• 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:
    Haloacyl 1-substituted-1,2,3,4-tetrahydroisoquinoline compounds are antidotes for thiocarbamate, triazine- type and acetamide herbicides. These antidote compounds are especially effective in safening acetamide herbicides used to control grassy and broadleaf weeds in corn.
    公开号:SU1505425A3
    申请号:SU864028720
    申请日:1986-12-30
    公开日:1989-08-30
    发明作者:Хорст Альт Герхард；Росс Хейкс Хэррисон；Джозеф Бринкер Роналд
    申请人:Монсанто Компани (Фирма)；
    IPC主号:
    专利说明:

    (21) 4028720 / 30-15
    (22) 12/30/86
    (31) 815101
    (32) ЗЫ2.85
    (33) US
    (46) 08/30/89. BKHP. Number 32
    (71) Monsanto Company (US)
    (72) Gerhard Horst Alt, Harrison Ross Hakes and Ronald Joseph Brinker (US)
    (53) 632.954 (088.8)
    (56) U.S. Patent Number, Class 71-118, 1980.
    (54) METHOD TO REDUCE HERBICID IMAGE OF MAIZE 2-CLOP-N- (ETOKCI-METHJT) -6-ETHYL-O-ACETOTOLUIDID
    (57) The invention relates to chemical plant protection products and can be used in crop production, in particular in the cultivation of corn. The purpose of the invention is to increase the efficiency of protection of maize against the damaging effects of the acetochlor herbicide. The method consists of using 2- (dichloradethyl) -1-methyl-1,2,3,4-tetrahydroisoicolin as a means of protecting maize from the damaging effects of acetochlor, at a dose of 0.11-0.67 kg / ha at a ratio of Herbicide - antidote (10-20): 1. The use of the indicated antidote in recommended doses provides suppression of weeds by 85-100% while reducing damage to corn to an economically acceptable degree - 12-15% in comparison with 20-30Z provided by the known anti-dots. 6 tab.
    ABOUT)
    The invention relates to chemical plant protection products and can be used in agriculture, in particular in plant growing.
    The purpose of the invention is to increase the effectiveness of protection.
    Many herbicides in quantities necessary to suppress the growth of weeds in crops of useful plants damage the latter, therefore, cannot be used to kill weeds in certain crops. However, the uncontrolled growth of weeds causes a decrease in crop yields and crop quality, since weeds compete with crops for light, water and
    and nutrients in the soil. It is possible to reduce the herbicidal damage to crops without an undesirable decrease in the herbicidal effect by applying the protective culture of the so-called herbicidal antidotes.
    The use of N-dichloro-acetyl-1,2,3,4-tetrahydroisoquinoline is known. As an antidote to protect maize with acetanilide herbicides.
    The 2-dichloroacetyl-1-methyl-1,2,3,4-tetrahydroisoquinoline, which is proposed as an antidote according to the invention, more effectively reduces the damage to corn by herbicide with acetochlor.
    The invention is illustrated by the following examples.
    SP
    about
    SP
    nU
    to
    SP

    cm
    3150
    Example 1. The method of obtaining
    2- (dichloroacetyl) -1-methyl-1,2,3,4-tetrahydraisoquinoline. Method A
    About C1
    II I C-CH-C1
    2- (Dichloroacetyl) -1-methyl-1,2,3,4-tetrahydroisoquinoline.
    0.1 mol of phenethylamine, 100 ml of methylene chloride and 50 ml of 10% sodium hydroxide are loaded into the reaction vessel. Then, 0.11 mol of acetyl chloride is added dropwise to the obtained reaction mass at room temperature. Water is introduced into the reaction vessel, after which the aqueous phase is separated from the organic. The latter is dried with magnesium sulfate and the solvent is distilled off, resulting in an intermediate containing amide. Phosphorus pentoxide and 100 ml of phosphorus oxychloride are added to it. Then the resulting mass is heated overnight at reflux temperature, after which it is poured onto ice. The ice mass is adjusted to an alkaline reaction with sodium hydroxide. The mass is then extracted with diethyl ether and the extract is dried with magnesium sulfate and the solvent is distilled off. The residue was distilled (62 ° C, 0.25 mm Hg) and 9 g of a yellow oil product were obtained, which according to the analysis contained 1-methyl-1,2,3,4 tetrahydroisoquinoline (yield 62% ). 9 g of a yellow product, 1.17 g of sodium borohydride and 80 ml of methanol are charged into the reaction vessel. The mass is heated for 3 hours at the temperature of reflux. 5 m of 10% sodium hydroxide and then 20 ml of water are then added with stirring to the mass. After that, methanol is distilled off from the mass and water is added, then the mass is extracted with methylene chloride. The extract is dried with magnesium sulfate, the solvent is distilled off and the residue is distilled to give 7.4 g of a yellow oil. 3 g of this yellow oil, 2.15 ml of dichloroacetyl chloride and 20 ml of toluene are charged to the reaction vessel. The reaction mass is heated for 1 hour at reflux temperature, after which it is cooled, the solvent is distilled off and subjected to distillation in a tube with a ball valve.
    0
    five
    0
    5 about 5
    0
    five
    0
    rhenium (0.01 mm Hg) to obtain 3 g of a yellow oil product.
    Calculated,%: C 55.83; H 5.08; N / C1 5.43.
    C, jH ,, Mass. 258.15,
    Found,%: C 55, 50; H 5.26; N / C1 5.21.
    Example 1. Method B. In the reaction vessel load 2723 ml of acetonitrile, which is kept under a layer of nitrogen. 1888.5 g of tin tetrachloride are gradually introduced into the vessel cooled with an ice-bath under the surface of acetonitrile over 2 hours and 20 minutes with stirring. During this period, the temperature of the reaction mass fluctuates within. Then the mass is settled overnight at room temperature. At a reaction temperature of 22 seconds, 916 g of 2-chloroethylbenzene was added in 10-minute portions to the reaction vessel in 10-minute portions. Then, 1369.7 g of acetonitrile is gradually distilled off from the mass, keeping it under reduced pressure and heating it. During this operation, the temperature of the mass fluctuates between 23-84 ° C, and the pressure in the vessel ranges between 45-100 mm Hg. The reaction mass, having a milky color, is heated to the reflux temperature, at which it is kept for 6.5 hours. The temperature of the mass during this operation varies between 109-113 ° C. When the temperature of the mass is 75 ° C, all the amount of acetonitrile that was previously distilled off is added to the mass. The mass is cooled and settled overnight, after which it is determined by inspection that it contains suspended particles. Then 2 l of methylene chloride is added to the mass. Then, with stirring, this mass is added to 4 ml of pre-cooled to a temperature of 10% sodium hydroxide. The temperature of the mass increases to 40 ° C and shows an acid reaction. In order to bring it to alkaline, another 13 liters of 10% sodium hydroxide is added.
    The organic phase is then separated and washed with water. The organic phase is dried with sodium sulfate, filtered and distilled in a rotary evaporator at 35-40 ° C, resulting in 749.3 g of 1-methyl-3,4-dihydroisoquinoline (yield 79.2%, sch 51505
    that on 2-chloroethylbeneolum initial material. al). A suspension of 300 g of palladium on coal moistened with 50% 5% catalyst in 8 ml of absolute ethanol is loaded into the autoclave. Then a mixture of 2143.2 g of 1-methyl-3,4-dihydroisoquinoline and 82.2 g of a contaminant — 2-chloroethylbenzene (like the mixture obtained by the previous method) is added to the suspension. The autoclave is washed with hydrogen gas. With stirring of the reaction mass in an autoclave using hydrogen, the pressure is gradually increased for 2 hours to a final value of about 12.6 x 10 Pa and the temperature reaches 50 ° C. Under these conditions, the autoclave is kept overnight. After aeration of the autoclave with stirring of the reaction mass, the temperature of the autoclave drops to 9 ° C. The mass is filtered off, and then ethanol is distilled off to obtain 2100.0 g of 1-methyl-1,2,3,4 tetrahydroisochlnoline (96, 7% per l-methyl-3, 4-dihydroisoquinolin-Doro starting material). I load a mixture of 1136 g of 1-methyl - 1, 2.3, 4 tetras into a reaction vessel; hydroisoquinoline in 1360 ml of toluene. The mass is cooled to, after it is mixed and placed under a layer 13 of. At a mixture temperature of 10 ° C, 150 ml of dichloroacetyl chloride are gradually added over 13 minutes. At the end of this operation, the temperature of the mass is 70 ° C. Then, over 2 hours, 780 ml of dichloroacetyl chloride and 2100 ml of toluene are gradually added in separate portions. Then, the reaction mass is heated for 2.5 hours at a temperature of reflux, the hydrochloric gas is evolved, and then the mass is cooled and 100 g of silica gel is added. After that, the mass is filtered off, then the toluene and excess dichloroacetyl chloride are distilled to obtain 1801 , 5 g of 2- (dichloroacetyl) -1 -methyl-1, 2,3,4-tetrahydride, ro-isoquinoline (yield 97.7%, based on 1-methyl-1,2,3,4- tetrahydroisoquinol1 material).
    Biological evaluation. By treating a plant's habitat with a combination of a herbicidal compound and an antidote, weed is effectively destroyed with low damage to a given culture. Plant habitat is the environment in which
    ,,
    JQ) 5 7Q
    / 25
    thirty
    40
    45
    55
    plants, such as soil, as well as seeds, seedlings, roots, stems, leaves, or other parts of plants, germinate. The expression combination of a herbicidal compound and antidote refers to a number of processing methods. Thus, the soil on which crop plants should germinate can be treated with the composition, or separately, with compounds of a herbicide and an antidote, so that the combination in this case takes place on the soil or in the soil. After tillage, applying a mixture of rbicide and an antidote, or using a separate or sequential application of a herbicide and antidote, applies a herbicide and antidote to the soil by mechanical agitation of the soil using agricultural implements or rainwater or irrigation. In addition, the soil can be treated with an antidote using it in the form of an emulsifiable concentrate, for example granulate. Pellets are applied to the first furrow prepared for seed treatment, and herbicides are applied to the plants' habitat before or after placing the pellet that contains the antidote in the furrow, so that the herbicide and antidote form a combination. The seeds of a cultivated plant are treated or covered with an anthadot either in the furrow immediately after their digging or before they are sown in the furrow, preferably the latter. A herbicide is applied to the soil of a plant's habitat before or after sowing, and a combination is formed when both the herbicide and antidote-coated seeds are in the soil.
    Lmtidot can be applied to the culture habitat in a mixture with the selected herbicide. Thus, after sowing the appropriate culture, a suitable mixture of antidote and herbicide is applied to the soil surface or to the latter either in the form of a homogeneous liquid emulsion or suspension, or in solid form successively. It is also possible to apply the mixture to the soil and then seed into the soil under the soil layer containing a mixture of the herbicide and anti-electrode. The action of the herbicide reduces the number of unwanted weeds or completely eliminates them. At the same time, the presence of an antidote reduces or eliminates possible damage to seeds or seedlings.
    cultivated plants caused by herbicide.
    The proposed antidote compound reduces herbicidal damage in sorghum, wheat, rice, soybean, and corn, which are associated with end-use herbicides.
    The compounds are effective in reducing damage to maize, caused by acetamide herbicides — acetochlor (2-chloro-H- (ethoxymethyl) -b-ethyl-o-acetotoluidide) and 2-chloro-2-methyl-b-methoxy-K- (isopropoxymethyl ) acetanilide, which are active acetanilide herbicides.
    Acetochlor, as well as the known alachlor, is suitable for the destruction in corn crops of a large number of grassy and broad-leaved series. The combination of antidotes of the general formula and acetochlor represents a number of advantages over alachlor in the suppression of grass and broad-leaved weeds growing in maize crops difficult to destroy. Thus, using such combinations of antidote and acetochlor, such broadleaf weeds, such as limnocharis, ipome and common purslane, as well as grassy weeds, are effectively destroyed, while alachlor has only a short suppressive effect on these broadleaf weeds. The antidote of the general formula reduces the damage caused by acetochlor to corn, and without worsening the herbicidal effect of acetochlor on corn. Along with the destruction of broadleaf weeds, acetochlo has a higher single activity, a lower consumption rate in most soils, and a higher activity in soils with a high content of organic substances. The consumption rate of acetochlor with an equal degree of weed control is about two times lower than that of alachlor, which provides a significant reduction in environmental load. Herbicide The use of an antidote in combination with acetochlor makes it possible to use the advantages of acetochlor to increase the production of corn at reduced costs per unit area.
    Example 2. Interaction of the herbicide with the antidote when used as a mixture until the appearance

    0 5 o
    five
    five
    seedlings of cultivated and weeds. The vessels were filled with fumigated, silty-loamy soil and tightly squeezed the last to a depth of 1.3 cm from the edge of the vessel. The first vessel was intended for testing untreated plants, the second for testing plants treated with a herbicide, and the third for testing plants treated with a herbicide and antidote.
    In each vessel were sown seeds of cultivated and weed plants. A mixture of herbicide and antidote was applied to seeded vessels either by covering it with a layer of soil placed on the seed bed, followed by irrigation to inject the mixture into the soil, or by depositing a predetermined amount of the mixture into the soil, followed by placing the treated soil on the seed bed in the vessel. The vessels were then placed on the greenhouse shelving and for the entire test period they were irrigated from the bottom with the necessary amount of water. Approximately three weeks after the treatment, the reaction of the plants was recorded.
    The results are shown in Table. 1. (herbicide 5 - acetochlor, antidote - according to example 1).
    Example Z. In order to determine the relative inhibition of a grassy weed of a foxtail germinating in maize culture, acetochlor (herbicidal compound 5) and acetochlor mixed in a tank with an antidote compound 1 were applied to adjacent field areas. The sections were treated with pre-emergence (PRE) and pre-seed (PPI) methods. Experimental sites were prepared from heavy silty loam containing A% of organic matter. Prepared test drugs based on acetochlor alone, a mixture of acetochlor and an antidote and a control antidote in the absence of a herbicide were sprayed on the plots based on a rate of 280 l / ha.
    The test results are shown in Table. 2
    The field conditions during site processing are as follows:
    wind speed 16-A8 km / h, windy weather,
    air temperature of 22 ° C
    soil temperature 18 ° C,
    Soil moisture content: dry on the surface, moist at the depth of sowing of seeds.
    The amount of precipitation (irrigation): the first significant precipitation of 0.6 cm on the day of treatment, precipitation (in the first 3 weeks) 4.95 cm, irrigation was absent.
    In order to establish the protective effect of the known antidote compound and the proposed antidote to maize against the action of acetochlor, used to suppress weeds, the acetochlor-containing preparations obtained by mixing in a tank were compared in field conditions with preparations based on acetochlor and antidote, and the following antidotes:
    About C1 fc-CH-Cl
    C1-SI-C1
     proposed connection) PRI m e I
    (known compound 22 4, In order to determine the relative inhibition of broadleaf weeds, ipomoea and garden purslane, germinating in maize crops, acetochlor (herbicidal compound 5) and prepared by mixing in a tank of ace Toxjjopa mixture with different antidotes were applied to adjacent field sites (Compounds 1 and 22). Plots were treated with pre-emergence (PRE) and pre-sowing (PPI) methods. Experimental plots were prepared from sludge loam containing approximately 1% of organic matter. s based on one acetochlor, mixtures of acetochlor and safener and the control formulation on the basis of the absence of the antidote in the herbicide was sprayed on corresponding portions in steii to Example 3.
    Field conditions during the processing of the plots. The following: wind speed of 8-16 km / h, air temperature of 23 C, soil temperature of 23 ° C.
    Soil moisture content: dry on the surface, moist at a depth of seeding of seeds.
     Rainfall (irrigation): first significant sieges 10
    20

    542510
    ki 2.16 cm after 4 days. after processing, precipitation (for the first 3 weeks) 16.2 cm, irrigation 2.5 cm after 2 days. after processing.
    Inhibition of plant growth by acetochlor and its mixtures with acetochlor is given in Table. 3
    Example 5. In order to determine the relative inhibition of a broadleaf weed of Carnimocharis germinating in maize crops, acetochlor (herbicidal compound 5) was applied to adjacent field sites.
    15 and. Prepared by mixing in the tank mixtures of acetochlor with different antidotes (compounds 1 and 22). The plots were treated with pre-emergence (PRE) and pre-sowing (PPI) methods. Experimental sites were prepared from silt loam with an organic matter content of -1%. Prepared test drugs based on acetochlor alone, a mixture of acetochlor and an antidote and a control antidote in the absence of a herbicide were sprayed in areas in accordance with Example 3.
    The test results are shown in Table. four.
    30 Field conditions during the processing of the plots: wind speed 0-8 km / h, air temperature 25.5 ° С, soil temperature 25.5 С,
    Soil moisture content: dry on
    - the surface is wet at the depth of seeding.
    The amount of precipitation (irrigation): the first significant precipitation is 1.63 cm after 8 days after treatment 4Q, precipitation (for the first 3 weeks) is 18.9 cm, and irrigation is 2.5 cm after 2 days after treatment.
    The inhibition of plant growth with acetochlor and its mixtures with antidotes is given in Table. four.
    25
    45
    0
    five
    The results of the comparative tests show that the proposed compound — an antidote (compound 1) with respect to protection against acetochlor in corn crops — significantly exceeds the known compound — an antidote (compound 22).
    In tab. Figures 5 and 6 show the results of damage to corn according to examples 4 and 5, obtained at two different sites.
    The averaged protective effects for pre-emergence and presowing treatments are given. These average protective effects were used to determine the relative efficacy of these two antidotes by dividing the protective effect of the proposed antidote (compound 1) by the protective effect of the known antidote (compound No. 22).
    The proposed compound exhibited efficacy exceeding the efficacy of the known compounds by a factor of 1.4–6.4, depending on the consumption rate of the mixture of acetochlor and antidote.
    The averaged data of the two experimental plots show that the proposed compound is twice as effective as the known antidote.
    The data presented on damage to maize and weed are related to the combination of the most economically advantageous conditions and therefore this combination of the most economically advantageous conditions includes the minimum consumption rate of acetochlor (2.24 kg / ha), the minimum consumption rate of the antidote (0.11 kg / ha) and the simplest procedure for the treatment of fields (the preliminary application of a preparation containing a herbicide and an antidote to the mixture, which is prepared by mixing in a tank). In addition, the economic acceptability of the treatment of a herbicide with a product depends on two other criteria. First, the herbicidal
    4.4810.14
    4.4810.14
    4.4810.14
    4.4810.14
    4.4810.14
    4,481 0,14
    About 55
    (100) 5 68
    (92) 35 73
    (52) About 20
    (100) 20 88
    (77)
    70 75 (6)
    the product should suppress the growth of inhibited weeds, in particular broad-leaved weeds, by no less than 85%; secondly, maize damage caused by the herbicide product must be less than 20%. Treatment of plants with an antidote-free acetochloric preparation leads to excessive maize damage (28% and 20%) or does not inhibit weed germination. Acetochloric drug containing a known antidote (compound 22) causes excessive damage (23% and 30%) of corn. An adhetochloric preparation containing the proposed antidote (compound 1) provides both an economically acceptable suppression of broadleaf weeds and an economically acceptable degree of damage to corn (12 and 15%).
    权利要求:
    Claims (1)
    [1]
    Invention Formula
    A method of reducing the herbicidal damage of maize with 2-chloro-N- (ethoxy-methyl) -6-eth1-o-acetotoluidide, which includes the use of an antidote, characterized in that, in order to increase the effectiveness of protection, 2- (dichloroacetyl) is used as an antidote 1-methyl-1,2, 3,4-tetrahydroisoquinoline at a dose of 0.1 g 0.67 kg / ha with a mass ratio of herbicide - antidote 10-20: 1.
    Table 1
    100
    (0) 100
    (0) 100
    (0) 100
    (0) 100
    (0) 100
    (0)
    100 100 100
    1аа
    100 100
    (0) (0) (0) (0) (0)
    (0)
    100
    100
    100
    98
    100
    100
    100
    100
    100
    100
    100
    100
    100
    100
    100
    10D
    100
    100
    100
    100
    100
    100
    100
    100
    100
    100
    Note,
    a - data obtained 23 days after processing, b - data obtained 58 days after processing.
    Continued gab. I
    Note as
    b
    data obtained 19 days after processing, data obtained 29 days after processing.
    Table 4
    OO herbicide 5
    2.24O
    4,48О
    6.72O
    herbicide 5 antidote 1
    2,240.11
    4.480.22
    PRE / PPI O
    28/37 58/63 78/82
    17/10 27/20
    Table 3

    PRE / PPI
    PRE / PPI
    Note, a- data g -chucheny 21 days after treatment,
    b - data obtained 35 days after processing.
    Data received after 29 days. after processing. W - herbicide + antidote, WO - herbicide,
    The effect of the proposed compound 1 is divided by the protective effect of the known compound 22; The average Dacex antagonization of protective effects is 2.4.
    Table 5
    The data were obtained 35 days after the processing. The most effective effect of the proposed compound is 1 divided by 1H (h (nor all of the equivalent effective effects of 1.7.
    Tables b
    the protective effect of non-compound 22; the average
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    法律状态:
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