Drug – bio-affecting and body treating compositions – Designated organic active ingredient containing – Having -c- – wherein x is chalcogen – bonded directly to...
Reexamination Certificate
2001-03-30
2003-06-24
Rotman, Alan L. (Department: 1625)
Drug, bio-affecting and body treating compositions
Designated organic active ingredient containing
Having -c-, wherein x is chalcogen, bonded directly to...
C514S512000, C549S473000, C558S245000, C558S246000
Reexamination Certificate
active
06583175
ABSTRACT:
FILED OF THE INVENTION
The present invention relates to novel alkylxanthates of formulae 1 to 3 and use of alkylxanthates of formulae 1 to 6 in the integrated pest management, more specifically alkyl xanthates are used as insect growth regulators for pest management in agricultural fields no or less environmental impact.
BACKGROUND AND PRIOR ART REFERENCES
Many small scale farmers are illiterate and believe in the usage of high volumes, high pressure, and high doses of pesticide as the most suitable way of crop protection, these practices have resulted in many environmental problems such as effect on non-target species, pesticide residue accumulation, variable selectivity, development of resistant in pests, ecological imbalance by elimination of natural predators as well as and environment pollution. More than 50% of the pesticides used in third world countries are globally banned and 95% of the used by the public health sector also find restricted use in other nations (News corner, Pesticide World, 1998). There are 33 pesticides, which have been banned in advanced countries, but they are allowed to be imported and used in third world countries (Insecticides Act, 1968 and Indian Express Newspaper January, 2000). In order to restrict the use of banned pesticides, they must be replaced with suitable pesticides that must be target specific, non-toxic to other species, easily biodegradable and less persistent. Hence, the advanced countries are mainly concentrated to identify the IV generation of insecticides, which are highly effective and generally selective agents derived for tactical skills. It requires more management expertise which are far friendlier to the total environment including the biological control organisms.
The applicants have isolated a Ethylene Bis (isobutylxanthate) (1) from a green alga
Dictyosphaeria favulosa
(Venkateswarlu et al, 1993). It was tested against various aquatic stages of
Aedes aegypti
mosquito, which is a yellow fever vector. The compound 1 exhibited larvicidal and insect growth regulatory activity in dose dependent mannar (Venkateswarlu Rao et al., 1995). Around thirty-five analogues were synthesised and tested against agricultural polyphagous lepidopteron pests. Among them four analogues have been identified as good antifeedant and insect growth regulators. Two of the compounds from the four analogues are totally new structures and remaining two are structurally known but the activity was identified for the first time.
Compound I: Ethylene Bis (isobutylxanthate)
Physical state: Colorless solid
M.P.: 40-42° C.
Molecular formula: C
12
H
22
O
2
S
4
EIMS (70 eV): m/z 326
Elemental analysis: Found: C 44.15%, H 6.90%, S 39.15% Required: C 44.13%, H 6.79%, S 39.28%
IR(KBr): V
max
(KBr) 2950, 1465, 1235, 1200, and 1140 cm
−1
UV(MeOH): &lgr;
max
(MeOH) 217 (&egr; 12735), 232 (14766) and 278 nm
(20048)
1
H NMR: (CDCl
3
, 200 MHz) &dgr; 1.0 (6H, d, J=7.5 Hz), 2.15 (1H, m),
In 1950 S. V. Zhuravlev, reported the synthesis of ethylene dixanthates (2-5). Heating the mixture of 4.7 gms (CH
2
Br
2
)
2
and EtOCS
2
K in ethanol on a steam bath gave ethylene dixanthate (yield 90%). In which compounds 2 and 5 possess a moderate insecticidal activity against lice.
In 1954 Yamasaki, reported the synthesis of organophophorus compounds (xanthgenates). A series of xanthogenates (6-10) were synthesized in three ways.
here M=alkali metal
6 R′=Me; R=Me
7 R′=n-propyl; R=ethyl
8 R′=ethyl; R=ethyl
9 R′=sopronyl; R=ethyl
10 R′=n-butyl; R=ethyl
In 1950 S. V. Zhuravlev, reported the synthesis of p-xylene dixanthates. MeOCS
2
K reacted with p-C
6
H
4
(CH
2
Cl)
2
in ethanol gave p-xylene bis (methylxanthate) (yield 75.5%). A series of p-xylene bis xanthates has been synthesized (11-20). All these bis xanthates are insecticides with low order of activity.
11 R=ethyl
12 R=n-butyl
13 R=isobutyl
14 R=octyl
15 R=isooctyl
16 R=nonyl
17 R=decyl
18 R=cyclohexyl
19 R=phenethyl
20 R=benzyl
The dixanthates were dissolved in refined kerosene to form a 25% solution was used as a efficient defoliants for cotton plants (Cupery, 1958).
Etylene Bis (isopropylxanthate) (21) and ethylene bis(isobutylxanthate) (1) were used as noncorrosive antiseize lubricating oil additives (Khalikov and Vinogradova, 1964).
Methylene bisxanthates are used as collector reagents in the froth flotation of sulfide minerals (Saphores, et al., 1991).
Ten newly synthesized organo phosphorus derivatives containing alkyl xanthates were tested for their antifungal activity against
Colletotrichum falcatum, Fusarium oxisporium, Curvularia pallescens
(sugarcane pathogens). The O,O-diethyl thio phosphate derivatives exhibited 100% mycelial inhibition against all the test fungi at 1000 ppm. All thio phosphate derivatives showed fungistatic effects at a minimum inhibitory concentration of 1000 ppm. These derivatives also proved better than currently used synthetic fungicides (Senguptha et al., 1998).
In the course, the applicants have synthesized ethylene bis (isobutylxanthate) and its analogues. In which compound 25, 27 and 28 are newly synthesized compounds and these compounds were tested for antifeedant and larvicidal activities.
OBJECTS OF THE INVENTION
The main object of the invention is to provide novel alkylxanthates for agricultural applications.
In another object of the invention is to provide a new use of novel alkylxanthates for use in integrated pest management.
In still another object is to provide a new activity of alkylxanthates for use in integrated pest management.
In yet another object is to provide a process for the preparation analogues of alkyl xanthates useful as an antifeedent and as insect growth regulators.
In yet another object is to provide a composition useful as an insect growth regulator and antifeedant for the integrated pest management.
SUMMARY OF THE INVENTION
The present invention relates to novel alkylxanthates of formulae 1 to 3 and use of alkylxanthates of formulae 1 to 6 in the integrated pest management, more specifically alkyl xanthates are used as insect growth regulators for pest management in agricultural fields no or less environmental impact.
REFERENCES:
patent: 3845092 (1974-10-01), Schneider et al.
patent: 3919281 (1975-11-01), Marubashi et al.
patent: 5011965 (1991-04-01), Saphores et al.
“Pesticide use in India doubled in eight years”,Pesticides World, Apr.-May, 1998, p. 43.
“Pesticides—Banned elsewhere, used in India”, Indian Express Newspapers (Bombay) Ltd., Saturday Dec. 9, 2000.
Venkateswarlu et al., “Ethylene Bis (Alkylxanthate) form a Green AlgaDictyosphaeria Favulosa#”, Tetrahedron Letters, vol. 34, No. 22, pp. 3633-3634, 1993.
Raghavan Kondapuram Vijaya
Rao Janapala Venkateswara
Venkateswarlu Yenamandra
Council of Scientific & Industrial Research
Covington Raymond
Oliff & Berridg,e PLC
Rotman Alan L.
LandOfFree
Alkylxanthates and use of alkylxanthates in the integrated... does not yet have a rating. At this time, there are no reviews or comments for this patent.
If you have personal experience with Alkylxanthates and use of alkylxanthates in the integrated..., we encourage you to share that experience with our LandOfFree.com community. Your opinion is very important and Alkylxanthates and use of alkylxanthates in the integrated... will most certainly appreciate the feedback.
Profile ID: LFUS-PAI-O-3135872