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US 2017/0280721 A1Published application
1,2,3-thiadiazol-5yl-urea derivatives, use thereof for regulating plant senescence and preparations containing these derivatives
AssigneeUstav Experimentalni Botaniky Av Cr, V.V.I.
InventorsJaroslav NISLER, Marek ZATLOUKAL, Lukas SPICHAL, Radoslav KOPRNA, Karel DOLEZAL, Miroslav STRNAD
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Abstract
Substituted 1,2,3-thiadiazol-5yl-urea derivatives, their use as anti-senescence and anti-stress factors of plant cells, organs and the whole plant, and preparations containing these derivatives.
Claims8
1:
- A method of inhibiting stress and/or senescence and/or oxidative damage in plants, plant organs and/or plant cells, and/or for increasing the yield of plants, without side effect of root growth inhibition, comprising of applying the compound comprising 1,2,3-thiadiazol-5-yl-urea derivatives of the general formula (I),
- wherein
- R1 is selected from the group consisting of
- C1-C6 alkyl, substituted with at least one moiety selected from hydroxy, C1-C4 alkoxy, thio, C1-C4 alkylthio, cyano and halogen;
- C2-C6 alkenyl, optionally substituted with at least one moiety selected from hydroxy, C1-C4 alkoxy, thio, C1-C4 alkylthio, cyano and halogen;
- C2-C6 alkynyl, optionally substituted with at least one moiety selected from hydroxy, C1-C4 alkoxy, thio, C1-C4 alkylthio, cyano and halogen;
- tetrahydro-furan-2-yl-methyl or tetrahydro-furan-3-yl-methyl, optionally substituted with at least one moiety selected from hydroxy, C1-C4 alkyl, C1-C4 alkoxy, thio, C1-C4 alkylthio, cyano and halogen;
- thiophen-2-yl-methyl or thiophen-3-yl-methyl optionally substituted with at least one moiety selected from hydroxy, C1-C4 alkyl, C1-C4 alkoxy, thio, C1-C4 alkylthio, cyano and halogen;
- furan-2-yl-methyl or furan-3-yl-methyl, optionally substituted with at least one moiety selected from hydroxy, C1-C4 alkyl, C1-C4 alkoxy, thio, C1-C4 alkylthio, cyano and halogen;
- 1,3-dioxolan-2-yl-methyl, optionally substituted with at least one moiety selected from hydroxy, C1-C4 alkyl, C1-C4 alkoxy, thio, C1-C4 alkylthio, cyano and halogen;
- tetra hydropyran-2-ylmethyl, tetra hydropyran-3-ylmethyl or tetra hydropyran-4-ylmethyl, optionally substituted with at least one moiety selected from hydroxy, C1-C4 alkyl, C1-C4 alkoxy, thio, C1-C4 alkylthio, cyano and halogen;
- (3,4-dihydro-2H-pyran-2-yl)methyl, (3,4-dihydro-2H-pyran-3-yl)methyl, (3,4-dihydro-2H-pyran-4-yl)methyl, (3,4-dihydro-2H-pyran-5-yl)methyl or (3,4-dihydro-2H-pyran-6-yl)methyl, optionally substituted with at least one moiety selected from hydroxy, C1-C4 alkyl, C1-C4 alkoxy, thio, C1-C4 alkylthio, cyano and halogen.
9 more elements
2:
- 1,2,3-thiadiazol-5-yl-urea derivatives of the general formula (Ia),
- wherein
- R1a is selected from the group consisting of
- C1-C6 alkyl, substituted with at least one moiety selected from hydroxy, C1-C4 alkoxy, thio, C1-C4 alkylthio, cyano and halogen;
- C2-C6 alkenyl, optionally substituted with moiety selected from hydroxy, C1-C4 alkoxy, thio, C1-C4 alkylthio, cyano and halogen;
- C2-C6 alkynyl, optionally substituted moiety selected from hydroxy, C1-C4 alkoxy, thio, C1-C4 alkylthio, cyano and halogen;
- tetrahydro-furan-2-yl-methyl or tetrahydro-furan-3-yl-methyl, optionally substituted with at least one moiety selected from hydroxy, C1-C4 alkyl, C1-C4 alkoxy, thio, C1-C4 alkylthio, cyano and halogen;
- thiophen-2-yl-methyl or thiophen-3-yl-methyl optionally substituted with at least one moiety selected from hydroxy, C1-C4 alkyl, C1-C4 alkoxy, thio, C1-C4 alkylthio, cyano and halogen;
- furan-2-yl-methyl or furan-3-yl-methyl, substituted with at least one moiety selected from hydroxy, C1-C4 alkyl, C1-C4 alkoxy, thio, C1-C4 alkylthio, cyano and halogen;
- 1,3-dioxolan-2-yl-methyl, optionally substituted with at least one moiety selected from hydroxy, C1-C4 alkyl, C1-C4 alkoxy, thio, C1-C4 alkylthio, cyano and halogen;
- tetra hydropyran-2-ylmethyl, tetra hydropyran-3-ylmethyl or tetra hydropyran-4-ylmethyl, optionally substituted with at least one moiety selected from hydroxy, C1-C4 alkyl, C1-C4 alkoxy, thio, C1-C4 alkylthio, cyano and halogen;
- (3,4-dihydro-2H-pyran-2-yl)methyl, (3,4-dihydro-2H-pyran-3-yl)methyl, (3,4-dihydro-2H-pyran-4-yl)methyl, (3,4-dihydro-2H-pyran-5-yl)methyl or (3,4-dihydro-2H-pyran-6-yl)methyl, optionally substituted with at least one moiety selected from hydroxy, C1-C4 alkyl, C1-C4 alkoxy, thio, C1-C4 alkylthio, cyano and halogen.
9 more elements
3:
- The method according to claim 1, wherein R1 is furan-2-yl-methyl or furan-3-yl-methyl or 2-methoxyethyl.
4:
- The method according to claim 1, wherein said method includes delaying chlorophyll degradation and/or senescence of plant tissues and/or inhibition of membrane lipid peroxidation, which further increases their anti-senescence and anti-stress activity.
5:
- The method according to claim 1, wherein said use includes inhibition of stress and stress-induced senescence in the production of crops and wherein the stress is a stress caused by dryness and/or heat or cold and/or salinity.
6:
- Antisenescent and/or antistress preparations for plants, plant organs and plant cells, according to claim 2 further comprising at least one compound of the general formula (Ia) and at least one auxiliary substance.
7:
- The method of claim 1 of inhibiting stress and/or senescence and/or oxidative damage in plants, plant organs and/or plant cells, and/or for increasing the yield of plants, without the side effect of root growth inhibition, comprising the step of applying at least one compound of the general formula (I) onto said plant, plant organ and/or plant cell.
8:
- The method of preparation of the compounds of general formula (I) according to claim 1, wherein 1,2,3-thiadiazol-5-ylisocyanate is prepared from 1,2,3-thiadiazol-5-ylamine and diphosgene, and then further reacted with a corresponding amine of formula R1NH2, wherein R1 is as defined in claim 1.