CN114026075B - 一种异噁唑啉类化合物及其制备方法和应用 - Google Patents
一种异噁唑啉类化合物及其制备方法和应用 Download PDFInfo
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- GUJOJGAPFQRJSV-UHFFFAOYSA-N dialuminum;dioxosilane;oxygen(2-);hydrate Chemical compound O.[O-2].[O-2].[O-2].[Al+3].[Al+3].O=[Si]=O.O=[Si]=O.O=[Si]=O.O=[Si]=O GUJOJGAPFQRJSV-UHFFFAOYSA-N 0.000 description 1
- 125000004772 dichloromethyl group Chemical group [H]C(Cl)(Cl)* 0.000 description 1
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- YYJNOYZRYGDPNH-MFKUBSTISA-N fenpyroximate Chemical compound C=1C=C(C(=O)OC(C)(C)C)C=CC=1CO/N=C/C=1C(C)=NN(C)C=1OC1=CC=CC=C1 YYJNOYZRYGDPNH-MFKUBSTISA-N 0.000 description 1
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- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
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- 229910052742 iron Inorganic materials 0.000 description 1
- DCYOBGZUOMKFPA-UHFFFAOYSA-N iron(2+);iron(3+);octadecacyanide Chemical compound [Fe+2].[Fe+2].[Fe+2].[Fe+3].[Fe+3].[Fe+3].[Fe+3].N#[C-].N#[C-].N#[C-].N#[C-].N#[C-].N#[C-].N#[C-].N#[C-].N#[C-].N#[C-].N#[C-].N#[C-].N#[C-].N#[C-].N#[C-].N#[C-].N#[C-].N#[C-] DCYOBGZUOMKFPA-UHFFFAOYSA-N 0.000 description 1
- NLYAJNPCOHFWQQ-UHFFFAOYSA-N kaolin Chemical compound O.O.O=[Al]O[Si](=O)O[Si](=O)O[Al]=O NLYAJNPCOHFWQQ-UHFFFAOYSA-N 0.000 description 1
- 239000010985 leather Substances 0.000 description 1
- 229920005610 lignin Polymers 0.000 description 1
- 244000144972 livestock Species 0.000 description 1
- 231100000053 low toxicity Toxicity 0.000 description 1
- WPBNNNQJVZRUHP-UHFFFAOYSA-L manganese(2+);methyl n-[[2-(methoxycarbonylcarbamothioylamino)phenyl]carbamothioyl]carbamate;n-[2-(sulfidocarbothioylamino)ethyl]carbamodithioate Chemical compound [Mn+2].[S-]C(=S)NCCNC([S-])=S.COC(=O)NC(=S)NC1=CC=CC=C1NC(=S)NC(=O)OC WPBNNNQJVZRUHP-UHFFFAOYSA-L 0.000 description 1
- 239000003550 marker Substances 0.000 description 1
- 238000000691 measurement method Methods 0.000 description 1
- 235000013372 meat Nutrition 0.000 description 1
- 229920000609 methyl cellulose Polymers 0.000 description 1
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- 239000008267 milk Substances 0.000 description 1
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- 239000002480 mineral oil Substances 0.000 description 1
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- 229910052750 molybdenum Inorganic materials 0.000 description 1
- 229910052901 montmorillonite Inorganic materials 0.000 description 1
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 229920005615 natural polymer Polymers 0.000 description 1
- 239000005645 nematicide Substances 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 239000004745 nonwoven fabric Substances 0.000 description 1
- 239000002674 ointment Substances 0.000 description 1
- 150000007530 organic bases Chemical class 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 229910052625 palygorskite Inorganic materials 0.000 description 1
- 239000012188 paraffin wax Substances 0.000 description 1
- 239000002297 parasiticide Substances 0.000 description 1
- 238000007911 parenteral administration Methods 0.000 description 1
- 230000000149 penetrating effect Effects 0.000 description 1
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
- 239000001007 phthalocyanine dye Substances 0.000 description 1
- 239000004033 plastic Substances 0.000 description 1
- 229920003023 plastic Polymers 0.000 description 1
- 229920000151 polyglycol Polymers 0.000 description 1
- 239000010695 polyglycol Substances 0.000 description 1
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- 229920002689 polyvinyl acetate Polymers 0.000 description 1
- 229920002451 polyvinyl alcohol Polymers 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- RPDAUEIUDPHABB-UHFFFAOYSA-N potassium ethoxide Chemical compound [K+].CC[O-] RPDAUEIUDPHABB-UHFFFAOYSA-N 0.000 description 1
- 229910000105 potassium hydride Inorganic materials 0.000 description 1
- NTTOTNSKUYCDAV-UHFFFAOYSA-N potassium hydride Chemical compound [KH] NTTOTNSKUYCDAV-UHFFFAOYSA-N 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 239000001294 propane Substances 0.000 description 1
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- 229960003351 prussian blue Drugs 0.000 description 1
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- 210000003689 pubic bone Anatomy 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 239000010453 quartz Substances 0.000 description 1
- 230000006340 racemization Effects 0.000 description 1
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- 208000005687 scabies Diseases 0.000 description 1
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- 150000004760 silicates Chemical class 0.000 description 1
- RMAQACBXLXPBSY-UHFFFAOYSA-N silicic acid Chemical compound O[Si](O)(O)O RMAQACBXLXPBSY-UHFFFAOYSA-N 0.000 description 1
- 210000003491 skin Anatomy 0.000 description 1
- 238000002791 soaking Methods 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 229910000104 sodium hydride Inorganic materials 0.000 description 1
- 239000012312 sodium hydride Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 229920001059 synthetic polymer Polymers 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
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- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- OGIDPMRJRNCKJF-UHFFFAOYSA-N titanium oxide Inorganic materials [Ti]=O OGIDPMRJRNCKJF-UHFFFAOYSA-N 0.000 description 1
- 239000011573 trace mineral Substances 0.000 description 1
- 235000013619 trace mineral Nutrition 0.000 description 1
- 125000003866 trichloromethyl group Chemical group ClC(Cl)(Cl)* 0.000 description 1
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- 239000002023 wood Substances 0.000 description 1
- 150000003738 xylenes Chemical class 0.000 description 1
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Classifications
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- C07D—HETEROCYCLIC COMPOUNDS
- C07D261/00—Heterocyclic compounds containing 1,2-oxazole or hydrogenated 1,2-oxazole rings
- C07D261/02—Heterocyclic compounds containing 1,2-oxazole or hydrogenated 1,2-oxazole rings not condensed with other rings
- C07D261/04—Heterocyclic compounds containing 1,2-oxazole or hydrogenated 1,2-oxazole rings not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member
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- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
- A01N43/72—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms
- A01N43/80—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms five-membered rings with one nitrogen atom and either one oxygen atom or one sulfur atom in positions 1,2
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- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N47/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid
- A01N47/08—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid the carbon atom having one or more single bonds to nitrogen atoms
- A01N47/10—Carbamic acid derivatives, i.e. containing the group —O—CO—N<; Thio analogues thereof
- A01N47/12—Carbamic acid derivatives, i.e. containing the group —O—CO—N<; Thio analogues thereof containing a —O—CO—N< group, or a thio analogue thereof, neither directly attached to a ring nor the nitrogen atom being a member of a heterocyclic ring
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- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N53/00—Biocides, pest repellants or attractants, or plant growth regulators containing cyclopropane carboxylic acids or derivatives thereof
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- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01P—BIOCIDAL, PEST REPELLANT, PEST ATTRACTANT OR PLANT GROWTH REGULATORY ACTIVITY OF CHEMICAL COMPOUNDS OR PREPARATIONS
- A01P7/00—Arthropodicides
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- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/41—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with two or more ring hetero atoms, at least one of which being nitrogen, e.g. tetrazole
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- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D261/00—Heterocyclic compounds containing 1,2-oxazole or hydrogenated 1,2-oxazole rings
- C07D261/02—Heterocyclic compounds containing 1,2-oxazole or hydrogenated 1,2-oxazole rings not condensed with other rings
- C07D261/06—Heterocyclic compounds containing 1,2-oxazole or hydrogenated 1,2-oxazole rings not condensed with other rings having two or more double bonds between ring members or between ring members and non-ring members
- C07D261/10—Heterocyclic compounds containing 1,2-oxazole or hydrogenated 1,2-oxazole rings not condensed with other rings having two or more double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D261/12—Oxygen atoms
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Abstract
本发明公开了一种异噁唑啉类化合物及其制备方法和应用，所述化合物结构如通式I所示：
Description
交叉引用
本发明要求在中国专利局提交的、申请号为201910583893.X、发明名称为“一种异噁唑啉类化合物及其应用”的中国专利申请的优先权，该申请的全部内容通过引用结合在本发明中。
技术领域
本发明涉及一种异噁唑啉类化合物，具体涉及一种新型的异噁唑啉类化合物及其制备方法和应用。
背景技术
专利CN102639529A涉及某些具有杀虫活性的异噁唑啉衍生物。但由于杀虫杀螨剂在使用一段时间后，害虫害螨会对其产生抗性，因此需要不断研发新型的和改进的具有杀虫杀螨活性的新化合物；同时，随着人们对农畜产品等日益增长的需要和对环境保护的日益重视，也一直需要使用高效、广谱且对环境友好的新的杀虫杀螨剂。
发明内容
本发明的目的在于提供一种杀虫杀螨活性好的异噁唑啉类化合物及其制备方法和应用。该异噁唑啉类化合物可用于制备农业和其它领域中防治害虫害螨的药物以及在兽药领域用于制备控制动物寄生虫的药物。
为实现本发明的发明目的，本发明提供了如下技术方案：
一种异噁唑啉类化合物，如通式I所示：
式中：
R1选自氢、氯或氟；
R2选自乙基或2,2,2-三氟乙基；
R3选自C1-C6烷基、C1-C6卤代烷基、C3-C8环烷基或C1-C6烷氧基C1-C6烷基；
或为通式I化合物的立体异构体；
或为通式I化合物的盐；
或为通式I化合物的立体异构体的盐。
在一种可能的实现方式中，通式I中，
R1选自氢、氯或氟；
R2选自乙基或2,2,2-三氟乙基；
R3选自C1-C4烷基、C1-C4卤代烷基、C3-C4环烷基或C1-C4烷氧基C1-C3烷基。
在一种可能的实现方式中，通式I中，
R1选自氢、氯或氟；
R2选自乙基或2,2,2-三氟乙基；
R3选自C1-C4烷基、环丙基或C1-C4烷氧基C1-C2烷基。
在一种可能的实现方式中，通式I化合物的盐包括：通式I化合物与盐酸、氢溴酸、硫酸、磷酸、甲酸、乙酸、丙酸、丁酸、戊酸、三氟乙酸、草酸、丙二酸、甲磺酸、4-甲苯磺酸、苹果酸、富马酸、乳酸、马来酸、水杨酸、酒石酸或柠檬酸形成的盐。
在一种可能的实现方式中，通式I化合物的立体异构体的盐包括：通式I化合物的立体异构体与盐酸、氢溴酸、硫酸、磷酸、甲酸、乙酸、丙酸、丁酸、戊酸、三氟乙酸、草酸、丙二酸、甲磺酸、4-甲苯磺酸、苹果酸、富马酸、乳酸、马来酸、水杨酸、酒石酸或柠檬酸形成的盐。
在一种可能的实现方式中，异噁唑啉类化合物选自表1化合物，所述表1化合物具有如通式I的结构且R1、R2和R3如表1中所示：
表1
或，选自任意一个表1化合物的立体异构体；
或，选自任意一个表1化合物与盐酸、氢溴酸、硫酸、磷酸、甲酸、乙酸、丙酸、丁酸、戊酸、三氟乙酸、草酸、丙二酸、甲磺酸、4-甲苯磺酸、苹果酸、富马酸、乳酸、马来酸、水杨酸、酒石酸或柠檬酸形成的盐；
或，选自任意一个表1化合物的立体异构体与盐酸、氢溴酸、硫酸、磷酸、甲酸、乙酸、丙酸、丁酸、戊酸、三氟乙酸、草酸、丙二酸、甲磺酸、4-甲苯磺酸、苹果酸、富马酸、乳酸、马来酸、水杨酸、酒石酸或柠檬酸形成的盐。
在一种可能的实现方式中，异噁唑啉类化合物选自表2化合物，所述表2化合物具有如通式I的结构且R1、R2和R3如表2中所示：
表2
或，选自任意一个表2化合物的立体异构体；
或，选自任意一个表2化合物与盐酸、氢溴酸、硫酸、磷酸、甲酸、乙酸、丙酸、丁酸、戊酸、三氟乙酸、草酸、丙二酸、甲磺酸、4-甲苯磺酸、苹果酸、富马酸、乳酸、马来酸、水杨酸、酒石酸或柠檬酸形成的盐；
或，选自任意一个表2化合物的立体异构体与盐酸、氢溴酸、硫酸、磷酸、甲酸、乙酸、丙酸、丁酸、戊酸、三氟乙酸、草酸、丙二酸、甲磺酸、4-甲苯磺酸、苹果酸、富马酸、乳酸、马来酸、水杨酸、酒石酸或柠檬酸形成的盐。
在本发明的通式I化合物中，通式I化合物具有两个手性碳原子(如下通式I中标注*和**的碳原子)，因此，通式I化合物中，由*碳原子和**碳原子所表示的手性中心产生了以下四种立体异构体：通式I-1化合物(*碳和**碳均为S构型)、通式I-2化合物(*碳为S构型，**碳为R构型)、通式I-3化合物(*碳为R构型，**碳为S构型)及通式I-4化合物(*碳和**碳均为R构型)。
本发明还包括通式I-1化合物、通式I-2化合物、通式I-3化合物、通式I-4化合物中的任意一种，以及它们所有可能形式的混合物。
当通式I-2化合物和通式I-4化合物以大体上1:1的摩尔比例混合时，则可用通式IA(*碳为外消旋体，**碳原子为R构型)表示；当通式I-1化合物和通式I-3化合物以大体上1:1的摩尔比例混合时，则可用通式IB(*碳为外消旋体，**碳原子为S构型)表示；当通式I-1化合物和通式I-2化合物以大体上1:1的摩尔比例混合时，则可用通式IC(*碳为S构型，**碳原子为外消旋体)表示；当通式I-3化合物和通式I-4化合物以大体上1:1的摩尔比例混合时，则可用通式ID表示(*碳为R构型，**碳原子为外消旋体)。
另外，本发明通式I化合物的其中一种立体异构体能够与另一种立体异构体以任意摩尔比例混合，例如按摩尔比为1:99至99:1混合，又例如按摩尔比为10:1至1:10混合。
在一种可能的实现方式中，通式I化合物的立体异构体为通式IA所示化合物：
在一种可能的实现方式中，通式IA所示化合物选自表3中的化合物，所述表3中的化合物具有如通式IA的结构且R1、R2和R3如表3中所示：
表3
在一种可能的实现方式中，通式IA所示化合物选自表4中的化合物，所述表4中的化合物具有如通式IA的结构且R1、R2和R3如表4中所示：
表4
| 化合物编号 | R1 | R2 | R3 |
| 109 | H | 乙基 | 甲基 |
| 110 | H | 乙基 | 乙基 |
| 111 | H | 乙基 | 异丙基 |
| 112 | H | 乙基 | 环丙基 |
| 113 | H | 乙基 | CH3OCH2- |
| 114 | H | 乙基 | CH3CH2OCH2- |
| 117 | F | 乙基 | 甲基 |
| 118 | F | 乙基 | 乙基 |
| 119 | F | 乙基 | 异丙基 |
| 120 | F | 乙基 | 环丙基 |
| 121 | F | 乙基 | CH3OCH2- |
| 122 | F | 乙基 | CH3CH2OCH2- |
本发明实施例还提供了上述异噁唑啉类化合物的制备方法，如下：
(1)当异噁唑啉类化合物为通式I化合物时，其制备方法如下(式中各基团除另有说明外定义同前)：
通式II化合物与通式III化合物在溶剂中，在温度从-10℃到溶剂沸点下反应0.5～48小时可制得通式I化合物；反应可在碱的存在下进行。
(2)当异噁唑啉类化合物为通式I化合物的立体异构体时，可通过常规的方法得到，如：以具有旋光性的反应原料出发获得具有相应旋光性的反应产物，对外消旋或内消旋的反应产物进行手性拆分等。
(3)当异噁唑啉类化合物为通式I化合物的盐或通式I化合物的立体异构体的盐时，其制备方法如下：通过常规方法以通式I化合物或通式I化合物的立体异构体为反应原料，与相应酸形成酸加成盐，例如，可以制成盐酸、氢溴酸、硫酸、磷酸、甲酸、乙酸、丙酸、丁酸、戊酸、三氟乙酸、草酸、丙二酸、甲磺酸、4-甲苯磺酸、苹果酸、富马酸、乳酸、马来酸、水杨酸、酒石酸或柠檬酸的盐。
在一种可能的实现方式中，溶剂包括：苯、甲苯、二甲苯等芳烃类，丙酮、甲乙酮、甲基异丁基酮等酮类，氯仿、二氯甲烷等卤代烃类，乙酸甲酯、乙酸乙酯等酯类，四氢呋喃、二噁烷、二乙醚、1,2-二甲氧基乙烷等醚类，水、乙腈、N,N-二甲基甲酰胺、N-甲基吡咯烷酮、二甲基亚砜等极性溶剂类中的一种或几种；碱包括：三乙胺、吡啶、DBU、4-二甲氨基吡啶等有机碱，氢化钠、氢化钾等碱金属氢化物，氢氧化钠、氢氧化钾等碱金属氢氧化物，氢氧化钙等碱土类金属氢氧化物，碳酸钠、碳酸钾等碱金属碳酸盐，碳酸氢钠等碱金属碳酸氢盐，甲醇钠、乙醇钾等金属醇盐中的一种或几种。
中间体通式II化合物或其立体异构体可以按公知方法制备，例如参照WO2011067272、WO2013050302、WO2014019950、WO2014029640、WO2014029709或WO2014029639等报道的方法制得。通式III化合物通常有市售，也可按常规方法自制。
本发明实施例还提供了上述异噁唑啉类化合物在制备杀虫剂和/或杀螨剂中的用途。
在一种可能的实现方式中，所述杀虫剂用于防治以下昆虫的一种或多种：
甲虫(鞘翅目昆虫(Coleopteran))，例如绿豆象(Callosobruchus Chinensis)、玉米象(Sitophilus zeamais)、赤拟谷盗(Tribolium Castaneum)、马铃薯瓢虫(Epilachnavigintioctomaculata)、细胸叩甲(Agriotes ogurae fuscicollis)、多色异丽金龟(Anomala rufocuprea)、马铃薯叶甲(Leptinotarsa decemlineata)、叶甲属(Diabroticaspp.)、松墨天牛(Monochamus alternatus endai)、稻根象(Lissorhoptrusoryzophilus)、褐粉蠹(Lyctus bruneus)；
鳞翅目(lepidopteran)害虫，例如，舞毒蛾(Lymantria dispar)、黄褐天幕毛虫(Malacosoma neustria)、菜粉蝶日本亚种(Pieris rapae crucivora)、斜纹夜蛾(Spodoptera litura)、甘蓝夜蛾(Mamestra brassicae)、二化螟(Chilo suppressalis)、欧洲玉米螟(Ostrinia nubilalis)、干果斑螟(Cadra cautella)、chyanokokakumonhamaki(Adoxophyes honmai)、苹果小卷蛾(Cydia pomonella)、黄地老虎(Agrotis segetum)、大蜡螟(Galleria mellonella)、菜蛾(Plutella xylostella)、烟芽夜蛾(Heliothisvirescens)、桔潜蛾(Phyllocnistis citrella)；
半翅目(Hemipterous)害虫，例如，黑尾叶蝉(Nephotettix cincticeps)、褐飞虱(Nilaparvata lugens)、康氏粉蚧(Pseudococcus comstocki)、矢尖盾蚧(Unaspisyanonensis)、桃蚜(Myzus persicas)、苹果蚜(Aphis pomi)、棉蚜(Aphis gossypii)、萝卜蚜(Lipaphis erysimi)、梨冠网蝽(Stephanitis nashi)、绿椿属(Nezara spp.)、温室粉虱(Trialeurodes vaporariorum)、Pshylla spp.；
缨翅目(Thysanoptera)害虫，例如棕榈蓟马(Thrips palmi)、西方花蓟马(Franklinella occidentalis)；
直翅目(orthopteran)害虫，例如非洲蝼蛄(Gryllotalpa Africana)、非洲飞蝗(Locusta migratoria)；
蜚蠊目(blattarian)害虫，例如德国蠊(Blattella germanica)、美洲大蠊(Periplaneta americana)、黄胸散白蚁(Reticulitermes speratus)、家白蚁(Coptotermes formosanus)；
双翅目(Dipterous)害虫，例如家蝇(Musca domestica)、埃及伊蚊(Aedesaegypti)、灰地种蝇(Delia platura)、淡色库蚊(Culex pipiens pallens)、中华按蚊(Anopheles sinensis)、三带喙库蚊(Culex tritaeniorhynchus)、三叶草斑潜蝇(Liriomyza trifolii)等。
在一种可能的实现方式中，所述杀螨剂用于防治以下螨中的一种或多种：朱砂叶螨(Tetranychus cinnabarinus)、棉叶螨(Tetrahychus urticae)、桔全爪螨(Panonychuscitri)、桔刺皮瘿螨(Aculops pelekassi)、跗线螨属(Tarsonemus spp.)等。
在一种可能的实现方式中，所述杀虫剂和/或杀螨剂用于防治粘虫、小菜蛾、二化螟、朱砂叶螨中的一种或几种。
本发明实施例还提供了一种杀虫剂制剂或杀螨剂制剂，该杀虫剂制剂或杀螨剂制剂中含有上述异噁唑啉类化合物作为活性组分，还含有一种或多种辅料。
在一种可能的实现方式中，杀虫剂制剂或杀螨剂制剂选自以下剂型：溶液剂、乳剂、可湿性粉剂、颗粒状可湿性粉剂、悬浮剂、粉剂(powder)、泡沫剂、膏剂、片剂、颗粒剂、气雾剂、经活性化合物浸渍的天然试剂、经活性化合物浸渍的合成试剂、微胶囊剂、种子包衣剂、装备有燃烧装置的制剂(所述燃烧装置可为烟筒和雾筒、罐和盘管等)以及ULV(冷雾剂、热雾剂)等。这些虫剂制剂或杀螨剂制剂或动物寄生虫防治剂可用已知的方法制备，例如可通过将活性组分与填充剂(如：液体稀释剂或载体、液化气稀释剂或载体、固体稀释剂或载体)混合，以及可选地与表面活性剂(即乳化剂和/或分散剂和/或发泡剂)等混合而制备。
在一种可能的实现方式中，所述辅料包括以下的一种或多种：填充剂(如：液体稀释剂或载体、液化气稀释剂或载体、固体稀释剂或载体)、表面活性剂(如：乳化剂和/或分散剂和/或发泡剂)、粘合剂、着色剂；
液体稀释剂或载体可包括，例如，芳香烃(二甲苯、甲苯、烷基萘等)、氯代芳烃或氯代脂族烃(例如氯苯、氯乙烯、二氯甲烷等)、脂族烃(例如环己烷或石蜡(例如矿物油馏分))、醇(例如丁醇、乙二醇，及其醚或酯等)、酮(例如丙酮、甲基乙基酮、甲基异丁基酮、环己酮等)、强极性溶剂(例如二甲基甲酰胺、二甲亚砜)、水等。当使用水作为填充剂时，例如，可使用有机溶剂作为助溶剂；
液化气稀释剂或载体可包括在大气压力和温度下以气体形式存在的那些，例如，丙烷、氮气、二氧化碳，以及气溶胶喷射剂例如卤代烃；
固体稀释剂可包括粉碎的天然矿物(例如高岭土、粘土、滑石、白垩、石英、绿坡缕石、蒙脱石或硅藻土等)以及粉碎的合成矿物(例如细分散的硅酸、氧化铝和硅酸盐等)等；
乳化剂和/或发泡剂可包括非离子及阴离子乳化剂[例如，聚氧乙烯脂肪酸酯、聚氧乙烯脂肪酸醇醚(如烷基芳基聚乙二醇醚)、烷基磺酸盐、烷基硫酸盐和芳基磺酸盐]以及白蛋白水解产物等；
分散剂可包括木质素亚硫酸盐废液和甲基纤维素；
粘合剂可包括羧甲基纤维素、天然或合成的聚合物(例如阿拉伯树胶、聚乙烯醇和聚乙酸乙烯酯等)。
着色剂可包括无机颜料(例如氧化铁、氧化钛和普鲁士蓝等)、有机染料例如茜素染料、偶氮染料或金属酞菁染料；及微量元素，例如铁盐、锰盐、硼盐、铜盐、钴盐、钼盐或锌盐。
此外，本发明的异噁唑啉类化合物可作为与一种增效剂的混合物存在，增效剂自身不必具有活性。更确切地，它是增强活性化合物活性的化合物。
在一种可能的实现方式中，杀虫剂制剂或杀螨剂制剂中含有的上述异噁唑啉类化合物的量为0.1至99重量％，可选地为0.5至90重量％。
本发明实施例还提供了一种杀虫剂组合物或杀螨剂组合物，其包括上述异噁唑啉类化合物和其他活性化合物(例如杀虫剂、毒饵剂、消毒剂、杀螨剂、杀线虫剂、杀真菌剂、生长调节剂、除草剂等)的混合物。该混合物可以以原料药的形式提供，也可以以市售有用制剂的形式或者由其制剂制得的使用形式提供。
本发明实施例还提供了一种控制农业或林业害虫和/或害螨的方法，其包括以下步骤：将有效剂量的材料施用于需要控制的害虫害螨或其生长介质上，所述材料选自下组中的一种或多种：上述异噁唑啉类化合物、上述杀虫剂制剂或杀螨剂制剂、上述杀虫剂组合物或杀螨剂组合物。
本发明实施例还提供了上述异噁唑啉类化合物在制备动物寄生虫防治剂中的用途。在兽医领域内，即，兽医科学中，本发明异噁唑啉类化合物可以有效地用于对抗多种有害的动物类寄生虫，特别是体内寄生虫和体外寄生虫。
在一种可能的实现方式中，动物寄生虫包括以下的一种或多种：
虱目(Anoplurida)，例如血虱属(Haematopinus spp.)、毛虱属(Linognathusspp.)、虱属(Pediculus spp.)、Phtirus spp和管虱属(Solenopotes spp.)；特别地，代表性实例有，棘颚虱(Linognathus setosus)、牛管虱(Solenopotes capillatus)；
食毛目(Mallopha、牛颚虱(Linognathus vituli)、绵羊颚虱(Linognathusovillus)、Linognathus oviformis、足颚虱(Linognathus pedalis)、山羊颚虱(Linognathus stenopsis)、驴血虱(Haematopinus asini macrocephalus)、牛血虱(Haematopinus eurysternus)、猪血虱(Haematopinus suis)、头虱(Pediculus humanuscapitis)、体虱(Pediculus humanus corporis)、葡萄根瘤蚜(Phylloera vastatrix)、阴虱(Phthirus pubis)gida)和钝角亚目(Amblycerina)和细角亚目(Ischnocerin)，例如，毛羽虱属(Trimenopon spp.)、禽虱属(Menopon spp.)、巨羽虱属(Trinoton spp.)、牛羽虱属(Bovicola spp.)、Werneckiella spp.、Lepikentron spp.、畜虱属(Damalina spp.)、嚼虱属(Trichodectes spp.)和猫羽虱属(Felicola spp.)；特别地，代表性实例有，牛毛虱(Bovicola bovis)、羊毛虱(Bovicola ovis)、安哥拉山羊羽虱(Bovicola limbata)、牛畜虱(Damalina bovis)、犬毛虱(Trichodectes canis)、猫羽虱(Felicola subrostratus)、山羊毛虱(Bovicola caprae)、Lepikentron ovis、咬虱(Werneckiella equi)；
双翅目(Diptera)及其长角亚目(Nematocerina)和短角亚目(Brachycerina)，例如，伊蚊属(Aedes spp.)、按蚊属(Anopheles spp.)、库蚊属(Culex spp.)、蚋属(Simuliumspp)、真蚋属(Eusimulium spp.)、白蛉属(Phlebotomus spp.)、罗蛉属(Lutzomyia spp.)、库蠓属(Culicoides spp.)、斑虻属(Chrysops spp.)、短蚋属(Odagmia spp.)、维蚋属(Wilhelmia spp.)、瘤虻属(Hybomitra spp.)、黄虻属(Atylotus spp.)、虻属(Tabanusspp.)、麻虻属(Haematopota spp.)、Philipomyia spp.、蜂虱蝇属(Braula spp.)、家蝇属(Musca spp.)、齿股蝇属(Hydrotaea spp.)、螫蝇属(Stomoxys spp.)、黑角蝇属(Haematobia spp.)、莫蝇属(Morellia spp.)、厕蝇属(Fannia spp.)、舌蝇属(Glossinaspp.)、丽蝇属(Calliphora spp.)、绿蝇属(Lucilia spp.)、金蝇属(Chrysomyia spp.)、污蝇属(Wohlfahrtia spp.)、麻蝇属(Sarcophaga spp.)、狂蝇属(Oestrus spp.)、皮蝇属(Hypoderma spp.)、胃蝇属(Gasterophilus spp.)、虱蝇属(Hippobosca spp.)、羊虱蝇属(Lipoptena spp.)、蜱蝇属(Melophagus spp.)、鼻狂蝇属(Rhinoestrus spp.)、大蚊属(Tipula spp.)；特别地，代表性实例有，埃及伊蚊(Aedes aegypti)、白纹伊蚊(Aedesalbopictus)、带喙伊蚊(Aedes taeniorhynchus)、冈比亚按蚊(Anopheles gambiae)、五斑按蚊(Anopheles maculipennis)、红头丽蝇(Calliphora erythrocephala)、高额麻虻(Chrysozona pluvialis)、五带淡色库蚊(Culex quinquefasciatus)、尖音库蚊(Culexpipiens)、环喙库蚊(Culex tarsalis)、夏厕蝇(Fannia canicularis)、肉蝇(Sarcophagacarnaria)、厩螯蝇(Stomoxys calcitrans)、欧洲大蚊(Tipula paludosa)、铜绿蝇(Lucilia cuprina)、丝光绿蝇(Lucilia sericata)、爬蚋(Simulium reptans)、静食白蛉(Phlebotomus papatasi)、长须白蛉(Phlebotomus longipalpis)、华丽短蚋(Odagmiaornata)、马维蚋(Wilhelmia equina)、红头厌蚋(Boophthora erythrocephala)、多声虻(Tabanus bromius)、夜蛾虻(Tabanus spodopterus)、北美黑虻(Tabanus atratus)、猪虻(Tabanus sudeticus)、古氏瘤虻(Hybomitra ciurea)、盲斑虻(Chrysops caecutiens)、黄缘斑虻(Chrysops relictus)、高额麻虻(Haematopota pluvialis)、Haematopotaitalica、秋家蝇(Musca autumnalis)、家蝇(Musca domestica)、西方角蝇(Haematobiairritans irritans)、西方角蝇(Haematobia irritans exigua)、刺扰血蝇(Haematobiastimulans)、Hydrotaea irritans、白斑齿股蝇(Hydrotaea albipuncta)、Chrysomyachloropyga、蛆症金蝇(Chrysomya bezziana)、羊狂蝇(Oestrus ovis)、牛皮蝇(Hypodermabovis)、纹皮蝇(Hypoderma lineatum)、Przhevalskiana silenus、人肤蝇(Dermatobiahominis)、羊蜱蝇(Melophagus ovinus)、Lipoptena capreoli、鹿羊虱蝇(Lipoptenacervi)、Hippobosca variegata、马虱蝇(Hippobosca equina)、肠胃蝇(Gasterophilusintestinalis)、赤尾胃蝇(Gasterophilus haemorroidalis)、裸节胃蝇(Gasterophilusinterrnis)、鼻胃蝇(Gasterophilus nasalis)、黑角胃蝇(Gasterophilus nigricornis)、黑腹胃蝇(Gasterophilus pecorum)、蜂虱蝇(Braula coeca)；
蚤目(Siphonapterida)，例如，蚤属(Pulex spp.)、栉首蚤属(Ctenocephalidesspp.)、潜蚤属(Tunga spp.)、客蚤属(Xenopsylla spp.)、角叶蚤属(Ceratophyllusspp.)；特别地，代表性实例有，犬栉首蚤(Ctenocephalides canis)、猫栉首蚤(Ctenocephalides felis)、人蚤(Pulex irritans)、穿皮潜蚤(Tunga penetrans)、印鼠客蚤(Xenopsylla cheopis)；
异翅目(Heteropterida)，例如，臭虫属(Cimex spp.)、锥猎椿属(Triatomaspp.)、红猎蝽属(Rhodnius spp.)、锥蝽属(Panstrongylus spp.)；
蜚蠊目(Blattarida)，例如，东方蜚蠊(Blatta orientalis)、美洲大蠊、德国蠊、夏柏拉蟑螂属(Supella spp.)(例如，Suppella longipalpa)；
蜱螨目(Acari)(或Acarina)，后气门目(Metastigmata)和中气门目(Mesostigmata)，例如，锐缘蜱属(Argas spp.)、钝缘蜱属(Ornithodorus spp.)、残喙蜱属(Otobius spp.)、硬蜱属(Ixodes spp.)、花蜱属(Amblyomma spp.)、牛蜱属(Rhipicephalus(Boophilus)spp.)、革蜱属(Dermacentor spp.)、Haemophysalis spp.、璃眼蜱属(Hyalomma spp.)、皮刺螨属(Dermanyssus spp.)、扇头蜱属(Rhipicephalus spp.)(异主寄生型螨的原属)、禽刺螨属(Ornithonyssus spp.)、肺刺螨属(Pneumonyssusspp.)、Pneumonyssus spp.、刺利螨属(Raillietia spp.)、肺刺螨属(Pneumonyssusspp.)、胸刺螨属(Sternostoma spp.)、蜂螨属(Varroa spp.)、蜂盾螨属(Acarapis spp.)；特别地，代表性实例有，波斯锐缘蜱(Argas persicus)、鸽锐缘蜱(Argas reflexus)、非洲钝缘蜱(Ornithodorus moubata)、耳残喙蜱(Otobius megnini)、微小扇头蜱(微小牛蜱)(Rhipicephalus(Boophilus)microplus)、消色扇头蜱(消色牛蜱)(Rhipicephalus(Boophilus)decoloratus)、具环扇头蜱(具环牛蜱)(Rhipicephalus(Boophilus)annulatus)、有矩扇头蜱(有矩牛蜱)(Rhipicephalus(Boophilus)calceratus)、Hyalommaanatolicum、埃及璃眼蜱(Hyalomma aegypticum)、Hyalomma marginatum、Hyalommatransiens、外翻扇头蜱(Rhipicephalus evertsi)、蓖子硬蜱(Ixodes ricinus)、六角硬蜱(Ixodes hexagonus)、原野硬蜱(Ixodes canisuga)、多毛硬蜱(Ixodes pilosus)、浅红硬蜱(Ixodes rubicundus)、肩突硬蜱(Ixodes scapularis)、全环硬蜱(Ixodesholocyclus)、嗜群血蜱(Haemaphysalis concinna)、刻点血蜱(Haemaphysalispunctata)、Haemaphysalis cinnabarina、Haemaphysalis otophila、犬血蜱(Haemaphysalis leachi)、长角血蜱(Haemaphysalis longicorni)、边缘革蜱(Dermacentor marginatus)、网纹革蜱(Dermacentor reticulatus)、Dermacentorpictus、白纹革蜱(Dermacentor albipictus)、安氏革蜱(Dermacentor andersoni)、变异革蜱(Dermacentor variabilis)、毛里求斯璃眼蜱(Hyalomma mauritanicum)、血红扇头蜱(Rhipicephalus sanguineus)、囊形扇头蜱(Rhipicephalus bursa)、非洲扇头蜱(Rhipicephalus appendiculatus)、好望角扇头蜱(Rhipicephalus capensis)、图兰扇头蜱(Rhipicephalus turanicus)、Rhipicephalus zambeziensis、美洲花蜱(Amblyommaamericanum)、彩饰花蜱(Amblyomma variegatum、有斑花蜱(Amblyomma maculatum)、希伯来花蜱(Amblyomma hebraeum)、卡延花蜱(Amblyomma cajennense)、鸡皮刺螨(Dermanyssus gallinae)、囊禽刺螨(Ornithonyssus bursa)、林禽刺螨(Ornithonyssussylviarum)、大蜂螨(Varroa jacobsconi)；
轴螨目(Actinedida)(前气门亚目(Prostigmata))和粉螨目(Acaridida)(无气门亚目(Astigmata))，例如，蜂盾螨属(Acarapis spp.)、姬螯螨属(Cheyletiella spp.)、禽螯螨属(Ornithocheyletia spp.)、肉螨属(Myobia spp.)、疮螨属(Psorergates spp.)、蠕形螨属(Demodex spp.)、恙螨属(Trombicula spp.)、Listrophorus spp.、粉螨属(Acarusspp.)、食酪螨属(Tyrophagus spp.)、嗜木螨属(Caloglyphus spp.)、颈下螨属(Hypodectes spp.)、翅螨属(Pterolichus spp.)、痒螨属(Psoroptes spp.)、皮螨属(Chorioptes spp.)、耳疥螨属(Otodectes spp.)、疥螨属(Sarcoptes spp.)、耳螨属(Notoedres spp.)、疙螨属(Knemidocoptes spp.)、气囊螨属(Cytodites spp.)和鸡雏螨属(Laminosioptes spp.)；特别是，雅氏姬螯螨(C heyletiella yasguri)、布氏姬螯螨(Cheyletiella blakei)、犬蠕形螨(Demodex canis)、牛蠕形螨(Demodex bovis)、绵羊蠕形螨(Demodex ovis)、山羊蠕形螨(Demodex caprae)、马蠕形螨(Demodex equi)、Demodexcaballi、猪蠕形螨(Demodex suis)、Neotrombicula autumnalis、Neotrombiculadesaleli、Neoschonegastia xerothermobia、秋收恙螨(Trombicula akamushi)、狗耳螨(Otodectes cynotis)、猫痂螨(Notoedres cati)、狗疥螨(Sarcoptis canis)、牛疥螨(Sarcoptes bovis)、绵羊疥螨(Sarcoptes ovis)、山羊疥螨(Sarcoptes rupicaprae(＝S.caprae))、马疥螨(Sarcoptes equi)、猪疥螨(Sarcoptes suis)、绵羊瘙螨(Psoroptesovis)、兔瘙螨(Psoroptes cuniculi)、马瘙螨(Psoroptes equi)、牛痒螨(Chorioptesbovis)、Psoergates ovis、Pneumonyssoidic mange、犬鼻疥蟲(Pneumonyssoidescaninum)、伍氏蜂跗线螨(Acarapis woodi)；
线虫，例如南方根结线虫(Meloidogyne incognita)、松材线虫(Bursaphelenchusxylophilus)、水稻干尖线虫(Aphelenchoides besseyi)、大豆异皮线虫(Heteroderaglycines)、短体线虫属(Pratylenchus spp.)等；
侵袭动物的节肢动物、蠕虫和疟原虫。防治节肢动物、蠕虫和/或疟原虫，可减少家养动物的死亡率，并且可改善动物的生产率(肉、奶、毛、皮、蛋和蜜)和健康。
在一种可能的实现方式中，所述动物寄生虫防治剂用于防治猫蚤、美洲犬蜱中的一种或几种。
在一种可能的实现方式中，动物包括以下的一种或多种：农业动物，例如牛、绵羊、山羊、马、猪、驴、骆驼、水牛、兔、家鸡、火鸡、鸭、鹅、养殖鱼、蜜蜂等；也包括被称为伴侣动物的宠物，例如，狗、猫、笼鸟、观赏鱼；还包括用于实验的动物，例如仓鼠、豚鼠、大鼠和小鼠等。
本发明实施例还提供了一种动物寄生虫防治剂，该动物寄生虫防治剂中含有上述异噁唑啉类化合物作为活性组分，还含有一种或多种辅料。
在一种可能的实现方式中，动物寄生虫防治剂选自以下剂型：片剂、胶囊剂、饮剂、可饮用药、颗粒剂、膏剂和丸剂、栓剂、注射剂(肌肉、皮下、静脉内、腹膜内等)、涂抹剂、气雾剂、无压喷雾剂(例如泵喷雾剂和雾化喷雾剂)。
在一种可能的实现方式中，动物寄生虫防治剂中含有的上述活性组分的量为1至80重量％的量。
本发明实施例还提供了一种动物寄生虫防治组合物，其包括上述异噁唑啉类化合物和其他动物寄生虫防治活性化合物(例如杀螨剂、杀昆虫剂、杀寄生虫剂、抗疟原虫剂等)的混合物。该混合物可以以原料药的形式提供，也可以以市售有用制剂的形式或者由其制剂制得的使用形式提供。
本发明实施例还提供了一种控制动物寄生虫的方法，其包括以下步骤：将有效剂量的材料施于需要控制的动物寄生虫或其生长介质上，所述材料选自下组中的一种或多种：上述异噁唑啉类化合物；上述动物寄生虫防治剂；上述动物寄生虫防治组合物。例如：采用片剂、胶囊剂、饮剂、可饮用药、颗粒剂、膏剂、丸剂、栓剂进行肠内给药；基于皮肤施用的非肠内给药，例如注射(肌肉、皮下、静脉内、腹膜内等)、植入、鼻部给药，包括洗浴或浸泡、喷雾、泼浇、点滴、清洗和撒粉，和通过使用含有活性化合物的模型制品，例如项圈、耳标、标签、腿部缚带(leg brace)、网、标识器等施用。本发明的活性化合物具有低毒性，可以安全地用于温血动物。
有益效果
本发明的异噁唑啉类化合物具有意想不到的优异的杀虫杀螨效果，其也对有毒的害虫展现出合适的防治效果，且对栽培的作物植物没有植物毒性。此外，本发明的化合物可用于防治多种害虫，例如有害的刺吸式昆虫、咀嚼式昆虫以及其他植物寄生害虫、储存谷物害虫、卫生害虫等，并且可用于消毒和杀灭它们。
具体实施方式
为使本发明实施例的目的、技术方案和优点更加清楚，下面将对本发明实施例中的技术方案进行清楚、完整地描述，显然，所描述的实施例是本发明一部分实施例，而不是全部的实施例。基于本发明中的实施例，本领域普通技术人员在没有作出创造性劳动前提下所获得的所有其他实施例，都属于本发明保护的范围。
另外，为了更好的说明本发明，在下文的具体实施方式中给出了众多的具体细节。本领域技术人员应当理解，没有某些具体细节，本发明同样可以实施。在一些实施例中，对于本领域技术人员熟知的原料、元件、方法、手段等未作详细描述，以便于凸显本发明的主旨。
除非另有其它明确表示，否则在整个说明书和权利要求书中，术语“包括”或其变换如“包含”或“包括有”等等将被理解为包括所陈述的元件或组成部分，而并未排除其它元件或其它组成部分
除另有注明外，所用原料均有市售。
本发明中，所用术语具有如下含义：
上面给出的通式化合物的定义中，汇集所用术语一般代表如下取代基：
烷基：直链或支链烷基，例如甲基、乙基、正丙基、异丙基或不同的丁基、戊基或己基异构体。
卤代烷基：直链或支链烷基，在这些烷基上的氢原子可部分或全部被卤素所取代，例如氯甲基、二氯甲基、三氯甲基、氟甲基、二氟甲基、三氟甲基、2,2,2-三氟乙基、七氟异丙基、1,1,2,2,2-五氟乙基等。
环烷基：取代或未取代的环状烷基，例如环丙基、环戊基或环己基；取代基如甲基、卤素、氰基等。
烷氧基烷基：烷基-O-烷基-，例如CH3OCH2-、CH3CH2OCH2-、CH3CH2CH2OCH2-、(CH3)2CHOCH2-、CH3CH2CH2CH2OCH2-、(CH3)3COCH2-、CH3OCH2CH2-、CH3CH2OCH2CH2-、CH3CH2CH2OCH2CH2-或CH3CH2CH2CH2OCH2CH2-等。
动物寄生虫防治剂：是指能有效地将被寄生虫感染的动物中的各种寄生虫的发病率减少的活性化合物。防治意味着活性化合物能有效地杀灭寄生虫、抑制其生长或繁殖。
杀虫剂：对害虫具有杀虫效果的物质。
杀螨剂：用于防治植食性害螨的药剂。
合成实施例
按照上述记载的合成路线，采用不同的原料化合物，即可分别制备获得本发明通式I所示化合物，进一步具体描述如下：
实施例1：化合物109的制备
向反应瓶中加入0.30g(0.57mmol)4-(5-(3,5-二氯苯基)-5-(三氟甲基)-4,5-二氢异噁唑-3-基)-N-((R)-2-乙基-3-氧代恶唑烷-4-基)-2-甲基苯甲酰胺、20ml甲苯及0.11g(1.09mmol)三乙胺，再加入66.35mg(0.85mmol)乙酰氯，升温至回流反应。TLC监测反应结束后，向反应液中加入水，并用乙酸乙酯萃取，有机相用无水硫酸镁干燥，过滤、浓缩，柱层析纯化得0.13g油状物。
化合物109的核磁及质谱数据如下：
1H NMR(600MHz,DMSO-d6)δ7.83(t,1H),7.71(s,1H),7.67(dt,1H),7.64(d,2H),7.55(d,1H),5.21(t,1H),4.52–4.29(m,4H),3.56–3.40(m,2H),2.40(s,3H),2.15(s,3H),1.13(t,3H).ESI-MS,m/Z:594.23[M+Na]+。
实施例2：化合物112的制备
向反应瓶中加入0.50g(0.95mmol)4-(5-(3,5-二氯苯基)-5-(三氟甲基)-4,5-二氢异噁唑-3-基)-N-((R)-2-乙基-3-氧代恶唑烷-4-基)-2-甲基苯甲酰胺、25ml甲苯及0.19g(1.88mmol)三乙胺，再加入0.15g(1.44mmol)环丙基甲酰氯，升温至回流反应。TLC监测反应结束后，向反应液中加入水，并用乙酸乙酯萃取，有机相用无水硫酸镁干燥，过滤、浓缩，柱层析纯化得0.29g黄色固体。
化合物112的核磁及质谱数据如下：
1H NMR(600MHz,Chloroform-d)δ7.63(d,1H),7.60(s,1H),7.56–7.49(m,3H),7.44(t,1H),5.56(t,1H),4.56–4.42(m,2H),4.08(d,1H),3.75–3.56(m,3H),2.52(s,3H),1.40–1.15(m,4H),1.11–0.94(m,2H),0.60(br s,2H).ESI-MS,m/Z:530.2[M+H]+。
实施例3：化合物113的制备
向反应瓶中加入1.00g(1.89mmol)4-(5-(3,5-二氯苯基)-5-(三氟甲基)-4,5-二氢异噁唑-3-基)-N-((R)-2-乙基-3-氧代恶唑烷-4-基)-2-甲基苯甲酰胺、30ml甲苯及0.38g(3.76mmol)三乙胺，再加入0.31g(2.87mmol)甲氧基乙酰氯，升温至回流反应。TLC监测反应结束后，向反应液中加入水，并用乙酸乙酯萃取，有机相用无水硫酸镁干燥，过滤、浓缩，柱层析纯化得0.53g油状物。
化合物113的核磁及质谱数据如下：
1H NMR(600MHz,DMSO-d6)δ7.82(t,1H),7.72(t,1H),7.68–7.65(m,1H),7.63(d,2H),7.57(dd,1H),5.08(t,1H),4.49–4.28(m,4H),4.15(s,2H),3.57–3.36(m,2H),3.22(s,3H),2.39(s,3H),1.12(t,3H).ESI-MS,m/Z:624.25[M+Na]+。
实施例4：化合物114的制备
参照实施例3的合成方法制得化合物114(油状物)。
化合物114的核磁及质谱数据如下：
1H NMR(600MHz,DMSO-d6)δ7.83(t,1H),7.72(t,1H),7.69–7.66(m,1H),7.64(d,2H),7.57(dd,1H),5.08(t,1H),4.48–4.30(m,4H),4.20(s,2H),3.54–3.39(m,4H),2.40(s,3H),1.13(t,3H),1.09(t,3H).ESI-MS,m/Z:638.37[M+Na]+。
实施例5：化合物120的制备
参照实施例2的合成方法制得化合物120(黄色固体)。
化合物120的核磁及质谱数据如下：
1H NMR(600MHz,DMSO-d6)δ7.82(d,2H),7.69(s,1H),7.66(d,1H),7.56(d,1H),5.54(td,1H),4.58(t,1H),4.46–4.30(m,3H),3.57–3.44(m,2H),2.43(s,3H),1.42–1.35(m,1H),1.15(t,3H),0.87–0.78(m,2H),0.77–0.58(m,2H).ESI-MS,m/Z:616.30[M+H]+。
实施例6：化合物121的制备
参照实施例3的合成方法制得化合物121(油状物)。
化合物121的核磁及质谱数据如下：
1H NMR(600MHz,DMSO-d6)δ7.81(d,2H),7.71(t,1H),7.68–7.64(m,1H),7.57(dd,1H),5.08(t,1H),4.48–4.29(m,4H),4.15(s,2H),3.53–3.40(m,2H),3.22(s,3H),2.39(s,3H),1.13(t,3H).ESI-MS,m/Z:642.13[M+Na]+。
实施例7：化合物122的制备
参照实施例3的合成方法制得化合物122(油状物)。
化合物122的核磁及质谱数据如下：
1H NMR(600MHz,DMSO-d6)δ7.82(d,2H),7.73–7.64(m,2H),7.58(dd,1H),5.08(t,1H),4.49–4.31(m,4H),4.20(s,2H),3.55–3.40(m,4H),2.40(s,3H),1.13(t,3H),1.09(t,3H).ESI-MS,m/Z:656.34[M+Na]+。
参照以上实施例可以制备本发明通式I中其它化合物。
生物活性测定
实施例8：粘虫、小菜蛾、二化螟的生物活性测定
用本发明化合物对几种昆虫进行了杀虫活性测定实验。测定方法如下：
待测化合物用丙酮/甲醇(1:1)的混合溶剂溶解后，用含有0.1％(wt)吐温80的水稀释至所需的浓度。
以粘虫、小菜蛾、二化螟为靶标，采用Airbrush喷雾法进行活性测定。
(1)杀粘虫的活性测定
测定方法：将玉米叶片剪成长2cm的叶段，Airbrush喷雾处理的压力为10psi(约合0.7kg/cm2)，每叶段正反面喷雾，待测化合物的喷液量为0.5ml。阴干后每处理接入10头3龄幼虫，每处理3次重复。处理后放入25℃、相对湿度60～70％观察室内培养，药后3天调查存活虫数，计算死亡率。
对粘虫的部分测试结果如表5所示：
表5本发明化合物对粘虫的杀虫测试结果
本发明实施例中通过对式I化合物中的R1、R2、R3基团进行选择，获得了杀虫杀螨杀寄生虫效果更好的化合物，从上表中可以看出，当R3选择甲氧基(即上表中按照本发明制备方法制备得到的对比化合物)时，其对粘虫的活性要远小于本发明实施例中的化合物。
(2)杀小菜蛾的活性测定
测定方法：将甘蓝叶片用打孔器打成直径2cm的叶碟，Airbrush喷雾处理的压力为10psi(约合0.7kg/cm2)，每叶碟正反面喷雾，待测化合物的喷液量为0.5ml。阴干后每处理接入10头3龄幼虫，每处理3次重复。处理后放入25℃、相对湿度60～70％观察室内培养，药后3天调查存活虫数，计算死亡率。
对小菜蛾的部分测试结果如表6所示：
表6本发明化合物对小菜蛾的杀虫测试结果
本发明实施例中通过对式I化合物中的R1、R2、R3基团进行选择，获得了杀虫杀螨杀寄生虫效果更好的化合物，从上表中可以看出，当R3选择甲氧基(即上表中按照本发明制备方法制备得到的对比化合物)时，其对小菜蛾的活性要远小于本发明实施例中的化合物。
(3)杀二化螟的活性测定
测定方法：1)稻苗准备：在恒温室(温度26～28℃、相对湿度60～80％左右，光照16hL:8hD)内用直径为4.5cm、高4cm塑料小杯培养水稻，待水稻长至4～5叶期时，选择健壮的、长势一致的水稻幼苗进行药剂处理，每处理设3次重复。2)试虫准备：室内连续饲养的二化螟，3龄幼虫。3)稻茎喷雾接虫。采用喷雾法，对稻苗进行全株均匀喷雾处理，每处理用药15ml。先处理空白对照，然后按试验浓度由低到高的顺序重复上述操作。稻苗喷雾处理后，放置阴凉处将药液晾干，剪取茎基部上5厘米左右茎秆饲喂试虫。准备直径90mm的玻璃培养皿，皿底垫滤纸，加水保湿，每皿放入约5根稻茎，接幼虫10头，用无纺布密闭培养皿，置于恒温房间培养。药后3天调查残留活虫数。
对二化螟的部分测试结果如表7所示：
表7本发明化合物对二化螟的杀虫测试结果
本发明实施例中通过对式I化合物中的R1、R2、R3基团进行选择，获得了杀虫杀螨杀寄生虫效果更好的化合物，从上表中可以看出，当R3选择甲氧基(即上表中按照本发明制备方法制备得到的对比化合物)时，其对二化螟的活性要远小于本发明实施例中的化合物。
实施例9：朱砂叶螨的生物活性测定
用本发明化合物进行温室杀螨活性测定。测定的方法如下：
根据待测化合物的溶解性，用丙酮或二甲基亚砜溶解，并用0.1％的吐温80溶液配制所需浓度的待测溶液50毫升，丙酮或二甲基亚砜在溶液中的含量不超过10％。
取两片真叶菜豆苗，接种朱砂叶螨成螨30-40头，调查基数后，用手持喷雾器进行整株喷雾处理，每处理3次重复，处理后置于标准观察室，72小时后调查存活螨数，计算死亡率。
对朱砂叶螨的部分测试结果如表8所示：
表8本发明化合物对朱砂叶螨的杀螨测试结果
本发明实施例中通过对式I化合物中的R1、R2、R3基团进行选择，获得了杀虫杀螨杀寄生虫效果更好的化合物，从上表中可以看出，当R3选择甲氧基(即上表中按照本发明制备方法制备得到的对比化合物)时，其对朱砂叶螨的活性要远小于本发明实施例中的化合物。
实施例10：对猫蚤的杀虫试验
将4mg待测化合物溶解于40ml丙酮，获得浓度100ppm的丙酮溶液，在内径5.3cm的培养皿的底面和侧面上涂布400μl药液，然后待丙酮挥发，在培养皿的内壁上制作本发明化合物的薄膜。所使用的培养皿的内壁为40cm2，处理药量为1μg/cm2；向其中放入10只猫蚤成虫(雌雄混合)，盖好后在25℃的恒温室内保存。检查72h后的死虫数，计算死虫率。试验按3次重复进行。测试结果：化合物109、112、113、114、120、121、122显示出70％以上的死虫率。
实施例11：对美洲犬蜱的杀虫试验
将4mg待测化合物溶解于40ml丙酮，获得浓度100ppm的丙酮溶液，在2个内径5.3cm的培养皿的底面和侧面上，涂布400μl药液，然后待丙酮挥发，在培养皿的内壁上制作本发明化合物的薄膜。所使用的培养皿的内壁为40cm2，处理药量为1μg/cm2。向其中放入10只美洲犬蜱的第1若虫(雌雄混合)，合并2个培养皿，使用胶带密封结合部以防止逃亡，在25℃的恒温室中保存。检查24h后的死虫数，计算死虫率。试验按3次重复进行。测试结果：化合物109、112、113、114、120、121、122显示出70％以上的死虫率。
工业实用性
本发明公开了一种异噁唑啉类化合物及其制备方法和应用，该异噁唑啉类化合物具有意想不到的优异的杀虫杀螨效果，其也对有毒的害虫展现出合适的防治效果，且对栽培的作物植物没有植物毒性。此外，本发明的化合物可用于防治多种害虫，例如有害的刺吸式昆虫、咀嚼式昆虫以及其他植物寄生害虫、储存谷物害虫、卫生害虫等，并且可用于消毒和杀灭它们。
Claims (9)
1.一种异噁唑啉类化合物，其特征在于如通式IA所示：
式中：
R1选自氢、氯或氟；
R2选自乙基；
R3选自C1-C4烷基、环丙基或C1-C4烷氧基C1-C2烷基；
或为通式IA化合物的盐。
2.根据权利要求1所述的异噁唑啉类化合物，其特征在于，通式IA化合物的盐为：通式IA化合物与盐酸、氢溴酸、硫酸、磷酸、甲酸、乙酸、丙酸、丁酸、戊酸、三氟乙酸、草酸、丙二酸、甲磺酸、4-甲苯磺酸、苹果酸、富马酸、乳酸、马来酸、水杨酸、酒石酸或柠檬酸形成的盐。
3.根据权利要求1所述的异噁唑啉类化合物，其特征在于，异噁唑啉类化合物选自表4化合物，所述表4化合物具有如通式IA的结构且R1、R2和R3如表4中所示；
表4
或为通式IA化合物的盐。
4.一种权利要求1所述的异噁唑啉类化合物的制备方法，其特征在于，当异噁唑啉类化合物为通式IA化合物时，其制备方法如下，反应式中R1、R2和R3的含义与权利要求1中相同：
通式II化合物与通式III化合物在溶剂中，在温度从-10℃到溶剂沸点下反应0.5～48小时制得通式IA化合物；反应在碱的存在下进行。
5.一种根据权利要求1-3之一所述的异噁唑啉类化合物在制备杀虫剂和/或杀螨剂中的用途。
6.根据权利要求5所述的用途，其特征在于：所述杀虫剂和/或杀螨剂用于防治粘虫、小菜蛾、二化螟、朱砂叶螨中的一种或几种。
7.一种杀虫剂制剂或杀螨剂制剂，其特征在于：所述杀虫剂制剂或杀螨剂制剂中含有权利要求1-3之一所述的异噁唑啉类化合物作为活性组分，还含有一种或多种辅料。
8.根据权利要求7所述的杀虫剂制剂或杀螨剂制剂，其特征在于：所述杀虫剂制剂或杀螨剂制剂中权利要求1-3之一所述的异噁唑啉类化合物的量为0.1至99重量％。
9.根据权利要求8所述的杀虫剂制剂或杀螨剂制剂，其特征在于：所述杀虫剂制剂或杀螨剂制剂中权利要求1-3之一所述的异噁唑啉类化合物的量为0.5至90重量％。
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| EP2887810B1 (en) | 2012-08-24 | 2018-10-31 | Syngenta Participations AG | Methods of controlling insects |
| US9474279B2 (en) | 2012-08-24 | 2016-10-25 | Syngenta Participations Ag | Methods of controlling insects |
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| US20220315570A1 (en) * | 2019-07-01 | 2022-10-06 | Shenyang University Of Chemical Technology | Isoxazoline compounds, their preparation methods and use |
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2020
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Also Published As
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|---|---|
| CN112174905B (zh) | 2023-10-20 |
| CN114026076A (zh) | 2022-02-08 |
| WO2021000867A1 (zh) | 2021-01-07 |
| EP3978482A1 (en) | 2022-04-06 |
| BR112021026509A2 (pt) | 2022-02-15 |
| BR112021026487A2 (pt) | 2022-04-12 |
| EP3978482A4 (en) | 2022-07-06 |
| US20220315570A1 (en) | 2022-10-06 |
| CN114026075A (zh) | 2022-02-08 |
| US20220242835A1 (en) | 2022-08-04 |
| EP3978481A1 (en) | 2022-04-06 |
| WO2021000865A1 (zh) | 2021-01-07 |
| EP3978481A4 (en) | 2022-07-06 |
| CN112174904B (zh) | 2023-08-18 |
| CN112174905A (zh) | 2021-01-05 |
| CN114026076B (zh) | 2023-03-21 |
| CN112174904A (zh) | 2021-01-05 |
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