DE1919180C3 - Substituted methylsulfenic acid amides, processes for their preparation and agents containing them - Google Patents
Substituted methylsulfenic acid amides, processes for their preparation and agents containing themInfo
- Publication number
- DE1919180C3 DE1919180C3 DE19691919180 DE1919180A DE1919180C3 DE 1919180 C3 DE1919180 C3 DE 1919180C3 DE 19691919180 DE19691919180 DE 19691919180 DE 1919180 A DE1919180 A DE 1919180A DE 1919180 C3 DE1919180 C3 DE 1919180C3
- Authority
- DE
- Germany
- Prior art keywords
- preparation
- substituted
- methylsulfenic
- processes
- acid amides
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired
Links
- XOVSRHHCHKUFKM-UHFFFAOYSA-N S-methylthiohydroxylamine Chemical class CSN XOVSRHHCHKUFKM-UHFFFAOYSA-N 0.000 title claims 2
- 238000000034 method Methods 0.000 title description 5
- 238000002360 preparation method Methods 0.000 title description 3
- 239000003795 chemical substances by application Substances 0.000 title 1
- 125000000896 monocarboxylic acid group Chemical group 0.000 description 10
- FJKROLUGYXJWQN-UHFFFAOYSA-N 4-Hydroxybenzoic acid Chemical compound OC(=O)C1=CC=C(O)C=C1 FJKROLUGYXJWQN-UHFFFAOYSA-N 0.000 description 6
- YGSDEFSMJLZEOE-UHFFFAOYSA-N Salicylic acid Chemical compound OC(=O)C1=CC=CC=C1O YGSDEFSMJLZEOE-UHFFFAOYSA-N 0.000 description 6
- 239000002253 acid Substances 0.000 description 6
- HEMHJVSKTPXQMS-UHFFFAOYSA-M sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- YXFVVABEGXRONW-UHFFFAOYSA-N toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- 239000004480 active ingredient Substances 0.000 description 3
- 239000011230 binding agent Substances 0.000 description 3
- 150000005165 hydroxybenzoic acids Chemical class 0.000 description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- 229960004889 salicylic acid Drugs 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 2
- 229940090248 4-hydroxybenzoic acid Drugs 0.000 description 2
- MVPPADPHJFYWMZ-UHFFFAOYSA-N Chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- 239000004599 antimicrobial Substances 0.000 description 2
- UHOVQNZJYSORNB-UHFFFAOYSA-N benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 2
- 239000007795 chemical reaction product Substances 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- -1 fluorocarbonyl Chemical group 0.000 description 2
- 229910052739 hydrogen Inorganic materials 0.000 description 2
- 239000001257 hydrogen Substances 0.000 description 2
- 125000004435 hydrogen atoms Chemical group [H]* 0.000 description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
- 150000003839 salts Chemical class 0.000 description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L sodium carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- 239000011780 sodium chloride Substances 0.000 description 2
- 238000004659 sterilization and disinfection Methods 0.000 description 2
- ZMANZCXQSJIPKH-UHFFFAOYSA-N triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 2
- RPAJWWXZIQJVJF-UHFFFAOYSA-N 2,4-dichloro-6-(3,5-dichloro-2-hydroxyphenyl)sulfinylphenol Chemical compound OC1=C(Cl)C=C(Cl)C=C1S(=O)C1=CC(Cl)=CC(Cl)=C1O RPAJWWXZIQJVJF-UHFFFAOYSA-N 0.000 description 1
- ICSNLGPSRYBMBD-UHFFFAOYSA-N 2-Aminopyridine Chemical compound NC1=CC=CC=N1 ICSNLGPSRYBMBD-UHFFFAOYSA-N 0.000 description 1
- KRHYYFGTRYWZRS-UHFFFAOYSA-N HF Chemical compound F KRHYYFGTRYWZRS-UHFFFAOYSA-N 0.000 description 1
- FFRBMBIXVSCUFS-UHFFFAOYSA-N Martius yellow Chemical compound C1=CC=C2C(O)=C([N+]([O-])=O)C=C([N+]([O-])=O)C2=C1 FFRBMBIXVSCUFS-UHFFFAOYSA-N 0.000 description 1
- PUFGEEHFTRCGRD-UHFFFAOYSA-N N-phenyl-N-(trifluoromethyl)carbamoyl fluoride Chemical class FC(=O)N(C(F)(F)F)C1=CC=CC=C1 PUFGEEHFTRCGRD-UHFFFAOYSA-N 0.000 description 1
- ABBQHOQBGMUPJH-UHFFFAOYSA-M Sodium salicylate Chemical compound [Na+].OC1=CC=CC=C1C([O-])=O ABBQHOQBGMUPJH-UHFFFAOYSA-M 0.000 description 1
- 239000000370 acceptor Substances 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 150000001447 alkali salts Chemical class 0.000 description 1
- QGZKDVFQNNGYKY-UHFFFAOYSA-O ammonium group Chemical group [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 description 1
- 230000000845 anti-microbial Effects 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 150000001735 carboxylic acids Chemical class 0.000 description 1
- 238000002512 chemotherapy Methods 0.000 description 1
- 150000001805 chlorine compounds Chemical class 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 230000000875 corresponding Effects 0.000 description 1
- 230000000249 desinfective Effects 0.000 description 1
- 239000003085 diluting agent Substances 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- 230000000855 fungicidal Effects 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- 229910000040 hydrogen fluoride Inorganic materials 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 150000005419 hydroxybenzoic acid derivatives Chemical class 0.000 description 1
- 238000002955 isolation Methods 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 1
- PMZURENOXWZQFD-UHFFFAOYSA-L na2so4 Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N o-xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- 238000004321 preservation Methods 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 239000001187 sodium carbonate Substances 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- PUZPDOWCWNUUKD-UHFFFAOYSA-M sodium fluoride Inorganic materials [F-].[Na+] PUZPDOWCWNUUKD-UHFFFAOYSA-M 0.000 description 1
- 229960004025 sodium salicylate Drugs 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 230000001954 sterilising Effects 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
Description
co-o-zco-o-z
in welcher R für Wasserstoff, Methyl, Methoxy oder Nitro und Z für Wasserstoff, Methyl, ein Metall-Äquivalent oder die Ammoniumgruppe steht.in which R is hydrogen, methyl, methoxy or nitro and Z is hydrogen, methyl Metal equivalent or the ammonium group.
2. Verfahren zur Herstellung der Verbindungen gemäß Anspruch 1, dadurch gekennzeichnet, daß man in an sich bekannter Weise Fluorcarbonyl-N -{trihalogenmethyll hio)- N - trifluonnethylaniline der Formel2. Process for the preparation of the compounds according to claim 1, characterized in that one in a conventional manner fluorocarbonyl-N - {trihalogenmethyll hio) - N - trifluonnethylaniline the formula
R COFR COF
CI2FC-S-N-Hl- J
CF3 CI 2 FC-SN-Hl- J
CF 3
mit Hydroxybenzoesäuren bzw. deren Derivaten der Formelwith hydroxybenzoic acids or their derivatives of the formula
co—ο—ζco — ο — ζ
(HIl(HIl
in Gegenwart eines säurebindenden Mittols umsetzt und gegebenenfalls die Carbonsäuren in die entsprechenden Salze überführt.implemented in the presence of an acid-binding Mittols and optionally converting the carboxylic acids into the corresponding salts.
3. Antimikrobielle Mittel, gekennzeichnet durch einen Gehalt an einer Verbindung gemäß Anspruch 1.3. Antimicrobial agents, characterized by a content of a compound according to claim 1.
4545
Es ist bereits bekannt, daß Hydroxybenzoesäuren, z. B. die Salicyl- und die 4-Hydroxybenzoesäure oder Derivate dieser Säuren als antimikrobielle Mittel auf den verschiedensten Gebieten verwendet werden (K. H. W a 11 h ä u ß e r und H. Schmidt: Sterilisation, Desinfektion, Konservierung, Chemotherapie, Georg Thieme-Verlag, Stuttgart, 1967, S. 168). Außerdem ist die fungizide Wirksamkeit von N-Fluordichlormetlhylthio - Verbindungen auf dem Pflanzenschutz- und Materialschutzsektor bekannt (vgl. die deutschen Patentschriften 11 93 498 und 11 80 486).It is already known that hydroxybenzoic acids, e.g. B. the salicylic and 4-hydroxybenzoic acid or Derivatives of these acids are used as antimicrobial agents in a wide variety of fields (K. H. W a 11 h ä u ß e r and H. Schmidt: Sterilization, Disinfection, preservation, chemotherapy, Georg Thieme-Verlag, Stuttgart, 1967, p. 168). Besides that is the fungicidal effectiveness of N-fluorodichloromethylthio - Known connections in the crop protection and material protection sector (cf. German patents 11 93 498 and 11 80 486).
Demgegenüber betrifft die Erfindung den in den Ansprüchen definierten Gegenstand.In contrast, the invention relates to the subject matter defined in the claims.
überraschenderweise zeigen die erfindungsgemäßen an der Hydroxygruppe substituierten Hydroxybenzoesäurederivate eine erheblich höhere antimikrobielle Wirkung als die aus dem Stand der Technik bekannte Salicylsäure und die 4-Hydroxybenzoesäure. welche die chemisch nächstliegenden Wirkstoff gleicher Wirkungsart sind. Sie stellen somit eine wesentliche Bereicherung der Technik dar.The hydroxybenzoic acid derivatives according to the invention which are substituted on the hydroxy group surprisingly show a significantly higher antimicrobial effect than that known from the prior art Salicylic acid and 4-hydroxybenzoic acid. which are the chemically closest active ingredients of the same type of action are. They therefore represent an essential enrichment of the technology.
Der Reaktionsverlauf des Verfahrens läßt sich bei der Verwendung von 4-Fluorcarbonyl-N-(fluordichlonnethylihio)-N-tkifluormethylanilin und Salicylsäure als Reaktionspartner durch das folgende Schema wiedergegeben:The course of the reaction in the process can be determined when using 4-fluorocarbonyl-N- (fluorodichlonnethylihio) -N-tkifluoromethylaniline and salicylic acid as reactants represented by the following scheme:
CUFC-S —CUFC-S -
+ NaOH
-NaF+ NaOH
-NaF
CUFC-S-NCUFC-S-N
/\y/ \ y
HOOCHOOC
Die als Ausgangskomponenten zu verwendenden Fluorcarbonyl - N - (trihalogenmelhyfthio) - N - trifluormethylaniline sind bekannt, sie werden aus Fluorcarbonyl - N - trifluormethylanilinen und SuI-fensäurechloriden hergestellt (vgl. belgische Patentschrii 6 99 033). Die als Ausgangsstoffe zu verwendenden Hydroxybenzoesäuren bzw. deren Derivate sind durch die Formel III definiert.The fluorocarbonyl - N - (trihalogenmelhyfthio) - N - trifluoromethylanilines to be used as starting components are known, they are made from fluorocarbonyl - N - trifluoromethylanilines and sulphene acid chlorides manufactured (see Belgian patent 6 99 033). Those to be used as starting materials Hydroxybenzoic acids and their derivatives are defined by the formula III.
Als Verdünnungsmittel kommen Wasser, Ketone, wie Aceton. Äther, wie Diäthyläther, Dioxan und aromatische (gegebenenfalls chlorierte) Kohlenwasserstoffe, wie Benzol, Toluol, Xylol, Chlorbenzol, in Frage.The diluents used are water, ketones, such as acetone. Ethers such as diethyl ether, dioxane and aromatic (optionally chlorinated) hydrocarbons, such as benzene, toluene, xylene, chlorobenzene, in Ask.
Als Säurebinder können alle üblichen für Fluorwasserstoff geeigneten Akzeptoren Verwendung finden. Vorzugsweise verwendet man Natriumhydroxid. Kaliumhydroxid, Natriumcarbonat, Pyridin oder Triäthylamin. All customary acceptors suitable for hydrogen fluoride can be used as acid binders. Sodium hydroxide is preferably used. Potassium hydroxide, sodium carbonate, pyridine or triethylamine.
Die Reaklionstemperaturen für die verfahrensgemäße Umsetzung können in einem größeren Bereich variiert werden; im allgemeinen arbeitel man bei 50 bis 1400C.The reaction temperatures for the implementation according to the process can be varied within a substantial range; In general arbeitel at 50 to 140 0 C.
Bei der Durchführung des Verfahrens setzt man auf 1 Mol Fluorcarbonyl-N-(trihalogenmethylthio)-N-trifluormethylanilin im allgemeinen 1 Mol der Hydroxybenzoesäure und 1 Mol Säurebindemittel ein. über- oder Unterschreitungen um bis zu 20% sind ohne wesentlichen Ausbeuteverlust möglich. Auch kann das Säurebindemittel in Wegfall kommen, wenn man die Hydroxybenzoesäure als Salz, vorzugsweise als Alkalisalz, zur Umsetzung bringt. Die Aufarbeitung des Reaktionsgemisches und Isolierung der Endprodukte wird in üblicher Weise vorgenommen.When carrying out the process, 1 mole of fluorocarbonyl-N- (trihalomethylthio) -N-trifluoromethylaniline is used generally 1 mole of hydroxybenzoic acid and 1 mole of acid binder one. Exceeding or falling below by up to 20% are without significant loss of yield possible. The acid binder can also be omitted if the hydroxybenzoic acid is used as a salt, preferably as an alkali salt, to implement. Working up the reaction mixture and isolation of the end products is carried out in the usual manner.
Die folgenden Beispiele erläutern die Herstellung der erfindungsgemäßen Wirkstoffe:The following examples explain the preparation of the active ingredients according to the invention:
Wirkstoff (11Active ingredient (11
Cl1FC-S-N-/ "V-C-O-/Cl 1 FC-SN- / "VCO- /
CF,CF,
HOOCHOOC
Darstellungdepiction
34 g (0,1 Mol) 4-F'uorcarbonyl-N-(d;chlorfluormethylthio)-N-trifluormethylanilin und 16 g (0,1 Mol) Nalriumsalicylat werden in 100 ml Dioxan während34 g (0.1 mol) of 4-fluorocarbonyl-N- (d; chlorofluoromethylthio) -N-trifluoromethylaniline and 16 g (0.1 mol) of sodium salicylate are in 100 ml of dioxane during
!Stunden zum Sieden erhitzt. Nach dem Erkalten setzt man Wasser zu und nimmt das abgeschiedene öl in Toluol auf. Nach dem Trocknen der Toluollösung über Natriumsulfat wird das Lösungsmittel im Vakuum auf dem Wasserbad abgedampft 5! Heated to the boil for hours. After cooling down, add water and take the separated oil in toluene. After drying the toluene solution over sodium sulfate, the solvent is im Vacuum evaporated on the water bath 5
Als Rückstand hinterbleiben 43 g (0,094 Mol) des obigen Reaktionsproduktes in Form eines zähen goldgelben üls. Der Brechungsindex beträgt no" = 1,5536.The residue left behind is 43 g (0.094 mol) of the above reaction product in the form of a viscous golden yellow üls. The refractive index is no " = 1.5536.
N—S-CFCUN-S-CFCU
(2)(2)
COOHCOOH
ηΐ = 1,5400 ηΐ = 1.5400
FC- S — N —/FC- S - N - /
-C- O-C- O
(3)(3)
COOHCOOH
nf == 1,5502 nf == 1.5502
CF3-N-S-CFCl2
OCF 3 -NS-CFCl 2
O
14)14)
COOHCOOH
1.5513
O1.5513
O
CUFC- S — N-CUFC- S - N-
c-oc-o
(51(51
COOHCOOH
Cl-Cl-
/if' = 1,5482/ if '= 1.5482
er,he,
N-S-CFCU
ONS-CFCU
O
-C-O-1 -CO- 1
(6)(6)
COOHCOOH
3535
4040
4545
5555
60 NO, 60 NO,
COOHCOOH
CF3-N-S-CFCU
hoch viskoses ölCF 3 -NS-CFCU
highly viscous oil
CF3-N-S-CFCl2
OCF 3 -NS-CFCl 2
O
CH3OCH 3 O
n? = 1,5516n? = 1.5516
CF, — N—S-CFCl-,CF, - N-S-CFCl-,
'I O'I O
-0--0-
COOHCOOH
J V J V
COOHCOOH
Fp. 137 C
CF3-N-S-CFCl2 M.p. 137 C.
CF 3 -NS-CFCl 2
1I 1 I.
COOHCOOH
n- = 1.5540n- = 1.5540
O
CF3 - N —<f VC-O- O
CF 3 - N - <f VC-O-
S-CFCl2 S-CFCl 2
Fp. 180 CM.p. 180 ° C
C F3 — N -/ _ V C-O-S-CFCU CF 3 - N - / _ V COS-CFCU
hochviskoses ölhigh viscosity oil
COOHCOOH
!I c—o-! I c-o-
;; ;v ii3) ; ; ; v ii3)
CO-- C)-CH3 CO- C) -CH 3
n\ = 1.55 IX n \ = 1.55 IX
S-CFCUS-CFCU
hocliviskoscs ölhocliviskoscs oil
Claims (1)
Priority Applications (9)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19691919180 DE1919180C3 (en) | 1969-04-16 | Substituted methylsulfenic acid amides, processes for their preparation and agents containing them | |
| CH451370A CH499503A (en) | 1969-04-16 | 1970-03-24 | Process for the preparation of substituted hydroxybenzoic acid derivatives |
| US22363A US3636076A (en) | 1969-04-16 | 1970-03-24 | N - fluorodichloromethylmercapto - n - trifluoromethyl - amino -benzoic acid phenyl esters |
| NL7005345A NL7005345A (en) | 1969-04-16 | 1970-04-14 | |
| JP45031682A JPS4817269B1 (en) | 1969-04-16 | 1970-04-15 | |
| SE7005145A SE372262B (en) | 1969-04-16 | 1970-04-15 | |
| BE749058D BE749058A (en) | 1969-04-16 | 1970-04-16 | NEW DERIVATIVES OF HYDROXYBENZOIC ACID SUBSTITUTES ON THE HYDROXY GROUP, THEIR PREPARATION PROCESS AND THEIR APPLICATION TO THE FIGHT AGAINST MICROBES |
| FR7013856A FR2064795A5 (en) | 1969-04-16 | 1970-04-16 | |
| GB08207/70A GB1246789A (en) | 1969-04-16 | 1970-04-16 | Substituted hydroxybenzoic acid derivatives containing a substituted sulphonamide group |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19691919180 DE1919180C3 (en) | 1969-04-16 | Substituted methylsulfenic acid amides, processes for their preparation and agents containing them |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| DE1919180A1 DE1919180A1 (en) | 1970-10-22 |
| DE1919180B2 DE1919180B2 (en) | 1975-11-20 |
| DE1919180C3 true DE1919180C3 (en) | 1976-07-01 |
Family
ID=
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