KR102267724B1 - Novel compounds containing pentafluorosulfanyl group and insecticide composition comprising same - Google Patents

Novel compounds containing pentafluorosulfanyl group and insecticide composition comprising same Download PDF

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KR102267724B1
KR102267724B1 KR1020190173461A KR20190173461A KR102267724B1 KR 102267724 B1 KR102267724 B1 KR 102267724B1 KR 1020190173461 A KR1020190173461 A KR 1020190173461A KR 20190173461 A KR20190173461 A KR 20190173461A KR 102267724 B1 KR102267724 B1 KR 102267724B1
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aryl
heteroaryl
haloc
compound
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박성준
임환정
김재곤
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한국화학연구원
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Abstract

The present invention relates to a compound containing a novel pentafluorosulfanyl group, a pesticide composition containing the same, and a method for controlling pests using the same, wherein a pentafluorosulfanyl-substituted compound according to the present invention is useful for controlling various pests of insects, particularly moths such as Plutella xylostella, Spodoptera litura and the like.

Description

펜타플루오로설파닐 기를 포함하는 화합물 및 이를 함유하는 살충제 조성물{NOVEL COMPOUNDS CONTAINING PENTAFLUOROSULFANYL GROUP AND INSECTICIDE COMPOSITION COMPRISING SAME}Compounds comprising pentafluorosulfanyl groups and pesticidal compositions containing them {NOVEL COMPOUNDS CONTAINING PENTAFLUOROSULFANYL GROUP AND INSECTICIDE COMPOSITION COMPRISING SAME}

곤충류의 다양한 해충류에 살충 효과를 가지는 신규 화합물 및 이를 함유하는 살충제 조성물에 관한 것이다.It relates to a novel compound having an insecticidal effect on various pests of insects and an insecticide composition containing the same.

종래에 많이 사용되었던 살충제로서 카바메이트계 살충제 또는 유기인계 살충제를 들 수 있는데, 이들 살충제는 아세틸콜린에스테라제를 저해하여 효과를 발휘한다. 그런데 이들 살충제를 오래 사용하면서 저항성을 보이는 해충이 나타나 새로운 작용기작의 살충제 개발이 필요하게 되었고, 칼슘이온 통로인 리아노딘(ryanodine, Ry) 수용체 및 염소이온 통로인 γ-아미노부티르산(γ-aminobutyric acid, GABA) 수용체가 해충을 방제하기 위한 새로운 표적으로 대두되었다.Carbamate-based insecticides or organophosphorus insecticides can be cited as insecticides that have been widely used in the past, and these insecticides exert their effect by inhibiting acetylcholinesterase. However, the long-term use of these insecticides resulted in the emergence of resistant pests, which required the development of insecticides with a new mechanism of action. The calcium ion channel ryanodine (Ry) receptor and the chlorine ion channel γ-aminobutyric acid (γ-aminobutyric acid) , GABA) receptors have emerged as new targets for controlling pests.

칼슘의 항상성은 특히 근육 수축에 중요한 역할을 하기 때문에, 리아노딘 수용체에 결합하는 살충제는, 해충의 섭식을 저해하고 혼수 상태나 마비를 유발하여 사망에 이르게 한다.Because calcium homeostasis plays a particularly important role in muscle contraction, insecticides that bind to ryanodine receptors inhibit pest feeding and cause coma or paralysis, leading to death.

현재까지 리아노딘 수용체에 결합하는 살충제로 시판된 것은 니혼 노햐쿠(Nihon Nohyaku)사가 발견하고 바이엘 크롭 사이언스(Bayer Crop Science)사가 공동 개발한 플루벤다이아미드(flubendiamide, PhoenixTM, TakumiTM, EP 1380209 A1)와 듀퐁(Du Pont)사가 개발한 안트라닐아미드(anthranilamide) 구조의 클로란트라닐리프롤(chlorantraniliprole, RynaxypyrTM, WO 01/070671) 및 사이안트라닐리프롤(cyantraniliprole, CyazypyrTM, WO 04/067528)이 있다.So far, commercially available insecticides that bind to ryanodine receptors have been discovered by Nihon Nohyaku and co-developed by Bayer Crop Science (flubendiamide, Phoenix TM , Takumi TM , EP 1380209 A1). ) and Du Pont's anthranilamide structure chlorantraniliprole (Rynaxypyr TM , WO 01/070671) and cyantraniliprole (cyantraniliprole, Cyazypyr TM , WO 04/) 067528).

이들 화합물은 리아노딘 수용체에 결합하여 칼슘 이온통로를 교란시킴으로써 살충 효과를 나타내는 물질로서, 특히 나방류에 대한 살충작용이 강력하다고 알려져 있다.These compounds bind to ryanodine receptors and disrupt calcium ion channels, thereby exhibiting insecticidal effects. In particular, they are known to have strong insecticidal action against moths.

바이엘(Bayer)사와 듀퐁(Du Pont)사를 포함하여 신젠타(Syngenta)사, 스미토모(Sumitomo)사, 이시하가라 산교 카이샤(Ishihara Sangyo Kaisha)사, 닛산(Nissan)사 등의 회사가 이들의 다양한 유도체를 개발하여 100여 개의 특허가 출원되었으나, 아직까지 시판되는 것은 플루벤다이아미드, 클로란트라닐리프롤 및 사이안트라닐리프롤의 세 종에 불과하다.Companies such as Bayer and Du Pont, Syngenta, Sumitomo, Ishihara Sangyo Kaisha, and Nissan Although more than 100 patents have been applied for developing derivatives, only three types of flubendiamide, chlorantraniliprole and cyantraniliprole are on the market so far.

한편, GABA 수용체 저해제는 해충의 신경전달물질인 GABA 수용체를 억제(차단)해 신경계의 염소이온 이동을 차단하고, 이로 인해 중추신경계 통제 불능상태로 이어져 결국 사망에 이르게 한다.On the other hand, GABA receptor inhibitors block (block) the GABA receptor, a neurotransmitter of pests, and block the movement of chlorine ions in the nervous system, which leads to a state of central nervous system control failure, which ultimately leads to death.

GABA 수용체를 억제하는 살충제로 대표적인 것은 페닐피라졸 성분 계열의 피프로닐(fipronil)이다. 이는 개나 고양이 등 애완동물에서 기생하는 벼룩이나 집안의 바퀴벌레 퇴치용으로 사용되거나, 닭 등의 대량사육시 닭 진드기용 살충약제로서 사용된 바 있다. 이는 해충의 GABA 수용체를 억제해 신경계의 염소이온의 이동을 차단함으로써 중추신경계를 통제불능상태로 만들어 진드기와 벼룩 같은 해충을 살멸하는 작용을 하며, 피부의 지방과 털의 모낭에 저장되어 피모에 작용함으로써 장기간에 걸친 살충 효과를 나타낸다.A representative insecticide that inhibits GABA receptors is fipronil, a phenylpyrazole component. It has been used as an insecticide for chicken mites in the case of mass breeding of chickens or used for repelling domestic cockroaches or fleas parasitic on pets such as dogs and cats. It inhibits the GABA receptors of pests and blocks the movement of chlorine ions in the nervous system, making the central nervous system out of control and killing pests such as mites and fleas. By doing so, it exhibits a long-term insecticidal effect.

최근에는 살충제 농약의 개발시 인축 및 환경에 대한 안전성뿐만 아니라 익충인 꿀벌에 대한 안전성도 중요시되고 있다. 듀퐁사에서 개발한 클로란트라닐리프롤은 꿀벌 급성접촉독성이 >4μg/bee(LD50)에 불과하여, 이보다 더 안전한 살충제 개발이 필요한 상황이다. 한편, 살충제 개발에 있어 꿀벌 급성접촉독성과 함께 고려해야할 것이 토양 잔류에 대한 반감기이다. 클로란트라닐리프롤의 토양 중 반감기는 약 180일 정도로 토양에 오랫동안 잔류하여 환경에 대한 위험요소를 안고 있다. 꿀벌에 대한 안정성과 동시에, 토양 잔류 기간도 짧아 환경에 더욱 안전한 살충제 개발이 필요하다.Recently, in the development of pesticides and pesticides, safety for livestock and the environment as well as safety for bees, which are beneficial insects, is considered as important. Chlorantraniliprole developed by DuPont has an acute contact toxicity of >4μg/bee (LD 50 ) to bees, so it is necessary to develop a safer insecticide. On the other hand, in the development of pesticides, the half-life for soil residue should be considered along with the acute contact toxicity of bees. The half-life of chlorantraniliprole in the soil is about 180 days, so it remains in the soil for a long time and poses a risk to the environment. At the same time as stability to bees, the soil residence period is short, so it is necessary to develop an insecticide that is safer for the environment.

KRUS 10-2011-0039370 10-2011-0039370 AA EP 3 392 236 A1EP 3 392 236 A1

본 발명의 일 목적은 다양한 해충에 대한 살충 활성을 보이는 동시에 익충에 안전하고, 토양 잔류 기간이 짧은 살충제 조성물의 활성 성분으로 사용 가능한 신규 화합물, 이의 수화물, 이의 용매화물 또는 이의 염을 제공하는 것이다.It is an object of the present invention to provide a novel compound, a hydrate thereof, a solvate thereof, or a salt thereof that can be used as an active ingredient of an insecticidal composition that is safe for beneficial insects and has a short soil retention period while exhibiting insecticidal activity against various pests.

본 발명의 다른 목적은 상기 화합물, 이의 수화물, 이의 용매화물 또는 이의 염을 활성 성분으로 함유하는 살충제 조성물을 제공하는 것이다.Another object of the present invention is to provide a pesticide composition comprising the compound, a hydrate thereof, a solvate thereof or a salt thereof as an active ingredient.

본 발명의 또 다른 목적은 상기 살충제 조성물을 농작물 또는 이의 서식지에 처리하여 해충을 방제하는 방법을 제공하는 것이다.Another object of the present invention is to provide a method for controlling pests by treating crops or their habitats with the pesticide composition.

상기 목적을 달성하기 위하여, 본 발명은 하기 화학식 1의 화합물, 이의 수화물, 이의 용매화물 또는 이의 염을 제공하며, 하기 화학식 1의 화합물은 펜타플루오로설파닐(pentafluorosulfanyl, -SF5) 기를 포함하는 메타-다이아마이드 화합물이다:In order to achieve the above object, the present invention provides a compound of Formula 1, a hydrate thereof, a solvate thereof or a salt thereof, wherein the compound of Formula 1 includes a pentafluorosulfanyl (-SF 5 ) group. It is a meta-diamide compound:

[화학식 1][Formula 1]

Figure 112019133198795-pat00001
Figure 112019133198795-pat00001

상기 화학식 1에서,In Formula 1,

L은

Figure 112019133198795-pat00002
또는
Figure 112019133198795-pat00003
이고;L is
Figure 112019133198795-pat00002
or
Figure 112019133198795-pat00003
ego;

R은 C1-10알킬, C3-10사이클로알킬, C6-20아릴, C3-20헤테로아릴 또는 -O-Ra 이고;R is C 1-10 alkyl, C 3-10 cycloalkyl, C 6-20 aryl, C 3-20 heteroaryl or —OR a ;

Ra는 C1-10알킬, C3-10사이클로알킬, C6-20아릴 또는 C3-20헤테로아릴이고;R a is C 1-10 alkyl, C 3-10 cycloalkyl, C 6-20 aryl or C 3-20 heteroaryl;

상기 R 및 Ra의 알킬, 사이클로알킬, 아릴 및 헤테로아릴은 할로겐, C1-10알킬, C1-10알콕시, 할로C1-10알킬, 할로C1-10알콕시, C6-20아릴, C3-20헤테로아릴, 니트로 및 이들의 조합으로부터 선택되는 하나 이상으로 더 치환될 수 있고;Alkyl, cycloalkyl, aryl and heteroaryl of R and R a are halogen, C 1-10 alkyl, C 1-10 alkoxy, haloC 1-10 alkyl, haloC 1-10 alkoxy, C 6-20 aryl, may be further substituted with one or more selected from C 3-20 heteroaryl, nitro, and combinations thereof;

R1 및 R2는 각각 독립적으로 수소 또는 C1-10알킬이고;R 1 and R 2 are each independently hydrogen or C 1-10 alkyl;

R3는 할로겐, C1-10알킬, C3-10사이클로알킬, C3-10사이클로알킬C1-10알킬, C1-10알콕시, 할로C1-10알킬, 할로C1-10알콕시, 시아노, C1-10알킬티오, C6-20아릴, C1-10알킬C6-20아릴, C6-20아릴옥시, C6-20아릴티오, C6-20아릴C1-10알킬 또는 -SF5이며;R 3 is halogen, C 1-10 alkyl, C 3-10 cycloalkyl, C 3-10 cycloalkylC 1-10 alkyl, C 1-10 alkoxy, haloC 1-10 alkyl, haloC 1-10 alkoxy, Cyano, C 1-10 Alkylthio , C 6-20 Aryl, C 1-10 AlkylC 6-20 Aryl, C 6-20 Aryloxy, C 6-20 Arylthio, C 6-20 ArylC 1-10 alkyl or -SF 5 ;

m은 0 내지 4의 정수이고, m이 2 이상의 정수인 경우 R3는 동일하거나 상이할 수 있고;m is an integer from 0 to 4, and when m is an integer of 2 or more, R 3 may be the same or different;

상기 헤테로아릴은 각각 독립적으로 질소, 산소 및 황으로부터 선택된 하나 이상의 헤테로원자를 포함한다.The heteroaryls each independently include one or more heteroatoms selected from nitrogen, oxygen and sulfur.

또한, 본 발명은 상기 화학식 1의 화합물, 이의 수화물, 이의 용매화물 또는 이의 염을 활성 성분으로 함유하는 살충제 조성물을 제공한다.In addition, the present invention provides a pesticide composition comprising the compound of Formula 1, a hydrate thereof, a solvate thereof, or a salt thereof as an active ingredient.

또한, 본 발명은 상기 살충제 조성물을 농작물 또는 이의 서식지에 처리하여 해충을 방제하는 방법을 제공한다.In addition, the present invention provides a method for controlling pests by treating the pesticide composition on crops or habitats thereof.

화학식 1의 펜타플루오로설파닐-치환 메타-다이아마이드 화합물, 이의 수화물, 이의 용매화물 또는 이의 염은 신규한 화합물로서, 이를 활성 성분으로 함유하는 살충제 조성물은 다양한 해충류, 특히 배추 좀나방, 담배거세미나방 등의 나방류에 대해 우수한 살충 효과를 보이면서도 익충인 꿀벌에 안전하며, 토양 잔류 기간이 짧아 친환경적이다.The pentafluorosulfanyl-substituted meta-diamid compound of Formula 1, its hydrate, its solvate, or its salt is a novel compound, and the pesticide composition containing it as an active ingredient is suitable for use in various pests, particularly Chinese cabbage moth, tobacco. It shows an excellent insecticidal effect against moths such as spider moths, while being safe for bees, which are beneficial insects, and is eco-friendly because of its short soil retention period.

이하, 본 발명에 대하여 보다 구체적으로 설명한다. 이 때 사용되는 기술 용어 및 과학 용어에 있어서 다른 정의가 없다면, 이 발명이 속하는 기술 분야에서 통상의 지식을 가진 자가 통상적으로 이해하고 있는 의미를 가지며, 하기의 설명에서 본 발명의 요지를 불필요하게 흐릴 수 있는 공지 기능 및 구성에 대한 설명은 생략한다.Hereinafter, the present invention will be described in more detail. If there is no other definition in the technical and scientific terms used at this time, it has the meaning commonly understood by those of ordinary skill in the art to which this invention belongs, and may unnecessarily obscure the subject matter of the present invention in the following description. Descriptions of possible known functions and configurations will be omitted.

본 명세서에서 사용된 하기 용어들은 다음과 같이 정의되나, 이는 단지 예시적인 것에 불과하며, 본 발명, 출원 또는 용도를 한정하려는 것은 아니다.The following terms used in this specification are defined as follows, but these are merely exemplary and are not intended to limit the present invention, application or use.

본 명세서의 용어 "치환기(substituent)", "라디칼(radical)", "기(group)", "모이어티(moiety)", 및 "절편(fragment)"은 서로 바꾸어 사용할 수 있다.As used herein, the terms “substituent”, “radical”, “group”, “moiety”, and “fragment” may be used interchangeably.

본 명세서의 용어 "CA-B"는 "탄소수가 A 이상이고 B 이하"인 것을 의미한다.The term "C AB " as used herein means "the number of carbon atoms is greater than or equal to A and less than or equal to B".

본 명세서의 용어 "알킬"은 탄소 및 수소 원자만으로 구성된 1가의 직쇄 또는 분쇄 포화 탄화수소 라디칼을 의미하는 것으로, 1 내지 10개의 탄소원자, 1 내지 7개의 탄소원자, 1 내지 5개의 탄소원자 또는 1 내지 4개의 탄소원자를 가질 수 있다. 이러한 알킬 라디칼의 예는 메틸, 에틸, 프로필, 이소프로필, 부틸, 이소부틸, t-부틸, 펜틸, 헥실 등을 포함하지만 이에 한정되지는 않는다.As used herein, the term “alkyl” refers to a monovalent straight-chain or branched saturated hydrocarbon radical composed only of carbon and hydrogen atoms, and has 1 to 10 carbon atoms, 1 to 7 carbon atoms, 1 to 5 carbon atoms, or 1 to It may have 4 carbon atoms. Examples of such alkyl radicals include, but are not limited to, methyl, ethyl, propyl, isopropyl, butyl, isobutyl, t-butyl, pentyl, hexyl, and the like.

본 명세서의 용어 "사이클로알킬"은 하나 이상의 고리로 구성된 1가의 포화 카보사이클릭 라디칼로, 3 내지 10개의 탄소원자 바람직하게는 3 내지 7개의 탄소원자를 가질 수 있다. 구체적인 예로는 시클로프로필, 시클로부틸, 시클로펜틸, 시클로헥실 등을 들 수 있으나, 이에 한정되지는 않는다.As used herein, the term “cycloalkyl” is a monovalent saturated carbocyclic radical composed of one or more rings, and may have 3 to 10 carbon atoms, preferably 3 to 7 carbon atoms. Specific examples include, but are not limited to, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, and the like.

본 명세서의 용어 "아릴"은 하나의 수소 제거에 의해서 방향족 탄화수소로부터 유도된 유기 라디칼로, 각 고리에 적절하게는 4 내지 7개, 바람직하게는 5 또는 6개의 고리원자를 포함하는 단일 또는 융합고리계를 포함하며, 다수개의 아릴이 단일결합으로 연결되어 있는 형태까지 포함한다. 구체적인 예로 페닐, 나프틸, 비페닐, 안트릴, 인데닐, 플루오레닐 등을 포함하지만, 이에 한정되지는 않는다.As used herein, the term "aryl" is an organic radical derived from an aromatic hydrocarbon by removal of one hydrogen, suitably a single or fused ring containing 4 to 7, preferably 5 or 6 ring atoms in each ring. It includes a system, and includes a form in which a plurality of aryls are connected by a single bond. Specific examples include, but are not limited to, phenyl, naphthyl, biphenyl, anthryl, indenyl, fluorenyl, and the like.

본 명세서의 용어 "헤테로아릴"은 방향족 고리 골격 원자로서 N, O 및 S로부터 선택되는 1 내지 4개의 헤테로원자를 포함하고, 나머지 방향족 고리 골격 원자가 탄소인 아릴 그룹을 의미하는 것으로, 5 내지 6원 단환 헤테로아릴, 및 하나 이상의 벤젠환과 축합된 다환식 헤테로아릴이며, 부분적으로 포화될 수도 있다. 또한, 본 명세서에서의 헤테로아릴은 하나 이상의 헤테로아릴이 단일결합으로 연결된 형태도 포함한다. 본 발명의

Figure 112019133198795-pat00004
도 헤테로아릴에 포함된다. 상기 헤테로아릴기의 예는, 피롤릴, 퀴놀릴, 이소퀴놀릴, 카바졸릴, 피리딜, 피리미디닐, 옥사졸릴, 티아졸릴, 이소티아졸릴, 피라졸릴, 티아디아졸릴, 트리아졸릴, 이미다졸릴, 벤조이미다졸릴, 이속사졸릴, 벤조옥사졸릴, 벤조이속사졸릴, 벤조티아졸릴, 벤조이소티아졸릴, 티오펜일, 벤조티오펜일, 퓨릴, 벤조퓨란일, 다이벤조퓨란일, 다이벤조티오펜일,
Figure 112019133198795-pat00005
등을 포함하지만, 이에 한정되지는 않는다.As used herein, the term "heteroaryl" refers to an aryl group containing 1 to 4 heteroatoms selected from N, O and S as an aromatic ring skeleton atom, and the remaining aromatic ring skeleton atoms are carbon, and 5 to 6 membered. monocyclic heteroaryl, and polycyclic heteroaryl condensed with one or more benzene rings, which may be partially saturated. In addition, heteroaryl in the present specification includes a form in which one or more heteroaryls are connected by a single bond. of the present invention
Figure 112019133198795-pat00004
Also included in heteroaryl. Examples of the heteroaryl group include pyrrolyl, quinolyl, isoquinolyl, carbazolyl, pyridyl, pyrimidinyl, oxazolyl, thiazolyl, isothiazolyl, pyrazolyl, thiadiazolyl, triazolyl, imida Zolyl, benzoimidazolyl, isoxazolyl, benzoxazolyl, benzoisoxazolyl, benzothiazolyl, benzoisothiazolyl, thiophenyl, benzothiophenyl, furyl, benzofuranyl, dibenzofuranyl, dibenzoyl thiophenyl,
Figure 112019133198795-pat00005
and the like.

본 명세서의 용어 "알콕시"는 -O-알킬 라디칼로, 1 내지 10개의 탄소원자, 1 내지 7개의 탄소원자, 1 내지 5개의 탄소원자 또는 1 내지 4개의 탄소원자를 가질 수 있다. 여기서 '알킬'은 상기 정의한 바와 같다. 구체적인 예로는 메톡시, 에톡시, 이소프로폭시, 부톡시, 이소부톡시, t-부톡시 등을 포함되지만 이에 한정되지는 않는다.As used herein, the term "alkoxy" is an -O-alkyl radical, which may have 1 to 10 carbon atoms, 1 to 7 carbon atoms, 1 to 5 carbon atoms, or 1 to 4 carbon atoms. Here, 'alkyl' is as defined above. Specific examples include, but are not limited to, methoxy, ethoxy, isopropoxy, butoxy, isobutoxy, t-butoxy, and the like.

본 명세서의 용어 "할로" 또는 "할로겐"은 할로겐족 원소를 나타내며, 예컨대, 플루오로, 클로로, 브로모 및 요오도를 포함한다.As used herein, the term “halo” or “halogen” refers to a halogen element and includes, for example, fluoro, chloro, bromo and iodo.

본 명세서의 용어 "할로알킬"은 적어도 하나의 할로겐으로 치환된 알킬 라디칼을 의미하는 것으로, 여기서 '알킬'은 상기 정의한 바와 같다. 이러한 할로알킬 라디칼의 예는 플루오로메틸, 트리플루오로메틸, 브로모메틸, 퍼플루오로에틸 등을 포함하지만 이에 한정되지는 않는다.As used herein, the term "haloalkyl" refers to an alkyl radical substituted with at least one halogen, where 'alkyl' is as defined above. Examples of such haloalkyl radicals include, but are not limited to, fluoromethyl, trifluoromethyl, bromomethyl, perfluoroethyl, and the like.

본 명세서의 용어 "할로알콕시"는 적어도 하나의 할로겐으로 치환된 알콕시 라디칼을 의미하는 것으로, 여기서 '알콕시'는 상기 정의한 바와 같다. 이러한 할로알콕시 라디칼의 예는 플루오로메톡시, 트리플루오로메톡시, 트리플루오로에톡시, 퍼플루오로에톡시 등을 포함하지만 이에 한정되지는 않는다.As used herein, the term "haloalkoxy" refers to an alkoxy radical substituted with at least one halogen, where 'alkoxy' is as defined above. Examples of such haloalkoxy radicals include, but are not limited to, fluoromethoxy, trifluoromethoxy, trifluoroethoxy, perfluoroethoxy, and the like.

본 명세서의 용어 "니트로"는 -NO2를 의미하고, "시아노"는 -CN을 의미한다.As used herein, the term "nitro" refers to -NO 2 , and "cyano" refers to -CN.

본 명세서의 용어 "아릴알킬"은 적어도 하나의 아릴로 치환된 알킬 라디칼을 의미하는 것으로, 여기서 '아릴' 및 '알킬'은 상기 정의한 바와 같다. 예를 들어, 아릴알킬 라디칼의 예는 벤질을 포함하지만 이에 한정되지는 않는다.As used herein, the term "arylalkyl" refers to an alkyl radical substituted with at least one aryl, where 'aryl' and 'alkyl' are as defined above. For example, examples of arylalkyl radicals include, but are not limited to, benzyl.

본 명세서의 용어 "알킬아릴"은 적어도 하나의 알킬로 치환된 아릴 라디칼을 의미하는 것으로, 여기서 '알킬' 및 '아릴'은 상기 정의한 바와 같다. 이러한 알킬아릴 라디칼의 예는 톨릴 등을 포함하지만 이에 한정되지는 않는다.As used herein, the term "alkylaryl" refers to an aryl radical substituted with at least one alkyl, where 'alkyl' and 'aryl' are as defined above. Examples of such alkylaryl radicals include, but are not limited to, tolyl and the like.

본 발명자들은 브로플라닐라이드(Broflanilide)의 메타-다이아마이드계 골격 구조를 가지되, 말단에 신규 독작용기(toxophore)로 펜타플루오로설파닐(-SF5) 기를 가지는 메타-다이아마이드 화합물이 우수한 살충 효과가 있음을 발견하고 본 발명을 완성하였다.The present inventors have found that the meta-diaamide compound having a broflanilide meta-diamide-based skeleton structure, but having a pentafluorosulfanyl (-SF 5 ) group as a novel toxophore at the terminal end is excellent. It was discovered that there was an insecticidal effect and completed the present invention.

본 발명의 신규 독작용기인 펜타플루오로설파닐 기의 도입으로 인하여, 우수한 살충 효과이외에도 화학적 및 열적 안정성이 현저히 증대되며, 친유성이 부여되며, 보다 낮은 독성을 나타낼 수 있다.Due to the introduction of the pentafluorosulfanyl group, which is a novel poisoning group of the present invention, chemical and thermal stability are remarkably increased in addition to an excellent insecticidal effect, lipophilicity is imparted, and lower toxicity can be exhibited.

본 발명은 하기 화학식 1로 표시되는 펜타플루오로설파닐(-SF5) 기를 포함하는 화합물, 이의 수화물, 이의 용매화물 또는 이의 염을 제공한다: The present invention provides a compound comprising a pentafluorosulfanyl (-SF 5 ) group represented by the following formula (1), a hydrate thereof, a solvate thereof, or a salt thereof:

[화학식 1][Formula 1]

Figure 112019133198795-pat00006
Figure 112019133198795-pat00006

상기 화학식 1에서,In Formula 1,

L은

Figure 112019133198795-pat00007
또는
Figure 112019133198795-pat00008
이고;L is
Figure 112019133198795-pat00007
or
Figure 112019133198795-pat00008
ego;

R은 C1-10알킬, C3-10사이클로알킬, C6-20아릴, C3-20헤테로아릴 또는 -O-Ra 이고;R is C 1-10 alkyl, C 3-10 cycloalkyl, C 6-20 aryl, C 3-20 heteroaryl or —OR a ;

Ra는 C1-10알킬, C3-10사이클로알킬, C6-20아릴 또는 C3-20헤테로아릴이고;R a is C 1-10 alkyl, C 3-10 cycloalkyl, C 6-20 aryl or C 3-20 heteroaryl;

상기 R 및 Ra의 알킬, 사이클로알킬, 아릴 및 헤테로아릴은 할로겐, C1-10알킬, C1-10알콕시, 할로C1-10알킬, 할로C1-10알콕시, C6-20아릴, C3-20헤테로아릴, 니트로 및 이들의 조합으로부터 선택되는 하나 이상으로 더 치환될 수 있고;Alkyl, cycloalkyl, aryl and heteroaryl of R and R a are halogen, C 1-10 alkyl, C 1-10 alkoxy, haloC 1-10 alkyl, haloC 1-10 alkoxy, C 6-20 aryl, may be further substituted with one or more selected from C 3-20 heteroaryl, nitro, and combinations thereof;

R1 및 R2는 각각 독립적으로 수소 또는 C1-10알킬이고;R 1 and R 2 are each independently hydrogen or C 1-10 alkyl;

R3는 할로겐, C1-10알킬, C3-10사이클로알킬, C3-10사이클로알킬C1-10알킬, C1-10알콕시, 할로C1-10알킬, 할로C1-10알콕시, 시아노, C1-10알킬티오, C6-20아릴, C1-10알킬C6-20아릴, C6-20아릴옥시, C6-20아릴티오, C6-20아릴C1-10알킬 또는 -SF5이며;R 3 is halogen, C 1-10 alkyl, C 3-10 cycloalkyl, C 3-10 cycloalkylC 1-10 alkyl, C 1-10 alkoxy, haloC 1-10 alkyl, haloC 1-10 alkoxy, Cyano, C 1-10 Alkylthio , C 6-20 Aryl, C 1-10 AlkylC 6-20 Aryl, C 6-20 Aryloxy, C 6-20 Arylthio, C 6-20 ArylC 1-10 alkyl or -SF 5 ;

m은 0 내지 4의 정수이고, m이 2 이상의 정수인 경우 R3는 동일하거나 상이할 수 있고;m is an integer from 0 to 4, and when m is an integer of 2 or more, R 3 may be the same or different;

상기 헤테로아릴은 각각 독립적으로 질소, 산소 및 황으로부터 선택된 하나 이상의 헤테로원자를 포함한다.The heteroaryls each independently include one or more heteroatoms selected from nitrogen, oxygen and sulfur.

상기 펜타플루오로설파닐-치환 화합물은 구체적으로 하기 화학식 2 또는 화학식 3으로 표시될 수 있다.The pentafluorosulfanyl-substituted compound may be specifically represented by the following Chemical Formula 2 or Chemical Formula 3.

[화학식 2][Formula 2]

Figure 112019133198795-pat00009
Figure 112019133198795-pat00009

[화학식 3][Formula 3]

Figure 112019133198795-pat00010
Figure 112019133198795-pat00010

상기 화학식 2 및 3에서, R1 및 R2는 상기 화학식 1에서의 정의와 동일하고;In Formulas 2 and 3, R 1 and R 2 are the same as defined in Formula 1;

R11 및 R12는 각각 독립적으로 C1-10알킬, C3-10사이클로알킬, C6-20아릴, C3-20헤테로아릴 또는 -O-Ra 이고;R 11 and R 12 are each independently C 1-10 alkyl, C 3-10 cycloalkyl, C 6-20 aryl, C 3-20 heteroaryl or —OR a ;

Ra는 C1-10알킬, C3-10사이클로알킬 또는 C6-20아릴이고;R a is C 1-10 alkyl, C 3-10 cycloalkyl or C 6-20 aryl;

상기 R11 및 R12의 알킬, 사이클로알킬, 아릴 또는 헤테로아릴, 및 Ra의 알킬, 사이클로알킬 또는 아릴은 할로겐, C1-10알킬, C1-10알콕시, 할로C1-10알킬, 할로C1-10알콕시, C6-20아릴, C3-20헤테로아릴, 니트로, 할로C6-20아릴 및 할로C3-20헤테로아릴로부터 선택되는 하나 이상으로 더 치환될 수 있고;Alkyl, cycloalkyl, aryl or heteroaryl of R 11 and R 12 , and alkyl, cycloalkyl or aryl of R a are halogen, C 1-10 alkyl, C 1-10 alkoxy, haloC 1-10 alkyl, halo may be further substituted with one or more selected from C 1-10 alkoxy, C 6-20 aryl, C 3-20 heteroaryl, nitro, haloC 6-20 aryl and haloC 3-20 heteroaryl;

R3a, R3b 및 R3c는 각각 독립적으로 수소, 할로겐, C1-10알킬, C1-10알콕시, 할로C1-10알킬, 할로C1-10알콕시, 시아노, C1-10알킬티오 또는 -SF5이다.R 3a , R 3b and R 3c are each independently hydrogen, halogen, C 1-10 alkyl, C 1-10 alkoxy, haloC 1-10 alkyl, haloC 1-10 alkoxy, cyano, C 1-10 alkyl thio or -SF 5 .

바람직하게 상기 R11은 C1-7알킬, C6-12아릴, C3-12헤테로아릴 또는 -O-Ra 이고; Ra는 C1-7알킬 또는 C6-12아릴이고; R12는 C1-7알킬, C6-12아릴 또는 C3-12헤테로아릴이고; 상기 R11의 알킬, 아릴 또는 헤테로아릴, Ra의 알킬 또는 아릴, 및 R12의 알킬, 아릴 또는 헤테로아릴은 할로겐, C1-7알킬, C1-7알콕시, 할로C1-7알킬, 할로C1-7알콕시, C6-12아릴, C3-12헤테로아릴, 니트로, 할로C6-12아릴 및 할로C3-12헤테로아릴로부터 선택되는 하나 이상으로 더 치환될 수 있다.preferably said R 11 is C 1-7 alkyl, C 6-12 aryl, C 3-12 heteroaryl or —OR a ; R a is C 1-7 alkyl or C 6-12 aryl; R 12 is C 1-7 alkyl, C 6-12 aryl or C 3-12 heteroaryl; wherein the alkyl, aryl or heteroaryl of R 11 , the alkyl or aryl of R a , and the alkyl, aryl or heteroaryl of R 12 are halogen, C 1-7 alkyl, C 1-7 alkoxy, haloC 1-7 alkyl, It may be further substituted with one or more selected from haloC 1-7 alkoxy, C 6-12 aryl, C 3-12 heteroaryl, nitro, haloC 6-12 aryl and haloC 3-12 heteroaryl.

상기 R1은 수소이고; R2는 수소 또는 C1-7알킬일 수 있고, 좋게는 상기 R1 및 R2는 수소일 수 있다.wherein R 1 is hydrogen; R 2 may be hydrogen or C 1-7 alkyl, preferably R 1 and R 2 may be hydrogen.

상기 펜타플루오로설파닐-치환 화합물은 보다 바람직하게 하기 화학식 4, 화학식 5, 화학식 6 또는 화학식 7로 표시될 수 있다.The pentafluorosulfanyl-substituted compound may be more preferably represented by the following Chemical Formula 4, Chemical Formula 5, Chemical Formula 6 or Chemical Formula 7.

[화학식 4][Formula 4]

Figure 112019133198795-pat00011
Figure 112019133198795-pat00011

[화학식 5][Formula 5]

Figure 112019133198795-pat00012
Figure 112019133198795-pat00012

[화학식 6][Formula 6]

Figure 112019133198795-pat00013
Figure 112019133198795-pat00013

[화학식 7][Formula 7]

Figure 112019133198795-pat00014
Figure 112019133198795-pat00014

상기 화학식 4 내지 7에서,In Formulas 4 to 7,

R11은 C1-7알킬, C6-12아릴, C3-12헤테로아릴, C1-7알콕시 또는 C6-12아릴옥시이고;R 11 is C 1-7 alkyl, C 6-12 aryl, C 3-12 heteroaryl, C 1-7 alkoxy or C 6-12 aryloxy;

R12는 C1-7알킬, C6-12아릴 또는 C3-12헤테로아릴이고;R 12 is C 1-7 alkyl, C 6-12 aryl or C 3-12 heteroaryl;

R3a, R3b 및 R3c는 각각 독립적으로 수소, 할로겐, C1-7알킬, C1-7알콕시, 할로C1-7알킬 또는 할로C1-7알콕시이고;R 3a , R 3b and R 3c are each independently hydrogen, halogen, C 1-7 alkyl, C 1-7 alkoxy, haloC 1-7 alkyl or haloC 1-7 alkoxy;

상기 R11의 알킬, 아릴, 헤테로아릴, 알콕시 또는 아릴옥시, 및 R12의 알킬, 아릴 또는 헤테로아릴은 할로겐, C1-7알킬, C1-7알콕시, 할로C1-7알킬, 할로C1-7알콕시, C6-12아릴, C3-12헤테로아릴, 니트로, 할로C6-12아릴 및 할로C3-12헤테로아릴로부터 선택되는 하나 이상으로 더 치환될 수 있다.Alkyl, aryl, heteroaryl, alkoxy or aryloxy of R 11 , and alkyl, aryl or heteroaryl of R 12 are halogen, C 1-7 alkyl, C 1-7 alkoxy, haloC 1-7 alkyl, haloC It may be further substituted with one or more selected from 1-7 alkoxy, C 6-12 aryl, C 3-12 heteroaryl, nitro, haloC 6-12 aryl and haloC 3-12 heteroaryl.

일 구체예에 있어, 상기 R11은 C6-12아릴, C3-12헤테로아릴, C1-7알콕시 또는 C6-12아릴옥시이고; 상기 R11의 아릴, 헤테로아릴, 알콕시 또는 아릴옥시는 할로겐, C1-7알킬, C1-7알콕시, 할로C1-7알킬, 할로C1-7알콕시, C6-12아릴, C3-12헤테로아릴, 니트로, 할로C6-12아릴 및 할로C3-12헤테로아릴로부터 선택되는 하나 이상으로 더 치환될 수 있다.In one embodiment, R 11 is C 6-12 aryl, C 3-12 heteroaryl, C 1-7 alkoxy or C 6-12 aryloxy; Aryl, heteroaryl, alkoxy or aryloxy of R 11 is halogen, C 1-7 alkyl, C 1-7 alkoxy, haloC 1-7 alkyl, haloC 1-7 alkoxy, C 6-12 aryl, C 3 It may be further substituted with one or more selected from -12 heteroaryl, nitro, haloC 6-12 aryl and haloC 3-12 heteroaryl.

일 구체예에 있어, 상기 R11은

Figure 112019133198795-pat00015
,
Figure 112019133198795-pat00016
,
Figure 112019133198795-pat00017
,
Figure 112019133198795-pat00018
,
Figure 112019133198795-pat00019
,
Figure 112019133198795-pat00020
,
Figure 112019133198795-pat00021
,
Figure 112019133198795-pat00022
, C1-4알콕시, 벤질옥시 또는 페녹시이고;In one embodiment, R 11 is
Figure 112019133198795-pat00015
,
Figure 112019133198795-pat00016
,
Figure 112019133198795-pat00017
,
Figure 112019133198795-pat00018
,
Figure 112019133198795-pat00019
,
Figure 112019133198795-pat00020
,
Figure 112019133198795-pat00021
,
Figure 112019133198795-pat00022
, C 1-4 alkoxy, benzyloxy or phenoxy;

R12는 C1-4알킬,

Figure 112019133198795-pat00023
,
Figure 112019133198795-pat00024
,
Figure 112019133198795-pat00025
,
Figure 112019133198795-pat00026
,
Figure 112019133198795-pat00027
,
Figure 112019133198795-pat00028
,
Figure 112019133198795-pat00029
,
Figure 112019133198795-pat00030
또는
Figure 112019133198795-pat00031
이고;R 12 is C 1-4 alkyl,
Figure 112019133198795-pat00023
,
Figure 112019133198795-pat00024
,
Figure 112019133198795-pat00025
,
Figure 112019133198795-pat00026
,
Figure 112019133198795-pat00027
,
Figure 112019133198795-pat00028
,
Figure 112019133198795-pat00029
,
Figure 112019133198795-pat00030
or
Figure 112019133198795-pat00031
ego;

W는 NR', O 또는 S이고;W is NR', O or S;

R'는 수소, C1-4알킬, C6-12아릴, C3-12헤테로아릴, 할로C6-12아릴 또는 할로C3-12헤테로아릴이고;R' is hydrogen, C 1-4 alkyl, C 6-12 aryl, C 3-12 heteroaryl, haloC 6-12 aryl or haloC 3-12 heteroaryl;

R3a, R3b 및 R3c는 각각 독립적으로 수소, 할로겐, C1-4알킬, C1-4알콕시 또는 할로C1-4알킬이고;R 3a , R 3b and R 3c are each independently hydrogen, halogen, C 1-4 alkyl, C 1-4 alkoxy or haloC 1-4 alkyl;

R21은 할로겐, C1-4알킬, C1-4알콕시, 할로C1-4알킬, 할로C1-4알콕시, C6-12아릴, C3-12헤테로아릴, 니트로, 할로C6-12아릴 또는 할로C3-12헤테로아릴이고;R 21 is halogen, C 1-4 alkyl, C 1-4 alkoxy, haloC 1-4 alkyl, haloC 1-4 alkoxy, C 6-12 aryl, C 3-12 heteroaryl, nitro, haloC 6- 12 aryl or haloC 3-12 heteroaryl;

a는 0 내지 5의 정수이고, b는 0 내지 7의 정수이고, c는 0 내지 4의 정수이고, d는 0 내지 6의 정수이고, e는 0 내지 3의 정수이고, f는 0 내지 2의 정수이다.a is an integer from 0 to 5, b is an integer from 0 to 7, c is an integer from 0 to 4, d is an integer from 0 to 6, e is an integer from 0 to 3, and f is from 0 to 2 is the integer of

상기 펜타플루오로설파닐-치환 화합물은 구체적으로 하기 구조로부터 선택되는 어느 하나일 수 있으며, 이에 한정되는 것은 아니다. The pentafluorosulfanyl-substituted compound may be any one specifically selected from the following structures, but is not limited thereto.

Figure 112019133198795-pat00032
Figure 112019133198795-pat00032

Figure 112019133198795-pat00033
Figure 112019133198795-pat00033

Figure 112019133198795-pat00034
Figure 112019133198795-pat00034

또한, 상기 화학식 1의 펜타플루오로설파닐-치환 화합물의 제조방법이 개시된다.In addition, a method for preparing the pentafluorosulfanyl-substituted compound of Formula 1 is disclosed.

상기 펜타플루오로설파닐-치환 화합물은 하기 반응식 1에 예시된 바와 같이, 산 또는 산 할라이드 화합물 (a)와 펜타플루오로설파닐-치환 아닐린 화합물 (b)를 아마이드 커플링(amide coupling) 반응시켜 제조될 수 있다. 그러나, 하기의 제조방법이 상기 펜타플루오로설파닐-치환 화합물을 제조하는 방법을 한정하는 것은 아니다. 하기 반응식 1의 제조방법은 예시일 뿐이며, 특정 치환체에 따라 당업자에 의해 용이하게 변형될 수 있음은 자명하다.The pentafluorosulfanyl-substituted compound is prepared by reacting an acid or acid halide compound (a) with a pentafluorosulfanyl-substituted aniline compound (b) by amide coupling, as illustrated in Scheme 1 below. can be manufactured. However, the following preparation method is not limited to the preparation method of the pentafluorosulfanyl-substituted compound. It is apparent that the preparation method of Scheme 1 below is merely an example, and can be easily modified by those skilled in the art according to specific substituents.

[반응식 1][Scheme 1]

Figure 112019133198795-pat00035
Figure 112019133198795-pat00035

상기 반응식 1에서, L, R, R1 내지 R3 및 m은 상기 화학식 1에서 정의한 바와 동일하고; Z는 할로겐 또는 하이드록시이다.In Scheme 1, L, R, R 1 to R 3 and m are the same as defined in Formula 1; Z is halogen or hydroxy.

본 발명의 범주에는 상기 화학식 1의 펜타플루오로설파닐-치환 화합물 뿐만 아니라 이의 수화물, 이의 용매화물 또는 이의 염의 형태도 포함된다. 상기 염은 농업적으로 적합한 무기산 또는 유기산의 염인 것이 바람직하며, 예를 들어 브롬산, 염산, 질산, 인산, 황산, 아세트산, 부티르산, 푸마르산, 젖산, 말레산, 말론산, 옥살산, 프로피온산, 살리실산, 타르타르산, 4-톨루엔술폰산 또는 발레르산에 의한 산-부가염을 포함한다. 상기 수화물은 비공유적 분자간력(non-covalent intermolecular force)에 의해 결합된 화학양론적(stoichiometric) 또는 비화학양론적(non-stoichiometric) 량의 물을 포함하고 있는 본 발명의 화합물 또는 그것의 염을 의미한다. 상기 용매화물은 비공유적 분자간력에 의해 결합된 화학양론적 또는 비화학양론적 양의 용매를 포함하고 있는 본 발명의 화합물 또는 그것의 염을 의미한다. 그에 관한 바람직한 용매들로는 휘발성, 비독성 용매들이 있다.The scope of the present invention includes not only the pentafluorosulfanyl-substituted compound of Formula 1 above, but also the form of a hydrate, solvate or salt thereof. The salt is preferably a salt of an agriculturally suitable inorganic or organic acid, for example, hydrobromic acid, hydrochloric acid, nitric acid, phosphoric acid, sulfuric acid, acetic acid, butyric acid, fumaric acid, lactic acid, maleic acid, malonic acid, oxalic acid, propionic acid, salicylic acid, acid-addition salts with tartaric acid, 4-toluenesulfonic acid or valeric acid. The hydrate is a compound of the present invention or a salt thereof containing a stoichiometric or non-stoichiometric amount of water bound by non-covalent intermolecular force. it means. The solvate means a compound of the present invention or a salt thereof containing a stoichiometric or non-stoichiometric amount of a solvent bound by non-covalent intermolecular forces. Preferred solvents therefor include volatile, non-toxic solvents.

또한, 활성 성분으로서 유효량의 상기 화학식 1의 펜타플루오로설파닐-치환 화합물, 이의 수화물, 이의 용매화물 또는 이의 염을 함유하는 살충제 조성물이 개시된다.Also disclosed is a pesticide composition containing an effective amount of the pentafluorosulfanyl-substituted compound of formula (1), a hydrate thereof, a solvate thereof or a salt thereof as an active ingredient.

상기 화학식 1의 펜타플루오로설파닐-치환 화합물을 살충제의 활성 성분으로 사용할 경우, 그것은 임의의 기타 성분들의 첨가 없이 그 자체로서 또는 염의 형태로 사용될 수 있도 있고 적당한 담체 및/또는 부가제와 같이 사용할 수도 있다. 적당한 담체 및 부가제는 고체 또는 액체일 수 있으며, 통상제제에 사용되는 천연 또는 재생물질, 용매, 분산제, 습윤제, 접착제, 결착제 및/또는 비료가 이에 속한다. 살충제로 사용 시 화학식 1의 펜타플루오로설파닐-치환 화합물은 통상의 방법에 따라 통상의 제제형태, 예를 들면 분제, 유제, 입제, 분산액, 분무제, 용액 또는 현탁액으로 만들 수 있다. 수액제제로 사용되는 캐틀 딥(cattle dips) 및 스프레이 레이스(spray races)로 제조할 수도 있다.When the pentafluorosulfanyl-substituted compound of Formula 1 is used as an active ingredient of an insecticide, it may be used as such or in the form of a salt without the addition of any other ingredients, and may be used together with suitable carriers and/or additives. may be Suitable carriers and additives may be solid or liquid, and include natural or regenerated materials, solvents, dispersants, wetting agents, adhesives, binders and/or fertilizers commonly used in formulations. When used as an insecticide, the pentafluorosulfanyl-substituted compound of Formula 1 can be prepared in a conventional formulation form, for example, a powder, emulsion, granule, dispersion, spray, solution or suspension according to a conventional method. It can also be prepared as kettle dips and spray races used as infusions.

또한 조성물은 화학식 1의 펜타플루오로설파닐-치환 화합물을 적당한 담체와, 또 활성물질에 불활성인 분산제나 용매를 가하여 완전히 혼합 및/또는 분쇄하는 통상의 방법에 따라 얻을 수 있다. 상기 담체는 약학적으로 허용가능한 담체라면 무방하며, 예를 들어 카오린, 탈크, 돌로마이트, 납석, 규조토, 칼슘카보네이트 등을 들 수 있다.Also, the composition can be obtained according to a conventional method in which the pentafluorosulfanyl-substituted compound of formula (1) is thoroughly mixed and/or pulverized by adding an appropriate carrier and an inert dispersant or solvent to the active material. The carrier may be any pharmaceutically acceptable carrier, for example, kaolin, talc, dolomite, pyrophyllite, diatomaceous earth, calcium carbonate, and the like.

상기 화학식 1의 펜타플루오로설파닐-치환 화합물의 사용 약량은 해충의 발생량이나 생육정도, 제제 등의 요소에 의해 결정될 수 있다.The amount of use of the pentafluorosulfanyl-substituted compound of Formula 1 may be determined by factors such as the amount or growth level of pests, and the preparation.

아울러, 상기 화학식 1의 펜타플루오로설파닐-치환 화합물, 이의 수화물, 이의 용매화물 또는 이의 염을 농작물 또는 이의 서식지에 처리하여 해충을 방제하는 방법이 개시된다. In addition, a method for controlling pests by treating crops or habitats thereof with the pentafluorosulfanyl-substituted compound of Formula 1, a hydrate thereof, a solvate thereof, or a salt thereof is disclosed.

상기 해충은 바람직하게는 나방류이고, 보다 구체적으로는 배추좀나방, 담배거세미나방 등을 들 수 있다.The pests are preferably moths, and more specifically, include Chinese cabbage moth and tobacco spider moth.

담배거세미나방(Spodoptera litura)은 아시아 전역에 널리 분포하며, 이의 유충은 모든 채소류와 전작물에 피해를 가하고, 심할 경우 식물체의 줄기만 남기고 섭식하는 광식성 해충이다.Tobacco spider moth (Spodoptera litura) is widely distributed throughout Asia, and its larvae damage all vegetables and crops, and in severe cases leave only the stems of plants.

이와 같은 화학식 1의 펜타플루오로설파닐-치환 화합물, 이의 수화물, 이의 용매화물 또는 이의 염을 함유하는 살충제 조성물은 곤충류의 다양한 해충류, 특히 배추좀나방, 담배거세미나방 등의 나방류에 대한 우수한 살충 효과를 발휘하면서도, 익충인 꿀벌에는 안전하다. 또한, 본 발명의 화합물은 토양 중에서 빨리 분해될 뿐만 아니라, 토양 중에 존재하더라도 물에 빨리 씻겨 내려가므로, 환경에 대한 우수한 안전성을 가진다. 즉, 본 발명의 화합물은 토양 잔류 기간이 매우 짧아 환경친화적이다.The pesticide composition containing the pentafluorosulfanyl-substituted compound of Formula 1, its hydrate, its solvate, or its salt is excellent against various pests of insects, in particular, moths such as diamondback moth and tobacco spider moth. While exhibiting an insecticidal effect, it is safe for bees, which are beneficial insects. In addition, the compound of the present invention is not only rapidly decomposed in soil, but is also quickly washed away with water even if present in soil, and thus has excellent environmental safety. That is, the compound of the present invention has a very short soil retention period and is environmentally friendly.

이하, 바람직한 실시예를 통하여 본 발명을 보다 상세히 설명하기로 한다. 다만, 이는 본 발명의 예시로 제시되는 것으로 어떠한 의미로도 이에 의해 본 발명의 권리범위가 한정되는 것은 아니며, 본 발명의 권리범위는 후술하는 청구범위에 따라 정의될 뿐이다. Hereinafter, the present invention will be described in more detail through preferred embodiments. However, this is presented as an example of the present invention, and the scope of the present invention is not limited by this in any sense, and the scope of the present invention is only defined according to the following claims.

실시예Example

[실시예 1] 화합물 1의 제조[Example 1] Preparation of compound 1

Figure 112019133198795-pat00036
Figure 112019133198795-pat00036

7ml vial에 아닐린 화합물 b-1 (95 mg, 0.4 mmol)과 산 화합물 a-1 (104 mg, 1.0 eq, 0.4 mmol)을 넣고, CH3CN (0.3 M, 1 mL)과 3-picoline (0.071 mL, 0.7 mmol)을 넣고 10분 후 MsCl (0.035 mL, 0.45 mmol)을 천천히 가하고 상온에서 24시간동안 반응시켰다. 반응 종료 후 Rotavapor로 CH3CN을 제거하고 물 (20 mL)과 ethyl acetate (15 mL × 2)로 추출한 다음, 유기층을 무수 MgSO4로 건조한 후 감압 농축하였다. 얻어진 잔사를 실리카겔 컬럼 크로마토그래피(EA : Hex = 1:2)로 분리정제하여 상아색 고체의 표제화합물 1을 수득하였다(138 mg, 75 %).In a 7ml vial, put aniline compound b-1 (95 mg, 0.4 mmol) and acid compound a-1 (104 mg, 1.0 eq, 0.4 mmol), CH 3 CN (0.3 M, 1 mL) and 3-picoline (0.071) mL, 0.7 mmol) was added, and after 10 minutes, MsCl (0.035 mL, 0.45 mmol) was slowly added thereto, followed by reaction at room temperature for 24 hours. After completion of the reaction, CH 3 CN was removed with Rotavapor, extracted with water (20 mL) and ethyl acetate (15 mL × 2), and the organic layer was dried over anhydrous MgSO 4 and concentrated under reduced pressure. The obtained residue was separated and purified by silica gel column chromatography (EA: Hex = 1:2) to obtain the title compound 1 as an ivory solid (138 mg, 75%).

1H NMR (300MHz, CDCl3) δ 8.72 (s, 2H), 8.12 (s, 1H), 7.91 (dd, J = 9.7, 7.7 Hz, 2H), 7.67-7.53 (m, 3H), 7.40 (t, J = 8.0 Hz, 1H), 7.25-7.21 (m, 2H). 1 H NMR (300 MHz, CDCl 3 ) δ 8.72 (s, 2H), 8.12 (s, 1H), 7.91 (dd, J = 9.7, 7.7 Hz, 2H), 7.67-7.53 (m, 3H), 7.40 (t) , J = 8.0 Hz, 1H), 7.25-7.21 (m, 2H).

[실시예 2] 화합물 2의 제조[Example 2] Preparation of compound 2

Figure 112019133198795-pat00037
Figure 112019133198795-pat00037

7ml vial에 아닐린 화합물 b-2 (25 mg, 0.07 mmol)과 THF (0.1M, 0.7 mL)과 pyridine (0.14 mL, 24.0 eq, 1.68 mmol)을 넣고, 산 클로라이드 화합물 a-2 (0.013 mL, 1.5 eq, 0.105 mmmol)을 넣은 후 상온에서 1시간 반응시켰다. 반응 종료 후 물 (20 mL)과 ethyl acetate (15 mL × 2)로 추출한 다음, 유기층을 무수 MgSO4로 건조한 후 감압 농축하였다. 얻어진 잔사를 실리카겔 컬럼 크로마토그래피(EA : Hex = 1:1)로 분리정제하여 상아색 고체의 표제화합물 2을 수득하였다(35.6 mg, 99 %).In a 7ml vial, put aniline compound b-2 (25 mg, 0.07 mmol), THF (0.1M, 0.7 mL) and pyridine (0.14 mL, 24.0 eq, 1.68 mmol), and acid chloride compound a-2 (0.013 mL, 1.5 eq, 0.105 mmol) was added and reacted at room temperature for 1 hour. After completion of the reaction, the mixture was extracted with water (20 mL) and ethyl acetate (15 mL × 2), and the organic layer was dried over anhydrous MgSO 4 and concentrated under reduced pressure. The obtained residue was separated and purified by silica gel column chromatography (EA: Hex = 1:1) to obtain the title compound 2 as an ivory solid (35.6 mg, 99%).

1H NMR (300MHz, CDCl3) δ 8.77 (d, J = 15.3 Hz, 1H), 8.63 (t, J = 7.3 Hz, 1H), 8.39 (d, J = 12.3 Hz, 1H), 8.13-8.04 (m, 1H), 7.91 (d, J = 7.3 Hz, 1H), 7.78 (s, 3H), 7.39 (t, J = 8.2 Hz, 1H), 7.17-7.10 (m, 1H). 1 H NMR (300 MHz, CDCl 3 ) δ 8.77 (d, J = 15.3 Hz, 1H), 8.63 (t, J = 7.3 Hz, 1H), 8.39 (d, J = 12.3 Hz, 1H), 8.13-8.04 ( m, 1H), 7.91 (d, J = 7.3 Hz, 1H), 7.78 (s, 3H), 7.39 (t, J = 8.2 Hz, 1H), 7.17-7.10 (m, 1H).

[실시예 3] 화합물 3의 제조[Example 3] Preparation of compound 3

Figure 112019133198795-pat00038
Figure 112019133198795-pat00038

25ml 둥근 바닥 플라스크에 아닐린 화합물 b-2 (35 mg, 0.065 mmol)을 가하고 DMF와 물 (0.1M, 6.5 mL)을 5:1 부피 비율로 넣고, Pd(PPh3)4 (4 mg, 0.05 eq. 0.0033 mmol)과 Na2CO3 (276 mL, 40 eq. 2.6 mmmol) 그리고 산 화합물 a-3 (8 mg, 1.0 eq. 0.065 mmol)을 넣은 후 100℃에서 2시간 반응시켰다. 반응 종료 후 물 (20 mL)과 ethyl acetate (15 mL × 2)로 추출한 다음, 유기층을 무수 MgSO4로 건조한 후 감압 농축하였다. 얻어진 잔사를 실리카겔 컬럼 크로마토그래피 (EA : Hex = 1:1)로 분리정제하여 하얀색 고체의 표제화합물 3을 수득하였다(10.7 mg, 31 %).Aniline compound b-2 (35 mg, 0.065 mmol) was added to a 25 ml round-bottom flask, and DMF and water (0.1M, 6.5 mL) were added in a 5:1 volume ratio, and Pd(PPh 3 ) 4 (4 mg, 0.05 eq) was added. 0.0033 mmol) and Na 2 CO 3 (276 mL, 40 eq. 2.6 mmol) and acid compound a-3 (8 mg, 1.0 eq. 0.065 mmol) were added and reacted at 100° C. for 2 hours. After completion of the reaction, the mixture was extracted with water (20 mL) and ethyl acetate (15 mL × 2), and the organic layer was dried over anhydrous MgSO 4 and concentrated under reduced pressure. The obtained residue was separated and purified by silica gel column chromatography (EA: Hex = 1:1) to obtain the title compound 3 as a white solid (10.7 mg, 31 %).

1H NMR (300MHz, CDCl3) δ 8.60 (t, J = 7.9 Hz, 1H), 8.45 (d, J = 11.4 Hz, 1H), 8.09 (s, 1H), 7.94-7.88 (m, 2H), 7.84 (d, J = 8.8 Hz, 1H), 7.78 (d, J = 1.5 Hz, 5H), 7.63 (t, J = 6.7 Hz, 1H), 7.58-7.51 (m, 2H), 7.37 (d, J = 7.9 Hz, 1H). 1 H NMR (300 MHz, CDCl 3 ) δ 8.60 (t, J = 7.9 Hz, 1H), 8.45 (d, J = 11.4 Hz, 1H), 8.09 (s, 1H), 7.94-7.88 (m, 2H), 7.84 (d, J = 8.8 Hz, 1H), 7.78 (d, J = 1.5 Hz, 5H), 7.63 (t, J = 6.7 Hz, 1H), 7.58-7.51 (m, 2H), 7.37 (d, J = 7.9 Hz, 1H).

[실시예 4] 화합물 4의 제조[Example 4] Preparation of compound 4

Figure 112019133198795-pat00039
Figure 112019133198795-pat00039

7ml vial에 아닐린 화합물 b-2 (36 mg, 1eq. 0.1 mmol)과 산 화합물 a-4 (30 mg, 0.1 mmmol) 을 넣고, CH3CN (0.1 M, 1 mL)과 3-picoline (0.03 mL, 3.2 eq, 0.32 mmol)을 넣고 10분 후 MsCl (0.01 mL, 1.2 eq, 0.12 mmol)을 천천히 가하고 상온에서 24시간 반응시켰다. 반응 종료 후 Rotavapor로 CH3CN을 제거하고 물 (10 mL)과 ethyl acetate (5 mL × 2)로 추출한 다음, 유기층을 무수 MgSO4로 건조한 후 감압 농축하였다. 얻어진 잔사를 실리카겔 컬럼 크로마토그래피(EA : Hex = 1:2)로 분리정제하여 흰색 고체의 표제화합물 4를 수득하였다(44.7 mg, 83 %).Put aniline compound b-2 (36 mg, 1eq. 0.1 mmol) and acid compound a-4 (30 mg, 0.1 mmmol) in a 7ml vial, CH 3 CN (0.1 M, 1 mL) and 3-picoline (0.03 mL) , 3.2 eq, 0.32 mmol) was added, and after 10 minutes, MsCl (0.01 mL, 1.2 eq, 0.12 mmol) was slowly added and reacted at room temperature for 24 hours. After completion of the reaction, CH 3 CN was removed with Rotavapor, extracted with water (10 mL) and ethyl acetate (5 mL × 2), and the organic layer was dried over anhydrous MgSO 4 and concentrated under reduced pressure. The obtained residue was separated and purified by silica gel column chromatography (EA: Hex = 1:2) to obtain the title compound 4 as a white solid (44.7 mg, 83%).

1H NMR (300MHz, CDCl3) δ 8.51 (dd, J = 4.7, 1.8 Hz, 1H), 8.40-8.29 (m, 3H), 7.96 (dd, J = 8.1, 1.6 Hz, 1H), 7.83 (d, J = 7.6 Hz, 1H), 7.77 (d, J = 2.1 Hz, 4H), 7.46 (dd, J = 8.2, 4.7 Hz, 1H), 7.29 (d, J = 7.9 Hz, 1H), 6.97 (s, 1H). 1 H NMR (300 MHz, CDCl 3 ) δ 8.51 (dd, J = 4.7, 1.8 Hz, 1H), 8.40-8.29 (m, 3H), 7.96 (dd, J = 8.1, 1.6 Hz, 1H), 7.83 (d , J = 7.6 Hz, 1H), 7.77 (d, J = 2.1 Hz, 4H), 7.46 (dd, J = 8.2, 4.7 Hz, 1H), 7.29 (d, J = 7.9 Hz, 1H), 6.97 (s) , 1H).

[실시예 5] 화합물 5의 제조[Example 5] Preparation of compound 5

Figure 112019133198795-pat00040
Figure 112019133198795-pat00040

7ml vial에 아닐린 화합물 b-3 (15 mg, 0.04 mmol)과 물 (0.2 M, 0.2 mL)과 NaOH (3.2 mg, 2.0 eq. 0.08 mmol)을 넣고, 산 클로라이드 화합물 a-5 (0.007 mL, 1.5 eq. 0.06 mmmol)을 넣은 후 상온에서 1시간 반응시켰다. 반응 종료 후 물 (20 mL)과 ethyl acetate (15 mL × 2)로 추출한 다음, 유기층을 무수 MgSO4로 건조한 후 감압 농축하였다. 얻어진 잔사를 실리카겔 컬럼 크로마토그래피(EA : Hex = 1:1)로 분리정제하여 흰색 고체의 표제화합물 5를 수득하였다(16.2 mg, 85 %).In a 7ml vial, put aniline compound b-3 (15 mg, 0.04 mmol), water (0.2 M, 0.2 mL) and NaOH (3.2 mg, 2.0 eq. 0.08 mmol), and acid chloride compound a-5 (0.007 mL, 1.5 eq. 0.06 mmol) was added and reacted at room temperature for 1 hour. After completion of the reaction, the mixture was extracted with water (20 mL) and ethyl acetate (15 mL × 2), and the organic layer was dried over anhydrous MgSO 4 and concentrated under reduced pressure. The obtained residue was separated and purified by silica gel column chromatography (EA: Hex = 1:1) to obtain the title compound 5 as a white solid (16.2 mg, 85%).

1H NMR (500MHz, CDCl3) δ 8.63 (td, J = 7.9, 1.7 Hz, 1H), 8.39 (d, J = 8.9 Hz, 1H), 8.33 (d, J = 14.5 Hz, 1H), 8.08-8.05 (m, 1H), 7.93-7.87 (m, 3H), 7.66 (dd, J = 9.0, 2.9 Hz, 1H), 7.63-7.58 (m, 2H), 7.53 (ddt, J = 8.1, 6.6, 1.5 Hz, 2H), 7.38 (t, J = 8.1 Hz, 1H), 2.41 (s, 3H). 1 H NMR (500 MHz, CDCl 3 ) δ 8.63 (td, J = 7.9, 1.7 Hz, 1H), 8.39 (d, J = 8.9 Hz, 1H), 8.33 (d, J = 14.5 Hz, 1H), 8.08- 8.05 (m, 1H), 7.93-7.87 (m, 3H), 7.66 (dd, J = 9.0, 2.9 Hz, 1H), 7.63-7.58 (m, 2H), 7.53 (ddt, J = 8.1, 6.6, 1.5 Hz, 2H), 7.38 (t, J = 8.1 Hz, 1H), 2.41 (s, 3H).

[실시예 6 내지 59] [Examples 6 to 59]

상기 실시예 1 내지 5의 방법에 따라 하기 표 1의 화합물 6 내지 59를 제조하였으며, 제조된 화합물들의 동정자료를 하기 표 2에 나타내었다.Compounds 6 to 59 of Table 1 were prepared according to the methods of Examples 1 to 5, and identification data of the prepared compounds are shown in Table 2 below.

[표 1][Table 1]

Figure 112019133198795-pat00041
Figure 112019133198795-pat00041

Figure 112019133198795-pat00042
Figure 112019133198795-pat00042

Figure 112019133198795-pat00043
Figure 112019133198795-pat00043

Figure 112019133198795-pat00044
Figure 112019133198795-pat00044

Figure 112019133198795-pat00045
Figure 112019133198795-pat00045

Figure 112019133198795-pat00046
Figure 112019133198795-pat00046

[표 2][Table 2]

Figure 112019133198795-pat00047
Figure 112019133198795-pat00047

Figure 112019133198795-pat00048
Figure 112019133198795-pat00048

Figure 112019133198795-pat00049
Figure 112019133198795-pat00049

Figure 112019133198795-pat00050
Figure 112019133198795-pat00050

Figure 112019133198795-pat00051
Figure 112019133198795-pat00051

Figure 112019133198795-pat00052
Figure 112019133198795-pat00052

상기 실시예에서 제조된 화합물의 활성을 알아보기 위하여 하기에 기재되는 생물 검정법을 이용하여 담배거세미나방 및 배추좀나방에 대한 살충활성을 측정하였다.In order to examine the activity of the compounds prepared in the above Examples, the insecticidal activity against tobacco spider moth and diamondback moth was measured using the bioassay described below.

달리 구체화되지 않는 경우, 시험 용액은 하기와 같이 제조된다: 실시예 화합물을 1:1 (vol:vol) 증류수:아세톤의 혼합물에 원하는 농도로 용해시킨다. 시험 용액은 사용일에 및 일반적으로 ppm (wt/vol)의 농도로 제조된다.Unless otherwise specified, test solutions are prepared as follows: Example compounds are dissolved to the desired concentration in a mixture of 1:1 (vol:vol) distilled water:acetone. Test solutions are prepared on the day of use and generally at a concentration of ppm (wt/vol).

[시험예 1] 담배거세미나방(Spodoptera litura)의 살충활성시험(엽침지법)[Test Example 1] Insecticidal activity test of tobacco spider moth (Spodoptera litura) (leaf immersion method)

담배거세미나방은 경주 인근에서 채집 후 사육실에서 누대 사육한 개체를 사용하였다. 양배추(다이야)의 잎을 직경 5.8㎝의 절편으로 만든 후, 시험할 약제가 희석된 5%의 아세톤 용액에 30초간 침지하여 충분히 음건하였다. 음건한 양배추 잎을 여과지가 깔린 패트리디쉬(직경 8.8㎝)에 놓고 담배거세미나방 2령충을 10마리씩 3회 반복 접종하였다. 이를 광조건 16:8시간, 25±1℃ 및 상대습도 50~60% 조건하에서 보관하였으며, 접종 24시간, 48시간, 72시간, 및 96시간 후 담배거세미나방의 생충수를 조사하였다. 개체의 방제가는 처리 전 밀도를 기초로 처리 후 밀도를 보정하고 이를 다시 무처리에 대한 보정 살충율로서 환산하여 표시하였으며, 그 결과를 하기 표 3에 기재하였다(참고 문헌: A method of computing the effectiveness of an insecticide. J. Econ. Entomol. 18:265~267. Abbott, 1925). Tobacco spider moths were collected near Gyeongju and then bred in a breeding room for generations. After cutting cabbage (Daiya) leaves with a diameter of 5.8 cm, they were immersed in a 5% acetone solution diluted with the drug to be tested for 30 seconds, and then sufficiently dried in the shade. Shaded cabbage leaves were placed on a Petri dish (diameter 8.8 cm) lined with filter paper and inoculated with 10 Tobacco spider moth 2nd instars 3 times each. These were stored under light conditions of 16:8 hours, 25±1° C. and 50-60% relative humidity, and the number of live insects of tobacco spider moth was investigated 24 hours, 48 hours, 72 hours, and 96 hours after inoculation. The control value of an individual corrected the density after treatment based on the density before treatment, and it was converted and displayed as a corrected insecticidal rate for no treatment, and the results are described in Table 3 below (Reference: A method of computing the effectiveness of an insecticide. J. Econ. Entomol. 18:265-267. Abbott, 1925).

[수학식 1][Equation 1]

방제가 = (무처리 생충율 - 처리구 생충율) / 무처리 생충율 x 100Control value = (Untreated live insect rate - Treated group live rate) / Untreated live insect rate x 100

[수학식 2][Equation 2]

생충율 = 처리 후 밀도 / 처리 전 밀도 × 100Viability = Density after treatment / Density before treatment × 100

A : 60% ≤ 96시간후 방제가 ≤ 100%A: 60% ≤ 96 hours after control ≤ 100%

B : 30% ≤ 96시간후 방제가 < 60%B: 30% ≤ 96 hours after control < 60%

C : 10% ≤ 96시간후 방제가 < 30%C: 10% ≤ 96 hours after control < 30%

[표 3][Table 3]

Figure 112019133198795-pat00053
Figure 112019133198795-pat00053

본 발명에 따른 화합물들은 담배거세미나방에 대하여 적정 수준의 방제가를 나타냈다.The compounds according to the present invention showed an appropriate level of control value against the tobacco spider moth.

특히, 화합물 9, 33, 36, 56 및 59의 경우 10 ppm의 농도로 처리시 담배거세미나방에 대하여 60% 이상의 우수한 방제가를 나타내었다. 화합물 9의 경우 10 ppm 처리 시 접종 72시간 후 100%의 방제가를 나타내었고, 접종 96시간 후 섭식 면적은 5% 미만으로, 양배추 잎이 거의 손상되지 않아 매우 우수한 방제효과를 가짐을 확인하였다.In particular, in the case of compounds 9, 33, 36, 56 and 59, when treated at a concentration of 10 ppm, they exhibited an excellent control value of 60% or more against tobacco spider moth. In the case of compound 9, 10 ppm treatment showed a 100% control value after 72 hours of inoculation, and the feeding area was less than 5% after 96 hours of inoculation.

[시험예 2] 배추좀나방(Plutella xylostella)에 대한 살충활성시험(엽침지법)[Test Example 2] Insecticidal activity test for Chinese cabbage moth ( Plutella xylostella ) (leaf immersion method)

배추좀나방은 경주 인근에서 채집 후 사육실에서 누대 사육한 개체를 사용하였다. 양배추(다이야)의 잎을 직경 5.8㎝의 절편으로 만든 후, 시험할 약제가 희석된 5%의 아세톤 용액에 30초간 침지하여 충분히 음건하였다. 음건한 양배추 잎을 여과지가 깔린 패트리디쉬(직경 8.8㎝)에 놓고 배추좀나방 3령충을 10마리씩 3회 반복 접종하였다. 이를 광조건 16:8시간, 25±1℃, 및 상대습도 50~60% 조건하에서 보관하면서, 접종 후 24시간, 48시간, 72시간 및 96시간에 배추좀나방의 생충수를 조사하였다. 방제가는 상기 수학식 1 및 2와 같이 처리전 밀도를 기초로 처리 후 밀도를 보정하고 이를 다시 무처리에 대한 보정 살충율로서 환산하여 표시하였다.Cabbage moths were collected near Gyeongju and then bred in a breeding room for generations. After cutting cabbage (Daiya) leaves with a diameter of 5.8 cm, they were immersed in a 5% acetone solution diluted with the drug to be tested for 30 seconds, and then sufficiently dried in the shade. The shade-dried cabbage leaves were placed on a Petri dish (diameter 8.8 cm) lined with filter paper, and inoculation of 10 Chinese cabbage moth 3 instars was repeated 3 times each. It was stored under light conditions of 16:8 hours, 25±1° C., and 50-60% relative humidity, and the number of live insects of the Chinese dragonfly moth was investigated at 24 hours, 48 hours, 72 hours and 96 hours after inoculation. The control value was displayed by correcting the density after treatment based on the density before treatment as in Equations 1 and 2, and converting it back to the corrected insecticidal rate for no treatment.

화합물 56의 경우 1 ppm의 농도로 처리시 접종 48, 72 및 96시간 후 각각 80.0%, 83.3%, 86.7%의 방제가를 나타냈고, 화합물 59의 경우 1 ppm의 농도로 처리시 접종 24, 48, 72 및 96시간 후 각각 6.7%, 90.0%, 90.0%, 90.0%의 방제가를 나타냈다. 또한, 화합물 56 및 59를 각각 접종한지 96시간 후 섭식 면적은 모두 10% 미만으로, 양배추 잎이 거의 손상되지 않아 매우 우수한 방제효과를 가짐을 확인하였다.In the case of compound 56, when treated at a concentration of 1 ppm, 80.0%, 83.3%, and 86.7% after inoculation 48, 72 and 96 hours, respectively, were shown, and in the case of compound 59, when treated at a concentration of 1 ppm, inoculation 24, 48 , showed control values of 6.7%, 90.0%, 90.0%, and 90.0%, respectively, after 72 and 96 hours. In addition, 96 hours after each inoculation of compounds 56 and 59, the feeding area was all less than 10%, and it was confirmed that the cabbage leaves were hardly damaged and had a very excellent control effect.

이상과 같이 본 발명에서는 특정된 사항들과 한정된 실시예에 의해 설명되었으나 이는 본 발명의 보다 전반적인 이해를 돕기 위해서 제공된 것일 뿐, 본 발명은 상기의 실시예에 한정되는 것은 아니며, 본 발명이 속하는 분야에서 통상의 지식을 가진 자라면 이러한 기재로부터 다양한 수정 및 변형이 가능하다. 따라서, 본 발명의 사상은 설명된 실시예에 국한되어 정해져서는 아니되며, 후술하는 특허청구범위뿐 아니라 이 특허청구범위와 균등하거나 등가적 변형이 있는 모든 것들은 본 발명 사상의 범주에 속한다고 할 것이다.As described above, the present invention has been described by specific matters and limited examples, but these are provided to help a more general understanding of the present invention, and the present invention is not limited to the above examples, and the field to which the present invention belongs Various modifications and variations are possible from these descriptions by those of ordinary skill in the art. Therefore, the spirit of the present invention should not be limited to the described embodiments, and not only the claims to be described later, but also all those with equivalent or equivalent modifications to the claims will be said to belong to the scope of the spirit of the present invention. .

Claims (7)

하기 화학식 4 또는 화학식 6으로 표시되는 펜타플루오로설파닐-치환 화합물, 이의 수화물, 이의 용매화물 또는 이의 염:
[화학식 4]
Figure 112021061073543-pat00066

[화학식 6]
Figure 112021061073543-pat00067

상기 화학식 4 및 6에서,
R11은 C6-12아릴, C3-12헤테로아릴 또는 C1-7알콕시이고;
R12는 C1-7알킬, C6-12아릴 또는 C3-12헤테로아릴이고;
R3a 및 R3c는 각각 독립적으로 수소, 할로겐, C1-7알킬, C1-7알콕시, 할로C1-7알킬 또는 할로C1-7알콕시이고;
상기 R11의 아릴, 헤테로아릴 또는 알콕시, 및 R12의 아릴 또는 헤테로아릴은 할로겐, C1-7알킬, 할로C1-7알킬, C6-12아릴, C3-12헤테로아릴 및 니트로로부터 선택되는 하나 이상으로 더 치환될 수 있다.A pentafluorosulfanyl-substituted compound represented by the following formula (4) or formula (6), a hydrate thereof, a solvate thereof, or a salt thereof:
[Formula 4]
Figure 112021061073543-pat00066

[Formula 6]
Figure 112021061073543-pat00067

In Formulas 4 and 6,
R 11 is C 6-12 aryl, C 3-12 heteroaryl or C 1-7 alkoxy;
R 12 is C 1-7 alkyl, C 6-12 aryl or C 3-12 heteroaryl;
R 3a and R 3c are each independently hydrogen, halogen, C 1-7 alkyl, C 1-7 alkoxy, haloC 1-7 alkyl or haloC 1-7 alkoxy;
The aryl, heteroaryl or alkoxy of R 11 , and the aryl or heteroaryl of R 12 are selected from halogen, C 1-7 alkyl, haloC 1-7 alkyl, C 6-12 aryl, C 3-12 heteroaryl and nitro. It may be further substituted with one or more selected. 제 1항에 있어서,
상기 R11은
Figure 112021061073543-pat00068
,
Figure 112021061073543-pat00069
,
Figure 112021061073543-pat00070
또는 벤질옥시이고;
R12는 C1-4알킬,
Figure 112021061073543-pat00071
,
Figure 112021061073543-pat00072
또는
Figure 112021061073543-pat00073
이고;
W는 O 또는 S이고;
R3a 및 R3c는 각각 독립적으로 수소, 할로겐 또는 C1-4알킬이고;
R21은 할로겐, C1-4알킬, 할로C1-4알킬, C6-12아릴 또는 니트로이고;
a는 0 내지 5의 정수이고, c는 0 내지 4의 정수이고, e는 0 내지 3의 정수이고, f는 0 내지 2의 정수인, 펜타플루오로설파닐-치환 화합물, 이의 수화물, 이의 용매화물 또는 이의 염.The method of claim 1,
wherein R 11 is
Figure 112021061073543-pat00068
,
Figure 112021061073543-pat00069
,
Figure 112021061073543-pat00070
or benzyloxy;
R 12 is C 1-4 alkyl,
Figure 112021061073543-pat00071
,
Figure 112021061073543-pat00072
or
Figure 112021061073543-pat00073
ego;
W is O or S;
R 3a and R 3c are each independently hydrogen, halogen or C 1-4 alkyl;
R 21 is halogen, C 1-4 alkyl, haloC 1-4 alkyl, C 6-12 aryl or nitro;
a is an integer from 0 to 5, c is an integer from 0 to 4, e is an integer from 0 to 3, and f is an integer from 0 to 2; or a salt thereof. 삭제delete 삭제delete 제 1항에 있어서,
상기 펜타플루오로설파닐-치환 화합물은 하기 구조로부터 선택되는 어느 하나인, 펜타플루오로설파닐-치환 화합물, 이의 수화물, 이의 용매화물 또는 이의 염:
Figure 112021061073543-pat00074

Figure 112021061073543-pat00075

Figure 112021061073543-pat00076

Figure 112021061073543-pat00077
The method of claim 1,
The pentafluorosulfanyl-substituted compound is any one selected from the following structures, a pentafluorosulfanyl-substituted compound, a hydrate thereof, a solvate thereof, or a salt thereof:
Figure 112021061073543-pat00074

Figure 112021061073543-pat00075

Figure 112021061073543-pat00076

Figure 112021061073543-pat00077
 제 1항, 제 2항 및 제 5항에서 선택되는 어느 한 항에 따른 펜타플루오로설파닐-치환 화합물, 이의 수화물, 이의 용매화물 또는 이의 염을 활성 성분으로 함유하는 살충제 조성물.A pesticide composition comprising the pentafluorosulfanyl-substituted compound according to any one of claims 1, 2 and 5, a hydrate thereof, a solvate thereof or a salt thereof as an active ingredient. 제 6항에 따른 살충제 조성물을 농작물 또는 이의 서식지에 처리하여 해충을 방제하는 방법.A method for controlling pests by treating crops or their habitats with the pesticide composition according to claim 6 .
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