DE2022505A1 - Acaricidal agents - Google Patents
Acaricidal agentsInfo
- Publication number
- DE2022505A1 DE2022505A1 DE19702022505 DE2022505A DE2022505A1 DE 2022505 A1 DE2022505 A1 DE 2022505A1 DE 19702022505 DE19702022505 DE 19702022505 DE 2022505 A DE2022505 A DE 2022505A DE 2022505 A1 DE2022505 A1 DE 2022505A1
- Authority
- DE
- Germany
- Prior art keywords
- hoe
- hydrogen
- acaricidal agents
- radical
- oco
- 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.)
- Pending
Links
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D235/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, condensed with other rings
- C07D235/02—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, condensed with other rings condensed with carbocyclic rings or ring systems
- C07D235/04—Benzimidazoles; Hydrogenated benzimidazoles
- C07D235/06—Benzimidazoles; Hydrogenated benzimidazoles with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached in position 2
- C07D235/10—Radicals substituted by halogen atoms or nitro radicals
-
- 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
- A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
- A01N43/48—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with two nitrogen atoms as the only ring hetero atoms
- A01N43/50—1,3-Diazoles; Hydrogenated 1,3-diazoles
- A01N43/52—1,3-Diazoles; Hydrogenated 1,3-diazoles condensed with carbocyclic rings, e.g. benzimidazoles
Landscapes
- Life Sciences & Earth Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Dentistry (AREA)
- Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Plant Pathology (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)
Description
;FABBWBREE HOECHST AG vormals Meister Lucius & Brüning Aktenzeichen: . -HOE 7O/FO75; FABBWBREE HOECHST AG formerly Master Lucius & Brüning File number: . -HOE 7O / FO75
Datum· 6. Mai 1970Date May 6, 1970
Die vorliegende Erfindung bezieht sich auf akarizide Mittel, die gekennzeichnet sind durch den Gehalt an BenzimidazQlen der allgemeinen Formel I:The present invention relates to acaricidal agents, which are characterized by the benzimidazole content of the general formula I:
(I)(I)
in der x gleichartige oder verschiedene Substituenten bezeichnen kann und Wasserstoff oder Halogen, vorzugsweise Chlor oder Brom oder eine Nitro- oder Aminogruppe bedeutet, η für eine ganze Zahl von 1 bis 4 steht und R Wasserstoff oder eignen Carbanoylrest . in which x denote identical or different substituents and denotes hydrogen or halogen, preferably chlorine or bromine or a nitro or amino group, η denotes is an integer from 1 to 4 and R is hydrogen or a suitable carbanoyl radical.
-C-NHR1 ■ .'-C-NHR 1 ■. '
bedeutet, in dem R' einen Alkylrest mit 1 bis 4 C-Atomen oder den Phenylrest darstellt.means in which R 'is an alkyl radical having 1 to 4 carbon atoms or represents the phenyl radical.
Die N-Hydroxy-benzimidazolderivate der allgemeinen Formel I, in denen R gleich"'Wasserstoff ist, können im tautomeren Gleichgewicht zur N-Oxidform stehen;The N-hydroxy-benzimidazole derivatives of the general formula I, in which R is "'hydrogen, can be in tautomeric equilibrium are in the N-oxide form;
109848/1851109848/1851
HOE 7O/FO75HOE 7O / FO75
(Ia)(Ia)
(Ib)(Ib)
Die Herstellung der durch Formel I gekennzeichneten Benzimidazolverbindungen wird wie in der belgischen Patentschrift 734 835 beschrieben durchgeführt.The preparation of the benzimidazole compounds characterized by formula I. is carried out as described in Belgian patent 734 835.
Bedingt durch ihren andersartigen Wirkungsmechanismus zeichnen sich die erfindungsgemäßen Verbindungen besonders durch ihre Wirksamkeit bei solchen Spinnmilben-Stämmen aus, die eine stark ausgebildete Resistenz gegenüber Phosphorsäureestern und akariziden chlorierten Kohlenwasserstoffen besitzen.Due to their different mechanism of action, the compounds according to the invention are particularly distinguished by their Efficacy in those spider mite strains that have a strong resistance to phosphoric acid esters and acaricides have chlorinated hydrocarbons.
Die erfindungsgemäßen Benzxmidazolderivate bewirken eine schnelle Abtötung von Spinnmilben in allen Entwicklungsstadien einschließlich ihrer Eier.The benzxmidazole derivatives according to the invention bring about a rapid killing of spider mites in all stages of development including their eggs.
Die Mittel lassen sich mit den in der "folgenden Tabelle aufgeführten Wirkstoffen mischen.The remedies can be determined with the ones listed in the "following table Mix active ingredients.
I. Insektizide I. Insecticides
a) Phosphorsäureester, z.B. Demeton, Parathion, Mevinphos;a) Phosphoric acid esters, e.g. Demeton, Parathion, Mevinphos;
b) Chlorierte Kohlenwasserstoffe, z.B. DDT, HCH (Lindan) f Aldrin, Dieldrin;b) Chlorinated hydrocarbons, for example DDT, HCH (lindane) f aldrin, dieldrin;
c) Carbamate, z.B. Carbaryl,c) carbamates, e.g. carbaryl,
sowie sonstige Wirkstoffe, z.B. Endosulfan.as well as other active ingredients, e.g. endosulfan.
10 9 8 4 8/185110 9 8 4 8/1851
HOE 7O/FO75HOE 7O / FO75
II. Fungizide II. Fungicides
- "■ ' . ■■ ■*- "■ '. ■■ ■ *
Thiocarbamate, z.B. Thiram, ferner Schwefel- undKupfersprühmittel . Thiocarbamates, e.g. thiram, as well as sulfur and copper sprays.
Die Verbindungen der allgemeinen Formel I können als solche oder in Kombination mit den oben genannten Wirkstoffen mit Lösungsmitteln, Emulgatoren, Haftmitteln oder Inertstoffen .. wie Talkum usw. -als Lösungen, Dispersionskonzentrate, emulgierbare Konzentrate oder als Stäubepulver formuliert und angewandt werden. Λ ; 'The compounds of general formula I can be used as such or in combination with the above-mentioned active ingredients Solvents, emulsifiers, adhesives or inert substances. like talc etc. -as solutions, dispersion concentrates, emulsifiable Concentrates or formulated and applied as dust powders will. Λ; '
Anhand des nachstehenden Beispiels soll die akarizide Wirkung der beanspruchten Verbindungen gezeigt werden.The acaricidal effect should be based on the following example of the claimed compounds are shown.
Besonders hervori-agend ist die akarizide Wirkung der Verbindungen 5, 12 und 13 der Tabelle des folgenden Beispiels.The acaricidal effect of the compounds is particularly outstanding 5, 12 and 13 of the table of the following example.
Bohnenpflanzen (Phaseolus vulgaris) mit Gesamtpopulationen von resistenten Spinnmilben (Tetränychus urticae) werden mit wässrigen Verdünnungen emulgierbarer oder suspendierbarer Konzentrate besprüht, bis die Sprühbrühe von den Pflanzen abzulaufen beginnt. Die Aufstellung der Pflanzen erfolgt im Gewächshaus bei 2O°C und 45 % Luftfeuchtigkeit. Die Kontrolle der Wirkung wird 8 Tage nach der Spritzung durchgeführt. Bean plants (Phaseolus vulgaris) with total populations of resistant spider mites (Tetränychus urticae) are sprayed with aqueous dilutions of emulsifiable or suspendable concentrates until the spray liquor begins to run off the plants. The plants are placed in a greenhouse at 20 ° C. and 45 % atmospheric humidity. The control of the effect is carried out 8 days after the spraying.
10 9 8 4 8/1851 . . './.10 9 8 4 8/1851. . './.
HOE 7O/FO75HOE 7O / FO75
In der folgenden Tabelle entsprechen die Werte den % Aktivsubstanz (AS) in der Spritzbrühe und den erzielten % Abtötung der Gesamtpopulation.In the table below, the values correspond to the % active substance (AS) in the spray liquor and the% kill of the total population achieved.
Wie aus der Tabelle ersichtlich, sind die erfindungsgemäßen Verbindungen in ihrer Wirkung dem Demeton (I), sowie dem Tetradifon bei diesem resistenten Spinnmilbenstamm weit überlegen.As can be seen from the table, the compounds according to the invention are in their action the demetone (I), as well as the tetradifon far superior to this resistant strain of spider mites.
109848/1851109848/1851
HOE 7O/FO75HOE 7O / FO75
Akarizide Wirkung- bei Tetranychus urticaeUrticae Akar izide effect- at Tetranychus
Formel % AS i.d. Spritzb,rühe / _%. Abtötung Formula % AS id Spritzb, rühe / _%. Mortification
ClCl
ClCl
B1 B 1
ClCl
ClCl
ClCl
OHOH
OHOH
N \N \
OhOh
CF,CF,
CF.CF.
CF,CF,
CF,CF,
OHOH
ClCl
CF,CF,
OhOh
109848/1851 - 0,05 / 109848/1851 - 0.05 /
0,1 / 900.1 / 90
0,1 / 900.1 / 90
0,025 /0.025 /
0,0125 /0.0125 /
HOE 7O/FO75HOE 7O / FO75
Nr.No.
Formelformula
% AS i.d. Spritzbrühc / % Abtötung . % AS i.d. Spritzbrühc /% destruction.
ClCl
ClCl
ClCl
ClCl
ClCl
. CF, N. CF, N
OCO-NH-CH,OCO-NH-CH,
CF,CF,
.N OCO-NHC6H5 .N OCO-NHC 6 H 5
BrBr
BrBr
Cl.Cl.
CF,CF,
OCO-ΝΗΟ,Η,-6 5OCO-ΝΗΟ, Η, -6 5
N
OCO-NHCH,N
OCO-NHCH,
109848/1851109848/1851
0,1 / 750.1 / 75
0,1 / 1000.1 / 100
0,05 / 750.05 / 75
0,1 / 900.1 / 90
0,05 / 900.05 / 90
0,1 / 1000.1 / 100
■- 7 -■ - 7 -
HOE 7O/FO75HOE 7O / FO75
Nr.No.
Formel % AS i.d. Spritzbrühe % Abtötung Formula % AS id spray liquid% kill
ClCl
1212th
ClCl
Cl
ClCl
Cl
1313th
ClCl
CF,CF,
OCO-NHCH,OCO-NHCH,
CF,CF,
ClCl
OCO-NHC4H9 OCO-NHC 4 H 9
Demeton IDemeton I
P-O(CH2)2-S-CH2-CH3 PO (CH 2 ) 2 -S-CH 2 -CH 3
ClCl
Tetradifon Tetradifon
ClCl
ClCl
SO0-T VCISO 0 -T VCI
109848/1851 0,0125 / 97 109848/1851 0.0125 / 97
0,006 /970.006 / 97
0,05 / ohne YrTirkungMPACT 0.05 / without Yr T
0,025 / ohne Wirkung0.025 / no effect
Claims (1)
-C-NHR1 O
-C-NHR 1
Priority Applications (5)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19702022505 DE2022505A1 (en) | 1970-05-08 | 1970-05-08 | Acaricidal agents |
| NL7106017A NL7106017A (en) | 1970-05-08 | 1971-05-03 | |
| BE766791A BE766791A (en) | 1970-05-08 | 1971-05-06 | ACARICIDE AGENTS |
| IL36787A IL36787A0 (en) | 1970-05-08 | 1971-05-06 | Acaricidal compositions containing benzimidazole |
| FR7116801A FR2088453A1 (en) | 1970-05-08 | 1971-05-10 | Acaricidal compsns contg substd benzimidazoles |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19702022505 DE2022505A1 (en) | 1970-05-08 | 1970-05-08 | Acaricidal agents |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE2022505A1 true DE2022505A1 (en) | 1971-11-25 |
Family
ID=5770572
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19702022505 Pending DE2022505A1 (en) | 1970-05-08 | 1970-05-08 | Acaricidal agents |
Country Status (5)
| Country | Link |
|---|---|
| BE (1) | BE766791A (en) |
| DE (1) | DE2022505A1 (en) |
| FR (1) | FR2088453A1 (en) |
| IL (1) | IL36787A0 (en) |
| NL (1) | NL7106017A (en) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CA1101179A (en) * | 1979-09-20 | 1981-05-19 | Pierre Thabet | Structural panel |
-
1970
- 1970-05-08 DE DE19702022505 patent/DE2022505A1/en active Pending
-
1971
- 1971-05-03 NL NL7106017A patent/NL7106017A/xx unknown
- 1971-05-06 BE BE766791A patent/BE766791A/en unknown
- 1971-05-06 IL IL36787A patent/IL36787A0/en unknown
- 1971-05-10 FR FR7116801A patent/FR2088453A1/en not_active Withdrawn
Also Published As
| Publication number | Publication date |
|---|---|
| FR2088453A1 (en) | 1972-01-07 |
| BE766791A (en) | 1971-11-08 |
| IL36787A0 (en) | 1971-07-28 |
| NL7106017A (en) | 1971-11-10 |
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