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  • C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
  • C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
  • C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
  • C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
  • C07D213/72—Nitrogen atoms
  • C07D213/74—Amino or imino radicals substituted by hydrocarbon or substituted hydrocarbon radicals
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  • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
  • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
  • A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
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  • C07D203/06—Heterocyclic compounds containing three-membered rings with one nitrogen atom as the only ring hetero atom not condensed with other rings having no double bonds between ring members or between ring members and non-ring members
  • C07D203/08—Heterocyclic compounds containing three-membered rings with one nitrogen atom as the only ring hetero atom not condensed with other rings having no double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to the ring nitrogen atom
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  • C07D217/00—Heterocyclic compounds containing isoquinoline or hydrogenated isoquinoline ring systems
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  • C07D217/04—Heterocyclic compounds containing isoquinoline or hydrogenated isoquinoline ring systems with only hydrogen atoms or radicals containing only carbon and hydrogen atoms, directly attached to carbon atoms of the nitrogen-containing ring; Alkylene-bis-isoquinolines with hydrocarbon or substituted hydrocarbon radicals attached to the ring nitrogen atom
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  • C07D231/00—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings
  • C07D231/02—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings
  • C07D231/10—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
  • C07D231/12—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
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  • C07D233/04—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member
  • C07D233/06—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member with only hydrogen atoms or radicals containing only hydrogen and carbon atoms, directly attached to ring carbon atoms
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  • C07D233/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings
  • C07D233/04—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member
  • C07D233/06—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member with only hydrogen atoms or radicals containing only hydrogen and carbon atoms, directly attached to ring carbon atoms
  • C07D233/08—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member with only hydrogen atoms or radicals containing only hydrogen and carbon atoms, directly attached to ring carbon atoms with alkyl radicals, containing more than four carbon atoms, directly attached to ring carbon atoms
  • C07D233/12—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member with only hydrogen atoms or radicals containing only hydrogen and carbon atoms, directly attached to ring carbon atoms with alkyl radicals, containing more than four carbon atoms, directly attached to ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms
  • C07D233/16—Radicals substituted by nitrogen atoms
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  • C07D233/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings
  • C07D233/54—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members
  • C07D233/56—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members with only hydrogen atoms or radicals containing only hydrogen and carbon atoms, attached to ring carbon atoms
• • C—CHEMISTRY; METALLURGY
  • C07—ORGANIC CHEMISTRY
  • C07D—HETEROCYCLIC COMPOUNDS
  • C07D233/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings
  • C07D233/54—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members
  • C07D233/66—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
  • C07D233/91—Nitro radicals
  • C07D233/92—Nitro radicals attached in position 4 or 5
  • C07D233/95—Nitro radicals attached in position 4 or 5 with hydrocarbon radicals, substituted by nitrogen atoms, attached to other ring members
• • C—CHEMISTRY; METALLURGY
  • C07—ORGANIC CHEMISTRY
  • C07D—HETEROCYCLIC COMPOUNDS
  • C07D249/00—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms
  • C07D249/02—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms not condensed with other rings
  • C07D249/08—1,2,4-Triazoles; Hydrogenated 1,2,4-triazoles
• • C—CHEMISTRY; METALLURGY
  • C07—ORGANIC CHEMISTRY
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  • C07D249/00—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms
  • C07D249/16—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms condensed with carbocyclic rings or ring systems
  • C07D249/18—Benzotriazoles
• • C—CHEMISTRY; METALLURGY
  • C07—ORGANIC CHEMISTRY
  • C07D—HETEROCYCLIC COMPOUNDS
  • C07D295/00—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms
  • C07D295/04—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms
  • C07D295/12—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly or doubly bound nitrogen atoms
  • C07D295/125—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly or doubly bound nitrogen atoms with the ring nitrogen atoms and the substituent nitrogen atoms attached to the same carbon chain, which is not interrupted by carbocyclic rings
  • C07D295/13—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly or doubly bound nitrogen atoms with the ring nitrogen atoms and the substituent nitrogen atoms attached to the same carbon chain, which is not interrupted by carbocyclic rings to an acyclic saturated chain
• • C—CHEMISTRY; METALLURGY
  • C07—ORGANIC CHEMISTRY
  • C07D—HETEROCYCLIC COMPOUNDS
  • C07D295/00—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms
  • C07D295/16—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms acylated on ring nitrogen atoms
  • C07D295/20—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms acylated on ring nitrogen atoms by radicals derived from carbonic acid, or sulfur or nitrogen analogues thereof
  • C07D295/215—Radicals derived from nitrogen analogues of carbonic acid
• • C—CHEMISTRY; METALLURGY
  • C07—ORGANIC CHEMISTRY
  • C07D—HETEROCYCLIC COMPOUNDS
  • C07D295/00—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms
  • C07D295/22—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with hetero atoms directly attached to ring nitrogen atoms
  • C07D295/28—Nitrogen atoms
  • C07D295/30—Nitrogen atoms non-acylated

Definitions

• R is disubstituted acyclic amino or optionally substituted monocyclic or bicyclic heterocyclic amino
• the compounds are useful as contact or systemic biocidal or biostatic agents, especially against mildew and various other fungi.
• This invention relates to novel 1,1,1-trichloro-2-amido- 2-amino-ethanes, as well as to methods of preparing these compounds.
• the present invention relates to compounds of the formula wherein R is hydrogen; alkyl of 1 to 17 carbon atoms; mono-, dior tri-halo-substituted alkyl of I to 17 carbon atoms; alkenyl of 2 to 17 carbon atoms; alkoxy of 1 to 2 carbon atoms; phenyl; 2,4-dichlorophenoxy-methyl; or a-(2,4-dichlorophenoxy)-ethyl; and
• R2 is where R is allyl, cyclohexyl, 2-propinyl, l-methyl-Z-propinyl or 2-cyano-ethyl, and
• R is alkyl of 1 to 4 carbon atoms, allyl or 2-cyanoethyl
• R is where R, is hydrogen, halogen, thiocyano, alkyl of 1 to 4 carbon atoms, alkoxy of 1 to 4 carbon atoms,
• R is hydrogen, halogen, alkyl of 1 to 4 carbon atoms or alkoxy of 1 to 4 carbon atoms
• R is hydrogen, halogen or alkyl of 1 to 4 carbon atoms
• R is alkyl of 1 to 4 carbon atoms, hydroxy-alkyl of 1 to 4 carbon atoms, cyano-alkyl of 1 to 4 carbon atoms, allyl, 2-propinyl, benzyl or cyano;
• R14, R and R16 which may be identical to or different from each other, are each hydrogen or alkyl of 1 to 3 carbon atoms;
• R is hydrogen or alkyl of 1 to 17 carbon atoms
• R is hydrogen, methyl, phenyl, monochlorophenyl, pentachloro-phenyl, nitroso, cyano, p-hydroxy-ethyl,
• R is hydrogen; phenyl; monohalo-phenyl, dihalophenyl, allyl, alkyl of 1 to 4 carbon atoms, or benzyl;
• R is hydrogen, methyl or ethyl
• R and R are methyl or ethyl
• R has the same meanings as in Formula I and R is a substituent which can be readily split off as an anion, preferably bromine or chlorine, with a secondary amine of the formula Rg-H (HI) wherein R, has the same meanings as in Formula I.
• the reaction is advantageously performed in the presence of an acid acceptor, preferably a tertiary aliphatic amine, such as triethylamine. If the amine of the Formula III is a relatively strong base, a commensurate excess over the stoichiometric amount required for reaction with compound II may serve as the acid acceptor.
• the reaction is advantageously also performed in the presence of an inert organic solvent, such as acetone, ether, tetrahydrofuran, methylene chloride, dimethylformamide or a lower alkanol.
• a compound of the Formula I wherein R is a piperazino substituent of the formula shown under (1) above may also be prepared by reacting a piperazine of the formula (I wherein R has the same meanings as in Formula I, with a 1,1,1-trichloro-2-amido-ethane of the Formula II as previously described, or also by converting a 1,1,l-trichloro-2-amido-2-piperazino-ethane of the formula 001: wherein R has the same meanings as in Formula I, into a 1,1,l-trichloro-2-amido-2-(N'-substituted piperazino)-ethane of the formula ll R1-C-NHOHN 4701; by reaction with the desired reaction partner, such as HN0 acylating agent, isocyanate, etc.
• the desired reaction partner such as HN0 acylating agent, isocyanate, etc.
• the starting compounds of the Formula V or their salts may be prepared by reacting a 1,1,1-trichloro-2- amide-ethane of the Formula II with piperazine within a very definite pH-range. If the reaction is carried out at a pH above the optimum value, symmetrical di-substitution products of the formula 0 o Rr-ii-NH-CH-N N-CH-HN-ii-Rr are formed. On the other hand, at a pH below the optimum value no reaction at all takes place.
• the compounds of the Formula V and their salts may be used as starting materials for a variety of asymmetrically substituted piperazine derivatives and are therefore useful as intermediates for the preparation of biocidal and biostatic agents.
• Compounds of the Formula I wherein R is a morpholino substituent of the formula shown under (e) may be prepared by reacting a morpholine of the formula u (VII) wherein R has the same meanings as in Formula I, with a compound of the Formula II in the presence of an acid acceptor; or also by reacting a bis-(fl-chloro-ethyD-ether of the formula l n Cl-GHr-CE 0 (ll-CHs-Cfi 11 (VIII) wherein R has the same meanings as in Formula I, with a 1,1,1-trichloro-2-amido-2-amino ethane of the formula Rr-(ii-NH-OH-NH:
• R has the same meanings as in Formula I.
• the crystalline raw product was recrystallized from methanol, yielding the compound, M.P. 130-131 C., of the formula
• a solution of 5 gm. of N-propargyl-3,4-dichloroaniline and 2.6 gm. of triethylamine in 30 ml. of tetrahydrofuran was added dropwise at room temperature to a solution of 7.2 gm. of N-(1,2,2,(Z-tetrachloro-ethyl)-benzamide in 50 ml. of tetrahydrofuran, accompanied by stirirng.
• N-(lformamido-Z,2,2-trichloro-ethyl)-piperazine were added in several small portions to the bromocyan solution. Thereafter, 2.06 gm. of sodium carbonate were added, and the mixture was stirred for two hours at room temperature. The precipitate formed thereby was collected by vacuum filtration, dried at room temperature and dissolved in chloroform, and the solution was admixed dropwise with ether, yielding the colorless crystalline compound, M.P. 109-110 C. of the formula While vigorously stirring a solution of 2.6 gm. of N-( 1- formamido-Z,2,2-trichloro-ethyl)-piperazine in 20 ml.
• EXAMPLE 13 17.2 gm. of piperazine were dissolved in water, and pH of the resulting solution was adjusted to 2.0 by addition of 2 N hydrochloric acid. While vigorously stirring the acidic solution, 42 gm. of powdered N-(1,2,2,2-tetrachloro-ethyl)-formamide were added in small portions, and simultaneously a concentrated aqueous sodium acetate solution was added at a rate such that the pH was maintained at 201-01. Thereafter, the acidic reaction solution was carefully saturated with potassium carbonate. The oil precipitated thereby was taken up in ethanol, and the resulting solution was allowed to stand for 12 hours at room temperature.
• EXAMPLE 15 2.6 gm. of N-(1-formamido-2,2,2-trichloro-ethyl)-piperazine were dissolved in 5 ml. of 2 N hydrochloric acid, the solution was cooled to 5 C., and then a solution of 0.97 gm. of potassium cyanate in 20 ml. of water was 0.71 ml. of methyl isocyanate were added to a solution of 2.6 gm. of N-(1-formamido-2,2,2-trichloro-ethyl)- piperazine in 10 ml. of absolute tetrahydrofuran, and the TABLE I 10 resulting mixture was allowed to stand at room temperature for 18 hours.
• H CH-N 20 CH3 85417 (benzene) NC-CHz-CHz-lh- 21 (NCCH2CH2)2N 125-127 (ethanol/water) 22 CH3 87-88 (ethylacetate/hexane) CeHlN 23 01H; 118-119 (lsopropanol) (kHz- 24 CH(CH;); 165-167 (ethanol) Decomposition.
• the compounds according to the present invention that is, those embraced by Formula I and their acid addition salts, have useful biocidal and biostatic properties. More particularly, the compounds according to the present invention are useful for combatting a broad spectrum of pathogenic fungi and bacteria, such as mildew, Asperfillus, Xanthomonas, Pseudomonas and Fusarium, and for combatting insects and acarids, such as aphids and spider mites.
• R is hydrogen, and R is a substituents defined under (b), where R-; and R are hydrogen and R is chlorine or bromine, or R is hydrogen and R and R are chlorine or bromine; a substituent defined under (f); the substituent defined under (g); or a substituent defined under (1), where R is preferably hydrogen, methyl, nitroso, cyano, fi-hydroxy-ethyl,
• R R R and R have the meanings previously defined.
• the compounds of Examples 3, 30, 31, 34, 37, 38, 39, 40, 43, 64, 67, 74 and 75 are especially effective as contact fungicides against genuine mildew fungi on plants; the compounds of Examples 12, 44, 49 and 55 are especially effective systemic fungicides against mildew fungi on plants; the compounds of Examples 5, 13, 53, 65, 66 and 72 are effective contact and systemic fungicides against mildew fungi on plants.
• Aspergillus niger The growth of Aspergillus niger is effectively inhibited, for example, by the compounds of Examples 11, 19, 23, 24, 25, 28, 37, 42, 43, 48, 57, 61, 74, 76, 77, 79, 110, 141 and 169.
• Effective against F usarium oxysp. are, for example, the compounds of Examples 10, 37, 74, 75, 76, 77 and 79.
• Very eeifctive bacteriocides against Pseua'amonas morspruncrum are, for example, the compounds of Examples 57, 71, 74, 77 and 79; against Xanthomonas malv. the compounds of Examples 10, 42, 57, 74, 76, 77 and 79; against Pythz'um ultim. the compounds of Examples 9, 10, 57, 74, 76 and 79; and against Rhizoctonia solani the compounds of Examples 9 and 10.
• the compounds according to the present invention are applied to areas infested with such microorganisms as active ingredients in conventional liquid or solid compositions, such as dusting powders, suspensions, emulsions, solutions, aerosols and the like.
• Such compositions may additionally comprise conventional inert auxiliary ingredients, such as emulsifiers, diluents and adhesion-enhancing agents, as well as other biocidal or biostatic ingredients.
• the effect tive concentration range of the compounds of the instant invention in such compositions is from 0.00001 to 1% by weight, preferably 0.01 to 0.5% by weight, based on the total weight of the composition. Dusting powders and socalled ultra-low-volume (ULV) compositions may have a higher concentration of active ingredient.
• UUV ultra-low-volume
• compositions comprising a compound according to the present invention as an active ingredient and represent the best modes contemplated of putting the invention into practical use.
• the parts are parts by weight unless otherwise specified.
• EXAMPLE Dusting powder The powder was compounded from the following ingredients:
• the ingredients were admixed with each other in conventional fashion to make an emulsion concentrate which, prior to use, was emulsified in a sufiicient amount of water to make the active ingredient conventration in the aqueous emulsion between 0.0001 and 0.5% by weight, based on the total weight.
• the resulting sprayable aqueous was Parts 1,1,1 trichloro 2 formamido 2 (N-ethoxycarbonylpiperazinoethane 80 Calcium lignin sulfonate 8 Colloidal silicic acid Sodium sulfate 5 Diisobutyl-naphthalene sodium sulfonate 2 EXAMPLE 193 Aerosol spray The aerosol composition was compounded from the following ingredientsz Parts 1,1,1 trichloro 2 formamido 2 (N'-formylpiperazino)-ethane 0.05 Sesame oil 0.10 N-Methyl-pyrrolidone 10.00 Mixture of Frigen 11 and 12 89.85
• the trichloroethane compound, the sesame oil and the N- rnethyl-pyrrolidone were admixed with each other, and the mixture'was charged into an aerosol can equipped with an aerosol spray valve.
• the cans were then pressurized with the propellant gas mixture in conventional manner.
• the aerosol spray discharged from the pressurized can was an effective fungistatic contact composition for use in inhibiting the growth of Aspergillus niger.
• R is hydrogen; lower alkyl; or monoor di-halo-substituted lower alkyl; R is hydrogen; alkyl of 1 to 3 carbon atoms; nitro; or phenyl; and R is hydrogen; alkyl of l to 3 carbon atoms; or

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• Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
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• Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
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  • BE BE756062D patent/BE756062A/fr unknown
• 1969
  • 1969-09-11 DE DE19691946112 patent/DE1946112A1/de active Pending
• 1970
  • 1970-08-20 CS CS5749A patent/CS173572B2/cs unknown
  • 1970-08-20 CS CS3680A patent/CS173596B2/cs unknown
  • 1970-09-04 GB GB4254370A patent/GB1319479A/en not_active Expired
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  • 1970-09-10 US US71262A patent/US3707477A/en not_active Expired - Lifetime
  • 1970-09-10 JP JP45078930A patent/JPS5224003B1/ja active Pending
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  • 1970-09-11 RO RO7077239A patent/RO73179A/fr unknown
  • 1970-09-11 AT AT725771A patent/AT302331B/de not_active IP Right Cessation
  • 1970-09-11 RO RO7000064434A patent/RO67862A/fr unknown
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• 1971
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