Method of producing derivatives of 1,5-diphenylpyrazol-3-carbolic acid

专利摘要:
1,5-Diphenylpyrazol-3-carbonsäurederivate der Formel worin Ra und Rb unabhängig voneinander je Halogen, C₁-C₅-Alkyl, C₁-C₅-Halogenalkyl, C₂-C₅-Alkenyl, C₂-C₅-Alkinyl oder Cyano, n Null oder eine Zahl 1-3 bedeuten und OR₁ Hydroxy ein pflanzenphysiolo­gisch verträgliches Salz oder einen beliebigen Esterrest bedeuten, vermögen spezifisch die phytotoxische Wirkung von Phenoxy-propion­säureester-Herbiziden der Formel II zu antagonisieren. Hal₁ Fluor, Chlor, Brom, Jod oder Trifluoromethyl, Hal₂ Wasserstoff, Fluor, Chlor, Brom oder Trifluoromethyl, Z für Stickstoff oder Methin (-CH=), X ein Sauerstoff oder Schwefelatom, R₁ Halogen, Trifluormethyl, Nitro, Cyan, C₁-C₄-Alkyl oder C₁-C₄-Alkoxy und n 0, 1, 2 oder 3 und T ein Ester-, Amid-, Cyanoamid- oder Oximrest bedeuten. Diese Komponenten enthaltende Mittel als selektive Herbizide und die Verwendung dieser beiden Wirkstoffe zur Bekämpfung von Unkräutern in Nutzpflanzenkulturen werden beschrieben, wie auch neue 1,5-Diphenyl­pyrazol-3-carbonsäurederivate entsprechend der Formel I sowie deren Herstellung.
公开号:SU1597099A3
申请号:SU874203524
申请日:1987-10-21
公开日:1990-09-30
发明作者:Мозер Ханс；Бенер Беат；Фери Вернер
申请人:Циба - Гейги Аг (Фирма)；
IPC主号:

专利说明:

The invention relates to a process for the preparation of new derivatives 1, phenylpyrazole 3carboxylic acid, for the protection of cultivated plants of the harmful effects of herbicidally active esters phenoxyalkane carboxylic acids. (/ II II (V-NHNH 2-Н НЗСО - с - с С1
to a solution of 21.2 g (0.103 mol) of benzoyl pyruvic acid methyl ester in 100 ml of glacial acetic acid was added 19.8 g (0.105 mol) of chlorophenylhydrazine hydrochloride 2 () and 8.6 g (0.105 mol) of sodium acetate. Thereafter, the reaction mixture is boiled at reflux temperature for 2 hours, after which it is cooled to room temperature and immediately after this is poured into ice water,
oh oh
ABOUT
С-СНз-ÑНзОС-СОСНз
A mixture of 75 ml (D, A05 mol) of sodium methoxide solution and 30 ml of methanol is cooled before and then slowly mixed with 48, g (0.4 mol) of acetophenone, with stirring. To this mixture a solution is added dropwise with stirring , 2 g (0.4 mol) of oxalic acid dimethyl ester in 100 ml of methanol. The reaction mixture becomes cloudy and immediately after it a yellow thick precipitate is formed, which is almost impossible to mix. Methanol is added to it until the reaction mixture can be stirred again. After 3 h after further stirring at room temperature, the precipitate is filtered off with suction, washed with diethyl ether and sucked dry. The filtered product is suspended in water and with stirring and cooling with glacial acetic acid, the pH value is adjusted to 4, Benzoyl pyruvic acid methyl ester drops out. It is filtered, washed with water
In this case, the resin is introduced into the ethyl acetate and washed to a neutral reaction with water and 1M soda solution. The organic phase is separated, dried over sodium sulfate and evaporated. rotary evaporator. The remaining oil is crystallized from diisopropyl ether. In this way, 17.1 g of the desired product, c.t., pl. Are obtained. The benzoyl pyruvic acid ester required as the starting material is obtained as follows:
about 00
II II II
SSNGSSOSNz
ice and dried in a desiccator over phosphorus pentoxide. 42 g of ether are obtained; t, mp, 56 ° C,
And, p and me 2, Chloride 1 (2 chlorophenyl) 5 phenylpyrazole 3 carboxylic acid.
A mixture of 149.1 g 1 (2 chlorophenyl) 5 phenylpyrazole 3 carboxylic acid and 2000 dry ethylene chloride is not heated until, 40 ml of tionyl chloride are added dropwise to this mixture with stirring for 12 minutes. The reaction mixture is then held for 2.5 hours at reflux temperature, then cooled to room temperature and evaporated in vacuo. Obtain 126 g of the specified acid chloride,; t, mp, 101-10 ° C (from a mixture of hexane hexane).
Analogously to examples 1 and 2, the compounds shown in Table 1 are obtained:
Derivatives of 1.5 diphenylpyrazole 3 carboxylic acid in accordance with the invention are used as an object of the invention. A method for producing new derivatives of 1.5 Diphenylpyrazole 3-carboxylic acids, which, in contrast to the known derivatives, have a herbicidal antagonistic effect. Example .1. 1 (2 Chlorophenyl) -3 methoxycarbonyl 5 Fensch 1pyrazole COOCH3 with
antidotes in mixtures with herbicidally active esters (fe NILE, pyridine 2 yl, 4 benzoxazole, D-benzthiaeol, A-henoxaline -2-yl) oxy-phenoxy} propionic acid to kill weeds in crops, useful plants.
The proposed compounds can treat both monocotyledonous and dicotyledonous weeds, as well as areas with seedlings of cultivated plants, sunflower and intended for sowing of cultivated plants.
The consumption rates of antidotes for herbicides depend most of all on the type of application. When processing fields, which is carried out with the use of tank mixtures with a combination of antidote and herbicide or with separate application of antidote and herbicide, as a rule, the ratio of antidote to herbicide is from 1: 100 to 10: 1, preferably from 1:20 to 1: 1 in particular, 1: 1. In the case of seed dressing, a considerably smaller amount of antidote is needed in relation to the herbicide per hectare of the treated surface.
As a rule, when processing fields, 0.01-10 kg of antidote per hectare, preferably 0.05-0.5 kg, are applied.
When seed is treated, as a rule, 0.01-10 g of antidote per kilogram of seeds, preferably 0.05-2 g, is applied. If the antidote is applied in liquid form shortly before sowing when the seeds swell, then it is advisable to apply antidote solution, which contains the active substance with a concentration of from 1 to 10,000, preferably from 100 to 1000 honey,
In order to use these compounds or products containing these compounds to protect cultivated plants against the harmful effects of herbicides of this formula, various methods and technologies should be kept in mind, for example the following.
Seed treatment. Seed treatment with an active substance of the specified formula, prepared in the form of a wettable powder, by shaking in a vessel until it is evenly distributed on the surface of the seed (dry treatment). Approximately 1-500 g of the active substance is used (4 g - 2 kg wetted powder) per 100 kg seed n.
Seed treatment with emulsion concentrates of active substances by the method of wet treatment. Pickling by dipping
 mn in broth with 50-3200; m, d, active substance for 1-72 h and, if appropriate, the subsequent drying of the seeds (by dressing with a pellet),
Seed treatment or treatment of germinated sprouts is the preferred application method, since treatment with an active substance
with fully focused on the target culture. As a rule, 1-500 g of antidote are used, preferably 5-250 g per 100 kg of seeds, and depending on the methods that make it possible
0 the addition of other active substances or trace elements, the indicated concentration limits may deviate from the lower or upper values (re-etching) o
5 Application from tank mix (from tank).
If liquid treatment with a mixture of an antidote and a herbicide is used (in an appropriate case, quantitative
0 wearing from 10: 1 to 1: 100), then the consumption rate of the herbicide from 0, 1 to 10 kg / ha. Such tank mixes are applied before or after sowing.
Application to the seed groove, Antidote is applied in the form of an emulsion concentrate, wettable powder or in the form of a granulate in an open, screened groove and after harrowing the furrows in a normal manner.
A herbicide is applied in the experiment to seed germination.
Biological example, In a greenhouse, plastic pots containing 0.5 liters of Zemppi are sown with seeds of plants to be tested. When the plants reach the stage of development of 2-3 leaves, antidote and herbicide are applied together as a tank liquid. 21 days after application, the condition of the plants is assessed and the protective effect of the antidote is calculated. The protective effect is the difference between the damage caused by the action of a herbicide on an untreated
An antidote plant and an antidote-treated plant.
The test results are presented in Table 2, (culture: summer wheat Besso; herbicide: 2 (K) (5-chloro-3-fluoropyridine 2 or -oxy) phenoxy propionate propargyl ether).
A comparison of the herbicidally antagonistic effect of several compounds according to the invention and similar in structure of limestone compounds of the formula A B have been carried out in a greenhouse:
C1
COOCjHs
CH (CHS) 2
(BUT)
SOOSgNb
as a herbicide, a 2 (K) -2 ester is used. (torpiridin2 1shoxy) phenoxy propionic acid of the formula
F. СНз О ОУ-Л-Х О -О-СН - С - OSI 2-С Е СН
"R

and as a cultivated plant, Basso wheat variety is used.
The active substances will be finely crushed and prepared suspension concentrate with additives of the following composition,%:
Substance tabl
tsy 140
Ethylene glycol 10
Ionylphenolpoly
ethylene glycol
ether (15 mol. units
ethylene oxide) 6
Ligninsulfonate
rub 10
Yarboxymethyl
cellulose1
37% solution
formaldehyde 0.2
Silicone oil
Used as 75%
water emulsion0.8
Water32
This is how a suspension concentrate is obtained from which by dilution with water, suspensions are prepared, which in a concentration of a g of active substance and 500 l of water irrigate a hectare
square.
The test is carried out as follows.
In a greenhouse, plastic wheat pots containing earth are placed in Basso variety wheat seeds. When the plants reach stage 2–3 leaves, the herbicide is applied as a mixture together with the test substance. After 21 days thereafter, the state of the plants is evaluated and the protective effect is calculated. This is the difference in damage that only a herbicide is applied to the plant, and the mixture of the herbicide with the active substance is expressed as a percentage.
The test results are presented in Table. 3 (herbicide consumption 400 g / ha
As can be seen from the presented, using the compounds according to the invention, good results of protective action are achieved, reducing the damage by herbicide from 90 to, in contrast to the known structural analogues (compounds. A and B).

权利要求:
Claims (1)
[1]
Invention Formula
The method of obtaining derivatives 1,5difensh1pyraz l 3 carboxylic acid of General formula
COORi
(KB) p-.-; l N
R
halogen, C —C alkyl;
de l. Re halogen, C C-alkyl, meth oxy;
O, 1 or 2;
n R,
hydrogen or physiologically tolerated by the plant metal or ammonium cation, C C alkyl, unsubstituted or substituted by one halo gene, nitro, C, C4 alkoxy carbonyl, trimethylsilyl, amino, di (C C) alkylamino, C C alkenyl, kinil, thiazole radical, pyrazole, hyenyl, furyl or phenyl, unsubstituted or substituted by halogen, C 4 alkyl or C C-apcoxyl, or substituted several times with halogen or cycloalkyl, unsubstituted or substituted C C alkyl, in which the acetophenone of formula I R (i) n where R and p have the indicated meanings, is subjected to interaction in an inert organic solvent in the presence of a base with an equimolecular amount of oxalic diester of the formula (Re) n RiOC-C-ORi, and O O where R has the indicated values, obtained Benzyl acid ester of the formula CO-CHjCO-COORi where Cd , n and R have the indicated values, are reacted with an adequate amount of phenylhydrazine of the formula) where Rg and n have the indicated values and the resulting condensation product is cycled in an acidic medium at the boiling point of the reaction mixture with the separation of the target product, T a b l and c a 1 COORi /.
eleven
2-C1 2-C1 2-Cl
2-cl
2-Cl 2-Cl 2-Cl
2-Cl 2-Cl
2-cl
2-Cl g-C1 2-Cl 2-Cl
2-Cl 2-Cl 2-Cl
2-Cl 2-Cl g-Cl 2-Cl 2-Cl 2-Cl 2-Cl 2-Cl 2-Cl
2-Cl 2-Cl 2-Cl 2-Cl
2-Cl,
2-Cl 2-Cl
2-Cl 2-Cl
2,4-Cli
2,4-Cli 2,4 Cl 2,4 Cl 2,4 Cl-i
159709912
Table 1
С (СНз) гСООС5, Н СНС-ГСЫ. 11iran 2 ilmethyl benzyl
 e Phenoxyethyl Cyclopropyl Methyl
Cyclopentyl methyl 2,2 Dimethyl 1, 3-DIOXO
Lan 4 shmetitil
2 Tenil
CH, iCH CHClCHjC (Cl) CH CH CH SiCCHg)
Sig31 (Siz) e
Pyrazole IL Ethyl
(W4) CH3 CH., 3
Cyclohexyl (CHj) N e
) CH CH OCH iCHjOCH2CH (Br) CHCCHiCl)
SNGS (SNZ). (CH
CH (CHE) (CH2, 6 Dimethylcyclohexyl
2 furfuryl
Morpholinoethyl CHjCN
Cyclohexyl
methyl
Feast
CH COOCHj
CH (CH) (CH,) CH CH () (CH, CH,
CH (SN)
CH (CH3) (CH) CH3CHO.
111
2-CH3
nineteen
15 709920
table 2
400
200
12
400
12
200
12
100
400
24
24
200
24
100
400
36
36
200
100
36
49
400
49
200
75 75 75 75 63 75 63 75 88 75 75 75 75 75 63 63 50 63 63 63 88 88 88 75 75 75 75 63 63 63 63 50 50 50 38 63 75 75 50 50 63 63 63 63 63 63 75
21
159709922
Continued table. 2
400
102
200
102
100
102
400
129
200
129
100
129
400
132
132
200
100
132
400
134
200
134
100
134
135
400
400
149
200
149
100
149
400
152
200
152
100
152
400
160
200
160
100
160
Continuation tabl. "2
TGVVCH 50 50 50 38 38 25 63 63 63 38 50 38 38 25 75 75 75 50 75 75 75 63 63 63 50 63 75 75 63 75 75 75 63 50 50 50 50

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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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CH421786|1986-10-22|

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CH421586|1986-10-22|LV930873A| LV5485A3|1986-10-22|1993-06-30|Contrast to obtain 1,5-diphenylpyrazole-3-carbonyl derivatives|

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LTRP1279A| LT2608B|1986-10-22|1993-09-29|1,5-DIFENILPIRAZOL-3-CARBONINE SACRAMENT RECEIVING BUDGET|