Herbicide composition (its variants)

专利摘要:
Thia-diazole derivatives having the following partial structural formula had selective herbicidal activity on some crops. A process for producing these compounds is also disclosed: <IMAGE>
公开号:SU1706370A3
申请号:SU853939370
申请日:1985-08-07
公开日:1992-01-15
发明作者:Хагивара Кендзи；Исикава Хисао；Хосака Хидео；Инаба Хидео
申请人:Ниппон Сода Компани, Лимитед (Фирма)；
IPC主号:

专利说明:

This invention relates to chemical control of weed and undesirable vegetation.
The aim of the invention is to increase the herbicidal activity of a composition containing a thiadiazole derivative as an active substance.
Example 1, Getting
-chloro-2-fluoro 5 (1-ethoxycarbonyletho si) phenyl mi HO) J -5,6- (dihydro-6-methyl-3H-oxazole (2,3-e) (1,2, Mtiadiazole (typical recipe).
A solution of 9.6 g of 1-chloro-2-fluoro-5- (1-ethoxycarbonylethoxy) phenyl isothiocyanate in 100 ml of chloroform is cooled to -10 ° D and 3.8 g of 5-methyl-2-amino acid is introduced into it. 2-oxazolinch, the reaction mass is stirred for 5 hours at 0 ° C and then a solution of 5, Obg of bromine in 30 ml of chloroform at a temperature from
-10 to 0 ° C. After that, the reaction mass is washed with 50 ml of an aqueous solution of 1 N NAOH, then 5.0 ml of water is dried with magnesium sulfate, filtered, chloroform is distilled off in vacuo, and the remaining product is purified on a chromatographic column. Get 10, OA g of the product with 2 1i5870.
Example 2. Getting
-chloro-5 (1-ethoxy-carbonylethoxy-carbonyl) -2-fluorophenylamino) -6-methyl-5,6,7,7a-tetrahydro-3H-pyrrole (2, 1-c) (1, 2, Mtiadialol.
In solution 3 (5 carboxy-chloro-2
-fluorophenimino) -6-methyl-5,6,7,7a-tetrahydro-ZN-pyrrole (2,1-c) (1,2,) thiadiazole (0.7 g) in acetonitrile (10 ml) Anhydrous potassium carbonate (0.3 g) and 2-bromopropionic acid ethyl ester (O, k g), the mixture is heated to room temperature, filtered, the solvent is distilled off under reduced pressure, and the remaining product is purified by crystallization from ether-hexane. Obtain 0.8 g of the product with so pl. Under the conditions of examples 1 and 2, I receive other compounds, the list of which is presented in Tables 1 and 2.
Forms of the herbicidal composition Composition 1 - wettable powder containing mac.ch .:
Active substance 60 Bela soot7 Talc 25 Sodium laurip Sulfonate 8
0
five
0
five
0
five
0
five
0
five
Part 2 - wetting powder containing, may. including:
Active substance 5 Bela soot5 Diatomite shcheml 3 Sodium diisopropyl-naphthalene sulfonate 7 Composition 3 - wetting powder containing, by weight.h .:
Active substance 20 Bela soot 3 Clay 5 Pyrophyllite 25 Sodium diisooctyl sulfosuccinate 7 Composition 4 - wettable powder containing, by weight.h .:
Active substance 10 Bela soot 5 Clay 79 Polyoxyethylene nonylphenyl sulfonate sodium 6 In formulations 1-A, each component is mixed until a homogeneous mixture is reached and diluted to the thinnest particles to obtain wettable powders.
Composition 5 - emulsifying concentrate containing, by weight.h .:
Active substance 60 Polyalkylbenzenes 32 Complete polyethylene nonylphenyl ether8 Composition 6 - emulsifiable concentrate, containing, May., Am: Active substance 50 Xylene 23 N-methylnaphthalene 18 Polyethylene ethylene nonylphenyl ether 9 Composition 7 - emulsifiable concentrate, containing, wt.h. .: Active substance 0 Kerosene 53 Polyoxyethylene tristyrylphenyl ether 7
Composition 8 - emulsifiable concentrate containing, in parts by weight: Active substance 20 Xylene 8 Limethylformamide, Popetyl benzosulfonate sodium 8 Composition 9 - emulsifiable concentrate containing, in parts by weight:
Active substance .10 Naphtha solvent 63 Dimethylformamide 20 Polyoxyethylene tristyrylphenyl ether7 In formulations 5–9, each component is mixed together to provide emulsifying concentrates.
Composition 10 - granules containing
May including:
Active substance 10 Talc30 Clay 3 Bentonite 10 Sodium alkyl sulfonate 7 Composition 11 - granules containing
ma.ch .:
Active substance1 Clay 77 Bentonite 20 Sodium ligninsulfonate 2 Composition 12 - granules containing
May.
Active substance 0.5
Clay97.5
Polyvinyl
alcohol 2
In formulations 10-12, each component is blended until a homogeneous mixture is obtained and ground to obtain fine particles. After adding a small volume of water, these particles form in the form of granules with a diameter of about 0.5-1.0 mm.
Example 3. The test for the treatment of seedlings after their appearance.
Mari white seeds, white quinoa, reeds and soybeans are sown in clay pots (13 cm deep and 18 cm in diameter) containing loamy-loamy soil, and left for growing in a greenhouse. After the weeds are grown to a height of 4-8 cm, the plants are sprayed with an aqueous suspension, a dilution of the emulsifying concentrate and the wetted powder with water is prepared to predetermined concentrations.
Three weeks after treatment, the degree of damage to each of the plants is observed and evaluated on scales with indices from 0 to 10, having the following values:
Index
Degree of damage,%
OO
220-29
660-69
880-89
10,100
Indices 1, 3, 5, 7 and 9 mean intermediate degrees respectively
between Oi2, 2i, i6,6i8, 8 and 10.
The results of the experiments are presented in table.3.
Example 4. Field trials for growing rice plants.
0 Seeds of chicken millet, monochoria, reed and small-leaved fodder long, g grown in a greenhouse, placed at a depth of 0.2-0.5 cm in plastic pots (15 cm deep and 16 cm in diameter) containing soil for the rice floor, and transfer t 2 plants of rice at a stage of development with 2-3 leaves. The next day, the pots are poured with water to a depth of 2-3 cm. Immediately nano0 with t granules of each of the proposed compounds. At the dosage indicated in the table. The pots are kept in a greenhouse.
3 weeks after treatment, the extent of damage to each of the 35 plants is observed and evaluated on the same scale as for Example 3.
The results are shown in Table. t.

权利要求:
Claims (3)
[1]
1. A herbicidal composition in the form of a wetting powder, containing the active substance, a thiadiazole derivative, a carrier and a surfactant, characterized by that, in order to increase the herbicidal activity, it contains as an active substance a thiadiazole derivative of the general formula
50F
where R is methoxycarbonyl,
1- (methoxycarbonyl) ethyloxy, 1- (1-ethynylcyclohexyloxycarbonyl) isopropyloxy, 1-methylpropargyloxycarbonyl,
71
as a carrier, a substance selected from the group; 1 white carbon black, talc, diatomaceous earth, clay, pyrophyllite or a combination thereof, as a surfactant a substance selected from the group: sodium lauryl sulfonate, diisopropylnaphthalene sulfonate sodium, polyoxyethylene nonylphenyl sulfonate sodium, diisoxyl sodium sulfosuccinate or a combination thereof, in the following ratio, wt.%:
Active substance 10-60 Carrier 32-8 Surface no-active substance 6-8
[2]
2. The herbicidal composition in the form of an emulsifying concentrate, containing the active substance — a derivative of thiacyazole, a solvent and a surfactant, meaning that, in order to increase the herbicidal activity, it contains as an active substance a derivative of thiadiazole of the general formula
F
r-n-rN
where R is COOR, OR, isopropyloxycarbonylmethylthio, 1- (methoxycarbonyl) these lthio; R-- 2-phenoxyethyl, 1- (ethoxycarbonyl) ethyl, 1 - (propyloxy carbonyl) ethyl, isopropylidene imino;
R3 - -isoylpropylcarbonylmethyl, 1- (methoxycarbonyl) ethyl, 1- (2-benzyloxyethoxycarbonyl) ethyl, 1- (carboxy) propyl X - oxygen, sulfur or -CHv-, the solvent selected substance from the group: xylene, polyalkylbenzene, dimethylformamide, tilnaphthalene, naphtha solvent, kerosene, or a combination thereof, as a surfactant a substance selected from the group of polyoxyethylene nonylphenyl ether, docecylbenzenesulfonate sodium, polyoxyethylene triestirylphenyl ether, in the following components, %: Active 10-60 Solvent 32-83 Surfactant
063708
[3]
3. A herbicidal composition in the form of a granulate, containing the active substance — a derivative of thiadiazole, a carrier and a surfactant — characterized in that, in order to increase the herbicidal activity, it contains as an active substance a derivative of thia-uiazole of the general formula
F
G |. | -N-T KO -R
;
ъ
H x n
ABOUT
and
one
where TCt is hydrogen or methyl,
g - hydrogen, methyl or ethyl | R, is hydrogen, chlorine and bromine, R is isopropyloxycarbonyl, propyloxy, propargyloxy, 1-methylpropargyloxy, (1-ethylpropargyloxy, 1-cyanopropyloxy, 1- (ethyloxycarbonyl) butyloxy, 1 - (benzylminocarbonyl) ethyloxy , X - oxygen, sulfur or as a carrier substance selected from the group: talc, clay, benthonite or a combination thereof, as a surfactant substance, selected from the group: sodium alkyl sulfonate, sodium ligninsulfonate, polyvinyl alcohol , in the following ratio of components. May .:
Active substance 0.5-10 Media 83-97 5 Surfactant 2-7
Priority featured:
i
08.08.8 with R - propyloxy, propargyloxy, 1-methylpropyl-glucoxy, 1-ethylpropargylok-i si, R ,, - chlorine, bromine, tj - hydrogen, methyl, r2-hydrogen, methyl, ethyl, X - oxygen or sulfur.
01/10/85 with R - COOR2, OR3, isopropyloxycarbonylmethylthio, 1- (methoxycarbonyl) ethylthio, methoxycarbonylmethyloxy, 1- (methoxycarbonyl) ethyloxy, 1- (ethylenecyclohexyloxycarbonyl) isopropyloxy, 1-me - tilpropargyloxycarbonyl,
91706370
isopropyloxycarbonyl,
1-cyanopropyloxy, 1- (ethoxycarbonyl) butyloxy.
i
The active substances of the general formula
ten
1 - (benzylaminocarbonyl) ethyloxy, R | - hydrogen, X - -CH2-.
Table 1
: gmmgmo) -s1
CH3-VV R
Sulfur Methyl Methyl
Sulfur sulfur
Sulfur
Oxygen
Oxygen
Oxygen
Oxygen
CH, CH.
Methyl Methyl
Hydrogen Hydrogen
Methyl Methyl
 Water-Methyl ROD
Hydro-methyl genus
Methyl Methyl
1- (Ethoxycarbomyl) butyl oxy and
1-Methylpropargyloxy Propargyloxy
Propargyloxy
1-Cyanopropyloxy
1- Benzyl inocarbonyl) ethyloxy
Propargyloxy
Hydrogen
Hydrogen
Hydrogen
Ethyl Propargyloxy
Methyl 1-Ethylpropargyloxy
Methyl Propargyloxy
500
-H
-II- |
250 p
and n
500
-H
-And-and.
500
- H - | |
500 n
Continued table. 2
Chlorine
Chlorine Chlorine
Chlorine bromine
Chlorine Chlorine Chlorine Chlorine Chlorine
95-96
&. "T
116-117
103-106 fl 1.5680
50-530
105-108
121-122
, 6036
120-130
Table 3
one
0
0
0
0
3
3
ten
ten
Yu
ten
ten
ten
ten
ten
ten
ten
ten
ten
ten
ten
ten
ten
ten
ten
ten
ten
ten
ten
ten
40
ten
ten
ten
ten
ten
ten
ten
ten
ten
ten
ten
ten
ten
ten
ten
ten
ten
ten
ten
ten
ten
ten
ten
ten
ten
ten
ten
ten
ten
ten
n
five
6
7
eight
9
0
ten
eleven
12
ten
eleven
12
ten
eleven
12
ten
eleven
12
ten
eleven
12
ten
eleven
50 "|.
- |.
25 |
| 25
m and
50
m and
25
|
50 m
Continued table. 3
ten
ten
ten
C1
(BUT)
Table
17
1706370
18 Continued tchbl. k

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同族专利:

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SU1746884A3|1992-07-07|

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CA1253504A|1989-05-02|

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ES552944A0|1987-10-16|

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GB2163427A|1986-02-26|

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FR2568881B1|1988-12-30|

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CH666691A5|1988-08-15|

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KR870001694B1|1987-09-24|

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GB8519896D0|1985-09-18|

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ES8703438A1|1987-02-16|

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IT1184690B|1987-10-28|

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RO92378A|1987-11-30|

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RO96413A|1989-03-30|

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AR241115A1|1991-11-15|

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DE3528583A1|1986-02-13|

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RO92378B|1987-12-01|

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ES552943A0|1987-10-16|

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BR8503732A|1986-05-13|

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KR860001819A|1986-03-22|

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ES8800242A1|1987-10-16|

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AR241115A2|1991-11-15|

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DE3528583C2|1989-10-12|

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ES546006A0|1987-02-16|

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IT8548457D0|1985-08-08|

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GB2163427B|1987-11-25|

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RO96413B|1989-03-31|

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FR2568881A1|1986-02-14|

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ES8800232A1|1987-10-16|

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US4812161A|1989-03-14|

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CA2394422A1|1999-12-16|2001-06-21|Basf Aktiengesellschaft|Phenoxy and thiophenoxy acrylic acid compounds as herbicides|

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JP6937748B2|2015-10-08|2021-09-22|エフ エム シー コーポレーションＦｍｃ Ｃｏｒｐｏｒａｔｉｏｎ|Bicyclic azole pest control agent substituted with a heterocycle|

法律状态:

优先权:

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申请号 | 申请日 | 专利标题

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JP59164855A|JPS6143192A|1984-08-08|1984-08-08|Thiadiazole derivative, preparation thereof and herbicide|

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JP60001446A|JPS61161288A|1985-01-10|1985-01-10|Thiadiazole derivative, preparation thereof, and selective herbicide|

---