Synthesis Of Hydrazonyl Acid And Chloroacetic Acid Derivatives And Their Plant Growth Activity

Weeds gave a huge crop losses annually in agricultural production.Chemical weed control approach has been first choice for modern agriculture.The efficient, safe, low toxicity, highly selective herbicide is a hot research topic in today’s research and development of new pesticides.Substructure splicing activity is the development of new pesticides used in the more widely methods. Based on the pesticide active principle splicing design of molecular substructure, This article will have herbicidal activity groups, such as: Schiff base, an amide(oxime ester) group, chlorine, hydrophobic aliphatic hydrocarbon, aromatic hydrocarbon group, and other active sub-structure splicing.I design and synthesis of new compounds for plant growth activity test to try to find the herbicidal activity of the new structure of the lead compound.The main work is as follows:1、In acid, aliphatic or aromatic aldehydes and ketones, hydroxylamine, hydrazine hydrate as the raw material,After hydrazone, oxime intermediates and other steps designed and synthesized chlorine acetylhydrazone(I), chloroacetyl oxime ester(II) and benzophenonehydrazone acetyl benzaldehyde hydrazone(III) three categories total 26 new compounds.Various types of compound of the formula as follows:2 、 Structural characterization of some compounds by FT-IR and 1H NMR instrumentation and characterization methods, and combined with classical test methods and the comprehensive analysis proves synthesis work to achieve the desired objectives.3 、 We discuss the influence of various factors synthesis reaction synthesis intermediate hydrazone and oxime direct reaction at room temperature(to about 50% of aldehydes and ketones) yields dropped below the reflux reaction conditions(in terms of aldehydes and ketones most of the yield above 70%).Acetylhydrazone chlorine and acid oxime ester compound synthesis with acid binding agent, choose a lower yield of inorganic bases(intermediate count about 35%), while the use of organic base pyridine yields increased significantly(intermediate total yield most in more than 60%).4、In monocots Rice, Sorghum and dicots rape, amaranth for the target crop, the new compounds were tested for plant growth activity.Test results show that the compounds I root length of four test plants have relatively significantly inhibited, some of the compounds at 12.5 mg / L concentration will be exhibited strong inhibition, 200 mg / L when the inhibitory effect was significant(for example, compounds I at different concentrations monocots rice root growth inhibition rate in the range of 31.62% ~ 115.46%,and on the growth of cole root growth inhibition rate range is 105.77% ~ 156.96% at 12.5mg/L~200mg/L).The overall trend of root inhibition at low concentrations facilitate high concentration inhibition and plant stem length inhibitory effect is not obvious.Compound II for plant roots while showing inhibition(Compound 5e for monocots rice root growth inhibition rate in the range of 31.14% ~ 97.75%, its stem growth inhibition rate in the range of 18.99%- 95.72% at 12.5mg/L~200mg/L). Its inhibition are more obvious.Some compounds of the root and stem growth inhibition exhibited low concentration to promote growth, high concentrations inhibit the growth of the plants.Compound III inhibition rate dicots to monocots superior inhibition(the root growth inhibition rate range for monocots rice was 20.96% ~ 90.38%, for the root growth of cole inhibition rate in the range of 108.66% ~ 130.71 % at 12.5 mg/L~200 mg/L) for the inhibitory effect of the roots of plants is not obvious.A substituent on the phenyl ring and various substituents different positions have a greater impact on its herbicidal activity. For chloroacetyl benzaldehyde compound,3,4-substituted phenyl group(a hydroxyl group, a nitro group) containing, for monocots and dicots roots showed strong inhibitory effect, While the inhibition rate when monocots in to dicots inhibition rate, the second position substituent is a nitro bit of chlorine when the root inhibition rate dicots than inhibition of monocots rate, for chloroacetyl acetophenone, when making use of bits methoxy not obvious; the time base for the inhibition of root two plants is very obvious, when the registration is nitro when monocots root inhibition rate higher than for dicots inhibition rate.Several compounds for both plant stems inhibition rate is not obvious. For chloroacetophenone oxime ester compounds, when the 3rd bit of chlorine to the roots of two plants showed strong inhibition. For benzophenonehydrazone acetyl benzaldehyde hydrazone, for both plants and inhibited, and the inhibitory effect of dicots to monocots superior inhibitory effect.