KR950702973A - 1,2,4-Dithiazolium iodides and their use as pesticides - Google Patents

1,2,4-Dithiazolium iodides and their use as pesticides Download PDF

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KR950702973A
KR950702973A KR1019950700591A KR19950700591A KR950702973A KR 950702973 A KR950702973 A KR 950702973A KR 1019950700591 A KR1019950700591 A KR 1019950700591A KR 19950700591 A KR19950700591 A KR 19950700591A KR 950702973 A KR950702973 A KR 950702973A
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straight
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iodide
dithiazolium
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하이네만 울리히
데네 하인쯔-빌헬름
에어델렌 크리스토프
바헨도르프-노이만 울리케
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로이터, 슈마허
바이엘 악티엔게젤샤프트
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    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D285/00Heterocyclic compounds containing rings having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by groups C07D275/00 - C07D283/00
    • C07D285/01Five-membered rings
    • AHUMAN NECESSITIES
    • A01AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01NPRESERVATION 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
    • A01N43/00Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/72Biocides, 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
    • A01N43/82Biocides, 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 three ring hetero atoms

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Abstract

본 발명은 하기 일반시 (I)의 신규한 1,2,4-디티아졸륨 요오다이드, 그의 제조방법, 해충을 구제하기 위한 그의 용도 및 신규한 출발물질에 관한 것이다.The present invention relates to novel 1,2,4-dithiazolium iodide of the following general time (I), a process for its preparation, its use for controlling pests and novel starting materials.

상기식에서, R1및 R2는 명세서에서 정의한 바와 같다.Wherein R 1 and R 2 are as defined in the specification.

일반식 (I)의 신규한 1,2,4-디티아졸륨 요오다이드는 공지된 방법에 의해, 예를들어 적합한 3-알킬티오-1,2,4-티티아졸륨 요오다이드를 적합한 아민과 반응시켜 제조할 수 있다. 이때 사용된 3-알킬티오-1,2,4-디티아졸륨 요오다이드는 마찬가지로 신규하며, 3-디메틸아미노-1,2,4-디티아졸린-5-티온 및 알킬 요오다이드로 부터 제조할 수 있다.The novel 1,2,4-dithiazolium iodides of general formula (I) can be prepared by known methods, for example suitable 3-alkylthio-1,2,4-thithiazolium iodide, with suitable amines. It can be prepared by reaction with. The 3-alkylthio-1,2,4-dithiazolium iodide used here is likewise novel and can be prepared from 3-dimethylamino-1,2,4-dithiazoline-5-thione and alkyl iodide. Can be.

Description

1,2,4-디티아졸륨 요오다이드 및 농약으로서의 그의 용도(1,2,4-Dithiazolium iodides and their use as pesticides)1,2,4-Dithiazolium iodides and their use as pesticides

본 내용은 요부공개 건이므로 전문내용을 수록하지 않았음Since this is an open matter, no full text was included.

Claims (12)

일반식 (I)의 1,2,4-디티아졸륨 요오다이드.1,2,4-Dithiazolium iodide of formula (I). 상기식에서, R1은 알킬 또는 아릴을 나타내고, R2는 알킬을 나타내기나, R1및 R2는 이들이 결합된 질소원자와 함께는 임의로 추가의 헤테로원자를 함유할 수 있는 임의로 치환된 헤테로사이클을 나타낸다.Wherein R 1 represents alkyl or aryl and R 2 represents alkyl, but R 1 and R 2 together with the nitrogen atom to which they are attached optionally represent an optionally substituted heterocycle which may contain additional heteroatoms. Indicates. 제1항에 있어서, R1이 탄소수 1 내지 8의 직쇄 또는 측쇄 알킬을 나타내거나, 동일하거나 상이한 치환체에 의해 임의로 일치환되거나 다치화니되는 탄소수 6 내지 10의 아릴을 나타내며, 여기에서 각 경우에 적합한 치환체는 할로겐, 시아노, 니트로, 각 경우에 1 내지 4개의 탄소원자를 가지며 각 경우에 직쇄 또는 측쇄인 알킬, 알콕시, 알킬티오, 알켈설포닐 또는 알킬설포닐, 각 경우에 1 내지 4개의 탄소 원자 및 1 내지 9개의 동일하거나 상이한 할로겐 원자를 가지며 각 경우에 직쇄 또는 측쇄인 할로게노알킬, 할로게노알콕시, 할로게노알킬티오, 할로게노알킬설피닐 또는 할로게노알킬설포닐, 각 경우에 개개 알킬 부위에 1 내지 4개의 탄소원자를 가지며 각 경우에 직쇄 또는 측쇄인 알콕시카보닐 또는 알콕시이미노알킬, 또는 할로겐, 각 경우에 1 내지 4개의 탄소 원자 및, 경우에 따라 1 내지 9개의 동일하거나 상이한 할로겐 원자를 갖는 직쇄 또는 측쇄 알킬, 직쇄 또는 측쇄 알콕시, 직쇄 또는 측쇄 할로케노알킬 및 직쇄 또는 측쇄 할로게노알콕시로 구성된 동일하거나 상이한 치환체에 의해 임의로 일치환되거나 다치환되는 페닐이고, R2는 탄소수 1 내지 8의 직쇄 또는 측쇄 알킬을 나타내거나, R1및 R2는 이들이 결합된 질소 원자와 함께 추가의 헤테로 원자를 임의로 함유할 수 있고 동일하거나 상이한 치환체(여기에서 적합한 치환체는 할로겐, 각 경우에 1 내지 4개의 탄소원자를 가지며 각 경우에 직쇄 또는 측쇄인 알킬 또는 알콕시, 또는 각 경우에 1 내지 4개의 탄소원자 및 1 내지 9개의 동일하거나 상이한 할로겐 원자를 가지며 각 경우에 직쇄 또는 측쇄인 할로게노알킬 또는 할로게노알콕시이다)에 의해 임의로 일치환되거나 다치환되는 포화된 5- 내지 7-원 헤테로사이클을 나타내는 일반식 (I)의 1,2,4-디티아졸륨 요오다이드.2. The aryl of claim 1, wherein R 1 represents a straight or branched chain alkyl of 1 to 8 carbon atoms, or an aryl having 6 to 10 carbon atoms optionally monosubstituted or substituted by the same or different substituents. Substituents are halogen, cyano, nitro, in each case having 1 to 4 carbon atoms and in each case straight or branched alkyl, alkoxy, alkylthio, alksulsulfonyl or alkylsulfonyl, in each case 1 to 4 carbon atoms And halogen or alkyl, halogenoalkoxy, halogenoalkylthio, halogenoalkylsulfinyl or halogenoalkylsulfonyl, in each case a straight chain or branched chain having 1 to 9 identical or different halogen atoms; Alkoxycarbonyl or alkoxyiminoalkyl having 1 to 4 carbon atoms in each case, straight or branched, or halogen in each case To the same or different substituents consisting of straight or branched chain alkyl, straight or branched chain alkoxy, straight or branched chain halogenoalkyl and straight or branched chain halogenoalkoxy having 4 carbon atoms and optionally 1 to 9 identical or different halogen atoms Phenyl optionally monosubstituted or polysubstituted, R 2 represents straight or branched chain alkyl of 1 to 8 carbon atoms, or R 1 and R 2 may optionally contain additional hetero atoms together with the nitrogen atom to which they are attached; Same or different substituents (where suitable substituents are halogen, in each case alkyl or alkoxy having 1 to 4 carbon atoms and in each case are straight or branched chains, or in each case 1 to 4 carbon atoms and 1 to 9 identical or Halogenoalkyl or halogenoalkoxy having a different halogen atom and in each case straight or branched chain C) to the yaw Id Oda optionally monosubstituted or multi-1,2,4-triazolo dt cerium represented by the general formula (I) represents a saturated 5- to 7-membered heterocycle which is optionally substituted. 제1항에 있어서, R1이 탄소수 1 내지 6의 직쇄 또는 측쇄 알킬을 나타내거나, 동일하거나 상이한 치환체(여기에서 각 경우에 적합한 치환체는 할로겐, 시아노, 니트로, 각 경우에 1 내지 4개의 탄소원자를 가지며 각 경우에 직쇄 또는 측쇄인 알킬, 알콕시, 알킬티오, 알킬설피닐 또는 알킬설포닐, 또는 각 경우에 1 내지 4개의 탄소 원자 및 1 내지 9개의 동일하거나 상이한 할로겐 원자를 가지며 각 경우에 직쇄 또는 측쇄인 할로게노알킬, 할로게노알콕시, 할로게노알킬티오, 할로게노알킬설피닐 또는 할로게노알킬설포닐이다) 에 의해 임의로 일치환 내지 삼치환되는 페닐을 나타내고, R2는 탄소수 1 내지 6의 직쇄 또는 측쇄 알킬을 나타내거나, R1및 R2는 이들이 결합된 질소 원자와 함께 추가의 헤테로 원자를 임의로 함유할 수 있고 동일하거나 상이한 치환체(여기에서 적합한 치환체는 할로겐, 또는 각 경우에 1 내지 4개의 탄소원자를 가지며 각 경우에 직쇄 또는 측쇄인 알킬 또는 알콕시이다)에 의해 임의로 일치환 내지 사치환되는 포화된 5- 내지 7- 원 헤테로사이클을 나타내는 일반식(I)의 1,2,4-디티아졸륨 요오다이드.The compound of claim 1, wherein R 1 represents straight or branched chain alkyl of 1 to 6 carbon atoms, or the same or different substituents (where suitable substituents in each case are halogen, cyano, nitro, in each case 1 to 4 carbon sources) Alkyl, alkoxy, alkylthio, alkylsulfinyl or alkylsulfonyl in each case or straight or branched chain, or in each case 1 to 4 carbon atoms and 1 to 9 identical or different halogen atoms and in each case straight chain Or phenyl optionally mono- to trisubstituted by branched halogenoalkyl, halogenoalkoxy, halogenoalkylthio, halogenoalkylsulfinyl or halogenoalkylsulfonyl), and R 2 has 1 to 6 carbon atoms. May represent straight or branched alkyl, or R 1 and R 2 may optionally contain additional hetero atoms together with the nitrogen atom to which they are attached and may be the same or different; Saturated 5- to 7-membered heteroaryl optionally substituted monosubstituted to tetrasubstituted by a substituent, wherein suitable substituents are halogen or in each case are alkyl or alkoxy having 1 to 4 carbon atoms and in each case are straight or branched chains. 1,2,4-Dithiazolium iodide of general formula (I) which shows a cycle. 제1항에 있어서, R1이 탄소수 1 내지 4의 직쇄 또는 측쇄 알킬을 나타내거나, 동일하거나 상이한 치환체(여기에서 각 경우에 적합한 치환제는 플루오로, 클로로, 브로모, 시아노, 니트로, 메틸, 에틸, n- 또는 i-프로필, n-, i-, s- 또는 t-부틸, 메톡시, 에톡시 n- 또는 i-프로폭시, n, i-, s- 또는 t-부록시, 트리플루오로메틸, 디플루오로메틸, 트리플루오로메톡시 또는 디플루오로메톡시이다)에 의해 임의로 일치환되거나 이치환되는 페닐을 나타내고, R2는 탄소수 1 내지 4의 직쇄 또는 측쇄 알킬을 나타내거나, R1및 R2는 이들이 결합된 질소 원자와 함께 임의로 일치환되거나 이치환되는 피롤리디닐, 피페리디닐, 피하이드로아제피닐 또는 모르폴리닐 래디칼을 나다내며, 여기에서 각 경우에 적합한 치환체는 클로로, 메틸, 에틸, 메톡시 또는 에톡시인 일반식 (I)의 1,2,4-디티아졸륨 요오다이드.The compound of claim 1, wherein R 1 represents straight or branched chain alkyl of 1 to 4 carbon atoms, or the same or different substituents (where suitable substituents in each case are fluoro, chloro, bromo, cyano, nitro, methyl , Ethyl, n- or i-propyl, n-, i-, s- or t-butyl, methoxy, ethoxy n- or i-propoxy, n, i-, s- or t-buroxy, tri Phenyl optionally mono- or di-substituted by fluoromethyl, difluoromethyl, trifluoromethoxy or difluoromethoxy), R 2 represents straight or branched chain alkyl of 1 to 4 carbon atoms, or R 1 And R 2 exits pyrrolidinyl, piperidinyl, pihydroazinyl or morpholinyl radicals optionally substituted or substituted with the nitrogen atom to which they are attached, wherein a suitable substituent in each case is chloro, methyl , Ethyl, methoxy or ethoxy 1,2,4-Dithiazolium iodide of I). 구조식 (II)의 3-알킬티오-1,2,4-디티아졸륨 요오다이드를, 임의로 희석제의 존재하에서 일반식 (III)의 아민과 반응시킴을 특징으로 하여, 일반식 (I)의 1,2,4-디티아졸륨 요오다이드를 제조하는 방법.3-alkylthio-1,2,4-dithiazolium iodide of formula (II) is characterized by reacting with an amine of formula (III), optionally in the presence of a diluent, Method for preparing 1,2,4-dithiazolium iodide. 상기식에서, R1은 알킬 또는 아릴을 나타내고, R2는 알킬을 나타내거나, R1및, R2는 이들이 결합된 질소원자와 함께 임의로 추가의 헤테로원자를 함유할 수 있는 임의로 치환된 헤테로사이클을 나타내며, R은 알킬을 나타낸다.Wherein R 1 represents alkyl or aryl, R 2 represents alkyl, or R 1 and R 2 represent an optionally substituted heterocycle which may optionally contain additional heteroatoms with the nitrogen atom to which they are attached And R represents alkyl. 제1항 또는 5항에 따르는 일반식 (I)의 1,2,4-디티아졸륨 요오다이드를 적어도 하나 함유함을 특징으로 하는 농약.A pesticide, characterized in that it contains at least one 1,2,4-dithiazolium iodide of the general formula (I) according to claim 1. 해충을 구제하기 위한 제1항 또는 5항에 따르는 일반식 (I)의 1,2,4-디티아졸륨 요오다이드의 용도.Use of 1,2,4-dithiazolium iodide of formula (I) according to claim 1 or 5 for controlling pests. 제1항 또는 5항에 따르는 일반식 (I)의 1,2,4-디티아졸륨 요오다이드를 해충 및/또는 그들의 서식지에 작용시킴을 특징으로 하는 해충 구제 방법.A pest control method, characterized in that 1,2,4-dithiazolium iodide of formula (I) according to claim 1 or 5 is acted on pests and / or their habitats. 제1항 또는 5항에 따르는 일반식 (I)의 1,2,4-디티아졸륨 요오다이드를 해충 및/또는 계면 활성제와 혼합함을 특징으로 하는 농약의 제조방법.A process for producing pesticides, characterized in that 1,2,4-dithiazolium iodide of formula (I) according to claim 1 or 5 is mixed with pests and / or surfactants. 제7항에 있어서, 곤충, 거미 및 진균을 구제하기 위한 일반식 (I)의 1,2,4-디티아졸륨 요오다이드의 용도.Use of 1,2,4-dithiazolium iodide of formula (I) according to claim 7, for controlling insects, spiders and fungi. 구조식 (II)의 3-알킬티오-1,2,4-디티아졸륨 요오다이드.3-alkylthio-1,2,4-dithiazolium iodide of formula (II). 상기식에서, R은 알킬을 나타낸다.Wherein R represents alkyl. 구조식(IV)의 3-디메틸아미노-1,2-4-디티아졸린-5-티온을, 임의로 희석제의 존재하에서 일반식(V)의 알킬 요오다이드와 반응시킴을 특징으로 하여, 구조식 (II)의 3-알킬티오-1,2,4-디티아졸륨 요오다이드를 제조하는 방법.3-dimethylamino-1,2-4-dithiazoline-5-thione of formula (IV) is reacted with alkyl iodide of formula (V), optionally in the presence of a diluent, A process for preparing 3-alkylthio-1,2,4-dithiazolium iodide of II). 상기식에서, R은 알킬을 나타낸다.Wherein R represents alkyl. ※ 참고사항 : 최초출원 내용에 의하여 공개하는 것임.※ Note: The disclosure is based on the initial application.
KR1019950700591A 1992-08-21 1993-08-09 1,2,4-Dithiazolium iodides and their use as pesticides KR950702973A (en)

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DE4227751A DE4227751A1 (en) 1992-08-21 1992-08-21 1,2,4-dithiazolium iodides and new starting compounds
DEP4227751.5 1992-08-21
PCT/EP1993/002114 WO1994004517A1 (en) 1992-08-21 1993-08-09 1,2,4-dithiazolium iodides and their use as pesticides

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HU9500523D0 (en) 1995-04-28
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AU4947093A (en) 1994-03-15
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JPH08500581A (en) 1996-01-23
RU95109103A (en) 1996-12-20

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