Claims
- 1. A compound selected from the group consisting of those of the formulae: ##STR6##and ##STR7## wherein Y is selected from nitro and trifluoromethyl; X is selected from alkyl and alkenyl of up to 6 carbon atoms, nitro, trichloromethyl, trifluoromethyl, trifluoromethoxy, trifluoromethylthio, trifluoromethylsulfoxy, trifluoromethylsulfonyl, methoxymethyl, cyano, carboxy, halogen (F, Cl, Br, I), hydroxy, acetylamino, amino, N-phenylamino, N,N-diallylamino, alkoxy, dimethylaminodithiocarbamyl, carboalkoxy, alkylthio, mono- and dialkylamino, N-alkylcarbamyl, N,N-dialkylcarbamyl, alkylsulfoxy, alkylsulfonyl, said alkyl groups containing from 1 to 4 carbon atoms; n is an integer from 0 to 3; and salts thereof.
- 2. A compound as claimed in claim 1 of formula I wherein Y is nitro and n is 1.
- 3. The compound as claimed in claim 2 which is 4-nitro-6-trifluoromethyl-1,3-benzodithiole-2-thione.
- 4. A compound as claimed in claim 1 of formula I wherein Y is trifluoromethyl and n is 1.
- 5. The compound as claimed in claim 4 which is 5-nitro-7-trifluoromethyl-1,3-benzodithiole-2-thione.
- 6. A compound as claimed in claim 1 having formula I wherein Y is trifluoromethyl and n is 2.
- 7. The compound as claimed in claim 6 which is 7-diethylamino-6-nitro-4-trifluoromethyl-1,3-benzodithiole-2-thione.
- 8. The compound as claimed in claim 6 which is 7-dimethylamino-6-nitro-4-trifluoromethyl-1,3-benzodithiole-2-thione.
- 9. A compound as claimed in claim 1 of formula II wherein Y is nitro and n is 1.
- 10. The compound as claimed in claim 9 which is 4-nitro-6-trifluoromethyl-1,3-benzodithiole-2-thione oxide.
- 11. A compound as claimed in claim 1 of formula II wherein Y is CF.sub.3 and n is 2.
- 12. The compound as claimed in claim 11 which is 7-aminopropyl-6-nitro-4-trifluoromethyl-1,3-benzodithiole-2-thione oxide.
- 13. The compound as claimed in claim 11 which is 7-dimethylamino-6-nitro-4-trifluoromethyl-1,3-benzodithiole-2-thione oxide.
- 14. A composition comprising a compound as claimed in claim 1 and an inert diluent therefor.
- 15. A process for preparing compounds of the formula: ##STR8## wherein Y is selected from hydrogen, cyano, alkylsulfonyl, nitro and trifluoromethyl; X is selected from alkyl and alkenyl of up to 6 carbon atoms, nitro, trichloromethyl, trifluoromethyl, trifluoromethoxy, trifluoromethylthio, trifluoromethylsulfoxyl, trifluoromethylsulfonyl, methoxymethyl, cyano, carboxy, carbamyl, halogen (F, Cl, Br, I), hydroxy, acetylamino, amino, N-phenylamino, N,N-diallylamino, alkoxy, dimethylaminodithiocarbamyl, carboalkoxy, alkylthio, mono- and dialkylamino, N-alkylcarbamyl, N,N-dialkylcarbamyl, alkylsulfoxy, alkylsulfonyl, said alkyl groups containing from 1 to 4 carbon atoms and n is an integer from 0 to 3 which comprises reacting a nitrobenzene compound of the formula: ##STR9## wherein Z is halogen (F, Cl, Br, I) or alkoxy, Y, X and n are as defined above;
- with S-tertiarybutyl sodium trithiocarbonate to provide an intermediate, which intermediate is decomposed to provide the desired compound.
- 16. The process of claim 15 wherein said reaction is carried out in a solvent at a temperature in the range from -10.degree. C. to 200.degree. C.
- 17. The process of claim 15 wherein said intermediate is isolated prior to decomposition.
- 18. The process of claim 15 wherein said intermediate is decomposed by heating in a solvent at a temperature in the range from 20.degree. C. to 200.degree. C.
- 19. The process of claim 15 for preparing compounds having formula I wherein Y is nitro and n is 1 which comprises reacting a nitrohalobenzene of formula II wherein Y is nitro and n is 1 with said S-tertiarybutyl sodium trithiocarbonate, decomposing said intermediate and recovering product.
- 20. The process of claim 19 for preparing 4-nitro-6-trifluoromethyl-1,3-benzodithiole-2-thione wherein 2,6-dinitro-4-trifluoromethyl-chlorobenzene is reacted with S-tertiarybutyl sodium trithiocarbonate.
- 21. The process of claim 15 for preparing compounds having formula I wherein Y is CF.sub.3 and n is 1 which comprises reacting a nitrohalobenzene of formula II wherein Y is CF.sub.3 and n is 2 with said S-tertiarybutyl sodium trithiocarbonate, decomposing said intermediate and recovering product.
- 22. The process of claim 21 for preparing 5-nitro-7-trifluoromethyl-1,3-benzodithiole-2-thione wherein 2,4-dinitro-6-trifluoromethyl-chlorobenzene is reacted with S-tertiarybutyl sodium trithiocarbonate.
- 23. The process of claim 15 for preparing compounds having formula I wherein Y is trifluoromethyl and n is 2 which comprises reacting a nitrobenzene of formula II wherein Y is trifluoromethyl and n is 2 with said S-tertiarybutyl sodium trithiocarbonate and recovering product.
- 24. The process of claim 23 for preparing 7-diethylamino-6-nitro-4-trifluoromethyl-1,3-benzodithiole-2-thione wherein 2,4-dinitro-3-diethylamino-6-trifluoromethylchlorobenzene is reacted with said S-tertiarybutyl sodium trithiocarbonate.
- 25. The process of claim 23 for preparing 7-dimethylamino-6-nitro-4-trifluoromethyl-1,3-benzodithiole-2-thione wherein 2,4-dinitro-3-dimethylamino-6-trifluoromethyl-chlorobenzene is reacted with said S-tertiarybutyl sodium trithiocarbonate.
- 26. A process for preparing compounds of the formula: ##STR10## wherein Y is selected from hydrogen, cyano, alkylsulfonyl, nitro and trifluoromethyl; X is selected from alkyl and alkenyl of up to 6 carbon atoms, nitro, trichloromethyl, trifluoromethyl, trifluoromethoxy, trifluoromethylthio, trifluoromethylsulfoxyl, trifluoromethylsulfonyl, methoxymethyl, cyano, carboxy, carbamyl, halogen (F, Cl, Br, I), hydroxy, acetylamino, amino, N-phenylamino, N,N-diallylamino, alkoxy, dimethylaminodithiocarbamyl, carboalkoxy, alkylthio, mono- and dialkylamino, N-alkylcarbamyl, N,N-dialkylcarbamyl, alkylsulfoxy, alkylsulfonyl, said alkyl groups containing from 1 to 4 carbon atoms and n is an integer from 0 to 3 which comprises subjecting a compound of the formula: ##STR11## wherein Y, X and n are as defined above to peroxidation conditions.
- 27. A method of treating pests associated with growing plants selected from fungi, insects and mites to beneficially enhance the growth and/or yield-potential of said growing plants which comprises treating soil, seed or said plants with a biocidally active amount of a compound selected from the group consisting of those of the formulae: ##STR12## wherein Y is selected from hydrogen, cyano, alkylsulfonyl, nitro and trifluoromethyl; X is selected from alkyl and alkenyl of up to 6 carbon atoms, nitro, trichloromethyl, trifluoromethyl, trifluoromethoxy, trifluoromethylthio, trifluoromethylsulfoxyl, trifluoromethylsulfonyl, methoxymethyl, cyano, carboxy, carbamyl, halogen (F, Cl, Br, I), hydroxy, acetylamino, amino, N-phenylamino, N,N-diallylamino, alkoxy, dimethylaminodithiocarbamyl, carboalkoxy, alkylthio, mono- and dialkylamino, N-alkylcarbamyl, N,N-dialkylcarbamyl, alkylsulfoxy, alkylsulfonyl, said alkyl groups containing from 1 to 4 carbon atoms; n is an integer from 0 to 3; and salts thereof.
- 28. The method as claimed in claim 27 wherein said compound has formula I as shown in claim 27 in which Y is nitro and n is 1.
- 29. The method as claimed in claim 28 in which the compound is 4-nitro-6-trifluoromethyl-1,3-benzodithiole-2-thione.
- 30. The method as claimed in claim 27 wherein said compound has formula I as shown in claim 27 in which Y is CF.sub.3 and n is 1.
- 31. The method as claimed in claim 30 in which the compound is 5-nitro-7-trifluoromethyl-1,3-benzodithiole-2-thione.
- 32. The method as claimed in claim 27 wherein said compound has formula I as shown in claim 27 in which Y is trifluoromethyl and n is 2.
- 33. The method as claimed in claim 32 in which the compound is 7-diethylamino-6-nitro-4-trifluoromethyl-1,3-benzodithiole-2-thione.
- 34. The method as claimed in claim 32 in which the compound is 7-dimethylamino-6-nitro-4-trifluoromethyl-1,3-benzodithiole-2-thione.
- 35. The method as claimed in claim 27 wherein said compound has formula II in which Y is nitro and n is 1.
- 36. The method as claimed in claim 35 in which the compound is 4-nitro-6-trifluoromethyl-1,3-benzodithiole-2-thione oxide.
- 37. The method as claimed in claim 27 wherein said compound has formula II in which Y is CF.sub.3 and n is 2.
- 38. The method as claimed in claim 37 in which the compound is 7-aminopropyl-6-nitro-4-trifluoromethyl-1,3-benzodithiole-2-thione oxide.
- 39. The method as claimed in claim 37 in which the compound is 7-dimethylamino-6-nitro-4-trifluoromethyl-1,3-benzodithiole-2-thione oxide.
- 40. The method of claim 27 wherein said compound is combined with an inert diluent.
CROSS-REFERENCE TO RELATED APPLICATIONS
This application is a continuation-in-part of Ser. No. 618,255, filed Sept. 30, 1975, now U.S. Pat. No. 4,139,362 granted Feb. 13, 1979.
US Referenced Citations (3)
Foreign Referenced Citations (1)
Number |
Date |
Country |
823251 |
Nov 1959 |
GBX |
Non-Patent Literature Citations (4)
Entry |
Hurley et al., J. Chem. Soc., 1926, pp. 1821 to 1828. |
Breslow et al., Multi-Sulfur and Sulfur and Oxygen Five- and Six-Membered Heterocycles, Part 1, pp. 475 and 564, Interscience Publishers, NY (1966). |
Shasha, et al., Nature, vol. 210, #5031, pp. 89-90, Apr. 2, 1966. |
Wizinger, et al., Helv. Chim. Acta 46(6), 2167-2177 (1963). |
Continuation in Parts (1)
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Number |
Date |
Country |
Parent |
618255 |
Sep 1975 |
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