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DE1250674B - - Google Patents

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Publication number
DE1250674B
DE1250674B DE1963B0074585 DEB0074585A DE1250674B DE 1250674 B DE1250674 B DE 1250674B DE 1963B0074585 DE1963B0074585 DE 1963B0074585 DE B0074585 A DEB0074585 A DE B0074585A DE 1250674 B DE1250674 B DE 1250674B
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Prior art keywords
alkyl
weight
alkenyl radical
carbon atoms
pyrethrins
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DE1963B0074585
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German (de)
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Priority to DE1963B0074585 priority Critical patent/DE1250674B/de
Priority to BE656678D priority patent/BE656678A/fr
Publication of DE1250674B publication Critical patent/DE1250674B/de
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Classifications

    • 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
    • A01N53/00—Biocides, pest repellants or attractants, or plant growth regulators containing cyclopropane carboxylic acids or derivatives thereof

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  • Life Sciences & Earth Sciences (AREA)
  • Agronomy & Crop Science (AREA)
  • Pest Control & Pesticides (AREA)
  • Plant Pathology (AREA)
  • Health & Medical Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Dentistry (AREA)
  • General Health & Medical Sciences (AREA)
  • Wood Science & Technology (AREA)
  • Zoology (AREA)
  • Environmental Sciences (AREA)
  • Agricultural Chemicals And Associated Chemicals (AREA)

Description

BUNDESREPUBLIK DEUTSCHLANDFEDERAL REPUBLIC OF GERMANY

DEUTSCHESGERMAN

PATENTAMTPATENT OFFICE

AUSLEGESCHRIFTEDITORIAL

Int. α.:Int. α .:

AOIN 47/06AOIN 47/06

AOInAOIn

Deutsche Kl.: 451-«/©3-German class: 451 - «/ © 3-

Nummer: 1 250 674Number: 1 250 674

Aktenzeichen: B 74585 IV a/451File number: B 74585 IV a / 451

Anmeldetag: 7. Dezember 1963Filing date: December 7, 1963

' Auslegetag: 21. September 1967'' Open date: September 21, 1967

Die Verwendung von Xanthogensäureestern als Insektizide und Acarizide ist bekannt (deutsche Auslegeschrift 1021 626). Ihre Wirkung ist jedoch unbefriedigend. The use of xanthic acid esters as insecticides and acaricides is known (German Auslegeschrift 1021 626). However, their effect is unsatisfactory.

Ferner ist es aus der USA.-Patentschrift 3 074 844 bekannt, schwefelhaltige organische Verbindungen, die eine C = S-Gruppe enthalten, in Mischung mit Insektiziden Wirkstoffen als Insektizide zu verwenden. Xanthogensäureester werden dort jedoch nicht erwähnt. It is also from U.S. Patent 3,074,844 known, sulfur-containing organic compounds that contain a C = S group, mixed with Use insecticidal active ingredients as insecticides. However, xanthogenic acid esters are not mentioned there.

Es wurde gefunden, daß insektizide Mittel, die 1 Gewichtsteil eines Xanthogensäureester der FormelIt has been found that insecticidal agents contain 1 part by weight of a xanthic acid ester of the formula

R' —S —C —O —RR '- S - C - O --R

Insektizides MittelInsecticidal agent

Anmelder:Applicant:

Badische Anilin- & Soda-Fabrik
Aktiengesellschaft, Ludwigshafen/RheinAniline & Soda Factory in Baden
Aktiengesellschaft, Ludwigshafen / Rhein

Als Erfinder benannt:Named as inventor:

Dr. Hermann Windel, Frankenthal;Dr. Hermann Windel, Frankenthal;

Dr. Heinrich Adolphi, LimburgerhofDr. Heinrich Adolphi, Limburgerhof

in der R einen Alkyl- oder Alkenylrest mit 1 bis 6 C-Atomen und R' einen Alkyl- oder Alkenylrest mit 2 bis 13 C-Atomen bedeutet, und 0,05 bis 1 Gewichtsteil Pyrethrin oder Ο,Ο-Dimethyl-dithiophosphoryl·· essigsäure-N-methylamid oder Ο,Ο-DimethyI-dithiophosphorsäure-(l,2-dicarbäthoxyäthyl)-ester oder den a-Naphthylester der N-Methylcarbaminsäure enthalten, eine gute insektizide Wirkung haben.in which R is an alkyl or alkenyl radical having 1 to 6 carbon atoms and R 'is an alkyl or alkenyl radical 2 to 13 carbon atoms, and 0.05 to 1 part by weight of pyrethrin or Ο, Ο-dimethyl-dithiophosphoryl · · acetic acid-N-methylamide or Ο, Ο-dimethyl-dithiophosphoric acid- (1,2-dicarbethoxyethyl) ester or contain the a-naphthyl ester of N-methylcarbamic acid, have a good insecticidal effect.

Die Giftwirkung der Xanthogensäureester ist gering. Die LD50 z. B. des Äthylesters der Aüylxanthogensäure liegt höher als 1000 mg/kg (Ratten, oral). Mischungen der Xanthogensäureester mit Pyrethrinen sind daher insbesondere für den Vorratsschutz, z.B. bei Getreide oder Getreideprodukten (Mehl), geeignet. Die Wirkungen der anderen bekannten Wirkstoffe werden durch den Zusatz der Xanthogensäureester erheblich gesteigert. Die Anwendung der Mischungen erfolgt in Form der üblichen Insektizide.The toxicity of the xanthic acid esters is low. The LD 50 z. B. the ethyl ester of Aüylxanthogenensäure is higher than 1000 mg / kg (rats, oral). Mixtures of the xanthic acid esters with pyrethrins are therefore particularly suitable for protecting stored products, for example in the case of cereals or cereal products (flour). The effects of the other known active ingredients are considerably increased by adding the xanthogenic acid esters. The mixtures are used in the form of the customary insecticides.

Die Herstellung der Xanthogensäureester, welche hier nicht beansprucht wird, kann nach bekannten Methoden (Houben- Weyl, Bd. 9, S.817) vorgenommen werden. Danach ist es vorteilhaft, ein Metallsalz der Xanthogensäure, bevorzugt ein Alkalisalz, mit einem entsprechenden Alkylhalogenid, bevorzugt einem Chlorid, umzusetzen.The preparation of the xanthic acid esters, which is not claimed here, can be carried out according to known methods Methods (Houben-Weyl, Vol. 9, p.817) can be made. After that it is beneficial to have one Metal salt of xanthogenic acid, preferably an alkali salt, with a corresponding alkyl halide, preferred a chloride.

Die folgende Vorschrift zeigt die Herstellung eines Xanthogensäureester. Die Teile sind Gewichtsteile.The following procedure shows the preparation of a xanthogenic acid ester. The parts are parts by weight.

ao 80 Teile Kaliumäthylxanthogenat werden in 300 Teilen Aceton suspendiert, dazu bei 20 bis 300C 46 Teile Butylchlorid zugegeben und die Suspension einige Tage gerührt, der entstandene Ester wird mit Wasser ausgefällt und destilliert. Die bei 2 mm Druckao 80 parts Kaliumäthylxanthogenat are suspended in 300 parts of acetone, 46 parts of butyl chloride was added thereto at 20 to 30 0 C and the suspension was stirred for several days, the resulting ester is precipitated with water and distilled. The one at 2 mm pressure

as bei 68°C siedende Fraktion ist der Äthylxanthogensäurebutylester. In entsprechender Weise können die übrigen Xanthogenester hergestellt werden.he fraction boiling at 68 ° C is butyl ethylxanthogen. The other xanthate esters can be prepared in a corresponding manner.

Die Wirkung der erfindungsgemäßen Mittel wird durch die folgenden Beispiele belegt.The effect of the agents according to the invention is demonstrated by the following examples.

Beispiel 1example 1

Glasplättchen von 8 χ 8 cm Kantenlänge werden mit einer 0,5 mg Pyrethrin und/oder 5 mg des Synergisten enthaltenden acetonischen Lösung benetzt. Nach dem Verdunsten des Lösungsmittels setzt man je 50 Kornkäfer (Sitophilus granaria) für 10 Minuten auf das imprägnierte Glasplättchen und setzt sie anschließend in saubere Beobachtungsgefäße. Nach 24 Stunden bestimmt man die Mortalität der Käfer.Glass plates with an edge length of 8 × 8 cm are filled with a 0.5 mg pyrethrin and / or 5 mg of the synergist containing acetone solution wetted. After the solvent has evaporated, one sets each Place 50 grain beetles (Sitophilus granaria) on the impregnated glass plate for 10 minutes and then place them in clean observation vessels. The mortality of the beetles is determined after 24 hours.

WirkstoffActive ingredient

Mengelot

% Mortalität nach 24 Stunden% Mortality after 24 hours

Pyrethrine Pyrethrins

CH8-CH8-O-CS-S-C4H9 . CH8-CH8-O-CS-S-C4H9 . CHa — CH8 - O — CS — S — C10H81 CH8- CH8 — O — CS — S — C10H21 CH8 — CH8 — O — CS — S — C18H84 CH 8 -CH 8 -O-CS-SC 4 H 9 . CH 8 -CH 8 -O-CS-SC 4 H 9 . CH a - CH 8 - O - CS - S - C 10 H 81 CH 8 - CH 8 - O - CS - S - C 10 H 21 CH 8 - CH 8 - O - CS - S - C 18 H 84

0,5 mg0.5 mg

5 mg
5 mg 4- 0,5 mg Pyrethrine5 mg
5 mg 4- 0.5 mg pyrethrins

5 mg
5 mg + 0,5 mg Pyrethrine5 mg
5 mg + 0.5 mg pyrethrins

5 mg5 mg

1111

5
935
93

0
960
96

709 «48/340709 «48/340

33 WirkstoffActive ingredient 44th ·/« Mortalität
nach 24 Stunden· / «Mortality
after 24 hours CH3- CH2- O — CS — S — C12H25
CH3 — CH2 — O — CS — S — C13H27
CH3- CH2-^ O — CS- S — C13H27
CH3 — CH2 — O — CS — S — CH8 — C(CH3) - CHa
CH, — CH2 — O — CS — S — CH2 — C(CH3) = CH2
1-C3H7-O-CS-S-C4H9
1-C3H7 — O — CS — S — C4H,
1-C3H7-O-CS-S-C10H81
J-C3H7 — 0 -,CS — S — C10H91
i-C3H7 — O — CS — S — C12H25 :
1-C8H7 — O — CS — S — C12H25
CH2 = CH — CH2 — 0 — CS — S — C8H5
CH2 = CH — CH, — O — CS — S — C2H6
CHg = CH — CH8 — 0 — CS — S — C4H,
CH8 = CH-CHg-O-CS-S-C4H,
CH8 = CH — CHg-O — CS- S — CH2-CH - CH8
CH2 = CH — CHg-O — CS — S — CH2 — CH - CHg
CHg = CH — CH2 -- 0 — CS- S — CHg — CH(CH,) = CH8.
CH2 = CH — CH2 — 0 — CS — S — CH2 — CH(CH8) = CH2.
CH8 = CH — CH(CH3) — O — CS — S — C13H87 ....
CH2 = CH — CH(CH3) — O — CS — S — C13H27 CH 3 - CH 2 - O - CS - S - C 12 H 25
CH 3 - CH 2 - O - CS - S - C 13 H 27
CH 3 - CH 2 - ^ O - CS - S - C 13 H 27
CH 3 - CH 2 - O - CS - S - CH 8 - C (CH 3 ) - CH a
CH, - CH 2 - O - CS - S - CH 2 - C (CH 3 ) = CH 2
1-C 3 H 7 -O-CS-SC 4 H 9
1-C 3 H 7 - O - CS - S - C 4 H,
1-C 3 H 7 -O-CS-SC 10 H 81
JC 3 H 7-0 , CS-S-C 10 H 91
iC 3 H 7 - O - CS - S - C 12 H 25 :
1-C 8 H 7 - O - CS - S - C 12 H 25
CH 2 = CH - CH 2 - O - CS - S - C 8 H 5
CH 2 = CH - CH, - O - CS - S - C 2 H 6
CHg = CH - CH 8 - 0 - CS - S - C 4 H,
CH 8 = CH-CHg-O-CS-SC 4 H,
CH 8 = CH - CHg - O - CS - S - CH 2 - CH - CH 8
CH 2 = CH - CHg-O - CS - S - CH 2 - CH - CHg
CHg = CH - CH 2 - O - CS - S - CHg - CH (CH,) = CH 8 .
CH 2 = CH - CH 2 - O - CS - S - CH 2 - CH (CH 8 ) = CH 2 .
CH 8 = CH - CH (CH 3 ) - O - CS - S - C 13 H 87 ....
CH 2 = CH - CH (CH 3 ) - O - CS - S - C 13 H 27 Mengelot 100
0
99
1
100
11
95
0
100
0
99
2 ..
74
4
77 :
3
98
0
71
0
100100
0
99
1
100
11
95
0
100
0
99
2 ..
74
4th
77 :
3
98
0
71
0
100 5 mg 4- 0,5 mg Pyrethrine
5 mg
5 mg + 0,5 mg Pyrethrine
5 mg
5 mg + 0,5 mg Pyrethrine
5 mg
5 mg + 0,5 mg Pyrethrine
5 mg
5 mg + 0,5 mg Pyrethrine
5 mg
5 mg -f 0,5 mg Pyrethrine
5 mg
5 mg + 0,5 mg Pyrethrine
5 mg
5 mg 4- 0,5 mg Pyrethrine
5 mg
5 mg 4- 0,5 mg Pyrethrine
5 mg
5 mg 4- 0,5 mg Pyrethrine
5 mg
5 mg 4- 0,5 mg Pyrethrine5 mg 4- 0.5 mg pyrethrins
5 mg
5 mg + 0.5 mg pyrethrins
5 mg
5 mg + 0.5 mg pyrethrins
5 mg
5 mg + 0.5 mg pyrethrins
5 mg
5 mg + 0.5 mg pyrethrins
5 mg
5 mg -f 0.5 mg pyrethrins
5 mg
5 mg + 0.5 mg pyrethrins
5 mg
5 mg 4- 0.5 mg pyrethrins
5 mg
5 mg 4- 0.5 mg pyrethrins
5 mg
5 mg 4- 0.5 mg pyrethrins
5 mg
5 mg 4- 0.5 mg pyrethrins

Es zeigt sich, daß Pyrethrine und Synergisten allein jeweils nur eine geringe insektizide Wirkung besitzen, während die Wirkung der Mischung sehr gut ist. Sie ist besser als die Summe der Einzelwirkungen.It turns out that pyrethrins and synergists alone each have only a slight insecticidal effect, while the effect of the mixture is very good. It is better than the sum of the individual effects.

B e i s ρ ie I 2B e i s ρ ie I 2

Die Dauerwirkung der erfindungsgemäßen Mittel demonstriert folgender Versuch:The following experiment demonstrates the long-term effect of the agents according to the invention:

lkg Roggen wird mit 2 g eines Stäubemittels behandelt, das 0,1% Pyrethrine und l°/o des Synergisten enthält. Nach der entsprechend langen Lagerung belegt man je 100 g Roggen mit je 100 Kornkäfern, deren Mortalität nach 8 Tagen bestimmt wird. ..··..;·1 kg of rye is treated with 2 g of a dusting agent containing 0.1% pyrethrins and 1% of the synergist contains. After the correspondingly long storage period, 100 g of rye are covered with 100 grain weevils, whose mortality is determined after 8 days. .. ·· ..; ·

Ergebnis:Result: WirkstoffActive ingredient Mortalitätmortality 0,1 % Pyrethrine
0,1 % Pyrethrine 4- CH2 - CH — CH8 — O — CS — S — C2H5
0,1 °/o Pyrethrine 4- C2H6 — O — CS — S — C12H25 0.1% pyrethrins
0.1% pyrethrins 4 - CH 2 - CH - CH 8 - O - CS - S - C 2 H 5
0.1% pyrethrins 4 - C 2 H 6 - O - CS - S - C 12 H 25 9 0I0 bei 24 Stunden Lagerung
100°/obei 7 Tagen Lagerung
98°/0 bei 28 Tagen Lagerung9 0 I 0 for 24 hours of storage
100% for 7 days of storage
98 ° / 0 for 28 days of storage

Es zeigt sich, daß Pyrethrine allein nur eine schwache insektizide Wirkung haben. Die Wirkung nimmt mit zunehmender Lagerung ab, während die erfindungsgemäßen Mischungen während langer Zeit eine hohe Wirksamkeit besitzen.It turns out that pyrethrins alone have only a weak insecticidal effect. The effect takes with it increasing storage, while the mixtures according to the invention for a long time a high Possess effectiveness.

Beispiel 3Example 3

In der im Beispiel 1 beschriebenen Weise wurden die folgenden Substanzen und Mischungen an Kornkäfern geprüft.. Die Mortalität der Käfer wurde nach 2 Stunden bestimmt.In the manner described in Example 1, the following substances and mixtures were applied to grain weevils tested .. The mortality of the beetles was determined after 2 hours.

WirkstoffActive ingredient

Mengelot % Mortalität% Mortality 0,5 mg0.5 mg 1111 2 mg2 mg 1313th 5mg5mg 77th 10 mg10 mg 33

Pyrethrine (I) Pyrethrins (I)

Pyrethrine (I) Pyrethrins (I)

CH, — CHg — O τ- CS — S — CH2 — C(CH8) = CH2 .
CH3-CH8-O-CS-S-CH2-C(CH3) = CH2.CH, - CHg - O τ - CS - S - CH 2 - C (CH 8 ) = CH 2 .
CH 3 -CH 8 -O-CS-S-CH 2 -C (CH 3 ) = CH 2 .

WirkstoffActive ingredient

CH3 — CHj — O — CS — S — CH4 — C(CH4) = CH2 CH 3 - CHj - O - CS - S - CH 4 - C (CH 4 ) = CH 2 CH3-CH4-Ο —CS-S-CH2-C(CH3) = CH2 CH 3 -CH 4 -Ο -CS-S-CH 2 -C (CH 3 ) = CH 2

- CHa — O — CS — S — CH8 — C(CH3) = CH2 - CH a - O - CS - S - CH 8 - C (CH 3 ) = CH 2

= CH-CH2-O-CS-S-CH2-C(CHs) = CH11 ..= CH-CH 2 -O-CS-S-CH 2 -C (CHs) = CH 11 ..

= CH-CH2-O-CS-S-CH2-C(CHa) == CH-CH 2 -O-CS-S-CH 2 -C (CHa) =

= CH-CH2-O-CS-S-CHg-C(CHa) == CH-CH 2 -O-CS-S-CHg-C (CHa) =

= CH-CH2-O-CS-S-CH8-C(CHj) = CH8 ...= CH-CH 2 -O-CS-S-CH 8 -C (CHj) = CH 8 ...

CH2 = CH — CH2 — O — CS — S — CH2 — C(CH3) = CH8 CH 2 = CH - CH 2 - O - CS - S - CH 2 - C (CH 3 ) = CH 8

C2H6-O-CS-S-C4H, C 2 H 6 -O-CS-SC 4 H,

C2H5-O-CS — S — C4H9 C 2 H 5 -O-CS-S-C 4 H 9

C2H5-O-CS-S-C4H, ·.C 2 H 5 -O-CS-SC 4 H, ·.

C2H5 — O — CS — S — C4H, C 2 H 5 - O - CS - S - C 4 H, C,H5 — O — CS — S — C4H9 C, H 5 - O - CS - S - C 4 H 9

C8H,- Ο — CS- S-C4H, C 8 H, - Ο - CS- SC 4 H,

C8H7-O-CS-S-C4H, C 8 H 7 -O-CS-SC 4 H,

C8H7-O-CS-S-C4H, C 8 H 7 -O-CS-SC 4 H,

C3H7-O-CS-S-C4H, C 3 H 7 -O-CS-SC 4 H,

C8H7-O-CS-S-C4H, C 8 H 7 -O-CS-SC 4 H,

UC3H 7 — O — CS — S — CH2 — C(CH8) = CH2 UC 3 H 7 - O - CS - S - CH 2 - C (CH 8 ) = CH 2

i-C8H7 — O — CS — S — CH2 — C(CH3) = CH2 iC 8 H 7 - O - CS - S - CH 2 - C (CH 3 ) = CH 2

i-C3H7 — O — CS — S — CH8 — C(CH8) = CH2 iC 3 H 7 - O - CS - S - CH 8 - C (CH 8 ) = CH 2

i-C8H7 — O — CS — S — CH2 — C(CH8) = CH2 iC 8 H 7 - O - CS - S - CH 2 - C (CH 8 ) = CH 2

i-CsH7 —Ο —CS-S-CH2-C(CHs) = CH2 iC s H 7 -Ο -CS-S-CH 2 -C (CHs) = CH 2

CH2 = CH — CH(CH8) — O — CS — S — C4H9 CH 2 = CH - CH (CH 8 ) - O - CS - S - C 4 H 9 CH2 = CH-CH(CHa)-O-CS-S-C4H9 CH 2 = CH-CH (CHa) -O-CS-SC 4 H 9 CH2 = CH — CH(CH3) — O — CS — S — C4H, CH 2 = CH - CH (CH 3 ) - O - CS - S - C 4 H, CH2 = CH-CH(CHs)-O-CS-S-C4H, CH 2 = CH-CH (CHs) -O-CS-SC 4 H, CH2 = CH — CH(CH8) — O — CS — S — C4H, CH 2 = CH - CH (CH 8 ) - O - CS - S - C 4 H, CH3-O — CS — S — C13H27 CH 3 -O - CS - S - C 13 H 27 CH8 — O — CS — S — C18H27 CH 8 - O - CS - S - C 18 H 27 CH3 — O — CS — S — C18H27 CH 3 - O - CS - S - C 18 H 27

CH8-O-CS-S-C18H87 CH 8 -O-CS-SC 18 H 87

CH3 — O — CS — S — C18H27 CH 3 - O - CS - S - C 18 H 27 CH3- (CHi)4- CHg- Ο — CS- S — C4H0 CH 3 - (CHi) 4 - CHg- Ο - CS- S - C 4 H 0 CH3 — (CHg)4 — CH2 — O — CS — S — C4H9 CH 3 - (CHg) 4 - CH 2 - O - CS - S - C 4 H 9 CH8-(CHj)4-CH8-O-CS-S-C4H, CH 8 - (CHj) 4 -CH 8 -O-CS-SC 4 H, CH3 — (CHj)4 — CHj — O — CS — S — C4H, CH 3 - (CHj) 4 - CHj - O - CS - S - C 4 H, CH8-(CHa)4-CH8-O — CS — S-C4H, CH 8 - (CHa) 4 -CH 8 -O - CS - SC 4 H, CH3 — (CHg)4 — CH2 — O — CS — S — CH8 — C(CH3) = CH9 CH 3 - (CHg) 4 - CH 2 - O - CS - S - CH 8 - C (CH 3 ) = CH 9 CH2 — (CHe)4 — CH2 ^ O — CS — S — CH2 — C(CH3) = CH2 CH 2 - (CHe) 4 - CH 2 ^ O - CS - S - CH 2 - C (CH 3 ) = CH 2 CH, — (CHg)4 - CH2 — O — CS — S — CH2 — C(CH8) = CH8 CH, - (CHg) 4 - CH 2 - O - CS - S - CH 2 - C (CH 8 ) = CH 8

Mengelot ·/, Mortalität· /, Mortality 2 mg 4- 2 rag I2 mg 4- 2 rag I. 8888 10 mg 4- 2 mg I10 mg 4- 2 mg I. 100100 10 mg 4- 0,5 mg I10 mg 4- 0.5 mg I. 9595 5 mg5 mg 33 10 mg10 mg 66th 2 mg 4- 2 mg I2 mg 4- 2 mg I. 9797 10 mg 4- 2 mg 110 mg 4- 2 mg 1 100100 10 mg 4- 0,5 mg I10 mg 4- 0.5 mg I. 100100 5 mg5 mg 77th 10 mg10 mg 7 ! 7 ! 2 mg 4- 2 mg I2 mg 4- 2 mg I. 9090 10 mg 4- 2 mg I10 mg 4- 2 mg I. 100100 10 mg 4- 0,5 mg I10 mg 4- 0.5 mg I. 9999 5 mg5 mg 11 10 mg10 mg 44th 2 mg 4- 2 mg I2 mg 4- 2 mg I. 8787 10 mg 4- 2 mg I10 mg 4- 2 mg I. 9898 10 mg 4- 0,5 mg I10 mg 4- 0.5 mg I. 100100 5 mg5 mg 22 10 mg10 mg 88th 2 mg 4- 2 mg I2 mg 4- 2 mg I. 7171 10 mg 4- 2 mg I10 mg 4- 2 mg I. 9090 10 mg 4- 0,5 mg I10 mg 4- 0.5 mg I. 9999 5 mg5 mg 44th 10 mg10 mg 77th 2 mg 4- 2 mg 12 mg 4- 2 mg 1 9999 10 mg 4- 2 mg I10 mg 4- 2 mg I. 100100 10 mg 4- 0,5 mg I10 mg 4- 0.5 mg I. 99.99 5 mg5 mg 11 10 mg10 mg 22 2 mg 4- 2 mg I2 mg 4- 2 mg I. 8686 10 mg 4- 2 mg I10 mg 4- 2 mg I. 9292 10 mg 4- 0,5 mg I10 mg 4- 0.5 mg I. 9999 5mg5mg 77th 10 mg10 mg 3131 2 mg 4- 2 mg I2 mg 4- 2 mg I. 100100 10 mg 4- 2 mg I10 mg 4- 2 mg I. 100100 10 mg 4- 0,5 mg I10 mg 4- 0.5 mg I. 100100 5 mg5 mg 11 10 mg10 mg 44th 10 mg 4- 0,5 mg I10 mg 4- 0.5 mg I. 8686

Beispiel4Example4

Offene Petrischalen von 10 cm Durchmesser werden mit je 1 ml der azetonischen Lösung der Wirkstoffe benetzt. Nach Verdunsten des Lösungsmittels setzt man je 50 Kornkäfer in die Schalen und beurteilt nach 2 Stunden die Mortalität.Open Petri dishes with a diameter of 10 cm are each filled with 1 ml of the acetone solution of the active ingredients wetted. After the solvent has evaporated, 50 grain beetles are placed in each of the bowls and reassessed 2 hours mortality.

WirkstoffActive ingredient

Mengelot

Mortalitätmortality

S OS O

CH3O ,ι |jCH 3 O, ι | j

y P — S — CH2 — C — NH — CH8 (II) y P - S - CH 2 - C - NH - CH 8 (II)

R OR O

CH8OxH ItCH 8 O x H It

>.— S-CH2- C-NH-CH9 (Π) > .— S-CH 2 - C-NH-CH 9 (Π)

CH3O X CH 3 O X

CH2 = CH-CH2-Ο —CS-S —CH2-C(CH9) = CH2 CH4 = CH — CH2 — O — CS — S — CH2 — C(CH9) = CH2 CH 2 = CH-CH 2 -Ο - CS-S -CH 2 -C (CH 9 ) = CH 2 CH 4 = CH - CH 2 - O - CS - S - CH 2 - C (CH 9 ) = CH 2

CH2 = CH — CH(CH,) — O — CS — S — C4H9 CH 2 = CH - CH (CH,) - O - CS - S - C 4 H 9

CH2 = CH — CH(CH3) — O — CS — S — C4H. CH 2 = CH - CH (CH 3 ) - O - CS - S - C 4 H.

CH2 = CH- CH(CH3)-O — CS- S — C1H, CH 2 = CH- CH (CH 3 ) -O - CS- S - C 1 H,

1-C9H7 — 0 — CS — S — Ci9H27 1-C 9 H 7-0 -CS-S-Ci 9 H 27

i-C3H7 — O — CS — S — C13H27 iC 3 H 7 - O - CS - S - C 13 H 27

1-C3H7- O — CS — S — C13H27 1-C 3 H 7 - O - CS - S - C 13 H 27

i-C3H7 — 0 — CS — S — C13H27 iC 3 H 7-0 -CS-S-C 13 H 27

CH3 — O — CS — S — C19H2, CH 3 - O - CS - S - C 19 H 2 ,

CH3 — O — CS — S — C13H27 CH 3 - O - CS - S - C 13 H 27

CH3 — O — CS — S — C13H27 CH 3 - O - CS - S - C 13 H 27

C6H13-O — CS — S — C1H9 C 6 H 13 -O - CS - S - C 1 H 9

CeHls — O — CS — S — C1H9 C e H ls - O - CS - S - C 1 H 9

C6H13 — O — CS — S — C4H9 C 6 H 13 - O - CS - S - C 4 H 9

S
CH3O j|S.
CH 3 O j |

^P-S-CH-COO-C2Hs (III) ^ PS-CH-COO-C 2 Hs (III)

CH3O^ I 'CH 3 O ^ I '

CH8-COO-C2H6 CH 8 -COO-C 2 H 6

i-C3H7 — O — CS — S — CH1 — CH =. CH2 iC 3 H 7 - O - CS - S - CH 1 - CH =. CH 2

J-C3H7 — O — CS — S — CH2 — CH = CH8 JC 3 H 7 - O - CS - S - CH 2 - CH = CH 8

C4H6 — O — CS — S — CH2 — C(CH3) = CH2 C 4 H 6 - O - CS - S - CH 2 - C (CH 3 ) = CH 2

C2H5 — O — CS — S — CH2 — C(CH3) = CH2 C 2 H 5 - O - CS - S - CH 2 - C (CH 3 ) = CH 2

CH8 = CH-CH2-O-Cs-S-CH2-CH = CH2.... CH2 = CH-CH2-0-CS-S-CH2-CH = CH2.... CH2 = CH — CH2-O-CS — S — CH2 — C(CH3) = CH2 CH2 = CH-CH2-O-CS-S-CH2-C(CHs) = CH2 CH 8 = CH-CH 2 -O-Cs-S-CH 2 -CH = CH 2 .... CH 2 = CH-CH 2 -0-CS-S-CH 2 -CH = CH 2 .... CH 2 = CH - CH 2 -O-CS - S - CH 2 - C (CH 3 ) = CH 2 CH 2 = CH-CH 2 -O-CS-S-CH 2 -C (CHs) = CH 2

C2H6-O-CS-S-C4H9 C 2 H 6 -O-CS-SC 4 H 9

C2H5 — O — CS- S — C4H9 C 2 H 5 - O - CS - S - C 4 H 9

i-C,H7 — O — CS — S — C4H, iC, H 7 - O - CS - S - C 4 H,

i-C8H7 — O — CS — S — C4H9 iC 8 H 7 - O - CS - S - C 4 H 9

1-C8H7-0-CS-S-CH2-C(CH3) = CH2 1-C 8 H 7 -0-CS-S-CH 2 -C (CH 3 ) = CH 2

i-C3H7 — O — CS — S — CH8 — C(CH3) = CH2 iC 3 H 7 - O - CS - S - CH 8 - C (CH 3 ) = CH 2

CH2 = CH — CH(CH8) — O — CS — S — C4H9 CH 2 = CH - CH (CH 8 ) - O - CS - S - C 4 H 9

CH2 = CH — CH(CH8) — O — CS — S — C4H9 CH 2 = CH - CH (CH 8 ) - O - CS - S - C 4 H 9

0,2 mg0.2 mg

0,4 mg0.4 mg

4 mg4 mg 1515th 4 mg4 mg + 0,4 mg II+ 0.4 mg II 8989 2 mg2 mg 88th 2 mg2 mg + 0,2 mg II+ 0.2 mg II 8181 2 mg2 mg + 0,4 mg II+ 0.4 mg II 8585 2 mg2 mg 22 4 mg4 mg 1616 2 mg2 mg + 0,4 mg II+ 0.4 mg II 5555 4 mg4 mg + 0,4 mg II+ 0.4 mg II 9393 2 mg2 mg 22 4 mg4 mg 2424 4 mg4 mg + 0,4 mg II+ 0.4 mg II 9999 2 mg2 mg 44th 2 mg2 mg + 0,2 mg II+ 0.2 mg II 6161 2 mg2 mg + 0,4 mg II+ 0.4 mg II 8080

0,2 mg0.2 mg

2424

2 mg2 mg 44th 2 mg + 0,2 mg III2 mg + 0.2 mg III 8383 2 mg2 mg 66th 2 mg + 0,2 mg ΠΙ2 mg + 0.2 mg ΠΙ 8787 2 mg2 mg 44th 2 mg + 0,2 mg ΠΙ2 mg + 0.2 mg ΠΙ 7272 2 mg2 mg 44th 2 mg + 0,2 mg III2 mg + 0.2 mg III 9999 2 mg2 mg 22 2 mg + 0,2 mg III2 mg + 0.2 mg III 7777 2 mg2 mg 00 2 mg + 0,2 mg III2 mg + 0.2 mg III 9696 2 mg2 mg 00 2 mg + 0,2 mg III2 mg + 0.2 mg III 8888 2 mg2 mg 88th 2 mg + 0,2 mg III2 mg + 0.2 mg III 100100

99 WirkstoffActive ingredient 1010 7„ Mortalität7 "Mortality CH2 - CH — CH(CH3) — O — CS — S — Cj3Hg7
CH2 - CH — CH(CH3) — O — CS — S — C13H27
J-C3H. - O — CS — S - C13H27
i-C3H7 — O — CS — S — C13H27
CH3- O — CS — S — C13H87
CH3 — O — CS — S — C18H27
C6H13 — O — CS — S — C4H,
C4H13 — O — CS — S — C4H,
C4H13 — O — CS — S — CH2- C(CH3) - CHa
C8Hi3 — O — CS — S — CH2-C(CH3) - CH2 CH 2 - CH - CH (CH 3 ) - O - CS - S - Cj 3 Hg 7
CH 2 - CH - CH (CH 3 ) - O - CS - S - C 13 H 27
JC 3 H. - O - CS - S - C 13 H 27
iC 3 H 7 - O - CS - S - C 13 H 27
CH 3 - O - CS - S - C 13 H 87
CH 3 - O - CS - S - C 18 H 27
C 6 H 13 - O - CS - S - C 4 H,
C 4 H 13 - O - CS - S - C 4 H,
C 4 H 13 - O - CS - S - CH 2 - C (CH 3 ) - CH a
C 8 Hi 3 - O - CS - S - CH 2 -C (CH 3 ) - CH 2 Mengelot 0
100
2
100
2
100
4
100
6
1000
100
2
100
2
100
4th
100
6th
100 2 mg
2 mg + 0,2 mg IH
2 mg
2 mg + 0,2 mg III
2 mg
2 mg+ 0,2 mg 111
2 mg
2 mg + 0,2 mg IU
2 mg
2 mg -I 0,2 mg UI2 mg
2 mg + 0.2 mg IH
2 mg
2 mg + 0.2 mg III
2 mg
2 mg + 0.2 mg 111
2 mg
2 mg + 0.2 mg IU
2 mg
2 mg -I 0.2 mg UI

Beispiel 5 Versuchsordnung wie bei Beispiel 3, doch wird die Mortalität nach 4 Stunden ermittelt.Example 5 Test order as in Example 3, but the mortality is determined after 4 hours.

WirkstoffActive ingredient Mengelot

7„ Mortalität7 "Mortality

W O — C — NHCH3 (IV)WO - C - NHCH 3 (IV)

CH2--=
CH2 =CH 2 - =
CH 2 =

i-CsH7
J-C3H7
CH3-CH3-C8H11 -iC s H 7
JC 3 H 7
CH 3 -CH 3 -C 8 H 11 -

CH — CH2 — O — CS — S — CH2 — C(CH3) = CH2 CH — CH2 — O — CS — S — CH2 — C(CH3) = CH2 CH - CH 2 - O - CS - S - CH 2 - C (CH 3 ) = CH 2 CH - CH 2 - O - CS - S - CH 2 - C (CH 3 ) = CH 2

CH — CH(CH3) — O — CS — S — C13H8, CH - CH (CH 3 ) - O - CS - S - C 13 H 8 ,

CH — CH(CH3) — O — CS — S — C13H27 CH - CH (CH 3 ) - O - CS - S - C 13 H 27

_O —CS-S-C13H27 _O-CS-SC 13 H 27

— O — CS — S — C13H27 - O - CS - S - C 13 H 27

O — CS — S — C13H87 O - CS - S - C 13 H 87

O — CS — S — C13H87 O - CS - S - C 13 H 87

O — CS — S — C4H9 O - CS - S - C 4 H 9

C6Hn — O — CS — S — C4H9 C 6 H n - O - CS - S - C 4 H 9

CfljHjj — O ■— C-S — S — C4J119 CfljHjj - O ■ - C-S - S - C4J119

C8H11 — O — CS — S — CH2 — C(CH3) = CH8 C8H11 — O — CS — S — CH2 — C(CH3) - CH2 C 8 H 11 - O - CS - S - CH 2 - C (CH 3 ) = CH 8 C 8 H 11 - O - CS - S - CH 2 - C (CH 3 ) - CH 2

Claims (4)

Patentansprüche:Patent claims: 1. Insektizides Mittel, enthaltend 1 Gewichtsteil an einem Xanthogensäureester der Formel1. Insecticidal agent containing 1 part by weight of a xanthogenic acid ester of the formula R' —S —C —O —RR '- S - C - O --R mgmg mg
mg -|- 2 mg IVmg
mg - | - 2 mg IV mg
mg + 1 mg IVmg
mg + 1 mg IV mg
mg + 1 mg IVmg
mg + 1 mg IV mg
mg + 1 mg IVmg
mg + 1 mg IV mgmg mg + 1 mg IV
mg + 2 mg IVmg + 1 mg IV
mg + 2 mg IV mg
mg + 2 mg IVmg
mg + 2 mg IV 1010 2 792 79 2 982 98 0 910 91 9999 1010 100100 100100 4 994 99 in der R einen Alkyl- oder Alkenylrest mit 1 bis 6 C-Atomen und R' einen Alkyl- oder Alkenylrest mit 2 bis 13 C-Atomen bedeutet, dadurch gekennzeichnet, daß es ferner 0,05 bis 6o 1 Gewichtsteil Pyrethrin enthält.in which R is an alkyl or alkenyl radical having 1 to 6 carbon atoms and R 'is an alkyl or alkenyl radical with 2 to 13 carbon atoms means thereby characterized in that it also contains 0.05 to 60 1 part by weight of pyrethrin. 2. Insektizides Mittel, enthaltend 1 Gewichtsteil an einem Xanthogensäureester der Formel 6 C-Atomen und R' einen Alkyl- oder Alkenylrest mit 2 bis 13 C-Atomen bedeutet, dadurch gekennzeichnet, daß es ferner 0,05 bis 1 Gewichtsteil Ο,Ο-Dimethyl-dithiophosphoryI-essigsäure-N-rnethylamid enthält.2. Insecticidal agent containing 1 part by weight of a xanthogenic acid ester of the formula 6 carbon atoms and R 'denotes an alkyl or alkenyl radical with 2 to 13 carbon atoms, characterized in that that there is also 0.05 to 1 part by weight of Ο, Ο-dimethyl-dithiophosphoryI-acetic acid-N-methylamide contains. 3. Insektizides Mittel, enthaltend 1 Gewichtsteil3. Insecticidal agent containing 1 part by weight an einem Xanthogensäureester der Formelon a xanthogenic acid ester of the formula R' —S —C —O —RR '- S - C - O --R R' __ S — C - O — RR '__ S - C - O - R in der R einen Alkyl- oder Alkenylrest mit I bis in der R einen Alkyl- oder Alkenylrest mit 1 bis C-Atomen und R' einen Alkyl- oder Alkenylrest mit 2 bis 13 C-Atomen bedeutet, dadurch gekennzeichnet, daß es ferner 0,05 bis 1 Gewichtsteil O.O-Dimethyl-dithiophosphorsäure-il^-dicarbäthoxyäthyl)-ester enthält.in which R is an alkyl or alkenyl radical with I to in which R is an alkyl or alkenyl radical with 1 to C atoms and R 'denotes an alkyl or alkenyl radical with 2 to 13 C atoms, characterized in that that there is also 0.05 to 1 part by weight of O.O-dimethyl-dithiophosphoric acid il ^ -dicarbethoxyethyl) ester contains. 709 648/3«709 648/3 « 4. Insektizides Mittel, enthaltend 1 Gewichtsteil mit 2 bis 13 C-Atomen bedeutet, dadurch gekenn-4. Insecticidal agent, containing 1 part by weight with 2 to 13 carbon atoms means, thereby marked an einem Xanthogensäureester der Formel zeichnet, daß es ferner 0,05 bis 1 Gewichtsteilon a xanthic acid ester of the formula that it is also 0.05 to 1 part by weight Λ-Naphthy tester der N-Methylcarbaminsäure ent-R'~S —C —O —R hält.Λ-Naphthy ester of N-methylcarbamic acid ent-R '~ S —C —O —R holds. In Betracht gezogene Druckschriften:Considered publications: in der R einen Alkyl- oder Alkenylrest mit 1 bis Deutsche Auslegeschrift Nr. 1 021 626;in which R is an alkyl or alkenyl radical with 1 to German Auslegeschrift No. 1 021 626; 6 C-Atomen und R' einen Alkyl- oder Alkenylrest OSA.-Patentschrift Nr. 3 074 844.6 carbon atoms and R 'is an alkyl or alkenyl radical, OSA. Patent No. 3,074,844. 709 648/340 9. 67 <Q Bundesdruckerei Berlin709 648/340 9. 67 <Q Bundesdruckerei Berlin
DE1963B0074585 1963-12-07 1963-12-07 Pending DE1250674B (en)

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DE1963B0074585 DE1250674B (en) 1963-12-07 1963-12-07
BE656678D BE656678A (en) 1963-12-07 1964-12-04

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Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN111298984A (en) * 2020-03-27 2020-06-19 云南铁峰矿业化工新技术有限公司 a collector

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN111298984A (en) * 2020-03-27 2020-06-19 云南铁峰矿业化工新技术有限公司 a collector

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