芳酰基硫脲类化合物的合成、晶体结构及杀虫活性研究
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摘要
20世纪60年代末Schroepl E等合成了CH_3(CH_2)_nCOHNCSNHR~1，生物活性测试显示，此类化合物具有良好的杀虫活性。此后，人们通过对硫脲桥两端取代基的修饰，合成了大量的芳酰基硫脲类化合物，通过生物活性测定，发现此类化合物具有广泛的生物活性。近年来，具有植物生长调节活性、除草活性和抑菌活性的酰基硫脲类化合物合成较多。为了寻求具有生物活性的化合物，我们设计合成了两个系列的化合物，进行了杀虫活性测定，解析了部分化合物的单晶结构，为进一步研究该类化合物的结构和生物活性的关系提供了依据。
本论文共分两个部分：
第一部分：2，4-二氯苯氧乙酰基硫脲类化合物的合成、晶体结构及杀虫活性研究。
以2，4-二氯苯氧乙酸为原料，经过氯化生成2，4-二氯苯氧乙酰氯，然后与硫氰化钠反应生成2，4-二氯苯氧乙酰基异硫氰酸酯，最后与取代芳胺反应，得到6个2，4-二氯苯氧乙酰基硫脲化合物，并用紫外光谱、红外光谱和氢核磁共振谱确认了结构。对目标化合物进行了单晶培养，得到了3个单晶数据即晶体Ⅰb，Ⅰe和Ⅰf。3个晶体中S=C双键的键长在1.626-1.645(?)之间；O=C双键的键长在1.204-1.221(?)之间；N-C键长在1.330-1.425(?)之间，说明N-C键具有N=C双键的特征。3个分子中均有两个N-H…O分子内氢键，分别形成了毗邻的五元环和六元环结构。中间酰基脲桥部分中的C9-N1-C8就如一个离域共轭结构，羰基氧原子与羰基硫原子呈反式排列在这个共轭结构的两端。采用浸叶法对化合物(Ⅰa-Ⅰf)进行了初步杀虫活性筛选，结果表明化合物Ⅰe的杀虫活性较好，毒力测定表明，化合物Ⅰe对小菜蛾3龄幼虫的LC_(50)为305.80mg／L。
第二部分：芳甲酰基硫脲类化合物的合成、晶体结构及杀虫活性研究。
以苯甲酸、邻甲基苯甲酸和2-呋喃甲酸为原料，经过氯化生成相应的芳酰氯，然后与硫氰化钠反应生成相应的芳酰基异硫氰酸酯，最后与取代芳胺反应，得到12个芳酰基硫脲化合物，并用紫外光谱、红外光谱和氢核磁共振谱确认了结构。对液相合成法和相转移催化法的优劣做了简单的比较和分析。对12个目标化合物进行了单晶培养，得到了化合物Ⅱc，Ⅱe，Ⅱg和Ⅱh的单晶数据，其中化合物Ⅱc在DMF中培养出的单晶发生了结构变化，转变为2-苯甲酰胺-4，6-二氯苯并噻唑，推测其变化机制为自身基团间的亲核取代反应。晶体Ⅱc和Ⅱg的每一个晶胞单元中都包括两个相对独立的分子(Molecule A and Molecule B)，这两个相对独立的分子所对应的键长和键角差别不大，但是所对应的二面角的差异却很大，该差异可能是由苯环与中间酰基硫脲基团相连接的C-C键自由旋转程度不同造成的。晶体Ⅱe中分子间氢键N-H…S把分子连接成了链状结构，并形成了R_2~2(8)的环状结构。晶体Ⅱh中分子间氢键N-H…O和N-H…S把分子连接成了丝带状结构，并分别形成了R_2~2(12)和R_2~2(8)的环状结构。采用浸叶法对化合物(Ⅱa-Ⅱh)进行了初步杀虫活性筛选，结果表明化合物Ⅱb和Ⅱc具有一定的杀虫活性。进一步的室内毒力测定表明，化合物Ⅱb和Ⅱc对小菜蛾3龄幼虫的LC_(50)分别为144.61mg／L和109.55mg／L。
In the end of 1960s, the compounds CH_3(CH_2)_nCOHNCSNHR~1, whichexhibited good pesticidal activities through biological activities tests, weresynthesized by Schroepl E. In the later years, a mount of aroylthioureas were preparedby modifying the substituted groups of thiourea, and presented extensive biologicalactivities. During these years, the aeylthioureas, which displayed the activities of plantgrowth regulator, herbicide and fungicide, were synthesized. In order to find morecompounds possessing biological activities, two series aroylthioureas were designedand synthesized, and their pesticidal activities were also tested. Seven single crystalstructures of the compounds were obtained to supply the data for studying therelationship between the structure and biological activities of these compounds.
The thesis includes two parts as follows:
First, study on synthesis, crystal structure and pesticidal activities of2,4-dichlorophenoxyacetylthioureas.
The compound 2,4-dichlorophenoxyacetylisothiocyanate was prepared by thereaction of 2,4-dichlorophenoxyacetylchloride derived from the chlorination of2,4-dichlorophenoxyacetic acid with sodium thiocyanate. Trearnent with the2,4-dichlorophenoxyacetylisothiocyanate with 6 different substituted arylaminesafforded six 2,4-dichlorophenoxyacetylthioureas which were confirmed by UV, IRand ~1H NMR. The single crystals ofⅠb,Ⅰe andⅠf suitable for collecting data onthe X-ray diffraction machine were obtained. In the three single crystal structures, thebond lengths of S=C double bonds are among 1.626-1.645(?), O=C double bonds areamong 1.204-1.221(?) and N-C single bonds are among 1.330-1.425(?), indicating suchN-C single bonds possessing the characteristics of N=C double bond. There are twointramolecular N-H…O hydrogen bonds in each of the three crystal structures,making a five-membered ring edged with a six-membered ring. The C9-N1-C8 grouppart of the central thiourea group is just like a conjugated structure, at the end ofwhich arrange the oxygen atom of carbonyl group and the sulfur atom of thio-carbonyl group adopting the trans-conformation. The pesticidal activity test wascarried on the compounds(Ⅰa-Ⅰf) by dipping method, which showed that thecompoundⅠe exhibited better pesticidal activity with LC_(50) being 305.80mg/L.
Second, study on synthesis, crystal structure and pesticidal activity ofaroylthioureas.
The compounds-aroylisothiocyanates were prepared by the reaction ofaroylchlorides derived from the benzoic acid, o-methylbenzoic acid and 2-furoic acidwith sodium thiocyanate. Treament with the aroylisothiocyanates with differentsubstituted arylamines afforded 12 aroylthioureas which were confirmed by UV, IRand ~1H NMR. The advantages and disadvantages between the method of reaction inliquid and the phase-transfer catalysis method were compared. The single crystals ofⅡc,Ⅱe,Ⅱg andⅡh suitable for collecting data on the X-ray diffraction machinewere obtained. The compoundⅡc changed into the compound2-benzoylamino-4,6-dichlorobenzothiazole when it crystallized from the DMF solvent,and the changing mechanism of this phenomenon was proposed to be nucleophilicsubstitution reaction. The oxygen atom of carbonyl group and the sulfur atom ofthio-carbonyl group adopt the trans-conformation. In the crystalsⅡc andⅡg, thereare two independent molecules (Molecule A and Molecule B) in a unit cell in eachcrystal. There are few differences of bond lengths and bond angles between the twoindependent molecules, but obvious differences of dihedral angles between them,which maybe contributed to free rotation degree of the C-C bond which connects thecentral part and phenyl ring. In the crystalⅡe, the intermolecular N-H…S hydrogenbonds link the molecules into a chain structure and form a R_2~2(8) motif. The pesticidalactivity test was carried on the compounds(Ⅱa-Ⅱh) by dipping method, whichshowed that the compoundsⅡb andⅡc exhibited some pesticidal activity withLC_(50) of the compoundsⅡb andⅡc being 144.61mg/L and 109.55mg/L, respectively.
本论文共分两个部分：
第一部分：2，4-二氯苯氧乙酰基硫脲类化合物的合成、晶体结构及杀虫活性研究。
以2，4-二氯苯氧乙酸为原料，经过氯化生成2，4-二氯苯氧乙酰氯，然后与硫氰化钠反应生成2，4-二氯苯氧乙酰基异硫氰酸酯，最后与取代芳胺反应，得到6个2，4-二氯苯氧乙酰基硫脲化合物，并用紫外光谱、红外光谱和氢核磁共振谱确认了结构。对目标化合物进行了单晶培养，得到了3个单晶数据即晶体Ⅰb，Ⅰe和Ⅰf。3个晶体中S=C双键的键长在1.626-1.645(?)之间；O=C双键的键长在1.204-1.221(?)之间；N-C键长在1.330-1.425(?)之间，说明N-C键具有N=C双键的特征。3个分子中均有两个N-H…O分子内氢键，分别形成了毗邻的五元环和六元环结构。中间酰基脲桥部分中的C9-N1-C8就如一个离域共轭结构，羰基氧原子与羰基硫原子呈反式排列在这个共轭结构的两端。采用浸叶法对化合物(Ⅰa-Ⅰf)进行了初步杀虫活性筛选，结果表明化合物Ⅰe的杀虫活性较好，毒力测定表明，化合物Ⅰe对小菜蛾3龄幼虫的LC_(50)为305.80mg／L。
第二部分：芳甲酰基硫脲类化合物的合成、晶体结构及杀虫活性研究。
以苯甲酸、邻甲基苯甲酸和2-呋喃甲酸为原料，经过氯化生成相应的芳酰氯，然后与硫氰化钠反应生成相应的芳酰基异硫氰酸酯，最后与取代芳胺反应，得到12个芳酰基硫脲化合物，并用紫外光谱、红外光谱和氢核磁共振谱确认了结构。对液相合成法和相转移催化法的优劣做了简单的比较和分析。对12个目标化合物进行了单晶培养，得到了化合物Ⅱc，Ⅱe，Ⅱg和Ⅱh的单晶数据，其中化合物Ⅱc在DMF中培养出的单晶发生了结构变化，转变为2-苯甲酰胺-4，6-二氯苯并噻唑，推测其变化机制为自身基团间的亲核取代反应。晶体Ⅱc和Ⅱg的每一个晶胞单元中都包括两个相对独立的分子(Molecule A and Molecule B)，这两个相对独立的分子所对应的键长和键角差别不大，但是所对应的二面角的差异却很大，该差异可能是由苯环与中间酰基硫脲基团相连接的C-C键自由旋转程度不同造成的。晶体Ⅱe中分子间氢键N-H…S把分子连接成了链状结构，并形成了R_2~2(8)的环状结构。晶体Ⅱh中分子间氢键N-H…O和N-H…S把分子连接成了丝带状结构，并分别形成了R_2~2(12)和R_2~2(8)的环状结构。采用浸叶法对化合物(Ⅱa-Ⅱh)进行了初步杀虫活性筛选，结果表明化合物Ⅱb和Ⅱc具有一定的杀虫活性。进一步的室内毒力测定表明，化合物Ⅱb和Ⅱc对小菜蛾3龄幼虫的LC_(50)分别为144.61mg／L和109.55mg／L。
In the end of 1960s, the compounds CH_3(CH_2)_nCOHNCSNHR~1, whichexhibited good pesticidal activities through biological activities tests, weresynthesized by Schroepl E. In the later years, a mount of aroylthioureas were preparedby modifying the substituted groups of thiourea, and presented extensive biologicalactivities. During these years, the aeylthioureas, which displayed the activities of plantgrowth regulator, herbicide and fungicide, were synthesized. In order to find morecompounds possessing biological activities, two series aroylthioureas were designedand synthesized, and their pesticidal activities were also tested. Seven single crystalstructures of the compounds were obtained to supply the data for studying therelationship between the structure and biological activities of these compounds.
The thesis includes two parts as follows:
First, study on synthesis, crystal structure and pesticidal activities of2,4-dichlorophenoxyacetylthioureas.
The compound 2,4-dichlorophenoxyacetylisothiocyanate was prepared by thereaction of 2,4-dichlorophenoxyacetylchloride derived from the chlorination of2,4-dichlorophenoxyacetic acid with sodium thiocyanate. Trearnent with the2,4-dichlorophenoxyacetylisothiocyanate with 6 different substituted arylaminesafforded six 2,4-dichlorophenoxyacetylthioureas which were confirmed by UV, IRand ~1H NMR. The single crystals ofⅠb,Ⅰe andⅠf suitable for collecting data onthe X-ray diffraction machine were obtained. In the three single crystal structures, thebond lengths of S=C double bonds are among 1.626-1.645(?), O=C double bonds areamong 1.204-1.221(?) and N-C single bonds are among 1.330-1.425(?), indicating suchN-C single bonds possessing the characteristics of N=C double bond. There are twointramolecular N-H…O hydrogen bonds in each of the three crystal structures,making a five-membered ring edged with a six-membered ring. The C9-N1-C8 grouppart of the central thiourea group is just like a conjugated structure, at the end ofwhich arrange the oxygen atom of carbonyl group and the sulfur atom of thio-carbonyl group adopting the trans-conformation. The pesticidal activity test wascarried on the compounds(Ⅰa-Ⅰf) by dipping method, which showed that thecompoundⅠe exhibited better pesticidal activity with LC_(50) being 305.80mg/L.
Second, study on synthesis, crystal structure and pesticidal activity ofaroylthioureas.
The compounds-aroylisothiocyanates were prepared by the reaction ofaroylchlorides derived from the benzoic acid, o-methylbenzoic acid and 2-furoic acidwith sodium thiocyanate. Treament with the aroylisothiocyanates with differentsubstituted arylamines afforded 12 aroylthioureas which were confirmed by UV, IRand ~1H NMR. The advantages and disadvantages between the method of reaction inliquid and the phase-transfer catalysis method were compared. The single crystals ofⅡc,Ⅱe,Ⅱg andⅡh suitable for collecting data on the X-ray diffraction machinewere obtained. The compoundⅡc changed into the compound2-benzoylamino-4,6-dichlorobenzothiazole when it crystallized from the DMF solvent,and the changing mechanism of this phenomenon was proposed to be nucleophilicsubstitution reaction. The oxygen atom of carbonyl group and the sulfur atom ofthio-carbonyl group adopt the trans-conformation. In the crystalsⅡc andⅡg, thereare two independent molecules (Molecule A and Molecule B) in a unit cell in eachcrystal. There are few differences of bond lengths and bond angles between the twoindependent molecules, but obvious differences of dihedral angles between them,which maybe contributed to free rotation degree of the C-C bond which connects thecentral part and phenyl ring. In the crystalⅡe, the intermolecular N-H…S hydrogenbonds link the molecules into a chain structure and form a R_2~2(8) motif. The pesticidalactivity test was carried on the compounds(Ⅱa-Ⅱh) by dipping method, whichshowed that the compoundsⅡb andⅡc exhibited some pesticidal activity withLC_(50) of the compoundsⅡb andⅡc being 144.61mg/L and 109.55mg/L, respectively.
引文
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