CN1061511C - O,s-二甲基(2,2,2-三氯-1-羟基-乙基)硫代磷酰胺杀虫剂 - Google Patents
O,s-二甲基(2,2,2-三氯-1-羟基-乙基)硫代磷酰胺杀虫剂 Download PDFInfo
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- CN1061511C CN1061511C CN97112828A CN97112828A CN1061511C CN 1061511 C CN1061511 C CN 1061511C CN 97112828 A CN97112828 A CN 97112828A CN 97112828 A CN97112828 A CN 97112828A CN 1061511 C CN1061511 C CN 1061511C
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- acephatemet
- methamidophos
- dimethyl
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- -1 trichloro-1-hydroxy-ethyl Chemical group 0.000 title abstract 3
- 239000002917 insecticide Substances 0.000 claims description 3
- FOCVUCIESVLUNU-UHFFFAOYSA-N Thiotepa Chemical compound C1CN1P(N1CC1)(=S)N1CC1 FOCVUCIESVLUNU-UHFFFAOYSA-N 0.000 claims description 2
- 229960001196 thiotepa Drugs 0.000 claims description 2
- 239000004615 ingredient Substances 0.000 claims 1
- NNKVPIKMPCQWCG-UHFFFAOYSA-N methamidophos Chemical compound COP(N)(=O)SC NNKVPIKMPCQWCG-UHFFFAOYSA-N 0.000 abstract description 24
- 150000001875 compounds Chemical class 0.000 abstract description 19
- 241000238631 Hexapoda Species 0.000 abstract description 11
- 239000000843 powder Substances 0.000 abstract description 4
- 230000000857 drug effect Effects 0.000 abstract description 3
- 239000002994 raw material Substances 0.000 abstract description 3
- 229910052760 oxygen Inorganic materials 0.000 abstract description 2
- RGSNAVQQWDMLSA-UHFFFAOYSA-N NP(O)=S Chemical compound NP(O)=S RGSNAVQQWDMLSA-UHFFFAOYSA-N 0.000 abstract 1
- 230000003042 antagnostic effect Effects 0.000 abstract 1
- 239000002131 composite material Substances 0.000 abstract 1
- 238000003958 fumigation Methods 0.000 abstract 1
- 239000003090 pesticide formulation Substances 0.000 abstract 1
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
- HFFLGKNGCAIQMO-UHFFFAOYSA-N trichloroacetaldehyde Chemical compound ClC(Cl)(Cl)C=O HFFLGKNGCAIQMO-UHFFFAOYSA-N 0.000 description 6
- 238000006243 chemical reaction Methods 0.000 description 4
- JCEGDDHHSZJJHV-UHFFFAOYSA-N methanamine;phosphane Chemical compound P.NC JCEGDDHHSZJJHV-UHFFFAOYSA-N 0.000 description 4
- 239000000575 pesticide Substances 0.000 description 4
- 231100000419 toxicity Toxicity 0.000 description 4
- 230000001988 toxicity Effects 0.000 description 4
- 239000003905 agrochemical Substances 0.000 description 3
- 238000009472 formulation Methods 0.000 description 3
- 230000007062 hydrolysis Effects 0.000 description 3
- 238000006460 hydrolysis reaction Methods 0.000 description 3
- 239000000463 material Substances 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- 238000002360 preparation method Methods 0.000 description 3
- 229940029273 trichloroacetaldehyde Drugs 0.000 description 3
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 2
- 230000008485 antagonism Effects 0.000 description 2
- 238000002425 crystallisation Methods 0.000 description 2
- 150000002148 esters Chemical class 0.000 description 2
- 229960001952 metrifonate Drugs 0.000 description 2
- 125000004430 oxygen atom Chemical group O* 0.000 description 2
- 239000002574 poison Substances 0.000 description 2
- 231100000614 poison Toxicity 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- NFACJZMKEDPNKN-UHFFFAOYSA-N trichlorfon Chemical compound COP(=O)(OC)C(O)C(Cl)(Cl)Cl NFACJZMKEDPNKN-UHFFFAOYSA-N 0.000 description 2
- 238000009736 wetting Methods 0.000 description 2
- 241000345998 Calamus manan Species 0.000 description 1
- 235000007516 Chrysanthemum Nutrition 0.000 description 1
- 244000189548 Chrysanthemum x morifolium Species 0.000 description 1
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 239000000839 emulsion Substances 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 230000008595 infiltration Effects 0.000 description 1
- 238000001764 infiltration Methods 0.000 description 1
- 231100000225 lethality Toxicity 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 238000000034 method Methods 0.000 description 1
- 125000004433 nitrogen atom Chemical group N* 0.000 description 1
- 230000001473 noxious effect Effects 0.000 description 1
- 230000035515 penetration Effects 0.000 description 1
- 235000012950 rattan cane Nutrition 0.000 description 1
- 210000002784 stomach Anatomy 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 230000009885 systemic effect Effects 0.000 description 1
- 231100000331 toxic Toxicity 0.000 description 1
- 230000002588 toxic effect Effects 0.000 description 1
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Abstract
本发明涉及O，S-二甲基(2，2，2-三氯-1-羟基-乙基)硫代磷酰胺作为有效成份在杀虫剂中的应用。该物质由甲胺磷和三氯乙醛化学反应生成，其毒性比甲胺磷降低，是一种杀虫谱广、杀虫效力优良、原料成本低的新杀虫化合物。
Description
本发明属于合成一种新的具有广谱杀虫作用的化合物。
该化合物是以农药甲胺磷为原料，与三氯乙醛化合反应而成，其结构式为：
1．本发明的背景技术是：农药甲胺磷、敌百虫。
甲胺磷是一种高效、广谱杀虫剂，具有优良的触杀作用和较好的内吸作用，有一定的胃毒作用。六十年代，由舍扶隆化学公司开发成商品。
2．本发明的目的是提供一种既完整保留甲胺磷分子结构，又因为通过进一步的化学反应，合成出对抗性昆虫比甲胺磷药效更好，对人毒性更低的新化合物。并能以此为原料，制成可湿性粉剂或其他农药复合型剂型。
3．制备方法：
(1)化学反应式：
(2)工艺过程：
将120g甲胺磷(含量：70％)和140ml苯投入500ml三口烧瓶中，同时加入0．6g催化剂，搅拌下缓缓加入101g三氯乙醛(含量：96％)，于30℃左右搅拌反应4小时，颜色逐渐变为清亮透明的蓝色，反应至终点后，高真空下脱去二分之一的溶剂，冷却结晶12小时，过滤、烘干，得成品149g。
4．本发明化合物与甲胺膦比较，有如下特点：
(1)本发明化合物结构中既完整保留了甲胺磷分子结构，也兼具敌百虫分子结构的半部份(-HCOH-CCL3)，所以，既保留了甲胺磷对昆虫的毒力作用方式，又具有甲胺磷所不具备的熏杀性能。部份农田实验已证实了这一点。
(2)本发明化合物对对甲胺磷有抗性的昆虫有很强的杀伤力。近二十年来，甲胺膦一直是我国广泛使用的主要杀虫剂，昆虫对其已产生了严重的抗药性。而本发明化合物渗入昆虫表皮后，既保留了甲胺磷分子结构对昆虫的生物活性，同时，有部份该化合物被昆虫的水解酶水解生成一些新的具有更高毒效的物质，其结构式有：
抗性昆虫水解酶的水解能力越强，水解产生这些有毒物质也越多，从而提高了对抗性昆虫的药效。
(3)由于甲胺膦的熔点偏低，工业品5℃以下才能结晶，且油溶性差，故国内目前主要使用50％的甲胺磷乳剂，很少见甲胺膦的复合剂型，尚无甲胺磷的固体类制剂。本发明化合物为白色晶状粉末，工业品熔点大于78℃，能溶于氯仿、二甲苯、苯等油性溶剂中，由于熔点增高，可制成粉剂，可湿性粉剂等固体类制剂，由于油溶性增强，也较易将含有甲胺磷分子结构的该化合物与菊酯类等油溶性农药复合成新的杀虫剂型。
(4)本发明化合物酯溶性比甲胺磷强，其对昆虫外表皮的渗透力大于甲胺磷。
(5)奎斯塔得、福藤、梅特卡夫研究了甲胺磷的结构类似物后指出，氮原子上有取代基、氧原子上有取代基、氧原子上或硫原子上的烷基加大，都会降低毒性(见《有机磷农药的化学》P151页)，据此，本发明化合物对人的毒性应低于甲胺磷。
(6)本发明化合物是甲胺磷分子和三氯乙醛分子的完整结合，分子量是甲胺磷的2倍，且生产工艺简单，收率高(90％)，所以，生产每吨该化合物的原料成本低于甲胺磷。
Claims (1)
1．以
结构式表示的O，S-二甲基(2，2，2-三氯-1-羟基-乙基)硫代磷酰胺作为有效成份在杀虫剂中的应用。
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN97112828A CN1061511C (zh) | 1997-06-24 | 1997-06-24 | O,s-二甲基(2,2,2-三氯-1-羟基-乙基)硫代磷酰胺杀虫剂 |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN97112828A CN1061511C (zh) | 1997-06-24 | 1997-06-24 | O,s-二甲基(2,2,2-三氯-1-羟基-乙基)硫代磷酰胺杀虫剂 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CN1203237A CN1203237A (zh) | 1998-12-30 |
| CN1061511C true CN1061511C (zh) | 2001-02-07 |
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| CN97112828A Expired - Fee Related CN1061511C (zh) | 1997-06-24 | 1997-06-24 | O,s-二甲基(2,2,2-三氯-1-羟基-乙基)硫代磷酰胺杀虫剂 |
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Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN100425141C (zh) * | 2007-03-20 | 2008-10-15 | 武汉工程大学 | 一种氯胺磷化合物的应用 |
| CN100479657C (zh) * | 2007-03-14 | 2009-04-22 | 浙江工业大学 | 氯胺磷与环糊精或环糊精衍生物形成的包结物及其制备方法 |
Families Citing this family (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN100360545C (zh) * | 2002-06-07 | 2008-01-09 | 武汉化工学院 | 有机磷酰胺盐酸盐 |
| CN100352822C (zh) * | 2002-11-30 | 2007-12-05 | 黄振东 | 硫代磷酰胺类杀虫剂的衍生物 |
| CN100408586C (zh) * | 2005-05-11 | 2008-08-06 | 武汉工程大学 | 氯胺磷的制备方法 |
| WO2006122444A1 (fr) * | 2005-05-17 | 2006-11-23 | Wuhan Institute Of Technology | Procede de preparation de chloramine-phosphore |
| CN101139359B (zh) * | 2006-09-10 | 2011-11-16 | 李坚 | 氯胺磷的立体异构体,其制备及用途和以该异构体为活性成分的组合物 |
Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DD137839A1 (de) * | 1978-07-18 | 1979-09-26 | Eberhard Guenther | Verfahren zur herstellung 1-substituierter n-(2,2,2-trichloraethyl)-0,0-dialkylphosphorsaeurediesteramide |
-
1997
- 1997-06-24 CN CN97112828A patent/CN1061511C/zh not_active Expired - Fee Related
Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DD137839A1 (de) * | 1978-07-18 | 1979-09-26 | Eberhard Guenther | Verfahren zur herstellung 1-substituierter n-(2,2,2-trichloraethyl)-0,0-dialkylphosphorsaeurediesteramide |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN100479657C (zh) * | 2007-03-14 | 2009-04-22 | 浙江工业大学 | 氯胺磷与环糊精或环糊精衍生物形成的包结物及其制备方法 |
| CN100425141C (zh) * | 2007-03-20 | 2008-10-15 | 武汉工程大学 | 一种氯胺磷化合物的应用 |
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| Publication number | Publication date |
|---|---|
| CN1203237A (zh) | 1998-12-30 |
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Effective date of registration: 20120503 Address after: Liuguqiao village 434035 Jingzhou city of Hubei province Jingzhou district town mi Patentee after: Dongfang Xinnongfu (Jingzhou) Biotechnology Co., Ltd. Address before: 434001 Hubei province Shalongda Limited by Share Ltd financial department Patentee before: Li Jian |
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