CH635226A5 - Fungicide - Google Patents
Fungicide Download PDFInfo
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- CH635226A5 CH635226A5 CH370878A CH370878A CH635226A5 CH 635226 A5 CH635226 A5 CH 635226A5 CH 370878 A CH370878 A CH 370878A CH 370878 A CH370878 A CH 370878A CH 635226 A5 CH635226 A5 CH 635226A5
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- fungicide
- formula
- compounds
- mankozeb
- carbon atoms
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- 239000000417 fungicide Substances 0.000 title description 16
- 230000000855 fungicidal effect Effects 0.000 title description 13
- 239000003795 chemical substances by application Substances 0.000 description 10
- 150000001875 compounds Chemical class 0.000 description 10
- 125000004432 carbon atom Chemical group C* 0.000 description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 6
- 241000223600 Alternaria Species 0.000 description 4
- 241000228245 Aspergillus niger Species 0.000 description 4
- 241000233866 Fungi Species 0.000 description 4
- 125000000217 alkyl group Chemical group 0.000 description 4
- FPIPGXGPPPQFEQ-OVSJKPMPSA-N all-trans-retinol Chemical compound OC\C=C(/C)\C=C\C=C(/C)\C=C\C1=C(C)CCCC1(C)C FPIPGXGPPPQFEQ-OVSJKPMPSA-N 0.000 description 4
- 125000004430 oxygen atom Chemical group O* 0.000 description 4
- 230000009885 systemic effect Effects 0.000 description 4
- 241000196324 Embryophyta Species 0.000 description 3
- 241000233614 Phytophthora Species 0.000 description 3
- 239000001257 hydrogen Substances 0.000 description 3
- 229910052739 hydrogen Inorganic materials 0.000 description 3
- -1 methyl sulfate cation Chemical group 0.000 description 3
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical group [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 2
- 235000010627 Phaseolus vulgaris Nutrition 0.000 description 2
- 244000046052 Phaseolus vulgaris Species 0.000 description 2
- 239000013543 active substance Substances 0.000 description 2
- 239000011717 all-trans-retinol Substances 0.000 description 2
- 235000019169 all-trans-retinol Nutrition 0.000 description 2
- 239000006172 buffering agent Substances 0.000 description 2
- 150000001805 chlorine compounds Chemical group 0.000 description 2
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- WDQNIWFZKXZFAY-UHFFFAOYSA-M fentin acetate Chemical compound CC([O-])=O.C1=CC=CC=C1[Sn+](C=1C=CC=CC=1)C1=CC=CC=C1 WDQNIWFZKXZFAY-UHFFFAOYSA-M 0.000 description 2
- XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical group I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 description 2
- 208000015181 infectious disease Diseases 0.000 description 2
- 230000005764 inhibitory process Effects 0.000 description 2
- GTCAXTIRRLKXRU-UHFFFAOYSA-N methyl carbamate Chemical compound COC(N)=O GTCAXTIRRLKXRU-UHFFFAOYSA-N 0.000 description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 description 2
- 230000017066 negative regulation of growth Effects 0.000 description 2
- 229910052757 nitrogen Inorganic materials 0.000 description 2
- 125000004433 nitrogen atom Chemical group N* 0.000 description 2
- 150000003254 radicals Chemical class 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- UYWWLYCGNNCLKE-UHFFFAOYSA-N 2-pyridin-4-yl-1h-benzimidazole Chemical compound N=1C2=CC=CC=C2NC=1C1=CC=NC=C1 UYWWLYCGNNCLKE-UHFFFAOYSA-N 0.000 description 1
- 241000266326 Alternaria botrytis Species 0.000 description 1
- 241000123650 Botrytis cinerea Species 0.000 description 1
- TWFZGCMQGLPBSX-UHFFFAOYSA-N Carbendazim Natural products C1=CC=C2NC(NC(=O)OC)=NC2=C1 TWFZGCMQGLPBSX-UHFFFAOYSA-N 0.000 description 1
- 239000005749 Copper compound Substances 0.000 description 1
- 239000005752 Copper oxychloride Substances 0.000 description 1
- 206010061217 Infestation Diseases 0.000 description 1
- 239000005909 Kieselgur Substances 0.000 description 1
- 241001465754 Metazoa Species 0.000 description 1
- OKIZCWYLBDKLSU-UHFFFAOYSA-M N,N,N-Trimethylmethanaminium chloride Chemical compound [Cl-].C[N+](C)(C)C OKIZCWYLBDKLSU-UHFFFAOYSA-M 0.000 description 1
- 241000233622 Phytophthora infestans Species 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- 240000003768 Solanum lycopersicum Species 0.000 description 1
- PTFCDOFLOPIGGS-UHFFFAOYSA-N Zinc dication Chemical compound [Zn+2] PTFCDOFLOPIGGS-UHFFFAOYSA-N 0.000 description 1
- 239000004480 active ingredient Substances 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 125000002877 alkyl aryl group Chemical group 0.000 description 1
- 239000012736 aqueous medium Substances 0.000 description 1
- GBAOBIBJACZTNA-UHFFFAOYSA-L calcium sulfite Chemical compound [Ca+2].[O-]S([O-])=O GBAOBIBJACZTNA-UHFFFAOYSA-L 0.000 description 1
- 235000010261 calcium sulphite Nutrition 0.000 description 1
- 150000004657 carbamic acid derivatives Chemical class 0.000 description 1
- JNPZQRQPIHJYNM-UHFFFAOYSA-N carbendazim Chemical compound C1=C[CH]C2=NC(NC(=O)OC)=NC2=C1 JNPZQRQPIHJYNM-UHFFFAOYSA-N 0.000 description 1
- 239000006013 carbendazim Substances 0.000 description 1
- 239000000969 carrier Substances 0.000 description 1
- HKMOPYJWSFRURD-UHFFFAOYSA-N chloro hypochlorite;copper Chemical compound [Cu].ClOCl HKMOPYJWSFRURD-UHFFFAOYSA-N 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 150000001880 copper compounds Chemical class 0.000 description 1
- 239000002270 dispersing agent Substances 0.000 description 1
- 239000012153 distilled water Substances 0.000 description 1
- HWYQLDHDBPXEQU-UHFFFAOYSA-M dodecoxymethyl(trimethyl)azanium;chloride Chemical compound [Cl-].CCCCCCCCCCCCOC[N+](C)(C)C HWYQLDHDBPXEQU-UHFFFAOYSA-M 0.000 description 1
- 230000002538 fungal effect Effects 0.000 description 1
- 244000053095 fungal pathogen Species 0.000 description 1
- 239000001963 growth medium Substances 0.000 description 1
- 150000002431 hydrogen Chemical class 0.000 description 1
- 238000000338 in vitro Methods 0.000 description 1
- 238000011835 investigation Methods 0.000 description 1
- 231100000053 low toxicity Toxicity 0.000 description 1
- 230000010807 negative regulation of binding Effects 0.000 description 1
- 229920000151 polyglycol Polymers 0.000 description 1
- 239000010695 polyglycol Substances 0.000 description 1
- 230000003389 potentiating effect Effects 0.000 description 1
- 230000001681 protective effect Effects 0.000 description 1
- 108090000623 proteins and genes Proteins 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 241000894007 species Species 0.000 description 1
- 230000004763 spore germination Effects 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 231100000925 very toxic Toxicity 0.000 description 1
- 239000000080 wetting agent Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D295/00—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms
- C07D295/04—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms
- C07D295/08—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly bound oxygen or sulfur atoms
- C07D295/084—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly bound oxygen or sulfur atoms with the ring nitrogen atoms and the oxygen or sulfur atoms attached to the same carbon chain, which is not interrupted by carbocyclic rings
- C07D295/088—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly bound oxygen or sulfur atoms with the ring nitrogen atoms and the oxygen or sulfur atoms attached to the same carbon chain, which is not interrupted by carbocyclic rings to an acyclic saturated chain
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N33/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic nitrogen compounds
- A01N33/02—Amines; Quaternary ammonium compounds
- A01N33/12—Quaternary ammonium compounds
Landscapes
- Life Sciences & Earth Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Plant Pathology (AREA)
- Engineering & Computer Science (AREA)
- Dentistry (AREA)
- General Health & Medical Sciences (AREA)
- Wood Science & Technology (AREA)
- Zoology (AREA)
- Environmental Sciences (AREA)
- Pest Control & Pesticides (AREA)
- Agronomy & Crop Science (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
Description
635 226 635 226
2 2nd
PATENTANSPRUCH Fungizides Mittel, dadurch gekennzeichnet, dass es als mindestens eine aktive Komponente eine Verbindung der Formel r, PATENT CLAIM Fungicidal agent, characterized in that it contains, as at least one active component, a compound of the formula r,
r-0-h2c' r-0-h2c '
. © . ©
.N .N
'R; 'R;
R, R,
(xe)n (xe) n
(I) (I)
worin Rj und R2 Alkyl mit 1 bis 4 Kohlenstoffatomen sind, R3 Alkyl mit 1 bis 4 Kohlenstoffatomen oder Cyclohexyl und R4 mit 1 bis 18 Kohlenstoffatomen bedeuten oder R2 und R3 zusammen mit dem Stickstoffatom, an welches sie gebunden sind, einen Ring der Formel und R4 mit 1 bis 18 Kohlenstoffatomen bedeuten oder R2 und R3 zusammen mit dem Stickstoffatom, an welches sie gebunden sind, einen Ring der Formel u wherein Rj and R2 are alkyl with 1 to 4 carbon atoms, R3 is alkyl with 1 to 4 carbon atoms or cyclohexyl and R4 with 1 to 18 carbon atoms or R2 and R3 together with the nitrogen atom to which they are attached, a ring of the formula and R4 with 1 to 18 carbon atoms or R2 and R3 together with the nitrogen atom to which they are attached, a ring of the formula u
Q Q
(Ii) (Ii)
bilden worin U und Y Wasserstoff oder Methyl sind und Z Wasser-15 Stoff ist, oder Y und Z zusammen ein Sauerstoffatom darstellen und W ein Sauerstoffatom, die Methylengruppe oder einen Rest der Formel form wherein U and Y are hydrogen or methyl and Z is water-15, or Y and Z together represent an oxygen atom and W represents an oxygen atom, the methylene group or a radical of the formula
-IV -IV
u u
17 17th
r^z di) r ^ z di)
20 20th
25 25th
e e
:n- : n-
(iii) (iii)
^CH2-0-Ra bilden, ^ Form CH2-0-Ra,
worin U und Y Wasserstoff oder Methyl sind und Z Wasserstoffist, oder Y und Z zusammen ein Sauerstoffatom darstellen und W ein Sauerstoffatom, die Methylengruppe oder einen Rest der Formel wherein U and Y are hydrogen or methyl and Z is hydrogen, or Y and Z together represent an oxygen atom and W represents an oxygen atom, the methylene group or a radical of the formula
:n' : n '
'R, 'R,
^ch2-o-r4 ^ ch2-o-r4
(iii) (iii)
bedeutet, means
worin Rj und R4 weiter oben definiert sind, X ein Chlorid-, Bromid-, Jodid- oder Methylsulfatkation bedeutet und n 1 oder 2 ist, enthält. wherein Rj and R4 are defined above, X is a chloride, bromide, iodide or methyl sulfate cation and n is 1 or 2.
Die Erfindung betrifft ein fungizides Mittel, das als mindestens eine Wirkstoffkomponente eine Verbindung der Formel e The invention relates to a fungicidal agent which, as at least one active ingredient, is a compound of the formula e
• N. • N.
(xe)n (i) (xe) n (i)
r4-0-h2c' r4-0-h2c '
worin R! und R2 Alkyl mit 1 bis 4 Kohlenstoffatomen sind, R3 Alkyl mit 1 bis 4 Kohlenstoffatomen oder Cyclohexyl bedeutet, where R! and R2 is alkyl having 1 to 4 carbon atoms, R3 is alkyl having 1 to 4 carbon atoms or cyclohexyl,
worin Rj und R2 weiter oben definiert sind, X ein Chlorid-, 30 Bromid-, Jodid- oder Methylsulfatkation bedeutet und n 1 oder 2 ist, enthält. wherein Rj and R2 are defined above, X is a chloride, 30 bromide, iodide or methyl sulfate cation and n is 1 or 2.
Die Bekämpfung pathogener Pilze der Art Alternaria und insbesondere der Art Phytophthora mit Mitteln, die als Wirkstoff Carbaminsäurederivate, Kupferverbindungen, 35 zinnorganische Verbindungen und andere enthalten, ist bekannt. The control of pathogenic fungi of the Alternaria species and in particular of the Phytophthora species by means of agents which contain carbamic acid derivatives, copper compounds, organotin compounds and others is known.
Unter den oben genannten Stoffen wird am häufigsten «Mankozeb» (Komplexverbindung von Äthylen-cis-di-thiocarbaminsäuremangan(II)salz und Zinkionen), Kup-40 feroxychlorid und Triphenylzinnacetat verwendet. Among the substances mentioned above, «Mankozeb» (complex compound of ethylene-cis-di-thiocarbamic acid manganese (II) salt and zinc ions), Kup-40 feroxychloride and triphenyltin acetate are used most often.
Diese Mittel wirken auf Pilze der Art Phythophthora und Alternaria, aber keines davon weist eine Systemwirkung auf. These agents act on fungi of the species Phythophthora and Alternaria, but none of them have a systemic effect.
Die Anwendung von Kupferoxychlorid bedarf einer sehr hohen Dosis (etwa 8 kg/ha), Triphenylzinnacetat ist ähnlich, 45 wie alle zinnorganischen Fungizide, sehr toxisch für Warm-bliitler und «Zineb» und «Mankozeb» zeichnen sich durch eine sehr kurzzeitige Wirkung aus. Ausserdem ist keines der genannten Mittel wasserlöslich. Die Löslichkeit in Wasser übt einen grossen Einfluss auf die fungizide Wirkung aus, da so die Keimung der Pilzsporen in einem wässrigen Medium erfolgt. Darüber hinaus schützt keine dieser Verbindungen vor einer Infektion der neuen, nach der Durchführung der Schutzmassnahme gewachsenen Blätter, da die genannten bekannten Verbindungen keine Systemwirkung aufweisen. 55 Unerwarteterweise wurde festgestellt, dass die weiter oben beschriebenen Verbindungen der Formel I eine starke, auch systemhafte fungizide Wirkung, speziell in bezug auf die Pilze der Arten Alternaria und Phytophthora aufweisen. The use of copper oxychloride requires a very high dose (approx. 8 kg / ha), triphenyltin acetate is similar, 45 like all organotin fungicides, very toxic to warm -blitters and «Zineb» and «Mankozeb» are characterized by a very short-term effect. In addition, none of the agents mentioned is water soluble. The solubility in water has a great influence on the fungicidal action, since the fungal spores are germinated in an aqueous medium. In addition, none of these compounds protects against infection of the new leaves which have grown after the protective measure has been carried out, since the known compounds mentioned have no system action. 55 It was unexpectedly found that the compounds of the formula I described above have a potent, also systemic fungicidal action, especially with regard to the fungi of the Alternaria and Phytophthora species.
Das erfindungsgemässe Mittel kann ausser dem Wirk-60 Stoff bekannte Zusätze, wie anorganische oder organische Träger, Verdünner oder Lösungsmittel, oberflächenaktive Stoffe, Puffermittel sowie adhäsionsvergrössernde Stoffe enthalten. In addition to the active substance, the agent according to the invention can contain known additives, such as inorganic or organic carriers, thinners or solvents, surface-active substances, buffering agents and substances which increase adhesion.
Die Wirksamkeit des erfindungsgemässen Mittels wurde 65 in biologischen Versuchen in vitro an den Pilzen Altemaria tenuis, Botrytis cinerea, Aspergillus niger geprüft. Die Ergebnisse sind in der nachfolgenden Tabelle 1 zusammengestellt. The effectiveness of the agent according to the invention was tested in biological tests in vitro on the fungi Altemaria tenuis, Botrytis cinerea, Aspergillus niger. The results are summarized in Table 1 below.
3 3rd
635226 635226
Tabelle 1 Table 1
Wirksamkeit der Verbindungen mit der allgemeinen Formel I Effectiveness of the compounds with the general formula I
Nr. der Rj No. of the Rj
r3 r3
r4 r4
X X
n n
Konzentration zur Concentration on
Konzentration concentration
Ver Ver
Hemmung der zur Hemmung bindung Inhibition of binding for inhibition
Sporenkeimung des linearen Spore germination of the linear
(ppm) (ppm)
Alternaria Botrytis tenuis cinerea Alternaria botrytis tenuis cinerea
Wachstums des Growth of
Myzeliums Mycelium
(ppm) (ppm)
Aspergillus niger Aspergillus niger
1. 1.
-ch3 -ch3
-ch3 -ch3
-ch3 -ch3
-c2h5 -c2h5
-cl 1 -cl 1
1000 1000
1000 1000
200 200
2. 2nd
-ch3 -ch3
-ch3 -ch3
-ch3 -ch3
-c3h7 -c3h7
-cl 1 -cl 1
1000 1000
1000 1000
20 20th
3. 3rd
-ch3 -ch3
-ch3 -ch3
-ch3 -ch3
-c4h9 -c4h9
-cl 1 -cl 1
1000 1000
1000 1000
20 20th
4. 4th
-ch3 -ch3
-ch3 -ch3
-ch3 -ch3
-c6h13 -c6h13
-cl 1 -cl 1
1000 1000
1000 1000
200 200
5. 5.
-ch3 -ch3
-ch3 -ch3
-ch3 -ch3
-c7h15 -c7h15
-cl 1 -cl 1
1000 1000
1000 1000
200 200
6. 6.
-ch3 -ch3
-ch3 -ch3
-ch3 -ch3
-c8h17 -c8h17
-cl 1 -cl 1
1000 1000
1000 1000
+ 20 + 20
7. 7.
-ch3 -ch3
-ch3 -ch3
-ch3 -ch3
-c9h19 -c9h19
-cl 1 -cl 1
1000 1000
1000 1000
20 20th
8. 8th.
-ch3 -ch3
-ch3 -ch3
-ch3 -ch3
-c10h21 -c10h21
-cl 1 -cl 1
100 100
100 100
20 20th
9. 9.
-ch3 -ch3
-ch3 -ch3
-ch3 -ch3
—c12h25 —C12h25
-cl 1 -cl 1
10 10th
± 10 ± 10
20 20th
10. 10th
-ch3 -ch3
-ch3 -ch3
-c18h37 -c18h37
-cl 1 -cl 1
100 100
100 100
2000 2000
11. 11.
-ch3 -ch3
-ch2ch2och2ch2 -ch2ch2och2ch2
-ci6h33 -ci6h33
-ci 1 -ci 1
+ 10 + 10
10 10th
+2000 +2000
12. 12.
-ch3 -ch3
-ch2ch2och2ch2 -ch2ch2och2ch2
-c18h37 -c18h37
-cl 1 -cl 1
100 100
100 100
2000 2000
13. 13.
-ch3 -ch3
-ch2(ch2)3ch2 -ch2 (ch2) 3ch2
~Cl2^2S ~ Cl2 ^ 2S
-Cl 1 -Cl 1
10 10th
10 10th
2000 2000
14. 14.
-ch3 -ch3
-ch2(ch2)3ch2 -ch2 (ch2) 3ch2
-Ci8h37 -Ci8h37
-Cl 1 -Cl 1
+ 10 + 10
10 10th
2000 2000
Bekanntes Vergleichspräparat Known comparator
«Zineb» "Zineb"
100 100
100 100
200 200
«Mankozeb» "Mankozeb"
+ 10 + 10
100 100
200 200
Beispiel 1 kozeb») untersucht. Die Untersuchungen wurden an jungen Das Fungizid besteht aus: 50 Teilen Dodecyloxy- Tomatenpflanzen mit 5 bis 6 Blättern durchgeführt, indem methyltrimethylammoniumchlorid, 40 Teilen Kieselgur man die Pflanzen mit den zu untersuchenden Verbindungen (anorganischer Träger), 2 Teilen Benetzungsmittel und 8 35 besprühte und anschliessend mit einer Suspension der Spo-Teilen Dispersionsmittel (Calciumsulfitlauge). ren des Pilzes Phytophtora infestans infiszierte. Nach 6 Ta-Das auf diese Weise hergestellte Fungizid wurde bei einer gen wurde der Befall der Pflanzen, im Vergleich mit den unKonzentration des Wirkstoffes von 0,1 % und 0,01 % im Ver- besprühten Pflanzen geschätzt. Die Ergebnisse sind in der gleich mit einem anderen bekannten Fungizid («Man- nachfolgenden Tabelle 2 dargestellt. Example 1 kozeb ») examined. The investigations were carried out on young. The fungicide consists of: 50 parts of dodecyloxy tomato plants with 5 to 6 leaves by methyltrimethylammonium chloride, 40 parts of diatomaceous earth, the plants with the compounds to be examined (inorganic carrier), 2 parts of wetting agent and 8 35 sprayed and then with a suspension of the spo-parts of the dispersant (calcium sulfite liquor) of the fungus Phytophtora infestans. After 6 days-the fungicide prepared in this way, the infection of the plants was estimated in one gene, in comparison with the unconcentration of the active compound of 0.1% and 0.01% in the sprayed plants. The results are shown in Table 2, which is the same as another known fungicide.
Tabelle 2 Table 2
Wirksamkeit des Mittels von Beispiel 1 gegen Kraut- und Braunfäule (Phytophthora infestans) Efficacy of the agent of Example 1 against late blight and brown rot (Phytophthora infestans)
Fungizid Konzentration % des Befalls im Fungicide concentration% of infestation in
(%) Vergleich mit der (%) Comparison with the
Kontrolle control
Nach Beispiel 1 0,01 25,8 According to Example 1 0.01 25.8
0,1 0,0 0.1 0.0
«Mankozeb» 0,01 34,1 "Mankozeb" 0.01 34.1
0,1 9,0 0.1 9.0
Kontrolle 100,0 (ohne Präparat) Control 100.0 (without preparation)
Beispiel 2 Example 2
Das Fungizid besteht aus: 10 Teilen Dodecyloxymethyl-trimethylammoniumchlorid, 0,3 Teilen Alkylarylpolyglykol-äther und 89,7 Teile destilliertes Wasser. The fungicide consists of: 10 parts of dodecyloxymethyltrimethylammonium chloride, 0.3 part of alkylaryl polyglycol ether and 89.7 parts of distilled water.
Das auf diese Weise hergestellte Fungizid wurde zur Untersuchung der Systemwirkung im Vergleich mit einem bekannten Systemfungizid, nämlich dem «Karbendazim» (N-(2-Benzimidazol)carbaminsäuremethylester) und mit einem anderen bekannten Fungizid, dem «Mankozeb», eingesetzt. The fungicide produced in this way was used to investigate the systemic effect in comparison with a known system fungicide, namely the “carbendazim” (N- (2-benzimidazole) carbamic acid methyl ester) and another known fungicide, the “Mankozeb”.
Das nach dem Beispiel zubereitete Fungizid und die Vergleichsfungizide wurden mit Wasser bis zu einer Konzentration von 1,0%, 0,1% sowie 0,01% verdünnt. The fungicide prepared according to the example and the comparative fungicides were diluted with water to a concentration of 1.0%, 0.1% and 0.01%.
In die so zubereiteten Lösungen wurden die Wurzeln von Bohnensetzlingen 24 Stunden lang eingetaucht. Nach dieser Zeit wurden die Triebe in 1 cm lange Stücke geschnitten. In 60 Petrischalen, die mit den Sporen des Pilzes Aspergillus niger infiszierte Nährböden enthalten, wurden je 5 Schnitte der Triebe gelegt. Nach 4 Tagen wurden die Zonen der Hemmung des Myzeliumwachstums entlang der Schnitte gemessen. Die Ergebnisse sind in der nachfolgenden Tabelle 3 dar-65 gestellt. The roots of bean seedlings were immersed in the solutions prepared in this way for 24 hours. After this time the shoots were cut into 1 cm long pieces. 5 sections of the shoots were placed in 60 petri dishes containing culture media infected with the spores of the Aspergillus niger fungus. After 4 days the zones of inhibition of mycelium growth along the sections were measured. The results are shown in Table 3 below-65.
635226 635226
4 4th
Tabelle 3 Table 3
Untersuchte Substanz Konz. (%) Durchmesser der Zone der Hemmung des Wachstums des Mittlerer Durch- Investigated substance Conc. (%) Diameter of zone of inhibition of growth of the mean
Myzeliums von Aspergillus niger entlang des Schnittes messer der Zone Aspergillus niger mycelium along the section knife of the zone
1 1
2 2nd
3 3rd
4 4th
5 5
der Wachstumshemmung des Myzeliums (mm) the inhibition of growth of the mycelium (mm)
Mittel nach Means after
1,0 1.0
7 7
9 9
5 5
7 7
9 9
7,4 7.4
Beispiel 2 Example 2
0,1 0.1
6 6
0 0
5 5
5 5
0 0
3,2 3.2
0,01 0.01
0 0
0 0
0 0
0 0
0 0
0,0 0.0
«Karbendazin» "Karbendazin"
1,0 1.0
6 6
5 5
9 9
5 5
7 7
6,4 6.4
0,1 0.1
6 6
5 5
5 5
0 0
6 6
4,4 4.4
0,01 0.01
0 0
0 0
0 0
0 0
0 0
0,0 0.0
«Mankozeb» "Mankozeb"
1,0 1.0
0 0
0 0
0 0
0 0
0 0
0,0 0.0
0,1 0.1
0 0
0 0
0 0
0 0
0 0
0,0 0.0
0,01 0.01
0 0
0 0
0 0
0 0
0 0
0,0 • 0.0 •
Kontrolle mit Control with
mit Wasser with water
- -
0 0
0 0
0 0
0 0
0 0
0,0 0.0
Die erhaltenen Ergebnisse weisen darauf hin, dass das er- seiner hohen Wirksamkeit auch auf seiner Systemwirkung, findungsgemässe Mittel durch die Wurzel in die Bohnen- die bei anderen bekannten Fungiziden zur Bekämpfung von triebe eindrang, ähnlich wie das bei dem bekannten System- 25 Alternaria und Phytophthora nicht festgestellt werden konn-fungizid «Karbendazim» der Fall ist. Dadurch wurde die Sy- te. Ein weiterer Vorteil des erfindungsgemässen Mittels ist stemwirkung des erfindungsgemässen Mittels bestätigt. auch seine niedrige Toxizität für Warmblütler und seine sehr The results obtained indicate that this, due to its high effectiveness, also on its systemic effect, agents according to the invention penetrated into the beans by means of the root, which penetrated in other known fungicides for controlling shoots, similar to that in the known system 25 Alternaria and Phytophthora could not be identified - fungicide "Karbendazim" is the case. This made the system. A further advantage of the agent according to the invention is confirmed by the effect of the agent according to the invention. also its low toxicity to warm-blooded animals and its very
Ein Vorteil des erfindungsgemässen Mittels beruht neben gute Wasserlöslichkeit, die die Anwendung erleichtert. In addition to good water solubility, an advantage of the agent according to the invention is that it facilitates use.
s s
1 Blatt Zeichnungen 1 sheet of drawings
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| PL19661177A PL106181B1 (en) | 1977-03-11 | 1977-03-11 | FUNGICIDE |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH635226A5 true CH635226A5 (en) | 1983-03-31 |
Family
ID=19981386
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH370878A CH635226A5 (en) | 1977-03-11 | 1978-03-10 | Fungicide |
Country Status (18)
| Country | Link |
|---|---|
| JP (1) | JPS53139723A (en) |
| AT (1) | AT357373B (en) |
| BE (1) | BE864781A (en) |
| BG (1) | BG28550A3 (en) |
| BR (1) | BR7801516A (en) |
| CA (1) | CA1100403A (en) |
| CH (1) | CH635226A5 (en) |
| CS (1) | CS194199B2 (en) |
| DD (1) | DD134474A5 (en) |
| DE (1) | DE2810066C2 (en) |
| ES (1) | ES467744A1 (en) |
| FR (1) | FR2382858A1 (en) |
| GB (1) | GB1602871A (en) |
| HU (1) | HU180800B (en) |
| NL (1) | NL171117C (en) |
| PL (1) | PL106181B1 (en) |
| RO (1) | RO75147A (en) |
| SU (1) | SU701515A3 (en) |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE3424681A1 (en) * | 1984-07-05 | 1986-02-06 | Fa. Anton Zahoransky, 7868 Todtnau | Brush manufacturing machine |
| DD263686B1 (en) * | 1985-07-05 | 1990-08-08 | Inst Pflanzenschutzforschung | FUNGICIDAL AGENTS |
| JP2006036652A (en) * | 2004-07-22 | 2006-02-09 | Sanko Kagaku Kogyo Kk | Method for producing ionic liquid and new onium salt |
Family Cites Families (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE704388C (en) * | 1931-10-07 | 1941-03-29 | Hydrierwerke Akt Ges Deutsche | Process for the production of quaternary ammonium compounds |
| DE755155C (en) * | 1939-05-26 | 1951-11-29 | Zschimmer & Schwarz Chem Fab D | Process for the production of mosquito repellent socks |
| DE1225663B (en) * | 1962-03-02 | 1966-09-29 | Hoechst Ag | Stabilization of water-soluble, surface-active quaternary alkoxymethyl-trialkyl-ammonium halides |
| CH509970A (en) * | 1966-03-26 | 1971-07-15 | Bayer Ag | Process for the preparation of quaternary ammonium salts |
| US3626011A (en) * | 1968-07-26 | 1971-12-07 | Scm Corp | {62 -dialkylaminoalkyl ethers and thioethers |
| US3681462A (en) * | 1969-07-31 | 1972-08-01 | Scm Corp | Dialkylaminoalkyl acetylenic ethers |
| US3842179A (en) * | 1971-03-11 | 1974-10-15 | Scm Corp | Anti-microbial diaralkylaminoalkyl ethers and process for protecting plants |
| JPS49100224A (en) * | 1973-01-29 | 1974-09-21 |
-
1977
- 1977-03-11 PL PL19661177A patent/PL106181B1/en unknown
-
1978
- 1978-03-08 DE DE19782810066 patent/DE2810066C2/en not_active Expired
- 1978-03-09 AT AT170778A patent/AT357373B/en not_active IP Right Cessation
- 1978-03-10 CH CH370878A patent/CH635226A5/en not_active IP Right Cessation
- 1978-03-10 FR FR7807073A patent/FR2382858A1/en active Granted
- 1978-03-10 GB GB960778A patent/GB1602871A/en not_active Expired
- 1978-03-10 JP JP2758278A patent/JPS53139723A/en active Pending
- 1978-03-10 CA CA298,647A patent/CA1100403A/en not_active Expired
- 1978-03-10 SU SU782589398A patent/SU701515A3/en active
- 1978-03-10 CS CS152578A patent/CS194199B2/en unknown
- 1978-03-10 DD DD20411378A patent/DD134474A5/en unknown
- 1978-03-10 HU HUII000260 patent/HU180800B/en unknown
- 1978-03-10 NL NL7802629A patent/NL171117C/en not_active IP Right Cessation
- 1978-03-10 BE BE185840A patent/BE864781A/en unknown
- 1978-03-10 BG BG038986A patent/BG28550A3/en unknown
- 1978-03-10 ES ES467744A patent/ES467744A1/en not_active Expired
- 1978-03-11 RO RO7893475A patent/RO75147A/en unknown
- 1978-03-13 BR BR7801516A patent/BR7801516A/en unknown
Also Published As
| Publication number | Publication date |
|---|---|
| BE864781A (en) | 1978-07-03 |
| FR2382858B1 (en) | 1981-12-18 |
| NL171117C (en) | 1983-02-16 |
| DD134474A5 (en) | 1979-03-07 |
| BR7801516A (en) | 1978-10-10 |
| PL106181B1 (en) | 1979-11-30 |
| RO75147A (en) | 1980-11-30 |
| GB1602871A (en) | 1981-11-18 |
| FR2382858A1 (en) | 1978-10-06 |
| CA1100403A (en) | 1981-05-05 |
| AT357373B (en) | 1980-07-10 |
| BG28550A3 (en) | 1980-05-15 |
| PL196611A1 (en) | 1978-09-25 |
| CS194199B2 (en) | 1979-11-30 |
| ES467744A1 (en) | 1979-09-01 |
| ATA170778A (en) | 1979-11-15 |
| NL171117B (en) | 1982-09-16 |
| DE2810066C2 (en) | 1984-12-20 |
| SU701515A3 (en) | 1979-11-30 |
| NL7802629A (en) | 1978-09-13 |
| JPS53139723A (en) | 1978-12-06 |
| DE2810066A1 (en) | 1978-09-21 |
| HU180800B (en) | 1983-04-29 |
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| Date | Code | Title | Description |
|---|---|---|---|
| PL | Patent ceased | ||
| PL | Patent ceased |