CS276704B6 - Method for herbicide agent preparation - Google Patents
Method for herbicide agent preparation Download PDFInfo
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- CS276704B6 CS276704B6 CS422186A CS422186A CS276704B6 CS 276704 B6 CS276704 B6 CS 276704B6 CS 422186 A CS422186 A CS 422186A CS 422186 A CS422186 A CS 422186A CS 276704 B6 CS276704 B6 CS 276704B6
- Authority
- CS
- Czechoslovakia
- Prior art keywords
- acid
- fluorenol
- methyl
- mcpa
- neutralization
- Prior art date
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- 238000000034 method Methods 0.000 title claims abstract description 6
- 238000002360 preparation method Methods 0.000 title claims description 10
- 239000004009 herbicide Substances 0.000 title description 3
- WHKUVVPPKQRRBV-UHFFFAOYSA-N Trasan Chemical compound CC1=CC(Cl)=CC=C1OCC(O)=O WHKUVVPPKQRRBV-UHFFFAOYSA-N 0.000 claims abstract description 27
- 239000005574 MCPA Substances 0.000 claims abstract description 26
- AFMVESZOYKHDBJ-UHFFFAOYSA-N fluoren-9-ol Chemical compound C1=CC=C2C(O)C3=CC=CC=C3C2=C1 AFMVESZOYKHDBJ-UHFFFAOYSA-N 0.000 claims abstract description 19
- 238000006386 neutralization reaction Methods 0.000 claims abstract description 10
- 239000007864 aqueous solution Substances 0.000 claims abstract description 8
- 150000003839 salts Chemical class 0.000 claims abstract description 5
- 239000002253 acid Substances 0.000 claims abstract description 3
- 150000001412 amines Chemical class 0.000 claims abstract description 3
- 238000004090 dissolution Methods 0.000 claims abstract 2
- 230000002363 herbicidal effect Effects 0.000 claims description 13
- GXAMYUGOODKVRM-UHFFFAOYSA-N Flurecol Chemical compound C1=CC=C2C(C(=O)O)(O)C3=CC=CC=C3C2=C1 GXAMYUGOODKVRM-UHFFFAOYSA-N 0.000 claims description 6
- 239000004480 active ingredient Substances 0.000 claims description 4
- 238000003756 stirring Methods 0.000 claims description 3
- 239000012467 final product Substances 0.000 claims 1
- 239000000243 solution Substances 0.000 abstract description 10
- 239000000203 mixture Substances 0.000 abstract description 7
- 238000004519 manufacturing process Methods 0.000 abstract description 6
- 238000009472 formulation Methods 0.000 abstract 1
- ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 description 14
- 238000005660 chlorination reaction Methods 0.000 description 10
- QJVXBRUGKLCUMY-UHFFFAOYSA-N 2-(2-methylphenoxy)acetic acid Chemical compound CC1=CC=CC=C1OCC(O)=O QJVXBRUGKLCUMY-UHFFFAOYSA-N 0.000 description 7
- KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical compound ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 description 4
- 241000196324 Embryophyta Species 0.000 description 4
- 239000005708 Sodium hypochlorite Substances 0.000 description 4
- SUKJFIGYRHOWBL-UHFFFAOYSA-N sodium hypochlorite Chemical compound [Na+].Cl[O-] SUKJFIGYRHOWBL-UHFFFAOYSA-N 0.000 description 4
- PKAUICCNAWQPAU-UHFFFAOYSA-N 2-(4-chloro-2-methylphenoxy)acetic acid;n-methylmethanamine Chemical compound CNC.CC1=CC(Cl)=CC=C1OCC(O)=O PKAUICCNAWQPAU-UHFFFAOYSA-N 0.000 description 3
- 239000013543 active substance Substances 0.000 description 3
- 230000003472 neutralizing effect Effects 0.000 description 3
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- 235000013339 cereals Nutrition 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- 238000010924 continuous production Methods 0.000 description 2
- 125000002147 dimethylamino group Chemical class [H]C([H])([H])N(*)C([H])([H])[H] 0.000 description 2
- 230000005484 gravity Effects 0.000 description 2
- 238000000265 homogenisation Methods 0.000 description 2
- 229910052500 inorganic mineral Inorganic materials 0.000 description 2
- 235000014666 liquid concentrate Nutrition 0.000 description 2
- 239000011707 mineral Substances 0.000 description 2
- 238000002156 mixing Methods 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- BVKZGUZCCUSVTD-UHFFFAOYSA-M Bicarbonate Chemical compound OC([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-M 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- NLZHJOAOIOAZBR-UHFFFAOYSA-N ClC1=CC=C(OCC(=O)O)C=C1.ClC1=CC(=C(OCC(=O)O)C=C1)C Chemical compound ClC1=CC=C(OCC(=O)O)C=C1.ClC1=CC(=C(OCC(=O)O)C=C1)C NLZHJOAOIOAZBR-UHFFFAOYSA-N 0.000 description 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- -1 amine salt Chemical class 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 1
- 239000000460 chlorine Substances 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 238000004817 gas chromatography Methods 0.000 description 1
- 238000011065 in-situ storage Methods 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 150000007522 mineralic acids Chemical class 0.000 description 1
- 238000012544 monitoring process Methods 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- 238000012856 packing Methods 0.000 description 1
- BITYAPCSNKJESK-UHFFFAOYSA-N potassiosodium Chemical compound [Na].[K] BITYAPCSNKJESK-UHFFFAOYSA-N 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 238000011084 recovery Methods 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 159000000000 sodium salts Chemical class 0.000 description 1
- HKNMVNAPCMXVTR-UHFFFAOYSA-M sodium;2-(2-methylphenoxy)acetate Chemical compound [Na+].CC1=CC=CC=C1OCC([O-])=O HKNMVNAPCMXVTR-UHFFFAOYSA-M 0.000 description 1
- 238000003860 storage Methods 0.000 description 1
- 238000012795 verification Methods 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
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- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
Abstract
Predmetom riešenia je spůsob výroby herbi— cídneho přípravku na báze 2-metyl-4T-chlórfenoxyoctovej kyseliny a fluorenolu spočívajúci v tom, že sa do vodného roztoku solí 2-metyl-4-chíórfenoxyoctovej kyseliny pri teplote 15 až 50 θθ za miešania přidá fluorenol a vědný roztok příslušného aminu pričom rozpúšťanie a neutralizácia sa uskutočňuje do pH 7,5 až 8,5.The subject of the solution is the method of production 2-methyl-4T-chlorophenoxyacetic acid based formulation acid and fluorenol based in that it is an aqueous solution of the salts Of 2-methyl-4-chlorophenoxyacetic acid at at a temperature of 15 to 50 ° C with fluorenol added and a known solution of the corresponding amine with dissolution and neutralization are performed to pH 7.5 to 8.5.
Description
Vynález sa týká spósobu výroby herbicídneho přípravku na báze 2-metyl-4-chlórfenoxyoctovej kyseliny (MCPA) a 9-hydroxy-9-fluorenkarboxylovej kyseliny (fluorenolu). Kombinovaný herbicídny prípravok na báze MCPA a fluorenolu je kvapalným koncentrátoru rieditefný vodou. Použitie je určené při pěstovaní obilia v polnohospodárstve, pri pěstovaní obilnin bez podsevu.The invention relates to a process for the preparation of a herbicidal preparation based on 2-methyl-4-chlorophenoxyacetic acid (MCPA) and 9-hydroxy-9-fluorenecarboxylic acid (fluorenol). The combined herbicidal preparation based on MCPA and fluorenol is a water-dilutable liquid concentrator. The use is intended for growing cereals in agriculture, for growing cereals without undersowing.
Kyselina 2-metyl-4-chlórfenoxyoctová a jej soli sa používajú ako velmi účinné herbicidy. Najčastejšie sa připravuje chloráciou 2-metylfenoxyoctovej kyseliny plynným chlóronr pri teplote 95 až 105 °C, ako je opísané v čs. patente č. 91 160. Kontinuálny spůsob chlorácie sodnej, draselnej alebo sodnodraselnej soli 2-metylfenoxyoctovej kyselinyvo vodnom roztoku je opísaný v čs. patente č. 99 892, kontinuálny spósob chlorácie volné 2-metylfenoxyoctovej kyseliny plynným chlórom opisuje čs. patent č. 107 807. Možnost’ kombinácie chlorácie 2-metylfenoxyoctovej kyseliny plynným chlórom a následným dochlórovaním chlórňanom sodným uvádza čs. autorské osvedčenie č. 172 188. Chloráciu 2-metylfenoxyoctovej kyseliny plynným chlórom pri hodnote pH 4 až 6 opisuje francúzsky patent 2 116 256. Chloráciu vodným roztokom chlornanu sodného připraveného vopred alebo in situ v reakčnej zmesi pri teplote 50 °C opisuje patent V. Británie č. 722 625. Chloráciu suspendovanéj 2-metylfenoxyoctovej kyseliny pri hodnote pH rovnej 1 v heterogénnej fáze za přítomnosti kyseliny chlorovodíkovéj chlórňanom sodným při teplote 20 °C opisuje DAS 1- 027 660. Chlorácia sodnej soli 2-metylfenoxyoctovej kyseliny chlórom v přítomnosti hydrouhličitanu je opísaná v patente V. Británie 8.55 504. Výrobu 2-metyl-4chlórfenoxyoctovej kyseliny pomocou chlornanu sodného v přítomnosti minerálnej alebo karboxylovej kyseliny, výrobu 2-metyl-4-chlórfenoxyoctovej kyseliny chloráciou sodnej soli 2-metylfenoxyoctovej kyseliny a získanie 2-metyl-4-chlórfenoxyoctovej kyseliny vyzrážaním s prebytkom vodného roztoku minerálnej kyseliny opisuje čs. autorské osvedčenie č. 179 200.2-Methyl-4-chlorophenoxyacetic acid and its salts are used as very effective herbicides. It is most often prepared by chlorination of 2-methylphenoxyacetic acid with chlorine gas at 95-105 ° C, as described in U.S. Pat. patent no. 91 160. A continuous process for the chlorination of the sodium, potassium or sodium-potassium salt of 2-methylphenoxyacetic acid in aqueous solution is described in U.S. Pat. patent no. No. 99,892, a continuous process for the chlorination of free 2-methylphenoxyacetic acid with chlorine gas describes MS. patent no. 107 807. The possibility of combining the chlorination of 2-methylphenoxyacetic acid with chlorine gas and the subsequent chlorination with sodium hypochlorite is mentioned in MS. author's certificate no. 172 188. Chlorination of 2-methylphenoxyacetic acid with chlorine gas at pH 4 to 6 is described in French Patent 2,116,256. Chlorination with an aqueous solution of sodium hypochlorite prepared in advance or in situ in a reaction mixture at 50 ° C is described in U.S. Pat. 722 625. Chlorination of suspended 2-methylphenoxyacetic acid at pH 1 in a heterogeneous phase in the presence of hydrochloric acid with sodium hypochlorite at 20 ° C is described in DAS 1 027 660. Chlorination of the sodium salt of 2-methylphenoxyacetic acid with chlorine in the presence of bicarbonate is described in U.S. Pat. United Kingdom 8.55 504. Production of 2-methyl-4-chlorophenoxyacetic acid using sodium hypochlorite in the presence of a mineral or carboxylic acid, production of 2-methyl-4-chlorophenoxyacetic acid by chlorination of 2-methylphenoxyacetic acid sodium salt and recovery of 2-methyl-4-chlorophenoxyacetic acid by precipitation with an excess of aqueous mineral acid solution describes MS. author's certificate no. 179 200.
Zistili sme, že selektívny herbicídny účinok MCPA možno výhodné rozšířit’ na odolné dvojdeložné plevely, využitím doplňujúcej účinnej látky fluorenolu.We have found that the selective herbicidal action of MCPA can be advantageously extended to resistant dicotyledonous weeds by the use of the supplementary active ingredient fluorenol.
Soli MCPA sa používajú v polnohospodárstve ako herbicídne přípravky. Podobné dimetylamínová sol’ fluorenolu sa používá ako herbicídny prípravok.MCPA salts are used in agriculture as herbicides. Similar dimethylamine salt of fluorenol is used as a herbicidal composition.
Zistili sme, že je možné vyrobit’ herbicídny prípravok na báze 2-metyl-4-chlórfenoxyoctovej kyseliny (MCPA) a 9-hydroxy-9-fluorenkarboxylovej kyseliny vo formě kvapalného koncentrátu rieditelného vodou. Kombinovaný herbicídny prípravok má selektívny herbicídny účinok MCPA výhodné rozšířený na dvojdeložné plevely, využitím doplňujúcej účinnej látky fluorenolu.We have found that it is possible to prepare a herbicidal composition based on 2-methyl-4-chlorophenoxyacetic acid (MCPA) and 9-hydroxy-9-fluorenecarboxylic acid in the form of a water-dilutable liquid concentrate. The combined herbicidal composition has the selective herbicidal action of MCPA, preferably extended to dicotyledonous weeds, by the use of the supplementary active ingredient fluorenol.
Herbicídny prípravok na báze amínovej soli 2-metyl-4-chlórfenoxyoctovej kyseliny obsahujúci 23,3 až 26,3 % hmotnostných MCPA a 6,75 až 8,25 % hmotnostných fluorenolu sa připravuje tak, že sa do vodného roztoku soli 2-metyl-4-chlórfenoxyoctovej kyseliny při teplote 15 až 50 °C za miešania přidá 9-hydroxy-9-fluorenkarboxylová kyselina a vodný roztok aminu, pričom rozpúšťanie a neutralizácia sa uskutočňuje do pH 7,5 až 8,5.A herbicidal composition based on the amine salt of 2-methyl-4-chlorophenoxyacetic acid containing 23.3 to 26.3% by weight of MCPA and 6.75 to 8.25% by weight of fluorenol is prepared by placing in an aqueous solution of the 2-methyl-4-chlorophenoxyacetic acid salt 4-Chlorophenoxyacetic acid is added 9-hydroxy-9-fluorenecarboxylic acid and an aqueous amine solution at 15-50 [deg.] C. with stirring, dissolving and neutralizing to pH 7.5-8.5.
Proces rozpúšťania fluorenolu v roztoku MCPA, neutralizácia i homogenizácia sa může uskutočniť diskontinuálne alebo kontinuálně. ,The process of dissolving fluorenol in MCPA solution, neutralization and homogenization can be performed batchwise or continuously. ,
Vyšší účinok oproti miešaniu připravených solí spočívá v tom, že sa dá velmi presne nastavit’ poměr účinných látok. Pri tank-mixe dvoch účinných látok vo formě finálnych roztokov v pol’nohospodárstve mohlo dochádzať k nepřesnosti dávkovania poměru účinných látok, alebo bola nutná následná aplikácia.The higher effect than mixing of the prepared salts is that the ratio of active ingredients can be set very precisely. In the case of a tank mix of two active substances in the form of final solutions in agriculture, the dosing ratio of the active substances could be inaccurate or a subsequent application was necessary.
Ďalšou výhodou je, že po neutralizácii MCPA neutralizačným činldlom, například roztokom dimetylamínu, ostal vo výslednom roztoku volný dimetylamín. Přidáním 9-hydroxy-9-fluorenkarboxylovej kyseliny sa volný dimetylamín neutralizuje a stačí přidat’ len časť neutralizačného činidla na doplnenie neutrálneho resp. mierne alkalického prostredia.Another advantage is that after neutralization of the MCPA with a neutralizing agent, such as a dimethylamine solution, free dimethylamine remains in the resulting solution. By adding 9-hydroxy-9-fluorenecarboxylic acid, the free dimethylamine is neutralized and it is sufficient to add only a part of the neutralizing agent to make up the neutral or. slightly alkaline environment.
Výhodou kombinovaného herbicídneho přípravku na báze MCPA a fluorenolu je, že jeden prípravok upravený do formy kvapalného koncentrátu rieditelného vodou obsahuje vo vodném roztoku dve účinné látky, čím sa umožňuje jednorázovou aplikáciou zvýšenie selektívnehoThe advantage of a combined herbicidal preparation based on MCPA and fluorenol is that one preparation formulated in the form of a water-dilutable liquid concentrate contains two active substances in aqueous solution, thus enabling an increase in the selective
CS 276704 Β 6 herbicídneho účinku MCPA. na odolné dvojdeložné plevely.CS 276704 Β 6 herbicidal action of MCPA. for resistant dicotyledonous weeds.
Kombinovaný herbicídny přípravek niože obsahovat’ 1 až 3,6 hmotnostného dielu MCPA ku 1 dielu hmotnostnému fluorenolu vo forme solí rozpustných vo vodě.The combined herbicidal composition may not contain 1 to 3.6 parts by weight of MCPA to 1 part by weight of fluorenol in the form of water-soluble salts.
Příklad 1Example 1
Do 6 1 banky opatrenej miešadlom sa předložilo 2 120 ml (2 459,2 g) 27,5 % vodného roztoku dimetylamínovej soli MCPA o čistotě 83 %. Při teplote 22 °C sa za stálého miešania postupné počas 15 minút přidávalo 200 g fluorenolu o čistotě 95 %. Po přidaní celého množstva fluorenolu sa počas 45 minút přidával 45 % vodný roztok DMA 82 g (91 ml), pričom sa dosiahla hodnota pH = 8. Po dokonalom premiešaní sa stanovil obsah MCPA, ktorý bol 26,7 % a obsah fluorenolu bol 7,5 % hmot. Hustota při 20 °C přípravku bola 1 165 kg.m~\ Připravená vzorka kombinovaného herbicídneho přípravku bola postúpená na biologické pokusy. 'A 6 L flask equipped with a stirrer was charged with 2,120 mL (2,459.2 g) of a 27.5% aqueous solution of dimethylamine salt of MCPA with a purity of 83%. At 22 DEG C., 200 g of 95% pure fluorenol were added gradually over 15 minutes with stirring. After all of the fluorenol had been added, a 45% aqueous DMA solution of 82 g (91 mL) was added over 45 minutes to reach pH = 8. After thorough mixing, the MCPA content was determined to be 26.7% and the fluorenol content to be 7. 5% by weight The density at 20 ° C of the preparation was 1,165 kg.m. A prepared sample of the combined herbicidal preparation was submitted to biological experiments. '
Príklad2 .Example2.
Technologický postup výrobyTechnological process of production
Zo skladového zásobníka sa pomocou čerpadla načerpá do odmerky třikrát po 910 1, tj. 2 730 1 Aminexu Pur o koncentrácii 28 % MCPA stanovenej plynovou chromatografiou. Uvedené množstvo sa samospádem spustí do neutralizačného kotlá. Počas dávkovania Aminexu Pur si obsluha připraví pomocou kladkostroja demag 280 kg flurenolu, tj. 7 vriec po 40 kg. Po vydávkovaní Aminexu Pur sa spustí miešadlo a cirkulačně čerpadlo a začne sa cez násypku dávkovat’ fluorenol.From the storage tank, 910 l are pumped into the measuring cup three times, ie. 2 730 1 Aminex Pur with a concentration of 28% MCPA determined by gas chromatography. Said amount is lowered by gravity into the neutralization boiler. During the dosing of Aminex Pur, the operator prepares 280 kg of flurenol, ie. 7 bags of 40 kg. After dispensing the Aminex Pur, the stirrer and the circulation pump are started and fluorenol is metered through the hopper.
Do odmerky sa z výtlačnej trasy samospádem napustí cca 150 1 45 % dimetylamínu, tj. 30 cm' na stavoznaku odmerky. Po vydávkovaní fluorenolu sa z odmerky odpustí do neutralizačného kotlá cca 100 1 45 % dimetylamínu. Zvyšné množstvo 40 až 50 1 sa z odmerky postupné odpustí za neustálého kontrolovania pH roztoku. Neutralizácia je ukončená při pil = 8. Volný dimetylamín z odmerky a z neutralizačného kotlá je odvzdušnený do absorbčnej kolony sprchovanej vodou. Po ukončení neutralizácie sa vypne odstředivé čerpadlo. Reakčná zmes sa nechá homogenizovať miešadlom ešte 30 min. Po ukončení homogenizácie sa odoberie z neutralizačného kotlá vzorka na stanovenie všetkých kvalitatívnych ukazovatefov na DRA. Produkt sa přečerpá do 50 nP zásobníka, kde sa bude vyrobené množstvo Anitenu MF uskladňovat’. Po vyhovujúcej analýze sa produkt přečerpá cez spádová nádržku do baliarne, kde sa vybalí do nových PE súdkov opatřených etiketou s dátumom výroby, hmotnosťou a číslom šarže po 45 kg do 40 1 a po 55 kg do 50 1 PE súdkov.Approximately 150 l of 45% dimethylamine, ie are filled into the measuring cup by gravity from the discharge line. 30 cm 'on the level indicator. After the fluorenol has been metered in, about 100 l of 45% dimethylamine are discharged from the measuring cup into the neutralization boiler. The remaining amount of 40 to 50 l is gradually released from the measuring cup while constantly monitoring the pH of the solution. The neutralization is completed at pil = 8. The free dimethylamine from the measuring cup and from the neutralization boiler is vented to an absorption column sprayed with water. At the end of the neutralization, the centrifugal pump is switched off. The reaction mixture was allowed to homogenize with a stirrer for another 30 min. At the end of the homogenisation, a sample is taken from the neutralization boiler to determine all the qualitative indicators for DRA. The product is pumped into a 50 nP tank where the amount of Anitene MF produced will be stored ’. After satisfactory analysis, the product is pumped through a drop tank to the packing plant, where it is unpacked into new PE drums provided with a label with the date of manufacture, weight and batch number of 45 kg to 40 l and 55 kg to 50 1 PE drums.
V overovacej výrobě Anitenu MF sa vyrobilo 141,570 t. Při velkosti šarže 50 t uvedené množstvo reprezentuje 3 šarže.141,570 tons were produced in the verification production of Aniten MF. For a batch size of 50 t, this quantity represents 3 batches.
Tabulka č. 1Table no. 1
Prehl’ad kvality vyrobeného Anitenu MFOverview of the quality of manufactured Aniten MF
CS 276704 B 6CS 276704 B 6
Claims (1)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CS422186A CS276704B6 (en) | 1986-06-09 | 1986-06-09 | Method for herbicide agent preparation |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CS422186A CS276704B6 (en) | 1986-06-09 | 1986-06-09 | Method for herbicide agent preparation |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CS8604221A1 CS8604221A1 (en) | 1990-10-12 |
| CS276704B6 true CS276704B6 (en) | 1992-07-15 |
Family
ID=5384466
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CS422186A CS276704B6 (en) | 1986-06-09 | 1986-06-09 | Method for herbicide agent preparation |
Country Status (1)
| Country | Link |
|---|---|
| CS (1) | CS276704B6 (en) |
-
1986
- 1986-06-09 CS CS422186A patent/CS276704B6/en unknown
Also Published As
| Publication number | Publication date |
|---|---|
| CS8604221A1 (en) | 1990-10-12 |
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