前苏联专利SU906347A3 Antidote herbicidal composition

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专利摘要:
N-(substituted benzenesulfonyl) carbamates as new compositions of matter useful as active herbicidal antidotes to protect against and decrease crop injury when used with a thiocarbamate herbicide when applied in various methods; improved herbicidal compositions and utility of said compositions to protect against and decrease phytotoxic crop injury when employing thiocarbamate herbicides and a two-part herbicide system comprising a first-part of one or more thiocarbamate herbicide and a second part of an effective antidote therefor compound said antidote compounds of the class N-benzene sulfonyl carbamates having the formula <IMAGE> wherein X is hydrogen, bromo, chloro, methoxy, trifluoromethyl, and methyl; n is an integer from 1 to 3 inclusive, provided that when X is bromo, trifluoromethyl, or methoxy, n is 1; and R is selected from alkyl, haloalkyl wherein halo is chloro or fluoro, alkenyl, haloalkenyl and wherein halo is chloro, alkynyl, trifluoroacetamidomethyl, dialkylamino cyanoalkylthioalkyl, phosphonomethyl, lower alkyl substituted phenyl, 4-chlorophenylthiomethyl, alkoxyalkyl, alkylthioalkyl, cyanoalkyl, alkoxycarbonylalkyl, formamidoalkyl, alkoxycarbonylalkenyl, alkylcarbonylalkyl, 1,3-dioxacyclohexane-5,5-methylene, phenyl, chlorophenyl, benzyl, 4-chlorobenzyl, 4-methoxybenzyl, 3-pyridylmethyl, phenoxyethyl, 3-phenylpropyn-2-yl, methylthioacetimino, acetone imino and benzaldimino.
公开号:SU906347A3
申请号:SU762421606
申请日:1976-11-11
公开日:1982-02-15
发明作者:Маркус Паллос Ференц；Джеремиах Гаугхан Эдмунд
申请人:Стауффер Кемикал Компани (Фирма)；
IPC主号:

专利说明:

(54) ANTIDOTIC HERBICID COMPOSITION
one
This invention relates to chemical means of controlling undesirable vegetation, namely, an antidote herbicide composition based on a herbicide and an antidote.
Known thiocarbamate herbicides of the General formula
Qn
ah 1
j.N-CQ-SR,
where is ethyl,
propyl-;
RIJ is ethyl, propyl, isobutyl; R - propyl, butyl, cyclohexyl
or Vli RS-together form hexamethylene P.
However, they are phytotoxic with respect to some cultivated plants.
An antidotal herbicidal composition containing a thiocarbamate herbicide and an antidote, 2-bromoethyl ethanesulfonate 2J, is known.
However, it serves to protect the maize from thiocarbamate herbicides.
The purpose of the invention is to find such an antidote herbicidal composition, which has a reduced toxicity of the herbicide on cultivated plants, based on a thiocarbamate HHO herbicide and antidote.
This goal is achieved using an antidote herbicidal composition containing, as a herbicide, thiocarbamate derivatives of the general formula.
N - COSR
Ig
where R is ethyl, propyl
Rf, - ethyl, propyl, isobutyl {R - propyl, butyl, cyclohexyl
or
Rn and Ra-together form hexamethylene. as antidote M- (benzenesul (Leonyl) carbama.t of the general formula ITO. -i rS-oB where X is hydrogen, bromine, chlorine, methokei., trifluoromethyl, methyl, an integer of 1-3 (provided that X-bromo , trifluoromethyl or methoxy, yl 1) j alkyl, haloalkyl, where the halogen is bromine, chlorine, fluorine in the amount of 1, 6, alkenyl, 2 chloroallyl, alkyloyl C-C, diethylamino, phosphonomethyl, phenyl, substituted by methyl, propyl, butyl once, twice or three times, 4-chlorophenylthiomethyl ethoxy; cyanisopropyl, formamidoethyl ethoxycarbonylmethyl, ethoxy, carbonylethyl, 1-ethoxycarbonylpro Enyl- (1,2), methylcarbano-nylethyl, 1,3-dioxycyclohexan san-5.5 methylmethylene, phenyl, phenyl, substituted by chlorine once, twice, four times, benzyl, 4.-chloro-benzyl 4-methoxybenzyl, 3 pyridylmethyl, phenoxymethyl, Cphenylpro pimyl-2, benzaldimino, acetonimino, methylthioacetimino, trifluoroacetylamidomethyl cyanoethylthioethylene, with a weight ratio of antidote: herbicide (0.01-6.1): 1. corresponding alkynol with benzenesulfonyl isocyanate. The reaction is carried out in the presence of a solvent such as benzene or chloroform, in the presence of catalytic amounts of triethylamine and dibutyl tin dilaurate. In some cases, catalyst n is required. After the reaction is complete, the product is separated by filtration or by evaporation of the solvent. If necessary, the product can be recrystallized from a suitable solvent. The method for the preparation of N-benzenesulfon NILE alkyl carbamates. The reaction of the corresponding benzenesulfonamide with alkyl chloroformate in the presence of a catalyst such as potassium carbonate. Usually, a solvent is used to accelerate the reaction and to improve the processing of the product. After filtration, extraction and drying, the product can be purified by treatment with hexane or by recrystallization from a suitable solvent. In most cases, the structure is confirmed by IR spectroscopy, nuclear magnetic resonance, or mass spectroscopy. Example 1. The preparation of 2-butyl-1-yl-p-toluensulfonyl carbamate. To a solution of 1.75 g (0.025 mol) of 2-butyn-1-ol in 25 ml of chloroform, k, ø g (0.025 mol) of p-toluenesulfonyl isocyanate is slowly added. An ecothermal reaction occurs. The product is isolated by evaporation of the solvent. B, the result is 6, g of the compound. C. 85-90C. Example 2. Preparation of 2-bromopropyl-p-toluenesulfonyl carbamate. By the method as in Example 1, between 3, g (0.025 mol) of 2-bromo-1-propanol and 25 ml of chloroform and 4.9 g (0.025 mol) of p-toluenesulfonyl isocyanate are reacted. After a similar treatment to remove the solvent, 8, k2 g of the title compound, p 1.5375, are obtained. PRI me R 3. Getting hexafluoroisopropyl-p-toluensulfonyl carbamate. By the method, analogously to Example 1, 4.2 g of sim-hexafluoroisopropanol in 25 ml of chloroform and 9 g (0.025 mol) of toluenesulfonyl isocyanate react with two drops of triethylamine as a catalyst. After a similar treatment to remove the solvent, 8.9 g of compound are obtained, m.p. b9-75 ° C. Example 4. Preparation of H- (p-chlorobenzenesulfonyl) -propargyl carbamate. To a solution of 1.7 g (0.03 mol) of propargyl alcohol in 20 ml of benzene containing one drop of triethylamine; and one drop of dibutyl tin of dilaurate, add a solution of 6.5 g (0.03 mol) of p-chlorobenzenesulfonyl isocyanate in 25 ml of benzene. The reaction is exothermic and the temperature rises to 30 ° C. The mixture is stirred for several hours at room temperature and the precipitated solid is filtered and washed with a small amount of hexane and dried. 590 8.0 g (yield; 98 from the theory) are obtained: 106-108 C. Chisgo compounds, m.p. This sample melts at 120.5-12lC. The structure of the compound is confirmed by IR spectroscopy, nuclear magnetic resonance and mass spectroscopy. Example 5- Preparation of N- (n-chlorobenzenesulfonyl) -ethyl carbamate. 6.1 g (6.032 mol) of p-chlorobenzenesul: phonamide, 10.8 g (0.078 mol) of potassium carbonate and g (0.03t mol) of ethyl chloroformate in ml of acetone are stirred and boiled under reflux for two hours. During heating, the mixture becomes viscous and is diluted with 30 ml of acetone. The cooled mixture is poured into 150 ml of water and filtered through zeolite. The filtrate is acidified with hydrochloric acid while cooling (pH 2) and the product is extracted with benzene. The extract is washed with water and dried over anhydrous rV
Table T V6 magnesium sulphate. Removal of the solvent gives the compound as a solid. In the amount of 5.5 g (yield 65% of theory), so pl. 85-90 0. The structure of this compound is confirmed by IR spectroscopy. Example 6. Obtaining N- (n. -Methoxybenzenesulfonyl) -ethyl carba-. Mata. 5.0 g (0.032 mol; p-methoxybene (. solsulfonamide, 10.8 g (0.078 mol) of potassium carbonate and 3.7 g (0.03 mol) of ethyl chloroformate) in tO ml of acetone is boiled with reverse refrigerator for 2.5 hours, the Product is treated analogously to Example 5. The yield of the compound is 3.9 g 47 from theory), mp 110-116 ° C. Table 1 shows the compounds that were prepared in accordance with the indicated methods Compounds are given numbers that are used for identification. BUT lu -5-eR
k-z
-CHj 4-CH3 4-CH,
Viscous substance
110 MB
85-90
69-75
one,
one,
1.3375 w
ten
. E0 (Continuation of table. 1
13
CHnCH CHft
W-Wed
CH
s-erz
Wwl
Cahs
2-CF
3-C1
CHftCFj 3-C1
CHftCH E CHft 3-C1
t CH 3-C1
CH, C CCH 3-C1
2, i.6-CH3
2, it, 6-CH3
iso-SchN-, 2, it, 6-CH3
CHrjCF
2, i, 6-CH
2,, 6-СНз
E CH
2Л, 6-СНэ 2,4,6-СНз it-CHj it-CHj
906347
1 Continued table. one
(phenyl)
addition) -N-CH
The structure of the compound is confirmed by either IR spectroscopy or nuclear magnetic resonance. Forms of the use of drugs conventional Methods and method of evaluation. The boxes used to germinate neither crops and varieties of weeds are filled with sandy soil. Basic solutions of the herbicide and each test antidote are prepared as follows. A. Herbicide - - n-propyl-M, N-di-n-propylthiocarbamate - correct 6E15bO mg. Vernam-BE is diluted in 250 ml of water, so 5 ml of the solution used in the box is equivalent to 6 lb / acr (6.9 kg / ha per box surface area). V.Antidot - for each of the tested substances, 78 mg is dissolved in 20 ml of acetone, in which% tween is present. - 20 (polyoxyethylene sorbitan monolaurate, so that 5 ml of the solution, when applied according to the method of administration before sowing (PRR), corresponds to A 5 pound / acre of Atsik (5.7 kg / ha), Herbicide and antidotes are applied on the soil together, as a mixture in a tank, according to the method of administration before sowing. To prepare the combined mixture on a rotary mixer, add 5 ml of Vernama with the subsequent introduction of this amount into the soil from the shchikov. One row of each of the above crops and weeds is sown in the boxes: Watergrass (Echinochloa crusgalli), Foxtail (Setaria viridis) and Stock (Glycine max) .The boxes are placed in greenhouse tanks in which the temperature is maintained at 70-90 ° F ( 22-33 ° C.) The soil is moistened with a small amount of water in order to facilitate
good plant growth. Damage assessment is carried out two and four weeks after application. The assessment includes individual boxes treated with a single herbicide 5 to provide a basis for calculating the amount of damage reduction caused by the action of the herbicidal antidotes.
Test results are presented
in tab. 2. The protective effect is determined by comparison with boxes that have not been treated with the antidotes of the invention.
Method of application: introduction before sowing -PPJ (mixing tank). Culturna variety: co (Glycine max), weed species: foxtail (Setaria virtdis), Watergrass (Echinochloa crusgalli),
Table z
21 - Damage percentage. - Percentage of protective effect. a - Introduction of vernama and antidote before separately
22
S1 Continued ab. 2 sowing, carried out 2390 Seed treatment test. Small crates are filled with Felton's sandy soil. At the same time, herbicides introduced into the soil are used. The soil from each bin is placed in a five-gallon (18.8 L) cement mixer, where the soil is mixed as the herbicides are introduced using a predetermined amount of the basic solution containing 780 mg of 75 5% active ingredient in 125 ml of water . Using a voltmetric pipette, 5 ml of a stock solution containing the equivalent of a herbicide corresponding to 6 pounds / acre (6.9 kg / ha) are applied to the soil when applied to the soil in boxes. After the introduction of the herbicide, the soil is placed back into the crate. After that, shchi cells with no4Bovi, treated and untreated with a herbicide, are ready for sowing. Soil samples in an amount equal to 1 pint (0.5 liter) are taken from each crate and placed back for further use in seed coverings. The soil is leveled and made 1/2 inch deep (1.27 cm) for sowing seeds. Other rows of cultivated and untreated seeds are also sown. In each experiment, soybean seeds (GJycine s) are sown in each row. Pins are made 1-1 / 2 inches (2,, 27 cm) apart. The seeds are treated with a prepared basic solution, which is obtained by dissolving 250 mg of the antidote compound in 2.5 ml of acetone, then using 0.5 ml of the basic solution to treat 10 g of soybean seeds, which is equivalent to 0.5 weight, ° C; can also be used in the form of slurries, powders and dusters. In some cases, acetone is used to dissolve powdered or solid compounds so that they can be used on seeds with greater efficiency. After they are planted as seeds, the seeds are covered with one pint (0.5 liter) of soil, which will be removed just before planting. The boxes are placed in greenhouse tanks in which the temperature is maintained at 70-79 ° 1 (22-24 ° C). The boxes are moistened with a small amount of plant growth. The control water for the percentage assessment is done four weeks after the treatment. In each experiment, a herbicide or herbicide is used together with the substance to protect the seeds, or only such a substance, to determine phototoxicity. Untreated adjacent row is used to observe the beneficial lateral movement of the antidote compound through the soil. The extent of this effect is noted in comparison with the control experiment. When treating seeds with the herbicide 5-n-propyl-N, N-di-n-propylthiocarbamate, compound 17 demonstrates the protection of the treated soybean seeds, i.e. damage is reduced by 50% for germinated soybean plants that have grown from seeds treated with compound 17, compared to untreated seeds grown on soil containing a thiocarbonate herbicide. Method and method of evaluation. Boxes that are used for the growth of crops and weeds of varieties are filled with sandy sand. Various methods of use are used, such as administering a herbicide and an antidote separately before sowing, or as a reservoir mixture from a herbicide and antidote. Seeds are sown on soil treated with an effective herbicidal composition of a thiocarbamate herbicide and an antidote, applied to the treatment in the groove of the seed and the surrounding soil with a herbicide. The crop is then processed. seeds with an antidote before sowing onto the soil treated with a herbicide. Basic solutions of thiocarbonate herbicides and tested antidotes are prepared as follows. Herbicides, C.5-ethyl-M, N-di-n-propylthiocarbamate-EPTC-eptam 6E-260 mg, are dissolved in 200 ml of water ml, applied on the soil from the seed box, equivalent to 1 pound / acre (, 1, 1 kg / ha applied in 80 gallons (5 liters of water) per acre, and 3 ml is equivalent to 0.75 lb / acre (0.86 kg / ha). OZ-isoprrpI L-M- (-methyl-5- ethylenethylenyl-thiococabmamate (P-12001), 390 mg is dissolved in 200 ml of acetone in the presence of U tween 20, or 975 ml is dissolved in 250 ml of acetone, so that 5 ml of the solution applied to the sowing bottle is equivalent to 2 pounds / acre (2, 228 kg / ha) when administered before sowing, and 6 ml is equivalent to b pounds / acre (6.9 kg / ha) respectively. ES-ethyl-N, N-di-isobutylthiocarba matane 6E or $, M-diethyl-M-cyclohexylthiocarbamate ronite 6E-520 mg is dissolved in 200 ml of water so that k ml of solution, applied to a sowing crate, equivalent to 2 lb / acre (2,228. kg / ha) when used in 80 gallons of water (5 l) per acre. For consumption rates of 6 lb / aa (6.9 kg / ha) or 12 lb / acre U3.8 kg / 1300 mg or 26 mg solution in 250 m of water so that 6 ml of this solution is equivalent to the desired amount, F.5- (2,3,3-trichloroallyl) -M.M- . : -Iiisopropylthiocarbamate-avadex CP -1219 mg is dissolved in 300 ml of water so that 6 ml of solution is equivalent to a consumption rate of 3 pounds / acre (3, kg / g when used on the soil from the box after the installation method before planting). C.5-ethyl-L-hexamethylenothiocarbam order 8E-857 mg is dissolved in 250 ml of water so that 5 ml of solution is equivalent to the consumption rate of i lb / acre, 6 kg / ha), and 2.5 ml of this solution equivalent to a consumption rate of 2 lb / acre (2.23 kg / ha), when applied to a crate planter, sown according to the method of administration before sowing. Antidotes H. For each of the antidotes tested, 250 mg of the active ingredient is dissolved in 2.5 ml of acetone in the presence of 1 Tween 20 (polyoxyethylene sorbitan monolaurate) so that 0.5 ml of this solution per 10 g of seed is equivalent to 1 w / w. For seed treatment with a norm of 0.25 ml, 0.25 ml of acetone is diluted so that 0.5 ml of this solution per 10 g of seeds is equivalent to 1 / wt.% / Ve. This solution is used to treat the seeds with different amounts and at different dilutions, for example: for 0.10%, 0.1 ml is diluted with 0 ml of acetone. 3. For each test compound used in the groove, 95 mg of the active ingredient is diluted in 15 ml of acetone in the presence of% Tween 20 so that 1.5 ml of the solution applied on the seeds and soil in the groove equivalent to a consumption rate of 5 lb / acre (5.7 kg / ha). At a rate of 9 26, flow rate 1.0 lb / acre (I, kg / ha), 0.3 ml is diluted with 1.2 ml acetone. J. For each of the test compounds used in the introduction test, before seeding the reservoir mixture, 39 mg of the active ingredient is dissolved in 10 ml of acetone in the presence of 1% Tween 20 so that 5 ml of the solution. at 5 lb / acre (5.7 kg / ha). When applying the antidote in the groove using these basic solutions. At the preparation stage, a sample of SOIL in an amount equal to one pint (0.53 l) is taken from each storage box for storage and is then used to coat the seeds after treatment with basic solutions. Before planting, the soil is leveled, herbicidal base solutions are applied in individual boxes and entered into the soil from a seeded crate before sowing, with an equivalent consumption rate of 1 lb / acre (kg / ha) of the active ingredient OR with a specified consumption rate, respectively. In each of the treated boxes, longitudinal rows of 1 / inch (0.64 cm) depth are made, as preparation before sowing. After sowing, the boxes are divided into two equal parts with the help of a wooden partition, and 1-1.2 ml of the basic solution 1 is sprayed directly onto the seeds and soil in the open groove in one half of the box. The unprocessed part of the crate is left to check the effect of the herbicide, as well as to observe the lateral movement of the antidote through the soil. Seeds are covered with a sample of untreated soil equal to one pint (0.58 L), which is removed in advance. For tank mixes, which are used by the method of administration before seeding, the following solutions and methods are used. 5 ml of the herbicidal basic solution A or C is mixed with 5 ml of the test antidote solution, so that the equivalent with the consumption rate of L lb / acre (1.11 kg / ha) and 5 Pound / acre ($ | 7 kg / ha) of the herbicide and the antidote is respectively injected into the soil of each crate. For administration before sowing. the mixed base solutions are injected into the soil during the introduction in a 5 gallon (18.8 L) rotary mixer. Other basic solutions are used with the indicated norms of stroke 2790 in a method using a tank mixture. For processing, 10 g of seeds in a suitable tank are shaken with 0.5 m of an antidote stock solution H, or another basic solution so that the treatment of seeds with equivalent G is 0.5 wt%, w / w, 0.25 wtL / wt, 0.125 weight D / weight or Q,% D / D weight. Shaking is continued until the seeds are uniformly coated. Antidote compounds can be used in the form of liquid slimes, powder or dust. The treated seeds are sown in a soil in which a herbicidal stock solution is injected before sowing, with a consumption rate equivalent to 1 pound / acre (1.11t kg / ha) of the active ingredient. All boxes are placed in greenhouse tanks, the temperature of the B temperature was maintained in the range of 70-90 ° F (2233 ° C). The soil is moistened with a few drops of water for good plant growth. Damage assessed by PPPI
Ordram
PFI
Ronit
PP1
Ronit
PPI
Ordram
PPI
Ronit
PPI
Vernam
ST
Ordram
60/90
CN 85/95
CN
-40/50
GS 70/80
SB 60/70
SB
10/40
SB
SB 25
10/30
.BA cuts two and four weeks after application. Separate control boxes treated with one herbicide are provided, which provide the basis for determining the amount of damage reduced by the herbicidal antidote. The results of these tests are shown in Table. 3Antidote activity. Method of application: seed treatment - ST, in the groove - IF, the introduction before sowing - PPJ {reserve mix). Cultivated varieties: chmeny-VA (Hordeum vulgare (1), corn - CN {Zea raeize), cotton - ST (Giossypium Hirsutum), sorghum, - GS (Sorghum vulgarie), rice (0ryza sativa), co - SB {Glycine max), wheat - WT (Triticum aestivum). Species of species: Watergrass-WG (Echinochloa crusgal), green foxtail - FT (Setaria virid is), wild onions - W (Avena fatue (L), Shattereane-SC (Sorghum bicolor). T a b l and c a 3
29
30 Continued table. 3
31
32
Continued TIBL. 3
37
PPI
Ronit
Vernam
IF
Vernam
IF
Vernam
PPI
five
Ordrzm
IF
Vernam
Ordrzm
PPI
IF
to the horses
PPI
Eptam PPt Ordram
PPI
Ronit
Ppl
Sutan
Wbrnam
IF
sixteen
Ordram
PPI
Ordram
PPI
PPI
Ronit
IF
Vernam
PPI
Ordram
38
Continuation of table 3
60/70
SB BA CN WT CN CN GS GS 50/82 50/70 60/75 75/90 "0/50 70/85 60/100
35/65
SB SB 50/80
50/70
SB SB SB GS GS GS GS SB
30/65
20/50
80/90
60/85
40/50
60/100
60/80
39
906 N
0
Continued table. 3
k
i2
906347 Continuation of the table. .five
Ronit ST
R-12001 ST
PPI ST PPI IF ST PPI
1 IF PPI PPI PPI PPI IF ST ST
Ronit
ST PPI
R-12001
125
GS GS GS GS GS GS GS
20/70
50/85
125
75/95
25
60/95
60/100
tO / lOO 25
60/95
60/70
80/100
R
20/65
SB SB
SB SB SB SB
30/70 20/65 13/50
25 15/25
4 25
5/30
WT WT WT
75/93 5
70/95
90bЗ (7
14b
Continued table. 3
one

EABR Continued Tab. 3
ri,
one
OrdramPPI
RonitPPI
RonithIf
p-12ao1PPI
one
RETURN
RETURN
EptamPPI
OrdramPPI
RonitPPI
RonithIf
P-T2001PPI
Sutan
PPf
Refund
IF
five
Grains
IF
IF IF
Vernam Ronit
Verna IF Verna IF Verna -IF
26
k +5
GS
60/80
GS,
50/75
GS
30/75
GS
50/90
BA
10/90
CN
50/90
, 75 + 5
GS
"O / IOO
AO / 80
GS
20/75
GS. 30/65
GS 30/90

GS

GS 20/96
+5.
BA 20/70
+5
CN GS
20/90 30/65 +5
-30/96
GS
five
50/100 5
60/90
CN +5
53
906 N
S Continued table. 3
55
56
30631 7 Continued table. 3
57
58
DOSA Continued table, 3
36
burns
IF
BA 30/60
1 + 5
PPI
Ronit
GS O /
2 + 5
63
Vernam
IF
6k Continued table. 3
0/70
5 + 5
CN
IF
10/30
6 + 5
SB
67
68
906347 Continuation of the table. 3
69
70
ebz; Continued table. 3
71
IF
Vernam
72
Continued table. 3
WT
50/70
1 + 5
73
7
DOSA Continued table. 3
75
76
Continued table. 3
77
78
9063 7 Continued table. 3
79
80
Continued table. 3
81
HOB
82 Continued table. 3 Result - antidot damage procedure / percentage of damage with a single herbicide. In experiments with different types of weeds and cultivated plants, it was found that the destruction of weeds persists, while the cultivated varieties remain protected or the percentage of damage is reduced compared to with control experience or evaluation. The test antidote compound is not contained in the control box. In tab. 4 shows examples of the results obtained. Table k
85
86 Continuation of table. BUT
Test assessment of legumes ™
NII ...
The various proposed ant compounds are capable of reducing the spoilage of a class of cultivated plants, for example legumes, i.e. such plants that are symbiotically associated with nitrogen fixing organisms. Such plants include, for example, co, species; haricot beans (PhaeseoJus vulgar s (L)), ground nut, alfalfa, clover and tTP.
Tests were carried out to determine the effectiveness of the compounds described as substances that reduce the deterioration of legumes with thiocarbamate herbicides such as eptam. Experienced-. Yut different varieties of edible. Beans; peas. Antidotes are applied to 55 with a consumption rate of 1.12 kg / ha and 2 lb / acre (2.2 kg / ha) by the introduction method before sowing mixed with eptan, with
Continued table. four
The application rate was 6 pounds per acre (6.8 kg / ha) using an administration method prior to sowing.
Basic solutions.
An antidote. 39 g of each of the tested compounds are dissolved in 25 ml of acetone, 25 ml of this solution is equivalent to the consumption rate of f lb / acre (1.12 kg / ha when administered before sowing,
Herbicide. 15bO mg of brewers BO is dissolved in 250 ml of water, 5 ml of this solution is equivalent to a consumption rate of 6 lb / acre (6.8 kg / ha) when administered before sowing.
Test plants: NavyNB beans, common beans - KB, Pinto beans - PB (various varieties (Phaeseolus vulgaris LJ, as well as peas (Pi sum satlvuo L). Weed varieties used in the experiment; Watergrass-Wg and foxtail - FT ,
The test results are presented in tab. five
89
ebz

权利要求:
Claims (1)
[1]
90 Table 5 91 Thus, the proposed andotic herbicidal composition has a lower toxicity of the herbicide to cultivated plants. Claims of the invention An antidotal herbicidal composition containing direct thiocarbamate aqueous form of a general formula as a herbicide, where ethyl, propyl; ethyl, propyl, iso-butyl, ich-propyl, butyl, cyclohexyl Cpi Ri - together form a hexamet and an antidote that distinguishes the germ from a cultivated plant, it contains as an: thidot N- (benzenesulfonyl) carbamate of the general formula II O but f Where I is hydrogen, bromine, hlsf, trifluoromethyl labels, methyl P is an integer of 1–3 (provided that X is bromo, trifluoromethyl or methoxy, n 1); R is alkyl haloalkyl, where the halogen is bromine, chlorine, fluorine in an amount of -C, 6, alkenyl C3 Cd, 2-chloroallyl, alkynyl, Diethylamino phO phonomethyl, phenyl substituted with methyl, propyl, butyl once, twice or three times, chloro-phenylthiomethyl ethoxyethyl, cyanisopropyl, formamidoethyl, ethoxycarbonylmethyl, ethoxycarbonylethyl, 1-ethoxycarbonylpropenyl- (1, 2), methylcarbonyl methyl, 1,3-dioxycyclohexane-5, 5-methyl-methyl, 1-aryl, methyl, carbonyl, ethyl, methyl, carbonyl, ethyl, acetyl, 5-5, 5-methyl , methoxybenzyl, 3-pyridylmethyl, fenok ietil, 3-fenilpropinil-2 benzaldimine, atsetonimino, metiltioatsetimino, triftoratsetilamidometil, tsianetiltioetilen, a weight ratio of safener: Gerd (0,01-6,6): 1. Sources of information that are taken into account in the examination, N. N. Melnikov. Chemistry and techno pesticides. M., Himi, I, (prototype). .Patent of France No. 2119579, C 07 s, published. 0 08172.

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RU1743153C|1995-02-27|N-[4-2'-|phenyl]-n- ethyl-n'-phenylurea showing growth- regulating and antidote action

JPH06239709A|1994-08-30|S-benzylthiol carbamate and use thereof in rice field as herbicidal agent

US4293701A|1981-10-06|N-| carbamates - herbicidal antidotes

EP0397602A1|1990-11-14|N-phenylpyrrolidines

US2643965A|1953-06-30|New chemicals and fungicidal compositions containing same

DE2421195C2|1982-12-23|Thiazolidine compounds and herbicidal antidote containing them

DE4092524C2|1996-09-12|Substituted phenylsulfonyltriazinylureas, their salts and agents with plant growth regulating action

DD215781A5|1984-11-21|PROCESS FOR PREPARING 3-ARYL-5,6-DIHYDRO-1,4,2-OXATHIAZINES AND THEIR OXIDES

SU558623A3|1977-05-15|Antidote to herbicides such as acetanilides and thiocarbamates

US3977861A|1976-08-31|Herbicide composition

US4106924A|1978-08-15|Pesticidal compositions

CH624554A5|1981-08-14|Method of protecting crops of plants

SU671700A3|1979-06-30|Antidote herbicide

US4419523A|1983-12-06|N-| carbamates-herbicidal antidotes

DE2634278A1|1977-02-24|WEED REPRODUCTORS CONTAINING DIBROME-SUBSTITUTED PROPIONAMIDES AS ANTIDOTS

SU1106442A3|1984-07-30|Herbicide composition

JP3624209B2|2005-03-02|Agricultural and horticultural fungicides

同族专利:

公开号 | 公开日

PL193516A1|1978-03-28|

US4230874A|1980-10-28|

PL102610B1|1979-04-30|

引用文献:

公开号 | 申请日 | 公开日 | 申请人 | 专利标题

US3377375A|1963-02-07|1968-04-09|Monsanto Co|N-aralkylsulfonyl carbamates|

US3326967A|1965-11-26|1967-06-20|Olin Mathieson|Trihalomethylthio substituted n, n'-sulfonyl-bis-carbamates|

US3512955A|1967-11-06|1970-05-19|Monsanto Co|Method of protecting plant growth|

EG10699A|1971-06-23|1976-07-31|Bayer Ag|Novel n.carbamic aryl acid esters method for preparation and their use for controlling plant growth|

US3790619A|1971-11-01|1974-02-05|Dow Chemical Co|Fluoride substituted carbanilates|

US3978228A|1971-12-13|1976-08-31|Kumiai Chemical Industry Co., Ltd.|Method for killing noxious fungi in plants using dihalo sulfonates|

US3779760A|1972-10-02|1973-12-18|Sony Corp|Method of producing a striped cathode ray tube screen|US4419523A|1979-12-31|1983-12-06|Stauffer Chemical Company|N- carbamates-herbicidal antidotes|

US4434000A|1979-08-24|1984-02-28|Stauffer Chemical Company|N- carbamates herbicidal antidotes|

DE3000076A1|1980-01-03|1981-09-03|Hoechst Ag, 6000 Frankfurt|GROWTH-PROMOTING AND PLANT-PROTECTING AGENTS|

US4931580A|1980-11-19|1990-06-05|Pallos Ferenc M|Aryl sulfonylurea carbamates and thiolcarbamates and salts thereof: herbicidal antidotes|

EP0066976B1|1981-06-09|1987-05-13|Imperial Chemical Industries Plc|Arylsulphonyl urea derivatives; their use as herbicides; and herbicidal compositions containing them|

US4443243A|1981-07-16|1984-04-17|Ciba-Geigy Corporation|N-Phenylsulfonyl-N-triazinylureas|

US4802912A|1981-08-10|1989-02-07|Stauffer Chemical Co.|Herbicide antidotes|

US4518776A|1982-07-19|1985-05-21|Ciba Geigy Corporation|Process for producing sulfonylureas|

US4938796A|1987-07-06|1990-07-03|Ici Americas Inc.|Herbicidal compositions of acylated 1,3-dicarbonyl herbicides and antidotes therefor|

US5527762A|1990-12-12|1996-06-18|Zeneca Limited|Antidoting herbicidal 3-isoxazolidinone compounds|

US5627131A|1995-01-09|1997-05-06|Zeneca Limited|Herbicidal compositions of 4-benzoylisoxazole and antidotes therefor|

US7741485B2|2003-04-08|2010-06-22|Basf Aktiengesellschaft|Benzenesulphonamide derivatives as herbicides or desiccant/defoliant compounds|

法律状态:

优先权:

申请号 | 申请日 | 专利标题

US05/721,721|US4230874A|1976-09-13|1976-09-13|N- carbamates-herbicidal antidotes|

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