Uracil compound containing carboxylate fragment, preparation method therefor, and herbicidal composition and use thereof
AssigneeJiangsu Flag Chemical Industry Co., Ltd.
InventorsPu Zhang, Kaicheng Yao, Yaojun Wu, Dan Xu, Pin Qian, Long Bu, Congqiang Bai
Life of this patent
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Abstract
A uracil compound containing a carboxylate fragment, a preparation method therefor, and a herbicidal composition and use thereof are provided. The preparation method includes a contact reaction between a carboxylic acid compound and different substituted alcohol, halogenated, or sulfonate compound in a presence of a solvent. The uracil compound containing a carboxylate fragment provided by the present invention has better herbicidal activity compared with the prior art.
Claims16
A uracil compound containing a carboxylate fragment, a structure of the uracil compound containing the carboxylate fragment is shown hi a formula (I):
- in the formula (I):
- R1 and R2 are each selected from hydrogen or methyl;
- or the R1, the R2, and a carbon atom attached to the R1 and the R2 form a 3-membered carbocycle;
- R3 is selected from C1-3 alkoxy C1-3 alkyl, C1-3 haloalkoxy C1-3 alkyl, C2-6 alkenoxy C1-3 alkyl, C2-6 haloalkenoxy C1-3 alkyl, C2-6 alkynoxy C1-3 alkyl, C2-6 haloalkynoxy C1-3 alkyl, C1-3 alkyl S(O)n C1-3 alkyl, C3-6 oxygen-containing cycloalkyl C1-3 alkyl, or C3-9 oxygen-containing cycloalkyl;
- n=0, 1, or 2;
- and
- when the R1 is hydrogen and the R2 is methyl, a chiral carbon atom connected to the R1 and the R2 is selected from either an R configuration or an S configuration, or a mixture of the R configuration and the S configuration;
- and in the mixture, a ratio of the R configuration to the S configuration is 1:99 to 99:1.
A method for preparing a uracil compound containing a carboxylate fragment, a structure of the uracil compound containing the carboxylate fragment is shown in a formula (I):
- wherein the method comprises a contact reaction between a carboxylic acid compound shown in a formula (II) and different substituted alcohol, halogenated, or sulfonate compounds in a presence of a solvent,
- wherein in the general formulas (I) and (II):
- R1 and R2 are each selected from hydrogen or methyl;
- or the R1, the R2, and a carbon atom attached to the R1 and the R2 form a 3-membered carbocycle;
- R3 is selected from C1-3 alkoxy C1-3 alkyl, C1-3 haloalkoxy C1-3 alkyl, C2-6 alkenoxy C1-3 alkyl, C2-6 haloalkenoxy C1-3 alkyl, C2-6 alkynoxy C1-3 alkyl, C2-6 haloalkynoxy C1-3 alkyl, C1-3 alkyl S(O)n C1-3 alkyl, C3-6 oxygen-containing cycloalkyl C1-3 alkyl, or C3-9 oxygen-containing cycloalkyl;
- n=0, 1, or 2;
- and
- when the R1 is hydrogen and the R2 is methyl, a chiral carbon atom connected to the R1 and the R2 is selected from either an R configuration or an S configuration, or a mixture of the R configuration and the S configuration;
- and in the mixture, a ratio of the R configuration to the S configuration is 1:99 to 99:1.
A method of using a uracil compound containing a carboxylate fragment, a structure of the uracil compound containing the carboxylate fragment is shown in formula (I):
- in the formula (I):
- R1 and R2 are each selected from hydrogen or methyl;
- or the R1 the R2, and a carbon atom attached to the R1 and the R2 form a 3-membered carbocycle;
- R3 is selected from C1-3 alkoxy C1-3 alkyl, C1-3 haloalkoxy C1-3 alkyl, C2-6 alkenoxy C1-3 alkyl, C2-6 haloalkenoxy C1-3 alkyl, C2-6 alkenoxy C1-3 alkyl, C2-6 haloalkynoxy C1-3 alkyl, C1-3 alkyl S(O)n C1-3 alkyl, C3-6 oxygen-containing cycloalkyl C1-3 alkyl, or C3-9 oxygen-containing cycloalkyl;
- n=0, 1, or 2;
- and
- when the R1 is hydrogen and the R2 is methyl, a chiral carbon atom connected to the R1 and the R2 is selected from either an R configuration or an S configuration, or a mixture of the R configuration and the S configuration;
- and in the mixture, a ratio of the R configuration to the S configuration is 1:99 to 99:1 in prevention and control of weeds, comprising a step of:
- treating seeds pre-emergence with the uracil compound or treating plants post-emergence with the uracil compound.
Dependencies are inferred from the claim text.