The compounds of the formula II can be prepared by the reaction of an amino acid of the formula IV, wherein R2 and R3 have the same meanings as defined above, with a sulfonyl halide or a sulfinyl halide of the formula III, where Ri and n have the meanings defined above, and wherein X is halide, preferably chlorine or bromine. The reaction is optionally carried out in a solvent and in the presence of a base. b) R -A-B VI Step C: The compounds of the formula I can also be prepared by the reaction of an amino acid derivative of the formula VI, wherein R2, R3, A, and B have the same meanings as defined above, with a sulfonyl halide or a sulfinyl halide of the formula III, wherein Ri and n have the same meanings as defined above, and wherein X is halide, preferably chlorine or bromine. The reaction is carried out in the same manner as described for step A. c) The compounds of the formula I, wherein n is 1, can be prepared by the oxidation of the compounds of the formula I wherein n = 0 (I1), with organic oxidizing agents, such as alkyl hydroperoxides, for example cumyl hydroperoxide, and inorganic oxidizing agents, such as peroxides, for example hydrogen peroxide, or transition metal oxides, for example chromium trioxide, and transition metal oxide salts, for example potassium permanganate, potassium or sodium, are suitable oxidizing agents. The reaction of the compounds of the formula I 'with the oxidizing agents takes place in an inert diluent, such as water or a ketone, for example acetone, or in mixtures thereof, in the absence or in the presence of an acid, or in the absence or in the presence of a base, at temperatures of -80 ° C to + 150 ° C.
The compounds of the formula VI can be prepared by the following process d): C RJ step E, or NH.- ^ H NH-A-B VI Step D: An isocyanide of formula VII, wherein A and B are as defined above (see D. Seebach, G. Adam, T. Gees, M. Schiess, W. eigang, Chem. Ber., 1988, 121 , 507), is reacted with a known compound of formula VIII (R2 and R3 are as defined above), a known compound of formula IX (Rio is lower alkyl or H), and ammonia in a solvent (usually a alcohol such as methanol or ethanol, tetrahydrofuran, methylene chloride), at a temperature between -20 ° C and + 150 ° C, optionally in the presence of a Lewis acid, usually ZnCl 2 (Ugi reaction).
Step E: A compound of formula X, where R2, R3, io, A, and B are as defined above, hydrolyzed under acidic or basic conditions at a temperature between 0 ° C and 100 ° C. Typical acids are mineral acids, such as HCl, H2S0, organic acids such as p-toluenesulfonic acid, methanesulfonic acid, tpfluoroacetic acid; Typical bases are NaOH, KOH, Ba (0H) 2, carbonates, tpetilamma, ethyl-di-isopropylamine; Typical solvents are alcohols such as ethanol or methanol, tetrahydrofuran, dimethylformamide, dimethyl sulfoxide. Compound VI can be converted to the compounds of formula I by step C as described in process b). The invention also relates to amino acid derivatives of formula VI, wherein R2, R3, A, and B have the meaning defined for formula I. The sulphonic acid or the sulfinic acid, or the sulphonic or sulfinic acid derivative of the formula III, required for process a) or b), and the amino acids of the formula IV, required for process a), are known per se same. Suitable sulphonic or sulfinic acid derivatives of formula III are any compounds wherein Z is a leaving group, such as sulphonic acid halides or sulfinic acid halides, for example sulfochlorides or sulfinic acid chlorides; symmetrical or mixed anhydrides; and the activated forms of the sulfonic acid or sulfinic acid produced m if you using condensation agents, such as dicyclohexylcarbodiimide or carbonyldiimidazole.
Surprisingly, it has now been found that the compounds of formula I, for practical purposes, have a very convenient biocidal spectrum in the control of phytopathogenic microorganisms, especially fungi. They have very convenient curative and preventive properties, and are used in the protection of numerous crop plants. With the compounds of the formula I, it is possible to inhibit or destroy pests that occur in different crops of useful plants, or in the parts of those plants (fruit, cocoon, leaves, stems, tubers, roots), while the parts of Plants that grow later, for example, also continue to be protected against phytopathogenic fungi. The novel compounds of the formula I are preferably effective against specific genera of the kinds of fungi: imperfect fungus (for example Cercospora), Basidiomycetes (for example Puccima), and Ascomycetes (for example Erysiphe and Ventupa), and especially against Oomycetes ( for example Plasmopara, Peronospora, Bremia, Pythium, Phytophthora). Accordingly, they represent, in the protection of the plants, a valuable addition to the compositions for controlling phytopathogenic fungi. The compounds of the formula I can also be used as coatings to protect seeds (fruit, tubers, grains) and plant cuttings, from fungal infections and against phytopathogenic fungi that occur in the soil.
The invention also relates to compositions comprising compounds of the formula I as active ingredients, especially plant protection compositions, and to their use in the agricultural sector or in related fields. In addition, the present invention includes the preparation of these compositions, wherein the active ingredient is homogenously mixed with one or more of the substances or groups of substances described herein. Also included is a method for the treatment of plants, which comprises applying the novel compounds of the formula I or the novel compositions. The target crops to be protected within the scope of this invention comprise, for example, the following plant species: cereals (wheat, barley, rye, oats, rice, corn, sorghum, triticale spelled, and related species); beet (sugar beet and fodder beet); grapefruit, hard fruit and soft fruit (apples, pears, plums, peaches, almonds, cherries, strawberries, raspberries, and blackberries); leguminous plants (beans, lentils, peas, and soybeans); oil plants (rapeseed, mustard, poppy, olives, sunflowers, coconut, castor oil plants, cocoa seeds, and peanuts); cucumber plants (courgettes, cucumbers, and melons); fiber plants (cotton, linen, hemp, and jute); citrus fruit (oranges, lemons, grapefruits, and tangerines); vegetables (spinach, lettuce, asparagus, cabbages, carrots, onions, tomatoes, potatoes, and paprika); lauraceae (avocados, cinnamon, and camphor), and plants such as tobacco, nuts, coffee, sugar cane, tea, pepper, vines, hops, bananas, and natural rubber plants, and also ornamentals. The compounds of formula I are usually applied in the form of compositions, and can be applied to the area or plant to be treated, simultaneously or in succession with other active ingredients. The additional active ingredients can be fertilizers, micronutrient donors, or other preparations that influence the growth of the plant. It is also possible to use selective herbicides, and insecticides, fungicides, bactericides, nematocides, molluscicides, or mixtures of several of these preparations, if desired together with other vehicles, surfactants, or other application-promoting auxiliaries customarily employed in the technology of the formulation. Suitable vehicles and auxiliaries can be solid or liquid, and correspond to substances ordinarily employed in the technology of the formulation, such as, for example, natural or regenerated mineral substances, solvents, dispersants, wetting agents, viscosifiers, thickeners, binding agents. , or fertilizers. These vehicles are described, for example, in International Publication Number WO 97/33890.
A preferred method for applying a compound of the formula I, or an agrochemical composition comprising at least one of these compounds, is the application to the foliage of the plants (foliar application), depending on the frequency and concentration of application of the risk of infestation. for the pathogen in question. The compounds of the formula I can also be applied to the propagation material (grains, fruits, tubers, shoots, roots, etc.) (coating), for example, by impregnating cereal grains (seeds) or tubers. potato, or freshly cut saplings, with a liquid formulation of the active ingredient, or by coating them with a solid formulation. The compounds of the formula I are used in an unmodified form, or preferably together with the auxiliaries conventionally employed in the technology of the formulation, and for that purpose, are conveniently formulated in a known manner, for example in emulsifiable concentrates, pastes Coatable, directly sprayable or dilutable solutions, diluted emulsions, wettable powders, soluble powders, dry powders, granules, and also encapsulations, for example, in polymeric substances. As with the nature of the compositions, the methods of application, such as spraying, atomizing, dusting, scattering, coating, or watering, are selected in accordance with the intended objectives and the prevailing circumstances.
Suitable concentrations of application are usually from 1 gram to 2 kilograms of active ingredient (i.a.) per hectare, preferably 10 grams to 1 kilogram of active ingredient per hectare, especially from 25 grams to 750 grams of active ingredient per hectare. . When used as seed coatings, concentrations of 0.001 gram to 1.0 gram of active ingredient per kilogram of seeds are conveniently used. The formulations, i.e., the compositions, preparations, or mixtures comprising the compound (active ingredient) of the formula I, and where appropriate, a solid or liquid auxiliary, are prepared in a known manner, for example by homogeneous mixing and / or milling of the active ingredient with extenders, for example solvents, solid carriers, and when appropriate, surface activity compounds (surfactants). The compounds of formula I can be mixed with other fungicides, resulting in some cases unexpected synergistic activities. Particularly preferred mixing components are azoles, such as azaconazole, bitertanol, bromuconazole, ciproconazole, diphenoconazole, diniconazole, epoxiconazole, fenbuconazole, fluquinconazole, flusilazole, flutriafol, hexaconazole, imazalil, imibenconazole, ipconazole, metconazole, myclobutanil, pefurazoate, penconazole. , pirifenox, prochloraz, propiconazole, tebuconazole, tetraconazole, triadimefon, triadimenol, triflumizole, or triticonazole; pyrimidinyl carbinols, such as ancimidol, fenarimol, or nuarimol; 2-amino-pyrimidine, such as bupirimate, dimethirimol, or etirimol; morpholines, such as dodemorf, fenpropidine, phenpropimorf, spiroxamine, or tridemorph; anilinopyrimidines, such as cyprodinil, mepanipyrim or pyrimethanil; pyrrole, such as fenpiclonil or fludioxonil; phenylamides, such as benalaxyl, furalaxyl, metalaxyl, R-metalaxyl, ofurace or oxadixyl; benzimidazoles, such as benomyl, carbendazim, debacarb, fuberidazole, or thiabendazole; dicarboximides, such as clozolinate, dichlozoline, iprodione, myclozoline, procymidone, or vinclozoline; carboxamides, such as carboxin, fenfuran, flutolanil, mepronil, oxycarboxin, or tifluzamide; guanidines, such as guazatine, dodine, or iminoctadine; strobilurins, such as azoxyestrobin, cresoxima-methyl, methominoestrobin, SSF-129, 2- [(2-trifluoromethyl) -pyrid-6-yloxymethyl 3-methoxyacrylate], or 2-methylated methyl ester o-methyl oxime [] [(a-methyl-3-trifluoromethyl-benzyl) imino] -oxi} -o-tolyl] -glyoxylic; dithiocarbamates, such as ferbam, mancozeb, maneb, metiram, propineb, thiram, zineb or ziram; N-halothiomethyldicarboximides, such as captafol, captan, diclofluanid, fluoromide, folpet, or tolifluanid; copper compounds, such as Bordeaux mixture, copper hydroxide, copper oxychloride, copper sulfate, cuprous oxide, mancobre, or oxine-copper; derivatives of nitrophenol, such as dinocap or nitrotal-isopropyl; organic phosphorus derivatives, such as edifenfos, iprobenfos, isoprothiolane, fosdifeno, pirazofos, or tolclofos-methyl; and other compounds of various structures, such as acibenzolar-S-methyl, anilazine, blasticidin-S, quinometionat, chloroneb, chlorothalonil, cymoxanil, diclone, diclomezine, dichloran, dietofencarb, dimetomorph, dithianone, etridiazole, famoxadone, fentin, ferimzone, fluazinam , flusulfamide, fenhexamide, fosetyl-aluminum, himexazole, casugamicin, metasulfocarb, penicharon, phthalide, polyoxins, probenazole, propamocarb, pyroquilon, quinoxifen, quintozene, sulfur, triazoxide, tricyclazole, triforine, or validamycin. Agrochemical compositions typically comprise from 0.1 to 99 percent, preferably from 0.1 to 95 percent by weight of a compound of formula I, from 99.9 to 1 percent by weight, preferably from 99.8 to 5 percent by weight of a solid or liquid auxiliary, and from 0 to 25 weight percent, preferably from 0.1 to 25 weight percent of a surfactant. Although the commercial products of preference will be formulated as concentrates, the end user will usually employ diluted formulations. The following examples illustrate the invention described above, without limiting its scope in any way. Temperatures are given in degrees Celsius.
Table 1: Compounds gives the formula 1.1 where Ri is methyl and n is the number one, and wherein the combination of R2, R3, A, and B corresponds to a line of Table A.
Table 2: Compounds of the formula 1.1 where i is ethyl and n is the number one, and where the combination of R2, R3, A, and B corresponds to a line of Table A.
Table 3: Compounds of the formula 1.1 where Ri is ethyl and n is the number zero, and where the combination of R2, R3, A, and B corresponds to a line of Table A.
Table 4: Compounds of the formula 1.1 where Ri is propyl and n is the number one, and where the combination of R2, R3, A, and B corresponds to a line of Table A.
Table 5: Compounds gives the formula 1.1 where Ri is propyl and n is the number zero, and where the combination of R2, R3, A, and B corresponds to a line of Table A.
Table 6: Compounds of formula I.1 wherein Ri is isopropyl and n is number one, and wherein the combination of R2, R3, A, and B corresponds to a line of Table A.
Table 7: Compounds of the formula 1.1 where Ri is isopropyl and n is the number zero, and wherein the combination of R2, R3, A, and B corresponds to a line of Table A.
Table 8: Compounds of the formula 1.1 where Ri is butyl and n is the number one, and where the combination of R2, R3, A, and B corresponds to a line of Table A.
Table 9: Compounds of the formula 1.1 where Ri is butyl and n is the number zero, and where the combination of R2, R3, A, and B corresponds to a line of Table A.
Table 10: Compounds of formula 1.1 wherein Ri is 3-chloro-propyl and n is the number one, and wherein the combination of R2, R3, A, and B corresponds to a line of Table A.
Table 11: Compounds of the formula 1.1 wherein Ri is dimethylamino and n is the number one, and ep where the combination of R2, R3, A, and B corresponds to a line of Table A.
Table 12: Compounds of the order 1.1 where Ri is phenyl and n is the number one, and where the combination of R2, R3, A, and B corresponds to a line of Table A.
Table 13: Compounds of the formula 1.1 where Ri is benzyl and n is the number one, and where the combination of R2, R3, A, and B corresponds to a line of Table A.
Table 14: Compounds of formula 1.2 wherein R2 is hydrogen, and wherein the combination of Ri »R3» and n corresponds to a line of Table B.
Table 15: Compounds d? the formula 1.3 where R2 is hydrogen, and where the combination of Ri, R3, and n corresponds to a line in Table B. Table 16: Compounds in order 1.4 wherein R2 is hydrogen, and wherein the combination of R? »R3» and n corresponds to a line of Table B.
Table 17: Compounds of formula 1.5 wherein R2 is hydrogen, and wherein the combination of Ri, R3, and n corresponds to a line of Table B.
Table 18: Compounds of formula 1.6 wherein R2 is hydrogen, and wherein the combination of Ri, R3, and n corresponds to a line of Table B.
Table 19: Compounds of formula 1.7 wherein R2 is hydrogen, and wherein the combination of Ri, R3, and n corresponds to a line of Table B. Table 20: Compounds of formula 1.8 where R2 is hydrogen, and where the combination of Ri »R3, and n corresponds to a line of Table B.
Table 21: Compounds of the formula I .9 wherein R2 is hydrogen, and wherein the combination of Ri »R3» and n corresponds to a line of Table B.
Table 22: Compounds of the formula I.10 wherein R2 is hydrogen, and wherein the combination of Ri »R3» and n corresponds to a line of Table B. Table 23: Compounds of the formula I.11 wherein R2 is hydrogen, and wherein the combination of Ri, R3 »n corresponds to a line of Table B.
Table 24: Compounds of formula 1.12 wherein R2 is hydrogen, and wherein the combination of Ri »R3» and n corresponds to a line of Table B.
Table 25: Compounds of the formula 1.13 wherein R2 is hydrogen, and wherein the combination of Ri »R3» and n corresponds to a line of Table B.
Table 26: Compounds of formula 1.14 (i) wherein R2 is hydrogen, and wherein the combination of Ri »R3» and n corresponds to a line of Table B.
Table 27: Compounds of the formula 1.15 wherein R2 is hydrogen, and wherein the combination of Ri, R3, and n corresponds to a line of Table B.
Table 28: Compounds of formula 1.16 wherein R2 is hydrogen, and wherein the combination of Ri, R3, and n corresponds to a line of Table B.
Table 29: Compounds of the formula 1.17 wherein R2 is hydrogen, and wherein the combination of Ri, R3 »n corresponds to a line of Table B.
Table 30: Compounds of the formula 1.18 wherein R2 is hydrogen, and wherein the combination of Ri, R3, and n corresponds to a line of Table B.
Table 3: Compounds of the formula 1.19 wherein R2 is hydrogen, and wherein the combination of R? »R3» and n corresponds to a line of Table B.
Table 32: Compounds of formula 1.20 wherein R2 is hydrogen, and wherein the combination of Ri, R3, and n corresponds to a line of Table B.
Table 33: Compounds gives the formula 1.21 wherein R2 is hydrogen, and wherein the combination of Ri, R3, and n corresponds to a line of Table B.
Table 34: Compounds of formula 1.22 wherein R2 is hydrogen, and wherein the combination of Ri, R3, and n corresponds to a line of Table B.
Table 35: Compounds gives the formula 1.23 ( 2. 3) wherein R2 is hydrogen, and wherein the combination of Ri »R3» and n corresponds to a line of Table B.
Table 36: Compounds of formula 1.24 wherein R2 is hydrogen, and wherein the combination of Ri, R3, and n corresponds to a line of Table B.
Table 37: Compounds of the formula 1.25 wherein R2 is hydrogen, and wherein the combination of Ri, R3 »and n corresponds to a line of Table B.
Table 38: Campings of the formula 1.26 wherein R2 is hydrogen, and wherein the combination of Ri »R3» and n corresponds to a line of Table B.
Table 39: Compounds of the formula 1.27 where R2 is hydrogen, and where the combination of Ri »3» and n corresponds to a line of Table B.
Table 40: Compounds gives the formula 1.28 wherein R2 is hydrogen, and wherein the combination of Ri »R3» and n corresponds to a line of Table B.
Table 41: Compound 3 of formula 1.29 wherein R2 is hydrogen, and wherein the combination of Ri, R3, and n corresponds to a line of Table B.
Table 42: Compounds of the formula I .30 where R2 is hydrogen, and where the combination of Ri »R3» and ß corresponds to a line of Table B.
Table 43: Compounds of formula 1.31 where R2 is hydrogen, and where the combination of Ri »R3» and n corresponds to a line of Table B.
Table 44: Compounds of formula 1.32 wherein R2 is hydrogen, and wherein the combination of Ri, R3, and n corresponds to a line of Table B.
Table 45: Compounds of the formula 1.33 wherein R2 is hydrogen, and wherein the combination of Ri, Rj, and n corresponds to a line of Table B.
Table 46: Compounds of the formula 1.34 wherein R2 is hydrogen, and wherein the combination of Ri »R3» and n corresponds to a line of Table B.
Table 47: Compounds of formula 1.35 wherein R2 is hydrogen, and wherein the combination of Ri »R3, and n corresponds to a line of Table B.
Table 48: Compounds given the I.36 where R2 is hydrogen, and where the combination of Ri, 3 »and n corresponds to a line of Table B. Table 49: Compounds given by the I.37 wherein R2 is hydrogen, and wherein the combination of Ri, R3, and n corresponds to a line of Table B. Table 50: Compounds gives the formula 1.38 wherein R2 is hydrogen, and wherein the combination of Rj, R3, and n corresponds to L.t.a line of Table B.
No. R2 R3 A B A.1 H phenyl -CH2- phenyl A.2 H phenyl -CHj- 4-CI-phenyl A.3 H phenyl -CH2- 3,4-di- CI-phenyl A.4 H phenyl -CH2- 2,4-d? -CI-phenyl A.5 H phenyl -CH2-4-Br-phenyl A.6 H -CH2-4-CH3- phenyl phenyl A.7 H phenyl -CH2- 4-Et-phenyl A.8 H phenyl -CH2- -0CH3- phenyl A.9 H phenyl -CH2-4-CF3-phenyl A.10 H phenyl -CH2-4-c.C5H9-phenyl A.11 H. phenyl -CH2- 3-0CH3-4-phenoxy-phenyl A.12 H phenyl -CH2- 3-OCH3-4-SCH3-phenyl A.13 H phenyl -CH2- -CH3 ?? C-phenyl A.14 H phenyl -CH2- 3-N02-phenyl A.15 H phenyl -CH2- 4-CN-phenyl A.16 H phenyl -CH2- 4-N (CH3) 2- phenyl A.17 H phenyl -CH (CH3) -phenyl A.18 H phenyl -CH (CH3) -4-CI-phenyl A.19 H phenyl -CH (CH3) -3,4-di-CI-phenyl A.20 H phenyl -CH (CH3) -2,4-di-CI-phenyl A.21 H phenyl -CH (CHa) -4-Br-phenyl A.22 H phenyl -CH (CH3) -4-CH3-phenyl A.23 H phenyl -CH (CH,) - 4-Et-phenyl A.24 H phenyl -CH (CH3) - -? CH3-phenyl A.25 H phenyl -CH (CH3) -4-CFr phenyl A.26 H phenyl -CH (CH3) - -c.C5H9-phenyl A.27 H phenyl -CH (CH3) - 3-0CH3-4-phenoxy-phenyl A.28 H phenyl -CH (CH3) -3-OCH3-4-SCH3-phenyl A.29 H phenyl -CH (CHÍ) - 4-CH3 ?? C-phenyl A.30 H phenyl -CH (CH,) - 3-NO2-phenyl A.31 H phenyl • CH (CH3) - 4-CN-phenyl A.32 H phenyl -CH (CH3) -4-N (CH3) 2- phenyl A.33 H phenyl -CH? Chp phenyl A.34 H phenyl -CH2CH2- 4-CI-phenyl A.35 H phenyl -CH2CH2- 3,4-d¡-CI-phenyl A.36 H phenyl -CH2CH2- 2,4-di-CI-phenyl A.37 H phenyl -CH2CH2"4-Br-phenyl A.38 H phenyl -CH2CH2-4-CH3-phenyl A.39 H phenyl -CH2CH2" 4-Et-phenyl A.40 H phenyl -CH2CH2"4-0CH3 - phenyl A.41 H phenyl -CH2CH2"4-CF3-phenyl A.42 H phenyl -CH2CH2- 4-C.C5H9-phenyl A.43 H phenyl • CH2CH2- 3-0CH3-4-phenoxy-phenyl A.44 H phenyl -CH2CH2"3-0CH3-4-SCHr phenyl A.45 H phenyl -CH2CH2 * 4-CH3OOC-phenyl A. 6 H phenyl -CH 2 CH 2 -3-N02-phenyl A.7 H phenyl -CH 2 CH 2"4-CN-phenyl A, 8 H phenyl -CH 2 CH 2 * 4-N (CH 3) 2-phenyl A. 9 H phenyl -CH (CH3) CH2- phenyl A.50 H phenyl -CH (CH3) CH2- 4-CI-phenyl A.51 H -CH (CH3) CH2- 3,4-di-CI-phenyl phenyl A.52 H phenyl -CH (CH3) CH2- 2,4-di-CI-phenyl A.53 H phenyl -CH (CH3) CH2- -Br-phenyl A.54 H phenyl -CH (CH3) CH2-4-CH3-phenyl A.55 H phenyl -CH (CH3) CH2- 4-Et-phenyl A.56 H phenyl -CH (CH3) CH2- 4 ^) CH3-phenyl A.57 H phenyl -CH (CH3) CH2- 4-CF3-phenyl A.58 H phenyl -CH (CH3) CH2- 4-c.C5H9-phenyl A.59 H phenyl -CH (CH3) CH2- 3-? CH3-4-phenoxy-phenyl A.60 H phenyl -CH (CH3) CH2- 3-? CHr4-SCH3-phenyl A.61 H phenyl -CH (CH3) CH2-4-CH3 ?? C-phenyl A.62 H phenyl -CH (CH3) CH2- 3-NO2- phenyl A.63 H phenyl -CH (CH3) CH2- 4-CN-phenyl A.64 H phenyl -CH (CH3) CH: 4-N (CH3) 2-phenyl A.65 H 4-CI-phenyl-CH2-phenyl A.66 H 4-CI-phenyl -CH2- 4-CI-phenyl A.67 H 4-Cl-phenyl -CH2- 3,4-di-CI- phenyl A.68 H 4-CI-phenyl-CH2- 2,4-di-CI-phenyl A.69 H 4-CI-phenyl -CH 2 * 4-Br-phenyl A.70 H 4-CI-phenyl -CH 2 -4-CH 3 -phenyl A.71 H 4-CI-phenyl -CH 2 -4-Et- phenyl A.72H 4-CI-phenyl -CH2- 4-? CH3-phenyl A.73 H 4-CI-phenyl -CH2- 4-CF3-phenyl A.74 H 4-CI-phenyl -CH2- 4?;. C5H9-phenyl A.75 H -CI-phenyl-CH2- 3-0CH3-4-phenoxy-phenyl A.76 H 4-d-phenyl-CH2- 3-OCH3-4-SCH3-phenyl A.77 H -CI-phenyl-CH2-4-CH3OOC-phenyl A.78 H 4-CI-phenyl -CH2- 3-N02-phenyl A.79 H 4-CI-phenyl -CH2- 4-CN-phenyl A.80 H 4-CI-phenyl -CH2- 4-N ( CH3) 2- phenyl A.81 H 4-CI-phenyl -CH (CH3) -phenyl A.82 H 4-CI-phenyl -CH (CH3) -4-CI-phenyl A.83 H 4-CI-phenyl -CH (CH3) - 3,4-di-CI-phenyl A.84 H -CI-phenyl -CH (CH3) -2,4-di-CI-phenyl A.85 H 4"CI-phenyl -CH (CH 3) -4-Br-phenyl A.86 H 4-CI-phenyl, H (CH 3) -4-CH 3 -phenyl A.87 H 4-CI-phenyl- CH (CH 3) -4-Et-phenyl A.88 H 4-CI-phenyl -CH (CH 3) -4-? CH 3 -phenyl A.89 H 4-CI-phenyl -CH (CH3) -4-CF3-phenyl A.90 H 4-CI-phenyl -CH (CH3) -4-c.C5H9-phenyl A.91 H 4-CI-f-enyl -CH (CH3) -3-? CH3-4-phenoxy-phenyl A.92 H 4-CI-phenyl -CH (CH3) -3? CH3-4-SCHj-phenyl A.93 H 4-CI-phenyl -CH (CH3) -4-CH3? OC-phenyl A.94 H 4-CI-phenyl -CH (CH3) -3-N? 2-phenyl A.95 H 4-CI-phenyl -CH (CH3) -4-CN-phenyl A.96 H 4-C | . phenyl -CH (CH3) -4-N (CH3) 2-phenyl A.97 H 4-CI-phenyl -CH2CH2- phenyl A.98 H 4-Cl-phenyl -CH2CH2"4-CI-f-enyl A.99 H 4-CI-phenyl -ChkCHj- 3,4-di- CI-phenyl A.100 H 4-CI-phenyl -CH2CH-2,4-di-CI-phenyl A.101 H 4-CI-phenyl -CH2CH2-4-Br-phenyl A.102 H 4-CI-phenyl -CH2CH2- 4-CH3- phenyl A.103 H 4-CI-phenyl -CH2CH2-4-Et-phenyl A.104 H 4-Cl-phenyl 4-OCH3-phenyl A.105 H 4-CI-phenyl -CH2CH2 * 4-CF3-phenyl A.106 H 4-CI-phenyl -CH2CH2 * 4-aC5H9-phenyl A.107 H 4-CI-phenyl -CH2CH2- 3-0CH3-4-phenoxy-phenyl A.108 H 4- CI-phenyl -CH2CH2- 3-0CH3-4-SCH3-phenyl A.109 H 4-CI-phenyl -CH2CH2-4-CH300C-phenyl A.110 H 4-CI-phenyl -CH CH2! " 3-N02-phenyl A.111 H 4-CI-phenyl -CH2CH2- 4-CN-phenyl A.112 H 4-CI-phenyl -CH2CH2- 4-N (CH3) 2- phenyl A.113 H 4-CI -phenyl -CH (CH3) CH2- phenyl A.114 H 4-CI-phenyl -CH (CH,) CH2- 4-Ct-phenyl A.115 H 4-CI-phenyl -CH (CH3) CH2- 3, 4-di-Cl-phenyl A.116 H 4-Cl-phenyl -CH (CH3) CH2- 2,4-di-CI-phenyl A.117 H 4-CI- phenyl -CH (CH3) CH2- 4- Br-phenyl A.118 H 4-CI-phenyl -CH (CH3) CH2- 4-CH3-phenyl A.119 H -CI- phenyl -CH (CH3) CH2- 4-Et-phenyl A.120 H 4- CI-phenyl -CH (CH3) CH2- 4-? CH3-f-enyl A.121 H 4-CI-phenyl -CH (CH3) CH2- 4-CF3-phenyl A.122 H 4-CI-phenyl -CH ( CH3) CH2- 4-c.C5H9-phenyl A.123 H 4-CI-f enyl -CH (CH3) CH2- 3-OCH3-4- phenoxy-phenyl A.124 H 4-CI-phenyl -CH (CH ,) CH2- 3-? CH3-4-SCH3-f enyl A.125 H 4-CI-phenyl -CH (CH3) CH2-4-CH3 ?? C-phenyl A.126 H 4-CI-phenyl -CH (CH,) CH2- 3-N? 2-phenyl A.127 H -CI-phenyl -CH (CH,) CH2- 4-CN-phenyl A.128 H 4-CI-phenyl -CH (CH,) CH 4-N (CH3) rphenyl A.129 H 3,4-di-CI-phenyl-CH2-phenyl A.130 H 3,4-d¡-CI-phenyl-CH2-4-CI-phenyl A.131 H 3,4-di-CI-phenyl-CH2- 3,4-di-CI-phenyl A.132 H 3,4-di-CI-phenyl-CH 2 -2,4-di-CI-phenyl A133 H 3,4-di-CI-phenyl-CH2-4-Br-phenyl A.134 H 3.4 -di-CI-phenyl -CH2- 4-CH3-phenyl A.135 H 3,4-di-CI-phenyl -CH2- 4-Et-phenyl A.136 H 3,4-dl-CI-phenyl -CH2 - 4-? CH3-phenyl A.137 H 3,4-dl-CI-phenyl -CH2- 4-CF3-phenyl A.138 H 3,4-di-Cl-phenyl -CH2- 4-c.C5H9- Phenyl A139 H 3,4-di-CI-phenyl-CH2- 3-0CH3-4-f-enoxyphenyl A.140 H 3,4-di-CI-phenyl-CH2- 3-0CH3-4-SCH3-phenyl A.141 H 3,4-di-CI-phenyl -CH2-4-CH300C-phenyl A.142 H 3,4-di-CI-phenyl -CH2- 3-N? 2-phenyl A.143 H 3, 4-di-CI-phenyl-CH2- 4-CN-phenyl A.144 H 3,4-di-CI-phenyl -CH2- 4-N (CH3) 2-phenyl A.145 H 3,4-di- CI-phenyl -CH (CH3) -phenyl A.146H 3,4-dl-CI-phenyl -CH (CH3) -4-CI-phenyl A.U7H 3,4-di-CI-phenyl -CH ( CH3) - 3,4-di-CI-phenyl A.148 H 3,4-di-CI-phenyl -CH (CH3) -2,4-di-CI-phenyl A.149 H 3,4-di- CI-.phenyl -CH (CH3) -4-Br-phenyl A.150 H 3,4-di-CI-phenyl -CH (CH3) -4-CH3-phenyl A.151 H 3,4-di-CI -phenyl -CH (CH3) -4-Et- | f enyl A.152 H 3,4-di-CI-phenyl -CH (CH3) -4-? CH3-phenyl A.153 H 3,4-di -CI-phenyl -CH (CH3) -4-CF3-phenyl A.154H 3,4-dl-CI-phenyl -CH (CH3) -4-c.C5H9-phenyl A.155H 3,4-di -CI-phenyl -CH (CH3) - 3-? CH3-4-f enoxypheni A.156 H 3,4-di-CI-phenyl -CH (CH3) - 3-0CH3-4-SCH3-f enyl A.157 H 3,4-di-CI-phenyl -CH (CH 3) - -CH 3? OC-phenyl A.158 H 3,4-dl-CI-phenyl -CH (CH 3) -3-N? 2-phenyl A.159 H 3,4-di-CI-phenyl -CH (CH 3) -4-CN-phenyl A.160 H 3,4-di-CI-f-enyl -CH (CH3) -4-N (CH3) 2-phenyl A.161 H 3,4-di-CI-phenyl -CH2CH phenyl A.162 H 3 , 4-di-CI-phenyl-CH2CH2-4-CI-phenyl A.163 H 3,4-di-CI-phenyl -CH CH2- 3,4-di-CI-f enyl A.164 H 3,4-di-CI-phenyl -Cp2CH2- 2,4-di-CI-phenyl A.165 H 3,4-di-CI-phenyl -CH2CH2 * 4-Br-phenyl A.166 H 3, -di-CI-phenyl -CH2Cp2-4-CH3-phenyl A.167 H 3, -di -CI-phenyl -CH2CH2-4-Et-phenyl A.168 H 3,4-di-CI-phenyl -CH2CH-4-? CH3-phenyl A.169 H 3,4-dl-CI-phenyl -CH 2 CH 2 -4-CF 3 -phenyl A.170 H -3,4-di-CI-f-enyl -CH2Cp2"4 ^: C5H9-phenyl A.171 H 3,4-di-CI-phenyl -CH2CH2- 3-0CH3-4- phenoxy phenyl A.172 H 3,4-di-CI-phenyl -CH2CH2- 3-0CH3-4-SCH3-f enyl A.173 H 3,4-di-CI-phenyl -CH2Cp2"4-CH300C-phenyl A.174 H 3,4-di-CI-phenyl -CH2CH2- 3-N? S-phenyl A.175 H 3,4-di-CI-f enyl -CH2Cp2-4-CNyphenyl A.176 H 3, 4-di-CI-phenyl -CH2CH2-4-N (CH3) 2-f enyl A.177 H 3.4 li-CI-phenyl -CH (CH3) CH2- phenyl A.178 H 3,4-di-CI-f-enyl -CH (CH3) CH2- 4-Cl-phenyl A.179 H 3,4-di-CI-phenyl -CH (CH3) CH2- 3,4-di-CI-phenyl A.180 H 3,4-di-CI-phenyl -CH (CH3) CH2- 2,4-di-CI-phenyl A.181 H 3,4-di-CI-phenyl -CH (CH 3) CH 2 -4-Br-phenyl A 1.82 H 3,4-di-CI-phenyl -CH (CH 3) CH 2 -4-CH 3 phenyl A.183 H 3,4-di-CI-phenyl -CH (CH3) CH2- 4-Et-phenyl A.184 H 3,4-di-CI-f enyl -CH (CH3) CH2- 4-0CH3 -phenyl A.185 H 3,4-di-CI-phenyl -CH (CH3) CH2- 4-CFrphenyl A.186H 3,4-di-CI-f-enyl -CH (CH3) CH2- 4-cC5H - phenyl A.187 H 3,4-di-CI-phenyl -CH (CH3) CH2- 3-? CH3-4-f enoxy-phenyl A.188 H 3,4-di-CI-phenyl -CH (CH3) CH2- 3-? CH3-4-SCH3-f enyl A.189 H 3,4-di-CI-phenyl -CH (CH3) CH2-4-CHa ?? C-phenyl A.190 H 3.4-di-CI-phenyl -CH (CH3) CH2- 3-N? 2-phenyl A.191 H 3,4-di-CI-phenyl -CH (CH3) CH2- 4-CN- f enyl A.192 H 3,4-di-CI-phenyl -CH (CH3) CH2- 4-N (CH3) 2-phenyl A.193 H 4-Br-phenyl -CH2CH2-phenyl A.194 H 4-Br-phenyl -CH CH * 4-CI-phenyl A.195 H -Br-phenyl -CH2CH2-4-CH3-phenyl A.196 H 4-Br-phenyl -CH2CH2-4-Et-phenyl A.197 H 4-Br-phenyl -CH2CH2-4-? CH3-phenyl A.198 H 4-Br-phenyl -CH2CH2- 3-? CH3-4-phenoxy-phenyl A.199 H 4-Br-f enyl -CH2CH2- 3-? CH3-4-SCH3-f enyl A.200 H 4-Br-phenyl -CH (CH 3) - phenyl A.201 H 4-Br-phenyl -CH (CH 3) - -CI-Eenyl A.202 H 4-Br-f-enyl -CH (CH 3) - 4-CH3-phenyl A.203 H 4-Br-phenyl -CH (CH3) -4-Et-phenyl A.204 H 4-Br-phenyl -CH (CH3) -4-? CH3-phenyl A.205 H 4-Br-phenyl -CH (CH3) -3-? CH3-4-phenoxy-phenyl A.206 H 4-Br-phenyl -CH (CH3) -3? CH3-4-SCH3-phenyl A.207 H 4-CF3-phenyl -CH2CH2-phenyl A.208 H 4-CF3-phenyl -CH2CH2- 4-CI-f enyl A.209 H 4-CF3-phenyl .CH2CH2-4-CHrfyl A.210 H 4-CFj-phenyl -CH 2 CH 2 -4-Et-phenyl A 211 H 4-CF 3 -f enyl -CH 2 CH 2 4- 4 CH 3 -f enyl A.212 H 4-CF3-phenyl -CH2CH2- 3-? CH3-4-phenoxy-phenyl A.213 H 4-CF3-phenyl -CH2CH2- 3-? CH3-4-SCH3-f enyl A.214 H 4-CF3-phenyl -CH (CH3) -phenyl A.215 H 4-CF3-phenyl -CH (CH3) -4-CI-phenyl A.216 H 4-CF3-f enyl -CH (CH3 ) - 4-CH3-f enyl A.217 H 4-CF3-phenyl -CH (CH3) -4-Et-phenyl A.218 H 4-CF3-phenyl -CH (CH3) -4-? CH3-f enyl A.219 H 4-CF3-phenyl -CH (CH3) - 3-0CH3-4-f-enoxyphenyl A.220 H 4-CF3-phenyl -CH (CH3) - 3-0CH3-4-SCH3-phenyl A.221 H -CH3-pheni: Lo -CH2CH2- phenyl A.222H 4-CH3-phenyl -CH2CH2-4-CI-phenyl A.223H 4-CH3-phenyl -CH2CH2-4-CH3-phenyl A. 224 H 4-CH3-phenyl -CH2CH2-4-Et-phenyl A.225H 4-CH3-phenyl -CH2CH2-4-0CH3-phenyl A.226 H 4-CH3-f enyl -CH2CH2- 3-? CH3-4-f enoxyphenyl A.227 H 4-CH3- phenyl -CH2CH2- 3-? CH3-4-SCH3-f enyl A.228 H 4-CH3-phenyl -CH (CH3) -phenyl A.229 H 4-CH3-phenyl -CH (CH3) -4-CI-phenyl A.230 H 4-CH3-phenyl -CH (CH3) -4-CH3-f enyl A.231 H 4-CH3-phenyl -CH (CH3) -4-Et-phenyl A.232 H 4-CH3-phenyl -CH (CH3) -4-? CH3-phenyl A.233 H 4-CH3-phenyl -CH (CH3) - 3-0CH3-4-f enoxy-phenyl A.234 H 4-CH3-f enyl -CH (CH3) -3? CH3-4-SCH3-f enyl A.235 H 4-F-phenyl -CH CH2"4-CI-phenyl A.236 H 4-F-phenyl -CH2CH2" 4 JH3-phenyl A.237 H 4-F-f enyl -CH2CH "4-0CH3-phenyl A.238 H 4-F- phenyl -CH (CH3) -4-CI-phenyl A.239 H 4-F-phenyl -CH (CH3) -4-CH3-phenyl A.240 H 4-F-phenyl -CH (CH3) - 4-? CH3-phenyl A.241 H 4-? CF3-phenyl -CH2CH2- 4-CI-phenyl A.242 H 4-0CF3-phenyl -CHjCrk "4-CHrf enyl A.243 H 4-OCF3-phenyl -CH2CH2" 4-? CHs -phenyl A.244 H 4-OCF3-phenyl -CH (CH3) -4-CI-phenyl A.245 H 4-? CF3-phenyl -CH (CH3) -4-CHj-phenyl A.246 H 4-? CF3- phenyl -CH (CH3) -4-? CH3-f enyl A.247 CH3 4-CI-phenyl -CH2CH2"4-CI-phenyl A.248 CH3 4-CI-phenyl -CH2CH2 * 4-CHrphenyl A.249 CH3 4-CI-phenyl -CH2CH2-4-? CHa-phenyl A.250 CH3 4-CI-phenyl -CH (CH3) -4-CI-phenyl A.251 CH3-C-phenyl -CH (CH3) -4-CHrphenyl A.252 CH3 4-CI-phenyl -CH ( CH3) - 4-? CHs-phenyl A.253 CH3 3,4-di-CI-f enyl -CH2CH2"4-CI-phenyl A.254 CH3 3,4-di-CI-phenyl -CH2CH2" 4-CHrphenyl A.255 CH3 3,4-dl -CI-phenyl -CH2Crl2-4-OCH3-phenyl A.256 CH3 3,4-di-CI-phenyl -CH (CH3) - 4 ^ 1-phenyl A.257 CH3 3,4-di-CI-phenyl -CH (CH3) -4-CHrf enyl A.258 CH3 3,4-di-CI-phenyl -CH (CH3) -4-? CH3-phenyl A.259 CH3 4-Br-phenyl -CH2CH2 * 4-Cl-phenyl A.260 CH3 4-Br-phenyl -CH2CH2"4-CHrphenyl A.261 CH3 4-Br-phenyl -CH2CH2" 4-OCHrf enyl A.262 CH3 4-Br-phenyl -CH (CH3) -4-CI-phenyl A.263 CH3 4-Br-phenyl -CH (CH3) -4-CH3-phenyl A.264 CH3 4-Br-phenyl-CH (CH3) -4-OCHa-phenyl A.265 H 3,4-d¡-? CH3-phenyl -CH2CH2- 4-CI-phenyl A.266 H 3,4-d¡-? CH3-phenyl -O-feC-Hj- 4-CH3-phenyl A.267 H 3,4-di-0CH3-phenyl -ChfeCHa- 4-OCH3-phenyl A.268 H 3,4-di-? CH3-phenyl -CH (CH3) -4-CI-phenyl A.269 H 3,4-di-? CH3-phenyl -CH (CH3) -4-CH3-phenyl A.270 H 3,4-di-OCHa-phenyl-CH (CH 3) -4-OCH-phenyl A.271 H 3,4-d¡-CH3-phenyl -CH2CH2-4-CI-phenyl A.272 H 3,4-di-CH3-phenyl -CH2CH2-4-CH3-phenyl A.273 H 3,4-di-CH 3 -phenyl -CH 2 CH > - 4-? CH3-phenyl A.274 H 3,4-d¡-CH3-phenyl -CH (CH3) - 4-CI-phenyl A.275 H 3,4-di-CH3-phenyl -CH (CH3) -4-CH3-phenyl A.276 H 3,4-di-CH3-phenyl -CH (CH3) -4-? CHa-phenyl A.277 H 4-CI-phenyl -CH2CH2-3-OCH-phenyl A.278 H 4-CI-phenyl - (CHjJr 3,4-d¡-CH3? Ifenyl Table B < (where Et means ethyl) No., n R3 B.1 CH3 1 4-CI-phenyl B.2 Et 0 4-CI-phenyl B.3 Et 1 -CI-phenyl B.4 1 -propyl 0 4-CI-phenyl B.5 1 -propyl 1 4-CI-f enyl B.6 2-propyl 0 4-CI-phenyl B.7 2-propyl 1 4-Cl-phenyl B.8 1-butyl 0 4-CI-? phenyl B.9 1 -butyl 1 4-CI-phenyl B.10 N (CH3) 2 0 4-CI-phenyl B.11 N (CH3) 2 1 -Cl-f enyl B.12 1-pyrrolidine 1 .c, .f.
B.13 3-CI-propyl 1 4-CI-phenyl B.14 2-Me-2-propyl 0 4-CI-phenyl B.15 2-Me-propyl 4-CI-phenyl B.16 CF3 4-CI-phenyl B.17 CH2-CF3 4-CI-phenyl B.18 4-CI-phenyl vinyl B.19 Cyclopentyl 4-CI-phenyl B.20 cyclohexyl 4-CI-phenyl B 21 cyclopentyl-C-phenyl B.22 cyclohexyl 4-CI-phenyl B.23 CH2-S02-CH3 4-CI-phenyl B.24 phenyl 4-CI-phenyl B.25 benzyl 4-CI-phenyl B.26 4-M? -phenyl 4-CI-phenyl B.27 4-MeS-phenyl 4-CI-phenyl B.28 4-CF3-phenyl 4-CI-phenyl B.29 4-CF30-phenyl 4-CI-phenyl B.30 4-MeO-phenyl 4-CI-phenyl B.31 3-CH3OOC-phenyl 4-CI-phenyl B.32 3-CH3CO-phenyl 4-CI-phenyl B.33 4-CI- phenyl 4-CI-phenyl B.34 3-N02-phenyl-C-phenyl B.35 3-CN-phenyl 4-CI-phenyl B.36 CH3 3,4-di-CI-phenyl B.37 Et 0 3,4-d¡-CI-phenyl B.38 Et 3,4-di-CI-phenyl B.39 1-propyl 0 3,4-d? -CI-phenyl B.40 1-propyl 3,4-d? -CI-phenyl B.41 2-propyl 0 3.4-d? -CI-phenyl B.42 2-propyl 3,4-di-Cl-phenyl B. 3 1-butyl or 3,4-d? -CI-phenyl B.44 1-but i lo 3,4-d? -CI-phenyl B.45 N (CH3) 2 0 3.4-d? -CI-phenyl B.46 N (CH3) 2 3,4-di-CI-phenyl pyrrolidine 3,4-di-CI-phenyl B, 7 1- B, 48 3-Cl-propyl 3,4-di-CI-phenyl B.49 2- e-2-propyl 0 3,4-di-CI-phenyl 3,4-di-CI-phenyl B.50 2-Me-propyl B.51 CF3 3,4-di-CI-phenyl B.52 CH2-CF3 3,4-di-CI-phenyl vinyl 3,4-di-CI-phenyl B.53 B.54 cyclopentyl 0 3,4-di-CI-phenyl or 3,4-di-CI-phenyl B.55 cyclohexy clopentyl 3,4-di-CI-phenyl B.56 ci B.57 cyclohexyl 3,4-di-CI-phenyl CH2-SOrCH3 3,4-di-CI-phenyl B.58 3,4-di-CI-phenyl B.59 phenyl B.60 3,4-di-CI-phenyl benzyl lo 4-Me-phenyl 3,4-di-CI-phenyl B.61 eS-phenyl 3,4-di-CI-phenyl B.62 4- 4-CF3-phenyl 3,4-di-CI-phenyl B.63 B.64 4-CF30-phenyl 3,4-di-CI-phenyl 3,4-di-CI-phenyl B.65 4- eO-phenyl 3-CH 3 OOC-phenyl. 3,4-di-CI-phenyl B.66 B.67 3-CH3CO-phenyl 3,4-di-CI-phenyl 4-Cl-phenyl 3,4-di-CI-phenyl B.68 2-phenyl 3,4-di-CI-phenyl B.69 3-N0 3-CN-phenyl 3,4-di-CI-phenyl B.70 B.71 CH3 phenyl B.72 Et 0 phenyl phenyl B.73 Et B.7 2-propyl 0 phenyl phenyl phenyl B.75 2-pro B.76 N (CH3) 2 phenyl 4-8r-phenyl B.77 CH3 B.78 Et 0 4-Br-phenol B.79 Et 4-Br-phenyl B.80 2-propyl 4-Br-phenyl B.81 2-propyl 4-Br-phenyl B.82 N (CH3) 2 4-Br-phenyl B.83 CH3 4-CH3-phenyl B.84 Et 4-CH 3 -phenyl B.85 Et 4-CH3-phenyl B.86 2-propyl 4-CH3-phenyl B.87 2-propyl 4-CH3-phenyl B.88 N (CH3) 2 4-CH3-phenyl B.89 CH3 4-CH30-phenyl B.90 Et 4-CH3? -phenyl B.91 Et -CH3? -f enyl B.92 2-propyl 4-CH30-phenyl B.93 2-propyl 4-CH30-phenyl B.94 N (CH3) 2 4-CH30-phenyl B.95 CH3 4-CF3-phenyl B.96 Et 4-CF3-phenyl B.97 Et 4-CF3-phenyl B.98 2-propyl 4-CFj-feniio B.99 2-propyl 4-CF3-phenyl B.100 N (CH3) 2 4-CF3-phenyl B.101 CH3-F-phenyl B.102 Et 4-F-phenyl B.103 Et 4-F-f enyl B.104 2-propyl 4-F-phenyl B.105 2-propyl 4-F-phenyl B.106 N (CH3) 2 4-F-phenyl B.107 CH3 4-CF30-phenyl B.108 Et 4-CF3? -phenyl B.109 Et 4-CFjO-phenyl B.110 2-propyl -CF30-phenyl B.111 2-propyl 4-CF, 0-phenyl B.112 N (CH3) 2 4-CF30-f enyl B.113 CH3 3,4-di-CH3-f enyl B.1 14 Et 3,4-di-CH3-phenyl B.115 Et 3.4- di-CH3-phenyl B.116 2-propyl 3,4-di-CH3-f enyl B.1 17 2-propyl 3,4-d¡-CH3-phenyl B.1 18 N (CH3) 2 3.4 -di-CH3-phenyl B.119 CH3 4-vinyl-phenyl B.120 Et 4-vinyl-phenyl B.121 Et 4-vinyl phenyl B.122 2-propyl 4-vinyl phenyl B.123 2-propyl 4-vinyl-phenyl B.124 N (CH3) 2 4-vinyl-phenyl B.125 CH3 4- ethynyl-phenyl B.126 Et 4- ethynylphenyl B.127 Et 4-ethynylphenyl B.128 2- propyl 4- ethynyl-phenylene B.129 2-propyl 4-ethynyl-phenyl B.130 N (CH3) 2 4-ethynyl-phenyl B.131 CH3 4- cyclopentyl-phenyl B.132 Et 4-cyclopentyl-phenyl B.133 Et 4-cyclopentyl-phenyl B.134 2-propyl 4-cyclopentyl-phenyl B.135 2-propyl 4-cyclopentyl-phenyl B.136 N (CH3) 2-cyclopentyl-phenyl B.137 Et 4- allyl-O-phenyl B.138 Et 4- allyl-O-phenyl B.139 2-propyl 4-allyl-O-phenyl B.140 2-propyl 4-al i 1-0-phenyl B.141 N (CH3 ) 2 4-allyl-O-phenyl B.142 Et 4-CH3S-f enyl 8.143 Et 4-CH3S-phenyl B.144 2-propyl 4-CH3S-phenyl B.145 2-propyl 1-CH3S-phenyl B.146 N (CH3) 2 1 4-CHaS-phenyl B.147 Et 0 4-CH3-S02-phenyl B.148 Et 1 4-CH3-S? 2-phenyl B.149 2-propyl 0 4-CH3-S02-f enyl B.150 2-propyl 1 4-CH3-S02-phenyl B.151 N (CH3) 2 1 -CH3-S? 2-f enyl B.152 Et 0 3-CH3C0-f enyl B.153 Et 1 3-CH3C0-phenyl B.154 2-propyl 0 3-CH3C0-f enyl B.155 2-propyl 1 3-CH3C0-phenyl B.156 N (CH3) 2 1 3-CH3C0-f enyl B.157 Et 0 3-CH300C-phenyl B.158 Et 1 3-CH3OOC-phenyl B.159 2-propyl 0 3-CH3O? C-phenyl B.160 2-propyl 1 3-CH3O? C-phenyl B.161 N (CH3) 2 1 3-CH3O? C-phenyl B.162 Et 0 4-N (CH3) 2-f enyl B.163 Et 1 4-N (CH3) 2-phenyl B.164 2-propyl 0 4-N (CH3) 2-f enyl B.165 2-propyl 1 4-N (CH3) 2-phenyl B.166 N (CH3) 2 1 4-N (CH3) rhenyl B.167 Et 0 3-N02-phenyl B.168 Et 1 3-NO2-phenyl B.169 2-propyl 0 3-N02-phenyl B.170 2-propyl 1 3-N02-phenyl B.171 N (CH3) 2 1 3-N02-phenyl B.172 Et 0 4-CN-phenyl B.173 Et 1 4-CN-phenyl B.174 2-propyl 0 4-CN-phenyl B.1 5 2-propyl 1 4-CN-f enyl B.176 N (CH3) 2 1 4-CN-phenyl B.177 Et 0 4 OH-phenyl B.1 8 Et 1 4-OH-phenyl B.179 2- propi.lo 0 4-OH-phenyl B.180 2-propylole 1 4-OH-phenyl B.181 N (CH3) 2 1 4-OH-phenyl B.182 Et 0 2-thienyl B.183 Et 1 2-thienyl B.184 2-propyl 0 2 -thienyl B.185 2-propylole 1 2-thienyl B.186 N (CH3) 2 1 2 -thienyl B.187 Et 0 3-thienyl B.188 Et 1 3-thienyl B.189 2-propyl 0 3-thienyl B.190 2. prop i .lo 1 3- thienyl B.191 N (CH3) 2 1 3-thienyl B.192 Et 0 2-furanyl B.193 Et 1 2-furanyl B.194 2-propyl 0 2- furanyl B.195 2- rop i .lo 1 2-furanyl B.196 N (CH3) 2 1 2 -furanyl B.197 Et 0 1-naphthyl B.198 Et 1 1-naphthyl B.199 2-propyl 0 1-naphthyl B.200 2-propi .lo 1 1-naftilo B.201 N (CH3) 2 1 1-naphthyl B.202 Et 0 2-naphthyl B.203 Et 1 2-naphthyl B.204 2-propyl 0 2-naphthyl B.205 2-propyl 1 2-naphthyl B.206 N (CH3) 2 1 2-naphthyl B.207 Et 0 3- pyridyl B.208 Et 1 3- pyridyl B.209 2-propyl 0 3-p i ridyl B.210 2-propyl 1 3.p? ridyl B.211 N (CH3) 2 1 3-pyridyl B.212 Et 0 2- benzothiazole i lo B.213 Et 1 2- benzothiazole i lo B.214 2-propyl 0 2- benzothiazol ilo B.215 2-propyl 1 2- benzothiazolyl B.216 N (CH3) 2 1 2-benzothiazolyl B.217 Et 0 3- indolyl B.218 et 1 3-indolyl B.219 2-propyl 0 3-indolyl B.220 2- prop i.lo 1 3-indolyl B.221 N (CH3) 2 1 3-indolyl B.222 Et 0 3- CF3-phenyl B.223 Et 1 3-CF3-phenyl B.224 2-propyl 0 3-CF3-phenyl B.225 2-propyl 1 3-CF3-phenyl B.226 N (CH3) 2 1 3-CF3-phenyl B.227 Et 0-4 phenoxy-pheni lo B.228 Et 1 4-phenoxy-phenyl B.229 2-propi.lo 0 4-f enoxi-phenyl B.230 2- rop i .lo 1 4-phenoxy-phenyl B.231 N (CH3) 2 1 4-f-enoxyphenyl B.232 Et 0 4-ethoxy phenyl B.233 Et 1 4-ethoxy phenyl B.234 2-propyloyl 0 4-ethoxy-phenyl B.235 2-propylole 1 4-ethoxy phenyl B.236 N (CH3) 2 1 4-ethoxy-phenyl B.237 Et 0 3.4-0-CH2-0-phenyl B.238 Et 1 3.4-0-CH2-0-phenyl B.238 2-propylole or 3,4-0-CH2-0-phenyl B.240 2-propylole 1 3, -0-CH2-0-phenyl B.241 N (CH3) 2 1 3.4-0-CH2-0-phenyl B.242 Et 0 3.4-0-CH2CH2 -? - f enyl B.243 Et 1 3. -0-CH2CH2 -? - phenyl B.244 2-propyl 0 3,4 -? - CH 2 CH 2 -? - phenyl B.245. Propyl 1 3,4 -? - CH2CH2 -? - phenyl B.246 N (CH3) 2 1 3.4 -? - CH2CH2 -? - phenyl B.247 Et 0 4-biphenyl B.248 Et 1 4-biphenyl B.249 2- propyl 0 4-biphenyl B.250 2- propyl 1 4-biphenyl B.251 N (CH3) 2 1 4-biphenyl B. 252 Et 0 4- isopropyl-phenyl B.253 Et 1 4-isopropyl-phenyl B.254 2- propyl 0 4-isopropyl-phenyl B.255 2-propyl 1 4-isopropyl-phenyl B.256 N (CH3) 2 1 4-isopropyl-phenyl B.257 Et 0 4-CH3 ?? C-phenyl B.258 Et 1 4-CH300C-phenyl B.259 2-propyl 0 4-CH300C-phenyl B.260 2-propyl 1 4-CH3 ?? C-phenyl B.261 N (CH3) 2 1 4-CH3 ?? C-phenyl B.262 Et 0 3,4-di-F-phenyl B.263 Et 1 3,4-d¡-F-phenyl B.264 2 -propyl 0 3,4-di-F-phenyl B.265 2-propyl 1 3,4-d-F-phenyl B.266 N (CH3) 2 1 3,4-di-F-phenyl B.267 Et 0 4-tertiary butyl-phenyl B.268 Et 1 4-tertiary butyl-phenyl B.269 2-propyl 0 4-tertiary butyl-phenyl B.270 2-propyl 1,4-tertiary butyl-phenyl B.271 N (CH3) 2 1 4-tertiary butyl-phenyl B.272 Et 0 3-CI-phenyl B.273 Et 1 3-CI-phenyl B.274 2-propyl 0 3-CI-phenyl B.275 2-propyl 1 3-Cl-phenyl B.276 N (CH3 2 1 3-CI-phenyl B.277 Et 0 3,5-di-CI-phenyl B.278 Et 1 3,5-di-CI-phenyl B.279 2-propyl 0 3,5-di-CI-phenyl B.280 2.propyl 1 3,5-di-CI-phenyl B.281 N (CH3) 2 1 3,5-di-CI-phenyl B.282 Et 0 3- pyrazolyl B.283 Et 1 3- pyrazolyl B.284 2- propyl 0 3-pyrazolyl B.285 2- propyl 1 3-pyrazolyl B.286 N (CH3) 2 1 3-pyrazolyl B.287 Et 0 1 -Me-2-benzimidazolyl B.288 Et 1 1- e-2-benzimidazolyl B.289 2- propyl 0 1-Me-2-benzimidazolyl B.290 2- propyl 1 1-Me-2-benzimidazolyl B.291 N (CH3) 2 1 l-M? -2-benzimidazolyl B.292 Et 0 2-thiazolyl B.293 Et 1 2-thiazolyl B.294 2-propyl 0 2-thiazolyl B.295 2-propyl 1 2-thiazolyl B.296 N (CH3) 2 1 2-thiazolyl B. 297 Et 0 1- e-3-indolyl B.298 Et 1 1-M? -3-indolyl B.299 2-propyl 0 1-M? -3-indolyl B.300 2-propyl 1 1- e-3-indolyl B.301 N (CH3) 2 1 1-Me-3-indolyl B.302 Et 0 2-pyrrolyl B.303 Et 1 2-pyrrolyl B.304 2-propyl 0 2-pyrrolyl B.305 2-propyl 1 2-pyrrolyl B.306 N (CH3) 2 1 2-pyrrolyl B. 307 et 0 2- imidazolyl B.308 Et 1 2- imidazolyl B.309 2-propyl 0 2- imidazolyl B.310 2- propi lo 1 2- imidazolyl B.311 N (CH3) 2 1 2-imidazolyl B.312 Et C i 4-imidazolyl B.313 Et 1 4-imidazolyl B.314 2-propyl () 4-imidazolyl B.315 2-propyl 1 j.midazolyl B.316 N (CH3) 2 -imidazolyl B.31 1-propyl 4-CF3? -phenyl B.318 Et i 3,4-di-CH3? -f enyl B.319 1- ropilo 4-Br-phenyl B.320 N (CH3) 2 3,4-di-CH3? -phenyl B.321 1-propyl "" 3,4-dl-CHa? -phenyl B.322 1-propyl 4-N (CH3) rhenyl B.323 1-propyl 4-CH3S-phenyl B.324 Et 3-CH3- > phenyl B.325 N (CH3) 2 3-CH3-phenyl B.326 1-propyl 3-CH3-phenyl B.327 1-propyl 4-CH3-phenyl B.328 N (CH3) 2 3-CF3-f enyl B.329 1-propyl 3-CF3-phenyl B.330 1 -propi lo 4-f enoxyphenyl B.331 1-propyl 4- ethoxy? phenyl B.332 1-propyl 3,4-0-CH2-0-phenyl B.333 CH3 3-F, 4-CI-f nyl B.334 Et 3-F.4-CI-phenyl B.335 N (CH3). 3-F, 4-Cl-phenyl B.336 N (CH3) 2 1 3-CF3,4-CI-phenyl B.337 Et 3-CF3,4-CI-phenyl B.338 CH3 1 3-CF3,4-CI-phenyl B.339 Et 1 3-F-feniIo B.340 Et 1 5 -Me, 2-thienyl B.341 1-propyl 1 2 - naphthyl B.342 n-butyl and 4-Br-phenyl B.343 Vinyl 1 4-Br-phenyl B.344 4-Me-phenyl 1 4-Br-phenyl B.345 Et 1 2-CH3? -phenyl B.346 Et 1 3-CH30-phenyl B.347 Et 1 2-Offenyl B.348 Et 1 3,5-dpF-phenyl B.349 Et 1 3-CH3,4-CH3? -phenyl B.350 Et 1 4-NHC0CHphenyl B.351 Et 1 3,5-di-CH30 -phenyl B.352 Et 1 4 -pyrrolidino-f enyl B.353 Et 1 3-Br-phenyl B.354 Et 1 3-CH3?, 4-propargyloxy-phenyl B.355 Et 1 4-Br, 2-thienyl B.356 Et 2 -f luorenyl B.357 Et 4-CH (? -et) 2-phenyl B.358 Et 4- (4'-CI-ffenoxy) - filo B.359 Et 5-Mβ, 2- furanyl B.360 Et 3-CI-phenyl B.361 Et 4-NOrphenyl B.362 Et 2,4-d¡-CH3? -phenyl B.363 Et 1 2.4 -di-CI-f enyl * B.364 N (CH3 / 2 1 5-Me, 2- furanyl B.365 N (CH3) 2 1 3-F-phenyl B.366 N (CH3) 2 1 5-Mβ , 2-thienyl B.367 N (CH3) 2 1 2 -CH3? -phenyl B.368 N (CH3 / 2 1 3-CH30- phenyl B.369 N (CH3) Í 1 2-CI-phenyl B.370 N (CH 3; 2 1 3,5-di-F-phenyl B 371 N (CH 3) 2 1 3-CH 3, 4-CH 3? -f enyl B 3 72 N (CH 3) 2 1 4-N 2 -phenyl B.373 N (CH3) 2 1 3,5-di-CH3? -phenyl B.374 N (CH3) 2 1 2.4-d? -CH3? -f enyl B.375 N (CH3k 1 2.4-di) -CI-phenyl B.376 N (CH3) 2 4 -pyrrolidino-phenyl B.377 N (CH3) 2 3-Br-phenyl B.378 N (CH3) 2 3-CH30.4- ropargyloxyphenyl B.379 N (CH3) 2 4-Br, 2-thienyl B.380 N (CH3) 2 4 - (4'-Cl-phenoxy) -phenyl B.381 N (CH3) 2 2 -f luorenyl Ex Emploses of Preparation for the compounds of the formula I: Example 1: 2- (4-chloro-phenyl) -N- [2- (3,4-dimethoxy-phenyl) -ethyl] -2-ethanesulfonylamino-acetamide To a vigorously stirred solution of 8 grams of amino- (4-chloro-phenyl) -acetic acid (J. Chem. Soc. 1962, 1440), and 1.7 grams of sodium hydroxide in 125 milliliters of water at 0 ° C, a solution of 5.6 grams of ethanesulfonyl chloride in 100 milliliters of toluene, and a solution of 1.7 grams of sodium hydroxide in 100 milliliters of water for 20 minutes are added simultaneously. The reaction mixture is stirred for 45 minutes at 0 ° C. Stirring is continued for 3 hours, during which time, the reaction mixture is allowed to warm to room temperature. The organic phase is separated and extracted with 100 milliliters of a 2N sodium hydroxide solution. The water phases are combined and acidified with concentrated hydrochloric acid until pH <; 2, and extracted with ethyl acetate (2 x 500 milliliters). The organic phases are washed with a brine soln (2 x 150 milliliters), dried over magnesium sulfate, and evaporated to dryness, yielding (4-chloro-phenyl) -ethanesulfonaminoacetic acid as a yellow oil. To a soln of 2.5 grams of the (4-chloro-phenyl) -ethanesulfonaminoacetic acid, 1.6 grams of homoveratrilamine, and 3.1 milliliters of N, N-di-isopropylethylamine in 40 milliliters of N, N-dimethylformamide, are added 4 grams of benzotriazol-1-yloxy-tris (dimethylamino) phosphonium hexafluorophosphate. The reaction mixture is stirred for 2 hours at room temperature. 500 milliliters of water are added, and extracted twice with ethyl acetate (2 x 300 milliliters). The organic phases are washed with brine (2 x 100 milliliters), combined, dried over magnesium sulfate, and evaporated to dryness. The residue is purified by column chromatography by evaporation on silica gel using ethyl acetate / hexane, 2: 1, as eluent. 2- (4-chloro-phenyl) -N- [2- (3, 4-dimethoxy-phenyl) -ethyl] -2-ethanesulfonylamino-acetamide (compound of Table 14, B.3) is obtained, and recrystallized from ethyl acetate / hexane, m.p. 136-138 ° C.
Example 2: 2-benzo [1,3] -dioxol-5-yl-N- [2- (3, 4-dimethoxy-phenyl) -ethyl] -2- (N1, N '-dimethylsulfamido) -acetamide A mixture of 4.78 grams (25.0 millimoles) of 4- (2-isocyano-ethyl) -1,2-d-methoxy-benzene, 4.5 grams (30 millimoles) of piperonal, 3.15 grams (50 millimoles) of ammonium formate in 25 milliliters of methanol (which has been previously purged with a stream of nitrogen), is heated at reflux for 18 hours. The solution is cooled to 0 ° C, and 10 milliliters of 10M HCl in methanol are added. The reaction mixture is stirred at room temperature for 10 hours. Then the mixture is extracted twice with 150 milliliters of ice water. The water phase is made basic by the addition of 2N NaOH (pH = 14), and extracted with ethyl acetate. 7.33 grams (82 percent) of 2-amino-2-benzo [1,3] -dioxol-5-yl-N- [2- (3, 4-dimethoxy-phenyl) -ethyl] -acetamide are isolated as a orange oil, which is further reacted without purification. 1.9 grams (5.3 mmol) of 2-amino-2-benzo [1,3] -dioxol-5-yl-N- [2- (3, 4-dimethoxy-phenyl) -ethyl] -acetamide are dissolved in 20 milliliters of tetrahydrofuran, and cooled to 0 ° C. 0.8 milliliters (7.42 millimoles) of N, N-dimethylsulphamoyl chloride and 2.22 milliliters (15.9 millimoles) of triethylamine are added, and the mixture is stirred for 15 hours at room temperature. After dilution with ethyl acetate, the mixture is extracted with ice cold water. Evaporation of the solvent gives an oil, which is crystallized from toluene to give 1.08 grams (44 percent) of 2-benzo [1,3] dioxol-5-yl-N- [2- (3,4-dimethoxy). phenyl) -ethyl] -2- (N1, N '-dimethylsulfamido) -acetamide (compound of Table 14, B.241) as a white solid (mp 137.5-139 ° C). From the mother liquor, 0.85 grams (35 percent) of the compound are additionally isolated. The compounds given in Table C can be obtained analogously to Examples 1 or 2.
Table C Compound is echemistry, a Physical Data p. f. or 'M (eSMS) Tab.2, A.277 R.S 113-115 Tab.2, A.278 R, S 123-124 ° C Tab.14, B.3 R.S 136-138 ° C Tab.14, B.38 R.S 473 (-1) - Tab.14, B.38 R 126-127 ° C Tab.14, B.46 R oil Tab.14, B.73 R.S 157-159 ° C Tab.14, B.77 R, S 167-168.5 ° C Tab.14, B.79 R.S 143-145 ° C Tab.14, B.81 R, S 497 (M-1) - Tab.14, B.82 R.S 14-116 ° C Tab.14, B.85 R, S 135-136 ° C Tab.14, B.88 R.S 118.5-119.5 ° C Tab.14, B.91 R, S 116-127 ° C; 437 (M + 1) + Tab.1, B.94 R, S 452 (M + 1) + Tab.14, B.97 R, S 150-153 ° C Tab.14, B.103 R, S 161-163 ° C Tab.14, B.109 R.S 154-155 ° C Tab.14, B.112 R.S 506 (M + 1) + Tab.14, B.143 R.S 155.5-156.5ßC Tab.14, B.146 R.S 102.5-104.5"C Tab.14, B.163 R.S 146-148-0 Tab.14, B.166 R.S 109-110-C Tab.14. B.173 R.S 145-147 ° C Tab.14, B.176 R.S 445 (M-1) - Tab.14. B.183 R.S 136-137.5 ° C Tab.1, B.186 R.S 426 (M-1) - Tab.14, B.193 R.S 395 (M-1) - Tab.14, B.196 R.S 410 (M-1) - Tab.14, B.198 R.S 144-146 ° C Tab.14, B.201 R.S 470 (M-1 > - Tab.4, B.203 R, S 135-136.5 ° C Tab.14, B.206 RS 472 (M + 1) + Tab.14, B.223 RS 103-107 ° C Tab.14, B.228 RS 134-136ßC Tab.14, B.231 RS 128.5-131 ° C Tab.14, B.233 R.S 137.5-138.5 ° C Tab.14, B.236 R.S 119-121 Tab.14, B.238 R.S 188-189.5 ° C Tab.14, B.241 R.S 137.5-139ßC Tab.14, B.248 R.S 144-144.5 ° C; 483 (M + 1) + Tab.14, B.251 R.S 125-126.5 ° C; 498 (+1) + Tab.14, B.253 R.S 163-164-C Tab.14, B.256 R.S 464 (+1) + Tab.1, B.258 R.S 140-141.5 ° C; 465 (M + 1) + Tab.14, B.261 R.S 126-127 ° C; 480 (+1) + Tab.14, B.263 R.S 149.5-151 ° C Tab.14, B.266 RS 458 (M + 1) + Tab.14, B.268 RS 174-176 ° C Tab.14, B.271 RS 476 (M-1) - Tab.14, B.273 RS 123-125-C Tab.14, B.276 RS 11 -118-C; 456 (M + 1) + Tab.14, B.278 R.S 120.5-122 ° C Tab.14, B.281 R.S 155-157-C Tab.14, B.317 R.S 115.5-118.5 «C Tab.14, B.318 R.S 159.5- 60.5ßC Tab.14, B.319 R.S 136-137ßC Tab.14, B.320 R.S 142-143-C Tab.14, B.321 R.S 139-141 ° C Tab.14. B.322 R.S 125.5-126.5-C Tab.14. B.323 R.S 130.5-135.5 ° C Tab.14, B.324 R.S 112.5-113.5 ° C Tab.14, B.325 R.S 434 (M-1) - Tab.14, B.326 R.S 433 (M-1) - Tab.14, B.327 R.S 116-1 7-C Tab.14, B.328 R.S 488 (M-1) - Tab.14, B.329 R.S 487 (-1) - Tab.14, B.330 R.S 83-85-C Tab.14, B.331 R, S 132.5-134-C Tab.14, B.332 R.S 134-136-C Tab.14, B.333 R.S 141-142-C Tab.14. B.334 R.S 139-141 -C Tab.14, B.335 R.S 122-123-C Tab.14, B.336 R.S oil Tab.14. B.337 R.S 115-117-C Tab.14, B.338 R.S 108-110-C Tab.14, B.339 R, S 425 (M + 1) + Tab.14, B.340 R.S 427 (M + 1) + Tab.14, B.341 R.S 471 (+1) + Tab.14, B.342 R.S 127.5-129.5-C Tab.14, B.343 R.S 152.5-154.5-C Tab.14, B.344 R.S 166-167'C Tab.14, B.345 R.S 437 (+1) + Tab.14, B.346 R.S 437 (M + 1) + Tab.14, B.347 R.S 441 (+1) + Tab.14. B.348 R.S 443 (M + 1) + Tab.14, B.349 R.S 451 (W + 1) + Tab.14, B.351 R.S 467 (M + 1) + Tab.14, B.352 R.S 476 (M + 1) + Tab.14, B.353 R.S 486 (M + 1) + Tab.1, B.354 R.S 491 (M + 1) + Tab.14, B.355 R.S 492 (M + 1) + Tab.14, B.359 R.S 411 (+1) + Tab.14, B.360 R, S 441 (M + 1) + Tab.14, B.361 R.S 452 (M + 1) + Tab.14, B.362 R.S 467 ((? T1) + Tab.14, B.363 R.S 476 (M + 1K Tab.14, B.364 R.S 426 (M + 1) + Tab.14, B.365 R.S 440 (+1 > + Tab.14, B.366 R.S 442 (+1) + Tab.14, B.367 R.S 452 (M + 1 > + Tab.14, B.368 R.S 452 (M + 1) + Tab.14, B.369 R.S 456 (+1 > + Tab.14, B.370 R.S 459 (M + 1) + Tab.14, B.371 R.S 466 (M + 1) + Tab.14, B.372 R.S 467 (M + 1) + Tab.14, B.373 R.S 482 (M + 1) + Tab.14, B.374 R.S 482 (+1) + Tab.14, B.375 R.S 491 (M + 1K Tab.14, B.378 R.S 506 (M + 1) + Tab.14. B.379 R.S 507 (M + 1) + Tab.14, B.380 R.S 549 (M + 1) + Tab.15, B.3 R.S 147-148-C Tab.15, B.73 R.S 121-122-C Tab.15, B.85 R.S 147-150'C Tab.15, B.91 R, S 156-158-0 Tab.15, B.97 R.S 160-165-C Tab.15, B.103 R, S 141-143-C Tab.16, B.3 R, S 140-145-C Tab.16, B.91 R.S 463 (M + 1 > + Tab.16, B.193 R.S 437 (nA + 1.}. + Tab.16, B.248 R, S 509 (M + 1) + Tab.16, B.258 R.S 491 (M + 1) + Tab.16, B.273 R.S 467 (M + 1) + fab.16. B.278 R.S 502 (M + 1) + Tab.16, B.334 R.S 158-159-C Tab.16, B.339 R.S 451 (+1) + Tab.16, B.340 R.S 453 (M + 1) + Tab.16, B.345 R, S 463 (M + 1) + Tab.16, B.346 R, S 463 (M + 1) + Tab.16, B.347 R.S 467 (M + 1) + Tab.16, B.348 R, S 469 (M + 1) + Tab.16, B.349 R.S 478 (M + 1) + Tab.16, B.350 R.S 490 (+1) + Tab.16, B.351 R, S 493 (+1) + Tab.16, B.352 R.S 502 (M + 1) + Tab.16, B.353 R.S 512 (M + 1) + Tab.16, B.354 R.S 517 (M + 1) + Tab.16, B.355 R.S 518 (M + 1) + Tab.16, B.356 R.S 521 (M + 1) + Tab.16, B.357 R.S 535 (+1) + Tab.16, B.358 R.S 560 (M + 1) + Tab.16, B.362 R, S 493 (M + 1) + Tab.17, B.1 R oil Tab.17, 8.3 R, S 123-128-C Tab.17, B.3 R 126-127 Tab.17, B.3 S oil Tab.17, B.11 R oil Tab.17, B.79 R.S 144-145-C Tab.1, B.82 R.S 115.5-117.5-C Tab.17, B.85 R.S 139.5-140.5'C Tab.17, B.88 R.S 96-97.5-C Tab.17, B.91 R.S 461 (M + 1) + Tab.17, B.94 R.S 476 (M + 1) + Tab.17, B.248 R.S 507 (M + 1) + Tab.17, B.251 R.S 520 (M-1) -; 522 (+1) + Tab.17, B.258 R.S 489 (M + 1) + Tab.17, B.261 R.S 504 (+1) + Tab.17, B.273 R.S 480 (+1) + Tab.17, B.334 R.S 135-137-C Tab.17, B.339 R.S 449 (M + 1) + Tab.17, B.340 R.S 451 (+1) + Tab.17, B.345 R.S 461 (M + 1) + Tab.17, B.346 R.S 461 (M + 1) + Tab.17, B.347 R.S 465 (+1) + Tab.17, B.348 R.S 467 (+1) + Tab.17, B.349 R.S 475 (M + 1) + Tab.17, B.350 R.S 488 (M + 1) + Tab.17, B.351 R.S 491 (+1) + Tab.17, B.352 R.S 500 (+1) + Tab.17, B.353 R.S 510 (+1) + Tab.17, B.354 R.S 515 (+1) + Tab.17, B.355 R.S 516 (+1) + Tab.17, B.356 R.S 519 (M + 1) + Tab.17, B.358 R, S 558 (M + 1) + Tab.17, B.359 R.S 435 (+1) + Tab.17, B.360 R.S 465 (+1) + Tab.17, B.361 R.S 476 (M + 1) + Tab.17, B.362 R.S 491 (M + 1) + Tab.17, B.363 R.S 500 (M + 1) + Tab.17, B.364 R.S 450 (+1) + Tab.17, B.365 R.S 464 (+1) + Tab.17, B.366 R.S 466 (+1) + Tab.17, B.367 R.S 476 (M + 1) + Tab.17, B.368 R.S 476 (M + 1) + Tab.1, B.369 R.S 480 (M + 1) + Tab.1, B.370 R.S 482 (+1) + Tab.17, B.371 R.S 490 (+1) + Tab.17. B.372 R.S 491 (M + 1) + Tab.17. B.373 R.S 506 (+1) + Tab.17, B.374 R.S 506 (M + 1) + Tab.17, B.375 R.S 515 (M + 1) + Tab.17. B.376 R.S 515 (M + 1) + Tab.17. B.377 R.S 525 (M + 1) + Tab.17, B.378 RS 530 (M + 1) + Tab.17, B.379 RS 531 (M + 1) + Tab.17, B.380 RS 573 (M + 1) + Tab.18, B .3 diastrere? A A 477 (-1) - (rae.) Tab.18, B.3 diastereomer B 477 (M-1) - (rae.) Tab.18, B.38 RS 130-132-C Tab .18, B.85 RS 141.5-143.5 ° C / 459 (M + 1) + Tab.18, B.88 R.S. 110.5-113.5 ° C / 474 (M + 1) + Tab.18, B.319 RS 161-163-C Tab.20, B.3 RS 140-143-C Tab.21, B.3 RS 121-123-C Tab.21, B.88 RS 119.5-121.5 ° C Tab.21, B.91 RS 489 (M + 1) + Tab.21, B.94 RS 504 (M + 1) + Tab.21, B, 258 RS 517 (M + 1) + Tab.21 , B, 261 RS 532 (M + 1) + Tab.21, B.319 RS 110-112-C Tab.21, B.334 RS 127-128-C Tab.21, B.339 RS 477 (M + 1) + Tab.21, B.340 RS 479 (+1) + Tab.21, B.345 RS 489 (M + 1) + Tab.21, B.347 RS 494 (M + 1) + Tab.21 , B.348 RS 495 (M + 1) + Tab.21, B.349 RS 503 (M + 1) + Tab.21, B.351 RS 519 (+1) + Tab.21, B.352 RS 528 (+1) + Tab.21, B.353 RS 538 (M + 1) + Tab.21, B.354 RS 543 (M + 1) + Tab.21, B.355 RS 54 (M + 1) + Tab.21, B.356 RS 547 (M + 1) + Tab.21, B.358 RS 586 (M + 1) + Tab.21, B.359 R.S 463 (M + 1) + Tab.21, B.361 R, S 504 (M + 1) + Tab.21, B.362 R.S 519 (M + 1) + Tab.21, B.363 R.S 528 (M + 1) + Tab.21, B, 364 R.S 478 (M + 1) + Tab.21, B.365 R.S 492 (M + 1) + Tab.21.B.366 R.S 494 (+1) + Tab.21, B.367 R.S 504 (M + 1) + Tab.21, B.368 R.S 504 (M + 1) + Tab.21, B.369 R.S 509 (+1) + Tab.21, B.370 R.S 510 (M + 1) + Tab.21, B.371 R.S 518 (+1) + Tab.21, B.372 R.S 519 (+1) + Tab.21, B, 373 R.S 534 (M + 1) + Tab.21, B.374 R.S 534 (M + 1) + Tab.21, B.376 R.S 543 (M + 1) + Tab.21, B.377 R.S 553 (M + 1) + Tab.21, B.378 R.S 558 (+1) + Tab.21, B.379 R.S 559 (M + 1) + Tab.21, B.381 R.S 562 (+1) + Tab.24, B.3 R.S 119-127-C Tab.25, B.3 R.S 143-149'C Tab.27, B.3 diastereomer A 587 (M-1) - (rae.) Tab.27, B.3 diastereomer B 587 (-1) - (rae.) Tab.30, B.3 R.S oil Tab.30, B.334 R.S 135-137-C Tab.32, B.3 R.S 142-144-C Tab.32, B.334 R.S 156-157-C Tab.36, B.3 R.S 171-178-C Tab.40, B.3 R.S 151-158-C Tab.47, B.3 R.S 145-147-C Tab.48, B.3 RS 156-158-C Tab.49, B.3 RS 144-148-C Tab.50, B.3 RS 123-126-C (M (ESMS) = ionic peaks in the spectrometry of electrospray masses Table D (Ugi Intermediaries) (Me means methyl) No. R2 R3 Physical Data p. f.
D1 H 4-CI, 3-F-phenyl -CH2Cp2- 3,4-di-Me? -phenyl oil D2 H 4-CI, 3-CF3-phenyl -CH CH2- 3,4-di-Me? -phenyl oil D3 H 4-CI, 3-Ff enyl -CH2Cp2 * 4-n-butyl ?, 3-Me? -94-97 phenyl D4 H 3,4-di-CI-phenyl -CH2CH-3,4-di-M ?? - phenyl oil D5 H 4-Br-phenyl -Cri2CH2- 3,4-di-Me? -phenyl oil D6 H -? - enyl -Cri 2 CH - 3,4-di-M ?? -phenyl 95-97 D7 H 4-CF3? -phenyl -CH2CH2- 3,4-di-Me? -phenyl oil D8 H 3,4-di-M? - f enyl -CH2Cp2- 3,4-di-Mß? -f enyl oil D9 H 4-N (M?)? -f-enyl -CH ^ H ^ 3,4-di-Me? -phenyl oil D10 H 4-MeS-f enyl -CH2CH2- 3,4-di- M -ifenyl 71-75 D11 H 3-Me-phenyl -CH2CH2- 3,4-dl-M ?? -fyl enyl oil D12 H 3-CFrphenyl -Cp2Cp2- 3,4-dl-M ?? -phenyl oil D13 H 4-Ph? -phenyl -Cp2Cp2- 3,4-di-M? -phenyl oil D14 H 4-Et? -phenyl -C p2CH2- 3,4-dl-M? -phenyl 100-102 D15 H 3.4 - (? CH2?) - phenyl 3,4-di-e? -phenyl oil D16 H 4-Ph-phenyl -CH2CH2- 3,4-di-Me? -phenyl oil D17 H 4-α-propyl-phenyl -CH 2 CH 2 -3,4-di-M ??-phenyl 87-91 D18 H 4- (C ???) - phenyl -C p 2 CH 3 * 3,4-d¡-M ??-phenyl 99-101 D19 H 3,4-di-F-phenyl-CH2CH2- 3,4-di-M? - f enyl oil D20 H 4 -butyl-phenyl -CH2CH2- 3,4-di-Me? -fenyl 83-87 D21 H 4-CN-phenyl "CH2CH2" 3,4-di-M? -f enyl oil D22 H 3-CI-phenyl "CH CH2" 3,4-di-Mß? -phenyl oil D23 H 1 - naphthyl ~ CH2C i2 ~ 3,4-di-Me? -phenyl oil D24 H 3,5-di-CI-phenyl • Cr ^ Cr ^ * 3,4-di-Me? -phenyl oil D25 H 2- thienyl "CH2CH2" 3,4-dl-Me? -phenyl oil D26 H 4-CI- phenyl "CH2CH2" 3-Me?, 4- propargyl-O- phenyl oil D27 H 2- furanyl ~ Cri CH2 * 3,4-di-Me? -f enyl oil D28 H 4-Ph-f enyl "CH2CH2" 3-Mß?, 4- propargi o- phenyl oil D29 H 4-CI-phenyl -CH (CH3) CH2- oil D30 H 4-Br-phenyl ~ CH2Cri "3-Me ?, 4- propargyl-O- phenyl oil D31 H 4-Me-phenyl -CH CH2" 3-M ??, 4- propargyl-O- phenyl oil D32 H 4-Br-phenyl "CH CH2" 3-Me?, 4- (pent-2'-n-1 '- iloxy oil) -phenyl D33 H 4-Me-phenyl -CH2CH2-S-MeO ^ -Ipent- ^ -in-V- oil loxi) -phenyl 'D34 H 2- naphthyl -CH2CH2- 3,4-di-M ?? -phenyl oil D35 H 3,4-di-CI-phenyl -CH 2 CH 2 -3-M ??, 4-propargyl-ω-phenyl oil D36 H 4-M?-F-enyl -CH (CH 3) CH 2 - 3 -Me?, 4 - propargyl-O- phenyl oil D37 H 5 -Me, 2- furanyl -CH2CH2-3-, 4-allyl-phenyl-oil D38 H 3-F-phenyl -CH2CH2"3-M ??, 4-allyl? -phenyl oil D39 H 5-Mß, 2-thienyl-CH CH 2 * 3-M, 4-allyl-0-fepyl oil D40 H 4-M? -phenyl -CH2CH2"3-M??, 4-allyl? -phenyl oil 041 H 2-M ?? - phenyl -CH2CH2- 3 -Me?, 4-allyl-0-phenyl oil D42 H 3-CI-phenyl-CH2CHJ-3-Mß?, 4-allyl-phenyl-oil D43 H 2-CI-phenyl -CH2CHr 3 -Me?, 4-allyl-phenyl-oil D44 H 3,5-di-F-phenyl -CH2CH 3-M ??, 4-allyl-0-phenyl oil 045 H 3-Me, 4-Me? -phenyl -CH2CH2- 3-Me?, 4-? Allyl-O-phenyl oil D46H 4-N-acetylamino-f-enyl -Cp2CH2- 3 -Me?, 4- allyl-O-phenyl oil D47 H 4- (C00M?) - phenyl -CH2CH2- 3 -Me?, 4- allyl-O-phenyl oil D48 H 3,5-di-Me? -f enyl -CH2CH2-3-Me?, 4- allyl-O-phenyl oil D49 H 2,4-di-MeO-phenyl -CH2CH2-3-Me?, 4- allyl-O-phenyl oil D50 H 2,4-di-CI-phenyl -CH2CH2- 3 -Me?, 4- allyl-O-phenyl oil D51 H 3- (N-? Irrolidlna) -phenyl -CH2CH2- 3 -Me?, 4- allyl-O-phenyl oil D52 H 4-Ph-phenyl -CH2CH2-3-Me?, 4- allyl-O-phenyl oil D53 H 3-Br-f enyl -CH2CH2-3-Me?, 4- allyl-O-phenyl oil D54 H 3 -Me?, 4- propargyl-O- -CH2Cp2 * 3-Me?, 4- allyl-O-phenyl phenyl oil D55 H 3 -Br, 2-thienyl -CH2Cp2-3-Me?, 4- allyl -O-phenyl oil D56 H 3-fluorenyl -CH2CH2-3-Me?, 4-allyl-0-phenol D57 H 3- (4'-CI-PhO) -phenyl -CH2CH2-3-MeO, 4- allyl-O-phenyl oil D58 H 5-Me, 2-f-uranyl-CH2CH2-3-Mβ ?, 4- propargyl-O-phenyl oil D59 H 3 -F-phenyl -CHCH 2 -3-Me?, 4- propargyl-O-phenyl oil D60 H 5-M ?, 2-thienyl-CH 2 CH 2 -3-Me ?, 4-propargyl-O-phenyl oil D61 H 4-Me? -phenyl -CH 2 CH 2 -3-M ?, 4- propargyl-O-oil phenyl D62 H 2 -Me? -phenyl -CH2Cp2-3Mβ ?, 4- propargyl-O- phenyl oil D63 H 3-M ??-phenyl 3- e?, 4- propargyl-O- phenyl oil D64 H 3 -CI-phenyl -CH2CH2- 3-M ??, 4- propargyl-O-phenyl D65 2-CI-phenyl -CH2CH2- 3-??, 4- propargyl-O- fepyl oil D66 H 3.5-dl-F- phenyl -CH2CH2- 3 -Me?, 4- propargyl-O- phenyl oil D67 H 3-Mß, 4-Me? -phenyl -CH 2 CHr 3- e?, 4-propargyl -? - phenyl oil D68 H 4 -N02-phenyl -CH 2 CH 2 -3-Me?, 4- propargyl-O-phenyl oil D69H 4-N-acetylamino-phenyl-CH2CH2-3M, 4- propargyl-O-phenyl oil. D70 H 4- (C00M?) - phenyl -CH 2 CHr 3- e?, 4-propargyl -? - phenyl oil D71 H 3,5-di-Me? -phenyl -CH2CH2- 3-M ??, 4-propargyl- ? - phenyl oil D72 H 2,4-dl-CI-phenyl -CHjCHr 3-Me?, 4-propargyl-0- phenyl oil D73 H 4- (N-pyrrolidino) -fepyl -CH 2 CHr 3-M ?? , 4- propargyl-O- phenyl oil D74 H 3 -Br-phenyl -CH2CH2-3-e?, 4-propargyl -? - phenyl oil D75 H 3-M? O, 4- propargyl-0- -CH2CH2- 3 -Me?, 4-propargyl-0- phenyl phenyl oil D76 H 4-Br, 2-thienyl -CH 2 CH 2 -3? O, 4- propargyl-O- phenyl oil D77 H 3-fluorenyl -CH 2 CH 2 -3-Me? , 4-propargyl-0- phenyl oil D78 H 4- (4'-CI-Ph?) - phenyl -CH ^ Hr 3-M ??, 4- propargyl-O- phenyl oil D79 H 2,4-di-? Me? -phenyl -CHjCHr 3-M ?, 4- propargyl-O- phenyl oil D80 H 5 -Me, 2- furanyl -CH2CH2-3M, 4- (pent-2'-ln-1 ' - iloxy oil) -phenyl D81 H 3 -F- phenyl -CH 2 CH 2 -3-Mβ?, 4- (pent-2'-in-1'- iloxy) -phenyl oil 'D82 H 5-Mß, 2-thienyl- CH2CHj- 3-Me?, 4- (pent-2'-in-1'- iloxy oil) -phenyl D83H 4-MTO-phenyl -CH2CH2 * 3-M ??, 4- (pent-2'-in-1'-yloxy-oil) -phenyl D84 H 2 -MeO-phenyl -CH2CH2- S- eO ^ -Pen ^ '- in-V- iloxy oil) -phenyl D85 H 3 -MeO-phenyl -CH 2 CH 2 -3-Me?, 4- (p? nt-2'-in-V-yloxy) -phenyl ester D86 H 2- CI-phenyl -CH2CH2-3M, 4- (p? Nt-2'-in-1'-yloxy-oil) -phenyl D87 H 3,5-di-F-phenyl * Cr? 2Cp2- 3- Me, 4- (pent-2'-ln-1'- iloxy-oil) -phenyl D88 H 3 -Me, 4-MeO-phenyl -CH 2 CH 2 -3 -M, 4- (pent-2'-in -1'- iloxy oil) -phenyl D89 H 4 -N02-phenyl -CH 2 CH 2 * 3 -M, 4- (p? Nt-2'-in-1'- iloxy oil) -fepyl D90 H 4- ( COOM?) - phenyl -CH 2 CHr 3 -Me?, 4- (pent-2'-in-1 * - iloxy oil) -phenyl D91 H 3,5-di-MeO-phenyl -CH 2 CH 2 -3-Me?, 4 - (pent-2'-in-1'- iloxy oil) -phenyl D92 HG 2,4-di-M? O-phenyl -CH 2 CH 2 -3-Me?, 4- (pent-2'-in-1 ' - iloxy oil) -phenyl D93 H 2,4-di-CH-phenyl-Cp2CH2-3-Mβ, 4- (pßnt-2 'nV-iloxy oil) -phenyl D94 H 4- (N-pyrrolidino Henyl -CH ^ H 3 -Me?, 4- (p? Nt-2'-in-V-iloxy oil) -phenyl D95 H 3 -Br-phenyl -CH 2 CH 2 -3-Me?, 4- (p? Nt-2'-in- 1'- iloxi oil ) -phenyl D96 H 3-M? O, 4-propargyl-0- -CH 2 CH 2 -3-Me?, 4- (p? nt-2'-in-1'- phenyl iloxy) phenyl D97 H 4- Br, 2-thienyl-CH2CH2-3M, 4- (pent-2'-ln-1'-yloxy-oil) -phenyl D98 H 3 -fluorenyl -CH2CH2- 3-M ??, 4- (pent -2'-in-1'- iloxy oil) -phenyl D99 H 4- (4'-CI-PhO) -phenyl -CH 2 CH 2 -3-Me?, 4- (p? Nt-2'-in-1'-yloxy) -phenyl oil D100 H 5-M?, 2 -furanyl -CH CH2"3,4-dl-M ?? -phenyl oil D101 H 3-F- phenyl -CH2CH2- 3,4-di-Me? -phenyl oil D102 H 5-Me, 2-thienyl -CH2CH2"3,4 li-Me? -phenyl oil D103 H 4-MeO-phenyl 3,4-dl-M ?? -phenyl oil D104 H 2-M? O-phenyl -CH2CH2 * 3,4-dl-Me? -phenyl oil D105 H 3-MeO-phenyl -CH2CH2"3,4-di-Me? -phenyl oil D106 H 2-CI-phenyl -CH2CH "3,4-di-Me? -phenyl oil D107 H 3,5-di-F-f-enyl-CH2CH2"3,4-di-M? -phenyl oil D108 H 3-M ?, 4-MeO-phenyl "CH2CH2- 3,4-dl-M" -phenyl oil D109 H 4-N02-phenyl -CH CH2 * 3,4-di-Me? -phenyl oil D110 H 4- (N-acetylamino1) - -CH CH2"3,4-dl-Me? -phenyl phenyl oil D111 H 3,5-di-MeO-phenyl" GrfeCrfe * 3,4-dl-Me? -phenyl oil D112 H 2,4-di-MeO-phenyl ~ Cp2Cp2 * 3,4-dl-M ?? - phenyl oil D113 H 2,4-di-CI-phenyl * Cp2Cp2"3,4-di-MeO-phenyl oil D114 H 4- (N-pyrrolidino) -phenol -CH2CH2- 3,4-dl-MeO-phenyl oil D115 H 3-Br-phenyl -CH2CH * 3,4-dl-M? O-phenyl oil D116 H 3 -MeO, 4-proparg? L 0- -CH2CH2"3,4-dl-M? O-phenell phenyl oil D117 H 4-Br, 2-thienyl -CH2CH2- 3,4-di-Me? phenyl oil D118 H 3-fluorenyl -CH2CH2"S ^ -di-M? O-'phenyl oil D119 H 4- (4'-CI-Ph?) - phenyl -CH2CH2"3,4-dl-M ?? -phenyl oil Examples of Formulation for the compounds of formula I The working procedures for the preparation of formulations of the compounds of the formula I, such as emulsifiable concentrates, solutions, granulates, dry powders, and wettable powders, are described in the Publication International Number WO 97/33890.
Biological Examples B.-l: Action against Plasmopara viticola on vines a) Residual protective action Vine seedlings are sprayed at the 4 to 5 leaf stage with a spray mixture (0.02 percent active ingredient) prepared from a Wettable powder formulation of the test compound. After 24 hours, the treated plants are infected with a sporangia suspension of the fungus. The infestation of the fungus is evaluated after incubation for 6 days, with 95 to 100 percent relative humidity and at 20 ° C. b) Residual healing action Vine seedlings are infected in the 4- to 5-leaf stage with a sporangia suspension of the fungus. After incubation for 24 hours in a humidity chamber, with 95 to 100 percent relative humidity and at 20 ° C, the infected plants are dried and sprayed with a spray mixture (0.02). percent active ingredient) prepared from a wettable powder formulation of the test compound. After the spray coating is dried, the treated plants are placed in the humidity chamber again. The fungus infestation is evaluated 6 days after infection. The compounds of Tables 1 to 50 exhibit a very good fungicidal action against Plasmopara vi ticola in vines. The compounds Tab.14, B.203; Tab.14, B.319; Tab.14, B.335 Tab.14, B.336; Tab.15, B.3; Tab.17, B.l; Tab.17, B.3; Tab.17, B.82 Tab.17, B.88; Tab.17, B.251; Tab.21, B.3; Tab.21, B.88 Tab.21, B.319; Tab.24, B.3 and others, inhibit in a virtually complete manner the fungal infestation (infestation from 0 to 10 percent) in this test. On the other hand, infestation with Plasmopara in untreated and infected control plants is 100 percent.
B-2: Action against Phytophthora in tomato plants a) Residual protective action After a cultivation period of 3 weeks, the tomato plants are sprayed with a spray mixture (0.02 percent active ingredient) prepared from a Wettable powder formulation of the test compound. After 48 hours, the treated plants are infected with a sporangia suspension of the fungus. The infestation of the fungus is evaluated after incubation of the infected plants for 4 hours. days, with 90 to 100 percent relative humidity and at 20 ° C. b) Systemic action After a cultivation period of 3 weeks, the tomato plants are watered with a spray mixture (0.02 percent active ingredient, based on the volume of the soil) prepared from a wettable powder formulation of the test compound. Care is taken that the spray mixture does not come in contact with the parts of the plants that are above the ground. After days, the treated plants are infected with a sporangia suspension of the fungus. The infestation of the fungus is evaluated after incubation of the infected plants for 4 days with 90 to 100 percent relative humidity, and at 20 ° C. The compounds of Tables 1 to 50 exhibit a lasting effect (less than 20 percent of fungus infestation). The infestation is prevented in a virtually complete manner (infestation from 0 to 5 percent) with the compounds Tab.14, B.112; Tab.14, B.203; Tab.14, B.335; Tab.14, B.336 Tab.15, B.3; Tab.17, B.l; Tab.17, B.3; Tab.17, B.82, Tab.17, B.85 Tab.17, B.88; Tab.17, B.251; Tab.18, B.3; Tab.21, B.3; Tab.21, B.88 Tab.21, B.319 and others. On the other hand, infestation with Phytophthora in untreated and infected control plants is 100 percent.
B-3: Action against Phytophthora in potato plants a) Residual protective action Potato plants from 2 to 3 weeks of age (Bintje variety) are sprayed with a spray mixture (0.02 percent active ingredient) prepared from a wettable powder formulation of the test compound. After 48 hours, the treated plants are infected with a sporangia suspension of the fungus. The infestation of the fungus is evaluated after incubation of the infected plants for 4 days with 90 to 100 percent relative humidity and at 20 ° C. b) Systemic action Potato plants from 2 to 3 weeks of age (Bintje variety) are watered with a spray mixture (0.02 percent active ingredient, based on the volume of the soil) prepared from a powder formulation Wettable of the test compound. Care is taken that the spray mixture does not come in contact with the parts of the plants above the ground. After 48 hours, the treated plants are infected with a sporangia suspension of the fungus. The infestation of the fungus is evaluated after incubation of the infected plants for days with 90 to 100 percent relative humidity and at 20CC. The compounds of Tables 1 to 50 exhibit a lasting effect (less than 20 percent of fungus infestation). The infestation is prevented in a virtually complete manner (infestation from 0 to 5 percent) with compounds Tab.14, B.38; Tab.14, B.203; Tab.14, B.319; Tab.15, B.3; Tab.17, B.l; Tab.17, B.3; Tab.17, B.82; Tab.17, B.85; Tab.17, B.88; Tab.17, B.251 and other. On the other hand, infestation with Phytophthora in untreated and infected control plants is 100 percent.

Claims (12)

1. A compound of the formula I: wherein n is the number zero or uncRi is optionally substituted alkyl, alkenyl, alkynyl, cycloalkyl, cycloalkylalkyl, aryl or arylalkyl; or a group NRaRb 'wherein Ra and b are each independently of the other, hydrogen, alkyl, or together form a. alkylene bridge; R2 is hydrogen or alkyl; R3 is optionally substituted aryl or heteroaryl; A is alkylene; and B is optionally substituted aryl; with the exception of the following compounds: 2-phenyl-N- (1-phenyl-et? l) -2- (4-methylphenyl) -sulfonylamino-acetamide, 2-phenyl-N- (1-phenyl-ethyl) - 2- (4-chlorophenyl) -sulfonylamino-acetamide, 2-phenyl-N- (1-phenyl-et? L) -2- (4-nitrophenyl) -sulfonylamino-acetamide. 2-phenolN- (l-phenyl-et? L) -2- (4-methoxyphenyl) -sulfonylamino-acetamide, 2-phenolN- (1-phenol-et? L) -2- (4-fluorofeml) -sulfonilam-acetamide, 2-phenolN- (1-phenol-et? L) -2-phen? L-sulfon? Lam? No-acetamide, and 2-phenyl-N- ( 1-phenyl-ethyl) -2-methane-sulfonamino-acetamide.
2. A compound of the formula I according to claim 1, wherein: n is the number zero or 1; Ri is alkyl of 1 to 10 carbon atoms, alkene of 2 to 10 carbon atoms, alkynyl of 2 to 10 carbon atoms, cycloalkyl of 3 to 8 carbon atoms, cycloalkyl of 3 to 8 carbon atoms-alkyl of 1 to 6 carbon atoms, aryl of 6 to 10 carbon atoms, or aryl of 6 to 10 carbon atoms-alkyl of 1 to 6 carbon atoms which are optionally mono- or poly-substituted by alkyl of 1 to 8 carbon atoms carbon, alkoxy of 1 to 8 carbon atoms, thioalkyl of 1 to 8 carbon atoms, alkylsulfonyl of 1 to 8 carbon atoms, cycloalkyl of 3 to 8 carbon atoms, alkoxycarbonyl of 1 to 8 carbon atoms, alkenyloxy carbonyl of 3 to 8 carbon atoms, alkynyloxycarbomide of 3 to 8 carbon atoms, cycloalkyl of 3 to 8 carbon atoms-alkyl of 1 to 6 carbon atoms, alkenyl of 2 to 8 carbon atoms, alkynyl of 2 to 8 carbon atoms, alkenyloxy of 3 to 8 carbon atoms, alkynyloxy of 3 to 8 carbon atoms, alkanoyl of 1 to 8 carbon atoms (wherein all these groups containing alkyl, alkenyl, alkynyl, or cycloalkyl, may be partially or completely halogenated), halogen, cyano, or nitro; or a group NRaRb, wherein Ra and Rb are each independently of the other, hydrogen, alkyl of 1 to 8 carbon atoms, or are together alkylene of 2 to 7 carbon atoms; R2 is hydrogen or alkyl of 1 to 8 carbon atoms; R3 is phenyl, naphthyl, or heteroaryl formed by 1 or 2 5 or 6 membered rings containing from 1 to 4 identical or different heteroatoms selected from oxygen, nitrogen, or sulfur, and are optionally mono- or poly-substituted by alkyl of 1 to 8 carbon atoms, alkenyl of 2 to 8 carbon atoms, alkynyl of 2 to 8 carbon atoms, alkoxy of 1 to 8 carbon atoms, thioalkyl of 1 to 8 carbon atoms, alkylsulfonyl of 1 to 8 carbon atoms, cycloalkyl of 3 to 8 carbon atoms, cycloalkyl of 3 to 8 carbon atoms-alkyl of 1 to 6 carbon atoms, alkylenedioxy of 1 to 4 carbon atoms, alkoxycarbonyl of 1 to 8 carbon atoms, alkenyloxycarbonyl of 3 to 8 carbon atoms, alkynyloxycarbonyl of 3 to 8 carbon atoms, cycloalkyloxy of 3 to 8 carbon atoms, alkenyloxy of 3 to 8 carbon atoms, alkynyloxy of 3 to 8 carbon atoms, alkanoyl of 1 to 8 carbon atoms, dialkylamino of 1 to 8 carbon atoms, alkylamino of 1 to 8 carbon atoms (wherein all these groups containing alkyl , alkenyl, alkynyl, or cycloalkyl can be partially or completely halogenated), halogen, nitro, cyano, hydroxyl, or amino; A is alkylene of 1 to 8 carbon atoms; and B is phenyl optionally mono- or poly-substituted by alkyl of 1 to 8 carbon atoms, alkenyl of 2 to 8 carbon atoms, alkynyl of 2 to 8 carbon atoms, alkoxy of 1 to 8 carbon atoms, thioalkyl of 1 to 8 carbon atoms, alkylsulfonyl of 1 to 8 carbon atoms, cycloalkyl of 3 to 8 carbon atoms, cycloalkyl of 3 to 8 carbon atoms-alkyl of 1 to 6 carbon atoms, alkoxycarbonyl of 1 to 8 carbon atoms, alkenyloxycarbonyl of 3 to 8 carbon atoms, alkynyloxycarbonyl of 3 to 8 carbon atoms, cycloalkyloxy of 3 to 8 carbon atoms, alkenyloxy of 3 to 8 carbon atoms, alkynyloxy of 3 to 8 carbon atoms, alkanoyl of 1 to 8 carbon atoms, dialkylamino of 1 to 8 carbon atoms, alkylamino of 1 to 8 carbon atoms, aryloxy of 6 to 10 carbon atoms, aryl of 6 to 10 carbon atoms-alkoxy of 1 to 6 carbon atoms, aryl of 6 to 10 carbon-alkenyloxy atoms of 1 to 6 carbon atoms, aryl of 6 to 10 carbon atoms-alkynyloxy of 1 to 6 carbon atoms, alkanoyloxy of 1 to 8 carbon atoms (where all these groups containing alkyl, alkenyl, alkynyl, or cycloalkyl may be partially or completely halogenated, and wherein all the aryl-containing groups may be optionally mono- or poly-substituted by alkyl of 1 to 8 carbon atoms, alkenyl from 2 to 8 carbon atoms, cycloalkyl of 3 to 8 carbon atoms, alkoxy of 1 to 8 carbon atoms, thioalkyl of 1 to 8 carbon atoms, alkoxycarbonyl of 1 to 8 carbon atoms, haloalkyl of 1 to 8 atoms of carbon, haloalkoxy of 1 to 8 carbon atoms, halotioalkyl of 1 to 8 carbon atoms, halogen, nitro, or cyano), halogen, nitro, cyano, hydroxyl, amino, or the phenyl group may be substituted in two adjacent positions by alkylenedioxyl of 1 to 4 carbon atoms, wherein the alkylene part may be substituted by halogen.
3. A compound of the formula I according to claim 2, wherein: n is the number zero or one; Ri is alkyl of 1 to 10 carbon atoms, alkenyl of 2 to 10 carbon atoms, cycloalkyl of 3 to 8 carbon atoms which are optionally mono- or poly-substituted by alkyl of 1 to 8 carbon atoms, alkoxy of 1 to 8 carbon atoms, thioalkyl of 1 to 8 carbon atoms, alkanoyl of 1 to 8 carbon atoms, alkoxycarbonyl of 1 to 8 carbon atoms, haloalkyl of 1 to 8 carbon atoms, haloalkoxy of 1 to 8 carbon atoms , halotioalkyl of 1 to 8 carbon atoms, halogen, nitro, or cyano; or a group NRaRb 'wherein Ra and Rb are each independently of the other, hydrogen, alkyl of 1 to 8 carbon atoms, or are together tetramethylene or pentamethylene; R2 is hydrogen or methyl; R3 is phenyl, naphthyl, furyl, thienyl, imidazolyl, thiazolyl, oxazolyl, pyridyl, pyrimidyl, benzothiophene, benzothiazolyl, quinolinyl, pyrazolyl, mdolyl, benzimidazolyl, or pyrrolyl, optionally substituted by 1 to 3 substituents selected from alkyl of 1 to 8 carbon atoms, alkenyl of 2 to 8 carbon atoms, cycloalkyl of 3 to 8 carbon atoms, alkoxy of 1 to 8 carbon atoms, thioalkyl of 1 to 8 carbon atoms, alkoxy carbonyl of 1 to 8 carbon atoms carbon, haloalkyl of 1 to 8 carbon atoms, haloalkoxy of 1 to 8 carbon atoms, halotioalkyl of 1 to 8 carbon atoms, halogen, hydroxyl, nitro, or cyano; A is alkylene of 1 to 4 carbon atoms; and B is phenyl optionally substituted by 1 to 3 substituents selected from alkyl of 1 to 8 carbon atoms, alkoxy of 1 to 8 carbon atoms, alkenyl loxyl of 3 to 8 carbon atoms, alkynyloxy of 3 to 8 carbon atoms carbon, phenylalkyloxy of 1 to 6 carbon atoms, phenylalkenyloxy of 3 to 6 carbon atoms, phenylalkyloxy of 3 to 6 carbon atoms, thioalkyl of 1 to 8 carbon atoms, alkoxycarbonyl of 1 to 8 carbon atoms, haloalkoxy of 1 to 8 carbon atoms, haloalkenyloxy of 3 to 8 carbon atoms, halogen, hydroxyl, nitro, or cyano (wherein all phenyl-containing groups may be optionally substituted by 1 to 3 substituents selected from alkyl of 1 to 8 carbon atoms, alkoxy of 1 to 8 carbon atoms, thioalkyl of 1 to 8 carbon atoms, haloalkyl of 1 to 8 carbon atoms, haloalkoxy of 1 to 8 carbon atoms, halotioalkyl of 1 to 8 carbon atoms carbon, halogen, or cyano).
4. A compound according to formula I according to claim 3, wherein: n is number one; Ri is alkyl of 1 to 6 carbon atoms, alkenyl of 2 to 10 carbon atoms, cycloalkyl of 5 to 6 carbon atoms, which are optionally mono- or poly-substituted by alkyl of 1 to 8 carbon atoms, alkoxy 1 to 8 carbon atoms, alkoxycarbonyl of 1 to 8 carbon atoms, haloalkyl of 1 to 8 carbon atoms, haloalkoxy of 1 to 8 carbon atoms, halogen, or cyano; or a group NRaRb, wherein Ra and Rb are each independently of the other, methyl or ethyl; R2 is hydrogen; R3 is phenyl optionally substituted by 1 to 3 substituents selected from alkyl of 1 to 8 carbon atoms, alkenyl of 2 to 8 carbon atoms, cycloalkyl of 3 to 8 carbon atoms, alkoxy of 1 to 8 carbon atoms. thioalkyl of 1 to 8 carbon atoms, alkoxycarbonyl of 1 to 8 carbon atoms, haloalkyl of 1 to 8 carbon atoms, haloalkoxy of 1 to 8 carbon atoms, halotioalkyl of 1 to 8 carbon atoms, halogen, hydroxyl, nitro , or cyano; A is ethylene; and B is phenyl optionally substituted by 2 to 3 substituents selected from alkyl of 1 to 8 carbon atoms, alkoxy of 1 to 8 carbon atoms, alkenyloxy of 3 to 8 carbon atoms, alkynyloxy of 3 to 8 carbon atoms , phenylalkyloxy of 1 to 6 carbon atoms, phenylalkenyloxy of 3 to 6 carbon atoms, phenylalkynyloxy of 3 to 6 carbon atoms, thioalkyl of 1 to 8 carbon atoms, alkoxycarbonyl of 1 to 8 carbon atoms, haloalkoxy of 1 to 8 carbon atoms, haloalkenyloxy of 3 to 8 carbon atoms, halogen, hydroxyl, nitro, or cyano (wherein all phenyl-containing groups may be optionally substituted by 1 to 3 substituents selected from alkyl of 1 to 8 atoms carbon, alkoxy of 1 to 8 carbon atoms, thioalkyl of 1 to 8 carbon atoms, haloalkyl of 1 to 8 carbon atoms, haloalkoxy of 1 to 8 carbon atoms, halotioalkyl of 1 to 8 carbon atoms, halogen, or cyan o).
5. A compound of formula I according to claim 4, wherein: n is number one; Ri is alkyl of 1 to 4 carbon atoms optionally mono- or poly-substituted by fluorine, chlorine, bromine, or dimethylamine; R2 is hydrogen; R is phenyl optionally substituted by 1 to 3 substituents selected from alkyl of 1 to 8 carbon atoms, alkenyl of 2 to 8 carbon atoms, cycloalkyl of 3 to 8 carbon atoms, alkoxy of 1 to 8 carbon atoms, thioalkyl of 1 to 8 carbon atoms, alkoxycarbonyl of 1 to 8 carbon atoms, haloalkyl of 1 to 8 carbon atoms, haloalkoxy of 1 to 8 carbon atoms, halotioalkyl of 1 to 8 carbon atoms, halogen, nitro, or cyano; A is ethylene; and B is a group: wherein: R8 is alkyl of 1 to 4 carbon atoms, and R9 is alkyl of 1 to 8 carbon atoms, alkenyl of 3 to 8 carbon atoms, alkynyl of 3 to 8 carbon atoms, phenylalkyl of 1 to 6 carbon atoms, phenylalkenyl of 3 to 6 carbon atoms, phenylalkyl of 3 to 6 carbon atoms, haloalkyl of 1 to 8 carbon atoms carbon, haloalkenyl of 3 to 8 carbon atoms (where the groups containing phenyl may be optionally substituted by 1 to 3 substituents selected from alkyl of 1 to 8 carbon atoms, alkoxy of 1 to 8 carbon atoms, thioalkyl of 1 to 8 carbon atoms, haloalkyl of 1 to 8 carbon atoms, haloalkoxy of 1 to 8 carbon atoms, halotioalkyl of 1 to 8 carbon atoms, halogen, or cyano).
6. A process for the preparation of a compound of the formula I according to claim 1, which comprises: a) reacting an amino acid of the formula II, or a carboxyl-activated derivative of an amino acid of the formula II: with an amine of the formula V: H2N A B (V); or b) reacting a sulfonyl halide or sulfinyl halide of the formula III: OR II R, -5-X II (Oln wherein X is halide, with an amino acid derivative of the formula VI: H, N- (VI) NH-A-B and optionally c) oxidizing a compound of the formula I, wherein n = 0, and wherein Ri, R2, R3, A and B have the meaning defined for the formula I, to obtain a compound of the formula I wherein n = 1.
7. A composition for controlling and preventing the infestation of plants by microorganisms, which comprises as active ingredient a compound of the formula I according to claim 1, together with a suitable vehicle.
8. A method for controlling and preventing the infestation of plants by microorganisms, which comprises applying a compound of the formula I as an active ingredient to the plant, to the parts of the plant, or to the nutrient medium of the plant.
9. A method according to claim 8, which comprises the treatment of the seeds.
10. The use of a compound of the formula I as a microbicide.
11. The intermediary of formula VI: wherein R2, R3, A and B are as defined in formula I.
12. A process for the preparation of a compound of formula VI according to claim 11, which comprises: d) hydrolyzing a compound of formula X: under acidic or basic conditions, at a temperature between 0 ° C and 100 ° C, wherein R 2, R 3, A and B have the meaning defined for formula I, and wherein R 10 is lower alkyl or hydrogen. SUMMARY Novel a-amino acid amides of the formula I: as well as the possible isomers and mixtures of isomers thereof, wherein the substituents are defined as follows: n is the number zero or one; Ri is optionally substituted alkyl, alkenyl, alkynyl, cycloalkyl, cycloalkylalkyl, aryl or arylalkyl; or a group NRaRb, wherein Ra and Rb are each independently of the other, hydrogen, alkyl, or together form an alkylene bridge; R2 is hydrogen or alkyl; R3 is optionally substituted aryl or heteroaryl; A is alkylene; and B is optionally substituted aryl; with the exception of the following compounds: 2-phenyl-N- (l-phenyl-ethyl) -2- (4-methylphenyl) -sulfonylamino-acetamide, 2-phenyl-N- (1-phenyl-ethyl) -2- (4-chlorophenyl) -sulfonylamino-acetamide, 2-phenyl-N- (1-phenyl-ethyl) -2- (4-nitrophenyl) - sulfonylamino-acetamide, 2-phenyl-N- (1-phenyl-ethyl) -2- (4-methoxyphenyl) -sulfonylamino-acetamide, 2-phenyl-N- (1-phenyl-ethyl) -2- (4-fluorophenyl) ) -sulfonylamino-acetamide, 2-phenyl-N- (1-phenyl-ethyl) -2-phenyl-sulfonylamino-acetamide, and 2-phenyl-N- (1-phenyl-ethyl) -2-methanesulfonylamino-acetamide . The novel compounds have protective properties of plants, and are suitable for protecting plants against infestations by phytopathogenic microorganisms, in particular fungi.
MXPA/A/2000/008383A 1998-02-27 2000-08-25 N-sulphonyl and n-sulphinyl phenylglycinamide___________________ MXPA00008383A (en)

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GB9804265.8 1998-02-27

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MXPA00008383A true MXPA00008383A (en) 2001-07-31

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