Dithiocarbamate plant fungicides

Details Dithiocarbamate plant fungicides Dithiocarbamate plant fungicides

1984-05-21

1986-09-23

Jiles, Henry R.

Drug, bio-affecting and body treating compositions

Designated organic active ingredient containing

N-c doai

558235, 558236, A01N 4710, C07C15508

Patent

active

046136150

DESCRIPTION:

BRIEF SUMMARY
The invention relates to plant protecting composition which contains 1 to 80% by weight substituted alkoxycarbonyl dithiocarbamates or thiolcarbamates of formula (I) ##STR4## wherein R.sup.1 and R.sup.2 are the same or different and stand for hydrogen, straight or branched chain, saturated or unsaturated alkyl, alkoxyalkyl, alkylaminoalkyl, dialkylaminoalkyl having 1 to 10 carbon atoms, cycloalkyl, phenyl or halogenphenyl, alkyl, cycloalkyl, phenyl or halogenphenyl, and by weight additive(s).
A further feature of the invention is a process for the preparation of the novel substituted alkoxycarbonyl dithiocarbamates or thiolcarbamates of formula (I).
An essential field of the modern plant protection on a large-scale is chemical plant protection. Thus it can be prevented, that a variety of pests can ruin a great part of the harvest. In the last few years many plant protecting compositions were used in the practice against the fungal pests of the cultivated plants. The use of these compositions resulted, however, in some resistance. So novel compositions should be found by which the rotation of the composition may be assured and the resistant fungi may be killed.
In the 1950s and 1960s dithiocarbamates were found to be useful against several fungal pests, e.g. branches Botrytis, Phytophtora infestans and Venturia inaeqailia (U.S. Pat. Nos. 2,457,674 and 2,974,156 and GBP No. 996,264). These are not systemic fungicides so repeated spraying is necessary.
Fungicidal S-alkyl dithiocarbamates are also known (U.S. Pat. No. 2,695,901). The disadvantage of these fungicides is that they cannot be used in every culture and owing to the resistance increasing doses are needed.
In view of the above described novel plant protecting compositions should be found which do not show the disadvantages of the known compositions and the rotation of the composition being necessary for the safe production may be solved.
It was found that the known disadvantages of the fungicidal dithiocarbamates may be eliminated when a composition is used which contains 1 to 80% by weight substituted alkoxycarbonyl dithiocarbamate and/or thiolcarbamate of formula (I), 10 to 90% by weight solid and/or liquid diluent(s) and 1 to 30% by weight additive(s), preferably tensides.
The meaning of the substituents in the substituted alkoxycarbonyl dithiocarbamates or thiolcarbamates may be the following: R.sup.1 and R.sup.2 may be the same or different and may stand for straight or branched chain, saturated or unsaturated alkyl, alkoxyalkyl, alkylaminoalkyl, dialkylaminoalkyl having 1 to 10 carbon atoms, cycloalkyl, phenyl or halogenphenyl; R.sub.3 may stand for straight or branched chain, saturated or unsaturated alkyl, cycloalkyl, phenyl of halogenphenyl and X may stand for oxygen or sulfur.
The composition of the invention may be used e.g. against the pests Fusarium graminearum, branches Botrytis, Phytopthora infestans, Venturia inaequalia and cause no damaging effects in the cultivated plants.
A feature of the invention is the process for the preparation of the substituted alkoxycarbonyl dithiocarbamates and thiolcarbamates of formula (I). According to this process the compounds of the invention are prepared in such a way that a salt of a disubstituted dithiocarbamic acid or thiolcarbamic acid of formula (II) ##STR5## wherein R.sup.1, R.sup.2 and X have the same meanings as defined above and chloroformic acid ester of formula (III) ##STR6## preferably in aqueous medium at a temperature of 0.degree. C. to 60.degree. C.
The preparation of the compounds of formula (I) is further shown in the following Examples.


EXAMPLE 1

56.4 g (0.25 moles) of diethyl dithiocarbamic acid sodium.times.3H.sub.2 O and 250 ml of water are charged into a 500 ml round-bottom flask equipped with a stirrer, thermometer and feed hopper thereafter 30.7 g of chloroformic acis isopropyl ester are added at 5.degree. to 10.degree. C. for 30 minutes. The reaction mixture is stirred further for 30 minutes at 10.degree. C. then the N,N-diethyl-S-isopropyloxycarbonyl dithiocarbamate obta

REFERENCES:
patent: 3352815 (1967-11-01), Bencze

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