Insecticidic agent

专利摘要:
New phosphoric acid derivatives, a process for their manufacture by reaction of cyclopropylmethyl halides with salts of phosphoric acid derivatives, and pesticides containing these new phosphoric acid derivatives as active ingredients.
公开号:SU725543A1
申请号:SU2506702
申请日:1977-07-29
公开日:1980-03-30
发明作者:Теобальд Ханс；Адольфи Гейнрих；Айкен Карл
申请人:Басф Аг (Фирма)；
IPC主号:

专利说明:

(54) INSECTICIDAL MEANS
 I
This invention relates to chemical insect control agents, namely to an insecticidal agent based on 1X dichloro-diplopropylmetl lithiophosphoric acid.
An insecticidal agent containing 0,0-diethyl-8-11- (2, 2) -dichlorocyclopropnl) ethyl-dithiophosphate and the usual additives is known. However, its activity is insufficient.
The aim of the invention is to find a new insecticidal agent based on derivatives of dichloro-cyclopropyl methyl thiophosphoric acid, which has an enhanced insecticidal effect.
This goal is achieved by using, as a dichlorocyclopropylmethyl-phosphoric acid derivative, a compound of the general formula
Ct С &
X
7
-CHo-S-P
OR2
R3 R
is hydrogen, methyl;
-Cj-Cj - alkoxy, CI-GS - alkylthio) butynylthio, benzylthio, dimethylamino,
R Y - C1-C2-alknl;
- oxygen, sulfur, in the amount of 0.5-99 wt.%.
The compounds of formula 1 are obtained by the interaction of cyclopropylmethyl halides with phosphoric acid solids.
The reaction is usually carried out in solutions or diluents that are inert to the components of the reaction. For carrying out the method, the starting material is used in equimole pH ratios. The reaction temperature ranges from 0-150 ° C, preferably between 20-100 ° C.
Example.
C1 C1
dKiS-P (oCtH5) i.
R r
Where
 hydrogen, methyl; - hydrogen;
To a mixture of 60.5 weight.h. allyl bromide, 120 weight.h. chloroform and 1.5 wt.h. triethylbenzylammonium chloride is added dropwise with vigorous stirring 120 vol. 5 (G-aqueous sodium hydroxide solution. The reaction mixture was kept for 3 hours at 35-40 ° C. The mixture was then diluted with water and extracted with chloroform. After drying, the solvent was removed and the residue was distilled. 36.2 parts by weight were obtained. 2,2-dichlorocyclopropylmethyl bromide; yield 36%, bp 79 ° C / 25 mm Hg 20.3 parts by weight of 0,0-diethyl dithiophosphate ammonium are displaced from 20.4 ppm in 100 area of acetonitrile 2 , 2-dichloropropylmethyl bromundum and 0.5 part by weight of potassium iodide for 5 hours at 70-80 0. After cooling, the precipitated precipitate is sucked off and the filtrate is concentrated. OctiaTOK is dissolved toluene, obrabatshayut dilute sodium bicarbonate solution and water and after drying, toluene was removed with sodium sulfate. The residue was distilled at 50 ° C / 02 mmHg
H NSH3 CaHsO CjHs
SNZ NN Yzo-SzN, CjHs
NNNSNz SNS
H HH S-CHi-CzHs
СНз НН СНз-С-- CjHs
-C-CHj-S
H NN CH3 CjH;
CHE HH CaHzr CaHs
Table 1
(60, SOS1 + DDMSO)
1.25 (6J), 1.42 (ZN), 1.5 (2H), 3.18 (2H), 4.15 (4H)
| 100, SOS1) - 1.28 (ZN),
1.33 (ZN), 1.4 (ZN) 1.5 (ZN), 1.1-1.7 (2H), 3.05 (2H), 3.55 (W), 4.21 (2H )
(220, CDCIa), 1.26 (W),
2.0 (2H), 2.81 (2H), 3, 48 (6H)
(60, СОС1з), 1.3 (ЗН), 1.71 (Ш),
3.0 (2H), 3.98 (2H), 4.2 (2H), 7.24 (5H)
(60, CDCU), 1.1-1.66
(ZN + ZN + 2H), 1.78 (ZN), 2.8-3.3 (2H), 3.4-3.8 (2H), 4.0-4.5 (2H)
(60, SOS1) 1.33 (W)
1.4 (ЗН), 1.8 (1Н), 2.08 (Ш), 2.4 (ЗН), 3.12Ч2Н), 4.3 (2Н)
(60, СОС1з) 1,3 (ЗН),
1.4 (6H), 1.9 (IH), 3.1 (2H), 4.25 (4H) 27.6 parts by weight are obtained light yellow liquid; 90% yield of theoretical. CgHisCliOjPSj (309) Calculated,%: C 31.1; H 4.9; S 20.7; Clj 22, P 10.0, Found,%: C 31.2; H 4.9; S 20.7; ,four; R 10.1. 60 MHz - NMR spectrum in COC1E (5 - value): 1.36 (6H); 1.5 - 1.05 (2H); 1.952.55 (1H); 3.1 (2H); 3.9 - 4.5 (4H). Compounds obtained in a similar manner are presented in Table. 1. bNg-8-RU N CHjO. CHj N N Dosage regimens are common. The invention is illustrated as follows. A. In the experiment, cotton bedbugs (Oysderens intermedins) are raised. 250 g of sterile sandy soil 20 are thoroughly mixed with 20 ml of an aqueous emulsion of the active principle.
B. Gastrointestinal and contact effects on caterpillars of the cabbage moth (Pentella macnlipennis).
The leaves of young cabbage plants are immersed for 3 seconds. into the aqueous emulsion acting
Continued gab. 1 IS
onset of varying concentrations and after a certain time of drainage they are placed on a wetted filter in a Petri dish. Then 10 caterpillars of the 4th stage are placed on the sheet.
After 48 h, the degree of mortality is determined. The results are presented in Table. 3. (220, CDCIs), 1.22 (3N), 1.88 (1H), 1.76 (1H), 2.1 (2H). 3.46 (6H) (100, CDCI, 1.05-1.6 (1H + 1H + 3N OZ) 2.7 (6H). 2.6-3.1 (2H) 4.12 (2H) and They are filled into glasses with a capacity of 1. In these glasses, Uycderens are placed in 20 stages in the following stage, and cottonseeds swollen in water are obtained as insects by the insects until the next generation larvae hatch. The results are presented in Table 2. table 2
7725543g
Effective I Concentration of the emulsion
beginning | current beginning,%
70.0 100
30,00585
0.025-80
Century. Cultivation of a fly of the room (Myscay is mixed with a water emulsion
domestica). acting start. After cooling on PI50 nutrient medium out of 100 parts of water, the eggs fly and observe their development during
10 parts of yeast, 10 parts of dry milk weeks at 22 ° C. And one part of agar in a warm state of the axis. The results are presented in Table. .four.
Acting, Acting degree of mortality,%
beginning in the soil part
in a million
110Full suppression
Table3
j pinch medium is applied approx. Oh ml
Table4
5Strong suppression
No action
G. Contact action on the housefly (Musca domestica). Permanent contact.
In both parts of a Petri dish with a diameter of 10 cm, only 2 ml of the acetone solution is applied.
The number of active on the currant Petri, mg
0.2 0.02
ci 0,2 0,02
3 (known)
of the beginning. After evaporation of the solvent (30 minutes), 10 flies are placed in the box. Mortality set after 4 hours. The results are presented in table. five.
Table 5 The degree of mortality,%
100
80
80
No action
9725543 10
Thus, the proposed insecticidal chlorocyclopsylmethylthiophosphoric acid
q) the body has an enhanced effect. and an additive selected from the group: carrier |

权利要求:
Claims (1)
[1]
Claims of the invention with the fact that, in order to enhance the insecticide J noto action, it contains as a pro-insecticidal agent containing dehydrated dichlorocyclopropyl methyl thiophosphorus
based on the derivatives of the di-acid compound of the general formula
where R is hydrogen, methyl; Y is oxygen ,, sulfur,
R is hydrogen; in the amount of 0.5-99 wt.%. R is hydrogen, methyl; d4 s, -Cr-alkoxy, C ,, - Ce-alkylthio, Sources of information.
butynylthio, benzylthio, dimethyl-taken into account during examination
amino; 1- US Patent N 2945054, cl. 260-461,
. R is Ci-Cj-alkyl, otlubic. 12.07.60.
thinner and solubilizer, distinguished, X.
 CHi-S-p
R

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同族专利:

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SU725543A3|1980-03-30|

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BE856380A|1978-01-02|

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IL52279A|1980-12-31|

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FR2360600A1|1978-03-03|

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NL7708446A|1978-02-02|

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CH629368A5|1982-04-30|

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DE2634587A1|1978-02-02|

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GB1579592A|1980-11-19|

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HU178431B|1982-05-28|

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JPS5318543A|1978-02-20|

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US4171357A|1979-10-16|

引用文献:

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公开号 | 申请日 | 公开日 | 申请人 | 专利标题

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US2945054A|1958-08-21|1960-07-12|Eastman Kodak Co|O, o-dialkyl s-[1- ethyl] phosphorothiolothionates|

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IL30533A|1967-09-01|1972-01-27|Bayer Ag|Thiol-or thionothiol-phosphoric or-phosphonic acid esters|DE2934229A1|1979-08-24|1981-03-26|Basf Ag, 67063 Ludwigshafen|2,2-DICHLORCYCLOPROYL-METHYL-PHOSPHORSAEUR DERIVATIVES, METHOD FOR THE PRODUCTION THEREOF AND THEIR USE FOR CONTROLLING PESTS.|

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US4535077A|1981-08-28|1985-08-13|Fmc Corporation|O-ethyl S,S-dialkyl phosphorodithioates for use as pesticides|

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DE3434281A1|1983-09-29|1985-04-11|Sandoz-Patent-GmbH, 7850 Lörrach|Process for the dyeing of wool or wool/polyamide fibre blends with acid dyes|

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DE3704123A1|1987-02-11|1988-08-25|Basf Ag|BISTHIOL PHOSPHATES, METHOD FOR THE PRODUCTION THEREOF AND THEIR USE FOR CONTROLLING Pests and MEDIUM THEREFOR|

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DE3819632A1|1988-06-09|1989-12-14|Bayer Ag|O-HALOGENCYCLOBUTYL-S-ALKYL-THIOPHOSPHONACID ESTER, METHOD FOR THE PRODUCTION THEREOF AND THEIR USE AS A PEST CONTROL|

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DE4242502A1|1992-12-16|1994-06-23|Rhein Chemie Rheinau Gmbh|Metal-free dithiophosphoric acid derivatives|

法律状态:

优先权:

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申请号 | 申请日 | 专利标题

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DE19762634587|DE2634587A1|1976-07-31|1976-07-31|CYCLOPROPYL-METHYL-PHOSPHORIC ACID DERIVATIVES|

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