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Usage

Uses

Used in Agriculture:
DINOBUTON is used as a fungicide for the control of powdery mildews in various crops. It is particularly effective in protecting apples, cotton, and vegetables from fungal infections, ensuring a healthy and bountiful harvest.
Used in Apple Production:
DINOBUTON is used as a protective agent in apple production, targeting powdery mildews that can cause significant damage to the fruit and reduce crop yields. By applying DINOBUTON, farmers can effectively manage these fungal infections and maintain the quality and quantity of their apple harvest.
Used in Cotton Production:
In the cotton industry, DINOBUTON serves as a crucial fungicide to combat powdery mildews that can negatively impact the growth and quality of cotton plants. Its application helps in safeguarding the cotton crop from diseases, leading to improved fiber production and overall crop health.
Used in Vegetable Production:
DINOBUTON is also utilized in vegetable production to protect plants from powdery mildews that can affect their growth and yield. By incorporating DINOBUTON into their disease management strategies, farmers can ensure a healthy and productive vegetable crop, contributing to a stable food supply.

Metabolic pathway

Dinobuton is metabolised in plants and animals via common metabolic pathways. The primary reaction is hydrolytic cleavage of the carbonate-dinitrophenyl linkage to yield dinoseb. Further reduction of the nitro-groups of dinoseb yields the corresponding monoamino and diamino analogues. Acetylation and deamination via hydroxylation/ elimination, and oxidation of the sec-butyl moiety also occurred. N- and O-Conjugation as glucosides and glucuronides occurred in both plants and animals. The metabolic pathways of dinobuton are presented in Scheme 1.

Degradation

There is limited information on the hydrolytic stability of dinobuton (1). Marchenko and Vakulenko (1983) reported that the hydrolysis DT50 values of dinobuton in pH 2, 7 and 11 buffer solutions at 22 °C were 15 days, 17 days and 4 hours, respectively. In vitro studies showed the rapid hydrolysis of dinobuton to dinoseb [ 2-sec-butyl-4,6-dinitrophenol (2)] by tissue homogenates of spider mites and animal tissues. Once generated, dinoseb was stable to hydrolytic and photolytic degradation under acidic condition but was readily degraded under alkaline conditions (Brestkin et al., 1978; Molnar, 1935). Uncharacterised complex polar materials were reported as photodecomposition products of dinoseb (Matsuo and Casida, 1970). Grechko et al. (1986) reported that the DTW for dinobuton in aqueous solution under UV light irradiation (365 nm) was <30 min.

InChI:InChI=1/C27H38N4O11/c1-9-17(7)21-11-19(28(33)34)13-23(30(37)38)26(21,15(3)4)41-25(32)42-27(16(5)6)22(18(8)10-2)12-20(29(35)36)14-24(27)31(39)40/h11-18,21-22H,9-10H2,1-8H3

Relevant academic research and scientific papers

Diaryl derivatives and their use as crop protection agents

Diaryl derivatives of the general formula I STR1 where A is =CHOR1, =CHSR1, =CHR1, =CHCl or =NOR1, B is OR2, SR2 or NR2 R3 and Het is a mono-, di- or trinuclear aromatic five- or six-membered heterocyclic structure which is unsubstituted or substituted by R, R1, R2, R3, R4, R5 are identical or different and each is hydrogen or alkyl, and U, V, W are identical or different and each is halogen, alkyl or alkoxy, and fungicides containing these compounds.

β-substituted cinnamic acid derivative

β-Substituted cinnamic acid derivatives of the formula 1, STR1 where R1 is substituted or unsubstituted alkyl, alkenyl, alkynyl, cycloalkyl or cycloalkenyl, and R1 can also be chlorine or bromine, --X-- is --O--, --S--, STR2 m is 0 or 1, --Y is --OR4, --O--N=CR5 R6, --NR7 R8, --NR7 R8, --N(OR9)R10 or SR11, where the abovementioned substitutes R2 to R11 are substituted or unsubstituted alkyl, alkenyl, alkynyl, cycloalkyl or cycloalkenyl, and R2, R3 and R5 to R11 can be hydrogen and Z, U, V, W are defined in the specification.

α-arylacrylic acid derivatives, their preparation and use for controlling pests and fungi

α-Arylacrylic acid derivatives of the formula I STR1 where the substituents have the following meanings: X C, N Y CR4, N, O, S Z CR5, N, O, S n 0 to 4 R1 hydrogen, nitro, cyano, halogen; alkyl, alkoxy, halogenated alkyl, halogenated alkoxy or alkylthio, or, when n is 2, 3 or 4, two adjacent substituents R1 may together denote a 1,3-butadien-1,4-diyl group which may be substituted; R2 alkyl; halogenated alkyl, halogen, cyano, nitro, alkoxycarbonyl, dimethylamino, R2 additionally denotes hydrogen; R3 hydrogen; substituted or unsubstituted alkyl; a substituted or unsubstituted cyclic structure, which may contain, in addition to carbon atoms, one to three heteroatoms; or a substituted or unsubstituted aromatic system, which may contain, in addition to carbon atoms, one to four nitrogen atoms and one to three heteroatoms; R4, R5 hydogen, alkyl; halogenated alKyl, halogen, cyano, nitro, dimethylamino, alkoxycarbonyl and pesticides and fungicidal agents containing these compounds.

Anilide derivatives and their use for combating botrytis

The use of nicotinic anilide derivatives of the general formula STR1 where the substituents have the following meanings: R1 halogen, methyl, trifluoromethyl, methoxy, methylthio, methylsulfinyl, methylsulfonyl R2 unsubstituted or halogen-substituted alkyl, unsubsituted or halogen-substituted alkenyl, alkynyl, unsubstituted or halogen-substituted alkoxy, unsubstituted or halogen-substituted alkenyloxy, alkynyloxy, cycloalkyl, cycloalkenyl, cycloalkyloxy, cycloalkenloxy for combating Botrytis, and nicotinic anilides of the formula I.

α-Hydroxyazolylethyloxiranes and fungicides containing these compounds

α-Hydroxyazolylethyloxiranes of the general formula I STR1 where R1 and R2 are each alkyl, cycloalkyl, cycloalkenyl, phenyl, biphenyl, naphthyl or pyridyl, these radicals being unsubstituted or substituted, and X is CH or N, their plant-tolerated acid addition salts and metal complexes, and fungicides containing these compounds.

Unsaturated cyclohexylacetic acid derivatives, and crop-protection agents containing same

Unsaturated cyclohexylacetic acid derivatives of the formula I STR1 where U is=NOCH3, =CHOCH3, =CH2, =CH--CH3, =CH--CH2 --CH3, =N--NH--CH3 or =CH--S--CH3, n is from 0 to 10, A is hydrogen or substituted or unsubstituted alkyl, cycloalkyl, aryl or hetaryl, and X is a single bond when n is 0, and oxygen, sulfur or a single bond when n is not 0, and the plant-compatible acid addition products and base addition products thereof, and fungicides and insecticides containing these compounds.

Sulfur-containing oxime ethers and fungicides containing them

Oxime ether derivatives of the formula STR1 where R1 and R2 are each hydrogen or alkyl, X is S, SO or SO2, R3 is hydrogen, cycloalkyl, phenyl, naphthyl, quinolinyl or phenanthrenyl, these radicals being unsubstituted or substituted, Y is alkylene, alkenylene or alkynylene, and m is 0 or 1.

Phenylalkylamines and fungicides containing these

Phenylalkylamines of the formula STR1 where n is 5, 6, 7, 8 or 9, m is 1, 2 or 3, R1 is methyl, halogen, substituted or unsubstituted aryl or substituted or unsubstituted phenoxy, and, when m is 2, two adjacent radicals R1 together denote the radical STR2 X is oxygen, except when R1 is methyl, or the radical STR3 R4 is isopropyl, tert-butyl or substituted or unsubstituted phenyl and R5 is H or OH, R2 and R3 are each hydrogen and, when X is oxygen, R2 and R3 additionally denote methyl or ethyl, and their plant-tolerated salts, and fungicides containing these compounds.

Sulfur-containing acrylic esters and fungicides containing them

Acrylic esters of the formula STR1 where R1 and R2 are hydrogen or alkyl, X is S, SO or SO2, R3 is phenyl, naphthyl or phenanthrenyl, these radicals being unsubstituted or substituted, with the exception of compounds in which R3 is phenyl, 3-chlorophenyl, 4-chlorophenyl, 2,4-dichlorophenyl or methylphenyl, and fungicides containing these compounds.

Azolylmethyloxiranes and fungicides containing them

Azolylmethyloxiranes of the general formula I STR1 where R1, R2 and R3 are substituted or unsubstituted alkyl, benzyl, naphthyl, biphenyl, dioxanyl, phenyl, tetrahydropyranyl, tetrahydrofuranyl, norbornyl, C3 -C12 -cycloalkyl or C3 -C12 -cycloalkenyl, and X is CH or N, and plant-tolerated acid addition salts and metal complexes thereof, and fungicides containing these compounds.