• 专利附录
  • 专利说明
  • 权利要求
  • 类似技术
  • 同族专利
  • 引用文献
  • 法律状态
  • 优先权
    • 专利摘要:
    1. METHOD OF OBTAINING CHINOXALINE DERIVATIVES of the general formula where A, B, D and E are hydrogen, halogen, nitro, amino, di- (C-C5-alkyl) -amino, C, -Cg-alkyl and C-Cg-haloalkyl group} J, and and V is hydrogen or halogen; R, is hydrogen, C-C is alkyl groups and C-Cj-alkoxycarbonyl groups; RJ is hydrogen and Cf-C alkyl groups; W-rpynna-C-G, where | O G - hydroxyl group, C-Cg-alkoxy group, Cj-Cg-alkenyloxy group, O-alkyloxy group, C, -Cb-alkylthio group, cyclohexyloxy, C-C-alkoxy group substituted by a substituent from the group including NN-di- (C -C-ALK) -ami-. § footgroup, N, N, N-tri- (C, -C-alkyl) -amO) monium group} s or G-group of the formula -0-N-R 9, where, -Cg-alkylide-, is a new group; or G is the OM group, ke, where M is an alkaline metal ion} O5 X is oxygen, J is oxygen or sulfur, k and E is O, and lik-H is 0 or 1, characterized in that i is a quinoxaline derivative of the formula OJ where Z is halogen, A, B, D, E, J, kn have the indicated meanings.
    公开号:SU1261564A3
    申请号:SU2951003
    申请日:1980-07-16
    公开日:1986-09-30
    发明作者:Сербан Александр；Джеффри Ватсон Кейт；Джон Фарквахарсон Грим
    申请人:Ай-Си-Ай Аустрэлия Лимитед (Фирма)；
    IPC主号:
    专利说明:

    R, is hydrogen. C, -C-alkyl and C, -C-alkoxycarbonyl,
    R is hydrogen and C, -Cg-alkyl
    O W —C — G, G — hydroxy group,
    C, -C, d-alkoxy-C-C, -alkenyloxy, a-alkynyloxy-, C, -C,;, -alkylthio, cyclohexyloxy-, OM, where M is an alkali metal ion;
    J is oxygen or sulfur;
    X is oxygen;
    to about; p 0.
    11.04.80 J - Halogen-C-C o-alkoxy group substituted by a substituent from the group N, N-di- (C, -Cj-alkyl) -amino, N, N, N-tri- (C, -Cg-alkyl -ammonium group, or 0-NR, where R, is (C, -Cg) -alkylidine group,, or 1, .. or 1, and k + or 1.
    one
    The invention relates to a method for producing new quinoxaline derivatives having herbicidal activity that can be used in agriculture.
    The aim of the invention is a method for producing new quinoxaline derivatives having improved herbicidal activity.
    Example 1. Preparation of methyl 2- 4- (6-chloro-quinoxalinyloxy) pheno-β-propionate (1).
    A mixture of 2,6-dichlrrhinoxaline (10 mmol) obtained from 4-chloro-1, α-dinitrobenzene and amino acetic acid ethyl ester, methyl 2- (4-hydroxyxyphenoxy) propisnate (10 mmol), anhydrous sodium carbonate (11 mmol) and dimethylformamide (40 ml), heated under reflux for 3 hours. The reaction mixture is then cooled and poured into water. The aqueous organic mixture is extracted with diethyl ether. The ether extract is dried over anhydrous sodium sulfate and the solvent is removed by distillation under reduced pressure, to obtain a solid residue. Solid residue
    recrystallized from methanol, methyl 2- 4- (6-chloro-2-quinoxalininyloxy) propionate is obtained in the form of white needles (2.5 g, 70%) with m, pl. 126 ° C.
    The proposed compound structure was confirmed by proton magnetic resonance spectroscopy and mass spectrometry.
    Example 2. Preparation of methyl 2- 4- (6-chlorop-1-oxide-xynoxalin-2-yloxy) phenoxyl propionate (4).
    A. Potassium persulfate (7.42 g) is slowly added to a mixture of 2,6-dichlorochinoline (5.0 g) and concentrated
    sulfuric acid (25 ml) with stirring at 10 ° C. After adding potassium persulfate, the reaction mixture is allowed to warm to room temperature and stirring is continued for another 24 hours. After that, the reaction mixture is poured into ice-water (400 ml), neutralized with an aqueous solution sodium bicarbonate and extracted with methylene chloride. The organic extract is washed with a complete solution of common salt, dried over anhydrous sodium sulphate and then the solvent is evaporated. The solid residue is recrystallized from ethyl alcohol, to obtain 2,6-dichloroquinoxalin-1-oxide in the form of brown needles with so pl. 185 ° C. B. A mixture of 2,6-dichloroquinoxaline-1-oxide (1.0 g; 4.7 mmol), met1-2- (4-hydroxyphenoxy) propionate (0.92 g; 4.7 mmol) -, anhydrous carbonate potassium (0.65 g - 4.7 mmol) and methyl ethyl ketone (70 ml), heated under reflux for 30 hours. Then the solvent was removed by distillation under reduced pressure and the residue was partitioned between methylene chloride and water. The organic layer is separated and dried, the solvent is evaporated, and a dark oil is obtained. The oily residue is chromatographed on a column filled with silica gel (40 g), using methylene chloride as the solvent. In the end, 2- 4- (6-chloro-oxyhonoxalin -2-yloxy) -phenoxy-propionate is obtained as a pale brown solid (0.75 g; 43%), i.p. 110 ° C. The proposed structure was confirmed by proton magnetic resonance spectroscopy and mass spectrometry. Example 3. Compounds 18-25, 35-38, 40-43, 48, and 49 are summarized in Table. 1, were obtained from the corresponding quinoxaline and the corresponding alkyl- (hydroxyphenoxy) -alkane carboxylate, followed. essentially the procedure described in Example 1 or Example 2, Compound 47 (see Table 1) was prepared by reacting 2,6-dichlorochinazoline and diethyl 2- (4-hydroxyphenoxy) -2-methyl maponata, following the same procedure, as described in example 1. The proposed structure of the obtained compounds was confirmed by spectroscopy. proton magnetic resonance and mass spectroscopy. Example 4. Obtaining (6-chloro-2-quinoxalinyloxy) -phenoxy-propionic acid (29). A mixture of 2,6-dichloroquinoxaline (10 mmol), 2- (4-hydroxyphenoxy) -propionic acid (10 mmol), without aqueous potassium carbonate (20 mmol) and dry dimethylformamide (50 mp) is heated under reflux in a for 3 hours. Then the reaction mixture is cooled and drunk into water. As a result of the sub-644 acidification of the aqueous-organic mixture with a 15% aqueous solution of HCR, a solid precipitate is formed, which is separated by filtration. The dried product is recrystallized from toluene, in the end, (6-chloro-2-quinoxalinyloxy) -pheoxy-propionic acid is obtained in the form of a white crystalline substance, having so pl. 130 C (with decomposition). The proposed structure was confirmed by proton magnetic resonance spectroscopy and mass spectrometry. Example 5. Sodium (6-chloro-2-quinoxalinoxy) -phenoxy-prprionate (30) is obtained by neutralizing the appropriate acid (Example 4) with an aqueous solution of sodium hydroxide and removing the solvent under reduced pressure. Example 6. Obtaining n-propyl-2- 4- (6-chloro-quinoxalinyloxy) -phenoxy-propionate (26). A. A mixture of (6-chloro-2-quinox-link) -phenoxy-propionic acid (2.0 g, Example 4) and thionyl chloride (15 ml) is heated under reflux for 1 hour. After removing the excess. thionyl chloride was obtained by distillation. (6-chloro-quinoxalinyloxy) phenoxy-propionyl chloride. B. A mixture of propionyl chloride. prepared as described under A, n-propanol (10 ml) and triethylamine (2 ml) was stirred at room temperature for 30 minutes. After that, the mixture is poured into water (100 mp) and the resulting aqueous-organic mixture is extracted with diethyl ether. The ether extract is dried over anhydrous sodium sulphate and then the solvent is removed by distillation under reduced pressure, and n-proPS1-2-4- (6-chloro-quinoxalinyloxy) -phenoxyT-propionate is obtained as a white crystalline substance with mp. 80 C. The proposed structure of the product is confirmed by proton magnetic resonance spectroscopy and mass spectrometry. Example 7. Compounds 17, 2628, 33, and 46, described in detail in Table. 1, were obtained from (6-chloro-quinoxalinyloxy) -phenoxy-propionol chloride (see Example 6, A) and the corresponding alcohol or thiospirt, following the same procedure as
    described in Example 6B, Compound 32 (see Tab. 1) was prepared in a similar way from (6-chloro-2-quinoxalinyloxy) phenoxy-propionyl chloride and acetone oxime. The proposed structures for each of the above compounds were confirmed by proton magnetic resonance spectroscopy and mass spectrometry, and the corresponding physical data are given in Table. 2
    Example 8. 2- (N, S, M-Trimethammonium) -ethyl-2- A- (6-chloro-2-xinoxaliniloxox) -phenoxy-propionate iodide (34) is obtained by the interaction 2- (N, N-dimethylamino) Et 1 -2L4- (6-chloro-2-xinoxaliniloxio) phenoxypropionate (33, see Example 7) with methyl iodide. The resulting salt has a mp. 68 ° C.
    Example 9. Preparation of ethyl 2- 4- (6-chloro-2-quinoxalinylthio) phenoxy propionate (31).
    A. A solution of 4-mercaptophenol (10 mmol) in ethyl alcohol (IjO ml) is added in one portion to a solution of sodium ethylate (10 mmol) in ethyl alcohol (30 ml). After stirring the resulting reaction mixture, c. 10 mmol of 2,6-dichloroquinoxaline was added over 15 minutes and the reaction mixture was stirred for an additional 30 minutes. At the end of this time, the reaction mixture was diluted with water (500 ml), the crystalline precipitated at the same time was separated by filtration and dried, and 4- (6-chloro-2-quinoxalintio) -phenol was obtained, having a melting point of 204 C.
    B. The mixture of the thioester prepared as described in Part A, (1.0 g), ethyl 2-bromopropionate (0.6 g) and methyl ethyl ketone (30 ml) is heated under reflux for 8 hours. After cooling, the reaction mixture was filtered and the solvent was removed by distillation under reduced pressure, to obtain 2-4- (6-chloro-2-quinoxalinylthio) phenoxy3-propionate, mp. 110-115 C. The assumed structure of the obtained compound was confirmed by proton magnetic resonance spectroscopy and mass spectrometry.
    Example 10. Preparation of ethyl 2- 4- (6-chloro-4-hydroxyquinoxapin-2-yloxy) phenoxy propionate (39.
    A. Meta-chlorobenzoic acid (10.32 g of 90% active ingredient) is added portionwise over 40 minutes to a mixture of 2,6-dichloroquinoxapine (9.85 g) and methylene chloride (100 ml) while stirring and cooling. ice bath. Upon completion of the addition of chlorobenzoic acid, the reaction mixture is allowed to warm to room temperature and stirring is continued for another 4 days. Methylene chloride is added to the resulting suspension and then the reaction mixture is washed with a 5% aqueous solution of sodium bicarbonate (3x500 ml). The methylene chloride solution is dried with anhydrous sodium sulfate and the solvent is evaporated. The residue obtained is recrystallized from methyl alcohol, and 2,6-dichloroquinoxLIN-4-OXID (6.1 g; 57%) is obtained as a pale orange crystalline substance with a mp. } 76 ° C.
    B) 2,6-Dichloroquinoxaline-4-oxide is reacted with ethyl 2- (4-hydroxyphenoxy) propionate, following the same procedure as described in Example 2 B), ETS1-2-2- are obtained. (6-chloro-4-oxide-quinoxalin-2-yloxy) -phenoxy-propionate, having so pl. 105 C. The proposed structure of the compound was confirmed by proton magnetic resonance spectroscopy and mass spectrometry.
    Example 11. Preparation of ethn1-2-4- (6-amino-2-quinox-linyl-C) phenoxy-propionate (44).
    Ethyl 2-4- (6-nitro-2-quinoxalinyloxy) phenoxy-1-propionate (20 g, compound 21, prepared as described in Example 3) was dissolved in ethyl acetate (600 ml) and hydrogenated at room temperature and atmospheric pressure, using palladium on activated carbon as a catalyst. Upon completion of the hydrogen uptake, the solution is filtered through a pad of Celite (diatomaceous earth) and the solvent in the filtrate is removed by distillation under reduced pressure. The residue is chromatographed on a column filled with alumina No. 1 using cetylene chloride as the eluent. After evaporation of the solvent, ethyl 2-4- (6-amino-2-quinoxalinyloxy) phenoxy} propionate is obtained as a yellow crystalline substance.
    71
    having a mp 134 ° C. The proposed compound structure was confirmed by proton magnetic resonance spectroscopy and mass spectrometry.
    Example 12. Preparation of ethyl 2-4 GB- (dimethylamino) -2-quinoxalinyloxy-phenoxy-propionate (45).
    A mixture of ethyl 2-4- (fi-amino-2-quinoxalinoryloxy) phenoxy propionate (10 mmol), methyl iodide (25 mmol acetone (50 ml) and potassium carbonate (25 mmol)) is heated under refluxing conditions. within 24 hours. After that, the reaction mixture is filtered and the solvent is evaporated. The residue is chromatographed on a column filled with alumina using methylene chloride as the eluent, to give 2- {4- b- (dimethylamino) -2-hinsx linyloxy) -phenoxy-propionate as a yellow oil. The proposed compound structure was confirmed by proton magnetic resonance spectroscopy and mass spectrometry.
    Many of the proposed compounds are described in detail in table. 1 are crystalline substances and can be identified by their melting points (for convenience, the melting points of the compounds are tabulated and presented in Table 1).
    Some of the proposed compounds described in detail in Table 1 are oily substances and can be identified by their PCR spectra (for convenience, the proton magnetic resonance spectroscopy data is summarized in Table 2).
    Data illustrating the herbicidal activity of the compounds obtained by the proposed method are presented in the tables below. In tab. 3 and 4 — the degree of damage or damage caused to plants: is expressed on a scale with ratings from 0 to 3, with an estimate of 0 indicating the degree of damage to plants ranging from 0 to 25%, a rating of 3 expressing 75-99% plant death, and a rating of 3+ is used to indicate 100% mortality of the experimental plants. A dash (-) means that in this case the experiment was not conducted.
    The degree of damage to the experimental rats in Table 5 is estimated on a scale with ratings from 0 to 5, where a rating of 0 corresponds to 20% damage, while a rating of 5 means plant death.
    A dash (-) means that in the marked case the experiment was not conducted.
    Used in table. 5 abbreviated, the names of the experimental plants are interpreted as follows: Sb Sugar beet RP Radish Ct Cotton ZU Co Culturna Corn (maize) Ww Ozima wheat RC Rice
    Ot oats and wild oats
    Oats were used in pre-harvest processing experiments, and wild oats were used in post-soda treatment experiments.
    The abbreviated names of experimental plants are given in Table. 6 are interpreted as follows:
    Sy So kulturna (Pethal variety) Ct Cotton (Dalta Pine 16 Pn variety Peanut (peanuts, cultivar
    . Spanish red) Mg Corn (maize, variety XL 45) SS Setaria anceps Dg Digitaria Sanguinalis Sc Echinochloa crus-galli Sg Sorghum Goldrush Sh Sorghum halepense The activity of the proposed compound is shown in Table. 7
    The activity of one of the most well-known compounds is shown in Table. 8 The activity of another known compound is shown in Table. 9.
    A comparison of the activity of known compounds with the activity proposed clearly shows that the latter have a higher level of post-emergence herbicidal activity against monocotyledonous plants (see Tables 7, 8 and 9)
    1261564It)
    Table 1
    table 2
    11 8.7 singlet, 1G: 8.1 broad-1.7 ny singlet, 1H 7.7 wide-doublet, ny singlet, 2H; 7.1 multi-ZN plet, 4H8, 7 singlet, 1H; 6.9-7.7 multiplet, 7H (6- (CH |) j, N 3.0 singlet. 6H 8.7 singlet, 1H, 7.0-8.0 multiplet, 7H
    8.7 singlet, 1H {8.0 broad singlet, 1HJ
    7.6 multiplet, 2H; 7.2 multiplet, 4H
    8.8 singlet, 1H; 7.0-8.1 multiplet, 7H
    Pre-emergence herbicidal activity
    12
    261564 Continuation of table.2 4.9 1H 4.8 1N doublet, -, ЗН 4.81Н
    1.8 singlet,
    G
    4.4 quadruplet, ЗН 4Н; 1,3 triplet, 6H
     doublet, 4.7 quadruplet, 4.1 quadruplet, 3H 1H2H; 1.1 triplet, ZN
    Table 3 eats, 4.3 triplet 2H, 2.7 triplet, 2H, 2.3 singlet, 6H eats, 4.2 quadruplet, 2H, 1.2 triplet, ZN eats, 2.9 broad triplet, 2H 1.0 -1.8 multiplet, un
    Continuation of table 3
    15
    Post-harvest herbicidal activity
    sixteen
    1261564
    Table 4
    Continued table. four
    NOTE. Before - Pre-emergence processing.
    After - Prlevshodovaya processing.
    1 To 2.0 O 1 To 0.5 O 1 After 2.0 O
    Table 5 (Part B)
    Note, Pre-pre-emergence treatment.
    After - Toslevshodovaya treatment. 231261564 Pre-emergence; Field 24 Table (Part A) test
    25126156426 Post-harvest field trials Number of days after which {after the Erbicidal effect - Untreated control plots
    Table 6 (part B) processing was performed
    27126156428 Post-harvest field trials
    Table 6 (Part B)
    thirty,
    1261564
    Table 7 (Part A)
     SNS
    31
    32
    1261564 Table 8 (Part B)
    权利要求:
    Claims (2)
    [1]
    1. METHOD FOR PRODUCING CHINOXALINE DERIVATIVES of the general formula where A, B, D and E are hydrogen, halogen, nitro group, amino group, di-iC ^ -Cg-alkyl) -amino group, C (-C 6 ~ alkyl group and C <-C 6 haloalkyl group}
    J, U and V are hydrogen or halogen;
    R ( is hydrogen, C <-C 6 -alkyl groups and C | -C to -alkoxycarbonyl groups;
    R t is hydrogen and C, -C 6 alkyl groups;
    W-rpynna-c-g where
    G is a hydroxyl group, a C ^ -Cg alkoxy group, a Cj-Cg ~ alkenyloxy group, a C 2 ~ C 10 -alkyloxy group, a C (-C 6 -alkylthio group, a cyclohexyloxy group, a C 1 -C 6 alkoxy group substituted with a substituent from the group, including NN-di ~ (C, -C 6 -alkyl) -am-. Horpynny, N, N, N-TpH ~ (C ( -C & -alkyl) -ammonium group; or G-group of the formula —ONR 9, where R ^ is -C, -C 6 is an alkylidene group;
    or G - e OM group where M - alkali metal ion}
    X is oxygen
    J is oxygen or sulfur, | <and ϋ are 0 and 1; k +1 = 0 or 1, characterized in that the quinoxaline derivative of the formula
    Yuk
    E I (0k
    SU. " 1261564 AZ where Ζ is a halogen,
    A, B, D, E, J, k and have the indicated values, *
    are reacted with a compound of the general formula where R ( , R ^, Υ, X, U, V and I have the indicated meanings.
    [2]
    2. The method of pop. 1, characterized in that the process is carried out in the presence of an alkaline agent, namely an alkali metal carbonate.
    Priority by signs:
    17.07,79 A, B, D, E - hydrogen, halogen, nitro, amino, di- (C (C ^ alkyl) amino, C (-C 6 alkyl group, C (- C 6 group -galoidalkilnaya ;
    J is hydrogen;
    U, V is hydrogen and halogen;
    R ( is hydrogen, C, -C 6 -alkyl and C ( -C 6 -alkoxycarbonyl;
    R 2 is hydrogen and C, C 6 alkyl;
    About 0
    W is a -CG group, a G-hydroxy group, C ( -C ) o- alkoxy-C 2 -C 10 alkenyloxy, C 2 -C (0- alkyloxy, 0, C, o- alkylthio, cyclohexyloxy, OM, where M is an alkali metal ion;
    J is oxygen or sulfur;
    X is oxygen;
    k = 0 'e = o.
    04/11/80 J - halogen;
    GC, | -C lo alkoxy group substituted with a substituent from the group M, Y-di- (C, -C 6 -alkyl) amino, N, N, N-tph- (C, -C y -alkyl) -ammonium group, or ON-Rg, where R 0 is a (C | -C 6 ) -alkylidene group, k = 0, or 1,.
    C = 0 or 1, with k + 1 = 0 or 1.
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    法律状态:
    优先权:
    申请号 | 申请日 | 专利标题
    AUPD961779|1979-07-17|
    AUPE309380|1980-04-11|
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