KR102660238B1 - Dihydroisoxazole derivative compound and pesticide composition comprising same - Google Patents
Dihydroisoxazole derivative compound and pesticide composition comprising same Download PDFInfo
- Publication number
- KR102660238B1 KR102660238B1 KR1020210183189A KR20210183189A KR102660238B1 KR 102660238 B1 KR102660238 B1 KR 102660238B1 KR 1020210183189 A KR1020210183189 A KR 1020210183189A KR 20210183189 A KR20210183189 A KR 20210183189A KR 102660238 B1 KR102660238 B1 KR 102660238B1
- Authority
- KR
- South Korea
- Prior art keywords
- trifluoromethyl
- dihydroisoxazol
- methylbenzamide
- dichlorophenyl
- naphthamide
- Prior art date
Links
- -1 Dihydroisoxazole derivative compound Chemical class 0.000 title claims abstract description 132
- 239000000203 mixture Substances 0.000 title claims description 31
- 239000000575 pesticide Substances 0.000 title claims description 19
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- 239000004480 active ingredient Substances 0.000 claims abstract description 5
- 125000000217 alkyl group Chemical group 0.000 claims description 32
- 229910052736 halogen Inorganic materials 0.000 claims description 22
- 150000002367 halogens Chemical class 0.000 claims description 22
- 238000000034 method Methods 0.000 claims description 20
- 150000003839 salts Chemical class 0.000 claims description 20
- 125000001188 haloalkyl group Chemical group 0.000 claims description 16
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- 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
- 238000004519 manufacturing process Methods 0.000 description 1
- 235000012054 meals Nutrition 0.000 description 1
- 235000010270 methyl p-hydroxybenzoate Nutrition 0.000 description 1
- 239000004292 methyl p-hydroxybenzoate Substances 0.000 description 1
- LXCFILQKKLGQFO-UHFFFAOYSA-N methylparaben Chemical compound COC(=O)C1=CC=C(O)C=C1 LXCFILQKKLGQFO-UHFFFAOYSA-N 0.000 description 1
- 150000007522 mineralic acids Chemical class 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- RMHJJUOPOWPRBP-UHFFFAOYSA-N naphthalene-1-carboxamide Chemical compound C1=CC=C2C(C(=O)N)=CC=CC2=C1 RMHJJUOPOWPRBP-UHFFFAOYSA-N 0.000 description 1
- 229910017604 nitric acid Inorganic materials 0.000 description 1
- 150000007530 organic bases Chemical class 0.000 description 1
- 244000045947 parasite Species 0.000 description 1
- 235000010482 polyoxyethylene sorbitan monooleate Nutrition 0.000 description 1
- 229920000053 polysorbate 80 Polymers 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- KZJWDPNRJALLNS-VJSFXXLFSA-N sitosterol Chemical compound C1C=C2C[C@@H](O)CC[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@H]([C@H](C)CC[C@@H](CC)C(C)C)[C@@]1(C)CC2 KZJWDPNRJALLNS-VJSFXXLFSA-N 0.000 description 1
- 229950005143 sitosterol Drugs 0.000 description 1
- AWUCVROLDVIAJX-GSVOUGTGSA-N sn-glycerol 3-phosphate Chemical compound OC[C@@H](O)COP(O)(O)=O AWUCVROLDVIAJX-GSVOUGTGSA-N 0.000 description 1
- 238000002791 soaking Methods 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 235000010199 sorbic acid Nutrition 0.000 description 1
- 239000004334 sorbic acid Substances 0.000 description 1
- 229940075582 sorbic acid Drugs 0.000 description 1
- 229910001220 stainless steel Inorganic materials 0.000 description 1
- 238000010561 standard procedure Methods 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- KDYFGRWQOYBRFD-UHFFFAOYSA-L succinate(2-) Chemical compound [O-]C(=O)CCC([O-])=O KDYFGRWQOYBRFD-UHFFFAOYSA-L 0.000 description 1
- 239000005720 sucrose Substances 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
- 230000004083 survival effect Effects 0.000 description 1
- 229940095064 tartrate Drugs 0.000 description 1
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 1
- 229910052723 transition metal Inorganic materials 0.000 description 1
- 150000003624 transition metals Chemical class 0.000 description 1
- 230000035899 viability Effects 0.000 description 1
- 239000011782 vitamin Substances 0.000 description 1
- 229940088594 vitamin Drugs 0.000 description 1
- 229930003231 vitamin Natural products 0.000 description 1
- 235000013343 vitamin Nutrition 0.000 description 1
- 150000003722 vitamin derivatives Chemical class 0.000 description 1
- 239000002023 wood Substances 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- 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
- C07D261/04—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
-
- 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
Landscapes
- Life Sciences & Earth Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Dentistry (AREA)
- Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Plant Pathology (AREA)
- General Health & Medical Sciences (AREA)
- Wood Science & Technology (AREA)
- Zoology (AREA)
- Environmental Sciences (AREA)
- Pest Control & Pesticides (AREA)
- Agronomy & Crop Science (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
Abstract
본 개시는 신규한 다이하이드로아이소옥사졸 유도체 화합물 및 이를 활성성분으로 함유하는 살충제 화합물에 관한 것으로, 일 구현예에 따른 화합물은 다양한 해충류, 특히 총채벌레목 및 나방목 해충류에 대해 우수한 살충 효과를 보이면서도 익충인 꿀벌에 안전하다.The present disclosure relates to a novel dihydroisoxazole derivative compound and an insecticidal compound containing the same as an active ingredient. The compound according to one embodiment has excellent insecticidal effects against various pests, especially thrips and moth insects. It is safe for bees, which are beneficial insects.
Description
본 개시는 신규한 다이하이드로아이소옥사졸 유도체 화합물 및 이를 포함하는 살충제 조성물에 관한 것이다.The present disclosure relates to novel dihydroisoxazole derivative compounds and pesticide compositions containing the same.
무척추 해충의 방제는 높은 작황 효율을 달성하는 데 있어서 매우 중요하다. 재배되고 있는 농경 작물 및 저장된 농경 작물에 대한 무척추 해충에 의한 피해는 생산율을 상당히 저하시킬 수 있으며, 이에 따라 소비자에게는 가격 인상을 전가시키게 된다. 산림, 온실 작물, 관상수, 묘목 작물, 저장 식품 및 섬유 제품, 가축, 가사, 잔디, 목재 제품, 및 공중 보건 및 동물 건강에 있어서의 무척추 해충의 방제도 또한 중요하다. 현재 다수의 제품이 이러한 목적을 위하여 시판되고 있지만, 더 효과적이고, 더 저렴하고, 덜 독성이며, 환경적으로 더 안정한 신규 화합물 또는 상이한 작용 방식을 갖는 신규 화합물에 대한 필요는 계속되고 있다.Control of invertebrate pests is very important in achieving high crop efficiency. Damage from invertebrate pests to growing and stored agricultural crops can significantly reduce production rates, resulting in increased prices passed on to consumers. Control of invertebrate pests in forests, greenhouse crops, ornamental trees, nursery crops, stored food and fiber products, livestock, housekeeping, turf, wood products, and for public and animal health is also important. Although a number of products are currently commercially available for this purpose, there continues to be a need for new compounds that are more effective, less expensive, less toxic, more environmentally stable, or have different modes of action.
대한민국 등록특허 KR 10-1151325 B1, KR 10-1416521 B1에는 다이하이드로아이소옥사졸 화합물의 유도체 및 이를 방제용으로 사용하는 기술에 대해 개시되어 있다.Korean registered patents KR 10-1151325 B1 and KR 10-1416521 B1 disclose derivatives of dihydroisoxazole compounds and techniques for using them for control purposes.
본 발명의 일 목적은 신규한 다이하이드로아이소옥사졸 유도체 화합물을 제공하는 것이다.One object of the present invention is to provide novel dihydroisoxazole derivative compounds.
본 발명의 다른 일 목적은 다이하이드로아이소옥사졸 유도체 화합물을 포함하는 살충제 조성물을 제공하는 것이다.Another object of the present invention is to provide a pesticide composition containing a dihydroisoxazole derivative compound.
본 발명의 다른 일 목적은 다이하이드로아이소옥사졸 유도체 화합물을 이용하여 해충을 방제하는 방법을 제공하는 것이다.Another object of the present invention is to provide a method for controlling pests using a dihydroisoxazole derivative compound.
상기 목적을 달성하기 위하여,In order to achieve the above purpose,
일 구현예는 하기 화학식 1로 표시되는 화합물, 이의 입체 이성질체, 이의 수화물, 또는 이의 염을 제공한다.One embodiment provides a compound represented by the following formula (1), a stereoisomer thereof, a hydrate thereof, or a salt thereof.
[화학식 1][Formula 1]
상기 화학식 1에서,In Formula 1,
R1은 각각 독립적으로 -H, 할로겐, C1-5알킬, 또는 C1-5할로알킬이고;each R 1 is independently -H, halogen, C 1-5 alkyl, or C 1-5 haloalkyl;
R2는 -H, 할로겐, C1-5알킬, 또는 C1-5할로알킬이고;R 2 is -H, halogen, C 1-5 alkyl, or C 1-5 haloalkyl;
R3는 할로겐, C1-5알킬, 및 C1-5할로알킬로 이루어지는 군으로부터 선택되는 1종 이상의 치환기가 5개 이하로 치환된, C2-10알킬, C3-10사이클로알킬, C3-10사이클로알킬C2-10알킬, 또는 N, O 및 S로 이루어지는 군으로부터 선택되는 1종 이상의 헤테로원자를 포함하는 3 내지 10원자의 헤테로사이클로알킬이고;R 3 is C 2-10 alkyl, C 3-10 cycloalkyl, C substituted with 5 or fewer substituents selected from the group consisting of halogen, C 1-5 alkyl, and C 1-5 haloalkyl. 3-10 Cycloalkyl C 2-10 alkyl, or heterocycloalkyl of 3 to 10 atoms containing at least one heteroatom selected from the group consisting of N, O and S;
Q는 또는 이고;Q is or ego;
R4a 및 R4b는 각각 독립적으로 -H, 할로겐, C1- 5알킬, 또는 C1- 5할로알킬이고; 및R 4a and R 4b are each independently -H, halogen, C 1-5 alkyl , or C 1-5 haloalkyl ; and
x는 1 내지 5의 정수일 수 있다.x may be an integer from 1 to 5.
다른 일 구현예는 상기 화합물, 이의 입체 이성질체, 이의 수화물, 및 이의 염을 활성성분으로 함유하는 살충제 조성물을 제공한다.Another embodiment provides a pesticide composition containing the above compound, its stereoisomer, its hydrate, and its salt as active ingredients.
다른 일 구현예는 상기 화합물, 이의 입체 이성질체, 이의 수화물, 및 이의 염을 농작물 또는 이의 서식지에 처리하는 단계를 포함하는 해충을 방제하는 방법을 제공한다.Another embodiment provides a method for controlling pests comprising treating crops or their habitats with the compound, its stereoisomer, its hydrate, and its salt.
다른 일 구현예는 해충의 살충 또는 방제에 사용하기 위한 상기 화합물, 이의 입체 이성질체, 이의 수화물, 및 이의 염의 용도(use)를 제공한다.Another embodiment provides the use of the compound, its stereoisomer, its hydrate, and its salt for use in insecticide or control.
본 개시는 신규한 다이하이드로아이소옥사졸 유도체 화합물 및 이를 활성성분으로 함유하는 살충제 화합물에 관한 것으로, 일 구현예에 따른 화합물은 다양한 해충류, 특히 총채벌레목 및 나방목 해충류에 대해 우수한 살충 효과를 보이면서도 익충인 꿀벌에 안전하다.The present disclosure relates to a novel dihydroisoxazole derivative compound and an insecticidal compound containing the same as an active ingredient. The compound according to one embodiment has excellent insecticidal effects against various pests, especially thrips and moth insects. It is safe for bees, which are beneficial insects.
이하, 본 발명을 상세하게 설명한다.Hereinafter, the present invention will be described in detail.
한편, 본 발명의 실시 형태는 여러 가지 다른 형태로 변형될 수 있으며, 본 발명의 범위가 이하 설명하는 실시 형태로 한정되는 것은 아니다. 또한, 본 발명의 실시 형태는 당해 기술분야에서 평균적인 지식을 가진 자에게 본 발명을 더욱 완전하게 설명하기 위해서 제공되는 것이다. 나아가, 명세서 전체에서 어떤 구성요소를 "포함"한다는 것은 특별히 반대되는 기재가 없는 한 다른 구성요소를 제외하는 것이 아니라 다른 구성요소를 더 포함할 수 있다는 것을 의미한다.Meanwhile, the embodiments of the present invention may be modified into various other forms, and the scope of the present invention is not limited to the embodiments described below. Additionally, the embodiments of the present invention are provided to more completely explain the present invention to those with average knowledge in the relevant technical field. Furthermore, “including” a certain element throughout the specification means that other elements may be further included rather than excluding other elements, unless specifically stated to the contrary.
이하에서, "치환"은 각각의 치환기가 1개 이상 치환되는 경우도 포함하는 의미이다. 예를 들어, 치환기가 치환될 때는 10개 이하, 5개 이하, 또는 3개 이하로 치환될 수도 있다.Hereinafter, “substitution” is meant to include cases where one or more of each substituent is substituted. For example, when substituents are substituted, 10 or fewer, 5 or fewer, or 3 or fewer substituents may be substituted.
본 개시의 일 구현예는 하기 화학식 1로 표시되는 화합물, 이의 입체 이성질체, 이의 수화물, 또는 이의 염을 제공한다.One embodiment of the present disclosure provides a compound represented by the following formula (1), a stereoisomer thereof, a hydrate thereof, or a salt thereof.
[화학식 1][Formula 1]
상기 화학식 1에서,In Formula 1,
R1은 각각 독립적으로 -H, 할로겐, C1-5알킬, 또는 C1-5할로알킬이고;each R 1 is independently -H, halogen, C 1-5 alkyl, or C 1-5 haloalkyl;
R2는 -H, 할로겐, C1-5알킬, 또는 C1-5할로알킬이고;R 2 is -H, halogen, C 1-5 alkyl, or C 1-5 haloalkyl;
R3는 할로겐, C1-5알킬, 및 C1-5할로알킬로 이루어지는 군으로부터 선택되는 1종 이상의 치환기가 5개 이하로 치환된, C2-10알킬, C3-10사이클로알킬, C3-10사이클로알킬C2-10알킬, 또는 N, O 및 S로 이루어지는 군으로부터 선택되는 1종 이상의 헤테로원자를 포함하는 3 내지 10원자의 헤테로사이클로알킬이고;R 3 is C 2-10 alkyl, C 3-10 cycloalkyl, C substituted with 5 or fewer substituents selected from the group consisting of halogen, C 1-5 alkyl, and C 1-5 haloalkyl. 3-10 Cycloalkyl C 2-10 alkyl, or heterocycloalkyl of 3 to 10 atoms containing at least one heteroatom selected from the group consisting of N, O and S;
Q는 또는 이고;Q is or ego;
R4a 및 R4b는 각각 독립적으로 -H, 할로겐, C1- 5알킬, 또는 C1- 5할로알킬이고; 및R 4a and R 4b are each independently -H, halogen, C 1-5 alkyl , or C 1-5 haloalkyl ; and
x는 1 내지 5의 정수이다.x is an integer from 1 to 5.
상기에서 "할로알킬"은 알킬기에 할로겐이 1개 이상, 2개 이상, 5개 이하, 3개 이하로 치환된 화합물일 수 있다.In the above, “haloalkyl” may be a compound in which the alkyl group is substituted with 1 or more, 2 or more, 5 or less, or 3 or less halogens.
상기 R3의 C2- 10알킬, C3- 10사이클로알킬, C3- 10사이클로알킬C2 - 10알킬, 또는 N, O 및 S로 이루어지는 군으로부터 선택되는 1종 이상의 헤테로원자를 포함하는 3 내지 10원자의 헤테로사이클로알킬은 할로겐, C1- 5알킬, 및 C1- 5할로알킬로 이루어지는 군으로부터 선택되는 1종 이상의 치환기가 4개 이하, 3개 이하, 2개 이하, 2개 또는 3개, 1개 내지 3개 치환될 수도 있다.3 containing at least one heteroatom selected from the group consisting of C 2-10 alkyl, C 3-10 cycloalkyl, C 3-10 cycloalkylC 2-10 alkyl , or N, O , and S of the above R 3 Heterocycloalkyl of 1 to 10 atoms has 4 or less, 3 or less, 2 or less, 2 or 3 of one or more substituents selected from the group consisting of halogen, C 1- 5 alkyl, and C 1- 5 haloalkyl. 1 to 3 may be substituted.
또는, 상기 R1은 각각 독립적으로 -H, 할로겐, 또는 C1- 3할로알킬이고;Alternatively, each R 1 is independently -H, halogen, or C 1-3 haloalkyl;
상기 R2는 -H, 할로겐, 또는 C1-3할로알킬이고;R 2 is -H, halogen, or C 1-3 haloalkyl;
상기 Q는 또는 이고;The above Q is or ego;
상기 R4a 및 R4b는 각각 독립적으로 -H, 할로겐, 또는 C1- 3알킬이고; 및R 4a and R 4b are each independently -H, halogen , or C 1-3 alkyl; and
상기 x는 1 내지 3의 정수일 수 있다.The x may be an integer from 1 to 3.
또는, 상기 R1은 각각 독립적으로 할로겐, 또는 -CF3이고;Alternatively, each R 1 is independently halogen or -CF 3 ;
상기 R2는 -CF3이고;wherein R 2 is -CF 3 ;
상기 Q는 또는 이고; 및The above Q is or ego; and
상기 x는 1 내지 3의 정수일 수 있다.The x may be an integer from 1 to 3.
또는, 상기 R3는 할로겐, C1-3알킬, 및 C1-3할로알킬로 이루어지는 군으로부터 선택되는 1종 이상의 치환기가 5개 이하로 치환된, C2-6알킬, C3-6사이클로알킬, C3-6사이클로알킬C2-6알킬, 또는 N, O 및 S로 이루어지는 군으로부터 선택되는 1종 이상의 헤테로원자를 포함하는 3 내지 6 원자의 헤테로사이클로알킬일 수 있다.Alternatively, R 3 is C 2-6 alkyl, C 3-6 cyclo substituted with 5 or less substituents selected from the group consisting of halogen, C 1-3 alkyl, and C 1-3 haloalkyl. It may be alkyl, C 3-6 cycloalkyl, C 2-6 alkyl, or 3 to 6-membered heterocycloalkyl containing at least one heteroatom selected from the group consisting of N, O and S.
상기 R3의 C2-6알킬, C3-6사이클로알킬, C3-6사이클로알킬C2-6알킬, 또는 N, O 및 S로 이루어지는 군으로부터 선택되는 1종 이상의 헤테로원자를 포함하는 3 내지 6 원자의 헤테로사이클로알킬은 할로겐, C1- 3알킬, 및 C1- 3할로알킬로 이루어지는 군으로부터 선택되는 1종 이상의 치환기가 4개 이하, 3개 이하, 2개 이하, 2개 또는 3개, 1개 내지 3개 치환될 수도 있다.3 containing at least one heteroatom selected from the group consisting of C 2-6 alkyl, C 3-6 cycloalkyl, C 3-6 cycloalkylC 2-6 alkyl, or N, O, and S of the above R 3 Heterocycloalkyl of 6 to 6 atoms has 4 or less, 3 or less, 2 or less, 2 or 3 of one or more substituents selected from the group consisting of halogen, C 1-3 alkyl , and C 1-3 haloalkyl . 1 to 3 may be substituted.
또는, R3는 , , , , , , , , , , , , , , 또는 일 수 있고,Or, R 3 is , , , , , , , , , , , , , , or It can be,
이때 상기 X는 각각 독립적으로 I, Br, Cl, 또는 F이다.At this time, the X is each independently I, Br, Cl, or F.
또는, 상기 R3는 5개 이하의 동일 또는 서로 다른 할로겐이 치환된, C2- 6알킬, C3- 6사이클로알킬, C3- 6사이클로알킬C2 - 6알킬, 또는 N, O 및 S로 이루어지는 군으로부터 선택되는 1종 이상의 헤테로원자를 포함하는 3 내지 6 원자의 헤테로사이클로알킬일 수 있다.Alternatively, R 3 is C 2-6 alkyl, C 3-6 cycloalkyl, C 3-6 cycloalkyl C 2-6 alkyl substituted with up to 5 identical or different halogens , or N , O and S. It may be a 3 to 6-membered heterocycloalkyl containing one or more heteroatoms selected from the group consisting of.
상기 R3의 C2-6알킬, C3-6사이클로알킬, C3-6사이클로알킬C2-6알킬, 또는 N, O 및 S로 이루어지는 군으로부터 선택되는 1종 이상의 헤테로원자를 포함하는 3 내지 6 원자의 헤테로사이클로알킬은 동일 또는 서로 다른 할로겐이 4개 이하, 3개 이하, 2개 이하, 2개 또는 3개, 1개 내지 3개 치환될 수도 있다.3 containing at least one heteroatom selected from the group consisting of C 2-6 alkyl, C 3-6 cycloalkyl, C 3-6 cycloalkylC 2-6 alkyl, or N, O, and S of the above R 3 Heterocycloalkyl of 6 to 6 atoms may be substituted with 4 or less, 3 or less, 2 or less, 2 or 3, or 1 to 3 of the same or different halogens.
또는, 상기 화학식 1로 표시되는 화합물은,Alternatively, the compound represented by Formula 1 is:
(1) N-(2-클로로에틸)-4-(5-(3,5-다이클로로페닐)-5-(트리플루오로메틸)-4,5-다이하이드로아이소옥사졸-3-일)-2-메틸벤즈아마이드;(1) N-(2-chloroethyl)-4-(5-(3,5-dichlorophenyl)-5-(trifluoromethyl)-4,5-dihydroisoxazol-3-yl) -2-methylbenzamide;
(2) N-(1-클로로프로판-2-일)-4-(5-(3,5-다이클로로페닐)-5-(트리플루오로메틸)-4,5-다이하이드로아이소옥사졸-3-일)-2-메틸벤즈아마이드;(2) N-(1-chloropropan-2-yl)-4-(5-(3,5-dichlorophenyl)-5-(trifluoromethyl)-4,5-dihydroisoxazole- 3-yl)-2-methylbenzamide;
(3) N-(2-클로로프로필)-4-(5-(3,5-다이클로로페닐)-5-(트리플루오로메틸)-4,5-다이하이드로아이소옥사졸-3-일)-2-메틸벤즈아마이드;(3) N-(2-chloropropyl)-4-(5-(3,5-dichlorophenyl)-5-(trifluoromethyl)-4,5-dihydroisoxazol-3-yl) -2-methylbenzamide;
(4) 4-(5-(3,5-다이클로로페닐)-5-(트리플루오로메틸)-4,5-다이하이드로아이소옥사졸-3-일)-N-(1,3-다이클로로프로판-2-일)-2-메틸벤즈아마이드;(4) 4-(5-(3,5-dichlorophenyl)-5-(trifluoromethyl)-4,5-dihydroisoxazol-3-yl)-N-(1,3-di Chloropropan-2-yl)-2-methylbenzamide;
(5) N-(1-(클로로메틸)사이클로프로필)-4-(5-(3,5-다이클로로페닐)-5-(트리플루오로메틸)-4,5-다이하이드로아이소옥사졸-3-일)-2-메틸벤즈아마이드;(5) N-(1-(chloromethyl)cyclopropyl)-4-(5-(3,5-dichlorophenyl)-5-(trifluoromethyl)-4,5-dihydroisoxazole- 3-yl)-2-methylbenzamide;
(6) N-(2-클로로-3,3,3-트리플루오로프로필)-4-(5-(3,5-다이클로로페닐)-5-(트리플루오로메틸)-4,5-다이하이드로아이소옥사졸-3-일)-2-메틸벤즈아마이드;(6) N-(2-chloro-3,3,3-trifluoropropyl)-4-(5-(3,5-dichlorophenyl)-5-(trifluoromethyl)-4,5- dihydroisoxazol-3-yl)-2-methylbenzamide;
(7) N-(3-클로로-1,1,1-트리플루오로프로판-2-일)-4-(5-(3,5-다이클로로페닐)-5-(트리플루오로메틸)-4,5-다이하이드로아이소옥사졸-3-일)-2-메틸벤즈아마이드;(7) N-(3-chloro-1,1,1-trifluoropropan-2-yl)-4-(5-(3,5-dichlorophenyl)-5-(trifluoromethyl)- 4,5-dihydroisoxazol-3-yl)-2-methylbenzamide;
(8) N-(1-(클로로메틸)사이클로뷰틸)-4-(5-(3,5-다이클로로페닐)-5-(트리플루오로메틸)-4,5-다이하이드로아이소옥사졸-3-일)-2-메틸벤즈아마이드;(8) N-(1-(chloromethyl)cyclobutyl)-4-(5-(3,5-dichlorophenyl)-5-(trifluoromethyl)-4,5-dihydroisoxazole- 3-yl)-2-methylbenzamide;
(9) N-(2-클로로에틸)-4-(5-(3,5-다이클로로-4-플루오로페닐)-5-(트리플루오로메틸)-4,5-다이하이드로아이소옥사졸-3-일)-2-메틸벤즈아마이드;(9) N-(2-chloroethyl)-4-(5-(3,5-dichloro-4-fluorophenyl)-5-(trifluoromethyl)-4,5-dihydroisoxazole -3-yl)-2-methylbenzamide;
(10) 4-(5-(3-클로로-5-(트리플루오로메틸)페닐)-5-(트리플루오로메틸)-4,5-다이하이드로아이소옥사졸-3-일)-N-(2-클로로에틸)-2-메틸벤즈아마이드;(10) 4-(5-(3-chloro-5-(trifluoromethyl)phenyl)-5-(trifluoromethyl)-4,5-dihydroisoxazol-3-yl)-N- (2-chloroethyl)-2-methylbenzamide;
(11) N-(2-브로모에틸)-4-(5-(3,5-다이클로로페닐)-5-(트리플루오로메틸)-4,5-다이하이드로아이소옥사졸-3-일)-2-메틸벤즈아마이드;(11) N-(2-bromoethyl)-4-(5-(3,5-dichlorophenyl)-5-(trifluoromethyl)-4,5-dihydroisoxazol-3-yl )-2-methylbenzamide;
(12) 4-(5-(3,5-다이클로로페닐)-5-(트리플루오로메틸)-4,5-다이하이드로아이소옥사졸-3-일)-N-(2-플루오로에틸)-2-메틸벤즈아마이드;(12) 4-(5-(3,5-dichlorophenyl)-5-(trifluoromethyl)-4,5-dihydroisoxazol-3-yl)-N-(2-fluoroethyl )-2-methylbenzamide;
(13) N-(2-클로로에틸)-4-(5-(4-클로로페닐)-5-(트리플루오로메틸)-4,5-다이하이드로아이소옥사졸-3-일)-2-메틸벤즈아마이드;(13) N-(2-chloroethyl)-4-(5-(4-chlorophenyl)-5-(trifluoromethyl)-4,5-dihydroisoxazol-3-yl)-2- methylbenzamide;
(14) 4-(5-(4-클로로페닐)-5-(트리플루오로메틸)-4,5-다이하이드로아이소옥사졸-3-일)-N-(2-플루오로에틸)-2-메틸벤즈아마이드;(14) 4-(5-(4-chlorophenyl)-5-(trifluoromethyl)-4,5-dihydroisoxazol-3-yl)-N-(2-fluoroethyl)-2 -methylbenzamide;
(15) N-(2-플루오로에틸)-4-(5-(4-플루오로페닐)-5-(트리플루오로메틸)-4,5-다이하이드로아이소옥사졸-3-일)-2-메틸벤즈아마이드;(15) N-(2-fluoroethyl)-4-(5-(4-fluorophenyl)-5-(trifluoromethyl)-4,5-dihydroisoxazol-3-yl)- 2-methylbenzamide;
(16) 4-(5-(3,5-다이클로로-4-플루오로페닐)-5-(트리플루오로메틸)-4,5-다이하이드로아이소옥사졸-3-일)-N-(2-플루오로에틸)-2-메틸벤즈아마이드;(16) 4-(5-(3,5-dichloro-4-fluorophenyl)-5-(trifluoromethyl)-4,5-dihydroisoxazol-3-yl)-N-( 2-fluoroethyl)-2-methylbenzamide;
(17) 4-(5-(3,5-다이플루오로페닐)-5-(트리플루오로메틸)-4,5-다이하이드로아이소옥사졸-3-일)-N-(2-플루오로에틸)-2-메틸벤즈아마이드;(17) 4-(5-(3,5-difluorophenyl)-5-(trifluoromethyl)-4,5-dihydroisoxazol-3-yl)-N-(2-fluoro ethyl)-2-methylbenzamide;
(18) 4-(5-(3-클로로-5-(트리플루오로메틸)페닐)-5-(트리플루오로메틸)-4,5-다이하이드로아이소옥사졸-3-일)-N-(2-플루오로에틸)-2-메틸벤즈아마이드;(18) 4-(5-(3-chloro-5-(trifluoromethyl)phenyl)-5-(trifluoromethyl)-4,5-dihydroisoxazol-3-yl)-N- (2-fluoroethyl)-2-methylbenzamide;
(19) N-((1-(클로로메틸)사이클로프로필)메틸)-4-(5-(3,5-다이클로로페닐)-5-(트리플루오로메틸)-4,5-다이하이드로아이소옥사졸-3-일)-2-메틸벤즈아마이드;(19) N-((1-(chloromethyl)cyclopropyl)methyl)-4-(5-(3,5-dichlorophenyl)-5-(trifluoromethyl)-4,5-dihydroi Sooxazol-3-yl)-2-methylbenzamide;
(20) N-((1-(클로로메틸)사이클로뷰틸)메틸)-4-(5-(3,5-다이클로로페닐)-5-(트리플루오로메틸)-4,5-다이하이드로아이소옥사졸-3-일)-2-메틸벤즈아마이드;(20) N-((1-(chloromethyl)cyclobutyl)methyl)-4-(5-(3,5-dichlorophenyl)-5-(trifluoromethyl)-4,5-dihydroi Sooxazol-3-yl)-2-methylbenzamide;
(21) N-(3-클로로프로필)-4-(5-(3,5-다이클로로페닐)-5-(트리플루오로메틸)-4,5-다이하이드로아이소옥사졸-3-일)-2-메틸벤즈아마이드;(21) N-(3-chloropropyl)-4-(5-(3,5-dichlorophenyl)-5-(trifluoromethyl)-4,5-dihydroisoxazol-3-yl) -2-methylbenzamide;
(22) N-(4-클로로뷰틸)-4-(5-(3,5-다이클로로페닐)-5-(트리플루오로메틸)-4,5-다이하이드로아이소옥사졸-3-일)-2-메틸벤즈아마이드;(22) N-(4-chlorobutyl)-4-(5-(3,5-dichlorophenyl)-5-(trifluoromethyl)-4,5-dihydroisoxazol-3-yl) -2-methylbenzamide;
(23) N-(2-클로로에틸)-4-(5-(3,5-다이클로로페닐)-5-(트리플루오로메틸)-4,5-다이하이드로아이소옥사졸-3-일)-1-나프트아마이드;(23) N-(2-chloroethyl)-4-(5-(3,5-dichlorophenyl)-5-(trifluoromethyl)-4,5-dihydroisoxazol-3-yl) -1-naphthamide;
(24) N-(2-클로로프로필)-4-(5-(3,5-다이클로로페닐)-5-(트리플루오로메틸)-4,5-다이하이드로아이소옥사졸-3-일)-1-나프트아마이드;(24) N-(2-chloropropyl)-4-(5-(3,5-dichlorophenyl)-5-(trifluoromethyl)-4,5-dihydroisoxazol-3-yl) -1-naphthamide;
(25) 4-(5-(3,5-다이클로로페닐)-5-(트리플루오로메틸)-4,5-다이하이드로아이소옥사졸-3-일)-N-(1,3-다이클로로프로판-2-일)-1-나프트아마이드;(25) 4-(5-(3,5-dichlorophenyl)-5-(trifluoromethyl)-4,5-dihydroisoxazol-3-yl)-N-(1,3-di Chloropropan-2-yl)-1-naphthamide;
(26) N-(1-(클로로메틸)사이클로프로필)-4-(5-(3,5-다이클로로페닐)-5-(트리플루오로메틸)-4,5-다이하이드로아이소옥사졸-3-일)-1-나프트아마이드;(26) N-(1-(chloromethyl)cyclopropyl)-4-(5-(3,5-dichlorophenyl)-5-(trifluoromethyl)-4,5-dihydroisoxazole- 3-yl)-1-naphthamide;
(27) N-(3-클로로-1,1,1-트리플루오로프로판-2-일)-4-(5-(3,5-다이클로로페닐)-5-(트리플루오로메틸)-4,5-다이하이드로아이소옥사졸-3-일)-1-나프트아마이드;(27) N-(3-chloro-1,1,1-trifluoropropan-2-yl)-4-(5-(3,5-dichlorophenyl)-5-(trifluoromethyl)- 4,5-dihydroisoxazol-3-yl)-1-naphthamide;
(28) N-(3-(클로로메틸)옥세탄-3-일)-4-(5-(3,5-다이클로로페닐)-5-(트리플루오로메틸)-4,5-다이하이드로아이소옥사졸-3-일)-1-나프트아마이드;(28) N-(3-(chloromethyl)oxetan-3-yl)-4-(5-(3,5-dichlorophenyl)-5-(trifluoromethyl)-4,5-dihydro isoxazol-3-yl)-1-naphthamide;
(29) N-(2-클로로에틸)-4-(5-(3,5-다이클로로-4-플루오로페닐)-5-(트리플루오로메틸)-4,5-다이하이드로아이소옥사졸-3-일)-1-나트프아마이드;(29) N-(2-chloroethyl)-4-(5-(3,5-dichloro-4-fluorophenyl)-5-(trifluoromethyl)-4,5-dihydroisoxazole -3-day)-1-natphamide;
(30) 4-(5-(3-클로로-5-(트리플루오로메틸)페닐)-5-(트리플루오로메틸)-4,5-다이하이드로아이소옥사졸-3-일)-N-(2-클로로에틸)-1-나프트아마이드;(30) 4-(5-(3-chloro-5-(trifluoromethyl)phenyl)-5-(trifluoromethyl)-4,5-dihydroisoxazol-3-yl)-N- (2-chloroethyl)-1-naphthamide;
(31) N-(2-브로모에틸)-4-(5-(3,5-다이클로로페닐)-5-(트리플루오로메틸)-4,5-다이하이드로아이소옥사졸-3-일)-1-나프트아마이드;(31) N-(2-bromoethyl)-4-(5-(3,5-dichlorophenyl)-5-(trifluoromethyl)-4,5-dihydroisoxazol-3-yl )-1-naphthamide;
(32) 4-(5-(3,5-다이클로로페닐)-5-(트리플루오로메틸)-4,5-다이하이드로아이소옥사졸-3-일)-N-(2-플루오로에틸)-1-나프트아마이드;(32) 4-(5-(3,5-dichlorophenyl)-5-(trifluoromethyl)-4,5-dihydroisoxazol-3-yl)-N-(2-fluoroethyl )-1-naphthamide;
(33) N-(2-클로로에틸)-4-(5-(3,5-다이플루오로페닐)-5-(트리플루오로메틸)-4,5-다이하이드로아이소옥사졸-3-일)-1-나프트아마이드;(33) N-(2-chloroethyl)-4-(5-(3,5-difluorophenyl)-5-(trifluoromethyl)-4,5-dihydroisoxazol-3-yl )-1-naphthamide;
(34) N-(2-클로로에틸)-4-(5-(4-클로로페닐)-5-(트리플루오로메틸)-4,5-다이하이드로아이소옥사졸-3-일)-1-나프트아마이드;(34) N-(2-chloroethyl)-4-(5-(4-chlorophenyl)-5-(trifluoromethyl)-4,5-dihydroisoxazol-3-yl)-1- naphthamide;
(35) 4-(5-(4-클로로페닐)-5-(트리플루오로메틸)-4,5-다이하이드로아이소옥사졸-3-일)-N-(2-플루오로에틸)-1-나프트아마이드;(35) 4-(5-(4-chlorophenyl)-5-(trifluoromethyl)-4,5-dihydroisoxazol-3-yl)-N-(2-fluoroethyl)-1 -Naphthamide;
(36) N-(2-플루오로에틸)-4-(5-(4-플루오로페닐)-5-(트리플루오로메틸)-4,5-다이하이드로아이소옥사졸-3-일)-1-나프트아마이드;(36) N-(2-fluoroethyl)-4-(5-(4-fluorophenyl)-5-(trifluoromethyl)-4,5-dihydroisoxazol-3-yl)- 1-naphthamide;
(37) 4-(5-(3,5-다이클로로-4-플루오로페닐)-5-(트리플루오로메틸)-4,5-다이하이드로아이소옥사졸-3-일)-N-(2-플루오로에틸)-1-나프트아마이드;(37) 4-(5-(3,5-dichloro-4-fluorophenyl)-5-(trifluoromethyl)-4,5-dihydroisoxazol-3-yl)-N-( 2-fluoroethyl)-1-naphthamide;
(38) 4-(5-(3,5-다이플루오로페닐)-5-(트리플루오로메틸)-4,5-다이하이드로아이소옥사졸-3-일)-N-(2-플루오로에틸)-1-나프트아마이드;(38) 4-(5-(3,5-difluorophenyl)-5-(trifluoromethyl)-4,5-dihydroisoxazol-3-yl)-N-(2-fluoro ethyl)-1-naphthamide;
(39) 4-(5-(3-클로로-5-(트리플루오로메틸)페닐)-5-(트리플루오로메틸)-4,5-다이하이드로아이소옥사졸-3-일)-N-(2-플루오로에틸)-1-나프트아마이드;(39) 4-(5-(3-chloro-5-(trifluoromethyl)phenyl)-5-(trifluoromethyl)-4,5-dihydroisoxazol-3-yl)-N- (2-fluoroethyl)-1-naphthamide;
(40) N-((1-(클로로메틸)사이클로뷰틸)메틸)-4-(5-(3,5-다이클로로페닐)-5-(트리플루오로메틸)-4,5-다이하이드로아이소옥사졸-3-일)-1-나프트아마이드;(40) N-((1-(chloromethyl)cyclobutyl)methyl)-4-(5-(3,5-dichlorophenyl)-5-(trifluoromethyl)-4,5-dihydroi Sooxazol-3-yl)-1-naphthamide;
(41) N-(2,5-다이클로로펜틸)-4-(5-(3,5-다이클로로페닐)-5-(트리플루오로메틸)-4,5-다이하이드로아이소옥사졸-3-일)-1-나프트아마이드;(41) N-(2,5-dichloropentyl)-4-(5-(3,5-dichlorophenyl)-5-(trifluoromethyl)-4,5-dihydroisoxazole-3 -1)-1-naphthamide;
(42) N-(3-클로로프로필)-4-(5-(3,5-다이클로로페닐)-5-(트리플루오로메틸)-4,5-다이하이드로아이소옥사졸-3-일)-1-나프트아마이드; 또는(42) N-(3-chloropropyl)-4-(5-(3,5-dichlorophenyl)-5-(trifluoromethyl)-4,5-dihydroisoxazol-3-yl) -1-naphthamide; or
(43) N-(4-클로로뷰틸)-4-(5-(3,5-다이클로로페닐)-5-(트리플루오로메틸)-4,5-다이하이드로아이소옥사졸-3-일)-1-나프트아마이드일 수 있다.(43) N-(4-chlorobutyl)-4-(5-(3,5-dichlorophenyl)-5-(trifluoromethyl)-4,5-dihydroisoxazol-3-yl) It may be -1-naphthamide.
상기 화합물의 염은 예를 들어 농약학적으로 허용가능한 염일 수 있다. 농약학적으로 허용가능한 염에는, 농약학적으로 허용가능한 무기성 또는 유기성 염기 및 산으로부터 유래된 것이 포함된다. 적합한 염에는, 리튬, 나트륨 또는 칼륨 등의 알칼리 금속, 칼슘, 마그네슘 및 바륨 등의 알칼리토금속을 포함하는 것 이 포함된다. 이에 제한되는 것은 아니나, 망간, 구리, 아연 및 철을 비롯한 전이 금속을 포함하는 염도 또한 적합하다. 게다가, 암모늄 양이온 및 수소 원자 중 하나 이상이 알킬 또는 아릴기로 대체된 치환 된 암모늄 양이온을 포함하는 염도 본 발명에 포함된다. 이에 제한되지는 않으나 히드로할라이드 산 (HCl, HBr, HF, HI), 황산, 질산, 인산 등을 비롯한 무기산에서 유래된 염이 특히 적합하다. 적합한 무기 염은 또한 이에 제한되는 것은 아니나, 바이카르보네이트 및 카르보 네이트 염을 포함한다. 일부 구현예에서, 농약학적으로 허용가능한 염의 예는 이에 제한되는 것은 아니나, 말레에이트, 디말레에이트, 푸마레이트, 토실레이트, 메탄술포네이트, 아세테이트, 시트레이트, 말로네이트, 타르트레이트, 숙시네이트, 벤조에이트, 아스코르베이트, α-케토글루타레이트 및 α-글리세로포스페이트를 포함한 유기산으로 형성된 유기산 부가염이다. 물론, 기타 허용가능한 유기산이 이용되어도 된다. 화합물의 알칼리 금속 (예, 나트륨, 칼륨 또는 리튬) 또는 알칼리토금속 (예, 칼슘) 염이 또한 알칼리 금속 또는 알칼리토금속의 히드록시드로 화합물 상 충분히 산성인 잔기를 반응시킴으로써 제조될 수 있다. 농약학적으로 허용가능한 염은 당업자에게 익히 공지된 표준 절차를 이용하여, 예를 들면 아민과 같은 충분히 염기성인 화합물을 화합물에 존재하는 적당한 산 관능기와 반응시킴으로써, 또는 적절한 산을 적절한 염기성 관능기와 반응시킴으로써 수득될 수도 있다.The salt of the compound may be, for example, an agrochemically acceptable salt. Agrochemically acceptable salts include those derived from agrochemically acceptable inorganic or organic bases and acids. Suitable salts include those containing alkali metals such as lithium, sodium or potassium, and alkaline earth metals such as calcium, magnesium and barium. Salts containing transition metals including, but not limited to, manganese, copper, zinc and iron are also suitable. Furthermore, salts comprising the ammonium cation and a substituted ammonium cation in which at least one of the hydrogen atoms is replaced with an alkyl or aryl group are also encompassed by the present invention. Salts derived from inorganic acids, including but not limited to hydrohalide acids (HCl, HBr, HF, HI), sulfuric acid, nitric acid, phosphoric acid, etc., are particularly suitable. Suitable inorganic salts also include, but are not limited to, bicarbonate and carbonate salts. In some embodiments, examples of agrochemically acceptable salts include, but are not limited to, maleate, dimaleate, fumarate, tosylate, methanesulfonate, acetate, citrate, malonate, tartrate, succinate, It is an organic acid addition salt formed from organic acids including benzoate, ascorbate, α-ketoglutarate, and α-glycerophosphate. Of course, other acceptable organic acids may be used. Alkali metal (e.g., sodium, potassium or lithium) or alkaline earth metal (e.g., calcium) salts of the compounds can also be prepared by reacting sufficiently acidic moieties on the compounds with hydroxides of alkali or alkaline earth metals. Agrochemically acceptable salts can be prepared using standard procedures well known to those skilled in the art, for example, by reacting a sufficiently basic compound, such as an amine, with an appropriate acid functionality present in the compound, or by reacting an appropriate acid with an appropriate basic functionality. may be obtained.
다른 일 구현예는 상기 화합물, 이의 입체 이성질체, 이의 수화물, 및 이의 염으로부터 선택되는 1종 이상의 화합물을 활성성분으로 함유하는 살충제 조성물을 제공한다.Another embodiment provides a pesticide composition containing as an active ingredient one or more compounds selected from the above compounds, stereoisomers thereof, hydrates thereof, and salts thereof.
일 실시예에서, 상기 살충제 조성물은 살충제 조성물에 통상적으로 첨가되는 첨가제를 더 포함할 수 있으며, 예를 들어 계면활성제, 고상 희석제, 액상 희석제, 또는 살충활성을 갖는 다른 물질을 더 포함할 수도 있으며, 이에 제한되지 않는다.In one embodiment, the pesticide composition may further include additives commonly added to pesticide compositions, for example, a surfactant, a solid diluent, a liquid diluent, or other substances with insecticidal activity, It is not limited to this.
일 실시예에서, 상기 살충제 조성물은 분무 조성물, 미끼 조성물, 또는 트랩용 조성물일 수도 있다.In one embodiment, the pesticide composition may be a spray composition, a bait composition, or a trap composition.
일 실시예에서, 상기 살충제 조성물은 무척추 해충 또는 무척추 기생충에 대한 살충활성을 가질 수 있다. 또는 예를 들어 바퀴벌레, 개미, 흰개미, 모기, 먹파리, 침파리, 사슴파리, 말파리, 말벌, 땅벌, 호박벌, 진드기, 거미, 개미, 나방에 대해 살충활성을 가질 수 있다.In one embodiment, the pesticide composition may have insecticidal activity against invertebrate pests or invertebrate parasites. Or, for example, it may have insecticidal activity against cockroaches, ants, termites, mosquitoes, meal flies, spit flies, deer flies, horse flies, wasps, bumblebees, bumblebees, ticks, spiders, ants, and moths.
구체적으로, 일 실시예에서 상기 살충제 조성물은 총채벌레목 및/또는 나방목 해충에 대해 살충활성을 가질 수 있으며, 예를 들어 꽃노랑총채벌레(Frankliniella occidentalis), 담배총채벌레(F. tenuicornis), 대만총채벌레(F. intonsa), 백합총채벌레(F. lilivora), 오이총채벌레(Thrips palmi Karny), 파총채벌레(Thrips tabaci Lindeman), 배추좀나방(Plutella xylostella), 담배거세미나방(Spodoptera litura), 열대거세미나방(Spodoptera frugiperda), 파밤나방(Spodoptera exigua), 또는 콩명나방(Maruca vitrta)에 대해 살충활성을 가질 수 있다.Specifically, in one embodiment, the pesticide composition may have insecticidal activity against thrips and/or lepidopteran pests, such as yellow flower thrips ( Frankliniella occidentalis ), tobacco thrips ( F. tenuicornis ), Taiwan thrips ( F. intonsa ), lily thrips ( F. lilivora ), cucumber thrips ( Thrips palmi Karny , Thrips tabaci Lindeman ), cabbage moth ( Plutella ) xylostella ), Tobacco cutworm ( Spodoptera litura ), Tropical cutworm ( Spodoptera ) frugiperda ), green onion moth ( Spodoptera exigua ), or soybean moth ( Maruca vitrta ).
일 실시예에서 상기 화합물은 꽃노랑총채벌레 및 콩명나방에 대해 우수한 살충 활성을 보이며, 시험 결과 상용 중인 대조군 화합물에 비해 현저히 우수한 살충 활성을 보였다.In one example, the compound showed excellent insecticidal activity against flower thrips and soybean moth, and as a result of the test, it showed significantly better insecticidal activity compared to the commercially available control compound.
일 실시예에서 상기 살충제 조성물은 상기 해충에 대해 우수한 살충활성을 가질 뿐만 아니라, 빠른 시간(예를 들어 24시간) 내에 살충활성을 가짐으로써 보다 효과적으로 방제가 가능하도록 할 수 있으며, 또는 상기 해충에 대해서는 살충활성을 보이면서도, 익충인 꿀벌에 대해서는 안전하여 효과적으로 활용될 수 있다.In one embodiment, the pesticide composition not only has excellent insecticidal activity against the pests, but also has insecticidal activity within a short period of time (for example, 24 hours), thereby enabling more effective control, or Although it shows insecticidal activity, it is safe against honey bees, which are beneficial insects, so it can be used effectively.
또한, 일 실시예에서 상기 살충제 조성물은 살충제를 식물에 처리한 경우, 식물에 대한 섭식 면적을 효과적으로 감소시킬 수 있으며, 따라서 해충에 대해 살충활성을 보이는 동시에 해충이 식물을 섭식하는 현상도 감소시킬 수 있는 효과가 있다.In addition, in one embodiment, the pesticide composition can effectively reduce the feeding area for plants when the pesticide is treated with the plant, and thus exhibits insecticidal activity against pests while also reducing the phenomenon of pests eating plants. There is an effect.
다른 일 구현예는 상기 화합물, 이의 입체 이성질체, 이의 수화물, 및 이의상기 염으로부터 선택되는 1종 이상의 화합물을 농작물 또는 이의 서식지에 처리하는 단계를 포함하는 해충을 방제하는 방법을 제공한다.Another embodiment provides a method for controlling pests, comprising treating crops or their habitat with one or more compounds selected from the above compounds, stereoisomers thereof, hydrates thereof, and salts thereof.
상기 해충의 방제 방법은, 상기 화합물을 포함하는 조성물을 방제 대상에 분무하는 단계, 접촉시키는 단계, 또는 침지하는 단계를 포함할 수 있으며, 통상적으로 방제를 위해 처리하는 방법을 더 포함할 수도 있고, 반드시 특정 방법에 한정하고자 하는 것은 아니다.The method for controlling pests may include the step of spraying, contacting, or immersing a composition containing the above compound on a control target, and may further include a conventional treatment method for control, It is not necessarily intended to be limited to a specific method.
이하, 본 발명의 실시예 및 실험예를 하기에 구체적으로 예시하여 설명한다. 다만, 후술하는 실시예 및 실험예는 본 발명의 일부를 예시하는 것일 뿐, 본 발명이 이에 한정되는 것은 아니다.Hereinafter, examples and experimental examples of the present invention will be described in detail below. However, the examples and experimental examples described below only illustrate a part of the present invention, and the present invention is not limited thereto.
[반응식 1][Scheme 1]
<< 실시예Example 1> 1>
상기 반응식 1의 방법으로 실시예 1의 화합물을 제조하였으며, 구체적으로는 4-5-(3,5-다이클로로페닐)-5-(트리플루오로메틸)-4,5-다이하이드로아이소옥사졸-3-일)-2-메틸벤조산 (200 mg, 0.47 mmol)에 메틸렌클로라이드 (MC, 5 mL)를 희석하고 에틸렌 다이클로라이드 (EDC, 180 mg, 0.94 mmol)과 4-디메틸아미노피리딘(DMAP, 10 mg, 0.01 mmol)를 첨가한 후 2-클로로에틸아민 하이드로클로라이드 (110 mg, 0.94 mmol)을 넣었다. 실온에서 12시간 교반 후 반응 종결된 것을 TLC로 확인한 후 MC/NaHCO3로 추출하였다. 그 다음 유기층을 무수 Na2SO4로 건조 시키고 갑압하여 용매를 제거하였다. 반응 혼합물을 실리카겔 컬럼크로마토그래피로 정제하여 실시예 1의 화합물 (0.2 g)을 제조하였다.The compound of Example 1 was prepared by the method of Scheme 1, specifically, 4-5-(3,5-dichlorophenyl)-5-(trifluoromethyl)-4,5-dihydroisoxazole -3-yl)-2-methylbenzoic acid (200 mg, 0.47 mmol) was diluted with methylene chloride (MC, 5 mL) and ethylene dichloride (EDC, 180 mg, 0.94 mmol) and 4-dimethylaminopyridine (DMAP, 10 mg, 0.01 mmol) was added, followed by 2-chloroethylamine hydrochloride (110 mg, 0.94 mmol). After stirring at room temperature for 12 hours, completion of the reaction was confirmed by TLC and extracted with MC/NaHCO 3 . Next, the organic layer was dried over anhydrous Na 2 SO 4 and the solvent was removed by reducing pressure. The reaction mixture was purified by silica gel column chromatography to prepare the compound of Example 1 (0.2 g).
<< 실시예Example 2> 2>
4-(5-(3,5-다이클로로페닐)-5-(트리플루오로메틸)-4,5-다이하이드로아이소옥사졸-3-일)-N-((1-하이드록시사이클로프로필)메틸)-1-나프트아마이드 35 mg, 사이클로프로판설포닐 클로라이드 70.7 mg을 DMF 1 mL에 녹여 상온에서 하룻밤 동안으로 반응시킨 다음, 0 ℃에서 H2O를 넣어 퀀칭한 후 깔대기(saperate funnel)에 붓고 NaHCO3와 에틸아세테이트(EA)를 넣어 섞어 준 후 EA층만 분리하였다. 그 다음 분리한 EA층을 식염수로 씻어준 후 다시 EA층만 분리한 후, MgSO4로 건조한 후 여과하고, 컬럼 크로마토그래피로 실시예 2의 화합물 (14 mg)을 제조하였다.4-(5-(3,5-dichlorophenyl)-5-(trifluoromethyl)-4,5-dihydroisoxazol-3-yl)-N-((1-hydroxycyclopropyl) 35 mg of methyl)-1-naphtamide and 70.7 mg of cyclopropanesulfonyl chloride were dissolved in 1 mL of DMF and reacted at room temperature overnight, then quenched by adding H 2 O at 0°C and placed in a saperate funnel. After pouring and mixing NaHCO 3 and ethyl acetate (EA), only the EA layer was separated. Next, the separated EA layer was washed with saline solution, and only the EA layer was separated again, dried over MgSO 4 and filtered, and the compound of Example 2 (14 mg) was prepared by column chromatography.
<< 실시예Example 3> 3>
상기 실시예 2에서 출발물질로 4-(5-(3,5-다이클로로페닐)-5-(트리플루오로메틸)-4,5-(다이하이드로아이소옥사졸-3-일)-N-(2-하이드록시프로필)-2-메틸벤즈아마이드 50 mg 및 메탄설포닐 클로라이드 0.06 mL를 사용하여 실시예 3 화합물을 제조하였다.In Example 2, the starting material was 4-(5-(3,5-dichlorophenyl)-5-(trifluoromethyl)-4,5-(dihydroisoxazol-3-yl)-N- The compound of Example 3 was prepared using 50 mg of (2-hydroxypropyl)-2-methylbenzamide and 0.06 mL of methanesulfonyl chloride.
<< 실시예Example 4> 4>
상기 실시예 2에서 출발물질로 4-(5-(3,5-다이클로로페닐)-5-(트리플루오로메틸)-4,5-다이하이드로아이소옥사졸-3-일)-N-(1,3-다이하이드로프로판-2-일)-2-메틸벤즈아마이드 50 mg 및 메탄설포닐 클로라이드 0.06 mL를 사용하여 실시예 4 화합물을 제조하였다.In Example 2, the starting material was 4-(5-(3,5-dichlorophenyl)-5-(trifluoromethyl)-4,5-dihydroisoxazol-3-yl)-N-( The compound of Example 4 was prepared using 50 mg of 1,3-dihydropropan-2-yl)-2-methylbenzamide and 0.06 mL of methanesulfonyl chloride.
<< 실시예Example 5> 5>
상기 실시예 2에서 출발물질로 4-(5-3,5-다이클로로페닐)-5-(트리플루오로메틸)-4,5-다이하이드로아이소옥사졸-3-일)-N-(1-(하이드록시메틸)사이클로프로필)-2-메틸벤즈아마이드 50 mg 및 메탄설포닐 클로라이드 0.06 mL를 사용하여 실시예 5 화합물을 제조하였다.In Example 2, the starting material was 4-(5-3,5-dichlorophenyl)-5-(trifluoromethyl)-4,5-dihydroisoxazol-3-yl)-N-(1 The compound of Example 5 was prepared using 50 mg of -(hydroxymethyl)cyclopropyl)-2-methylbenzamide and 0.06 mL of methanesulfonyl chloride.
<< 실시예Example 6> 6>
4,5-(3,5-다이클로로페닐)-5-(트리플루오로메틸)-4,5-다이하이드로아이소옥사졸-3-일)-2-메틸벤조산 (0.5 g, 1.19 mmol)에 3-아미노-1,1,1-트리플루오로프로판-2-올 (0.17 g, 1.31 mmol), HATU (0.54 g, 1.42 mmol)에 DMF (2 mL)희석한 후 0 ℃에서 TEA (0.36 mL) 첨가한 후 0 ℃에서 2시간 교반 후 반응 종결된 것을 TLC로 확인한 후 EA/NaHCO3로 추출하였다. 유기층을 무수 Na2SO4로 건조 시키고 갑압하여 용매를 제거하였다. 반응 혼합물을 실리카겔 컬럼크로마토그래피로 정제하여 화합물(0.4 g)을 수득하였다. 수득한 화합물 (0.1 g, 0.2 mmol)을 DMF (2 mL)에 녹인 후 사이클로프로판설포닐 클로라이드 (0.14 mL, 1.4 mmol) 첨가 후 80 ℃ 에서 12시간 교반 후 반응 종결된 것을 TLC로 확인한 후 EA/H2O로 추출하였다. 유기층을 무수Na2SO4로 건조 시키고 갑압하여 용매를 제거하였다. 반응 혼합물을 실리카겔 컬럼크로마토그래피로 정제하여 실시예 6 화합물(0.09 g)을 제조하였다.4,5-(3,5-dichlorophenyl)-5-(trifluoromethyl)-4,5-dihydroisoxazol-3-yl)-2-methylbenzoic acid (0.5 g, 1.19 mmol) 3-Amino-1,1,1-trifluoropropan-2-ol (0.17 g, 1.31 mmol) was diluted in HATU (0.54 g, 1.42 mmol) in DMF (2 mL) and then diluted in TEA (0.36 mL) at 0°C. ) After addition, the reaction was stirred at 0°C for 2 hours, and the completion of the reaction was confirmed by TLC and extracted with EA/NaHCO 3 . The organic layer was dried over anhydrous Na 2 SO 4 and the solvent was removed by reducing pressure. The reaction mixture was purified by silica gel column chromatography to obtain the compound (0.4 g). The obtained compound (0.1 g, 0.2 mmol) was dissolved in DMF (2 mL), cyclopropanesulfonyl chloride (0.14 mL, 1.4 mmol) was added, stirred at 80°C for 12 hours, and the reaction was confirmed complete by TLC, and then EA/ Extracted with H 2 O. The organic layer was dried over anhydrous Na 2 SO 4 and the solvent was removed by reducing pressure. The reaction mixture was purified by silica gel column chromatography to prepare the compound of Example 6 (0.09 g).
<< 실시예Example 7> 7>
상기 실시예 6에서 3-아미노-1,1,1-트리플루오로프로판-2-올 대신 2-아미노-3,3,3-트리플루오로프로판-1-올을 사용하여 실시예 7 화합물을 제조하였다.The compound of Example 7 was prepared by using 2-amino-3,3,3-trifluoropropan-1-ol instead of 3-amino-1,1,1-trifluoropropan-2-ol in Example 6. Manufactured.
<< 실시예Example 8> 8>
상기 실시예 6에서 3-아미노-1,1,1-트리플루오로프로판-2-올 대신 (1-아미노사이클로뷰틸)메탄올을 사용하여 실시예 8 화합물을 제조하였다.The compound of Example 8 was prepared by using (1-aminocyclobutyl)methanol instead of 3-amino-1,1,1-trifluoropropan-2-ol in Example 6.
<< 실시예Example 9 내지 9 to 실시예Example 18> 18>
상기 반응식 1의 방법으로 실시예 9 내지 실시예 18의 화합물을 제조하였으며, 상기 반응식 1에서 실시예 9 내지 실시예 18을 제조하기 위한 R1, R2, x, R3를 갖는 화합물 또는 공지된 화합물을 이용하고 실시예 1의 제조방법을 참고하여 제조하였다.Compounds of Examples 9 to 18 were prepared by the method of Scheme 1, and compounds having R 1 , R 2 , x, R 3 or known compounds for preparing Examples 9 to 18 in Scheme 1 were prepared. It was prepared using the compound and referring to the preparation method of Example 1.
<< 실시예Example 19> 19>
상기 실시예 6에서 3-아미노-1,1,1-트리플루오로프로판-2-올 대신 (1-(아미노메틸)사이클로프로필)메탄올을 사용하여 실시예 19 화합물을 제조하였다.Compound Example 19 was prepared by using (1-(aminomethyl)cyclopropyl)methanol instead of 3-amino-1,1,1-trifluoropropan-2-ol in Example 6.
<< 실시예Example 20> 20>
상기 실시예 6에서 3-아미노-1,1,1-트리플루오로프로판-2-올 대신 (1-(아미노메틸)사이클로뷰틸)메탄올을 사용하여 실시예 20 화합물을 제조하였다.Compound Example 20 was prepared by using (1-(aminomethyl)cyclobutyl)methanol instead of 3-amino-1,1,1-trifluoropropan-2-ol in Example 6.
<< 실시예Example 21> 21>
4-(5-(3,5-다이클로로페닐)-5-(트리플루오로메틸)-4,5-다이하이드로아이소옥사졸-3-일)-2-메틸벤조산 125.4 mg, 트리메틸아민 0.13 mL, HATU 137 mg 을 0 ℃에서 DMF 0.7 mL에 녹인 후, 3-클로로프로판-1-아민 30.9 mg을 0 ℃에서 DMF 0.3 mL에 녹인 후 위 혼합물에에 천천히 첨가한 후 0 ℃에서 1시간 동안 반응하였다. 그다음 0 ℃에서 H2O를 넣어 퀀칭한 후 깔때기에 붓고 NaHCO3와 EA를 넣어 섞어 준 후 EA층만 분리한 다음, 분리한 EA층을 식염수로 씻어준 후 다시 EA층만 분리하였다. 그 다음 MgSO4로 건조한 후 여과하고 컬럼 크로마토그래피로 정제하여 실시예 21 화합물 (56.7 mg)을 제조하였다.4-(5-(3,5-dichlorophenyl)-5-(trifluoromethyl)-4,5-dihydroisoxazol-3-yl)-2-methylbenzoic acid 125.4 mg, trimethylamine 0.13 mL , 137 mg of HATU was dissolved in 0.7 mL of DMF at 0 ℃, and then 30.9 mg of 3-chloropropan-1-amine was dissolved in 0.3 mL of DMF at 0 ℃, then slowly added to the above mixture and reacted at 0 ℃ for 1 hour. did. Then, after quenching by adding H 2 O at 0°C, it was poured into a funnel, NaHCO 3 and EA were added and mixed, and only the EA layer was separated. The separated EA layer was washed with saline solution, and then only the EA layer was separated again. Then, it was dried with MgSO 4 , filtered, and purified by column chromatography to prepare the compound of Example 21 (56.7 mg).
<< 실시예Example 22> 22>
상기 실시예 21에서 3-클로로프로판-1-아민 대신 4-클로로뷰탄-1-아민을 사용하여 실시예 22 화합물을 제조하였다.The compound of Example 22 was prepared by using 4-chlorobutan-1-amine instead of 3-chloropropan-1-amine in Example 21.
<< 실시예Example 23> 23>
상기 반응식 1의 방법으로 실시예 23의 화합물을 제조하였으며, 상기 반응식 1에서 실시예 23을 제조하기 위한 R1, R2, x, R3를 갖는 화합물 또는 공지된 화합물을 이용하고 공지된 제조방법을 참고하여 제조하였다.The compound of Example 23 was prepared by the method of Scheme 1, and a compound having R 1 , R 2 , x, R 3 or a known compound was used to prepare Example 23 in Scheme 1, and a known preparation method was used. It was manufactured with reference to.
<< 실시예Example 24> 24>
4-(5-(3,5-다이클로로페닐)-5-(트리플루오로메틸)-4,5-다이하이드로아이소옥사졸-3-일)-N-(2-하이드록시프로필)-1-나프트아마이드 50 mg, 사이클로프로판설포닐 클로라이드 0.07 mL을 DMF 1 mL에 녹여 상온에서 하룻밤동안 반응한 후, 0 ℃에서 H2O를 넣어 퀀칭한 후 깔대기에 붓고 NaHCO3와 EA를 넣어 섞어 준 후 EA층만 분리한 다음, 분리한 EA층을 식염수로 씻어준 후 다시 EA층만 분리한 후, MgSO4로 건조한 후 여과하고 컬럼 크로마토그래피로 정제하여 실시예 24 화합물 (8 mg)을 제조하였다.4-(5-(3,5-dichlorophenyl)-5-(trifluoromethyl)-4,5-dihydroisoxazol-3-yl)-N-(2-hydroxypropyl)-1 -Dissolve 50 mg of naphthamide and 0.07 mL of cyclopropanesulfonyl chloride in 1 mL of DMF and react at room temperature overnight. After quenching by adding H 2 O at 0 ℃, pour into a funnel and mix with NaHCO 3 and EA. After separating only the EA layer, the separated EA layer was washed with saline solution, and then only the EA layer was separated again, dried over MgSO 4 , filtered, and purified by column chromatography to prepare the compound of Example 24 (8 mg).
<< 실시예Example 25> 25>
상기 실시예 24에서 출발물질로 4-(5-(3,5-다이클로로페닐)-5-(트리플루오로메틸)-4,5-다이하이드로아이소옥사졸-3-일)-N-(1,3-다이하이드록시프로판-2-일)-1-나프트아마이드를 사용하여 실시예 25의 화합물을 제조하였다.In Example 24, the starting material was 4-(5-(3,5-dichlorophenyl)-5-(trifluoromethyl)-4,5-dihydroisoxazol-3-yl)-N-( The compound of Example 25 was prepared using 1,3-dihydroxypropan-2-yl)-1-naphtamide.
<< 실시예Example 26> 26>
상기 실시예 24에서 출발물질로 4-(5-(3,5-다이클로로페닐)-5-(트리플루오로메틸)-4,5-다이하이드로아이소옥사졸-3-일)-N-(1-(하이드록시메틸)사이클로프로필-1-나프트아마이드를 사용하여 실시예 26의 화합물을 제조하였다.In Example 24, the starting material was 4-(5-(3,5-dichlorophenyl)-5-(trifluoromethyl)-4,5-dihydroisoxazol-3-yl)-N-( The compound of Example 26 was prepared using 1-(hydroxymethyl)cyclopropyl-1-naphtamide.
<< 실시예Example 27> 27>
상기 실시예 6에서 3-아미노-1,1,1-트리플루오로프로판-2-올 대신 2-아미노3,3,3-트리플루오로프로판-1-올을 사용하고 출발물질을 실시예 27을 제조하기 위한 화합물을 사용하여 실시예 27 화합물을 제조하였다.In Example 6, 2-amino3,3,3-trifluoropropan-1-ol was used instead of 3-amino-1,1,1-trifluoropropan-2-ol, and the starting material was prepared in Example 27. The compound of Example 27 was prepared using the compound for preparing.
<< 실시예Example 28> 28>
상기 실시예 27에서 2-아미노3,3,3-트리플루오로프로판-1-올 대신 (3-아미노옥세탄-3-일)메탄올을 사용하여 실시예 28 화합물을 제조하였다.The compound of Example 28 was prepared by using (3-aminooxetan-3-yl)methanol instead of 2-amino3,3,3-trifluoropropan-1-ol in Example 27.
<< 실시예Example 29 내지 29 to 29 실시예Example 41> 41>
상기 반응식 1의 방법으로 실시예 29 내지 실시예 41의 화합물을 제조하였으며, 상기 반응식 1에서 실시예 29 내지 실시예 41을 제조하기 위한 R1, R2, x, R3를 갖는 화합물 또는 공지된 화합물을 이용하고 실시예 1의 제조방법을 참고하여 제조하였다.Compounds of Examples 29 to 41 were prepared by the method of Scheme 1, and compounds having R 1 , R 2 , x, R 3 or known compounds for preparing Examples 29 to 41 in Scheme 1 It was prepared using the compound and referring to the preparation method of Example 1.
<< 실시예Example 42> 42>
상기 실시예 21에서 출발물질로 4-(5-(3,5-다이클로로페닐)-5-(트리플루오로메틸)-4,5-다이하이드로아이소옥사졸-3-일)-1-나프토익산 136 mg, 3-클로로프로판-1-아민 30.9 mg을 사용하여 실시예 42 화합물을 제조하였다.In Example 21, 4-(5-(3,5-dichlorophenyl)-5-(trifluoromethyl)-4,5-dihydroisoxazol-3-yl)-1-naph was used as the starting material. The compound of Example 42 was prepared using 136 mg of TOEIC acid and 30.9 mg of 3-chloropropan-1-amine.
<< 실시예Example 43> 43>
상기 실시예 21에서 출발물질로 4-(5-(3,5-다이클로로페닐)-5-(트리플루오로메틸)-4,5-다이하이드로아이소옥사졸-3-일)-1-나프토익산 226.6 mg, 4-클로로뷰탄-1-아민 79.2 mg을 사용하여 실시예 43 화합물을 제조하였다.In Example 21, 4-(5-(3,5-dichlorophenyl)-5-(trifluoromethyl)-4,5-dihydroisoxazol-3-yl)-1-naph was used as the starting material. The compound of Example 43 was prepared using 226.6 mg of TOEIC acid and 79.2 mg of 4-chlorobutan-1-amine.
하기 표 1에 실시예 1 내지 실시예 43에서 제조한 화합물의 화학식을 나타내었으며, 각 화합물의 IUPAC name 및 NMR 데이터를 표의 하단에 정리하였다 (표 1에서 No.는 실시예 번호이다).Table 1 below shows the chemical formulas of the compounds prepared in Examples 1 to 43, and the IUPAC name and NMR data of each compound are summarized at the bottom of the table (No. in Table 1 is the example number).
<화합물 이름 및 NMR 데이터><Compound name and NMR data>
실시예 1: N-(2-클로로에틸)-4-(5-(3,5-다이클로로페닐)-5-(트리플루오로메틸)-4,5-다이하이드로아이소옥사졸-3-일)-2-메틸벤즈아마이드(N-(2-chloroethyl)-4-(5-(3,5-dichlorophenyl)-5-(trifluoromethyl)-4,5-dihydroisoxazol-3-yl)-2-methylbenzamide)Example 1: N-(2-chloroethyl)-4-(5-(3,5-dichlorophenyl)-5-(trifluoromethyl)-4,5-dihydroisoxazol-3-yl )-2-methylbenzamide (N-(2-chloroethyl)-4-(5-(3,5-dichlorophenyl)-5-(trifluoromethyl)-4,5-dihydroisoxazol-3-yl)-2-methylbenzamide)
1H NMR (400 MHz, CDCl3) δ 7.54-7.50 (m, 4H), 7.47-7.42 (m, 2H), 6.17 (s, 1H), 4.08 (d, J = 17.2Hz, 1H), 3.83-3.74 (m, 4H), 3.70 (d, J = 17.2Hz, 1H), 2.49 (s, 3H)1H NMR (400 MHz, CDCl3) δ 7.54-7.50 (m, 4H), 7.47-7.42 (m, 2H), 6.17 (s, 1H), 4.08 (d, J = 17.2Hz, 1H), 3.83-3.74 ( m, 4H), 3.70 (d, J = 17.2Hz, 1H), 2.49 (s, 3H)
실시예 2: N-(1-클로로프로판-2-일)-4-(5-(3,5-다이클로로페닐)-5-(트리플루오로메틸)-4,5-다이하이드로아이소옥사졸-3-일)-2-메틸벤즈아마이드(N-(1-chloropropan-2-yl)-4-(5-(3,5-dichlorophenyl)-5-(trifluoromethyl)-4,5-dihydroisoxazol-3-yl)-2-methylbenzamide)Example 2: N-(1-chloropropan-2-yl)-4-(5-(3,5-dichlorophenyl)-5-(trifluoromethyl)-4,5-dihydroisoxazole -3-yl)-2-methylbenzamide (N-(1-chloropropan-2-yl)-4-(5-(3,5-dichlorophenyl)-5-(trifluoromethyl)-4,5-dihydroisoxazol-3 -yl)-2-methylbenzamide)
1H NMR (500 MHz, CDCl3) δ 7.52-7.45 (m, 4H), 7.44-7.37 (m, 2H), 6.01 (s, 1H), 4.52 (s, 1H), 4.08 (d, J = 17.7Hz, 1H), 3.85 (dd, J = 4Hz, J = 11.2Hz, 1H), 3.70 (d, J = 17.2Hz, 1H), 3.63 (dd, J =3.7Hz, J = 11.2Hz, 1H), 2.44 (s, 3H), 1.35 (d, J = 5.4Hz, 3H)1H NMR (500 MHz, CDCl3) δ 7.52-7.45 (m, 4H), 7.44-7.37 (m, 2H), 6.01 (s, 1H), 4.52 (s, 1H), 4.08 (d, J = 17.7Hz, 1H), 3.85 (dd, J = 4Hz, J = 11.2Hz, 1H), 3.70 (d, J = 17.2Hz, 1H), 3.63 (dd, J =3.7Hz, J = 11.2Hz, 1H), 2.44 ( s, 3H), 1.35 (d, J = 5.4Hz, 3H)
실시예 3: N-(2-클로로프로필)-4-(5-(3,5-다이클로로페닐)-5-(트리플루오로메틸)-4,5-다이하이드로아이소옥사졸-3-일)-2-메틸벤즈아마이드(N-(2-chloropropyl)-4-(5-(3,5-dichlorophenyl)-5-(trifluoromethyl)-4,5-dihydroisoxazol-3-yl)-2-methylbenzamide)Example 3: N-(2-chloropropyl)-4-(5-(3,5-dichlorophenyl)-5-(trifluoromethyl)-4,5-dihydroisoxazol-3-yl )-2-methylbenzamide (N-(2-chloropropyl)-4-(5-(3,5-dichlorophenyl)-5-(trifluoromethyl)-4,5-dihydroisoxazol-3-yl)-2-methylbenzamide)
1H NMR (500 MHz, CDCl3) δ 7.49 (dd, J = 4.0, 2.4 Hz, 4H), 7.44 - 7.40 (m, 2H), 5.95 (s, 1H), 4.09 - 4.02 (m, 3H), 3.67 (d, J = 17.2 Hz, 1H), 2.47 (s, 3H), 2.38 - 2.26 (m, 4H), 2.04 (dtt, J = 11.9, 9.6, 4.7 Hz, 1H), 1.90 (dp, J = 11.7, 8.6 Hz, 1H)1H NMR (500 MHz, CDCl3) δ 7.49 (dd, J = 4.0, 2.4 Hz, 4H), 7.44 - 7.40 (m, 2H), 5.95 (s, 1H), 4.09 - 4.02 (m, 3H), 3.67 ( d, J = 17.2 Hz, 1H), 2.47 (s, 3H), 2.38 - 2.26 (m, 4H), 2.04 (dtt, J = 11.9, 9.6, 4.7 Hz, 1H), 1.90 (dp, J = 11.7, 8.6 Hz, 1H)
실시예 4: 4-(5-(3,5-다이클로로페닐)-5-(트리플루오로메틸)-4,5-다이하이드로아이소옥사졸-3-일)-N-(1,3-다이클로로프로판-2-일)-2-메틸벤즈아마이드(4-(5-(3,5-dichlorophenyl)-5-(trifluoromethyl)-4,5-dihydroisoxazol-3-yl)-N-(1,3-dichloropropan-2-yl)-2-methylbenzamide)Example 4: 4-(5-(3,5-dichlorophenyl)-5-(trifluoromethyl)-4,5-dihydroisoxazol-3-yl)-N-(1,3- Dichloropropan-2-yl)-2-methylbenzamide (4-(5-(3,5-dichlorophenyl)-5-(trifluoromethyl)-4,5-dihydroisoxazol-3-yl)-N-(1, 3-dichloropropan-2-yl)-2-methylbenzamide)
1H NMR (400 MHz, CDCl3) δ 7.51-7.45 (m, 4H), 7.43-7.37 (m, 2H), 6.32 (d, J = 8.4Hz, 1H), 4.67-4.58 (m, 1H), 4.13-4.04 (m, 1H), 3.88 (dd, J = 4.6Hz, J =11.3Hz, 2H), 3.76 (dd, J = 5.9Hz, J =11.3Hz, 2H), 3.71 (d, J = 17.3Hz, 1H), 2.44 (s, 3H)1H NMR (400 MHz, CDCl3) δ 7.51-7.45 (m, 4H), 7.43-7.37 (m, 2H), 6.32 (d, J = 8.4Hz, 1H), 4.67-4.58 (m, 1H), 4.13- 4.04 (m, 1H), 3.88 (dd, J = 4.6Hz, J =11.3Hz, 2H), 3.76 (dd, J = 5.9Hz, J =11.3Hz, 2H), 3.71 (d, J = 17.3Hz, 1H), 2.44 (s, 3H)
실시예 5: N-(1-(클로로메틸)사이클로프로필)-4-(5-(3,5-다이클로로페닐)-5-(트리플루오로메틸)-4,5-다이하이드로아이소옥사졸-3-일)-2-메틸벤즈아마이드(N-(1-(chloromethyl)cyclopropyl)-4-(5-(3,5-dichlorophenyl)-5-(trifluoromethyl)-4,5-dihydroisoxazol-3-yl)-2-methylbenzamide)Example 5: N-(1-(chloromethyl)cyclopropyl)-4-(5-(3,5-dichlorophenyl)-5-(trifluoromethyl)-4,5-dihydroisoxazole -3-yl)-2-methylbenzamide (N-(1-(chloromethyl)cyclopropyl)-4-(5-(3,5-dichlorophenyl)-5-(trifluoromethyl)-4,5-dihydroisoxazol-3- yl)-2-methylbenzamide)
1H NMR (400 MHz, CDCl3) δ 7.54-7.38 (m, 6H), 6.32 (s, 1H), 4.07 (d, J = 17.2Hz, 1H), 3.82 (s, 2H), 3.69 (d, J = 17.2Hz, 1H), 2.47 (s, 3H), 1.31-1.00 (m, 4H)1H NMR (400 MHz, CDCl3) δ 7.54-7.38 (m, 6H), 6.32 (s, 1H), 4.07 (d, J = 17.2Hz, 1H), 3.82 (s, 2H), 3.69 (d, J = 17.2Hz, 1H), 2.47 (s, 3H), 1.31-1.00 (m, 4H)
실시예 6: N-(2-클로로-3,3,3-트리플루오로프로필)-4-(5-(3,5-다이클로로페닐)-5-(트리플루오로메틸)-4,5-다이하이드로아이소옥사졸-3-일)-2-메틸벤즈아마이드(N-(2-chloro-3,3,3-trifluoropropyl)-4-(5-(3,5-dichlorophenyl)-5-(trifluoromethyl)-4,5-dihydroisoxazol-3-yl)-2-methylbenzamide)Example 6: N-(2-chloro-3,3,3-trifluoropropyl)-4-(5-(3,5-dichlorophenyl)-5-(trifluoromethyl)-4,5 -Dihydroisoxazol-3-yl)-2-methylbenzamide (N-(2-chloro-3,3,3-trifluoropropyl)-4-(5-(3,5-dichlorophenyl)-5-( trifluoromethyl)-4,5-dihydroisoxazol-3-yl)-2-methylbenzamide)
1H NMR (500 MHz, CDCl3) δ 7.87 (d, J = 8.2 Hz, 1H), 7.55 - 7.47 (m, 4H), 7.41 (t, J = 1.9 Hz, 1H), 4.88 (dp, J = 10.1, 6.6 Hz, 1H), 4.35 - 4.21 (m, 2H), 4.07 (dd, J = 17.1, 0.8 Hz, 1H), 3.69 (d, J = 17.1 Hz, 1H), 2.60 (s, 3H)1H NMR (500 MHz, CDCl3) δ 7.87 (d, J = 8.2 Hz, 1H), 7.55 - 7.47 (m, 4H), 7.41 (t, J = 1.9 Hz, 1H), 4.88 (dp, J = 10.1, 6.6 Hz, 1H), 4.35 - 4.21 (m, 2H), 4.07 (dd, J = 17.1, 0.8 Hz, 1H), 3.69 (d, J = 17.1 Hz, 1H), 2.60 (s, 3H)
실시예 7: N-(3-클로로-1,1,1-트리플루오로프로판-2-일)-4-(5-(3,5-다이클로로페닐)-5-(트리플루오로메틸)-4,5-다이하이드로아이소옥사졸-3-일)-2-메틸벤즈아마이드(N-(3-chloro-1,1,1-trifluoropropan-2-yl)-4-(5-(3,5-dichlorophenyl)-5-(trifluoromethyl)-4,5-dihydroisoxazol-3-yl)-2-methylbenzamide)Example 7: N-(3-chloro-1,1,1-trifluoropropan-2-yl)-4-(5-(3,5-dichlorophenyl)-5-(trifluoromethyl) -4,5-dihydroisoxazol-3-yl)-2-methylbenzamide (N-(3-chloro-1,1,1-trifluoropropan-2-yl)-4-(5-(3, 5-dichlorophenyl)-5-(trifluoromethyl)-4,5-dihydroisoxazol-3-yl)-2-methylbenzamide)
1H NMR (500 MHz, CDCl3) δ 7.53 (dd, J = 5.5, 1.9 Hz, 2H), 7.49 (d, J = 1.8 Hz, 2H), 7.45 (d, J = 8.4 Hz, 1H), 7.42 (t, J = 1.8 Hz, 1H), 6.18 (d, J = 9.8 Hz, 1H), 5.21 - 5.12 (m, 1H), 4.06 (d, J = 17.3 Hz, 1H), 3.93 - 3.79 (m, 2H), 3.68 (d, J = 17.3 Hz, 1H), 2.46 (s, 3H)1H NMR (500 MHz, CDCl3) δ 7.53 (dd, J = 5.5, 1.9 Hz, 2H), 7.49 (d, J = 1.8 Hz, 2H), 7.45 (d, J = 8.4 Hz, 1H), 7.42 (t , J = 1.8 Hz, 1H), 6.18 (d, J = 9.8 Hz, 1H), 5.21 - 5.12 (m, 1H), 4.06 (d, J = 17.3 Hz, 1H), 3.93 - 3.79 (m, 2H) , 3.68 (d, J = 17.3 Hz, 1H), 2.46 (s, 3H)
실시예 8: N-(1-(클로로메틸)사이클로뷰틸)-4-(5-(3,5-다이클로로페닐)-5-(트리플루오로메틸)-4,5-다이하이드로아이소옥사졸-3-일)-2-메틸벤즈아마이드(N-(1-(chloromethyl)cyclobutyl)-4-(5-(3,5-dichlorophenyl)-5-(trifluoromethyl)-4,5-dihydroisoxazol-3-yl)-2-methylbenzamide)Example 8: N-(1-(chloromethyl)cyclobutyl)-4-(5-(3,5-dichlorophenyl)-5-(trifluoromethyl)-4,5-dihydroisoxazole -3-yl)-2-methylbenzamide (N-(1-(chloromethyl)cyclobutyl)-4-(5-(3,5-dichlorophenyl)-5-(trifluoromethyl)-4,5-dihydroisoxazol-3- yl)-2-methylbenzamide)
1H NMR (500 MHz, CDCl3) δ 7.49 (dd, J = 4.0, 2.4 Hz, 4H), 7.44 - 7.40 (m, 2H), 5.95 (s, 1H), 4.09 - 4.02 (m, 3H), 3.67 (d, J = 17.2 Hz, 1H), 2.47 (s, 3H), 2.38 - 2.26 (m, 4H), 2.04 (dtt, J = 11.9, 9.6, 4.7 Hz, 1H), 1.90 (dp, J = 11.7, 8.6 Hz, 1H)1H NMR (500 MHz, CDCl3) δ 7.49 (dd, J = 4.0, 2.4 Hz, 4H), 7.44 - 7.40 (m, 2H), 5.95 (s, 1H), 4.09 - 4.02 (m, 3H), 3.67 ( d, J = 17.2 Hz, 1H), 2.47 (s, 3H), 2.38 - 2.26 (m, 4H), 2.04 (dtt, J = 11.9, 9.6, 4.7 Hz, 1H), 1.90 (dp, J = 11.7, 8.6 Hz, 1H)
실시예 9: N-(2-클로로에틸)-4-(5-(3,5-다이클로로-4-플루오로페닐)-5-(트리플루오로메틸)-4,5-다이하이드로아이소옥사졸-3-일)-2-메틸벤즈아마이드(N-(2-chloroethyl)-4-(5-(3,5-dichloro-4-fluorophenyl)-5-(trifluoromethyl)-4,5-dihydroisoxazol-3-yl)-2-methylbenzamide)Example 9: N-(2-chloroethyl)-4-(5-(3,5-dichloro-4-fluorophenyl)-5-(trifluoromethyl)-4,5-dihydroisox sazol-3-yl)-2-methylbenzamide (N-(2-chloroethyl)-4-(5-(3,5-dichloro-4-fluorophenyl)-5-(trifluoromethyl)-4,5-dihydroisoxazol- 3-yl)-2-methylbenzamide)
1H NMR (500 MHz, DMSO-d6) δ 8.61 (t, J = 5.6 Hz, 1H), 7.81 (d, J = 6.3 Hz, 2H), 7.60 (dd, J = 8.2, 1.4 Hz, 2H), 7.46 - 7.41 (m, 1H), 4.42 - 4.25 (m, 2H), 3.74 (t, J = 6.1 Hz, 2H), 3.56 (q, J = 6.0 Hz, 2H), 2.38 (s, 3H)1H NMR (500 MHz, DMSO-d6) δ 8.61 (t, J = 5.6 Hz, 1H), 7.81 (d, J = 6.3 Hz, 2H), 7.60 (dd, J = 8.2, 1.4 Hz, 2H), 7.46 - 7.41 (m, 1H), 4.42 - 4.25 (m, 2H), 3.74 (t, J = 6.1 Hz, 2H), 3.56 (q, J = 6.0 Hz, 2H), 2.38 (s, 3H)
실시예 10: 4-(5-(3-클로로-5-(트리플루오로메틸)페닐)-5-(트리플루오로메틸)-4,5-다이하이드로아이소옥사졸-3-일)-N-(2-클로로에틸)-2-메틸벤즈아마이드(4-(5-(3-chloro-5-(trifluoromethyl)phenyl)-5-(trifluoromethyl)-4,5-dihydroisoxazol-3-yl)-N-(2-chloroethyl)-2-methylbenzamide)Example 10: 4-(5-(3-chloro-5-(trifluoromethyl)phenyl)-5-(trifluoromethyl)-4,5-dihydroisoxazol-3-yl)-N -(2-Chloroethyl)-2-methylbenzamide (4-(5-(3-chloro-5-(trifluoromethyl)phenyl)-5-(trifluoromethyl)-4,5-dihydroisoxazol-3-yl)-N -(2-chloroethyl)-2-methylbenzamide)
1H NMR (500 MHz, DMSO-d6) δ 8.61 (t, J = 5.7 Hz, 1H), 8.09 (d, J = 1.9 Hz, 1H), 7.98 (t, J = 1.8 Hz, 1H), 7.86 (s, 1H), 7.62 (dd, J = 8.1, 1.3 Hz, 2H), 7.47 - 7.41 (m, 1H), 4.49 - 4.32 (m, 2H), 3.75 (t, J = 6.1 Hz, 2H), 3.57 (q, J = 6.0 Hz, 2H), 2.39 (s, 3H)1H NMR (500 MHz, DMSO-d6) δ 8.61 (t, J = 5.7 Hz, 1H), 8.09 (d, J = 1.9 Hz, 1H), 7.98 (t, J = 1.8 Hz, 1H), 7.86 (s) , 1H), 7.62 (dd, J = 8.1, 1.3 Hz, 2H), 7.47 - 7.41 (m, 1H), 4.49 - 4.32 (m, 2H), 3.75 (t, J = 6.1 Hz, 2H), 3.57 ( q, J = 6.0 Hz, 2H), 2.39 (s, 3H)
실시예 11: N-(2-브로모에틸)-4-(5-(3,5-다이클로로페닐)-5-(트리플루오로메틸)-4,5-다이하이드로아이소옥사졸-3-일)-2-메틸벤즈아마이드(N-(2-bromoethyl)-4-(5-(3,5-dichlorophenyl)-5-(trifluoromethyl)-4,5-dihydroisoxazol-3-yl)-2-methylbenzamide)Example 11: N-(2-bromoethyl)-4-(5-(3,5-dichlorophenyl)-5-(trifluoromethyl)-4,5-dihydroisoxazole-3- 1)-2-methylbenzamide (N-(2-bromoethyl)-4-(5-(3,5-dichlorophenyl)-5-(trifluoromethyl)-4,5-dihydroisoxazol-3-yl)-2-methylbenzamide )
1H NMR (500 MHz, DMSO-d6) δ 7.84 (d, J = 8.1 Hz, 1H), 7.81 (q, J = 1.8 Hz, 1H), 7.68 - 7.61 (m, 5H), 4.36 (d, J = 9.6 Hz, 2H), 4.02 (t, J = 9.5 Hz, 2H), 3.74 (t, J = 6.2 Hz, 1H), 3.56 (q, J = 6.0 Hz, 1H), 2.58 (s, 3H)1H NMR (500 MHz, DMSO-d6) δ 7.84 (d, J = 8.1 Hz, 1H), 7.81 (q, J = 1.8 Hz, 1H), 7.68 - 7.61 (m, 5H), 4.36 (d, J = 9.6 Hz, 2H), 4.02 (t, J = 9.5 Hz, 2H), 3.74 (t, J = 6.2 Hz, 1H), 3.56 (q, J = 6.0 Hz, 1H), 2.58 (s, 3H)
실시예 12: 4-(5-(3,5-다이클로로페닐)-5-(트리플루오로메틸)-4,5-다이하이드로아이소옥사졸-3-일)-N-(2-플루오로에틸)-2-메틸벤즈아마이드(4-(5-(3,5-dichlorophenyl)-5-(trifluoromethyl)-4,5-dihydroisoxazol-3-yl)-N-(2-fluoroethyl)-2-methylbenzamide)Example 12: 4-(5-(3,5-dichlorophenyl)-5-(trifluoromethyl)-4,5-dihydroisoxazol-3-yl)-N-(2-fluoro Ethyl)-2-methylbenzamide (4-(5-(3,5-dichlorophenyl)-5-(trifluoromethyl)-4,5-dihydroisoxazol-3-yl)-N-(2-fluoroethyl)-2-methylbenzamide )
1H NMR (500 MHz, DMSO-d6) δ 8.59 (t, J = 5.6 Hz, 1H), 7.81 (t, J = 1.9 Hz, 1H), 7.64 - 7.58 (m, 4H), 7.42 (d, J = 7.8 Hz, 1H), 4.58 (t, J = 5.1 Hz, 1H), 4.49 (t, J = 5.0 Hz, 1H), 4.42 - 4.26 (m, 2H), 3.60 - 3.54 (m, 1H), 3.51 (q, J = 5.3 Hz, 1H), 2.37 (s, 3H)1H NMR (500 MHz, DMSO-d6) δ 8.59 (t, J = 5.6 Hz, 1H), 7.81 (t, J = 1.9 Hz, 1H), 7.64 - 7.58 (m, 4H), 7.42 (d, J = 7.8 Hz, 1H), 4.58 (t, J = 5.1 Hz, 1H), 4.49 (t, J = 5.0 Hz, 1H), 4.42 - 4.26 (m, 2H), 3.60 - 3.54 (m, 1H), 3.51 ( q, J = 5.3 Hz, 1H), 2.37 (s, 3H)
실시예 13: N-(2-클로로에틸)-4-(5-(4-클로로페닐)-5-(트리플루오로메틸)-4,5-다이하이드로아이소옥사졸-3-일)-2-메틸벤즈아마이드(N-(2-chloroethyl)-4-(5-(4-chlorophenyl)-5-(trifluoromethyl)-4,5-dihydroisoxazol-3-yl)-2-methylbenzamide)Example 13: N-(2-chloroethyl)-4-(5-(4-chlorophenyl)-5-(trifluoromethyl)-4,5-dihydroisoxazol-3-yl)-2 -Methylbenzamide (N-(2-chloroethyl)-4-(5-(4-chlorophenyl)-5-(trifluoromethyl)-4,5-dihydroisoxazol-3-yl)-2-methylbenzamide)
1H-NMR (CDCl3, 500Hz) δ 7.55 - 7.48 (m, 4H), 7.41 (dd, J = 8.5, 6.6 Hz, 3H), 6.17 (t, J = 5.5 Hz, 1H), 4.05 (d, J = 17.1 Hz, 1H), 3.80 - 3.72 (m, 4H), 3.69 (dd, J = 17.2, 0.9 Hz, 1H), 2.46 (s, 3H)1H-NMR (CDCl3, 500Hz) δ 7.55 - 7.48 (m, 4H), 7.41 (dd, J = 8.5, 6.6 Hz, 3H), 6.17 (t, J = 5.5 Hz, 1H), 4.05 (d, J = 17.1 Hz, 1H), 3.80 - 3.72 (m, 4H), 3.69 (dd, J = 17.2, 0.9 Hz, 1H), 2.46 (s, 3H)
실시예 14: 4-(5-(4-클로로페닐)-5-(트리플루오로메틸)-4,5-다이하이드로아이소옥사졸-3-일)-N-(2-플루오로에틸)-2-메틸벤즈아마이드(4-(5-(4-chlorophenyl)-5-(trifluoromethyl)-4,5-dihydroisoxazol-3-yl)-N-(2-fluoroethyl)-2-methylbenzamide)Example 14: 4-(5-(4-chlorophenyl)-5-(trifluoromethyl)-4,5-dihydroisoxazol-3-yl)-N-(2-fluoroethyl)- 2-methylbenzamide (4-(5-(4-chlorophenyl)-5-(trifluoromethyl)-4,5-dihydroisoxazol-3-yl)-N-(2-fluoroethyl)-2-methylbenzamide)
1H-NMR (CDCl3, 500Hz) δ 7.56 - 7.47 (m, 4H), 7.44 - 7.38 (m, 3H), 6.16 - 6.04 (m, 1H), 4.68 - 4.61 (m, 1H), 4.55 (dd, J = 5.1, 4.3 Hz, 1H), 4.05 (d, J = 17.1 Hz, 1H), 3.78 (dt, J = 6.0, 4.6 Hz, 1H), 3.74 - 3.70 (m, 1H), 3.70 - 3.65 (m, 1H), 2.46 (s, 3H)1H-NMR (CDCl3, 500Hz) δ 7.56 - 7.47 (m, 4H), 7.44 - 7.38 (m, 3H), 6.16 - 6.04 (m, 1H), 4.68 - 4.61 (m, 1H), 4.55 (dd, J = 5.1, 4.3 Hz, 1H), 4.05 (d, J = 17.1 Hz, 1H), 3.78 (dt, J = 6.0, 4.6 Hz, 1H), 3.74 - 3.70 (m, 1H), 3.70 - 3.65 (m, 1H), 2.46 (s, 3H)
실시예 15: N-(2-플루오로에틸)-4-(5-(4-플루오로페닐)-5-(트리플루오로메틸)-4,5-다이하이드로아이소옥사졸-3-일)-2-메틸벤즈아마이드(N-(2-fluoroethyl)-4-(5-(4-fluorophenyl)-5-(trifluoromethyl)-4,5-dihydroisoxazol-3-yl)-2-methylbenzamide)Example 15: N-(2-fluoroethyl)-4-(5-(4-fluorophenyl)-5-(trifluoromethyl)-4,5-dihydroisoxazol-3-yl) -2-methylbenzamide (N-(2-fluoroethyl)-4-(5-(4-fluorophenyl)-5-(trifluoromethyl)-4,5-dihydroisoxazol-3-yl)-2-methylbenzamide)
1H-NMR (CDCl3, 500Hz) δ 7.61 - 7.55 (m, 2H), 7.55 - 7.48 (m, 2H), 7.42 (d, J = 7.9 Hz, 1H), 7.15 - 7.09 (m, 2H), 6.10 (s, 1H), 4.64 (dd, J = 5.1, 4.3 Hz, 1H), 4.55 (dd, J = 5.2, 4.3 Hz, 1H), 4.06 (d, J = 17.1 Hz, 1H), 3.82 - 3.75 (m, 1H), 3.75 - 3.66 (m, 2H), 2.46 (s, 3H)1H-NMR (CDCl3, 500Hz) δ 7.61 - 7.55 (m, 2H), 7.55 - 7.48 (m, 2H), 7.42 (d, J = 7.9 Hz, 1H), 7.15 - 7.09 (m, 2H), 6.10 ( s, 1H), 4.64 (dd, J = 5.1, 4.3 Hz, 1H), 4.55 (dd, J = 5.2, 4.3 Hz, 1H), 4.06 (d, J = 17.1 Hz, 1H), 3.82 - 3.75 (m , 1H), 3.75 - 3.66 (m, 2H), 2.46 (s, 3H)
실시예 16: 4-(5-(3,5-다이클로로-4-플루오로페닐)-5-(트리플루오로메틸)-4,5-다이하이드로아이소옥사졸-3-일)-N-(2-플루오로에틸)-2-메틸벤즈아마이드(4-(5-(3,5-dichloro-4-fluorophenyl)-5-(trifluoromethyl)-4,5-dihydroisoxazol-3-yl)-N-(2-fluoroethyl)-2-methylbenzamide)Example 16: 4-(5-(3,5-dichloro-4-fluorophenyl)-5-(trifluoromethyl)-4,5-dihydroisoxazol-3-yl)-N- (2-Fluoroethyl)-2-methylbenzamide (4-(5-(3,5-dichloro-4-fluorophenyl)-5-(trifluoromethyl)-4,5-dihydroisoxazol-3-yl)-N- (2-fluoroethyl)-2-methylbenzamide)
1H-NMR (CDCl3, 500Hz) δ 7.57 (d, J = 6.1 Hz, 2H), 7.52 - 7.47 (m, 2H), 7.42 (d, J = 7.9 Hz, 1H), 6.20 - 6.02 (m, 1H), 4.64 (dd, J = 5.0, 4.4 Hz, 1H), 4.55 (dd, J = 5.1, 4.3 Hz, 1H), 4.06 (d, J = 17.2 Hz, 1H), 3.78 (dt, J = 6.0, 4.7 Hz, 1H), 3.72 (dt, J = 6.0, 4.6 Hz, 1H), 3.67 (dd, J = 17.2, 0.9 Hz, 1H), 2.46 (s, 3H)1H-NMR (CDCl3, 500Hz) δ 7.57 (d, J = 6.1 Hz, 2H), 7.52 - 7.47 (m, 2H), 7.42 (d, J = 7.9 Hz, 1H), 6.20 - 6.02 (m, 1H) , 4.64 (dd, J = 5.0, 4.4 Hz, 1H), 4.55 (dd, J = 5.1, 4.3 Hz, 1H), 4.06 (d, J = 17.2 Hz, 1H), 3.78 (dt, J = 6.0, 4.7 Hz, 1H), 3.72 (dt, J = 6.0, 4.6 Hz, 1H), 3.67 (dd, J = 17.2, 0.9 Hz, 1H), 2.46 (s, 3H)
실시예 17: 4-(5-(3,5-다이플루오로페닐)-5-(트리플루오로메틸)-4,5-다이하이드로아이소옥사졸-3-일)-N-(2-플루오로에틸)-2-메틸벤즈아마이드(4-(5-(3,5-difluorophenyl)-5-(trifluoromethyl)-4,5-dihydroisoxazol-3-yl)-N-(2-fluoroethyl)-2-methylbenzamide)Example 17: 4-(5-(3,5-difluorophenyl)-5-(trifluoromethyl)-4,5-dihydroisoxazol-3-yl)-N-(2-fluo Roethyl)-2-methylbenzamide (4-(5-(3,5-difluorophenyl)-5-(trifluoromethyl)-4,5-dihydroisoxazol-3-yl)-N-(2-fluoroethyl)-2- methylbenzamide)
1H-NMR (CDCl3, 500Hz) δ 7.50 (dt, J = 1.5, 0.8 Hz, 1H), 7.49 (dd, J = 7.9, 2.4 Hz, 1H), 7.42 (d, J = 7.9 Hz, 1H), 7.18 - 7.11 (m, 2H), 6.86 (tt, J = 8.5, 2.3 Hz, 1H), 6.16 - 6.08 (m, 1H), 4.64 (dd, J = 5.0, 4.4 Hz, 1H), 4.55 (dd, J = 5.1, 4.3 Hz, 1H), 4.06 (d, J = 17.1 Hz, 1H), 3.77 (dt, J = 6.0, 4.7 Hz, 1H), 3.72 (dt, J = 6.0, 4.7 Hz, 1H), 3.70 - 3.65 (m, 1H), 2.46 (s, 3H)1H-NMR (CDCl3, 500Hz) δ 7.50 (dt, J = 1.5, 0.8 Hz, 1H), 7.49 (dd, J = 7.9, 2.4 Hz, 1H), 7.42 (d, J = 7.9 Hz, 1H), 7.18 - 7.11 (m, 2H), 6.86 (tt, J = 8.5, 2.3 Hz, 1H), 6.16 - 6.08 (m, 1H), 4.64 (dd, J = 5.0, 4.4 Hz, 1H), 4.55 (dd, J) = 5.1, 4.3 Hz, 1H), 4.06 (d, J = 17.1 Hz, 1H), 3.77 (dt, J = 6.0, 4.7 Hz, 1H), 3.72 (dt, J = 6.0, 4.7 Hz, 1H), 3.70 - 3.65 (m, 1H), 2.46 (s, 3H)
실시예 18: 4-(5-(3-클로로-5-(트리플루오로메틸)페닐)-5-(트리플루오로메틸)-4,5-다이하이드로아이소옥사졸-3-일)-N-(2-플루오로에틸)-2-메틸벤즈아마이드(4-(5-(3-chloro-5-(trifluoromethyl)phenyl)-5-(trifluoromethyl)-4,5-dihydroisoxazol-3-yl)-N-(2-fluoroethyl)-2-methylbenzamide)Example 18: 4-(5-(3-chloro-5-(trifluoromethyl)phenyl)-5-(trifluoromethyl)-4,5-dihydroisoxazol-3-yl)-N -(2-Fluoroethyl)-2-methylbenzamide (4-(5-(3-chloro-5-(trifluoromethyl)phenyl)-5-(trifluoromethyl)-4,5-dihydroisoxazol-3-yl)- N-(2-fluoroethyl)-2-methylbenzamide)
1H-NMR (CDCl3, 500Hz) δ 7.80 (t, J = 2.0 Hz, 1H), 7.74 (s, 1H), 7.69 - 7.65 (m, 1H), 7.54 - 7.49 (m, 2H), 7.43 (d, J = 7.8 Hz, 1H), 6.10 (t, J = 5.6 Hz, 1H), 4.64 (dd, J = 5.1, 4.3 Hz, 1H), 4.55 (dd, J = 5.0, 4.3 Hz, 1H), 4.12 (d, J = 17.2 Hz, 1H), 3.78 (dt, J = 6.0, 4.7 Hz, 1H), 3.74 - 3.68 (m, 2H), 2.47 (s, 3H)1H-NMR (CDCl3, 500Hz) δ 7.80 (t, J = 2.0 Hz, 1H), 7.74 (s, 1H), 7.69 - 7.65 (m, 1H), 7.54 - 7.49 (m, 2H), 7.43 (d, J = 7.8 Hz, 1H), 6.10 (t, J = 5.6 Hz, 1H), 4.64 (dd, J = 5.1, 4.3 Hz, 1H), 4.55 (dd, J = 5.0, 4.3 Hz, 1H), 4.12 ( d, J = 17.2 Hz, 1H), 3.78 (dt, J = 6.0, 4.7 Hz, 1H), 3.74 - 3.68 (m, 2H), 2.47 (s, 3H)
실시예 19: N-((1-(클로로메틸)사이클로프로필)메틸)-4-(5-(3,5-다이클로로페닐)-5-(트리플루오로메틸)-4,5-다이하이드로아이소옥사졸-3-일)-2-메틸벤즈아마이드(N-((1-(chloromethyl)cyclopropyl)methyl)-4-(5-(3,5-dichlorophenyl)-5-(trifluoromethyl)-4,5-dihydroisoxazol-3-yl)-2-methylbenzamide)Example 19: N-((1-(chloromethyl)cyclopropyl)methyl)-4-(5-(3,5-dichlorophenyl)-5-(trifluoromethyl)-4,5-dihydro Isoxazol-3-yl)-2-methylbenzamide (N-((1-(chloromethyl)cyclopropyl)methyl)-4-(5-(3,5-dichlorophenyl)-5-(trifluoromethyl)-4, 5-dihydroisoxazol-3-yl)-2-methylbenzamide)
1H NMR (500 MHz, CDCl3) δ 7.51 - 7.48 (m, 4H), 7.44 - 7.40 (m, 2H), 6.14 (t, J = 5.9 Hz, 1H), 4.06 (d, J = 17.2 Hz, 1H), 3.68 (d, J = 17.4 Hz, 1H), 3.55 (s, 2H), 3.54 (d, J = 6.0 Hz, 2H), 2.46 (s, 3H), 0.84 - 0.81 (m, 2H), 0.70 - 0.67 (m, 2H)1H NMR (500 MHz, CDCl3) δ 7.51 - 7.48 (m, 4H), 7.44 - 7.40 (m, 2H), 6.14 (t, J = 5.9 Hz, 1H), 4.06 (d, J = 17.2 Hz, 1H) , 3.68 (d, J = 17.4 Hz, 1H), 3.55 (s, 2H), 3.54 (d, J = 6.0 Hz, 2H), 2.46 (s, 3H), 0.84 - 0.81 (m, 2H), 0.70 - 0.67 (m, 2H)
실시예 20: N-((1-(클로로메틸)사이클로뷰틸)메틸)-4-(5-(3,5-다이클로로페닐)-5-(트리플루오로메틸)-4,5-다이하이드로아이소옥사졸-3-일)-2-메틸벤즈아마이드(N-((1-(chloromethyl)cyclobutyl)methyl)-4-(5-(3,5-dichlorophenyl)-5-(trifluoromethyl)-4,5-dihydroisoxazol-3-yl)-2-methylbenzamide)Example 20: N-((1-(chloromethyl)cyclobutyl)methyl)-4-(5-(3,5-dichlorophenyl)-5-(trifluoromethyl)-4,5-dihydro Isoxazol-3-yl)-2-methylbenzamide (N-((1-(chloromethyl)cyclobutyl)methyl)-4-(5-(3,5-dichlorophenyl)-5-(trifluoromethyl)-4, 5-dihydroisoxazol-3-yl)-2-methylbenzamide)
1H NMR (500 MHz, CDCl3) δ 7.49 (dt, J = 4.2, 2.1 Hz, 4H), 7.42 - 7.37 (m, 2H), 5.96 (t, J = 6.4 Hz, 1H), 4.06 (d, J = 17.2 Hz, 1H), 3.75 - 3.61 (m, 5H), 2.45 (s, 3H), 2.02 - 1.86 (m, 6H)1H NMR (500 MHz, CDCl3) δ 7.49 (dt, J = 4.2, 2.1 Hz, 4H), 7.42 - 7.37 (m, 2H), 5.96 (t, J = 6.4 Hz, 1H), 4.06 (d, J = 17.2 Hz, 1H), 3.75 - 3.61 (m, 5H), 2.45 (s, 3H), 2.02 - 1.86 (m, 6H)
실시예 21: N-(3-클로로프로필)-4-(5-(3,5-다이클로로페닐)-5-(트리플루오로메틸)-4,5-다이하이드로아이소옥사졸-3-일)-2-메틸벤즈아마이드(N-(3-chloropropyl)-4-(5-(3,5-dichlorophenyl)-5-(trifluoromethyl)-4,5-dihydroisoxazol-3-yl)-2-methylbenzamide)Example 21: N-(3-chloropropyl)-4-(5-(3,5-dichlorophenyl)-5-(trifluoromethyl)-4,5-dihydroisoxazol-3-yl )-2-methylbenzamide (N-(3-chloropropyl)-4-(5-(3,5-dichlorophenyl)-5-(trifluoromethyl)-4,5-dihydroisoxazol-3-yl)-2-methylbenzamide)
1H NMR (300 MHz, CDCl3) δ 7.52-7.49 (m, 4 H), 7.43-7.39 (m, 2 H), 5.96 (t, J = 5.7 Hz, 1 H), 4.08 (d, J = 17.2 Hz, 1 H), 3.72-3.59 (m, 5 H) 2.47 (s, 3 H), 2.13 (quint, J = 6.3 Hz, 2 H)1H NMR (300 MHz, CDCl3) δ 7.52-7.49 (m, 4 H), 7.43-7.39 (m, 2 H), 5.96 (t, J = 5.7 Hz, 1 H), 4.08 (d, J = 17.2 Hz) , 1 H), 3.72-3.59 (m, 5 H) 2.47 (s, 3 H), 2.13 (quint, J = 6.3 Hz, 2 H)
실시예 22: N-(4-클로로뷰틸)-4-(5-(3,5-다이클로로페닐)-5-(트리플루오로메틸)-4,5-다이하이드로아이소옥사졸-3-일)-2-메틸벤즈아마이드(N-(4-chlorobutyl)-4-(5-(3,5-dichlorophenyl)-5-(trifluoromethyl)-4,5-dihydroisoxazol-3-yl)-2-methylbenzamide)Example 22: N-(4-chlorobutyl)-4-(5-(3,5-dichlorophenyl)-5-(trifluoromethyl)-4,5-dihydroisoxazol-3-yl )-2-methylbenzamide (N-(4-chlorobutyl)-4-(5-(3,5-dichlorophenyl)-5-(trifluoromethyl)-4,5-dihydroisoxazol-3-yl)-2-methylbenzamide)
1H NMR (300 MHz, CDCl3) δ 7.51-7.49 (m, 4 H), 7.43-7.38 (m, 2 H), 5.79 (t, J = 6.3 Hz, 1 H), 4.08 (d, J = 17.4 Hz, 1 H), 3.69 (d, J = 17.1 Hz, 1 H), 3.61 (t, J = 6.0 Hz, 2 H), 3.49 (q, J = 6.6 Hz, 2 H), 2.47 (s, 3 H), 1.94-1.74 (m, 4 H)1H NMR (300 MHz, CDCl3) δ 7.51-7.49 (m, 4 H), 7.43-7.38 (m, 2 H), 5.79 (t, J = 6.3 Hz, 1 H), 4.08 (d, J = 17.4 Hz) , 1 H), 3.69 (d, J = 17.1 Hz, 1 H), 3.61 (t, J = 6.0 Hz, 2 H), 3.49 (q, J = 6.6 Hz, 2 H), 2.47 (s, 3 H) ), 1.94-1.74 (m, 4 H)
실시예 23: N-(2-클로로에틸)-4-(5-(3,5-다이클로로페닐)-5-(트리플루오로메틸)-4,5-다이하이드로아이소옥사졸-3-일)-1-나프트아마이드(N-(2-chloroethyl)-4-(5-(3,5-dichlorophenyl)-5-(trifluoromethyl)-4,5-dihydroisoxazol-3-yl)-1-naphthamide)Example 23: N-(2-chloroethyl)-4-(5-(3,5-dichlorophenyl)-5-(trifluoromethyl)-4,5-dihydroisoxazol-3-yl )-1-naphthamide (N-(2-chloroethyl)-4-(5-(3,5-dichlorophenyl)-5-(trifluoromethyl)-4,5-dihydroisoxazol-3-yl)-1-naphthamide)
1H NMR (300 MHz, CDCl3) δ 8.90 - 8.80 (m, 1H), 8.38 - 8.27 (m, 1H), 7.75 - 7.60 (m, 3H), 7.60 - 7.49 (m, 3H), 7.46 (t, J = 1.8 Hz, 1H), 6.40 (s, 1H), 4.27 (d, J = 17.3 Hz, 1H), 3.97 - 3.78 (m, 5H).1H NMR (300 MHz, CDCl3) δ 8.90 - 8.80 (m, 1H), 8.38 - 8.27 (m, 1H), 7.75 - 7.60 (m, 3H), 7.60 - 7.49 (m, 3H), 7.46 (t, J = 1.8 Hz, 1H), 6.40 (s, 1H), 4.27 (d, J = 17.3 Hz, 1H), 3.97 - 3.78 (m, 5H).
실시예 24: N-(2-클로로프로필)-4-(5-(3,5-다이클로로페닐)-5-(트리플루오로메틸)-4,5-다이하이드로아이소옥사졸-3-일)-1-나프트아마이드(N-(2-chloropropyl)-4-(5-(3,5-dichlorophenyl)-5-(trifluoromethyl)-4,5-dihydroisoxazol-3-yl)-1-naphthamide)Example 24: N-(2-chloropropyl)-4-(5-(3,5-dichlorophenyl)-5-(trifluoromethyl)-4,5-dihydroisoxazol-3-yl )-1-naphthamide (N-(2-chloropropyl)-4-(5-(3,5-dichlorophenyl)-5-(trifluoromethyl)-4,5-dihydroisoxazol-3-yl)-1-naphthamide)
1H NMR (400 MHz, CDCl3) δ 8.87-8.78 (m, 1H), 8.36-8.27 (m, 1H), 7.69-7.43 (m, 7H), 6.44 (s, 1H), 4.43-4.33 (m, 1H), 4.26 (d, J = 17.2Hz, 1H), 4.10-4.02 (m, 1H), 3.89 (d, J = 17.4Hz, 1H), 3.57-3.47 (m, 1H), 1.63 (d, J = 6.6Hz, 3H)1H NMR (400 MHz, CDCl3) δ 8.87-8.78 (m, 1H), 8.36-8.27 (m, 1H), 7.69-7.43 (m, 7H), 6.44 (s, 1H), 4.43-4.33 (m, 1H) ), 4.26 (d, J = 17.2Hz, 1H), 4.10-4.02 (m, 1H), 3.89 (d, J = 17.4Hz, 1H), 3.57-3.47 (m, 1H), 1.63 (d, J = 6.6Hz, 3H)
실시예 25: 4-(5-(3,5-다이클로로페닐)-5-(트리플루오로메틸)-4,5-다이하이드로아이소옥사졸-3-일)-N-(1,3-다이클로로프로판-2-일)-1-나프트아마이드(4-(5-(3,5-dichlorophenyl)-5-(trifluoromethyl)-4,5-dihydroisoxazol-3-yl)-N-(1,3-dichloropropan-2-yl)-1-naphthamide)Example 25: 4-(5-(3,5-dichlorophenyl)-5-(trifluoromethyl)-4,5-dihydroisoxazol-3-yl)-N-(1,3- Dichloropropan-2-yl)-1-naphthamide (4-(5-(3,5-dichlorophenyl)-5-(trifluoromethyl)-4,5-dihydroisoxazol-3-yl)-N-(1, 3-dichloropropan-2-yl)-1-naphthamide)
1H NMR (300 MHz, CDCl3) δ 8.85-8.78 (m, 1H), 8.31-8.24 (m, 1H), 7.71-7.55 (m, 5H), 7.52-7.44 (m, 2H), 6.41 (d, J = 8.4Hz, 1H), 4.85-4.75 (m, 1H), 4.25 (d, J = 17.2Hz, 1H), 3.97 (dd, J = 4.6Hz, J = 11.4Hz, 2H), 3.93-3.81 (m, 3H)1H NMR (300 MHz, CDCl3) δ 8.85-8.78 (m, 1H), 8.31-8.24 (m, 1H), 7.71-7.55 (m, 5H), 7.52-7.44 (m, 2H), 6.41 (d, J = 8.4Hz, 1H), 4.85-4.75 (m, 1H), 4.25 (d, J = 17.2Hz, 1H), 3.97 (dd, J = 4.6Hz, J = 11.4Hz, 2H), 3.93-3.81 (m , 3H)
실시예 26: N-(1-(클로로메틸)사이클로프로필)-4-(5-(3,5-다이클로로페닐)-5-(트리플루오로메틸)-4,5-다이하이드로아이소옥사졸-3-일)-1-나프트아마이드(N-(1-(chloromethyl)cyclopropyl)-4-(5-(3,5-dichlorophenyl)-5-(trifluoromethyl)-4,5-dihydroisoxazol-3-yl)-1-naphthamide)Example 26: N-(1-(chloromethyl)cyclopropyl)-4-(5-(3,5-dichlorophenyl)-5-(trifluoromethyl)-4,5-dihydroisoxazole -3-yl)-1-naphtamide (N-(1-(chloromethyl)cyclopropyl)-4-(5-(3,5-dichlorophenyl)-5-(trifluoromethyl)-4,5-dihydroisoxazol-3- yl)-1-naphthamide)
1H NMR (500 MHz, CDCl3) δ 8.84-8.81 (m, 1H), 8.32-8.28 (m, 1H), 7.70-7.63 (m, 2H), 7.59 (d, J = 7.4Hz, 1H), 7.56 (s, 2H), 7.50 (d, J = 7.4Hz, 1H), 7.46 (t, J = 1.9Hz, 1H), 6.52 (s, 1H), 4.25 (d, J = 17.2Hz, 1H), 3.93 (s, 2H), 3.89 (d, J = 17.2Hz, 1H), 1.20-1.08 (m, 4H)1H NMR (500 MHz, CDCl3) δ 8.84-8.81 (m, 1H), 8.32-8.28 (m, 1H), 7.70-7.63 (m, 2H), 7.59 (d, J = 7.4Hz, 1H), 7.56 ( s, 2H), 7.50 (d, J = 7.4Hz, 1H), 7.46 (t, J = 1.9Hz, 1H), 6.52 (s, 1H), 4.25 (d, J = 17.2Hz, 1H), 3.93 ( s, 2H), 3.89 (d, J = 17.2Hz, 1H), 1.20-1.08 (m, 4H)
실시예 27: N-(3-클로로-1,1,1-트리플루오로프로판-2-일)-4-(5-(3,5-다이클로로페닐)-5-(트리플루오로메틸)-4,5-다이하이드로아이소옥사졸-3-일)-1-나프트아마이드(N-(3-chloro-1,1,1-trifluoropropan-2-yl)-4-(5-(3,5-dichlorophenyl)-5-(trifluoromethyl)-4,5-dihydroisoxazol-3-yl)-1-naphthamide)Example 27: N-(3-chloro-1,1,1-trifluoropropan-2-yl)-4-(5-(3,5-dichlorophenyl)-5-(trifluoromethyl) -4,5-dihydroisoxazol-3-yl)-1-naphthamide (N-(3-chloro-1,1,1-trifluoropropan-2-yl)-4-(5-(3, 5-dichlorophenyl)-5-(trifluoromethyl)-4,5-dihydroisoxazol-3-yl)-1-naphthamide)
1H NMR (500 MHz, CDCl3) δ8.87 - 8.80 (m, 1H), 8.36 - 8.25 (m, 1H), 7.77 - 7.63 (m, 3H), 7.59 (d, J = 1.8 Hz, 2H), 7.54 (d, J = 7.4 Hz, 1H), 7.49 (t, J = 1.8 Hz, 1H), 5.35 (dtd, J = 10.0, 6.8, 4.1 Hz, 1H), 4.28 (dd, J = 17.2, 0.6 Hz, 1H), 4.01 (dd, J = 12.3, 4.2 Hz, 1H), 3.95 - 3.91 (m, 1H), 3.91 - 3.87 (m, 1H) 1 H NMR (500 MHz, CDCl 3 ) δ8.87 - 8.80 (m, 1H), 8.36 - 8.25 (m, 1H), 7.77 - 7.63 (m, 3H), 7.59 (d, J = 1.8 Hz, 2H) , 7.54 (d, J = 7.4 Hz, 1H), 7.49 (t, J = 1.8 Hz, 1H), 5.35 (dtd, J = 10.0, 6.8, 4.1 Hz, 1H), 4.28 (dd, J = 17.2, 0.6) Hz, 1H), 4.01 (dd, J = 12.3, 4.2 Hz, 1H), 3.95 - 3.91 (m, 1H), 3.91 - 3.87 (m, 1H)
실시예 28: N-(3-(클로로메틸)옥세탄-3-일)-4-(5-(3,5-다이클로로페닐)-5-(트리플루오로메틸)-4,5-다이하이드로아이소옥사졸-3-일)-1-나프트아마이드(N-(3-(chloromethyl)oxetan-3-yl)-4-(5-(3,5-dichlorophenyl)-5-(trifluoromethyl)-4,5-dihydroisoxazol-3-yl)-1-naphthamide)Example 28: N-(3-(chloromethyl)oxetan-3-yl)-4-(5-(3,5-dichlorophenyl)-5-(trifluoromethyl)-4,5-di Hydroisoxazol-3-yl)-1-naphthamide (N-(3-(chloromethyl)oxetan-3-yl)-4-(5-(3,5-dichlorophenyl)-5-(trifluoromethyl)- 4,5-dihydroisoxazol-3-yl)-1-naphthamide)
1H NMR (500 MHz, CDCl3) δ 9.08 - 9.03 (m, 1H), 8.83 - 8.78 (m, 1H), 8.04 (d, J = 7.6 Hz, 1H), 7.73 - 7.64 (m, 2H), 7.59 - 7.52 (m, 3H), 7.46 (t, J = 1.9 Hz, 1H), 4.55 (s, 2H), 4.27 (d, J = 17.3 Hz, 1H), 3.96 (dd, J = 11.4, 1.3 Hz, 2H), 3.90 (d, J = 17.3 Hz, 1H), 3.85 (dd, J = 11.4, 1.4 Hz, 2H)1H NMR (500 MHz, CDCl3) δ 9.08 - 9.03 (m, 1H), 8.83 - 8.78 (m, 1H), 8.04 (d, J = 7.6 Hz, 1H), 7.73 - 7.64 (m, 2H), 7.59 - 7.52 (m, 3H), 7.46 (t, J = 1.9 Hz, 1H), 4.55 (s, 2H), 4.27 (d, J = 17.3 Hz, 1H), 3.96 (dd, J = 11.4, 1.3 Hz, 2H) ), 3.90 (d, J = 17.3 Hz, 1H), 3.85 (dd, J = 11.4, 1.4 Hz, 2H)
실시예 29: N-(2-클로로에틸)-4-(5-(3,5-다이클로로-4-플루오로페닐)-5-(트리플루오로메틸)-4,5-다이하이드로아이소옥사졸-3-일)-1-나프트아마이드(N-(2-chloroethyl)-4-(5-(3,5-dichloro-4-fluorophenyl)-5-(trifluoromethyl)-4,5-dihydroisoxazol-3-yl)-1-naphthamide)Example 29: N-(2-chloroethyl)-4-(5-(3,5-dichloro-4-fluorophenyl)-5-(trifluoromethyl)-4,5-dihydroisox sazol-3-yl)-1-naphtamide (N-(2-chloroethyl)-4-(5-(3,5-dichloro-4-fluorophenyl)-5-(trifluoromethyl)-4,5-dihydroisoxazol- 3-yl)-1-naphthamide)
1H NMR (500 MHz, DMSO-d6) δ 8.93 (s, 1H), 8.80 - 8.76 (m, 1H), 8.27 - 8.23 (m, 1H), 7.89 (dd, J = 6.9, 4.0 Hz, 3H), 7.78 - 7.64 (m, 3H), 4.54 (s, 2H), 3.89 - 3.81 (m, 2H), 3.69 (t, J = 6.0 Hz, 2H)1H NMR (500 MHz, DMSO-d6) δ 8.93 (s, 1H), 8.80 - 8.76 (m, 1H), 8.27 - 8.23 (m, 1H), 7.89 (dd, J = 6.9, 4.0 Hz, 3H), 7.78 - 7.64 (m, 3H), 4.54 (s, 2H), 3.89 - 3.81 (m, 2H), 3.69 (t, J = 6.0 Hz, 2H)
실시예 30: 4-(5-(3-클로로-5-(트리플루오로메틸)페닐)-5-(트리플루오로메틸)-4,5-다이하이드로아이소옥사졸-3-일)-N-(2-클로로에틸)-1-나프트아마이드(4-(5-(3-chloro-5-(trifluoromethyl)phenyl)-5-(trifluoromethyl)-4,5-dihydroisoxazol-3-yl)-N-(2-chloroethyl)-1-naphthamide)Example 30: 4-(5-(3-chloro-5-(trifluoromethyl)phenyl)-5-(trifluoromethyl)-4,5-dihydroisoxazol-3-yl)-N -(2-Chloroethyl)-1-naphtamide (4-(5-(3-chloro-5-(trifluoromethyl)phenyl)-5-(trifluoromethyl)-4,5-dihydroisoxazol-3-yl)-N -(2-chloroethyl)-1-naphthamide)
1H NMR (500 MHz, DMSO-d6) δ 8.93 (t, J = 5.7 Hz, 1H), 8.82 - 8.76 (m, 1H), 8.29 - 8.23 (m, 1H), 8.08 (dt, J = 27.6, 1.8 Hz, 2H), 7.96 - 7.88 (m, 2H), 7.77 - 7.62 (m, 3H), 4.61 (d, J = 1.5 Hz, 2H), 3.84 (t, J = 6.1 Hz, 2H), 3.69 (q, J = 6.2 Hz, 2H)1H NMR (500 MHz, DMSO-d6) δ 8.93 (t, J = 5.7 Hz, 1H), 8.82 - 8.76 (m, 1H), 8.29 - 8.23 (m, 1H), 8.08 (dt, J = 27.6, 1.8 Hz, 2H), 7.96 - 7.88 (m, 2H), 7.77 - 7.62 (m, 3H), 4.61 (d, J = 1.5 Hz, 2H), 3.84 (t, J = 6.1 Hz, 2H), 3.69 (q) , J = 6.2 Hz, 2H)
실시예 31: N-(2-브로모에틸)-4-(5-(3,5-다이클로로페닐)-5-(트리플루오로메틸)-4,5-다이하이드로아이소옥사졸-3-일)-1-나프트아마이드(N-(2-bromoethyl)-4-(5-(3,5-dichlorophenyl)-5-(trifluoromethyl)-4,5-dihydroisoxazol-3-yl)-1-naphthamide)Example 31: N-(2-bromoethyl)-4-(5-(3,5-dichlorophenyl)-5-(trifluoromethyl)-4,5-dihydroisoxazole-3- 1)-1-naphthamide (N-(2-bromoethyl)-4-(5-(3,5-dichlorophenyl)-5-(trifluoromethyl)-4,5-dihydroisoxazol-3-yl)-1-naphthamide )
1H NMR (500 MHz, DMSO-d6) δ 9.26 - 9.20 (m, 1H), 8.82 - 8.77 (m, 1H), 8.09 (d, J = 7.6 Hz, 1H), 7.93 (d, J = 7.8 Hz, 1H), 7.83 (t, J = 1.8 Hz, 1H), 7.74 - 7.71 (m, 2H), 7.70 (d, J = 1.8 Hz, 2H), 4.61 - 4.50 (m, 2H), 4.50 - 4.44 (m, 2H), 4.20 - 4.14 (m, 2H)1H NMR (500 MHz, DMSO-d6) δ 9.26 - 9.20 (m, 1H), 8.82 - 8.77 (m, 1H), 8.09 (d, J = 7.6 Hz, 1H), 7.93 (d, J = 7.8 Hz, 1H), 7.83 (t, J = 1.8 Hz, 1H), 7.74 - 7.71 (m, 2H), 7.70 (d, J = 1.8 Hz, 2H), 4.61 - 4.50 (m, 2H), 4.50 - 4.44 (m) , 2H), 4.20 - 4.14 (m, 2H)
실시예 32: 4-(5-(3,5-다이클로로페닐)-5-(트리플루오로메틸)-4,5-다이하이드로아이소옥사졸-3-일)-N-(2-플루오로에틸)-1-나프트아마이드(4-(5-(3,5-dichlorophenyl)-5-(trifluoromethyl)-4,5-dihydroisoxazol-3-yl)-N-(2-fluoroethyl)-1-naphthamide)Example 32: 4-(5-(3,5-dichlorophenyl)-5-(trifluoromethyl)-4,5-dihydroisoxazol-3-yl)-N-(2-fluoro Ethyl)-1-naphthamide (4-(5-(3,5-dichlorophenyl)-5-(trifluoromethyl)-4,5-dihydroisoxazol-3-yl)-N-(2-fluoroethyl)-1-naphthamide )
1H NMR (500 MHz, DMSO-d6) δ 8.91 (t, J = 5.6 Hz, 1H), 8.79 (ddd, J = 8.5, 1.5, 0.7 Hz, 1H), 8.23 - 8.19 (m, 1H), 7.90 (d, J = 7.5 Hz, 1H), 7.83 (t, J = 1.9 Hz, 1H), 7.74 - 7.67 (m, 4H), 7.66 - 7.63 (m, 1H), 4.67 (t, J = 5.0 Hz, 1H), 4.58 (t, J = 5.1 Hz, 1H), 4.55 (d, J = 3.4 Hz, 2H), 3.72 - 3.61 (m, 2H)1H NMR (500 MHz, DMSO-d6) δ 8.91 (t, J = 5.6 Hz, 1H), 8.79 (ddd, J = 8.5, 1.5, 0.7 Hz, 1H), 8.23 - 8.19 (m, 1H), 7.90 ( d, J = 7.5 Hz, 1H), 7.83 (t, J = 1.9 Hz, 1H), 7.74 - 7.67 (m, 4H), 7.66 - 7.63 (m, 1H), 4.67 (t, J = 5.0 Hz, 1H) ), 4.58 (t, J = 5.1 Hz, 1H), 4.55 (d, J = 3.4 Hz, 2H), 3.72 - 3.61 (m, 2H)
실시예 33: N-(2-클로로에틸)-4-(5-(3,5-다이플루오로페닐)-5-(트리플루오로메틸)-4,5-다이하이드로아이소옥사졸-3-일)-1-나프트아마이드(N-(2-chloroethyl)-4-(5-(3,5-difluorophenyl)-5-(trifluoromethyl)-4,5-dihydroisoxazol-3-yl)-1-naphthamide)Example 33: N-(2-chloroethyl)-4-(5-(3,5-difluorophenyl)-5-(trifluoromethyl)-4,5-dihydroisoxazole-3- 1)-1-naphthamide (N-(2-chloroethyl)-4-(5-(3,5-difluorophenyl)-5-(trifluoromethyl)-4,5-dihydroisoxazol-3-yl)-1-naphthamide )
1H NMR (500 MHz, DMSO-d6) δ 8.92 (t, J = 5.7 Hz, 1H), 8.81 - 8.76 (m, 1H), 8.25 (dd, J = 8.8, 1.6 Hz, 1H), 7.90 (d, J = 7.5 Hz, 1H), 7.73 - 7.63 (m, 3H), 7.47 (tt, J = 9.3, 2.4 Hz, 1H), 7.44 - 7.39 (m, 2H), 4.59 - 4.45 (m, 2H), 3.83 (t, J = 6.1 Hz, 2H), 3.72 - 3.65 (m, 2H)1H NMR (500 MHz, DMSO-d6) δ 8.92 (t, J = 5.7 Hz, 1H), 8.81 - 8.76 (m, 1H), 8.25 (dd, J = 8.8, 1.6 Hz, 1H), 7.90 (d, J = 7.5 Hz, 1H), 7.73 - 7.63 (m, 3H), 7.47 (tt, J = 9.3, 2.4 Hz, 1H), 7.44 - 7.39 (m, 2H), 4.59 - 4.45 (m, 2H), 3.83 (t, J = 6.1 Hz, 2H), 3.72 - 3.65 (m, 2H)
실시예 34: N-(2-클로로에틸)-4-(5-(4-클로로페닐)-5-(트리플루오로메틸)-4,5-다이하이드로아이소옥사졸-3-일)-1-나프트아마이드(N-(2-chloroethyl)-4-(5-(4-chlorophenyl)-5-(trifluoromethyl)-4,5-dihydroisoxazol-3-yl)-1-naphthamide)Example 34: N-(2-chloroethyl)-4-(5-(4-chlorophenyl)-5-(trifluoromethyl)-4,5-dihydroisoxazol-3-yl)-1 -Naphthamide (N-(2-chloroethyl)-4-(5-(4-chlorophenyl)-5-(trifluoromethyl)-4,5-dihydroisoxazol-3-yl)-1-naphthamide)
1H-NMR (CDCl3, 500Hz) δ 8.83 - 8.77 (m, 1H), 8.32 - 8.26 (m, 1H), 7.66 - 7.61 (m, 2H), 7.61 - 7.56 (m, 3H), 7.49 (d, J = 7.5 Hz, 1H), 7.46 - 7.42 (m, 2H), 6.39 (t, J = 5.5 Hz, 1H), 4.23 (d, J = 17.2 Hz, 1H), 3.91 - 3.85 (m, 3H), 3.84 - 3.79 (m, 2H)1H-NMR (CDCl3, 500Hz) δ 8.83 - 8.77 (m, 1H), 8.32 - 8.26 (m, 1H), 7.66 - 7.61 (m, 2H), 7.61 - 7.56 (m, 3H), 7.49 (d, J = 7.5 Hz, 1H), 7.46 - 7.42 (m, 2H), 6.39 (t, J = 5.5 Hz, 1H), 4.23 (d, J = 17.2 Hz, 1H), 3.91 - 3.85 (m, 3H), 3.84 - 3.79 (m, 2H)
실시예 35: 4-(5-(4-클로로페닐)-5-(트리플루오로메틸)-4,5-다이하이드로아이소옥사졸-3-일)-N-(2-플루오로에틸)-1-나프트아마이드(4-(5-(4-chlorophenyl)-5-(trifluoromethyl)-4,5-dihydroisoxazol-3-yl)-N-(2-fluoroethyl)-1-naphthamide)Example 35: 4-(5-(4-chlorophenyl)-5-(trifluoromethyl)-4,5-dihydroisoxazol-3-yl)-N-(2-fluoroethyl)- 1-naphthamide (4-(5-(4-chlorophenyl)-5-(trifluoromethyl)-4,5-dihydroisoxazol-3-yl)-N-(2-fluoroethyl)-1-naphthamide)
1H-NMR (CDCl3, 500Hz) δ 8.82 - 8.77 (m, 1H), 8.30 - 8.24 (m, 1H), 7.66 - 7.56 (m, 5H), 7.48 (d, J = 7.3 Hz, 1H), 7.46 - 7.42 (m, 2H),1H-NMR (CDCl3, 500Hz) δ 8.82 - 8.77 (m, 1H), 8.30 - 8.24 (m, 1H), 7.66 - 7.56 (m, 5H), 7.48 (d, J = 7.3 Hz, 1H), 7.46 - 7.42 (m, 2H),
6.44 - 6.24 (m, 1H), 4.75 - 4.69 (m, 1H), 4.66 - 4.60 (m, 1H), 4.23 (d, J = 17.1 Hz, 1H), 3.93 - 3.85 (m, 2H), 3.85 - 3.79 (m, 1H) 6.44 - 6.24 (m, 1H), 4.75 - 4.69 (m, 1H), 4.66 - 4.60 (m, 1H), 4.23 (d, J = 17.1 Hz, 1H), 3.93 - 3.85 (m, 2H), 3.85 - 3.79 (m, 1H)
실시예 36: N-(2-플루오로에틸)-4-(5-(4-플루오로페닐)-5-(트리플루오로메틸)-4,5-다이하이드로아이소옥사졸-3-일)-1-나프트아마이드(N-(2-fluoroethyl)-4-(5-(4-fluorophenyl)-5-(trifluoromethyl)-4,5-dihydroisoxazol-3-yl)-1-naphthamide)Example 36: N-(2-fluoroethyl)-4-(5-(4-fluorophenyl)-5-(trifluoromethyl)-4,5-dihydroisoxazol-3-yl) -1-naphthamide (N-(2-fluoroethyl)-4-(5-(4-fluorophenyl)-5-(trifluoromethyl)-4,5-dihydroisoxazol-3-yl)-1-naphthamide)
1H-NMR (CDCl3, 500Hz) δ 8.82 - 8.76 (m, 1H), 8.29 - 8.25 (m, 1H), 7.65 - 7.58 (m, 4H), 7.57 (d, J = 7.5 Hz, 1H), 7.48 (d, J = 7.3 Hz, 1H), 7.19 - 7.11 (m, 2H), 6.35 (t, J = 5.6 Hz, 1H), 4.74 - 4.69 (m, 1H), 4.65 - 4.60 (m, 1H), 4.23 (d, J = 17.1 Hz, 1H), 3.93 - 3.86 (m, 2H), 3.85 - 3.80 (m, 1H)1H-NMR (CDCl3, 500Hz) δ 8.82 - 8.76 (m, 1H), 8.29 - 8.25 (m, 1H), 7.65 - 7.58 (m, 4H), 7.57 (d, J = 7.5 Hz, 1H), 7.48 ( d, J = 7.3 Hz, 1H), 7.19 - 7.11 (m, 2H), 6.35 (t, J = 5.6 Hz, 1H), 4.74 - 4.69 (m, 1H), 4.65 - 4.60 (m, 1H), 4.23 (d, J = 17.1 Hz, 1H), 3.93 - 3.86 (m, 2H), 3.85 - 3.80 (m, 1H)
실시예 37: 4-(5-(3,5-다이클로로-4-플루오로페닐)-5-(트리플루오로메틸)-4,5-다이하이드로아이소옥사졸-3-일)-N-(2-플루오로에틸)-1-나프트아마이드(4-(5-(3,5-dichloro-4-fluorophenyl)-5-(trifluoromethyl)-4,5-dihydroisoxazol-3-yl)-N-(2-fluoroethyl)-1-naphthamide)Example 37: 4-(5-(3,5-dichloro-4-fluorophenyl)-5-(trifluoromethyl)-4,5-dihydroisoxazol-3-yl)-N- (2-Fluoroethyl)-1-naphthamide (4-(5-(3,5-dichloro-4-fluorophenyl)-5-(trifluoromethyl)-4,5-dihydroisoxazol-3-yl)-N- (2-fluoroethyl)-1-naphthamide)
1H-NMR (CDCl3, 500Hz) δ 8.83 - 8.78 (m, 1H), 8.28 (dt, J = 7.9, 1.1 Hz, 1H), 7.68 - 7.56 (m, 5H), 7.49 (dd, J = 7.5, 1.7 Hz, 1H), 6.33 (t, J = 5.6 Hz, 1H), 4.72 (t, J = 4.7 Hz, 1H), 4.63 (t, J = 4.8 Hz, 1H), 4.25 (d, J = 17.1 Hz, 1H), 3.93 - 3.86 (m, 2H), 3.86 - 3.81 (m, 1H)1H-NMR (CDCl3, 500Hz) δ 8.83 - 8.78 (m, 1H), 8.28 (dt, J = 7.9, 1.1 Hz, 1H), 7.68 - 7.56 (m, 5H), 7.49 (dd, J = 7.5, 1.7 Hz, 1H), 6.33 (t, J = 5.6 Hz, 1H), 4.72 (t, J = 4.7 Hz, 1H), 4.63 (t, J = 4.8 Hz, 1H), 4.25 (d, J = 17.1 Hz, 1H), 3.93 - 3.86 (m, 2H), 3.86 - 3.81 (m, 1H)
실시예 38: 4-(5-(3,5-다이플루오로페닐)-5-(트리플루오로메틸)-4,5-다이하이드로아이소옥사졸-3-일)-N-(2-플루오로에틸)-1-나프트아마이드(4-(5-(3,5-difluorophenyl)-5-(trifluoromethyl)-4,5-dihydroisoxazol-3-yl)-N-(2-fluoroethyl)-1-naphthamide)Example 38: 4-(5-(3,5-difluorophenyl)-5-(trifluoromethyl)-4,5-dihydroisoxazol-3-yl)-N-(2-fluo Roethyl)-1-naphtamide (4-(5-(3,5-difluorophenyl)-5-(trifluoromethyl)-4,5-dihydroisoxazol-3-yl)-N-(2-fluoroethyl)-1- naphthamide)
1H-NMR (CDCl3, 500Hz) δ 8.83 - 8.78 (m, 1H), 8.30 - 8.25 (m, 1H), 7.67 - 7.59 (m, 2H), 7.57 (d, J = 7.5 Hz, 1H), 7.48 (d, J = 7.3 Hz, 1H), 7.20 (dt, J = 6.9, 2.1 Hz, 2H), 6.89 (tt, J = 8.7, 2.4 Hz, 1H), 6.35 (t, J = 5.6 Hz, 1H), 4.72 (dd, J = 5.2, 4.3 Hz, 1H), 4.62 (dd, J = 5.3, 4.3 Hz, 1H), 4.24 (d, J = 17.1 Hz, 1H), 3.91 - 3.85 (m, 2H), 3.85 - 3.80 (m, 1H)1H-NMR (CDCl3, 500Hz) δ 8.83 - 8.78 (m, 1H), 8.30 - 8.25 (m, 1H), 7.67 - 7.59 (m, 2H), 7.57 (d, J = 7.5 Hz, 1H), 7.48 ( d, J = 7.3 Hz, 1H), 7.20 (dt, J = 6.9, 2.1 Hz, 2H), 6.89 (tt, J = 8.7, 2.4 Hz, 1H), 6.35 (t, J = 5.6 Hz, 1H), 4.72 (dd, J = 5.2, 4.3 Hz, 1H), 4.62 (dd, J = 5.3, 4.3 Hz, 1H), 4.24 (d, J = 17.1 Hz, 1H), 3.91 - 3.85 (m, 2H), 3.85 - 3.80 (m, 1H)
실시예 39: 4-(5-(3-클로로-5-(트리플루오로메틸)페닐)-5-(트리플루오로메틸)-4,5-다이하이드로아이소옥사졸-3-일)-N-(2-플루오로에틸)-1-나프트아마이드(4-(5-(3-chloro-5-(trifluoromethyl)phenyl)-5-(trifluoromethyl)-4,5-dihydroisoxazol-3-yl)-N-(2-fluoroethyl)-1-naphthamide)Example 39: 4-(5-(3-chloro-5-(trifluoromethyl)phenyl)-5-(trifluoromethyl)-4,5-dihydroisoxazol-3-yl)-N -(2-Fluoroethyl)-1-naphtamide (4-(5-(3-chloro-5-(trifluoromethyl)phenyl)-5-(trifluoromethyl)-4,5-dihydroisoxazol-3-yl)- N-(2-fluoroethyl)-1-naphthamide)
1H-NMR (CDCl3, 500Hz) δ 8.84 - 8.79 (m, 1H), 8.30 - 8.25 (m, 1H), 7.85 (s, 1H), 7.79 (s, 1H), 7.70 (s, 1H), 7.68 - 7.60 (m, 2H), 7.58 (d, J = 7.3 Hz, 1H), 7.49 (d, J = 7.5 Hz, 1H), 6.34 (t, J = 5.8 Hz, 1H), 4.74 - 4.70 (m, 1H), 4.65 - 4.61 (m, 1H), 4.30 (d, J = 17.2 Hz, 1H), 3.94 - 3.86 (m, 2H), 3.86 - 3.80 (m, 1H)1H-NMR (CDCl3, 500Hz) δ 8.84 - 8.79 (m, 1H), 8.30 - 8.25 (m, 1H), 7.85 (s, 1H), 7.79 (s, 1H), 7.70 (s, 1H), 7.68 - 7.60 (m, 2H), 7.58 (d, J = 7.3 Hz, 1H), 7.49 (d, J = 7.5 Hz, 1H), 6.34 (t, J = 5.8 Hz, 1H), 4.74 - 4.70 (m, 1H) ), 4.65 - 4.61 (m, 1H), 4.30 (d, J = 17.2 Hz, 1H), 3.94 - 3.86 (m, 2H), 3.86 - 3.80 (m, 1H)
실시예 40: N-((1-(클로로메틸)사이클로뷰틸)메틸)-4-(5-(3,5-다이클로로페닐)-5-(트리플루오로메틸)-4,5-다이하이드로아이소옥사졸-3-일)-1-나프트아마이드(N-((1-(chloromethyl)cyclobutyl)methyl)-4-(5-(3,5-dichlorophenyl)-5-(trifluoromethyl)-4,5-dihydroisoxazol-3-yl)-1-naphthamide)Example 40: N-((1-(chloromethyl)cyclobutyl)methyl)-4-(5-(3,5-dichlorophenyl)-5-(trifluoromethyl)-4,5-dihydro Isoxazol-3-yl)-1-naphtamide (N-((1-(chloromethyl)cyclobutyl)methyl)-4-(5-(3,5-dichlorophenyl)-5-(trifluoromethyl)-4, 5-dihydroisoxazol-3-yl)-1-naphthamide)
1H NMR (500 MHz, CDCl3) δ 8.82 (dd, J = 8.4, 1.4 Hz, 1H), 8.33 - 8.24 (m, 1H), 7.65 (dddd, J = 18.2, 8.1, 6.8, 1.4 Hz, 2H), 7.58 - 7.55 (m, 3H), 7.51 (d, J = 7.3 Hz, 1H), 7.46 (t, J = 1.9 Hz, 1H), 6.19 (t, J = 6.4 Hz, 1H), 4.26 (d, J = 17.2 Hz, 1H), 3.89 (d, J = 17.2 Hz, 1H), 3.80 (d, J = 6.3 Hz, 2H), 3.70 (s, 2H), 2.11 - 1.91 (m, 6H)1H NMR (500 MHz, CDCl3) δ 8.82 (dd, J = 8.4, 1.4 Hz, 1H), 8.33 - 8.24 (m, 1H), 7.65 (dddd, J = 18.2, 8.1, 6.8, 1.4 Hz, 2H), 7.58 - 7.55 (m, 3H), 7.51 (d, J = 7.3 Hz, 1H), 7.46 (t, J = 1.9 Hz, 1H), 6.19 (t, J = 6.4 Hz, 1H), 4.26 (d, J = 17.2 Hz, 1H), 3.89 (d, J = 17.2 Hz, 1H), 3.80 (d, J = 6.3 Hz, 2H), 3.70 (s, 2H), 2.11 - 1.91 (m, 6H)
실시예 41: N-(2,5-다이클로로펜틸)-4-(5-(3,5-다이클로로페닐)-5-(트리플루오로메틸)-4,5-다이하이드로아이소옥사졸-3-일)-1-나프트아마이드(N-(2,5-dichloropentyl)-4-(5-(3,5-dichlorophenyl)-5-(trifluoromethyl)-4,5-dihydroisoxazol-3-yl)-1-naphthamide)Example 41: N-(2,5-dichloropentyl)-4-(5-(3,5-dichlorophenyl)-5-(trifluoromethyl)-4,5-dihydroisoxazole- 3-yl)-1-naphtamide (N-(2,5-dichloropentyl)-4-(5-(3,5-dichlorophenyl)-5-(trifluoromethyl)-4,5-dihydroisoxazol-3-yl) -1-naphthamide)
1H NMR (300 MHz, CDCl3) δ 8.87-8.82 (m, 1H), 8.34-8.29 (m, 1H), 7.71-7.60 (m, 3H), 7.58-7.51 (m, 3H), 7.46 (t, J = 1.9Hz, 1H), 6.43 (t, J = 6.1Hz, 1H), 4.31-4.22 (m, 2H), 4.14-4.04 (m, 1H), 3.90 (d, J = 17.2Hz, 1H), 3.67-3.60 (m, 3H), 2.19-1.90 (m, 4H) 1H NMR (300 MHz, CDCl 3 ) δ 8.87-8.82 (m, 1H), 8.34-8.29 (m, 1H), 7.71-7.60 (m, 3H), 7.58-7.51 (m, 3H), 7.46 (t , J = 1.9Hz, 1H), 6.43 (t, J = 6.1Hz, 1H), 4.31-4.22 (m, 2H), 4.14-4.04 (m, 1H), 3.90 (d, J = 17.2Hz, 1H) , 3.67-3.60 (m, 3H), 2.19-1.90 (m, 4H)
실시예 42: N-(3-클로로프로필)-4-(5-(3,5-다이클로로페닐)-5-(트리플루오로메틸)-4,5-다이하이드로아이소옥사졸-3-일)-1-나프트아마이드(N-(3-chloropropyl)-4-(5-(3,5-dichlorophenyl)-5-(trifluoromethyl)-4,5-dihydroisoxazol-3-yl)-1-naphthamide)Example 42: N-(3-chloropropyl)-4-(5-(3,5-dichlorophenyl)-5-(trifluoromethyl)-4,5-dihydroisoxazol-3-yl )-1-naphthamide (N-(3-chloropropyl)-4-(5-(3,5-dichlorophenyl)-5-(trifluoromethyl)-4,5-dihydroisoxazol-3-yl)-1-naphthamide)
1H NMR (300 MHz, CDCl3) δ 8.85-8.82 (m, 1 H), 8.30-8.26 (m, 1 H), 7.71-7.61 (m, 2 H), 7.59-7.56 (m, 3 H), 7.52-7.49 (m, 1 H), 7.46-7.45 (m, 1 H), 6.19 (t, J = 6.3 Hz, 1 H), 4.27 (d, J = 17.2 Hz, 1 H), 3.90 (d, J = 17.2 Hz, 1 H), 3.72 (q, J = 6.0 Hz, 4 H), 2.21 (quint, J = 6.6 Hz, 2 H)1H NMR (300 MHz, CDCl3) δ 8.85-8.82 (m, 1 H), 8.30-8.26 (m, 1 H), 7.71-7.61 (m, 2 H), 7.59-7.56 (m, 3 H), 7.52 -7.49 (m, 1 H), 7.46-7.45 (m, 1 H), 6.19 (t, J = 6.3 Hz, 1 H), 4.27 (d, J = 17.2 Hz, 1 H), 3.90 (d, J = 17.2 Hz, 1 H), 3.72 (q, J = 6.0 Hz, 4 H), 2.21 (quint, J = 6.6 Hz, 2 H)
실시예 43: N-(4-클로로뷰틸)-4-(5-(3,5-다이클로로페닐)-5-(트리플루오로메틸)-4,5-다이하이드로아이소옥사졸-3-일)-1-나프트아마이드(N-(4-chlorobutyl)-4-(5-(3,5-dichlorophenyl)-5-(trifluoromethyl)-4,5-dihydroisoxazol-3-yl)-1-naphthamide)Example 43: N-(4-chlorobutyl)-4-(5-(3,5-dichlorophenyl)-5-(trifluoromethyl)-4,5-dihydroisoxazol-3-yl )-1-naphthamide (N-(4-chlorobutyl)-4-(5-(3,5-dichlorophenyl)-5-(trifluoromethyl)-4,5-dihydroisoxazol-3-yl)-1-naphthamide)
1H NMR (300 MHz, CDCl3) δ 8.84-8.81 (m, 1 H), 8.29-8.26 (m, 1 H), 7.70-7.45 (m, 7 H), 6.03 (t, J = 6.0 Hz, 1 H), 4.26 (d, J = 17.1 Hz, 1 H), 3.89 (d, J = 17.4 Hz, 1 H), 3.66-3.57 (m, 4 H), 1.96-1.83 (m, 4 H)1H NMR (300 MHz, CDCl3) δ 8.84-8.81 (m, 1 H), 8.29-8.26 (m, 1 H), 7.70-7.45 (m, 7 H), 6.03 (t, J = 6.0 Hz, 1 H) ), 4.26 (d, J = 17.1 Hz, 1 H), 3.89 (d, J = 17.4 Hz, 1 H), 3.66-3.57 (m, 4 H), 1.96-1.83 (m, 4 H)
<< 실험예Experiment example 1> 살충활성 분석 1> Insecticidal activity analysis
1. One. 배추좀나방cabbage moth 살충활성 시험- Insecticidal activity test- 엽침지법Leaf steeping method
배추좀나방(Plutella xylostella)은 2000년에 경주 인근에서 채집 후 사육실에서 누대 사육한 개체를 사용하였다. 양배추(다이야)의 잎을 직경 5.8 ㎝의 절편으로 만든 후, 실시예의 화합물(0.1 ppm)을 포함하는 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 48시간 후 배추좀나방의 생충수를 조사하였다. 방제가는 하기 수학식 1 및 수학식 2와 같이 처리 전 밀도를 기초로 처리 후 밀도를 보정하고 이를 다시 무처리에 대한 보정 사충률로써 환산하여 표시하였다(참고 문헌: A method of computing the effectiveness of an insecticide. J. Econ. Entomol. 18:265~267. Abbott, 1925).Cabbage moth (Plutella xylostella) used individuals collected near Gyeongju in 2000 and reared in a breeding room for several generations. Cabbage (Daiya) leaves were cut into pieces with a diameter of 5.8 cm, then immersed in a 5% acetone solution diluted with a drug containing the compound of the example (0.1 ppm) for 30 seconds and thoroughly dried in the shade. Shade-dried cabbage leaves were placed on a petri dish (8.8 cm in diameter) lined with filter paper and inoculated with third instars of diamondback moths three times, 10 each. It was stored under light conditions of 16:8 hours, 25 ± 1 °C, and relative humidity of 50 to 60%, and the live number of diamondback moths was examined 48 hours after inoculation. The control agent corrected the density after treatment based on the density before treatment as shown in Equation 1 and Equation 2 below, and converted it into the corrected mortality rate for untreated. (Reference: A method of computing the effectiveness of an insecticide. Econ. 18:265-267.
그 결과, 실시예 1, 7, 9, 10, 12, 23, 24, 29, 30, 39 화합물을 이용한 시험에서 80% 이상의 사충률을 나타냈다.As a result, tests using the compounds of Examples 1, 7, 9, 10, 12, 23, 24, 29, 30, and 39 showed a mortality rate of more than 80%.
한편, 대조군으로 사용한 기존에 살충제로 사용되고 있는 하기 화학식 2의 화합물(Fluxametamide)(0.1 ppm)은 동일한 조건에서 2일 후 80% 이상의 사충률을 나타냈다.Meanwhile, the compound of the following formula (Fluxametamide) (0.1 ppm), which is previously used as an insecticide, used as a control showed a mortality rate of more than 80% after 2 days under the same conditions.
[화학식 2][Formula 2]
[수학식 1][Equation 1]
방제가(사충률)(%) = (무처리 생충률 - 처리구 생충률) / 무처리 생충률 x 100Control price (mortality rate) (%) = (non-treatment mortality rate - treatment survival rate) / untreated mortality rate x 100
[수학식 2][Equation 2]
생충률 = (처리 후 밀도 / 처리 전 밀도) x 100Viability rate = (density after treatment / density before treatment) x 100
2. 꽃노랑총채벌레 살충활성 시험-분무법2. Insecticidal activity test against yellow flower thrips - spray method
꽃노랑총채벌레(Frankliniella occidentalis)는 생물이용연구소(안동)으로부터 구입한 개체를 사용하였다. 직경 9.0 cm, 높이 4.0 cm의 Insect Breeding Dish(랩가이드®)에 물에 젖은 Filter paper(직경9.0 cm)를 넣고 Parafilm(가로 4.0 cm x 세로 4.0 cm)을 올려주었다. 약제처리 전 4호붓을 이용하여 꽃노랑총채벌레 성충을 패트리디쉬 당 10마리씩 접종하였다. 실시예 화합물(5 ppm)을 포함하는 약제가 희석된 용액 (증류수 + 아세톤 50,000 mg/L + Triton x-100 100 mg/L)을 100 mL 소형분무기에 담고 거리 30 cm, 높이 50 cm의 거리에서 10회 내지 12회 분무처리한 후 기주인 대두콩 떡잎을 1장씩 넣어주었다. 광조건 16:8시간, 25±1℃, 상대습도 50~60% 조건하에서 보관하였으며, 접종 48시간 후 꽃노랑총채벌레 생충수를 조사하였다. 개체의 방제가는 처리 전 밀도를 기초로 처리 후 밀도를 보정하고 이를 다시 무처리에 대한 보정 사충률로써 환산하여 표시하였다.Yellow thrips ( Frankliniella) occidentalis ) was purchased from the BioUtilization Research Institute (Andong). A water-wet filter paper (9.0 cm in diameter) was placed in an Insect Breeding Dish (Lab Guide ® ) with a diameter of 9.0 cm and a height of 4.0 cm, and Parafilm (width 4.0 cm x height 4.0 cm) was placed on it. Before chemical treatment, 10 adult yellow flower thrips were inoculated per petri dish using a No. 4 brush. A diluted solution containing the example compound (5 ppm) (distilled water + acetone 50,000 mg/L + Triton After spraying 10 to 12 times, soybean cotyledons, the host, were added one at a time. It was stored under light conditions of 16:8 hours, 25 ± 1°C, and relative humidity of 50 to 60%, and the number of live flower thrips was examined 48 hours after inoculation. The control value of the individual was calculated by correcting the density after treatment based on the density before treatment and converting this into the corrected mortality rate for untreated.
그 결과, 실시예 10, 23, 39 화합물을 이용한 시험에서 80% 이상의 사충률을 나타냈다.As a result, tests using the compounds of Examples 10, 23, and 39 showed a mortality rate of more than 80%.
한편, 대조군으로 사용한 화학식 2의 화합물(5 ppm)은 동일한 조건에서 2일 후 20% 이하의 사충률을 나타냈다.Meanwhile, the compound of Formula 2 (5 ppm) used as a control showed a mortality rate of less than 20% after 2 days under the same conditions.
3. 3. 담배거세미나방Tobacco cutworm moth 살충활성 시험- Insecticidal activity test- 엽침지법Leaf steeping method
담배거세미나방(Spodoptera litura)은 생물이용연구소(안동)으로부터 구입한 개체를 사용하였다. 양배추(다이야)의 잎을 직경 5.8 ㎝의 절편으로 만든 후, 실시예 화합물(0.1 ppm)을 포함하는 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 48시간 후 담배거세미나방의 생충수를 조사하였다. 개체의 방제가는 처리 전 밀도를 기초로 처리 후 밀도를 보정하고 이를 다시 무처리에 대한 보정 사충률로써 환산하여 표시하였다Tobacco cutworm ( Spodoptera) litura ) used specimens purchased from the BioUtilization Research Institute (Andong). Cabbage (Daiya) leaves were cut into pieces with a diameter of 5.8 cm, then immersed in a 5% acetone solution diluted with a drug containing the example compound (0.1 ppm) for 30 seconds and thoroughly dried in the shade. Shade-dried cabbage leaves were placed in Petri dishes (8.8 cm in diameter) lined with filter paper and inoculated with second instars of Tobacco cutworm moths three times with 10 each. It was stored under light conditions of 16:8 hours, 25 ± 1°C, and relative humidity of 50 to 60%, and the live number of tobacco cutworms was examined 48 hours after inoculation. The control value of the individual was calculated by correcting the density after treatment based on the density before treatment and converting this into the corrected mortality rate for untreated.
그 결과, 실시예 10, 12, 39 화합물을 이용한 시험에서 80% 이상의 사충률을 나타냈다.As a result, tests using the compounds of Examples 10, 12, and 39 showed a mortality rate of more than 80%.
한편, 대조군으로 사용한 화학식 2의 화합물(0.1 ppm)은 동일한 조건에서 2일 후 80% 이상의 사충률을 나타냈다.Meanwhile, the compound of Formula 2 (0.1 ppm) used as a control showed a mortality rate of more than 80% after 2 days under the same conditions.
4. 4. 열대거세미나방Tropical cutworm moth 살충활성 시험- Insecticidal activity test- 엽침지법Leaf steeping method
열대거세미나방은 충남대학교으로부터 분양받은 개체를 실내 누대사육하여 시험에 사용하였다(2021년). 양배추(다이야)의 잎을 직경 5.8 ㎝의 절편으로 만든 후, 상기 실시예의 화합물(1 ppm)을 포함하는 약제가 희석된 용액 (증류수 + 아세톤 50,000 mg/L + Triton x-100 100 mg/L)에 30초간 침지한 후 충분히 음건하였다. 음건한 양배추 잎은 종이필터가 깔린 패트리디쉬 (직경 8.8 ㎝)에 놓고 열대거세미나방 2~3령충을 10마리씩 3회 내지 5회 반복 접종하였다. 광조건 16:8시간, 25±1 ℃, 상대습도 50% 내지 60% 조건하에서 보관하였으며, 접종 24시간 후 열대거세미나방 유충의 생충수를 조사하였다. 방제가는 처리 전 밀도를 기초로 처리 후 밀도를 보정하고 이를 다시 무처리에 대한 보정 사충률로서 환산하여 표시하였다.Tropical cutworm moths were distributed indoors from Chungnam National University and used for testing (2021). Cabbage (Daiya) leaves were cut into pieces with a diameter of 5.8 cm, and then a solution containing a drug containing the compound (1 ppm) of the above example was diluted (distilled water + acetone 50,000 mg/L + Triton x-100 100 mg/L). After being immersed in for 30 seconds, it was sufficiently shaded. Shade-dried cabbage leaves were placed in Petri dishes (8.8 cm in diameter) lined with paper filters and inoculated with 2nd to 3rd instars of tropical cutworm moths, 10 each, three to five times. It was stored under light conditions of 16:8 hours, 25±1°C, and relative humidity of 50% to 60%, and the live number of tropical cutworm larvae was examined 24 hours after inoculation. The control value was calculated by correcting the density after treatment based on the density before treatment and converting it into the corrected mortality rate for untreated.
그 결과, 실시예 39 화합물을 이용한 시험에서 80% 이상의 사충률을 나타냈다.As a result, a test using the compound of Example 39 showed a mortality rate of more than 80%.
한편, 대조군으로 사용한 화학식 2의 화합물(1 ppm)은 동일한 조건에서 1일 후 80% 이상의 사충률을 나타냈다.Meanwhile, the compound of Formula 2 (1 ppm) used as a control showed a mortality rate of more than 80% after 1 day under the same conditions.
5. 5. 파방나방moth 살충활성 시험- Insecticidal activity test- 엽침지법Leaf steeping method
파밤나방(Spodoptera exigua)은 생물이용연구소(안동)으로부터 구입한 개체를 사용하였다. 양배추(다이야)의 잎을 직경 5.8 ㎝의 절편으로 만든 후, 상기 실시예의 화합물(1 ppm)을 포함하는 약제가 희석된 용액 (증류수 + 아세톤 50,000 mg/L + Triton x-100 100 mg/L)에 30초간 침지한 후 충분히 음건하였다. 음건한 양배추 잎은 종이필터가 깔린 패트리디쉬 (직경 8.8 ㎝)에 놓고 파밤나방 2~3령충을 10마리씩 3회 내지 5회 반복 접종하였다. 광조건 16:8시간, 25±1℃, 상대습도 50% 내지 60% 조건하에서 보관하였으며, 접종 24시간 후 파밤나방 유충의 생충수를 조사하였다. 방제가는 처리 전 밀도를 기초로 처리 후 밀도를 보정하고 이를 다시 무처리에 대한 보정 사충률로서 환산하여 표시하였다.The green onion moth ( Spodoptera exigua ) was purchased from the BioUtilization Research Institute (Andong). Cabbage (Daiya) leaves were cut into pieces with a diameter of 5.8 cm, and then a solution containing a drug containing the compound (1 ppm) of the above example was diluted (distilled water + acetone 50,000 mg/L + Triton x-100 100 mg/L). After being immersed in for 30 seconds, it was sufficiently shaded. Shade-dried cabbage leaves were placed in Petri dishes (8.8 cm in diameter) lined with paper filters and inoculated with 2nd to 3rd instars of green onion moths, 10 times each, 3 to 5 times. It was stored under light conditions of 16:8 hours, 25 ± 1°C, and relative humidity of 50% to 60%, and the live number of green onion moth larvae was examined 24 hours after inoculation. The control value was calculated by correcting the density after treatment based on the density before treatment and converting it into the corrected mortality rate for untreated.
그 결과, 실시예 39 화합물을 이용한 시험에서 80% 이상의 사충률을 나타냈다.As a result, a test using the compound of Example 39 showed a mortality rate of more than 80%.
한편, 대조군으로 사용한 화학식 2의 화합물(1 ppm)은 동일한 조건에서 2일 후 80% 이상의 사충률을 나타냈다.Meanwhile, the compound of Formula 2 (1 ppm) used as a control showed a mortality rate of more than 80% after 2 days under the same conditions.
6. 6. 콩명나방Kongmyeong moth 살충활성 시험-인공사료 Insecticidal activity test - artificial feed 침지법Soaking method
콩명나방(Maruca vitrta)은 생물이용연구소(안동)으로부터 구입한 개체를 사용하였다. 콩명나방의 인공사료는 아래와 같은 방법으로 조제하였다. Maruca vitrta was purchased from the BioUtilization Research Institute (Andong). Artificial feed for Kongmyeong moth was prepared in the following manner.
(1) 2차 증류수 625 mL에 한천가루(Agar powder) 13 g을 1 L 비커에 넣어 전자레인지에 10분간 돌려 끓여준다.(1) Put 13 g of agar powder in 625 mL of double distilled water in a 1 L beaker and boil in the microwave for 10 minutes.
(2) 끓여놓은 한천을 믹서기에 넣고 콩가루 75 g, 팥가루 20 g, 맥아가루 10 g과 2차 증류수 175 mL을 넣어 섞어준다.(2) Put the boiled agar in a blender and mix with 75 g of soybean powder, 20 g of red bean powder, 10 g of malt powder, and 175 mL of double distilled water.
(3) 혼합물이 50 ℃ 수준으로 식으면 비타민 혼합물(Vitamin mixture) 5 g, 아스코르브산(Ascorbic acid) 4 g, 소르빈산(Sorbic acid) 1 g, β-시토스테롤(β-sitosterol) 1 g, 글루코스(Glucose) 10 g, 셀룰로스(Cellulose) 10 g, 콜레스테롤(Cholesterol) 3 g, 메틸-p-하이드록시벤조네이트(Methyl-p-hydroxybenzoate) 1.5 g, 오레오마이신(Aureomycin) 0.5 g, 퓨미딜-B(Fumidil B) 0.4 g을 넣고 섞어준다.(3) When the mixture cools to 50℃, 5 g of vitamin mixture, 4 g of ascorbic acid, 1 g of sorbic acid, 1 g of β-sitosterol, and glucose ( Glucose 10 g, Cellulose 10 g, Cholesterol 3 g, Methyl-p-hydroxybenzoate 1.5 g, Aureomycin 0.5 g, Fumidyl-B ( Add 0.4 g of Fumidil B) and mix.
(4) 충분히 식힌 후 냉장보관한다.(4) Cool sufficiently and store in the refrigerator.
콩명나방 실내활성평가는 인공사료를 1 ㎝ x 1 ㎝ x 0.5 ㎝의 절편으로 만든 후, 상기 실시예의 화합물(1 ppm)을 포함하는 약제가 희석된 용매 (증류수 + 아세톤 50,000 mg/L + Triton x-100 100 mg/L)에 30초간 침지한 후 알루미늄 호일에 올려 충분히 음건하였다. 음건한 인공사료 절편을 페트리디쉬(Ø90 x 15 mm)에 배치하기 전 습도유지를 위해 증류수를 종이필터(Ø90 mm)에 처리하고 종이필터 위에 파라필름 (5.1 cm x 5.1 cm)을 깔고 그 위에 인공사료 절편을 놓았다. 콩명나방 2~3령충을 10마리씩 3회 내지 5회 반복 접종하였다. 광조건 16:8시간, 25±1 ℃, 상대습도 50% 내지 60% 조건 하에서 보관하였으며, 접종 48시간 후 콩명나방 유충의 생충수를 조사하였다. 방제가는 처리 전 밀도를 기초로 처리 후 밀도를 보정하고 이를 다시 무처리에 대한 보정 사충률로서 환산하여 표시하였다(Abbott, 1925).To evaluate the indoor activity of Kongmyeong moth, the artificial feed was cut into 1 cm -100 mg/L) for 30 seconds, then placed on aluminum foil and sufficiently shaded. Before placing the shaded artificial feed slices in a petri dish (Ø90 The food sections were placed. The inoculation was repeated 3 to 5 times with 10 2nd to 3rd instar larvae. It was stored under light conditions of 16:8 hours, 25±1°C, and relative humidity of 50% to 60%, and the number of live beetle moth larvae was examined 48 hours after inoculation. The control value was calculated by correcting the density after treatment based on the density before treatment and converting it into the corrected mortality rate for untreated (Abbott, 1925).
그 결과, 실시예 39 화합물을 이용한 시험에서 80% 이상의 사충률을 나타냈다.As a result, tests using the compound of Example 39 showed a mortality rate of more than 80%.
한편, 대조군으로 사용한 화학식 2의 화합물(1 ppm)은 동일한 조건에서 2일 후 10% 이하의 사충률을 나타냈다.Meanwhile, the compound of Formula 2 (1 ppm) used as a control showed a mortality rate of less than 10% after 2 days under the same conditions.
상기 시험 결과 중, 실시예 39 화합물 및 대조군 화합물의 시험 결과를 하기 표로서 정리하였다.Among the above test results, the test results of the Example 39 compound and the control compound are summarized in the table below.
<< 실험예Experiment example 2> 꿀벌에 대한 2> About bees 급성섭식독성Acute feeding toxicity 시험 test
꿀벌(Apis mellifera)을 이용한 급성독성을 파악하기 위하여 농촌진흥청고시 제2021-20호 “환경생물독성 시험의 기준과 방법 - 꿀벌에 대한 급성섭식독성시험(2021년 09월 28일)”과 OECD Guideline의 “Honeybees, Acute Oral Toxicity test(No. 213, adopted : 1998. 9. 21)”에 준하여 실시하였다.Bees ( Apis ) mellifera ), the Rural Development Administration Notice No. 2021-20 “Standards and methods for environmental biotoxicity testing - Acute feeding toxicity test on honey bees (September 28, 2021)” and the OECD Guideline’s “Honeybees” , Acute Oral Toxicity test (No. 213, adopted: September 21, 1998)”.
2020년 10월 15일 분양받은 꿀벌을 본 연구소의 꿀벌 사육공간내에서 사육하였으며, 입수 이후 동절기, 장마기간 등 사육담당자의 판단에 의해 필요시 50% 자당용액(w/w)을 급이하였으며, 하절기(3～10월)에는 월 2회 이상 벌집내부를 점검하여 봉군의 건강상태를 확인하고 관리하였다.The honey bees received on October 15, 2020 were raised in the bee breeding space of this research institute, and after acquisition, they were fed with 50% sucrose solution (w/w) when necessary at the discretion of the breeding manager, such as during winter and rainy season. During the summer season (March to October), the interior of the hive was inspected at least twice a month to check and manage the health of the beehives.
꿀벌 사육공간에서에서 약 12개월 정도 사육한 꿀벌을 시험물질 노출 약 4시간 전에 꿀벌실험실의 사육랙으로 옮겨 스텐레스 철망(길이 15 cm, 직경 5 cm)으로 제작된 원통형 시험용기에 각각 10마리씩을 넣고 독성시험과 동일한 환경조건에서 순화시켰다. 시험물질 노출 약 2시간 전부터 절식을 실시하였다. 시험에 필요한 마리수의 110%이상을 시험물질 노출 약 4시간 전에 독성시험과 동일한 환경조건에서 순화시켰다. 군분리를 위한 개체의 선별은 마취통에 꿀벌을 취하여 CO2가스를 이용하여 마취하였다. 순화와 절식기간동안 치사개체 발생 유무, 온도 및 습도를 측정하여 기록하였으며, 관찰시간을 제외하고는 암조건하에서 순화하였다. 온도는 25.0℃이고 습도는 54.0~57.0%이었다. 조제농도는 11 ㎍ a.i./bee로 노출하기 위하여 실시예 39 화합물 50.5 mg에 DMSO(Dimethyl sulfoxide) 0.1 mL를 가하여 용해한 후 Tween80 0.1 mL과 50% 설탕용 액 9.8 m;를 혼합하여 100 ㎍ a.i./bee 용액을 조제한 후, 100 ㎍ a.i./bee 용액 1.1 ml에 50% 설탕용액 8.9 mL를 가하여 11 ㎍ a.i./bee 용액을 조제하였다. 독성시험은 투여약량 기준으로 11 ㎍ a.i./bee 투여군과 용매대조군, 무처치대조군으로 실시하였으며 시험약량 당 30마리의 꿀벌을 노출시켰다. 노출 후 1, 4, 24, 48시간 뒤에 치사개체수와 독성증상을 관찰하였다. 이상의 시험결과로 본 시험물질의 24, 48시간 LD50(Lethal Dose for 50% kill, 반수치사약량)값은 > 11 ㎍ a.i./bee 이었다. 시험기간 동안 용매 대조군 및 무처치 대조군에서 치사개체가 발생하지 않았으며, 특이한 증상도 관찰되지 않았다. 시험기간 동안 처리군에서 치사개체 또는 독성증상이 관찰되지 않았다. 본 발명의 실시예에서 제조된 화합물에 대해 꿀벌에 대한 급성섭식독성 시험한 결과 >11 ㎍/bee(LD50, Honeybee) 으로 측정되었다. 한편, 화학식 2의 대조군 화합물에 대해서도 비교실험 결과, 실시예 39 화합물은 대조군 화합물에 비교할 때 약 14배 이상 안전한 것으로 나타났다.Bees reared in the bee breeding space for about 12 months were transferred to a breeding rack in the bee laboratory about 4 hours before exposure to the test substance, and 10 bees each were placed in a cylindrical test container made of stainless steel wire mesh (15 cm in length, 5 cm in diameter). It was acclimatized under the same environmental conditions as for the toxicity test. Fasting was performed approximately 2 hours before exposure to the test substance. More than 110% of the number of animals required for the test were acclimatized under the same environmental conditions as the toxicity test about 4 hours before exposure to the test substance. To select individuals for group separation, bees were placed in an anesthetic can and anesthetized using CO 2 gas. During the acclimation and fasting period, the occurrence of fatalities, temperature, and humidity were measured and recorded, and acclimatization was conducted under dark conditions except for the observation time. The temperature was 25.0℃ and the humidity was 54.0~57.0%. To expose the prepared concentration to 11 ㎍ ai/bee, 50.5 mg of the compound of Example 39 was dissolved by adding 0.1 mL of DMSO (Dimethyl sulfoxide) and then mixed with 0.1 mL of Tween80 and 9.8 mL of 50% sugar solution to make 100 ㎍ ai/bee. After preparing the solution, 8.9 mL of 50% sugar solution was added to 1.1 ml of 100 ㎍ ai/bee solution to prepare 11 ㎍ ai/bee solution. The toxicity test was conducted with a group administered 11 ㎍ ai/bee, a solvent control group, and an untreated control group based on the administered dose, and 30 bees were exposed to each test dose. The number of fatalities and symptoms of toxicity were observed 1, 4, 24, and 48 hours after exposure. According to the above test results, the LD 50 (Lethal Dose for 50% kill, half-lethal dose) value of this test substance for 24 and 48 hours was > 11 ㎍ ai/bee. During the test period, no fatalities occurred in the solvent control group and the untreated control group, and no unusual symptoms were observed. No deaths or toxicity symptoms were observed in the treatment group during the test period. As a result of an acute feeding toxicity test on honey bees for the compound prepared in an example of the present invention, it was measured to be >11 ㎍/bee (LD 50 , Honeybee). Meanwhile, as a result of comparative experiments with the control compound of Formula 2, the compound of Example 39 was found to be about 14 times safer than the control compound.
이상, 본 발명을 바람직한 실시예 및 실험예를 통해 상세히 설명하였으나, 본 발명의 범위는 특성 실시예에 한정되는 것은 아니며, 첨부된 특허 청구범위에 의하여 해석되어야 할 것이다. 또한, 이 기술분야에서 통상의 지식을 습득한 자라면, 본 발명의 범위에서 벗어나지 않으면서도 많은 수정과 변형이 가능함을 이해하여야 할 것이다.Above, the present invention has been described in detail through preferred embodiments and experimental examples, but the scope of the present invention is not limited to the specific examples and should be interpreted in accordance with the appended patent claims. Additionally, those skilled in the art should understand that many modifications and variations are possible without departing from the scope of the present invention.
Claims (11)
(10) 4-(5-(3-클로로-5-(트리플루오로메틸)페닐)-5-(트리플루오로메틸)-4,5-다이하이드로아이소옥사졸-3-일)-N-(2-클로로에틸)-2-메틸벤즈아마이드;
(18) 4-(5-(3-클로로-5-(트리플루오로메틸)페닐)-5-(트리플루오로메틸)-4,5-다이하이드로아이소옥사졸-3-일)-N-(2-플루오로에틸)-2-메틸벤즈아마이드;
(30) 4-(5-(3-클로로-5-(트리플루오로메틸)페닐)-5-(트리플루오로메틸)-4,5-다이하이드로아이소옥사졸-3-일)-N-(2-클로로에틸)-1-나프트아마이드; 및
(39) 4-(5-(3-클로로-5-(트리플루오로메틸)페닐)-5-(트리플루오로메틸)-4,5-다이하이드로아이소옥사졸-3-일)-N-(2-플루오로에틸)-1-나프트아마이드.
A compound selected from the following group of compounds, a stereoisomer thereof, a hydrate thereof, or a salt thereof:
(10) 4-(5-(3-chloro-5-(trifluoromethyl)phenyl)-5-(trifluoromethyl)-4,5-dihydroisoxazol-3-yl)-N- (2-chloroethyl)-2-methylbenzamide;
(18) 4-(5-(3-chloro-5-(trifluoromethyl)phenyl)-5-(trifluoromethyl)-4,5-dihydroisoxazol-3-yl)-N- (2-fluoroethyl)-2-methylbenzamide;
(30) 4-(5-(3-chloro-5-(trifluoromethyl)phenyl)-5-(trifluoromethyl)-4,5-dihydroisoxazol-3-yl)-N- (2-chloroethyl)-1-naphthamide; and
(39) 4-(5-(3-chloro-5-(trifluoromethyl)phenyl)-5-(trifluoromethyl)-4,5-dihydroisoxazol-3-yl)-N- (2-Fluoroethyl)-1-naphthamide.
[화학식 1]
상기 화학식 1에서,
x는 1 내지 3의 정수이며, R1은 각각 독립적으로 -H, 할로겐, 또는 -C1-5할로알킬이되, 상기 R1은 -C1-5할로알킬을 하나 이상 반드시 포함하며,
R2는 C1-5할로알킬이고;
R3는 , , , , , , , 또는 이고, 이때, 상기 X는 각각 독립적으로 I, Br, Cl, 또는 F이고;
Q는 또는 이고;
R4a 및 R4b는 각각 독립적으로 -H, 할로겐, C1-5알킬, 또는 C1-5할로알킬이다.
A pesticide composition comprising a compound represented by the following formula (1), a stereoisomer thereof, a hydrate thereof, or a salt thereof as an active ingredient:
[Formula 1]
In Formula 1,
x is an integer from 1 to 3, and R 1 is each independently -H, halogen, or -C 1-5 haloalkyl, wherein R 1 necessarily includes at least one -C 1-5 haloalkyl,
R 2 is C 1-5 haloalkyl;
R 3 is , , , , , , , or , wherein the X is each independently I, Br, Cl, or F;
Q is or ego;
R 4a and R 4b are each independently -H, halogen, C 1-5 alkyl, or C 1-5 haloalkyl.
상기 x는 1 내지 3의 정수이며, R1은 각각 독립적으로 -H, 할로겐, 또는 -C1-5할로알킬이되, 상기 R1은 -CF3을 하나 이상 반드시 포함하며,
상기 R2는 -CF3이고;
상기 R3는 , , , 또는 이고,
상기 Q는 또는 이고;
상기 R4a 및 R4b는 각각 독립적으로 -H, 할로겐, 또는 C1-5알킬, 또는 C1-5할로알킬인, 살충제 조성물.
According to paragraph 2,
x is an integer of 1 to 3, and R 1 is each independently -H, halogen, or -C 1-5 haloalkyl, but R 1 must include at least one -CF 3 ,
R 2 is -CF 3 ;
The R 3 is , , , or ego,
The above Q is or ego;
The pesticide composition wherein R 4a and R 4b are each independently -H, halogen, or C 1-5 alkyl, or C 1-5 haloalkyl.
상기 R3는 이고,
상기 Q는 또는 이고;
상기 R4a 및 R4b는 각각 독립적으로 -H, 또는 C1-5알킬인, 살충제 조성물.
According to paragraph 3,
The R 3 is ego,
The above Q is or ego;
The pesticide composition wherein R 4a and R 4b are each independently -H, or C 1-5 alkyl.
상기 화학식 1로 표시되는 화합물은 하기 화합물 군으로부터 선택되는 어느 하나인, 살충제 조성물:
(10) 4-(5-(3-클로로-5-(트리플루오로메틸)페닐)-5-(트리플루오로메틸)-4,5-다이하이드로아이소옥사졸-3-일)-N-(2-클로로에틸)-2-메틸벤즈아마이드;
(18) 4-(5-(3-클로로-5-(트리플루오로메틸)페닐)-5-(트리플루오로메틸)-4,5-다이하이드로아이소옥사졸-3-일)-N-(2-플루오로에틸)-2-메틸벤즈아마이드;
(30) 4-(5-(3-클로로-5-(트리플루오로메틸)페닐)-5-(트리플루오로메틸)-4,5-다이하이드로아이소옥사졸-3-일)-N-(2-클로로에틸)-1-나프트아마이드; 및
(39) 4-(5-(3-클로로-5-(트리플루오로메틸)페닐)-5-(트리플루오로메틸)-4,5-다이하이드로아이소옥사졸-3-일)-N-(2-플루오로에틸)-1-나프트아마이드.
According to paragraph 2,
A pesticide composition in which the compound represented by Formula 1 is any one selected from the group of compounds below:
(10) 4-(5-(3-chloro-5-(trifluoromethyl)phenyl)-5-(trifluoromethyl)-4,5-dihydroisoxazol-3-yl)-N- (2-chloroethyl)-2-methylbenzamide;
(18) 4-(5-(3-chloro-5-(trifluoromethyl)phenyl)-5-(trifluoromethyl)-4,5-dihydroisoxazol-3-yl)-N- (2-fluoroethyl)-2-methylbenzamide;
(30) 4-(5-(3-chloro-5-(trifluoromethyl)phenyl)-5-(trifluoromethyl)-4,5-dihydroisoxazol-3-yl)-N- (2-chloroethyl)-1-naphthamide; and
(39) 4-(5-(3-chloro-5-(trifluoromethyl)phenyl)-5-(trifluoromethyl)-4,5-dihydroisoxazol-3-yl)-N- (2-Fluoroethyl)-1-naphthamide.
상기 조성물은 총채벌레목 또는 나방목 해충의 방제용인, 살충제 조성물.
According to paragraph 2,
The composition is an insecticidal composition for controlling thrips or lepidopteran pests.
상기 조성물은 꽃노랑총채벌레(Frankliniella occidentalis), 담배총채벌레(F. tenuicornis), 대만총채벌레(F. intonsa), 백합총채벌레(F. lilivora), 오이총채벌레(Thrips palmi Karny), 파총채벌레(Thrips tabaci Lindeman), 배추좀나방(Plutella xylostella), 담배거세미나방(Spodoptera litura), 열대거세미나방(Spodoptera frugiperda), 파밤나방(Spodoptera exigua), 또는 콩명나방(Maruca vitrta)의 방제용인, 살충제 조성물.
According to paragraph 2,
The composition includes yellow flower thrips ( Frankliniella occidentalis ), tobacco thrips ( F. tenuicornis ), Taiwanese thrips ( F. intonsa ), lily thrips ( F. lilivora ), cucumber thrips ( Thrips palmi Karny ), and green onion thrips. For the control of insects ( Thrips tabaci Lindeman ), cabbage moths ( Plutella xylostella ), tobacco cutworms ( Spodoptera litura ), tropical cutworms ( Spodoptera frugiperda ), green onion moths ( Spodoptera exigua ), or beetroot moths ( Maruca vitrta ). , pesticide composition.
A method for controlling pests comprising treating crops or their habitat with the pesticide composition according to claim 2.
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Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2008154528A2 (en) * | 2007-06-13 | 2008-12-18 | E. I. Du Pont De Nemours And Company | Isoxazoline insecticides |
| WO2011157733A2 (en) * | 2010-06-18 | 2011-12-22 | Novartis Ag | New use |
| KR101597838B1 (en) | 2007-06-26 | 2016-02-25 | 이 아이 듀폰 디 네모아 앤드 캄파니 | Naphthalene isoxazoline invertebrate pest control agents |
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| Publication number | Priority date | Publication date | Assignee | Title |
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| DK1731512T3 (en) * | 2004-03-05 | 2015-01-05 | Nissan Chemical Ind Ltd | Isoxazoline-substituted benzamide AND INSTRUMENTS FOR COMBATING HARMFUL ORGANISMS |
| TWI556741B (en) * | 2007-08-17 | 2016-11-11 | 英特威特國際股份有限公司 | Isoxazoline compositions and their use as antiparasitics |
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Patent Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2008154528A2 (en) * | 2007-06-13 | 2008-12-18 | E. I. Du Pont De Nemours And Company | Isoxazoline insecticides |
| KR101597838B1 (en) | 2007-06-26 | 2016-02-25 | 이 아이 듀폰 디 네모아 앤드 캄파니 | Naphthalene isoxazoline invertebrate pest control agents |
| WO2011157733A2 (en) * | 2010-06-18 | 2011-12-22 | Novartis Ag | New use |
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