Drug – bio-affecting and body treating compositions – Designated organic active ingredient containing – Having -c- – wherein x is chalcogen – bonded directly to...
Patent
1999-02-03
2000-09-05
Robinson, Allen J.
Drug, bio-affecting and body treating compositions
Designated organic active ingredient containing
Having -c-, wherein x is chalcogen, bonded directly to...
514107, 514108, 514114, 514129, 514140, 514141, 514269, A01N 4354, A01N 5700, A01N 5718
Patent
active
061143405
DESCRIPTION:
BRIEF SUMMARY
This application is a 371 of PCT/GB97/01738, filed Jun. 26, 1997.
FIELD OF THE INVENTION
This invention relates to new fungicidal compositions.
PRIOR ART
U.S. Pat. No. 2,927,014 discloses phosphonates and phosphinates having herbicidal activity. In WO 9418837 and WO 9304585, it is disclosed that certain phosphonates can enhance the activity of specified herbicides. We have now found that such compounds can also be used with advantage in association with certain fungicides used to combat phytopathogenic fungi.
DESCRIPTION
The invention provides a fungicidal composition which comprises a mixture of
(a) fluquinconazole or azoxystrobin, and
(b) at least one phosphonate or phosphinate of formula I ##STR1## where
R.sup.1 is C.sub.6-20 -alkyl, C.sub.6-20 -alkoxy or optionally substituted phenyl
R.sup.2 is benzyl, C.sub.6-20 -alkyl, optionally interrupted by NH or O, di-C.sub.6-20 -alkylamino or the group ##STR2## and
R.sup.3 is C.sub.6-20 -alkyl.
Phosphonates of formula I wherein R.sup.1 is C.sub.6 -C.sub.20 -alkoxy and R.sup.2 is C.sub.6 -C.sub.20 -alkyl are known. They are made for example according the disclosure in DE 1,963,014.
Phosphinates of formula I wherein R.sup.1 is C.sub.6 -C.sub.20 -alkyl and R.sup.2 is phenyl can be prepared by catalytically induced addition of olefins to phenyl monoalkylphosphonites which are preferably prepared as described in DE patent 196 041 95.
Ethane-1,2-diphosphonic acid tetraalkyl esters of formula I wherein R.sup.1 is C.sub.6 -C.sub.20 -alkoxy and R.sup.2 is the group ##STR3## can be made by addition of the appropriate phosphonates to a dialkyl vinylphosphonate in the presence of basic catalysts such as sodium methylate or sodium hydride.
Alkyl- or dialkylaminoalkylphosphonic acid dialkyl esters of the formula ##STR4## wherein R.sup.3 is as defined above and R.sup.5 is R.sup.3 or hydrogen and x is 0 or 1 can be prepared according to two different methods. Compounds wherein x is 0 are made according to the following equation ##STR5## Compounds wherein x is 1 and made according to the following equation: ##STR6##
The addition of the amine is made in the presence of basic catalysts such as sodium methylate of sodium hydride according to the process described by A. N. Pudovik et al., Doklady Akad. S.S.S.R. 80365(1951); (A 50, 4143(1956).
Azoxystrobin is the common name for the fungicide methyl (E)-2-{2-[6-(2-cyanophenoxy)pyrimidin-4-yloxy]phenyl}-3-methoxyacrylate and fluquinconazole is the common name for the fungicide 3-(2,4-dichlorophenyl)-2-(1H-1,2,4-triazol-1-yl)-4(3H)-quinazolinone).
We have found that phosphonates of formula I, which have little or no activity in their own right considerably enhance the fungicidal activity of fluquinconazole and azoxystrobin.
The weight ratio of component a) to b) is generally between 10:1 and 1:10, preferably between 3:1 and 1:5.
The compound of formula I can be added to conventional formulations of component a). It may be desirable to also add small quantities of solvent and/or surfactant especially a non-ionic surfactant, and other additives such as fatty acids to improve the emulsifiability of the compound of formula I.
The following Examples illustrate the invention. Examples 1 to 6 describe the preparation of what are believed to be novel phosphonates and phosphinates, which can be used in admixture with azoxystrobin or fluquinconazole.
EXAMPLE 1
Into a reaction vessel, which was heated to 100.degree. C., with a reflux condenser (-15.degree. C.), were simultaneously added aqueous formaldehyde (12.17 g of 37% solution) and a mixture of di(2-ethylhexyl)amine (36.22 g) and di(2-ethylhexyl) phosphonate (45.96 g). The mixture was heated for 1 hour with stirring and then cooled to 20.degree. C. The water was removed by distillation under reduced pressure to give di(2-ethylhexyl){[di(2-ethylhexyl)amino]methyl}phosphonate, as a colourless liquid (n.sub.D.sup.20 =1.4563).
EXAMPLE 2
A mixture of 2-ethylhexyl vinylphosphonate, 2-ethylhexylamine (66.50 g) and sodium hydride (0.10 g) was stirred at 130.degree. C. for 6 hours. Af
REFERENCES:
patent: 2570503 (1951-10-01), Tawney
Chemical Abstracts, vol. 75, No. 7, 1971 Columbus, Ohio, US; Abstract No. 49254, A.N. Pudovik, et al.: "Reaction of phosphonites and phosphinites with tin tetrachlorides".
Chemical Abstracts, vol. 92, No. 20, 1980 Columbus, Ohio, US; Abstract No. 166963, R.R. Shoun, et al.: "Bidentate organophosphorus compounds as extractants from acidic waste solutions".
Y. Xu, et al.: "Studies on N,N-disubstituted dialkyl 2-aminophosposhonates and derivatives thereof"; Synthesis, vol. 5, 1990, Stuttgart, Germany, pp. 427-429.
Chemical Abstracts, vol. 62, No. 1, 1965 Columbus, Ohio, US; Y. Y. Hsu, et al.: "Organophosphorus compounds. III. Dialkyl N,N-disubstituted aminomethylphosphonates and their derivatives"; col. 1317c.
Briggs Geoffrey Gower
Buschhaus Herbert
Hagemeister Heinz
Jende Hans-Peter
Kleiner Hans-Jerg
Agrevo UK Limited
Robinson Allen J.
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