• 专利附录
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    • 专利摘要:
    2-Arylamino-hexahydropyrimidines and imidazolidines of formula …<CHEM>… wherein n is 0 or 1, R1 and R2, equal or different, represent hydrogen, alkyl, alkyloxy or alkylthio having from 4 to 12 carbon atoms, cycloalkyl having from 3 to 7 carbon atoms, bezyloxy, benzylthio, phenoxy or phenylthio optionally substituted with halogen or C1-C4 alkyl, phenylalkyl having from 7 to 11 carbon atoms, of which the phenyl group is optionally substituted with halogen, dialkylamino, or with alkyl, alkoxy or alkylthio, which alkyl, alkoxy or alkylthio have from 1 to 6 carbon atoms and are optionally halogenated, furylalkyl or thienylalkyl of which the alkyl groups have from 1 to 4 carbon atoms, dialkylamino of which the alkyl has from 2 to 6 carbon atoms, or alkoxycarbonyl having from 4 to 12 carbon atoms, or wherein R1 and R2 together represent trimethylene, tetramethylene or butadienylene with the proviso that R1 and R2 are not both hydrogen atoms, R3, R4, R7 and R8, equal or different, represent hydrogen or alkyl having from 1 to 4 carbon atoms, and R5 R6, equal or different, represent hydrogen, alkyl having from 1 to 4 carbon atoms or alkanoyl having from 2 to 5 carbon atoms, as well as salts and complexes of these compounds, have fungicidal activity. …<??>The compounds are particularly active against rust of beans, brown rust of wheat and milden on cereas. …<??>After having been processed to compositions, the compounds can be used successfully to prevent or control mould infections in agriculture and horticulture in a dosage of 200-1000g. of active substance per hectare. Very active fungicides are 2-(4-cyclohexyl-phenyl)- iminohexahydropyrimidine and 2-(4-n-hexyl- phenyl)- iminohexahydropyrimidine, as well as the sulphuric acid salts of these compounds and complexes with zinc salts.
    公开号:SU969160A3
    申请号:SU802891001
    申请日:1980-02-28
    公开日:1982-10-23
    发明作者:Долман Хендрик；Кэйперс Йоханнес
    申请人:Н.В.Филипс Глоэлампенфабрикен (Фирма)；
    IPC主号:
    专利说明:

    This invention relates to methods for producing new derivatives of hexahydropyrimidines or imidazolidines, which have valuable fungicidal properties that can be used in agriculture. Known is the reaction of cyclization of 1,3-diamines to pyrimidine or 1,2-diamine derivatives to imidazole derivatives by introducing a carbon atom via carbonic acid derivatives. The purpose of the invention is to obtain new hexahydropyrimidines or imidazolidines derivatives that have fungicidal properties. The goal is achieved by the fact that according to the method of obtaining 2-ar amino hexahydropyrimidines or azolidine imide of the general formula, halogen or alkyl with 1-4 carbon atoms, phenylalkyl with 7-12 carbon atoms, which can be substituted with halogen, alkyl or alkoxy with 1-6 carbon atoms, furylethyl, dialkylamino, where alknp with 2-6 carbon atoms, or alkoxycarb it contains 4-12 carbon atoms; hydrogen or hexylthio, or K and R together form a tetramethylene group; are the same or different and are hydrogen or alkyl with 1-4 carbon atoms, or their complexes in the salt of the general formula
    2- ((4-Isopropoxyphenyl) -ethiphenyl Uiminoghexahydropyrimidine, m.p.L.S.
    (4-Chlorophenyl) -ethyl-phenyl | ) iminohexahylopyrimidine, so pl. 149C.
     (2- (2-Chlorophenyl) -ethyl-phenyl w / shnohexahylopyrimidine, m.p. 153 C.
    2-C4- (2-C3, 4-Dichlorophenyl) -ethyl-3-phenyl and 14-hexohydropyrimidine,
    mp.124C. .
    (2-furylethyl) -phenyl iminohexahylopyrimidine, m.p.
    2- (4-gisopentylthiophenyl) iminohexahydropyridshdin.
    2-14- {2- (4-and-Kuto, Xyphenyl) -ethyl-phenylZiminohexahylopyrimidine.
     G2- (4-Beneylphenyl) -ethyl-phenyl iminohexahydropyrimidine.
    2- (4-Benzylphenyl) iminohexahydro pyrimidine, m.p.
    2-G4-G 2-Phenylethyl) -phenyl iminohexahylopyrimidine, i.e. 146 C.
    2- (4-n-Butylthiophenyl) imyiohex. Hydropyrimidine, mp.92C.
    2-f3-n-hexylthiophenyl-jiminogaxhydropopymidine, liquid ,, 588
    2- (4-m-Octylthiophenyl) iminohexahydropyrimidine, mp 95.5-94.5 ° C.
    2- (4- (4-Methylphenylthio) -phenyl by them noghexahylopyrimidine, mp 126128,.
    2- 4-f4-chlorophenylthio) phenyl-linohexacidipopyridimidine, m.p. 1.148C.
    2- (4-n-Hexyloxyphenyl) sh1INo. Hexahydropyrimidine, so pl. 117 C.
    2- (4-Oxyloxyphenyl) and auger-hydropyrimidine, t.pcs.113 C.
    2- (4-n-Dodecyloxyphenyl) iminohexahydropyrimidine, mp 112-112.5
    2- (4-n-Hexyloxycarbonylphenyl) iminohexahydropyrimidine, m.p. .
    2- (4-and-Octyloxycarbonylphenyl) imhexachropropyrimidine, m.p. 100101, 50c.
    2- (4-N, N-Di6 ytilaminophenyl) imino hexahydropyrimidine, viscous liquid
    2- (| -Naphyl) iminohexahylopyrimidine, mp.150C.
    1-Methyl-2- (4- "-butylphenyl) iminohexahydropyrimidine, liquid, 1.567.
    1-Methyl-2- (4-m-hexylphenyl) iminohexahylopyrimidine, liquid, h 1.554.
    1-Methyl-2- (4-cyclohexylphenyl) imnohexahylopyrimidine, liquid.
    2- (4-Cyclohexylphenyl) imino-5,5-dimethylhexahylopyrimidine, so pl. . (rael.)
    2- (4-and-Butylphenyl) iminoimidazolidine, m.p.
    2-C4-Cyclohexylphenyl) imino | imidazolidine, m.p. 163-165 0 radl.
    2- (4-n-Hexylphenyl) iminoimide azolidine, mp.
    2- (4-and-heptylphenyl) by them nimidazolidine, mp. 88-90C.
    2- (4-n-octylphenyl) iminoimidazolidine, t.Sh1.80-82S.
    2- (4-n-Butylthiophenyl) iminoimidazolidine, m.p.
    2- (4-n-Hexylthiophenyl) iminoimidazolidine, m.p.
    2- (4-and-OkTylthiophenyl) iminoimidazolidine, mp 69-71 ° C.
    (4-Methylphenylthio) -phenyl iminoimidazolidine, m.p.
    2-14- (4-Chlorophenylthio) -phenyl iminoimidazolidine, m.p.
    2- (4-δ-Octyloxycarbonylphenyl) by them noimidazol din, m.p. 78.-83s
    (4-Chlorophenylthio) -phenyl iminoimidnzolidine, m.p.
    (4-Methylphenyl) -til-phenyl iminohexahydropyrimidine, mp, 161 ° C.
    2- (4-Cyclohexylphenyl) imino-4-methylhexahydropyrimidine, m.p. .
    2- (4-n-Butylphenyl) imino-4-methylhexahydropyrimidine, oil.
    2- (4-n-octylphenyl) imino-4-methyl hexahydropyrimidine, m.p.
    2-G4-12-C2-Methylphenyl) -ethyl-phenyl II11 noghexahylopyrimidium n, oil.
    (4-Isopropylphenyl) -ethyl-phenyl iminohexahylopyrimidine, mp.154 C.
    Example 4. Preparation of 2- (4-cyclohexylphenyl) iminohexahylopyrimidine sulfate.
    37 g of 2- (4-cyshohexylphenyl) iminohexahylopyrimidine is dissolved in 140 ml of 1N. sulfuric acid. After distillation under vacuum, 2- (4-cyclohexylphenyl) iminohexahylopyrimidine sulfate is obtained, m.p. 260 ° C.
    Similarly, the following compounds are obtained (using organic acids, the reaction is carried out in methylene chloride or acetonitrile):
    2- (4-Cyclohexylphenyl) iminohexahydropyrimidine cinnatum, t.Sh1.170171C.
    2- (4-Cyclohexylphenyl) iminohexahydropyrimidine 2-chloroethane phosphonate, m.p.
    2- (4 -); iclohexylphenyl) iminohexahydropyri1 1idine para-dodecylbenzenesulfonate.
    2- (4-Cyclohexylphenyl) iminohexahylopyrimidine acetate, m.p. 170C.
    2- (4-m-Octylphenyl) iminohexahydropyrimidine acetate, mp 755 C, phosphoric acid ethyl ester and 2- (4-cyclohexylphenyl) iminohexhydropyrimidine, phosphoric acid butyl ester and 2- (4-cyclohexylphenyl) with noghexagropyrimidiimide on them .
    Example 5. Obtaining 2- (4-cyclohexylLenyl) and .minohexahydropyrimidine zinc chloride complex.
    10.3 g of 2- (4-cyclohexylphenyl) iminohexahylopyrimidine is dissolved in 150 ml of warm acetonitrile. To this solution is added a solution of 2.7 g of zinc chloride. The complex has a mp. . The structure is confirmed by the data of the IR spectrum.
    Similarly, fumed compounds are prepared;
    2- (4-Cyclohexylphenyl) iminohexahydropyrimidine zinc acetate complex m.p. .
    2- (4-Cyclohexylphenyl) iminohex hydropyrimidine acetate acetate mixture, so pl. 114C.
    2- (4-n-Octylphenyl) iminohexahydropyrimidine zinc chloride complex, mploo C.
    2- (4-and-Butylphenyl) and No. of hexa-. hydropyrimidine copper-acetate complex, so pl. 70 ° C.
    Example 6. Based on the compounds prepared in accordance with the invention, compositions are prepared by suspending these compounds in water in the presence of a dispersing agent, for example, ligninsulfonate and / or a wetting agent, such as naphthalene sulfonate, alkyl, sulfate, apkylbenzenesulfate, alkylpolyene glycol glycol, or alkylpolyalkylphenol sulfonate, alkyl sulfolate, acetylbenzene sulfate, alkyl polyol glycol glycol or alkylate glyphenol sulfonate, alkylate glycol glycol sulfonate, alkylate glycol or alkylate glycol glycol glycol glycol sulfate In some cases, the compounds are dissolved in water, if necessary, using a water-miscible organic solvent and, if necessary, in the presence of an emulsifier.
    Then the culture to be protected from the rust beans (Uromyces phaseoli) is processed by the resulting composition by spraying.
    The results of such processing are given in tab. 1, where the minimum concentration of one or another compound (in parts per lion) is indicated, at which effective protection against the effect of Uromyces phaseoli sprouts of French stump beans can be ascertained.
    Example 7. A culture that is to be protected from exposure to brown wheat flour (Puccinia recondite), subjected to treatment by spraying with three or other compositions, the absorption of which is shown in Example 6.
    The results of this treatment are given in Table 2, where the minimum concentration of the compound used is given, at which the effective protection of wheat against the negative effects of Puccinia recondita is still stated.
    PRI me R 8. Culture, subject to protection from exposure to downy mildew on cereals (Erysiphe graminis), is sprayed using one or another composition, the preparation of which is described in Example 6.
    The results of this treatment are shown in Table 3, where it is given, the minimum concentration of the compound used, at which the protection of the barley against Erysiphe: graminis is found to be effective.
    Example 9. The culture to be protected by QT of mildew on the blocks (Podosphaera leucotricha) is treated with the composition shown in Example 6. The treatment is carried out by spraying young plants with a height of approximately 15 cm, an aqueous suspension or a solution containing the compound subjected testing, at various concentrations. After drying, the seedlings are infected with spores Podosphaera leucotricha. Following an incubation period of 14 days and passing at 80% and relative humidity, a test of mold development, if any, is carried out.
    The results are shown in Table 4, where the minimum concentration of the compound used is indicated, at which effective protection of the seedlings of blon is found to be effective against exposure to Podosphaera leucotricha. Table 1
    2- (4-14-Butyl phenyl) iminohexahydropyrimidine
    2- (4- -Hexylphenyl) iminohexahylopyrimidine
    . ten
    ten
    2- (4-Cyc ohexyl phenyl) ig "1 hexahydropyrimidine
    2- (4-and-Octylphenyl) iminohexahylopyrimidine
    2- C 4-n-Bu til thiof.enil) they nochexahydropyudyudi n
    2- (3-n-Hexylthiophenyl) iminohexahydropyrimidine
    2- (4-m-Hexylthiophenyl) iminohexahydropyrimidine
    2-f4- (4-Methylphenylthio) -phenyl iminohexahydropyrimidine
    2-C4- (4-Chlorophenylthio) -phenyl min-hexa-hydropyrimidine
    2- (4-n-Hexyloxycarbonylphenyl) iminrhexahydropyrimidine
    2- (4-n-octyloxycarbonylphenyl) iminohexahydropyrimidine
    2- (4-m-octylphenyl) iminohexamidazolidine
    2- (4-Cyclohexylphenyl) imine-imidazolidine
    2- (4-n-Hexylthiophenyl) iminomidazolidine
    2- (4-n-Butylthiophenyl) iminomidazolidine
    2-t4- (4-Methylphenylthio) -phenyl shnimimidazolidine
     4-Chlorophenylthio) -phenyl minimide: olidi n
    1,3-diacene.-2- (4-cyclohexylene) iminohexahylopyrimidine
    2- (4-n-Pentylphenyl) iminohexahyropyridine
    2- (4-n-heptylphenyl) iminohexahydropyrimidium
    2- (4-Benzyl phenyl) iminohexahyridyrimidine
    2-C4- (2-Phenylethyl) -phenyl iminohexahydropyrimidine
    2- (4-h-Hexylphenyl) imino-1methylhexahydropyrimidine
    Continuation of table 1
    ten
    ten
    ten
    10-30
    ten
    ten
    ten
    "ten
    ten
    ten
    SJ 10 10 10
    ten
    ten
    10 10
    10-30 10.-30 10-30
    2- (4-c-Hexylphenyl) iminoimidazolidine
    2- (4-and-heptylphenyl) iminoimidaeolidine
    2- (4-c-Butylphenyl) iminoimidazolidine)
    2- (4th-Octylphenyl) iminoimidazolidine
    2- (4-8TCip -Oxyloxycarbonylphenyl) I1 11oimidaeolidine
    2-C4- (4-Chlorophenylthio) -phenylZimino-4-methylimidazOLIDine
    2- (4-Cyclohexylphenyl) imino-hexahydrope and Iidine sulfate
    2- (4-Cyclohexylphenyl) imino-hexahydropyrimidine Cinnamo
    2- (4-Cyclohexylphenyl) iminohexahydropyrimidine-2-chloro-phosphanate
    2- (4-Cyclohexylphenyl) iminohexahydropyrimidine paradodecylbenzene sulfonate
    2- (4-Cyclohexylphenyl) imino-hexahydropyrimidine acetate
    2- (4-n-Butylphenyl} iminshexahydropyrimidine
    2- (4-n-Hexylphenyl) iminohexahydropyrimidine
    2- (4-Cyclohexylphenyl) iminohec sagidropiri midi n
    2- (4-n-Octylphenyl) iminohexagydropirimidin
    2- (4-n-Decylphenyl) iminohexahydropyrimidine
    2- (4-n-Hexylthiophenyl) iminohexahydropyrimidine
    2- (4-and-Hexyloxycarbonylphenyl) they nogheksagidropirimid
    Continued table. 12
    10-30 10-30 10-30 10 10-30 10-30
    one
    ten . ten
    ten
    10 10
    table 2
    300 5 300 100-300 100-300 300
    300
    300
    2-c4-Cyclohexylphenyl) iminodimethylhexahydropyrimidine
    2- (4-n-heptylphenyl) iminohexahydropyrimidine
    2- (4-n-Nonylphenyl) iminrhexahydropyrimidine
     (2-Phenylethyl) -phenylZiminohexahydropyridimidine
    2- (4-Cyclohexylphenyl) iminohexahydropyrimidine sulfate
    2- (4-Cyclohexylphenyl) iminohexahydropyrimidine Cinnammate
    2- (4-Cyclohexylphenyl) iminohexahydropyrimidine 2-chloroethane phosphonate
    2- (4-Cyclohexylphenyl) iminog Exahydropyrigl1din pair dodecyl benzene sulfate
    2- (4-Cyclohexylphenyl) imino-hexahydropyrimidine acetate
    2- 4-t2- (4-Methylphenyl) -ethyl5-phenyl, iminohexahydropyrimide
    2- (4-Cyclohexylphenyl) imino-4-methyl-hexahydropyrimidine
    2- (4-Kt-Butyl phenyl) imino. -4-methylhexahylopyrimidine
    2-C4-c-Octylphenyl) imino-4-methyl hexahydropyrimidine
     (4-Chlorophenyl) -ethyl phenyl, iminohexahydropyrimide
    2- (4-and-Butylphenyl) iminohexahydropyrimidine
    2- (4-Isobutylphenyl) iminohexahylopyrimidine
    2- (4-and-Hexylphenyl) iminohexahydropyrimidine
    2- (4-Cyclohexylphenyl) iminohexahydropyrimidine
    Continued table. 2
    300
    300
    300
    100-300 100-300 100-300
    100-300 100-300
    100
    100-300
    100-300
    300
    300
    100
    Table
    100 100
    100-300 100
    2- (4-and-Butylthiophenia) imino-hexahydropyrimidine
    2- (4-c-Hexylthiophenyl) iminohexahydropyrimidine
    1-Methyl-2- (4-cyclohexyl-g phenyl) they nogheksahidropirimidi n
    2- (4-Cyclohexylphenyl) imino5, 5-dimethylhexahylopyrimidine
    2- C | L-Naftch1) iminohexahydropyrimidine
    2- (3,4-Tetramethylenephenyl) iminohexahydropyrimidine
    2- (4 N-GephilfeNIL) iminoge to the Dopyrimidine saga
    2- (4-n-Hohnylphenyl) imino hexahydropyrimidine
    2- (4-and-dodecylphenyl) imino. Hexahydropyrimidine
    2- (4-isopentylthiophenyl) iminoge to the saga
    2- | 4-C2- (4-Methylphenyl) -ethyl) phenyl IGI nogheksagi dropirimi din
    2- 4-t2- (4-Chlorophenyl) ethyl phenyl iminohexahylopyrimidine
    (4-Isopropyloxyphenyl) -ethyl-phenyl} iminohexahydropyrimidine
    (2-Methylphenyl) -ethyl5phenyl1 yminohexahydropyrimidine
    2- 4- () urileethyl) -phenyl iminohexahydropyrimidine
    2- (4-Isopropylphenyl) -ethyl / phenyl iminohexahyropyridine
    (4-Ethoxyphenyl) -ethyl phenyl | yminohexahydropyrimidine
    2-4-E2- (4-n-Butoxyphenyl) Etilphenyl iminohexahylopyrimidine
    2- (4-Benzylphenyl) iminohexahylopyrimidine
    2-t4- (2-Phenylethyl) -phenyl iminohexahydro-pyrimidine
    2-C 4-m-Butylphenyl) imno-1methylhexahydropyrimidine
    Continuation of table.3 2
    100 . 300 100 100 100 300 300 100
    300
    100-300 100 100
    100 .
    100
    100
    100
    100
    300
    300 300 00-300
    2-C 4-N, N-Dibutylaminophenyl) iminohexahylopyrimidine
    2- (4-Cyclohexylphenyl) imino-4methylheg sagi-droprimim di n
    2- (4-Cyclohexylphenyl) imiirhexahydropyrimidine sulfate
    2- (4-Cyleslohexylphenyl Ziminoghexahylopyrimidine Cinnammate
    2- (4-Cyclog.exilfeiyl) iminohexahydropyrimidine 2-chloroethane phosphonate
    2- (4-Cyclohexylphenyl) iminohexahydropyrimidine para-dodecylbeisol sulfonate
    2- (4-Cyclohexylphenyl) iminohexahylopyrimidine acetate
    2- (4-Cyclohexylfeiyl) iminoge to sagipropirimidium terrestrial complex
    2- (4-Cyclohexylfeiyl) imiohexahydropyrimidium zinc-acetice clawot
    2- (4-n-Octylpheyl) imyiohex. hydropyrimidine yeschet
    2- (4-n-Octylphenyl) iminohexahydro-pyrimidinzinc chloride.
    complex
    Compound
    2-4-Octylphenyl) iminohexahylopyrimidine
    2- (4-Benzylphenyl) iminohexahylopyrimidine
    2-t4- (2-Phenyl) phenyliminohexahydropyrimndin
    2 - (. 4-Octylthiophenyl) iminohexahylopyrimndin
    Continued table. 3 2
    100-300 100-300 100-300 100-300
    100-300
    100-300 100-300
    100-300
    100-300 300
    300
    Table 4
    Minimum concentration, in parts per million
    100-300
    100
    权利要求:
    Claims (1)
    [1]
    100 .100-300. Formula of the invention. Method of obtaining 2-arylaminohex-, sagidropirimidines or imidazolidines of the general formula 1 / WrXi-p-Ov I-O or Ij , cyclohexyl, benzyloxy, benzylthio, phenoxy groups of the phenylthio group, which can be substituted by halo gene or alkyl with 1-4. carbon atoms, phenyl kil with 7-12 carbon atoms that can be substituted with halogen, alkyl or alkoxy with 1-6 carbon atoms, furylethyl, dialkylamino where alkyl with 2-6 carbon atoms, or alkoxycarbonyl with 4-12 carbon atoms ; hydrogen or hexylthio, or R and R together form a tetramethylene group; are the same or different and are hydrogen or alkyl with 1-4 carbon atoms, or their salts, or their complexes with metal salts, characterized in that the compound of the general formula II where R and R have the indicated meanings and-2 are halogens or alkythio, or y is an amino group, and Z is an alkoxy or alkythio group, is reacted with a diamine of the general formula. R-NH-I-c-j-CH-NHR,:, -. RL A where R-rR has the indicated meanings, in a polar organic solvent at a temperature of from. at room temperature to the boiling point of the solvent, followed by treating the resulting product with a base and isolating the desired product as a base or salt, or complex with metal salts. Sources of information taken into account in the examination 1. Heterocyclic compounds. Ed. R. Elderfield. M., Foreign literature, v.6, p.204,. T.5. p.190.
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    引用文献:
    公开号 | 申请日 | 公开日 | 申请人 | 专利标题
    US2899426A|1959-08-11|Synthesis of l |
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    申请号 | 申请日 | 专利标题
    NL7711390A|NL7711390A|1977-10-18|1977-10-18|NEW 2-ARYLIMINO-HEXAHYDOPYRIMIDINES AND IMI-DAZOLIDINES, SALTS AND COMPLEXES THEREOF, METHOD FOR PREPARING THE NEW COMPOUNDS, AND FUNGICIDE PREPARATIONS BASED ON THE NEW COMPOUNDS.|
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