CS201694B1 - 2,4-oxycellulose-6-/x/-s-triazines and method of their preparing - Google Patents
2,4-oxycellulose-6-/x/-s-triazines and method of their preparing Download PDFInfo
- Publication number
- CS201694B1 CS201694B1 CS312778A CS312778A CS201694B1 CS 201694 B1 CS201694 B1 CS 201694B1 CS 312778 A CS312778 A CS 312778A CS 312778 A CS312778 A CS 312778A CS 201694 B1 CS201694 B1 CS 201694B1
- Authority
- CS
- Czechoslovakia
- Prior art keywords
- oxycellulose
- nitro
- cellulose
- triazines
- hydrazone
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 7
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims description 12
- 229920002678 cellulose Polymers 0.000 claims description 10
- 239000001913 cellulose Substances 0.000 claims description 10
- -1 5-nitrofurfurylideneacetone hydrazone Chemical compound 0.000 claims description 8
- 239000000463 material Substances 0.000 claims description 8
- 239000004744 fabric Substances 0.000 claims description 7
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims description 6
- FUBFWTUFPGFHOJ-UHFFFAOYSA-N 2-nitrofuran Chemical class [O-][N+](=O)C1=CC=CO1 FUBFWTUFPGFHOJ-UHFFFAOYSA-N 0.000 claims description 5
- 239000000123 paper Substances 0.000 claims description 3
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 claims description 2
- 239000000835 fiber Substances 0.000 claims description 2
- 239000003960 organic solvent Substances 0.000 claims description 2
- JYEUMXHLPRZUAT-UHFFFAOYSA-N 1,2,3-triazine Chemical compound C1=CN=NN=C1 JYEUMXHLPRZUAT-UHFFFAOYSA-N 0.000 claims 1
- TWQHWVOTBAQIRT-UHFFFAOYSA-N 3-(5-nitrofuran-2-yl)prop-2-enylidenehydrazine Chemical compound NN=CC=CC1=CC=C([N+]([O-])=O)O1 TWQHWVOTBAQIRT-UHFFFAOYSA-N 0.000 claims 1
- 150000007857 hydrazones Chemical class 0.000 claims 1
- 238000006467 substitution reaction Methods 0.000 description 11
- 230000000845 anti-microbial effect Effects 0.000 description 6
- 239000013543 active substance Substances 0.000 description 5
- 230000015556 catabolic process Effects 0.000 description 4
- 238000006731 degradation reaction Methods 0.000 description 4
- 238000002360 preparation method Methods 0.000 description 4
- RAWYBMUWBNFLAS-UHFFFAOYSA-N (5-nitrofuran-2-yl)methylidenehydrazine Chemical compound NN=CC1=CC=C([N+]([O-])=O)O1 RAWYBMUWBNFLAS-UHFFFAOYSA-N 0.000 description 3
- 229920000742 Cotton Polymers 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 239000000834 fixative Substances 0.000 description 3
- HGINCPLSRVDWNT-UHFFFAOYSA-N Acrolein Chemical compound C=CC=O HGINCPLSRVDWNT-UHFFFAOYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
- 238000009833 condensation Methods 0.000 description 2
- 230000005494 condensation Effects 0.000 description 2
- 230000000813 microbial effect Effects 0.000 description 2
- 239000002689 soil Substances 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- SXINBFXPADXIEY-UHFFFAOYSA-N 5-Nitrofurfural Chemical compound [O-][N+](=O)C1=CC=C(C=O)O1 SXINBFXPADXIEY-UHFFFAOYSA-N 0.000 description 1
- 229920001817 Agar Polymers 0.000 description 1
- 241000228245 Aspergillus niger Species 0.000 description 1
- 229920003043 Cellulose fiber Polymers 0.000 description 1
- 241000233866 Fungi Species 0.000 description 1
- MGJKQDOBUOMPEZ-UHFFFAOYSA-N N,N'-dimethylurea Chemical compound CNC(=O)NC MGJKQDOBUOMPEZ-UHFFFAOYSA-N 0.000 description 1
- GXCLVBGFBYZDAG-UHFFFAOYSA-N N-[2-(1H-indol-3-yl)ethyl]-N-methylprop-2-en-1-amine Chemical class CN(CCC1=CNC2=C1C=CC=C2)CC=C GXCLVBGFBYZDAG-UHFFFAOYSA-N 0.000 description 1
- 241000287219 Serinus canaria Species 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 239000008272 agar Substances 0.000 description 1
- 229940027988 antiseptic and disinfectant nitrofuran derivative Drugs 0.000 description 1
- 239000010866 blackwater Substances 0.000 description 1
- 238000009933 burial Methods 0.000 description 1
- 229920003086 cellulose ether Polymers 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- MGNCLNQXLYJVJD-UHFFFAOYSA-N cyanuric chloride Chemical compound ClC1=NC(Cl)=NC(Cl)=N1 MGNCLNQXLYJVJD-UHFFFAOYSA-N 0.000 description 1
- 230000001419 dependent effect Effects 0.000 description 1
- 230000006866 deterioration Effects 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- PLHJDBGFXBMTGZ-WEVVVXLNSA-N furazolidone Chemical compound O1C([N+](=O)[O-])=CC=C1\C=N\N1C(=O)OCC1 PLHJDBGFXBMTGZ-WEVVVXLNSA-N 0.000 description 1
- 229960001625 furazolidone Drugs 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- WJRBRSLFGCUECM-UHFFFAOYSA-N hydantoin Chemical compound O=C1CNC(=O)N1 WJRBRSLFGCUECM-UHFFFAOYSA-N 0.000 description 1
- 229940091173 hydantoin Drugs 0.000 description 1
- GDYGDIFVJJFISN-UHFFFAOYSA-N hydrazine;1,3,5-triazine Chemical class NN.C1=NC=NC=N1 GDYGDIFVJJFISN-UHFFFAOYSA-N 0.000 description 1
- 230000005923 long-lasting effect Effects 0.000 description 1
- 244000005700 microbiome Species 0.000 description 1
- 244000005706 microflora Species 0.000 description 1
- IAIWVQXQOWNYOU-UHFFFAOYSA-N nitrofurazone Chemical compound NC(=O)NN=CC1=CC=C([N+]([O-])=O)O1 IAIWVQXQOWNYOU-UHFFFAOYSA-N 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 239000000546 pharmaceutical excipient Substances 0.000 description 1
- FJOHZGNAXVQGAE-UHFFFAOYSA-N prop-2-enylidenehydrazine Chemical compound NN=CC=C FJOHZGNAXVQGAE-UHFFFAOYSA-N 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
- 230000004584 weight gain Effects 0.000 description 1
- 235000019786 weight gain Nutrition 0.000 description 1
Landscapes
- Treatments For Attaching Organic Compounds To Fibrous Goods (AREA)
Description
(54) 2,4 — oxycelulózo — 6 — (x) — S — triazíny a spósob ich přípravy(54) 2,4-Oxycellulose-6 - (x) - S - triazines and process for their preparation
Vynález sa týká 2,4 — oxycelulózo (x) — S — triazínov obecného vzorca I.The invention relates to 2,4-oxycellulose (x) - S-triazines of the formula I.
0- celulózo, i //'''k eN”Cl7(CH=GH)n CeN”NH ~ m'1'1 (I) íO-cellulose, // k k e Cl Cl Cl 7 CH (CH = GH) n CeN NH NH m m 1 1 1 1 (I) í
a sposobu ich přípravy.and how to prepare them.
Technické materiály n-a báze celulózy majú nedostatok v tom, že sa nevyznačujú antimikrobiálnymi vlastnosfemi a nie sú odolné voči rozkladnému účinku mikroorganizmov. Tieto požadované vlastnosti je možno docieliť antimikrobiálnou úpravou; impregnáciou účinnými látkami a pre dlhotrvajúci účinok je účelné účinné látky viazať chemickou vazbou. Na antimikrobiálnu úpravu obidvoma spósobmi sa vyúžívajú početné preparáty, ktorých použitie je závislé od účelu a sposobu použitia celulózového materiálu.The technical materials of n-a cellulose base have the drawback that they do not exhibit antimicrobial properties and are not resistant to the degradation effect of microorganisms. These desired properties can be achieved by antimicrobial treatment; By impregnating the active substances and for a long-lasting effect, it is expedient to bind the active substances by chemical bonding. Numerous preparations are used for antimicrobial treatment in both ways, the use of which is dependent on the purpose and method of use of the cellulosic material.
Pri antimikrobiálnej úpravě celulózových materiálov našli uplatnenie aj niektoré 5 — nitrofuránové deriváty. 5 — Nitro — 2-furaldehyd a 3-/ 5 — nitro — 2 — furyl/akroleín sa vyúžívajú pri vláknech z celulózy a niekto201694 rýoh jej esterov a ako přídavné látky sa používajú furagin /1- /3 — /5- nitro- 2 — furyl alkylamino/ hydantoin/, fura-zolidon/ 3- /5nitro- 2 — furfurylidenamino/ oxazolidon/ a 5- nitro — 2 — furaldehydsemikařbazon/.Some 5 - nitrofuran derivatives have also found application in the antimicrobial treatment of cellulosic materials. 5-Nitro-2-furaldehyde and 3- (5-nitro-2-furyl / acrolein) are used in cellulose fibers and some of the ester esters and furagine / 1- / 3 - / 5-nitro-2 are used as additives. Furyl alkylamino (hydantoin), furazolidone (3- (5-nitro-2-furfurylideneamino) oxazolidone) and 5-nitro-2-furaldehyde semicarbazone).
Z híadiska praktickej aplikácie je taktiež dóležité zaviesť biologicky účinné látky na celulózu spoločne s dalšími pomocnými látkami tak, aby sa nezvyšoval počet technologických operácií a nevznikali nové nároky na technologické zariadenie. V tomto zmysle sa účinné látky s výhodou fixuj ú spoločne s dimetylmočovimou a často sa využívá reaktívny 2, 4, 6 — trichlór — S — triazín, pomocou ktorého sa na celulózu fixoval celý rad účinných látok [Paul-us W., Pauli O., Textilveredelung 5,(4) 247 (1970)].From a practical point of view, it is also important to introduce biologically active substances for cellulose together with other excipients so as not to increase the number of technological operations and to create new demands on the technological equipment. In this sense, the active substances are preferably fixed together with dimethyl urea, and the reactive 2,4,6-trichloro-S-triazine is often used to fix a wide range of active substances to cellulose [Paul-us W., Pauli O. , Textilveredelung 5, (4) 247 (1970)].
— Nitrofuránové deriváty týmto spósobom na celulózu doteraz fixované neboli.- Nitrofuran derivatives have not yet been fixed to cellulose in this way.
Podstata spósobu přípravy 2,4 — oxycelulózo — 6 — (x) — S-<triazínov podlá vynálezu spočívá v tom, že na celulózové materiály vo formě vlákien, papiera alebo tkaniv sa pósobí 5 — nitrofuránovými derivátmi 2,4 — diohlór — 6 — hydrazín — S — triazinů obecného vzorca II.The process according to the invention for the preparation of 2,4-oxycellulose-6 - (x) - S - triazines consists in the treatment of cellulosic materials in the form of fibers, paper or tissues with 5-nitrofuran derivatives of 2,4-diohloro-6 -. hydrazine - S - triazines of formula II.
0aN0 and N
-(CHs=CH)n- G-N-NH- (CH 3 = CH) n - GN-NH
1«) kde pre n rovné 0 R je H n rovné 1 R je H, CH3 v prostředí organických rozpúšťadiel s výhodou acetonu, dioxanu, octanu etylového pri teplotách od 20 °C do 170 °C.Wherein n is equal to 0 R is H n is equal to 1 R is H, CH 3 in an organic solvent medium preferably acetone, dioxane, ethyl acetate at temperatures from 20 ° C to 170 ° C.
(i)(I)
0- celulózaO- cellulose
OgN-γ ^-(CH»CHjg C-N-Nh/QOgN- [gamma] - (CH3CH3 ) CN-Nh / Q
0-eelwlóta (n)0-watt (n)
Cl N~íi kde n a R je hoře uvedené.C ~ N II wherein the R indicated above.
Výhodou spósobu přípravy derivátov podl’a vynálezu je, že sa 5 — nitrofuránové deriváty 2,4 — diohlór — 6 — hydrazín — S — triazínu viažu na celulózu za podmienok běžných pri úpravě celulózových materiálov.An advantage of the process for the preparation of the derivatives according to the invention is that the 5-nitrofuran derivatives of 2,4-dihalo-6-hydrazine-S-triazine bind to cellulose under the conditions customary in the treatment of cellulosic materials.
Příklad 1Example 1
Bavlněná doprovodná tkanina sa naklocuje s 2 %-ným roztokom látky typu 1 v acetone, aceton sa odpaří a tkanina sa ponoří do fixačného kúpela obsíahujúceho 50 g/dm3 chloridu sodného a 10 g/dm3 kyslého uhličitanu sodného. Po vysušení pri 70 °C sa tkanina zahrieva 10 minút pri 160 °C, po oohladení sa čistí praním vo vodě a axtrakciou acetónom v soxletovom aparáte. Získal sa di-/2,4 — oxycelulózo — 6 — /5 — nitro — 2 — furaldehydrazón/ — S — triazín so SS 0,021, di —/2,4 — oxycelulózo — 6 — (3) 5 — nitro — 2 — furylakroleínhydrazón) — S — triazín so SS 0,020 a di-,/2,4- oxycelulózo — 6 — (5— nitro — furfurylidenacetónhydrazón) — S — triazín so SS 0,027.The cotton backing fabric is covered with a 2% solution of type 1 substance in acetone, the acetone is evaporated and the fabric is immersed in a fixative bath containing 50 g / dm 3 sodium chloride and 10 g / dm 3 sodium bicarbonate. After drying at 70 ° C, the fabric is heated for 10 minutes at 160 ° C, after cooling it is cleaned by washing in water and by acetone axtraction in a soxlet apparatus. Di- [2,4-oxycellulose-6- [5-nitro-2-furaldehyde] -S-triazine with SS 0.021 was obtained, di- [2,4-oxycellulose-6- (3) 5-nitro-2- furylacrolein hydrazone) - S - triazine with SS 0,020 and di -, [2,4-oxycellulose - 6- (5-nitro - furfurylideneacetonehydrazone) - S - triazine with SS 0,027.
Příklad 2Example 2
Spósobom uvedeným v příklade 1. sa vykoná kondenzácia pri použití papiera Whatman.The condensation was performed as in Example 1 using Whatman paper.
Získal sa di — /2,4 — oxycelulózo — 6-/5nitro- 2- furaldehydhydrazón/ — S — triazín so SS 0,16, di- /2,4 — oxycelulózo — 6 — /3-/5 — nitro — 2 — furyl/ akroleínhydrazón/ — S — triazín so SS 0,018 a di-/2,4 — oxycelulózo — 6-/5 — nitrofurfurylidenacetónhydrazón/-S-triazín so SS 0,028.Di - (2,4-oxycellulose - 6- (5-nitro-2-furaldehydehydrazone) - S - triazine with SS 0.16 was obtained, di- / 2,4-oxycellulose - 6 - / 3- / 5-nitro-2 - furyl (acrolein hydrazone) - S - triazine with SS 0.018 and di- (2,4-oxycellulose - 6- (5-nitrofurfurylideneacetonehydrazone) -S-triazine with SS 0,028.
Příklad 3Example 3
Bavlněná doprovodná tkanina sa naklocuje 10 %-ným roztokom 2, 4 — dichlór — 6 — /5 — nitro — 2 — furaldehydhydrazón/ — S — triazinů v acetone, ponoří sa do fixačného kúpela ako v příklade 1. a kondenzácia sa vykoná zahrievaním pri 50 °C v priebehu troch hodin. Tkanina sa čistí spósobom uvedeným v příklade 1.The cotton backing fabric is covered with a 10% solution of 2,4-dichloro-6- (5-nitro-2-furaldehyde hydrazone) -S-triazines in acetone, immersed in a fixative bath as in Example 1. and condensation is performed by heating at 50 ° C over three hours. The fabric is cleaned as described in Example 1.
Získal s'a di — (2,4 — oxycelulózo — 6 — /5 — nitro — 2 — furaldehydhydrazón/ -rS — triazín so SS 0,005.Obtained with di - (2,4-oxycellulose-6- [5-nitro-2-furaldehyde hydrazone) -rS-triazine with SS 0.005.
Příklad 4Example 4
Bavlněná doprovodná tkanina sa naklocuje ako v příklade 3, ponoří do fixačného kúpela obsahujúceho Na2HPO4 . 2H2O (17,8 g/dm3) a NaOH (17,2 g/dm3) a potom sa zahrieva jednu hodinu pri 50 °C. Čistí sa spósobom uvedeným v příklade 1. 'The cotton backing fabric is tilted as in Example 3, immersed in a Na 2 HPO 4- containing fixative bath. 2H 2 O (17.8 g / dm 3 ) and NaOH (17.2 g / dm 3 ) and then heated at 50 ° C for one hour. Purified as in Example 1. '
Získal sa di — /oxycelulózo — 6 — /5 — nitro — 2 — furaldehydhydrazón/ — S — triazín so SS 0,008.Di - (oxycellulose - 6- (5 - nitro - 2 - furaldehyde hydrazone) - S - triazine with SS 0.008 was obtained.
Obsah naviazaného 5 — nitrofuránového derivátu sa zisťoval z prírastku na hmotnosti, respektive z obsahu dusíka určeného modifikovanou Kjehdalovou metodou modifikovanou podlá (Šlionskaja M. A., Nogteva K. G., Poliščuk B. O., Volf L. A., Ohim. volokna 15 (3) 70 (1973) a je vyjádřený ako stupeň substitúcie.The bound 5-nitrofuran derivative content was determined from the weight gain and nitrogen content determined by the modified Kjehdal method modified according to (Shlionkaya MA, Nogteva KG, Polishchuk BO, Volf LA, Ohim volokna 15 (3) 70 (1973) and expressed as a degree of substitution.
Vzniklé celulózové etéry majú pri stupni substitúcie (SS) 0,002 až 0,067 kanárikovožltú farbu. Pri antimikrobiálnych testoch sa vy3 značujú účinnosťou na Aspergillus niger na kontaminovanom sladinkovom agare, odolnosťou voči rozkladným hubám za tropikalizačných podmienok v trvaní 60 dní, odolnosťou voči rozkladnej činnosti aerobnej pódnej mikroflóry (čiernozem, Čierna voda pri Bratislavě) v priebehu 28 dní a rozkladnej činnosti anaerobnej pódnej mikroflóry (soil burial test) v priebehu 28 dní.The resulting cellulose ethers have a canary yellow color at a degree of substitution (SS) of 0.002 to 0.067. In antimicrobial tests, they are characterized by efficacy on Aspergillus niger on contaminated malt agar, resistance to degradation fungi under tropical conditions for 60 days, resistance to degradation activity of aerobic soil microflora (black earth, Black water near Bratislava) for 28 days and anaerobic degradation activity. soil burial test within 28 days.
Výsledky mikrobiálnych testov naznačujú, že tieto celulózové deriváty sa móžu uplatnit ako materiály odolné voči mikrobiálnej deteriorácii a ako materiály s antimikrobiálnymi účinkami vo svojom bezprostrednom okolí.The results of microbial tests indicate that these cellulose derivatives can be used as materials resistant to microbial deterioration and as materials with antimicrobial effects in their immediate vicinity.
Claims (2)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CS312778A CS201694B1 (en) | 1978-05-16 | 1978-05-16 | 2,4-oxycellulose-6-/x/-s-triazines and method of their preparing |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CS312778A CS201694B1 (en) | 1978-05-16 | 1978-05-16 | 2,4-oxycellulose-6-/x/-s-triazines and method of their preparing |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CS201694B1 true CS201694B1 (en) | 1980-11-28 |
Family
ID=5370413
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CS312778A CS201694B1 (en) | 1978-05-16 | 1978-05-16 | 2,4-oxycellulose-6-/x/-s-triazines and method of their preparing |
Country Status (1)
| Country | Link |
|---|---|
| CS (1) | CS201694B1 (en) |
-
1978
- 1978-05-16 CS CS312778A patent/CS201694B1/en unknown
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| DE2560591C2 (en) | ||
| RU2035140C1 (en) | Fungicidal composition and seeding material protection method | |
| Maude et al. | The control of fungal seed–borne diseases by means of a thiram seed soak | |
| SU1338783A3 (en) | Method of producing derivatives of diphenyl ester | |
| SU518105A3 (en) | Fungicide | |
| Khan et al. | Application of chemicals in organic solvents to dry seeds | |
| DE2741437A1 (en) | ANILINE DERIVATIVES, METHOD FOR THEIR PRODUCTION AND PEST CONTROL | |
| Johnston et al. | Effects of some growth regulators on tiller bud elongation in cereals | |
| CS201694B1 (en) | 2,4-oxycellulose-6-/x/-s-triazines and method of their preparing | |
| CN111393543A (en) | Cyclodextrin derivatives, herbicides coated with cyclodextrin derivatives and preparation method and application | |
| DE2902832A1 (en) | MICROBICIDAL AGENTS | |
| US4936899A (en) | Abscission of parts of plants | |
| SU965338A3 (en) | Herbicidal composition | |
| CA1220482A (en) | Unsaturated 1,4-diketones having fungicide activity | |
| SU1428175A3 (en) | Method of controlling growth of cereals | |
| CN106070263B (en) | 5- amino -1H- Bi Zuos &#91;3,4-d&#93;Application of pyrimidine -4 (5H) the -one class compound in preparing anti-plant virus agent | |
| US3355352A (en) | Fungicidal composition | |
| US5512673A (en) | Physiologically active substances of plant, process for the preparation thereof, and utilities thereof | |
| US5169643A (en) | Thiolcarbamate granule formulation | |
| SU1138098A1 (en) | Method of presowing treatment of cotton seeds | |
| US4085220A (en) | 2-Alkenyl-N-[(trichloromethyl)thio]succinimides | |
| AT325889B (en) | HERBICIDAL AND FUNGICIDAL AGENT | |
| DE2919825A1 (en) | MICROBICIDAL AGENT | |
| JPS5531098A (en) | 1-acyl-3-(3,5-dihalogenophenyl)-hydantoin derivative, its preparation, and agricultural and horticultural fungicide comprising it as active constituent | |
| AT368682B (en) | METHOD FOR CONTROLLING MUSHROOM INFECTIONS IN CROPS |