专利摘要:
Symmetrical N-substituted bis-carbamoyl sulfide compounds exhibit exceptional broad spectrum pesticidal activity coupled with extremely low mammalian toxicity and phytotoxicity.
公开号:SU797543A3
申请号:SU762425651
申请日:1976-12-01
公开日:1981-01-15
发明作者:Дамаскено Йоахим Дъсильва Темистоклес
申请人:Юнион Карбид Корпорейшн (Фирма);
IPC主号:
专利说明:

in which R and R have the foregoing meaning. Two equivalents of the oxime reagent enter the reaction with bis-carbamoyl fluoride in the presence of two equivalents of the acid acceptor, preferably in an inert solvent. The acid acceptor can be either an organic or inorganic base / such as triethylamine or sodium or potassium hydroxide. You can use any suitable inert solvent such as benzene, toluene, diethyl ether, tetrahydrofuran, ethyl ether, methylene chloride etc. The reaction is carried out in a two-phase system using an aqueous solution of an inorganic base as the first phase and an aromatic solvent containing a ammonium chelate as the transfer agent for Laza as the second phase. The reaction temperature is not a decisive factor. Significantly, the reaction ends at room temperature. Higher temperatures can be used if necessary to shorten the reaction time. Another method of obtaining symmetrically} with bis-carbamoyl sulfide compounds of Lormula {I) is represented by the following reaction scheme; R, O V and 2 i KOCiN 4 $ jCilt H 8 C NOCNSNC in accordance with this method, two equivalents of carbamate compounds react with sulfur chloride in the presence of two equivalents of an acid acceptor, such as pyridine, preferably in a solvent, as a result of which Symmetric bis-carbamoyl sulfides (I) are obtained. Following examples of illk) are striking to a low efficiency of the proposed method. A suspension of the test compound is prepared by dissolving 1 g of the compound in 50 ml of acetone in which O is dissolved, 1 g (10% by weight of the compound) of alkylphenoxy-polyethoxyethanol, a surface active substance, which is used as an emulsifying or dispersing agent. The resulting solution is mixed with 150 ml of water, resulting in approximately 200 ml of a suspension containing the above compound, in a co-grinding form. The initial suspension thus prepared contains 0.5% by weight of a compound of formula (I). Concentrations in parts by weight per million, which are used in the tests, are described in detail below and are obtained by appropriate dilution of the initial suspension with water. In the study used the following methods of verification. Adult specimens, as well as larvae that are in the preduminal period of development, bean aphids (Aphis fabae Scop), grown on potted dwarf nasturtium plants at a temperature of 18-21 ° C and relative humidity of 50-70%, serve in this case is tested by insects. For verification purposes, the standard for the number of specimens per one pot is introduced; this number is 100-150 insects. If there is a greater number of aphids on the plant, their number on the plant is reduced in order to bring this number closer to the aforementioned standard. Plants grown in pots (one pot for one verifiable compound) are infected with 100,150 aphids, and then marked on a turntable, where they are treated by spraying, 100,110 ml of the test compound of the required concentration; in this case, a group of De Wilbiss pulverizers is used and an overpressure of 2.8 kg / cm. Such a treatment, which lasts for 25 seconds, is quite sufficient to wet the plants before the runaway stage. As a control of the experiment, 100-110 ml of a water-acetone-emulsifier solution not containing the test compound is also sprayed onto infected plants. After the above treatment, the pots are placed in place on a sheet of white standard paper for the mimeograph apparatus, which was previously lined in order to facilitate the counting procedure. The temperature and humidity in the room where the experiments were conducted are maintained for 24 hours at a level of 18-2lc and 50-70%, respectively. A ton which falls on the paper and which is not able to maintain the normal position of its body after it has been given a normal position is considered as lost. The aphid specimens that remain on the plants are carefully studied for their movement; and those who are not able to move the length of their heat when stimulated with a sharp object with shots are considered dead. Percentage of aphid infestations at various concentrations is recorded. In the next test, the larvae of the southern meadow moth (Spodoptera eredania, (Cram.)), Which is cultured on spinach mustard plants at 26 and relative humidity 50 ± 1%, are examined as insects to be tested. The desired concentration of the test compound is obtained using diluting the initial suspension with water to obtain a suspension containing 500 parts of the tested compound per million parts of the final volume. Planted spinach mustard plants of standard height and age are placed on a rotary table l and treated with a spray of 100-110 ml of a pro-wound compound, using a series of dB Wilbiss spray guns with an excess air pressure of 0.7 kg / cm. This treatment, which | Torus lasts for 25 s, is quite sufficient for in order to wet the plants up to the degassing stage. To control the experiment, 100-110 m of a solution containing water, acetone and an emulsifier, but not containing a test-a-compound, is also divided into infected plants. After drying, the sticky leaves are separated and each sheet is placed in a 9 cm diameter Petri dish, equipped with moistened filter paper. Five randomly selected larvae injects into each cup, and then the cups are closed. Closed cups are labeled and maintained at 26.5-2S, C for three days. Larvae that are unable to move their full body length even when stimulated at. assisted shots with a sharp object are considered dead. The percentage of dead larvae is recorded at various concentrations. In the next test, the tested insects are considered; Mexican legume beetle larvae (Epiiachne varivestis, Mu 1 s.). found in the fourth stage of insect development, which are cultivated on spinach mustard plants at 26, and a relative humidity of 50 ± 5%. Spinach-horned plants, about the same height and age, are placed on the turntable and processed by spraying with an lOO-llO ml suspension of the tested Compound, using a series of De Vilbiss sprayers with an excess air pressure of 0; 7 kg / cm This treatment, which it lasts for 25 seconds, quite sufficient to wet the plants to the runaway stage. To control the experiment, 100-110 ml of a solution containing water, acetone, and an emulsifier, but not containing the test compound, are also sprayed onto infected plants. After drying, the agglomerates are separated and each sheet is placed in a 9 cm diameter Petri dish equipped with a moistened filter paper. Five randomly selected larvae are placed in each cup, and then the CSMs are closed. Closed cups are labeled and maintained at 26.5 + 3 ° C for three days. Larvae that are not able to move the entire length of their body, even when stimulated, are considered dead. In the next test, adult domestic flies, aged four to six days (Musca domestica, i.), Which were grown under controlled conditions, temperature 26, and relative humidity, are considered as tested insects. 50 + 5%. The flies were euthanized by carbon dioxide anesthesia and twenty-five fixed specimens, females and males, were placed in an insect cage containing a standard food filter, approximately 12.7 cm in diameter, which was turned over a wrapped paper surface. The desired concentration of the test compound is achieved by diluting the initial suspension with a 10 wt.% Sugar solution. 10 ml of the suspension containing the test compound is added to an evaporating dish, which contains an extra large, with a side of 2.54 cm, an absorbent pillow made. from cotton. This bait cup is positioned and centered on absorbent paper under the food filter before it is put to sleep by flies in an insect cage. Flies placed in the cage are given the opportunity to eat food on a bait for 24 hours, while they are kept at 26 and at a relative humidity of 50 ± 5%. Flies that show no signs of movement during stimulation are considered dead. In the next test, adults and the doped mite larvae (Tetranychus urticae Koch), which are grown at the prepupolar stage, are considered as test organisms, which are grown on spinach mustard plants at 50 ± 5% relative humidity and at 26.5 ± 3 ° WITH. Infected leaves from the original culture are placed on the first-leaves of two legume plants, 15 to 20 cm in height, which are grown in clay pots in size, see. For dough, 150–200 ticks are sufficient; they crawl from cut infectious casts to fresh plants for 24 hours. After 24 hours, during which the bream crawls to fresh plants, cut leaves are removed from the warasse plants, planted in plant pots (based on: ONE pot per compound) on a rotary table and processed, with a spray of 100-110 MP. suspension containing a test compound-, using a series of pulverizers De VilOissa with an excess air pressure of 2.8 kg / cm. This treatment, which continues for e 25, it is sufficient to moisten chtby plants to step escaping. To control the experiment, 100-110 ml of an aqueous solution containing acetone and an emulsifier in the same concentrations as in the suspension containing the test compound, but not containing the test compound, also
sprinkled on infected plants. Treated plants were kept in a relative humidity of 80 ± 5% for 6 days. Thereafter, the number of dead, larvae that are at the stage of moths is calculated. A study of the state of the larvae is carried out on the leaves of the tested plants using a microscope. Any larva that is capable of n movement during stimulation is considered alive.
The results of biological activity (LOjQ in parts by 10) are presented in Tables 1 and 2, which also indicates mammalian toxicity 5 and phytotoxicity. Phytotoxicity was rated on a scale of 1 to 5 (1 lack of povreladeni, 5 - dead plants).
ABOUT
“OT)
about
VO
about

with
about o tn l
m
tn
01
o o in
in
CN TN
00
Mr. I
Mr. S
X
5 o
V% J .in.
P
at
0 | L
about
in
lii and.
.
- t
15: -in
o- rrtJ o
Yu
five
; n
oh hell
F
V
VO VO
sh
about o in l
00
oo
about o in l
about o in
about a
g
00
.uzh about
°) With
0-0
and
 l
AND
Vv,
;

15
/
"
well
x
.about
go
about
00
t-o o in l
about
1GT V
VO
oh
00 VO
fM
CTi
oh oh
00
about
with
about o "l
about
l
oh oh
about p
1L
V
l
oh oh
oh oh
1L.
1L
l
about about shl
in
g- (
SP
1L
00
n I o
g- so
P
/)
.
u
x
that
About "VO
ABOUT
"
about o in
oh oh
1L
l
about
about
1L
oh oh
1L
l
I
and about “m g
OshP.tO
CMk -
a- "o-t"
. "about
lf
and v 15
p PMVO
oh oh
R
1L N
about
(L
r
(M go
1L
and
(N
I o
ii
  J
l-i-s
about

LO, h / 10
faces
权利要求:
Claims (1)
[1]
Claim
A method for controlling insects and mites by treating them and their biotope with an active principle based on symmetric N-substituted bis-carbamoyl sulfides, characterized in that, in order to increase the efficiency of the method, they are processed by symmetric N-substituted bis-carbamoyl sulfides of the general formula where R 4 is hydrogen, methyl, Ν, Ν-dimethyl carbamoyl, ethoxycarbonyl;
R ^ is methylthio, isopropylthio, cyanethylthio, methylsulfonylisopropyl, cyanisopropyl or
R ^ together with the adjacent carbon atom form 1,3-dithiocyclopentene, 1,4-dithiocyclohexene,
5-methyl-1,3-oxothiolone, 3,5,5-trimethyl-1, 3-thiazol-4-one ring in an amount of 0.25 to 15 kg / ha.
类似技术:
公开号 | 公开日 | 专利标题
SU797543A3|1981-01-15|Method of insect and mite control
SU656466A3|1979-04-05|Herbicide composition
DE2654314C2|1987-06-25|
SU691062A3|1979-10-05|Insecticide
USRE27347E|1972-04-25|Vii.chs
US3784605A|1974-01-08|2-|-1,3-indandione compounds
US4096269A|1978-06-20|N-haloalkane-sulfenylcarbamoyl oxime pesticides
SU428588A3|1974-05-15|INSECTICIDE
SU539503A3|1976-12-15|The way to combat harmful insects and mites
SU805934A3|1981-02-15|Insectoacaricidobactericidic agent
DE2462422A1|1977-03-03|2-CARBAMOYLOXIMINO-1,4-OXATHIACYCLOHEXANE AND THEIR 4-OXIDES AND 4,4-DIOXIDES AND METHOD FOR THEIR PRODUCTION
US3992549A|1976-11-16|Pesticidal compositions and methods of killing pests using N-polyhalo-alkanesulfenyl carbamoyloximino di-sulfur containing heterocyclic compounds
SU663263A3|1979-05-15|Insecticide
SU843696A3|1981-06-30|Herbicidic composition
SU1134563A1|1985-01-15|Phosphorus esters of cyanohydrins having insectoacaricidal effect
SU609456A3|1978-05-30|Insecticide-acaricide-nematocide
SU645522A3|1979-01-30|Insecticide-acaricide composition
SU644360A3|1979-01-25|Insecticide, acaricide and nematocide composition
US4003895A|1977-01-18|1,4-Thiazines
US4003897A|1977-01-18|Carbamate pesticidal compounds
SU555827A3|1977-04-25|Herbicidal composition
SU376915A1|INSECTICIDE AND ACARICIDE
SU385418A1|PATCH AND TECHNICAL
SU589891A3|1978-01-25|Method of fighting insects and ticks
David et al.1959|The action of the systemic insecticide fluoroacetamide on certain aphids and on Pieris brassicae |
同族专利:
公开号 | 公开日
OA06290A|1981-06-30|
PL117602B1|1981-08-31|
DK537776A|1977-06-02|
AR220889A1|1980-12-15|
ES456142A1|1978-01-16|
PT65909B|1978-05-23|
DE2654331C2|1987-12-03|
MY8100079A|1981-12-31|
PH18081A|1985-03-18|
AU515066B2|1981-03-12|
BR7608000A|1977-11-08|
PL194037A1|1978-10-23|
OA05499A|1981-04-30|
US4382957A|1983-05-10|
GT197644023A|1978-05-24|
IL51003A|1981-11-30|
GB1557332A|1979-12-05|
PT65909A|1976-12-01|
CH619690A5|1980-10-15|
SU799655A3|1981-01-23|
ZA766634B|1977-10-26|
CA1062271A|1979-09-11|
PH16340A|1983-09-05|
TR20241A|1980-11-27|
DD136263A5|1979-06-27|
NZ182771A|1978-11-13|
NL186859B|1990-10-16|
IN145086B|1978-08-19|
EG12452A|1991-08-30|
FR2333787B1|1982-12-17|
DD128956A5|1977-12-21|
CH618966A5|1980-08-29|
YU289376A|1982-10-31|
JPS5268104A|1977-06-06|
PL114557B1|1981-02-28|
RO70956A|1982-05-10|
SU918292A1|1982-04-07|
PH16270A|1983-08-25|
ATA885276A|1979-07-15|
RO78161A|1982-02-01|
SU895285A3|1981-12-30|
DE2654331A1|1977-07-07|
DK170333B1|1995-08-07|
ZM13876A1|1977-08-22|
JPS57145865A|1982-09-09|
MW4876A1|1978-04-12|
AT355041B|1980-02-11|
SE436495B|1984-12-17|
YU144282A|1982-10-31|
GR61348B|1978-10-26|
IL51003D0|1977-01-31|
CS191325B2|1979-06-29|
JPS594428B2|1984-01-30|
NL7613333A|1977-06-03|
MX4376E|1982-04-19|
NL186859C|1991-03-18|
SE7613428L|1977-06-02|
ES453816A1|1977-11-16|
FR2333787A1|1977-07-01|
AU2006576A|1978-06-08|
HU176034B|1980-11-28|
IT1125228B|1986-05-14|
BE848912A|1977-05-31|
引用文献:
公开号 | 申请日 | 公开日 | 申请人 | 专利标题

US3920830A|1970-07-14|1975-11-18|Chevron Res|Insecticidal n-thio)aryl carbamates|
US3794733A|1970-11-09|1974-02-26|Chevron Res|N-substituted arylcarbamoyl sulfides used as insecticides|
US3679733A|1970-11-09|1972-07-25|Gustave K Kohn|N-substituted arylcarbamoyl sulfides|
DE2530439C2|1974-07-11|1983-03-03|CIBA-GEIGY AG, 4002 Basel|Bis- [0- -N-methyl-carbamic acid] -N, N'-sulfides, processes for their preparation and pesticides containing these compounds|
CH596757A5|1974-07-11|1978-03-15|Ciba Geigy Ag|N,N'-thiobis-N-methyl-carbamates)|DE2803253A1|1978-01-26|1979-08-02|Bayer Ag|N-SULFENYLATED CARBAMOYL OXIMES, METHOD FOR THE PRODUCTION THEREOF AND THEIR USE AS INSECTICIDES, ACARICIDES AND NEMATOCIDS|
US4288455A|1978-02-15|1981-09-08|Union Carbide Corporation|Method of controlling mollusc pest|
JPS5737562B2|1978-06-28|1982-08-10|
BR8001185A|1979-03-06|1980-11-04|Du Pont|CARBAMOILE SULPHIDE COMPOUND, AGRICULTURAL COMPOSITION PROCESS FOR THE CONTROL OF INSECTS OR NEMATOIDS AND PROCESS FOR PREPARING A CARBAMOILE SULFIDE COMPOUND|
US4393074A|1980-04-14|1983-07-12|E. I. Du Pont De Nemours And Company|Fluorinated carbamate insecticides|
US4323578A|1979-08-10|1982-04-06|E. I. Du Pont De Nemours And Company|Fluorinated carbamate insecticides|
US4394386A|1980-04-14|1983-07-19|E. I. Du Pont De Nemours And Company|Fluorinated carbamate insecticides|
US4255353A|1979-10-22|1981-03-10|E. I. Du Pont De Nemours And Company|Sulfinyl-bis carbamoyl fluorides|
US4291054A|1979-12-10|1981-09-22|E. I. Du Pont De NemoursAnd Company|Insecticidal carbamoyl sulfides|
BR8104086A|1980-07-03|1982-03-16|Du Pont|PROCESS FOR TICK CONTROL|
AR229041A1|1981-01-21|1983-05-31|Union Carbide Corp|NON-REPLACED AQUEOUS NON-REPLACED PESTICIDE CONCENTRATE|
JPH0124144B2|1981-11-27|1989-05-10|Ootsuka Kagaku Kk|
US5157050A|1985-04-18|1992-10-20|Miles David L|Thermally stabilized bis alkylthio-alkylamino-N-alkyl carbamates|
USH563H|1985-12-12|1989-01-03|Use of sulfur-containing compounds for controlling plant parasitic nematodes|
HU196055B|1985-12-20|1988-09-28|Innofinance Bp Altalanos Innov|Insekticide compositions containing esters of carbaminic acid as active component and process for producing the active components|
法律状态:
优先权:
申请号 | 申请日 | 专利标题
US05/636,373|US4382957A|1975-12-01|1975-12-01|Symmetrical insecticidal bis-carbamate compounds|
[返回顶部]