KR880001572B1 - Pyrazoline derivatives and the manufacturing process thereof - Google Patents

Pyrazoline derivatives and the manufacturing process thereof Download PDF

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KR880001572B1
KR880001572B1 KR1019870010787A KR870010787A KR880001572B1 KR 880001572 B1 KR880001572 B1 KR 880001572B1 KR 1019870010787 A KR1019870010787 A KR 1019870010787A KR 870010787 A KR870010787 A KR 870010787A KR 880001572 B1 KR880001572 B1 KR 880001572B1
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carboxamide
pyrazoline
dihydro
chlorophenyl
benzodioxol
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KR1019870010787A
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Korean (ko)
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조이 더갠 앤겔리나
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에프 엠씨 코포레이션
챠알스 씨. 펠로우스
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Priority claimed from KR1019850007838A external-priority patent/KR880001568B1/en
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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D231/00—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings
    • C07D231/02—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings
    • C07D231/06—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member

Abstract

Compounds (I-5), pirazolin derivatives, are prepared by alkylation of the reaction product of compound (II) and (III). In formular, RA is 1,3-benzodioxol-5-yl; RB is mono-substituted phenyl; RC is 2,3- dihydro-2,2-dimethylbenzofuran-5-yl, 2, 3dihydrobenzofuran-5-yl, 2,3- dihydro-2,2,3,3-tetrafluorobenzofuran5-yl, 1,4-benzodioxane-5-yl, 1,4-benzodioxane-6-yl, 2, 2difluorobenzodioxol-5-yl, 2,2- dimethylbenzodioxol-5-yl, 2,2-dimethylbenzodioxol-5-yl, 2,2-indan-5- yl, croman-6-yl, 2,2demethylcroman-6-yl, 2,2,3-trifluoro-1,4- benzodioxane-5-yl or 3-chloro-2,2,3-trifluoro-1,4-benzodioxane-5-yl; RN is hydrogen or methyl; W is oxygen or sulfur.

Description

피라졸린 유도체 및 그의 제조방법Pyrazoline derivatives and preparation method thereof

본 발명은 탁월한 살충 활성을 갖는 다음 일반식(Ｉ)의 신규 피라졸린 유도체 및 그의 제조방법에 관한 것이다.The present invention relates to novel pyrazoline derivatives of the following general formula (I) having excellent pesticidal activity and methods for their preparation.

Figure kpo00001
Figure kpo00001

상기식에서In the above formula

RA는 일반식

Figure kpo00002
또는 일반식
Figure kpo00003
의 그룹이고, 여기에서
Figure kpo00004
는 수소, 할로겐, 저급 알킬 저급 알콕시, 저급 알로알콕시, 저급 알키닐옥시 및 저급 할로알킬 중에서 선택되며, X는 일반식
Figure kpo00005
(여기에서, a는 1 내지 3이고, a'는 0 또는 1이며, a+a'는 적어도 2이지만 3보다 크지는 않고,
Figure kpo00006
및
Figure kpo00007
는 각기 독립적으로 수소, 할로겐 및 저급 알킬 중에서 선택된다)의 브리지(bridge)이고,
Figure kpo00008
는 수소, 할로겐, 저급 알킬, 저급 알콕시, 저급 할로알콕시 및 저급 할로알킬 중에서 선택되며 : RB는 일반식
Figure kpo00009
또는
Figure kpo00010
의 4- 또는 5-치환체이며, 여기에서
Figure kpo00011
는 수소, 할로겐, 저급 알킬, 저급 알콕시 및 저급 할로알킬중에서 선택되고, Y는 일반식
Figure kpo00012
(여기에서, b는 1 내지 3이고, b'는 0 또는 1이며, b+b'는 적어도 2이지만 3보다 크지는 않고,
Figure kpo00013
및
Figure kpo00014
는 각각 독립적으로 수소, 할로겐 및 저급 알킬중에서 선택된다)의 브리지이며,
Figure kpo00015
는 수소, 할로겐, 저급 알킬, 저급 알콕시, 저급 할로알콕시 및 저급 할로알킬 중에서 선택되고 ;R A is a general formula
Figure kpo00002
Or general formula
Figure kpo00003
Is a group of
Figure kpo00004
Is selected from hydrogen, halogen, lower alkyl lower alkoxy, lower alloalkoxy, lower alkynyloxy and lower haloalkyl, and X is a general formula
Figure kpo00005
(Wherein a is 1 to 3, a 'is 0 or 1, a + a' is at least 2 but not greater than 3,
Figure kpo00006
And
Figure kpo00007
Are each independently a bridge of hydrogen, halogen and lower alkyl),
Figure kpo00008
Is selected from hydrogen, halogen, lower alkyl, lower alkoxy, lower haloalkoxy and lower haloalkyl: R B is a general formula
Figure kpo00009
or
Figure kpo00010
Of 4- or 5-substituents, wherein
Figure kpo00011
Is selected from hydrogen, halogen, lower alkyl, lower alkoxy and lower haloalkyl, and Y is a general formula
Figure kpo00012
(Where b is 1 to 3, b 'is 0 or 1, b + b' is at least 2 but not greater than 3,
Figure kpo00013
And
Figure kpo00014
Are each independently a bridge of hydrogen, halogen and lower alkyl),
Figure kpo00015
Is selected from hydrogen, halogen, lower alkyl, lower alkoxy, lower haloalkoxy and lower haloalkyl;

RC는 일반식

Figure kpo00016
또는
Figure kpo00017
의 그룹이고, 여기에서 RD는 수소 및 저급 알킬중에서 선택되며, RE는 할로겐, 저급 알킬, 저급 알콕시, 저급 할로알콕시, 저급 할로알킬, 시아노, 니트로, -NRFRG(여기에서, RF및 RG는 각각 독립적으로 저급 알킬이다) 및 -SOnRH(여기에서, RH는 저급 알 킬이고, n은 0 내지 2이다)중에서 선택되고, Z는 일반식
Figure kpo00018
(여기에서, c는 1 내지 3이고, c'는 0 또는 1이고, c+c는 적어도 2이지만 3보다 크지는 않고,
Figure kpo00019
및
Figure kpo00020
는 독립적으로 수소, 할로겐 및 저급 알킬중에서 선택되는데, 단 c가 1이고 c'가 1이면
Figure kpo00021
및
Figure kpo00022
는 둘다 수소가 아니다)의 브리지이며,
Figure kpo00023
는 수소, 할로겐, 저급 알킬, 저급 알콕시, 저급 할로알콕시 및 저급 할로알킬 중에서 선택되고 ;R C is a general formula
Figure kpo00016
or
Figure kpo00017
Wherein R D is selected from hydrogen and lower alkyl, R E is halogen, lower alkyl, lower alkoxy, lower haloalkoxy, lower haloalkyl, cyano, nitro, -NR F R G (wherein R F and R G is selected from respectively independently a lower alkyl) and -SO n R H (here, R H is a lower alkenyl Kiel, n is 0 to 2), Z is represented by the general formula
Figure kpo00018
(Wherein c is 1 to 3, c 'is 0 or 1, c + c is at least 2 but not greater than 3,
Figure kpo00019
And
Figure kpo00020
Is independently selected from hydrogen, halogen and lower alkyl, provided that c is 1 and c 'is 1
Figure kpo00021
And
Figure kpo00022
Is both a bridge of hydrogen)
Figure kpo00023
Is selected from hydrogen, halogen, lower alkyl, lower alkoxy, lower haloalkoxy and lower haloalkyl;

RN은 수소 또는 저급 알킬이고 ;R N is hydrogen or lower alkyl;

V 및 W는 독립적으로 산소 또는 황이다.V and W are independently oxygen or sulfur.

본 발명은 또한 생체에 영향을 미치는 화학 조성물의 분야에 관한 것으로, 더 상세히 말하면 신규의 피라졸린 살충제, 이의 제조방법, 이에 대한 중간체, 피라졸린을 함유하는 살충제 조성물 및 해충을 구제하기 위한 피라졸린의 용도에 관한 것이다.The present invention also relates to the field of chemical compositions affecting the living body, and more particularly, to novel pyrazoline insecticides, methods for their preparation, intermediates thereof, pesticide compositions containing pyrazoline and pyrazoline for controlling pests. It is about a use.

피라졸린은 다음 구조식을 갖는 5-원 헤테로 사이클릭환 화합물이며, 환원자는 다음과 같이 번호를 매긴다 :Pyrazoline is a 5-membered heterocyclic ring compound having the following structural formula, and the reducers are numbered as follows:

Figure kpo00024
Figure kpo00024

상출제 분야에서 특정 1-카바모일 피라졸린 유도체가 살충제라는 사실이 공지되어 있다. 예를 들면, 미합중국 특허 제4,174,393호에는 피라졸린 환의 3과 4위치에 페닐 치환체를 갖는 1-카바모일 피라졸린의 살충 활성 또한 기술되어 있다.It is known in the field of emerging agents that certain 1-carbamoyl pyrazoline derivatives are pesticides. For example, US Pat. No. 4,174,393 also describes the pesticidal activity of 1-carbamoyl pyrazoline having phenyl substituents at positions 3 and 4 of the pyrazoline ring.

본 명세서에서 사용된 용어 "할로" 및 "할로겐"은 불소, 염소 또는 브롬을 말한다. "알킬", "알콕시", "알키닐옥시"등을 수식하는 용어 "저급"은 탄소원자 1 내지 6개, 바람직하게는 1 내지 4개를 함유하는 직쇄 또는 측쇄 탄화수소를 의미하며 ; 다른 용어와 결부된 "할로"는 하나 이상의 수소원자가 할로겐으로 치환된 것을 의미한다.The terms "halo" and "halogen" as used herein refer to fluorine, chlorine or bromine. The term "lower", such as "alkyl", "alkoxy", "alkynyloxy", etc., means a straight or branched chain hydrocarbon containing 1 to 6, preferably 1 to 4, carbon atoms; "Halo" in conjunction with another term means that one or more hydrogen atoms are replaced with halogen.

본 발명에 따르는 일반식(Ｉ) 화합물중, W가 산소인 화합물이 바람직하며, 특히

Figure kpo00025
가 4-치환체, 바람직하게는 염소 또는 불소와 같은 할로겐, 또는 디플루오로메톡시와 같은 저급 할로알콕시인 화합물이 바람직하다. RB가 4-치환체인 피라졸린이 일반적으로 상응하는 5-치환된 피라졸린 보다 더 활성이 있으며, RB가 치환체
Figure kpo00026
를 갖는 페닐인 화합물이 특히 관심있는 화합물이다. 본 발명에서는
Figure kpo00027
가 4-치환체, 특히 염소 또는 불소와 같은 할로겐인 경우가 바람직하다.Among the general formula (I) compounds according to the present invention, compounds in which W is oxygen are preferred, and in particular,
Figure kpo00025
Preference is given to compounds in which the tetrasubstituent is preferably halogen such as chlorine or fluorine or lower haloalkoxy such as difluoromethoxy. Pyrazolines in which R B is a 4-substituent are generally more active than the corresponding 5-substituted pyrazolines, and R B is a substituent
Figure kpo00026
Compounds of interest are compounds of particular interest. In the present invention
Figure kpo00027
It is preferred if is 4-substituted, in particular halogen, such as chlorine or fluorine.

RC와 관련하여, 가장 관심있는 살충제는 2,3-디하이드로-2,2-디메틸벤조푸란-5-일, 2,3-디하이드로-2,2,3,3-테트라플루오로벤조푸란-5-일, 2,3-디하이드로-2,2,3,3-테트라플루오로벤조푸란-6-일, 2,2-디플루오로-1,3-벤조디옥솔-5-일, 또는 2,2-디메틸-1,3-벤조디옥솔-5-일그룹이나 4-페녹시 페닐그룹을 갖는 화합물로 부터 유도된다. 후자의 경우에 RD가 수소인 경우 및 RE가 4-치환체, 특히 저급 할로알콕시인 경우가 바람직하다.With regard to R C , the pesticides of interest are 2,3-dihydro-2,2-dimethylbenzofuran-5-yl, 2,3-dihydro-2,2,3,3-tetrafluorobenzofuran -5-yl, 2,3-dihydro-2,2,3,3-tetrafluorobenzofuran-6-yl, 2,2-difluoro-1,3-benzodioxol-5-yl, Or a compound having a 2,2-dimethyl-1,3-benzodioxol-5-yl group or a 4-phenoxy phenyl group. In the latter case it is preferred if R D is hydrogen and R E is a 4-substituent, in particular lower haloalkoxy.

현저한 살충활성을 갖는 본 발명의 피라졸린은 예를 들어 3-(4-디플루오로메톡시페닐)-N-(2,3-디하이드로-2,2-디메틸벤조푸란-5-일)-4-페닐피라졸린-1-카복스아미드 ; 3,4-비스-(4-플루오로페닐)-N-2,3-디하이드로-2,2,3,3-테트라플루오로벤조푸란-5-일)피라졸린-1-카복스아미드 ; 3,4-비스(4-플루오로페닐)-N-(2,3-디하이드로-2,2-디메틸벤조푸란-5-일)피라졸린-1-카복스아미드; N-(2,3-디하이드로-2,2,3,3-테트라플루오로벤조푸란-5-일)-3-(4-디플루오로메톡시페닐)-4-페닐피라졸린-1-카복스아미드 ; N-(2,2-디플루오로-1,3-벤조디옥솔-5-일)-3-(4-디플루오로메톡시페닐)-N-메틸-4-페닐피라졸린-1-카복스아미드 ; 3,4-비스(4-클로로페닐)-N-(2,2-디메틸-1,3-벤조디옥솔-5-일)피라졸린-1-카복스아미드 ; N-(2,2-디플루오로-1,3-벤조디옥솔-5-일)-3,4-비스(4-플루오로페닐)피라졸린-1-카복스아미드 ; 3-(4-클로로페닐)-N-(2,2-디플루오로-1,3-벤조디옥솔-5-일)-4-(4-플루오로페닐)피라졸린-1-카복스아미드 ; 3-(4-디플루오로메톡시페닐)-N-(2,3-디하이드로-2,2,3,3-테트라플루오로벤조푸란-5-일)-N-메틸-4-페닐피라졸린-1-카복스아미드 ; 3-(4-클로로페닐)-N-[4-(4-디플루오로메톡시페녹시)페닐]-4-페닐피라졸린-1-카복스아미드 ; N-[4-(4-디플루오로메톡시페녹시)페닐]-3-(4-디플루오로메톡시페닐)-4-(4-플루오로페닐)피라졸린-1-카복스아미드 ; 3-(4-디플루오로메톡시페닐)-4-(4-플루오로페닐)-N-(2,3-디하이드로-2,2,3,3-테트라플루오로벤조푸란-5-일)피라졸린-1-카복스아미드 ; 3-(4-디플루오로메톡시페닐)-4-(4-플루오로페닐)-N-(2,3-디하이드로-(2,2,3,3-테트라플루오로벤조푸란-6-일)피라졸린-1-카복스아미드 ; 4-(4-클로로페닐)-N-(2,3-디하이드로)-2,2-디메틸벤조푸란-5-일)-3-페닐-피라졸린-1-카복스아미드 ; 3-(4-클로로페닐)-4-(4-플루오로페닐)-N-(2,3-디하이드로-2,2-디메틸벤조푸란-5-일)피라졸린-1-카복스아미드 ; 3-(4-디플루오로메톡시페닐)-4-(4-플루오로페닐)-N-(2,3-디하이드로-2,2-디메틸벤조푸란-5-일)피라졸린-1-카복스아미드 ; 및 4-(4-클로로페닐)-3-(4-디플루오로메톡시페닐)-N-(2,3-디하이드로-2,2-디메틸벤조푸란-5-일)피라졸린-1-카복스아미드를 포함한다.Pyrazolines of the invention having significant pesticidal activity are for example 3- (4-difluoromethoxyphenyl) -N- (2,3-dihydro-2,2-dimethylbenzofuran-5-yl) -4 -Phenylpyrazoline-1-carboxamide; 3,4-bis- (4-fluorophenyl) -N-2,3-dihydro-2,2,3,3-tetrafluorobenzofuran-5-yl) pyrazoline-1-carboxamide; 3,4-bis (4-fluorophenyl) -N- (2,3-dihydro-2,2-dimethylbenzofuran-5-yl) pyrazoline-1-carboxamide; N- (2,3-dihydro-2,2,3,3-tetrafluorobenzofuran-5-yl) -3- (4-difluoromethoxyphenyl) -4-phenylpyrazoline-1-car Voxamides; N- (2,2-difluoro-1,3-benzodioxol-5-yl) -3- (4-difluoromethoxyphenyl) -N-methyl-4-phenylpyrazoline-1-carbox Amides; 3,4-bis (4-chlorophenyl) -N- (2,2-dimethyl-1,3-benzodioxol-5-yl) pyrazoline-1-carboxamide; N- (2,2-difluoro-1,3-benzodioxol-5-yl) -3,4-bis (4-fluorophenyl) pyrazolin-1-carboxamide; 3- (4-chlorophenyl) -N- (2,2-difluoro-1,3-benzodioxol-5-yl) -4- (4-fluorophenyl) pyrazoline-1-carboxamide ; 3- (4-difluoromethoxyphenyl) -N- (2,3-dihydro-2,2,3,3-tetrafluorobenzofuran-5-yl) -N-methyl-4-phenylpyrazoline -1-carboxamide; 3- (4-chlorophenyl) -N- [4- (4-difluoromethoxyphenoxy) phenyl] -4-phenylpyrazoline-1-carboxamide; N- [4- (4-difluoromethoxyphenoxy) phenyl] -3- (4-difluoromethoxyphenyl) -4- (4-fluorophenyl) pyrazoline-1-carboxamide; 3- (4-difluoromethoxyphenyl) -4- (4-fluorophenyl) -N- (2,3-dihydro-2,2,3,3-tetrafluorobenzofuran-5-yl) Pyrazoline-1-carboxamides; 3- (4-difluoromethoxyphenyl) -4- (4-fluorophenyl) -N- (2,3-dihydro- (2,2,3,3-tetrafluorobenzofuran-6-yl Pyrazoline-1-carboxamide; 4- (4-Chlorophenyl) -N- (2,3-dihydro) -2,2-dimethylbenzofuran-5-yl) -3-phenyl-pyrazoline- 1-carboxamide; 3- (4-chlorophenyl) -4- (4-fluorophenyl) -N- (2,3-dihydro-2,2-dimethylbenzofuran-5-yl) pyrazolin-1-carboxamide; 3- (4-difluoromethoxyphenyl) -4- (4-fluorophenyl) -N- (2,3-dihydro-2,2-dimethylbenzofuran-5-yl) pyrazoline-1-car Voxamides; And 4- (4-chlorophenyl) -3- (4-difluoromethoxyphenyl) -N- (2,3-dihydro-2,2-dimethylbenzofuran-5-yl) pyrazolin-1-ca Voxamides.

본 발명에는 또한 상기 언급한 피라졸린중 적어도 하나의 살충 유효량과 농업적으로 무독한 담체로 이루어진 살충제 조성물도 포함된다. 또한, 본 발명에는 처리 대상지역에 언급한 피라졸린중 적어도 하나를 살충 유효량으로 사용하여 해충을 구제하는 방법도 포함된다.The present invention also encompasses pesticide compositions consisting of an insecticidal effective amount of at least one of the aforementioned pyrazolines and an agriculturally nontoxic carrier. The present invention also includes a method of controlling pests by using at least one of the pyrazolines mentioned in the region to be treated in an insecticidal effective amount.

본 발명에 따르는 피라졸린은 적절한 방향족 이소시아네이트 또는 이소티오시아네이트를 적절히 치환된 피라졸린과 결합시켜 제조할 수 있으며, 이의 반응도식은 다음과 같다.The pyrazoline according to the invention can be prepared by combining an appropriate aromatic isocyanate or isothiocyanate with an appropriately substituted pyrazoline, the scheme of which is as follows.

Figure kpo00028
Figure kpo00028

Figure kpo00029
Figure kpo00029

생성물은 공지의 방법으로 알킬화하여 상응하는 N-알킬화 피라졸린을 수득할 수 있다.The product can be alkylated by known methods to yield the corresponding N-alkylated pyrazolines.

적절히 치환된 피라졸린 출발물질은 일반적으로 공지되어 있는 화합물이다. 필수 이소시아네이트 및 이소티오시아네이트는 상응하는 아민으로 부터 제조할 수 있다. 여러가지의 아민이 시판되고 있다. 다른 관심이 있는 아민은 다음 실시예에 기술된 방법으로 제조할 수 있다.Properly substituted pyrazoline starting materials are generally known compounds. Essential isocyanates and isothiocyanates can be prepared from the corresponding amines. Various amines are commercially available. Other amines of interest can be prepared by the methods described in the following examples.

[실시예 1]Example 1

3-(4-클로로페닐)-N-[4-(4-클로로페녹시)페닐]-4-페닐피라졸린-1-카복스아미드3- (4-chlorophenyl) -N- [4- (4-chlorophenoxy) phenyl] -4-phenylpyrazoline-1-carboxamide

무수 질소 대기하에 디메틸설폭사이드 175ml중의 4-플루오로니트로벤젠 10.9g(0.077몰), 4-클로로페놀 9.95g(0.077몰) 및 탄산 칼륨 11.8g(0.085몰)의 교반 호나합물을 70℃에서 2일간 가열한다. 반응 혼합물을 냉각하고 여과한다. 여액을 1ℓ의 용적이 되도록 물로 희석한다. 이 혼합물을 디에틸 에테를 200ml씩으로 3회 추출한다. 에테르 추출물을 합하여 물로 세척하고, 이어서 포화 염화 나트륨 수용액으로 세척한다. 세척한 추출물을 무수 황산 나트륨상에서 건조하고 여과한다.10.9 g (0.077 mol) of 4-fluoronitrobenzene, 9.95 g (0.077 mol) of 4-chlorophenol and 11.8 g (0.085 mol) of potassium carbonate in 175 ml of dimethyl sulfoxide under anhydrous nitrogen atmosphere Heat for days. The reaction mixture is cooled and filtered. The filtrate is diluted with water to a volume of 1 liter. The mixture is extracted three times with 200 ml of diethyl ether. The combined ether extracts are washed with water and then with saturated aqueous sodium chloride solution. The washed extract is dried over anhydrous sodium sulfate and filtered.

여액을 감압하에 증발시켜 4-(4-클로로페녹시)니트로벤젠(융점 67 내지 70℃) 13.5g을 수득한다.The filtrate was evaporated under reduced pressure to give 13.5 g of 4- (4-chlorophenoxy) nitrobenzene (melting point 67-70 ° C.).

4-(4-클로로페녹시)니트로벤젠 13.5g(0.054몰)을 테트라하이드로푸란 250ml중의 산화백금 촉매량(0.15g)으로 수소화하면 4-(4-클로로페녹시)아닐린 정량이 수득된다.Hydrogenation of 13.5 g (0.054 mol) of 4- (4-chlorophenoxy) nitrobenzene with a catalytic amount of platinum oxide (0.15 g) in 250 ml of tetrahydrofuran yielded a quantitative determination of 4- (4-chlorophenoxy) aniline.

톨루엔 25ml중의 4-(4-클로로페녹시)아닐린 0.75g(0.0034몰)의 교반용액에 톨루엔 20ml중의 트리클로로 메틸클로로포르메이트 0.43ml(0.0036몰)의 용액을 적가한다. 적가가 끝난후, 혼합물을 85℃에서 3시간 동안 가열한다. 이 혼합물을 실온으로 냉각하고 용매를 감압하에 증발시켜 잔사를 얻는다. 잔사를 디에틸 에테르 25ml에 용해한다. 이 용액을 디에틸 에테르중의 3-(4-클로로페닐)-4-페닐피라졸린 1.0g(0.0034몰)의 교반된 슬러리에 적가한다. 트리에틸아민 3적을 가하고 혼합물을 2일 동안 실온에서 교반한다.To a stirred solution of 0.75 g (0.0034 mol) of 4- (4-chlorophenoxy) aniline in 25 ml of toluene was added dropwise a solution of 0.43 ml (0.0036 mol) of trichloro methylchloroformate in 20 ml of toluene. After the dropping, the mixture is heated at 85 ° C. for 3 hours. The mixture is cooled to room temperature and the solvent is evaporated under reduced pressure to give a residue. The residue is dissolved in 25 ml of diethyl ether. This solution is added dropwise to 1.0 g (0.0034 mole) of a stirred slurry of 3- (4-chlorophenyl) -4-phenylpyrazoline in diethyl ether. Three drops of triethylamine are added and the mixture is stirred for 2 days at room temperature.

용매를 혼합물로 부터 증발시켜 3-(4-클로로페닐)-N-[4-(4-클로로페녹시)페닐]-4-페닐피라졸린-1-카복스아미드 0.92g(융점 : 158 내지 161℃)을 수득한다.The solvent was evaporated from the mixture to give 0.92 g of 3- (4-chlorophenyl) -N- [4- (4-chlorophenoxy) phenyl] -4-phenylpyrazoline-1-carboxamide (melting point: 158 to 161). C) is obtained.

원소분석 :Elemental Analysis:

계 산 치 : C 66.92 H 4.22Calculated Value: C 66.92 H 4.22

실 측 치 : C 66.06 H 4.95Found: C 66.06 H 4.95

nmr : 8.06ppm(CDCl3)nmr: 8.06 ppm (CDCl 3 )

[실시예 2]Example 2

3-(4-클로로페닐)-N-(2,3-디하이드로-2,2-디메틸벤조푸란-5-일)-4-페닐피라졸린-1-카복스아미드3- (4-chlorophenyl) -N- (2,3-dihydro-2,2-dimethylbenzofuran-5-yl) -4-phenylpyrazoline-1-carboxamide

1시간 동안 5℃의 온도를 유지하면서 농질산 43ml 및 농황산 50ml의 빙냉 혼합물을 2,3-디하이드로-2,2-디메틸벤조푸란 100g(0.67몰)에 적가한다. 적가가 끝난후 혼합물을 0℃에서 2.5시간 동안 교반한다. 반응 혼합물을 빙수에 붓고 전부 디에틸에테르로 추출한다. 추출물을 무수 염화 마그네슘상에서 건조하여 여과한다. 여액을 감압하에 증발하여 흑색 오일을 얻는다. 이 오일을 톨루엔 : n-헥산(9 : 1)으로 용출하면서 실리카겔상에서 컬럼 크로마토그라피로 정제하면 2,3-디하이드로-2,2-디메틸-5-니트로벤조푸란 50.0g이 고체로 수득된다.An ice-cold mixture of 43 ml of concentrated nitric acid and 50 ml of concentrated sulfuric acid was added dropwise to 100 g (0.67 mol) of 2,3-dihydro-2,2-dimethylbenzofuran while maintaining the temperature at 5 ° C. for 1 hour. After the dropwise addition the mixture is stirred at 0 ° C. for 2.5 h. The reaction mixture is poured into ice water and extracted with diethyl ether. The extract is dried over anhydrous magnesium chloride and filtered. The filtrate is evaporated under reduced pressure to give a black oil. The oil was purified by column chromatography on silica gel, eluting with toluene: n-hexane (9: 1) to give 50.0 g of 2,3-dihydro-2,2-dimethyl-5-nitrobenzofuran as a solid.

2,3-디하이드로-2,2-디메틸-5-니트로벤조푸란 20.0g(0.1몰)을 메탄을 250ml중의 산화백금 촉매량(0.2g)으로 수소화하여 5-아미노-2,3-디하이드로-2,2-디메틸벤조푸란 16.6g을 수득한다.20.0 g (0.1 mol) of 2,3-dihydro-2,2-dimethyl-5-nitrobenzofuran was hydrogenated with a catalytic amount of platinum oxide (0.2 g) in 250 ml of 5-amino-2,3-dihydro- 16.6 g of 2,2-dimethylbenzofuran is obtained.

톨루엔 20ml중의 트리클로로메틸클로로포르메이트 0.43ml(0.0036몰)의 용액을 톨루엔 20ml중의 5-아미노-2,3-디하이드로-2,2-디메틸벤조푸란 0.56g(0.0034몰)의 교반용액에 적가한다. 적가가 끝나면, 혼합물을 3시간 동안 환류 가열한다. 혼합물을 실온으로 냉각시키고 용매를 감압하에 증발시켜 잔사를 유리시킨다. 잔사를 부수 디에틸 에테르 25ml에 용해하고 용액을 디에틸 에테르 25ml중의 3-(4-클로로페닐)-4-페닐피라졸린 1.0g(0.0034몰) 및 트리에틸아민 3적의 교반 혼합물에 적가한다. 반응 혼합물을 실온에서 대략 18시간 동안 교반한 후 혼합물로 부터 고체를 여과해낸다. 여과케익을 에탄올중에 슬러리화하고 여과하여 회수하면 3-(4-클로로페닐)-N-(2,3-디하이드로-2,2-디메틸벤조푸란-5-일)-4-페닐피라졸린-1-카복스아미드(융점 :160 내지 162℃) 0.47g이 수득된다.A solution of 0.43 ml (0.0036 mol) of trichloromethylchloroformate in 20 ml of toluene was added dropwise to a stirring solution of 0.56 g (0.0034 mol) of 5-amino-2,3-dihydro-2,2-dimethylbenzofuran in 20 ml of toluene. do. At the end of the dropping, the mixture is heated to reflux for 3 hours. The mixture is cooled to room temperature and the solvent is evaporated under reduced pressure to liberate the residue. The residue is dissolved in 25 ml of incidental diethyl ether and the solution is added dropwise to a stirred mixture of 1.0 g (0.0034 mole) and triethylamine 3 drops of 3- (4-chlorophenyl) -4-phenylpyrazoline in 25 ml of diethyl ether. The reaction mixture is stirred at room temperature for approximately 18 hours before the solids are filtered off of the mixture. The filter cake was slurried in ethanol and collected by filtration to recover 3- (4-chlorophenyl) -N- (2,3-dihydro-2,2-dimethylbenzofuran-5-yl) -4-phenylpyrazoline- 0.47 g of 1-carboxamide (melting point: 160 to 162 ° C) is obtained.

원소분석 :Elemental Analysis:

계 산 치 : C 70.00 ; H 5.43Calculated Value: C 70.00; H 5.43

실 측 치 : C69.50 ; H 3.36Found: C69.50; H 3.36

nmr : 9.00ppm(DMSO-d6)nmr: 9.00 ppm (DMSO-d 6 )

유사한 방법으로 제조된 다른 화합물은 다음의 실시예로 나타내었다. 융점은 ℃로 주어진다. 이들 화함루의 특성인, =NH양자에 상응하는 nmr 단일선은 몇몇 경우에만 주어졌으며, 달리 언급된 바 없으며, nmr용매는 CDCl3이다. 몇몇 경우에 원소 분석을 기재하였다.Other compounds prepared in a similar manner are shown in the following examples. The melting point is given in degrees Celsius. The nmr singlet corresponding to the = NH quantum, which is characteristic of these influenza, is given in some cases and is not mentioned otherwise, the nmr solvent is CDCl 3 . In some cases elemental analysis has been described.

[실시예 3]Example 3

3,4-디페닐-N-(4-페녹시페닐)피라졸린-1-카복스아미드, 융점 : 184 내지 188, 9.17ppm(DMSO-d6)3,4-diphenyl-N- (4-phenoxyphenyl) pyrazoline-1-carboxamide, Melting point: 184 to 188, 9.17 ppm (DMSO-d 6 )

[실시예 4]Example 4

N-[4(4-클로로페녹시)페닐]-3,4-디페닐피라졸린-1-카복스아미드, 융점 : 146 내지 149, 8.83ppm(DMSO-d6)N- [4 (4-chlorophenoxy) phenyl] -3,4-diphenylpyrazolin-1-carboxamide, Melting point: 146 to 149, 8.83 ppm (DMSO-d 6 )

[실시예 5]Example 5

3-(4-클로로페닐)-N-(4-페녹시페닐)-4-페닐피라졸린-1-카복스아미드, 융점 : 163 내지 166, 8.03ppm3- (4-Chlorophenyl) -N- (4-phenoxyphenyl) -4-phenylpyrazoline-1-carboxamide, Melting Point: 163 to 166, 8.03 ppm

[실시예 6]Example 6

N-(4-페녹시페닐)-4-페닐-3-(4-트리플루오로메틸페닐)피라졸린-1-카복스아미드, 융점 : 188 내지 190, 8.10ppmN- (4-phenoxyphenyl) -4-phenyl-3- (4-trifluoromethylphenyl) pyrazoline-1-carboxamide, Melting point: 188 to 190, 8.10 ppm

[실시예 7]Example 7

3,4-비스-(4-클로로페닐)-N-(4-페녹시페닐)피라졸린-1-카복스아미드, 융점 : 189 내지 193, 8.20ppm(CDCl3/DMSO-d6)3,4-bis- (4-chlorophenyl) -N- (4-phenoxyphenyl) pyrazoline-1-carboxamide, Melting Point: 189-193, 8.20 ppm (CDCl 3 / DMSO-d 6 )

[실시예 8]Example 8

3-(4-클로로페닐)-N-(3-메틸-4-페녹시페닐)-4-페닐피라졸린-1-카복스아미드, 융점 : 151 내지 157, 9.13ppm(DMSO-d6)3- (4-Chlorophenyl) -N- (3-methyl-4-phenoxyphenyl) -4-phenylpyrazolin-1-carboxamide, Melting Point: 151 to 157, 9.13 ppm (DMSO-d 6 )

[실시예 9]Example 9

3-(4-클로로페닐)-N-[4-(2-플루오로페녹시)페닐]-4-페닐피라졸린-1-카복스아미드, 융점 : 153 내지 155, 8.16ppm3- (4-chlorophenyl) -N- [4- (2-fluorophenoxy) phenyl] -4-phenylpyrazoline-1-carboxamide, Melting Point: 153 to 155, 8.16 ppm

[실시예 10]Example 10

3-(4-클로로페닐)-N-[4-(3-플루오로페녹시)페닐)-4-페닐피라졸린-1-카복스아미드, 융점 : 173 내지 175, 9.33ppm(DMSO-d6)3- (4-Chlorophenyl) -N- [4- (3-fluorophenoxy) phenyl) -4-phenylpyrazoline-1-carboxamide, Melting Point: 173 to 175, 9.33 ppm (DMSO-d 6 )

[실시예 11]Example 11

N-[4-(3-클로로페녹시)페닐]-3-(4-클로로페닐)-4-페닐피라졸린-1-카복스아미드, 융점 : 169 내지 174, 9.30ppm(DMSO-d6)N- [4- (3-chlorophenoxy) phenyl] -3- (4-chlorophenyl) -4-phenylpyrazolin-1-carboxamide, Melting point: 169 to 174, 9.30 ppm (DMSO-d 6 )

[실시예 12]Example 12

3-(4-클로로페닐)-N-[4-(4-플루오로페녹시)페닐]-4-페닐피라졸린-1-카복스아미드, 융점 : 164 내지 167, 8.13ppm3- (4-chlorophenyl) -N- [4- (4-fluorophenoxy) phenyl] -4-phenylpyrazoline-1-carboxamide, Melting point: 164 to 167, 8.13 ppm

[실시예 13]Example 13

3-(4-클로로페닐)-N-[4-(4-트리플루오로메틸페녹시)페닐]-4-페닐피라졸린-1-카복스아미드, 융점 : 161 내지 164, 8.03ppm3- (4-chlorophenyl) -N- [4- (4-trifluoromethylphenoxy) phenyl] -4-phenylpyrazoline-1-carboxamide, Melting point: 161 to 164, 8.03 ppm

[실시예 14]Example 14

N-[4-(4-클로로페녹시)페닐]-3-(4-디플루오로메톡시페닐)-4-페닐피라졸린-1-카복스아미드, 융점 : 103 내지 107, 8.00ppmN- [4- (4-chlorophenoxy) phenyl] -3- (4-difluoromethoxyphenyl) -4-phenylpyrazoline-1-carboxamide, Melting point: 103-107, 8.00 ppm

[실시예 15]Example 15

3,4-비스(4-클로로페닐)-N-(3-메틸-4-페녹시페닐)피라졸린-1-카복스아미드, 융점 : 188 내지 190, 9.23ppm(DMSO-d6)3,4-bis (4-chlorophenyl) -N- (3-methyl-4-phenoxyphenyl) pyrazoline-1-carboxamide, melting point: 188 to 190, 9.23 ppm (DMSO-d 6 )

[실시예 16]Example 16

3,4-비스(4-클로로페닐)-N-[4-(2-플루오로페녹시)페닐]-피라졸린-1-카복스아미드, 융점 : 160 내지 162, 8.10ppm3,4-bis (4-chlorophenyl) -N- [4- (2-fluorophenoxy) phenyl] -pyrazoline-1-carboxamide, Melting point: 160-162, 8.10 ppm

[실시예 17]Example 17

3,4-비스(4-클로로페닐)-N-[4-(3-플루오로페녹시)페닐]-피라졸린-1-카복스아미드, 융점 : 144 내지 146, 9.20ppm(DMSO-d6)3,4-bis (4-chlorophenyl) -N- [4- (3-fluorophenoxy) phenyl] -pyrazoline-1-carboxamide, Melting point: 144-146, 9.20 ppm (DMSO-d 6 )

[실시예 18]Example 18

N-[4-(3-클로로페녹시)페닐]-3,4-비스(4-클로로페닐)피라졸린-1-카복스아미드, 융점 : 135 내지 140, 9.30ppm(DMSO-d6)N- [4- (3-chlorophenoxy) phenyl] -3,4-bis (4-chlorophenyl) pyrazoline-1-carboxamide, Melting point: 135 to 140, 9.30 ppm (DMSO-d 6 )

[실시예 19]Example 19

3,4-비스(4-클로로페닐)-N-[4-(4-플루오로페녹시)페닐]피라졸린-1-카복스아미드, 융점 : 168 내지 170, 9.23ppm(DMSO-d6)3,4-bis (4-chlorophenyl) -N- [4- (4-fluorophenoxy) phenyl] pyrazoline-1-carboxamide, Melting point: 168 to 170, 9.23 ppm (DMSO-d 6 )

[실시예 20]Example 20

N-[4-(4-클로로페녹시)페닐]-3,4-비스(4-클로로페닐)피라졸린-1-카복스아미드, 융점 : 154 내지 156, 9.30ppm(DMSO-d6)N- [4- (4-chlorophenoxy) phenyl] -3,4-bis (4-chlorophenyl) pyrazoline-1-carboxamide, Melting point: 154 to 156, 9.30 ppm (DMSO-d 6 )

[실시예 21]Example 21

3,4-비스(4-클로로페닐)-N-[4-(4-트리플루오로메틸페녹시)페닐]-피라졸린-1-카복스아미드, 융점 : 191 내지 194, 9.30ppm(DMSO-d6)3,4-bis (4-chlorophenyl) -N- [4- (4-trifluoromethylphenoxy) phenyl] -pyrazoline-1-carboxamide, melting point: 191-194, 9.30 ppm (DMSO- d 6 )

[실시예 22]Example 22

3-(4-클로로페닐)-4-페닐-N-(4-페닐티오페닐)피라졸린-1-카복스아미드, 융점 : 157 내지 162, 8.20ppm3- (4-chlorophenyl) -4-phenyl-N- (4-phenylthiophenyl) pyrazoline-1-carboxamide, Melting Point: 157-162, 8.20ppm

[실시예 23]Example 23

3,4-비스(4-클로로페닐)-N-(4-페닐티오페닐)피라졸린-1-카복스아미드, 융점 : 169 내지 171, 8.20ppm3,4-bis (4-chlorophenyl) -N- (4-phenylthiophenyl) pyrazoline-1-carboxamide, Melting point: 169 to 171, 8.20 ppm

[실시예 24]Example 24

3,5-비스(4-클로로페닐)-N-(4-페녹시페닐)피라졸린-1-카복스아미드, 융점 : 168 내지 170, 8.30ppm(CDCl3/DMSO-d6)3,5-bis (4-chlorophenyl) -N- (4-phenoxyphenyl) pyrazoline-1-carboxamide, Melting point: 168 to 170, 8.30 ppm (CDCl 3 / DMSO-d 6 )

[실시예 25]Example 25

3-(4-클로로페닐)-5-(4-트리플루오로메틸페닐)-N-(4-페녹시페닐)피라졸린-1-카복스아미드, 융점 : 164 내지 167, 8.00ppm3- (4-Chlorophenyl) -5- (4-trifluoromethylphenyl) -N- (4-phenoxyphenyl) pyrazoline-1-carboxamide, Melting point: 164 to 167, 8.00 ppm

[실시예 26]Example 26

3,5-비스(4-클로로페닐)-N-[4-(2-플루오로페녹시)페닐]-피라졸린-1-카복스아미드, 융점 : 174 내지 178, 8.50ppm3,5-bis (4-chlorophenyl) -N- [4- (2-fluorophenoxy) phenyl] -pyrazoline-1-carboxamide, Melting point: 174 to 178, 8.50 ppm

[실시예 27]Example 27

3,5-비스(4-클로로페닐)-N-[4-(3-플루오로페녹시)페닐]-피라졸린-1-카복스아미드, 융점 : 164 내지 168, 9.00ppm(DMSO-d6)3,5-bis (4-chlorophenyl) -N- [4- (3-fluorophenoxy) phenyl] -pyrazoline-1-carboxamide, Melting point: 164 to 168, 9.00 ppm (DMSO-d 6 )

[실시예 28]Example 28

3,5-비스(4-클로로페닐)-N-[4-(4-플루오로페녹시)페닐]-피라졸린-1-카복스아미드, 융점 : 165 내지 167, 9.16ppm(DMSO-d6)3,5-bis (4-chlorophenyl) -N- [4- (4-fluorophenoxy) phenyl] -pyrazoline-1-carboxamide, Melting point: 165 to 167, 9.16 ppm (DMSO-d 6 )

[실시예 29]Example 29

N-[4-(4-클로로페녹시)페닐]-3,5-비스(4-클로로페닐)-피라졸린-1-카복스아미드, 융점 : 142 내지 144, 9.20ppm(DMSO-d6)N- [4- (4-chlorophenoxy) phenyl] -3,5-bis (4-chlorophenyl) -pyrazoline-1-carboxamide, melting point: 142-144, 9.20 ppm (DMSO-d 6 )

[실시예 30]Example 30

3,5-비스(4-클로로페닐)-N-[4-(4-트리플루오로메틸페녹시)페닐]-피라졸린-1-카복스아미드, 융점 : 155 내지 158, 8.43ppm(CDCl3/DMSO-d6)3,5-bis (4-chlorophenyl) -N- [4- (4-trifluoromethylphenoxy) phenyl] -pyrazoline-1-carboxamide, Melting point: 155-158, 8.43 ppm (CDCl 3 / DMSO-d 6 )

[실시예 31]Example 31

3-(4-클로로페닐)-N-[4-(4-트리플루오로메틸페녹시)페닐]-5-(4-트리플루오로메틸페닐)피라졸린-1-카복스아미드, 융점 : 144 내지 146, 8.06ppm3- (4-chlorophenyl) -N- [4- (4-trifluoromethylphenoxy) phenyl] -5- (4-trifluoromethylphenyl) pyrazoline-1-carboxamide, melting point: 144 to 146, 8.06ppm

[실시예 32]Example 32

N-[4-(4-클로로페녹시)페닐]-5-(4-클로로페닐)-3-(4-디플루오로메톡시페닐)피라졸린-1-카복스아미드, 융점 : 66 내지 70, 8.60ppm(DMSO-d6)N- [4- (4-chlorophenoxy) phenyl] -5- (4-chlorophenyl) -3- (4-difluoromethoxyphenyl) pyrazoline-1-carboxamide, Melting point: 66-70, 8.60 ppm (DMSO-d 6 )

[실시예 33]Example 33

5-(1,3-벤조디옥솔-5-일)-3-(4-클로로페닐)-N-(4-페녹시페닐)-피라졸린-1-카복스아미드, 융점 : 125 내지 128, 8.36ppm(CDCl3/DMSO-d6)5- (1,3-benzodioxol-5-yl) -3- (4-chlorophenyl) -N- (4-phenoxyphenyl) -pyrazolin-1-carboxamide, melting point: 125-128, 8.36 ppm (CDCl 3 / DMSO-d 6 )

[실시예 34]Example 34

5-(1,3-벤조디옥솔-5-일)-N-[4-(4-클로로페녹시)페닐]-3-(4-클로로페닐)피라졸린-1-카복스아미드, 융점 : 174 내지 175, 8.06ppm5- (1,3-benzodioxol-5-yl) -N- [4- (4-chlorophenoxy) phenyl] -3- (4-chlorophenyl) pyrazolin-1-carboxamide, Melting point: 174 to 175, 8.06 ppm

[실시예 35]Example 35

N-(2,3-디하이드로-2,2-디메틸벤조푸란-5-일)-3,4-디페닐피라졸린-1-카복스아미드, 융점 : 139 내지 143, 7.96ppmN- (2,3-dihydro-2,2-dimethylbenzofuran-5-yl) -3,4-diphenylpyrazolin-1-carboxamide, Melting point: 139 to 143, 7.96 ppm

[실시예 36]Example 36

3-(4-디플루오로메톡시페닐)-N-(2,3-디하이드로-2,2-디메틸벤조푸란-5-일)-4-페닐피라졸린-1-카복스아미드, 융점 : 75 내지 82, 7.96ppm3- (4-Difluoromethoxyphenyl) -N- (2,3-dihydro-2,2-dimethylbenzofuran-5-yl) -4-phenylpyrazolin-1-carboxamide, Melting point: 75 To 82, 7.96 ppm

[실시예 37]Example 37

(±)-3,4-비스-(4-클로로페닐)-N-(2,3-디하이드로-2,2-디메틸벤조푸란-5-일)피라졸린-1-카복스아미드, 융점 : 134 내지 137, 7.93ppm(±) -3,4-bis- (4-chlorophenyl) -N- (2,3-dihydro-2,2-dimethylbenzofuran-5-yl) pyrazolin-1-carboxamide, Melting point: 134 to 137, 7.93 ppm

[실시예 38]Example 38

3,5-비스(4-클로로페닐)-N-(2,3-디하이드로-2,2-디메틸벤조푸란-5-일)피라졸린-1-카복스아미드, 융점 : 175 내지 180, 8.86ppm(DMSO-d6)3,5-bis (4-chlorophenyl) -N- (2,3-dihydro-2,2-dimethylbenzofuran-5-yl) pyrazolin-1-carboxamide, Melting point: 175 to 180, 8.86 ppm (DMSO-d 6 )

[실시예 39]Example 39

N-(1,4-벤조디옥산-6-일)-3-(4-클로로페닐)-4-페닐피라졸린-1-카복스아미드, 융점 : 112 내지 115, 7.96ppmN- (1,4-benzodioxan-6-yl) -3- (4-chlorophenyl) -4-phenylpyrazolin-1-carboxamide, Melting point: 112 to 115, 7.96 ppm

[실시예 40]Example 40

N-(1,4-벤조디옥산-6-일)-3,4-비스(4-클로로페닐)피라졸린-1-카복스아미드, 융점 : 140 내지 145, 7.96ppmN- (1,4-benzodioxan-6-yl) -3,4-bis (4-chlorophenyl) pyrazoline-1-carboxamide, Melting point: 140 to 145, 7.96 ppm

[실시예 41]Example 41

3-(4-클로로페닐)-N-(4-페녹시페닐)-4-페닐피라졸린-1-카보티오아미드, 융점 : 105 내지 110, 10.30ppm(DMSO-d6)3- (4-Chlorophenyl) -N- (4-phenoxyphenyl) -4-phenylpyrazoline-1-carbothioamide, Melting point: 105 to 110, 10.30 ppm (DMSO-d 6 )

[실시예 42]Example 42

3,4-비스(4-클로로페닐)-N-(4-페녹시페닐)피라졸린-1-카보티오아미드, 융점 : 151 내지 153, 9.26ppm(DMSO-d6)3,4-bis (4-chlorophenyl) -N- (4-phenoxyphenyl) pyrazoline-1-carbothioamide, Melting point: 151 to 153, 9.26 ppm (DMSO-d 6 )

[실시예 43]Example 43

N-[4-(4-클로로페녹시)페닐]-3,4-비스(4-클로로페닐)-피라졸린-1-카보티오아미드, 융점 : 179 내지 183, 9.10ppmN- [4- (4-chlorophenoxy) phenyl] -3,4-bis (4-chlorophenyl) -pyrazoline-1-carbothioamide, Melting point: 179 to 183, 9.10 ppm

[실시예 44]Example 44

3-(4-클로로페닐)-N-(2,3-디하이드로-2,2-디메틸벤조푸란-5-일)-4-페닐피라졸린-1-카보티오아미드, 융점 : 92 내지 95, 10.12ppm(DMSO-d6)3- (4-chlorophenyl) -N- (2,3-dihydro-2,2-dimethylbenzofuran-5-yl) -4-phenylpyrazolin-1-carbothioamide, melting point: 92 to 95, 10.12 ppm (DMSO-d 6 )

[실시예 45]Example 45

3,4-비스(4-클로로페닐)-N-(2,3-디하이드로-2,2-디메틸벤조푸란-5-일)피라졸린-1-카보티오아미드, 융점 : 149 내지 154, 9.00ppm(DMSO-d6)3,4-bis (4-chlorophenyl) -N- (2,3-dihydro-2,2-dimethylbenzofuran-5-yl) pyrazolin-1-carbothioamide, Melting point: 149 to 154, 9.00 ppm (DMSO-d 6 )

[실시예 46]Example 46

N-(1,4-벤조디옥산-6-일)-3,5-비스(4-클로로페닐)피라졸린-1-카복스아미드, 융점 : 83 내지 85, 9.33ppm(DMSO-d6)N- (1,4-benzodioxan-6-yl) -3,5-bis (4-chlorophenyl) pyrazoline-1-carboxamide, Melting point: 83 to 85, 9.33 ppm (DMSO-d 6 )

[실시예 47]Example 47

5-(4-클로로페닐)-3-(4-트리플루오로메틸페닐)-N-[4-(4-트리플루오로메틸페녹시)페닐]피라졸린-1-카복스아미드, 융점 : 183 내지 185, 8.77ppm(CDCl3/DMSO-d6)5- (4-chlorophenyl) -3- (4-trifluoromethylphenyl) -N- [4- (4-trifluoromethylphenoxy) phenyl] pyrazoline-1-carboxamide, Melting point: 183 to 185, 8.77 ppm (CDCl 3 / DMSO-d 6 )

[실시예 48]Example 48

N-(2,3-디하이드로-2,2,3,3-테트라플루오로벤조푸란-5-일)-3-(4-디플루오로메톡시페닐)-4-페닐피라졸린-1-카복스아미드N- (2,3-dihydro-2,2,3,3-tetrafluorobenzofuran-5-yl) -3- (4-difluoromethoxyphenyl) -4-phenylpyrazoline-1-car Voxamide

압력병에 2-클로로-4-니트로페놀 15.0g(0.086몰), 탄산 칼륨 11.9g(0.086몰), 프로판티올 1.5g(0.02몰), 1,2-디브로모테트라플루오로에탄 33.7g(0.13몰) 및 N,N-디메틸포름아미드 115ml를 넣는다. 압력병을 밀봉하고 혼합물을 50°에서 48시간 동안 교반한다. 압력병을 실온으로 냉각하여 개방하고 내용물을 분액 여두에 붓는다. 2N 수산화나트륨 용액 대략 200ml를 분액 여두에 가한다. 생성된 혼합물을 디에틸 에테르 300ml씩으로 4회 추출한다. 추출물을 합하여 2N 수산화나트륨 용액 100ml씩으로 2회 세척한다. 세척한 추출물을 무수 황산 마그네슘 상에서 건조하여 여과한다. 여액을 감압하에 증발시키면 오일이 유리된다. 상술한 반응을 3회 더 반복하여 수행한다. 4회의 실험으로 부터의 잔류 오일을 합하여, n-헵탄 : 톨루엔(95 : 5)을 용출제로 사용하여 실리카겔상에서 칼럼 크로마토그라피에 의해 정제하면 3-클로로-4-(2-브로모-1,1,2,2-테트라플루오로에톡시)니트로벤젠 57.6g이 오일로 수득된다.15.0 g (0.086 mol) of 2-chloro-4-nitrophenol, 11.9 g (0.086 mol) of potassium carbonate, 1.5 g (0.02 mol) of propanethiol, 33.7 g of 1,2-dibromotetrafluoroethane in a pressure bottle 0.13 mol) and 115 ml of N, N-dimethylformamide are added. Seal the pressure bottle and stir the mixture at 50 ° for 48 hours. Cool the pressure bottle to room temperature and open it and pour the contents into the separatory filter. Approximately 200 ml of 2N sodium hydroxide solution is added to the separation filter. The resulting mixture is extracted four times with 300 ml of diethyl ether. The extracts were combined and washed twice with 100 ml of 2N sodium hydroxide solution. The washed extract is dried over anhydrous magnesium sulfate and filtered. The oil is liberated when the filtrate is evaporated under reduced pressure. The above reaction is repeated three more times. The remaining oils from the four experiments were combined and purified by column chromatography on silica gel using n-heptane: toluene (95: 5) as eluent 3-chloro-4- (2-bromo-1,1 57.6 g of 2,2-tetrafluoroethoxy) nitrobenzene are obtained as an oil.

압력병에 3-틀로로-4-(2-브로모-1,1,2,2,-테트라플루오로에톡시)-니트로벤젠 10.0g(0.028몰), 구리분말(200메쉬) 9.0g(0.14몰), 2,2'-비피리딜 0.45g(0.0028몰) 및 디메틸설폭사이드 40ml를 넣는다. 압력병을 밀봉하고 반응 혼합물을 190 내지 195°에서 2시간 동안 교반한다. 압력병을 실온으로 냉각하고 개방하여 내용물을 분액 여두에 붓는다. 2N 염산 용액 대략 200ml를 분액 여두에 가한다. 혼합물을 디에틸 에테르 150ml씩으로 3회 추출한다. 추출물을 합하고 2N 염산 용액 200ml, 포화 염화나트륨 수용액 200ml, 및 2N 수산화나트륨 용액 200ml로 연속해서 세척한다. 세척한 추출물을 무수황산 마그네슘상에서 건조하여 여과한다. 용매를 감압하에 증발시켜 오일을 얻는다. 상기 언급한 반응을 6회 더 반복하여 수행한다. 7회의 실험으로 부터 잔유 오일을 합하고 톨루엔을 용출제로 사용하여 실리카겔상에서 칼럼 크로마토그라피하면 황색오일이 수득된다. 이 오일을 메틸사이클로헥산 125ml에 용해하고 용액을 대략 18시간 동안 냉동기에 넣는다. 생성된 결정을 여과에 의해 모으면 2,2,3,3-테트라플루오로-5-니트로벤조푸란 20.7g이 수득된다. 여액을 감압하에 증발시키면 오일이 남는다. 이 오일을 감압하에 증류시켜 생성물 3.0g(비점 : 75℃/0.2mmHg)을 더 수득한다. 2,2,3,3-테트라플루오로-5-니트로벤젠 2.15g(0.011몰)을 메탄올 150ml중의 산화백금 촉매량(0.25g)으로 수소화하여 5-아미노-2,2,3,3-테트라플루오로벤조푸란 2.15g을 수득한다.In a pressure bottle, 10.0 g (0.028 mol) of 3-fluoro-4- (2-bromo-1,1,2,2, -tetrafluoroethoxy) -nitrobenzene, 9.0 g of copper powder (200 mesh) 0.14 mol), 0.45 g (0.0028 mol) of 2,2'-bipyridyl and 40 ml of dimethyl sulfoxide are added thereto. The pressure bottle is sealed and the reaction mixture is stirred at 190 to 195 ° for 2 hours. Cool the pressure bottle to room temperature, open and pour the contents into the separatory filter. Approximately 200 ml of a 2N hydrochloric acid solution is added to the separation filter. The mixture is extracted three times with 150 ml of diethyl ether. The extracts are combined and washed successively with 200 ml of 2N hydrochloric acid solution, 200 ml of saturated aqueous sodium chloride solution, and 200 ml of 2N sodium hydroxide solution. The washed extract is dried over anhydrous magnesium sulfate and filtered. The solvent is evaporated under reduced pressure to give an oil. The above mentioned reaction is carried out six more times. From the seven experiments, the residual oil was combined and column chromatography on silica gel using toluene as eluent to give a yellow oil. This oil is dissolved in 125 ml of methylcyclohexane and the solution is placed in the freezer for approximately 18 hours. The resulting crystals were collected by filtration to give 20.7 g of 2,2,3,3-tetrafluoro-5-nitrobenzofuran. The filtrate is evaporated under reduced pressure leaving oil. This oil is distilled off under reduced pressure to further give 3.0 g (boiling point: 75 ° C./0.2 mmHg). 2.15 g (0.011 mol) of 2,2,3,3-tetrafluoro-5-nitrobenzene was hydrogenated with a catalytic amount of platinum oxide (0.25 g) in 150 ml of methanol to yield 5-amino-2,2,3,3-tetrafluoro 2.15 g of robenzofuran are obtained.

톨루엔 109ml중의 5-아미노-2,2,3,3-테트라플루오로벤조푸란 0.75g(0.0036몰)의 용액을 톨루엔 중의 20% 포스겐 8.0ml의 교반된 용액에 적가한다. 적가가 끝난후 혼합물을 2시간 동안 환류 온도로 가열한다. 혼합물을 냉각하고 용매를 감압하에 증발시켜 제거하면 잔사가 남는다. 이 잔사를 디에틸 에테르 15ml에 용해하고, 디에틸 에테르 100ml중의 3-(4-디플루오로메톡시페닐)-4-페닐피라졸린 1.04g(0.0036몰) 및 트리에틸아민 3방울의 교반된 용액에 가한다. 첨가가 끝나면 혼합물을 1시간 동안 환류 가열한 다음 실온으로 냉각시키고 대략 18시간 동안 교반한다. 감압하에 증발시켜 반응 혼합물로 부터 용매를 제거하면 고체 잔사가 남는다. 에탄올로 부터 재결정하면 N-(2,3-디하이드로-2,2,3,3-테트라플루오로벤조푸란-5-일)-3-(4-디플루오로메톡시페닐)-4-페닐피라졸린-1-카복스아미드 0.99g이 수득된다. 융점 : 155 내지 159℃A solution of 0.75 g (0.0036 mol) of 5-amino-2,2,3,3-tetrafluorobenzofuran in 109 ml of toluene is added dropwise to a stirred solution of 8.0 ml of 20% phosgene in toluene. After the addition is completed, the mixture is heated to reflux for 2 hours. Cool the mixture and remove the solvent by evaporation under reduced pressure leaving a residue. The residue was dissolved in 15 ml of diethyl ether, and stirred in a stirred solution of 1.04 g (0.0036 mol) of 3- (4-difluoromethoxyphenyl) -4-phenylpyrazoline and 3 drops of triethylamine in 100 ml of diethyl ether. Add. At the end of the addition, the mixture is heated to reflux for 1 hour, then cooled to room temperature and stirred for approximately 18 hours. Evaporation under reduced pressure to remove solvent from the reaction mixture leaves a solid residue. Recrystallization from ethanol results in N- (2,3-dihydro-2,2,3,3-tetrafluorobenzofuran-5-yl) -3- (4-difluoromethoxyphenyl) -4-phenylpyra 0.99 g of sleepy-1-carboxamide is obtained. Melting Point: 155-159 ℃

원소분석 :Elemental Analysis:

계 산 치 : C 58.58 ; H 3.29Calculated: C 58.58; H 3.29

실 측 치 : C 57.81 ; H 3.75Found: C 57.81; H 3.75

nmr : 8.16ppmnmr: 8.16ppm

[실시예 49]Example 49

3,4-비스(4-클로로페닐)-N-(2,2디플루오로-1,3-벤조디옥솔-5-일)피라졸린-1-카보스아미드3,4-bis (4-chlorophenyl) -N- (2,2difluoro-1,3-benzodioxol-5-yl) pyrazoline-1-carbosamide

테트라하이드로푸란 80ml중의 5-아미노-2,2-디플루오로-1,3-벤조디옥솔(문헌에 기술된 방법에 의해 제조) 1.18g(0.0068몰)의 용액을 톨루엔중의 20% 포스겐 24ml의 냉(5°내지 10℃)용액을 적가한다. 적가가 끝난후, 혼합물을 2℃에서 1시간 동안 교반한 다음 2시간 동안 환류 온도에서 교반한다. 감압하에 용매를 증발시켜 액상 잔사 1.4g을 얻는다. 깨끗한 반응 플라스크중에서, 상기 잔사 0.68g을 디에틸 에테르 20ml중의 3,4-비스(4-클로로페닐)피라졸린 0.93g(0.0032몰) 침 트리에틸아민 3적의 교반된 용액에 서서히 가한다. 첨가가 끝난후 혼합물을 실온에서 대략 18시간 동안 교반한다. 반응 혼합물에는 소량의고체가 존재하는데, 여과하여 이를 제거한다. 여액을 감압하에 증발시키면 잔사가 남는다. 이 잔사를 n-헵탄 : 에틸 아세테이트(1 : 1)를 용출제로 사용하여 실리카겔상에서 칼럼 크로마토그라피하여 정제하면 융점 150 내지 155℃의 3,4-비스(4-클로로페닐)-N(2,2-디플루오로-1,3-벤조디옥솔-5-일)-피라졸린-1-카복스아미드 1.3g이 수득된다.A solution of 1.18 g (0.0068 mol) of 5-amino-2,2-difluoro-1,3-benzodioxol (prepared by the method described in the literature) in 80 ml of tetrahydrofuran was added to 24 ml of 20% phosgene in toluene. Cold (5 ° to 10 ° C) solution is added dropwise. After completion of the dropwise addition, the mixture is stirred at 2 ° C. for 1 hour and then at reflux temperature for 2 hours. The solvent is evaporated under reduced pressure to give 1.4 g of liquid residue. In a clean reaction flask, 0.68 g of the residue was slowly added to a stirred solution of 0.93 g (0.0032 mol) saliva triethylamine 3,4-bis (4-chlorophenyl) pyrazoline in 20 ml of diethyl ether. After the addition is complete the mixture is stirred at room temperature for approximately 18 hours. A small amount of solids is present in the reaction mixture, which is filtered off. The filtrate is evaporated under reduced pressure leaving a residue. The residue was purified by column chromatography on silica gel using n-heptane: ethyl acetate (1: 1) as eluent. 3,4-bis (4-chlorophenyl) -N (2,2) having a melting point of 150 to 155 占 폚. 1.3 g of -difluoro-1,3-benzodioxol-5-yl) -pyrazoline-1-carboxamide are obtained.

원소분석 :Elemental Analysis:

계 산 치 : C 56.34 ; H 3.08Calculated: C 56.34; H 3.08

실 측 치 : C 57.16 ; H 2.89Found: C 57.16; H 2.89

nmr : 8.10ppmnmr: 8.10ppm

실시예 50의 화합물은 유사하게 제조된다.The compound of Example 50 is prepared similarly.

[실시예 50]Example 50

N-(2,2-디플루오로-1,3-벤조디옥솔-5-일)-3-(4-디플루오로메톡시페닐)-4-페닐피라졸린-1-카복스아미드, 융점 : 135 내지 138, 8.10ppmN- (2,2-difluoro-1,3-benzodioxol-5-yl) -3- (4-difluoromethoxyphenyl) -4-phenylpyrazolin-1-carboxamide, Melting point: 135 to 138, 8.10 ppm

[실시예 51]Example 51

3-(4-플루오로페닐)-N-(4-페녹시페닐)-4-페닐피라졸린-1-카복스아미드, 융점 : 187 내지 191, 8.10ppm3- (4-fluorophenyl) -N- (4-phenoxyphenyl) -4-phenylpyrazoline-1-carboxamide, Melting Point: 187-191, 8.10 ppm

[실시예 52]Example 52

3-(4-플루오로메톡시페닐)-N-(4-페녹시페닐)-4-페닐피라졸린-1-카복스아미드, 융점 : 139 내지 144, 8.10ppm3- (4-fluoromethoxyphenyl) -N- (4-phenoxyphenyl) -4-phenylpyrazoline-1-carboxamide, Melting Point: 139 to 144, 8.10 ppm

[실시예 53]Example 53

3-(4-클로로페닐)-N-[4-(4-클로로페녹시)페닐]-4-페닐피라졸린-1-카복스아미드, 융점 : 170 내지 174, 8.10ppm3- (4-chlorophenyl) -N- [4- (4-chlorophenoxy) phenyl] -4-phenylpyrazoline-1-carboxamide, Melting Point: 170 to 174, 8.10 ppm

[실시예 54]Example 54

3-(4-클로로페닐)-N-[4-(4-니트로페녹시)페닐]-4-페닐피라졸린-1-카복스아미드, 융점 : 187 내지 189, 8.30ppm3- (4-chlorophenyl) -N- [4- (4-nitrophenoxy) phenyl] -4-phenylpyrazoline-1-carboxamide, Melting Point: 187-189, 8.30 ppm

[실시예 55]Example 55

3-(4-클로로페닐)-N-[4-(4-메톡시페녹시)페닐]-4-페닐피라졸린-1-카복스아미드, 융점 : 159 내지 160, 8.70ppm3- (4-chlorophenyl) -N- [4- (4-methoxyphenoxy) phenyl] -4-phenylpyrazoline-1-carboxamide, Melting Point: 159 to 160, 8.70 ppm

[실시예 56]Example 56

3-(4-클로로페닐)-N-[4-(4-디플루오로메톡시페녹시)페닐]-4-페닐피라졸린-1-카복스아미드, 융점 : 181 내지 184, 8.07ppm3- (4-chlorophenyl) -N- [4- (4-difluoromethoxyphenoxy) phenyl] -4-phenylpyrazoline-1-carboxamide, Melting point: 181 to 184, 8.07 ppm

[실시예 57]Example 57

N-[4-(4-클로로페녹시)페닐]-3-(4-트리플루오로메톡시페닐)-4-페닐피라졸린-1-카복스아미드, 융점 : 132-134, 8.16ppmN- [4- (4-chlorophenoxy) phenyl] -3- (4-trifluoromethoxyphenyl) -4-phenylpyrazoline-1-carboxamide, Melting point: 132-134, 8.16 ppm

[실시예 58]Example 58

N-[4-(4-클로로페녹시)페닐]-4-페닐-3-[4-(2-프로피닐옥시)페닐]피라졸린-1-카복스아미드, 융점 : 160-164, 8.13ppmN- [4- (4-chlorophenoxy) phenyl] -4-phenyl-3- [4- (2-propynyloxy) phenyl] pyrazoline-1-carboxamide, Melting point: 160-164, 8.13 ppm

[실시예 59]Example 59

3-(1,3-벤조디옥솔-5-일)-N-(4-페녹시페닐)-4-페닐피라졸린-1-카복스아미드, 융점 : 220-223, 8.06ppm3- (1,3-benzodioxol-5-yl) -N- (4-phenoxyphenyl) -4-phenylpyrazoline-1-carboxamide, Melting Point: 220-223, 8.06ppm

[실시예 60]Example 60

4-(4-클로로페닐)-N-(4-페녹시페닐)-3-페닐피라졸린-1-카복스아미드, 융점 : 153-155, 8.16ppm4- (4-Chlorophenyl) -N- (4-phenoxyphenyl) -3-phenylpyrazoline-1-carboxamide, Melting Point: 153-155, 8.16ppm

[실시예 61]Example 61

3,4-비스(4-플루오로페닐)-N-(4-페녹시페닐)피라졸린-1-카복스아미드, 융점 : 194-198, 8.16ppm3,4-bis (4-fluorophenyl) -N- (4-phenoxyphenyl) pyrazoline-1-carboxamide, Melting point: 194-198, 8.16 ppm

[실시예 62]Example 62

N-[4-(2-클로로페녹시)페닐]-3,4-비스(4-클로로페닐)-피라졸린-1-카복스아미드, 융점 : 182-186, 8.10ppmN- [4- (2-chlorophenoxy) phenyl] -3,4-bis (4-chlorophenyl) -pyrazoline-1-carboxamide, Melting point: 182-186, 8.10 ppm

[실시예 63]Example 63

3,4-비스(4-클로로페닐)-N-[4-(4-메톡시페녹시)페닐]-피라졸린-1-카복스아미드, 8.20ppm3,4-bis (4-chlorophenyl) -N- [4- (4-methoxyphenoxy) phenyl] -pyrazoline-1-carboxamide, 8.20 ppm

[실시예 64]Example 64

3-(4-클로로페닐)-4-(4-플루오로페닐)-N-(4-페녹시페닐)-피라졸린-1-카복스아미드, 융점 : 178-179, 8.10ppm3- (4-Chlorophenyl) -4- (4-fluorophenyl) -N- (4-phenoxyphenyl) -pyrazoline-1-carboxamide, Melting point: 178-179, 8.10 ppm

[실시예 65]Example 65

N-[4-(4-클로로페녹시)페닐]-3-(4-클로로페닐)-4-(4-플루오로페닐)피라졸린-1-카복스아미드, 융점 : 143-145, 8.03ppmN- [4- (4-chlorophenoxy) phenyl] -3- (4-chlorophenyl) -4- (4-fluorophenyl) pyrazoline-1-carboxamide, Melting point: 143-145, 8.03 ppm

[실시예 66]Example 66

3-(4-클로로페닐)-4-(4-메틸페닐)-N-(4-페녹시페닐)-피라졸린-1-카복스아미드, 융점 : 165-168, 8.10ppm3- (4-Chlorophenyl) -4- (4-methylphenyl) -N- (4-phenoxyphenyl) -pyrazoline-1-carboxamide, Melting point: 165-168, 8.10 ppm

[실시예 67]Example 67

N-[4-(4-클로로페녹시)페닐]-3-(4-클로로페닐)-4-(4-메톡싶페닐)피라졸린-1-카복스아미드, 융점 : 169-173, 8.07ppmN- [4- (4-chlorophenoxy) phenyl] -3- (4-chlorophenyl) -4- (4-methokenphenyl) pyrazoline-1-carboxamide, Melting point: 169-173, 8.07 ppm

[실시예 68]Example 68

4-(4-플루오로페닐)-3-(4-메톡시페닐)-N-(4-페녹시페닐)-피라졸린-1-카복스아미드, 융점 : 184-187, 8.17ppm4- (4-Fluorophenyl) -3- (4-methoxyphenyl) -N- (4-phenoxyphenyl) -pyrazoline-1-carboxamide, Melting point: 184-187, 8.17 ppm

[실시예 69]Example 69

N-[4-(4-디플루오로메톡시페녹시)페닐]-3-(4-디플루오로메톡시페닐)-4-(4-플루오로페닐)피라졸린-1-카복스아미드, 8.10ppmN- [4- (4-difluoromethoxyphenoxy) phenyl] -3- (4-difluoromethoxyphenyl) -4- (4-fluorophenyl) pyrazoline-1-carboxamide, 8.10 ppm

[실시예 70]Example 70

N-[4-(4-클로로페녹시)페닐]-3-(4-클로로페닐)-4-페닐피라졸린-1-카복스아미드, 융점 : 179-183, 9.10ppmN- [4- (4-chlorophenoxy) phenyl] -3- (4-chlorophenyl) -4-phenylpyrazoline-1-carboxamide, Melting point: 179-183, 9.10 ppm

[실시예 71]Example 71

3-(4-디플루오로메톡시페닐)-N-(4-페녹시페닐)-4-페닐피라졸린-1-티오카복스아미드, 융점 : 132-136, 9.13ppm3- (4-Difluoromethoxyphenyl) -N- (4-phenoxyphenyl) -4-phenylpyrazoline-1-thiocarboxamide, Melting point: 132-136, 9.13 ppm

[실시예 72]Example 72

4-(4-클로로페닐)-N-(4-페녹시페닐)-3-페닐피라졸린-1-티오카복스아미드, 융점 : 131-133, 9.16ppm4- (4-Chlorophenyl) -N- (4-phenoxyphenyl) -3-phenylpyrazoline-1-thiocarboxamide, Melting point: 131-133, 9.16ppm

[실시예 73]Example 73

N-[4-(4-클로로페닐티오)페닐]-3,4-디페닐피라졸린-1-카복스아미드, 융점 : 186-190, 8.20ppmN- [4- (4-chlorophenylthio) phenyl] -3,4-diphenylpyrazoline-1-carboxamide, Melting point: 186-190, 8.20 ppm

[실시예 74]Example 74

3-(4-클로로페닐)-N-[4-(4-클로로페닐티오)페닐]-4-페닐피라졸린-1-카복스아미드, 융점 : 178-181, 8.23ppm3- (4-chlorophenyl) -N- [4- (4-chlorophenylthio) phenyl] -4-phenylpyrazoline-1-carboxamide, Melting Point: 178-181, 8.23 ppm

[실시예 75]Example 75

3-(4-디플루오로메톡시페닐)-4-페닐-N-(4-페닐티오페닐)-피라졸린-1-카복스아미드, 융점 : 135-140, 8.13ppm3- (4-Difluoromethoxyphenyl) -4-phenyl-N- (4-phenylthiophenyl) -pyrazoline-1-carboxamide, Melting point: 135-140, 8.13 ppm

[실시예 76]Example 76

3,4-비스(4-클로로페닐)-N-[4-(4-플루오로페닐티오)-페닐]피라졸린-1-카복스아미드, 융점 : 171-175, 8.20ppm3,4-bis (4-chlorophenyl) -N- [4- (4-fluorophenylthio) -phenyl] pyrazoline-1-carboxamide, Melting point: 171-175, 8.20 ppm

[실시예 77]Example 77

3,4-비스(4-클로로페닐)-N-[4-(4-클로로페닐티오)-페닐]피라졸린-1-카복스아미드, 융점 : 151-156, 8.13ppm3,4-bis (4-chlorophenyl) -N- [4- (4-chlorophenylthio) -phenyl] pyrazoline-1-carboxamide, Melting point: 151-156, 8.13 ppm

[실시예 78]Example 78

3,4-비스(4-클로로페닐)-N-[4-(3-클로페녹시)페닐]피라졸린-1-카복스아미드, 융점 : 135-140, 9.20ppm(DMSO-d6)3,4-bis (4-chlorophenyl) -N- [4- (3-clophenoxy) phenyl] pyrazoline-1-carboxamide, Melting point: 135-140, 9.20 ppm (DMSO-d 6 )

[실시예 79]Example 79

3-(4-메톡시페닐)-N-(4-페녹시페닐)-4-페닐피라졸린-1-카복스아미드, 융점 : 188-192, 8.46ppm(CDCl3/DMSO-d6)3- (4-methoxyphenyl) -N- (4-phenoxyphenyl) -4-phenylpyrazolin-1-carboxamide, Melting Point: 188-192, 8.46ppm (CDCl 3 / DMSO-d 6 )

[실시예 80]Example 80

3-[4-(2-프로피닐옥시)페닐]-N-(4-페녹시페닐)-4-페닐피라졸린-1-카복스아미드, 융점 : 121-126, 8.10ppm3- [4- (2-propynyloxy) phenyl] -N- (4-phenoxyphenyl) -4-phenylpyrazoline-1-carboxamide, Melting Point: 121-126, 8.10 ppm

[실시예 81]Example 81

3-(4-클로로페닐)-N-(2,3-디하이드로벤조푸란-5-일)-4-페닐피라졸린-1-카복스아미드, 융점 : 155-158, 7.93ppm3- (4-chlorophenyl) -N- (2,3-dihydrobenzofuran-5-yl) -4-phenylpyrazoline-1-carboxamide, Melting Point: 155-158, 7.93ppm

[실시예 82]Example 82

3-(4-디플루오로메톡시페닐)-N-(2,3-디하이드로벤조푸란-5-일)-4-페닐피라졸린-1-카복스아미드, 7.93ppm3- (4-difluoromethoxyphenyl) -N- (2,3-dihydrobenzofuran-5-yl) -4-phenylpyrazoline-1-carboxamide, 7.93 ppm

[실시예 83]Example 83

3,4-비스(4-클로로페닐)-N-(2,3-디하이드로벤조푸란-5-일)피라졸린-1-카복스아미드, 융점 : 214-216, 7.93ppm3,4-bis (4-chlorophenyl) -N- (2,3-dihydrobenzofuran-5-yl) pyrazoline-1-carboxamide, Melting point: 214-216, 7.93 ppm

[실시예 84]Example 84

3-(4-플루오로페닐)-N-(2,3-디하이드로-2,2-디메틸벤조푸란-5-일)-4-페닐피라졸린-1-카복스아미드, 융점 : 156-160, 7.93ppm3- (4-fluorophenyl) -N- (2,3-dihydro-2,2-dimethylbenzofuran-5-yl) -4-phenylpyrazolin-1-carboxamide, Melting point: 156-160 , 7.93ppm

[실시예 85]Example 85

3-(4-메톡시페닐)-N-(2,3-디하이드로-2,2-디메틸벤조푸란-5-일)-4-페닐피라졸린-1-카복스아미드, 융점 : 164-169, 8.00ppm3- (4-methoxyphenyl) -N- (2,3-dihydro-2,2-dimethylbenzofuran-5-yl) -4-phenylpyrazolin-1-carboxamide, Melting point: 164-169 , 8.00ppm

[실시예 86]Example 86

3-(4-트리플루오로메톡시페닐)-N-(2,3-디하이드로-2,2-디메틸벤조푸란-5-일)-4-페닐피라졸린-1-카복스아미드, 융점 : 81-83, 7.98ppm3- (4-Trifluoromethoxyphenyl) -N- (2,3-dihydro-2,2-dimethylbenzofuran-5-yl) -4-phenylpyrazoline-1-carboxamide, Melting point: 81 -83, 7.98 ppm

[실시예 87]Example 87

N-(2,3-디하이드로-2,2-디메틸벤조푸란-5-일)-4-페닐-3-[4-(2-프로피닐옥시)페닐]피라졸린-1-카복스아미드, 융점 : 175-179, 8.00ppmN- (2,3-dihydro-2,2-dimethylbenzofuran-5-yl) -4-phenyl-3- [4- (2-propynyloxy) phenyl] pyrazoline-1-carboxamide, Melting Point: 175-179, 8.00ppm

[실시예 88]Example 88

3-(1,3-벤조디옥솔-5-일)-N-(2,3-디하이드로-2,2-디메틸벤조푸란-5-일)-4-페닐피라졸린-1-카복스아미드, 융점 : 223-227, 8.90ppm(DMSO-d6)3- (1,3-benzodioxol-5-yl) -N- (2,3-dihydro-2,2-dimethylbenzofuran-5-yl) -4-phenylpyrazoline-1-carboxamide Melting point: 223-227, 8.90 ppm (DMSO-d 6 )

[실시예 89]Example 89

4-(4-클로로페닐)-N-(2,3-디하이드로-2,2-디메틸벤조푸란-5-일)-3-페닐피라졸린-1-카복스아미드, 8.00ppm4- (4-Chlorophenyl) -N- (2,3-dihydro-2,2-dimethylbenzofuran-5-yl) -3-phenylpyrazoline-1-carboxamide, 8.00 ppm

[실시예 90]Example 90

3,4-비스(4-플루오로페닐)-N-(2,3-디하이드로-2,2-디메틸벤조푸란-5-일)피라졸린-1-카복스아미드, 융점 : 161-166, 7.93ppm3,4-bis (4-fluorophenyl) -N- (2,3-dihydro-2,2-dimethylbenzofuran-5-yl) pyrazolin-1-carboxamide, Melting point: 161-166, 7.93ppm

[실시예 91]Example 91

3-(4-클로로페닐)-4-(4-플루오로페닐)-N-(2,3-디하이드로-2,2-디메틸벤조푸란-5-일)피라졸린-1-카복스아미드, 융점 : 169-171, 7.96ppm3- (4-chlorophenyl) -4- (4-fluorophenyl) -N- (2,3-dihydro-2,2-dimethylbenzofuran-5-yl) pyrazoline-1-carboxamide, Melting Point: 169-171, 7.96ppm

[실시예 92]Example 92

3-(4-클로로페닐)-4-(4-메틸페닐)-N-(2,3-디하이드로-2,2-디메틸벤조푸란-5-일)피라졸린-1-카복스아미드, 융점 : 137-139, 7.96ppm3- (4-Chlorophenyl) -4- (4-methylphenyl) -N- (2,3-dihydro-2,2-dimethylbenzofuran-5-yl) pyrazolin-1-carboxamide, Melting point: 137-139, 7.96ppm

[실시예 93]Example 93

3-(4-클로로페닐)-4-(4-메톡시페닐)-N-(2,3-디하이드로-2,2-디메틸벤조푸란-5-일)피라졸린-1-카복스아미드, 융점 : 182-186, 7.93ppm3- (4-chlorophenyl) -4- (4-methoxyphenyl) -N- (2,3-dihydro-2,2-dimethylbenzofuran-5-yl) pyrazoline-1-carboxamide, Melting Point: 182-186, 7.93ppm

[실시예 94]Example 94

4-(4-플루오로페닐)-N-(2,3-디하이드로-2,2-디메틸벤조푸란-5-일)-3-(4-메톡시페닐)피라졸린-1-카복스아미드, 융점 : 179-182, 7.93ppm4- (4-fluorophenyl) -N- (2,3-dihydro-2,2-dimethylbenzofuran-5-yl) -3- (4-methoxyphenyl) pyrazolin-1-carboxamide Melting Point: 179-182, 7.93ppm

[실시예 95]Example 95

4-(4-클로로페닐)-N-(2,3-디하이드로-2,2-디메틸벤조푸란-5-일)-3-(4-메톡시페닐)피라졸린-1-카복스아미드, 융점 : 157-160, 7.96ppm4- (4-chlorophenyl) -N- (2,3-dihydro-2,2-dimethylbenzofuran-5-yl) -3- (4-methoxyphenyl) pyrazolin-1-carboxamide, Melting Point: 157-160, 7.96ppm

[실시예 96]Example 96

3-(4-디플루오로메톡시페닐)-4-(4-플루오로페닐)-N-(2,3-디하이드로-2,2-디메틸벤조푸란-5-일)피라졸린-1-카복스아미드, 융점 : 169-172, 7.93ppm3- (4-difluoromethoxyphenyl) -4- (4-fluorophenyl) -N- (2,3-dihydro-2,2-dimethylbenzofuran-5-yl) pyrazoline-1-car Boxamide, Melting Point: 169-172, 7.93ppm

[실시예 97]Example 97

4-(4-클로로페닐)-3-(4-디플루오로메톡시페닐)-N-(2,3-디하이드로-2,2-디메틸벤조푸란-5-일)피라졸린-1-카복스아미드, 융점 : 90-95, 7.93ppm4- (4-chlorophenyl) -3- (4-difluoromethoxyphenyl) -N- (2,3-dihydro-2,2-dimethylbenzofuran-5-yl) pyrazoline-1-carbox Amide, melting point: 90-95, 7.93ppm

[실시예 98]Example 98

3-(4-디플루오로메톡시페닐)-N-(2,3-디하이드로-2,2,3,3-테트라플루오로벤조푸란-6-일)-4-페닐피라졸린-1-카복스아미드, 융점 : 152-157, 8.33ppm3- (4-difluoromethoxyphenyl) -N- (2,3-dihydro-2,2,3,3-tetrafluorobenzofuran-6-yl) -4-phenylpyrazoline-1-car Boxamide, Melting Point: 152-157, 8.33ppm

[실시예 99]Example 99

3-(4-디플루오로메톡시페닐)-4-(4-플루오로페닐)-N-(2,3-디하이드로-2,2,3,3-테트라플루오로벤조푸란-6-일)피라졸린-1-카복스아미드, 융점 : 110-114, 8.33ppm3- (4-difluoromethoxyphenyl) -4- (4-fluorophenyl) -N- (2,3-dihydro-2,2,3,3-tetrafluorobenzofuran-6-yl) Pyrazoline-1-carboxamide, Melting Point: 110-114, 8.33ppm

[실시예 100]Example 100

3-(4-디플루오로메톡시페닐)-4-(4-플루오로페닐)-N-(2,3-디하이드로-2,2,3,3-테트라플루오로벤조푸란-5-일)피라졸린-1-카복스아미드, 융점 : 155-159, 8.20ppm3- (4-difluoromethoxyphenyl) -4- (4-fluorophenyl) -N- (2,3-dihydro-2,2,3,3-tetrafluorobenzofuran-5-yl) Pyrazoline-1-carboxamide, Melting Point: 155-159, 8.20ppm

[실시예 101]Example 101

3-(4-클로로페닐)-N-(2,2-디메틸-1,3-벤조디옥솔-5-일)-4-페닐피라졸린-1-카복스아미드, 융점 : 182-186, 7.96ppm3- (4-Chlorophenyl) -N- (2,2-dimethyl-1,3-benzodioxol-5-yl) -4-phenylpyrazolin-1-carboxamide, Melting point: 182-186, 7.96 ppm

[실시예 102]Example 102

3-(4-디플루오로메톡시페닐)-N-(2,2-디메틸-1,3-벤조디옥솔-5-일)-4-페닐피라졸린-1-카복스아미드, 융점 : 148-150, 7.93ppm3- (4-Difluoromethoxyphenyl) -N- (2,2-dimethyl-1,3-benzodioxol-5-yl) -4-phenylpyrazolin-1-carboxamide, Melting point: 148- 150, 7.93ppm

[실시예 103]Example 103

3,4-비스(4-클로로페닐)-N-(2,2-디메틸-1,3-벤조디옥솔-5-일)-피라졸린-1-카복스아미드, 융점 : 168-169, 7.93ppm3,4-bis (4-chlorophenyl) -N- (2,2-dimethyl-1,3-benzodioxol-5-yl) -pyrazoline-1-carboxamide, melting point: 168-169, 7.93 ppm

[실시예 104]Example 104

N-(1,4-벤조디옥산-5-일)-3-(4-디플루오로메톡시페닐)-4-페닐피라졸린-1-카복스아미드, 7.93ppmN- (1,4-benzodioxan-5-yl) -3- (4-difluoromethoxyphenyl) -4-phenylpyrazoline-1-carboxamide, 7.93 ppm

[실시예 105]Example 105

N-(2,2-디플루오로-1,3-벤조디옥솔-5-일)-3-(4-디플루오로메톡시페닐)-N-메틸-4-페닐피라졸린-1-카복스아미드, 융점 : 110-114N- (2,2-difluoro-1,3-benzodioxol-5-yl) -3- (4-difluoromethoxyphenyl) -N-methyl-4-phenylpyrazoline-1-carbox Amide, melting point: 110-114

[실시예 106]Example 106

4-(1,3-벤조디옥솔-5-일)-N-(4-페녹시페닐)-3-페닐-피라졸린-1-카복스아미드, 융점 : 195-197, 8.03ppm4- (1,3-benzodioxol-5-yl) -N- (4-phenoxyphenyl) -3-phenyl-pyrazoline-1-carboxamide, Melting point: 195-197, 8.03 ppm

[실시예 107]Example 107

3-(4-클로로페닐)-N-[4-[4-(1,1-디메틸에틸)-페녹시]-페닐]-4-페닐피라졸린-1-카복스아미드, 융점 : 192.5-194, 8.03ppm3- (4-Chlorophenyl) -N- [4- [4- (1,1-dimethylethyl) -phenoxy] -phenyl] -4-phenylpyrazolin-1-carboxamide, Melting point: 192.5-194 , 8.03 ppm

[실시예 108]Example 108

3-(4-클로로페닐)-4-(4-플루오로페닐)-N-[4-(4-메틸페녹시)페닐]피라졸린-1-카복스아미드, 융점 : 162-164, 8.03ppm3- (4-chlorophenyl) -4- (4-fluorophenyl) -N- [4- (4-methylphenoxy) phenyl] pyrazoline-1-carboxamide, Melting point: 162-164, 8.03 ppm

[실시예 109]Example 109

3-(4-클로로페닐)-4-(4-플루오로페닐)-N-[4-[4-(1,1-디메틸에틸)페녹시]페닐]피라졸린-1-카복스아미드, 융점 : 188-198, 8.03ppm3- (4-chlorophenyl) -4- (4-fluorophenyl) -N- [4- [4- (1,1-dimethylethyl) phenoxy] phenyl] pyrazoline-1-carboxamide, melting point : 188-198, 8.03ppm

[실시예 110]Example 110

3-(4-클로로페닐)-N-[4-[4-(1-메틸에틸)페녹시]-페닐]-4-페닐피라졸린-1-카복스아미드, 융점 : 181-182., 8.06ppm3- (4-Chlorophenyl) -N- [4- [4- (1-methylethyl) phenoxy] -phenyl] -4-phenylpyrazoline-1-carboxamide, Melting point: 181-182., 8.06 ppm

[실시예 111]Example 111

3-(4-클로로페닐)-4-(4-플루오로페닐)-N-[4-[4-(1-메틸에틸)페녹시]페닐]피라졸린-1-카복스아미드, 융점 : 186-187, 8.60ppm(CDCl3/DMSO-d6)3- (4-Chlorophenyl) -4- (4-fluorophenyl) -N- [4- [4- (1-methylethyl) phenoxy] phenyl] pyrazoline-1-carboxamide, Melting point: 186 -187, 8.60 ppm (CDCl 3 / DMSO-d 6 )

[실시예 112]Example 112

3-(4-클로로페닐)-N-[4-(4-메틸페녹시)페닐-4-페닐]피라졸린-1-카복스아미드, 융점 : 150-151, 8.06ppm3- (4-chlorophenyl) -N- [4- (4-methylphenoxy) phenyl-4-phenyl] pyrazoline-1-carboxamide, Melting Point: 150-151, 8.06ppm

[실시예 113]Example 113

3-(4-클로로페닐)-N-[4-[4-(1-메틸에톡시)페녹시]-페닐]-4-페닐피라졸린-1-카복스아미드, 융점 : 158-160.5, 8.06ppm3- (4-chlorophenyl) -N- [4- [4- (1-methylethoxy) phenoxy] -phenyl] -4-phenylpyrazoline-1-carboxamide, melting point: 158-160.5, 8.06 ppm

[실시예 114]Example 114

3-(4-클로로페닐)-4-(4-플루오로페닐)-N-[4-[4-(1-메틸에톡시)페녹시]페닐]피라졸린-1-카복스아미드, 융점 : 213-216, 8.66ppm(CDCl3/DMSO-d6)3- (4-Chlorophenyl) -4- (4-fluorophenyl) -N- [4- [4- (1-methylethoxy) phenoxy] phenyl] pyrazoline-1-carboxamide, Melting point: 213-216, 8.66 ppm (CDCl 3 / DMSO-d 6 )

[실시예 115]Example 115

3,4-비스(4-플루오로페닐)-N-[4-[4-(1-메틸에톡시)-페녹시]페닐]피라졸린-1-카복스아미드, 융점 : 134-136.5, 8.06ppm3,4-bis (4-fluorophenyl) -N- [4- [4- (1-methylethoxy) -phenoxy] phenyl] pyrazoline-1-carboxamide, Melting point: 134-136.5, 8.06 ppm

[실시예 116]Example 116

3,4-비스(4-플루오로페닐)-N-[4-(4-클로로페녹시)-페닐]-피라졸린-1-카복스아미드, 융점 : 197-198.5, 8.70ppm3,4-bis (4-fluorophenyl) -N- [4- (4-chlorophenoxy) -phenyl] -pyrazoline-1-carboxamide, melting point: 197-198.5, 8.70 ppm

[실시예 117]Example 117

3,4-비스(4-플루오로페닐)-N-[4-[4-(1,1-디메틸에틸)-페녹시]페닐]피라졸린-1-카복스아미드, 융점 : 1189-192, 8.70ppm(CDCl3/DMSO-d6)3,4-bis (4-fluorophenyl) -N- [4- [4- (1,1-dimethylethyl) -phenoxy] phenyl] pyrazoline-1-carboxamide, Melting point: 1189-192, 8.70 ppm (CDCl 3 / DMSO-d 6 )

[실시예 118]Example 118

3,4-비스(4-플루오로페닐)-N-[4-(4-시아노페녹시)-페닐]-피라졸린-1-카복스아미드, 융점 : 198-200, 8.13ppm3,4-bis (4-fluorophenyl) -N- [4- (4-cyanophenoxy) -phenyl] -pyrazoline-1-carboxamide, melting point: 198-200, 8.13 ppm

[실시예 119]Example 119

3,4-비스(4-플루오로페닐)-N-[4-[4-(N,N-디메틸아미노)페녹시]페닐]피라졸린-1-카복스아미드, 융점 : 148-150, 8.02ppm3,4-bis (4-fluorophenyl) -N- [4- [4- (N, N-dimethylamino) phenoxy] phenyl] pyrazoline-1-carboxamide, Melting point: 148-150, 8.02 ppm

[실시예 120]Example 120

3-(4-클로로페닐)-N-[4-(4-시아노페녹시)페닐]-4-페닐피라졸린-1-카복스아미드, 융점 : 170-172, 8.16ppm3- (4-Chlorophenyl) -N- [4- (4-cyanophenoxy) phenyl] -4-phenylpyrazoline-1-carboxamide, Melting point: 170-172, 8.16 ppm

[실시예 121]Example 121

N-(1,4-벤도디옥산-6-일)-4-(4-클로로페닐)-3-(4-디플루오로메톡시페닐)피라졸린-1-카복스아미드, 융점 : 124-128, 7.93ppmN- (1,4-bendodioxan-6-yl) -4- (4-chlorophenyl) -3- (4-difluoromethoxyphenyl) pyrazolin-1-carboxamide, Melting point: 124- 128, 7.93 ppm

[실시예 122]Example 122

3,4-비스(4-클로로페닐)-N-(2,3-디하이드로-2,2-디메틸벤조푸란-5-일)-N-메틸피라졸린-1-카복스아미드, 융점 : 150-1553,4-bis (4-chlorophenyl) -N- (2,3-dihydro-2,2-dimethylbenzofuran-5-yl) -N-methylpyrazoline-1-carboxamide, melting point: 150 -155

[실시예 123]Example 123

N-(2,2-디플루오로-1,3-벤조디옥솔-5-일)-3,4-(디페닐피라졸린)-1-카복스아미드, 융점 : 214-216, 8.83ppm(CDCl3/DMSO-d6)N- (2,2-difluoro-1,3-benzodioxol-5-yl) -3,4- (diphenylpyrazolin) -1-carboxamide, Melting point: 214-216, 8.83 ppm ( CDCl 3 / DMSO-d 6 )

[실시예 124]Example 124

N-(2,2-디플루오로-1,3-벤조디옥솔-5-일)-3,4-비스(4-플루오로페닐)피라졸린-1-카복스아미드, 융점 : 178-180, 8.10ppmN- (2,2-difluoro-1,3-benzodioxol-5-yl) -3,4-bis (4-fluorophenyl) pyrazolin-1-carboxamide, Melting point: 178-180 , 8.10 ppm

[실시예 125]Example 125

3-(4-클로로페닐)-N-(2,2-디플루오로-1,3-벤조디옥솔-5-일)-4-(4-플루오로페닐)피라졸린-1-카복스아미드, 융점 : 147-151, 8.06ppm3- (4-chlorophenyl) -N- (2,2-difluoro-1,3-benzodioxol-5-yl) -4- (4-fluorophenyl) pyrazoline-1-carboxamide Melting Point: 147-151, 8.06ppm

[실시예 126]Example 126

3-(4-디플루오로메톡시페닐)-N-(2,3-디하이드로-2,2,3,3-테트라플루오로벤조푸란-5-일)-N-메틸-4-페닐피라졸린-1-카복스아미드3- (4-difluoromethoxyphenyl) -N- (2,3-dihydro-2,2,3,3-tetrafluorobenzofuran-5-yl) -N-methyl-4-phenylpyrazoline -1-carboxamide

[실시예 127]Example 127

3-(4-클로로페닐)-4-(4-디플루오로메톡시페닐)-N-(2,3-디하이드로-2,2-디메틸벤조푸란-5-일)피라졸린-1-카복스아미드, 융점 : 155-159, 7.96ppm3- (4-chlorophenyl) -4- (4-difluoromethoxyphenyl) -N- (2,3-dihydro-2,2-dimethylbenzofuran-5-yl) pyrazoline-1-carbox Amide, melting point: 155-159, 7.96ppm

[실시예 128]Example 128

3-(4-디플루오로메톡시페닐)-N-(2,3-디하이드로-2,2-디플루오로벤조푸란-5-일)-N-메틸-4-페닐피라졸린-1-카복스아미드3- (4-Difluoromethoxyphenyl) -N- (2,3-dihydro-2,2-difluorobenzofuran-5-yl) -N-methyl-4-phenylpyrazoline-1-car Voxamide

[실시예 129]Example 129

4-(4-클로로페닐)-N-(2,2-디플루오로-1,3-벤조디옥솔-5-일)-3-(4-디플루오로메톡시페닐)피라졸린-1-카복스아미드, 8.06ppm4- (4-chlorophenyl) -N- (2,2-difluoro-1,3-benzodioxol-5-yl) -3- (4-difluoromethoxyphenyl) pyrazoline-1-car Boxamide, 8.06ppm

[실시예 130]Example 130

4-(1,3-벤조디옥솔-5-일)-3-(4-클로로페닐)-N-[4-(4-플루오로메톡시페녹시)페닐]피라졸린-1-카복스아미드4- (1,3-benzodioxol-5-yl) -3- (4-chlorophenyl) -N- [4- (4-fluoromethoxyphenoxy) phenyl] pyrazoline-1-carboxamide

[실시예 131]Example 131

4-(1,3-벤조디옥솔-5-일)-N-[4-(4-클로로페녹시)-페닐]-3-(4-클로로페닐)피라졸린-1-카복스아미드4- (1,3-benzodioxol-5-yl) -N- [4- (4-chlorophenoxy) -phenyl] -3- (4-chlorophenyl) pyrazolin-1-carboxamide

[실시예 132]Example 132

4-(1,3-벤조디옥솔-5-일)-3-(4-클로로페닐)-N-(2,2-디플루오로-1,3-벤조디옥솔-5-일)피라졸린-1-카복스아미드4- (1,3-benzodioxol-5-yl) -3- (4-chlorophenyl) -N- (2,2-difluoro-1,3-benzodioxol-5-yl) pyrazoline -1-carboxamide

[실시예 133]Example 133

4-(1,3-벤조디옥솔-5-일)-3-(4-클로로페닐)-N-(2,3-디하이드로-2,2,3,3-테트라플루오로벤조푸란-5-일)피라졸린-1-카복스아미드4- (1,3-benzodioxol-5-yl) -3- (4-chlorophenyl) -N- (2,3-dihydro-2,2,3,3-tetrafluorobenzofuran-5 -Yl) pyrazoline-1-carboxamide

[실시예 134]Example 134

4-(1,3-벤조디옥솔-5-일)-3-(4-클로로페닐)-N-(2,3-디하이드로-2,2-디메틸벤조푸란-5-일)피라졸린-1-카복스아미드4- (1,3-benzodioxol-5-yl) -3- (4-chlorophenyl) -N- (2,3-dihydro-2,2-dimethylbenzofuran-5-yl) pyrazoline- 1-carboxamide

[실시예 135]Example 135

4-(1,3-벤조디옥솔-5-일)-N-[4-(4-디플루오로메톡시페녹시)페닐]-3-(4-디플루오로메톡시페닐피라졸린-1-카복스아미드4- (1,3-benzodioxol-5-yl) -N- [4- (4-difluoromethoxyphenoxy) phenyl] -3- (4-difluoromethoxyphenylpyrazoline-1-car Voxamide

[실시예 136]Example 136

4-(1,3-벤조디옥솔-5-일)-N-[4-(4-클로로페녹시)페닐]-3-(4-디플루오로메톡시페닐)피라졸린-1-카복스아미드4- (1,3-benzodioxol-5-yl) -N- [4- (4-chlorophenoxy) phenyl] -3- (4-difluoromethoxyphenyl) pyrazoline-1-carboxamide

[실시예 137]Example 137

4-(1,3-벤조디옥솔-5-일)-N-(2,2-디플루오로-1,3-벤조디옥솔-5-일)-3-(4-디플루오로메톡시페닐)피라졸린-1-카복스아미드4- (1,3-benzodioxol-5-yl) -N- (2,2-difluoro-1,3-benzodioxol-5-yl) -3- (4-difluoromethoxyphenyl Pyrazoline-1-carboxamide

[실시예 138]Example 138

4-(1,3-벤조디옥솔-5-일)-3-(4-디플루오로메톡시페닐)-N-(2,3-디하이드로-2,2,3,3-테트라플루오로벤조푸란-5-일)-피라졸린-1-카복스아미드4- (1,3-benzodioxol-5-yl) -3- (4-difluoromethoxyphenyl) -N- (2,3-dihydro-2,2,3,3-tetrafluorobenzo Furan-5-yl) -pyrazoline-1-carboxamide

[실시예 139]Example 139

4-(1,3-벤조디옥솔-5-일)-3-(4-디플루오로메톡시페닐)-N-(2,3-디하이드로-2,2-디메틸벤조푸란-5-일)피라졸린-1-카복스아미드4- (1,3-benzodioxol-5-yl) -3- (4-difluoromethoxyphenyl) -N- (2,3-dihydro-2,2-dimethylbenzofuran-5-yl) Pyrazoline-1-carboxamide

[실시예 140]Example 140

4-(1,3-벤조디옥솔-5-일)-N-(2,3-디하이드로-2,2-디메틸벤조푸란-5-일)-3-페닐피라졸린-1-카복스아미드4- (1,3-benzodioxol-5-yl) -N- (2,3-dihydro-2,2-dimethylbenzofuran-5-yl) -3-phenylpyrazoline-1-carboxamide

[실시예 141]Example 141

4-(1,3-벤조디옥솔-5-일)-N-(2,3-디하이드로-2,2,3,3-테트라플루오로벤조푸란-5-일)-3-페닐피라졸린-1-카복스아미드4- (1,3-benzodioxol-5-yl) -N- (2,3-dihydro-2,2,3,3-tetrafluorobenzofuran-5-yl) -3-phenylpyrazoline -1-carboxamide

[실시예 142]Example 142

4-(1,3-벤조디옥솔-5-일)-N-(2,2-디플루오로-1,3-벤조디옥솔-5-일)-3-페닐피라졸린-1-카복스아미드4- (1,3-benzodioxol-5-yl) -N- (2,2-difluoro-1,3-benzodioxol-5-yl) -3-phenylpyrazoline-1-carbox amides

[실시예 143]Example 143

4-(1,3-벤조디옥솔-5-일)-N-[4-(4-디플루오로메톡시페녹시)-페닐]-3-페닐피라졸린-1-카복스아미드4- (1,3-benzodioxol-5-yl) -N- [4- (4-difluoromethoxyphenoxy) -phenyl] -3-phenylpyrazolin-1-carboxamide

[실시예 144]Example 144

4-(1,3-벤조디옥솔-5-일)-N-[4-(4-클로로페녹시)-페닐]-3-페닐피라졸린-1-카복스아미드4- (1,3-benzodioxol-5-yl) -N- [4- (4-chlorophenoxy) -phenyl] -3-phenylpyrazolin-1-carboxamide

[실시예 145]Example 145

4-(2,2-디플루오로-1,3-벤조디옥솔-5-일)-N-[4-(4-디플루오로메톡시페녹시)페닐]-3-(4-플루오로페닐)피라졸린-1-카복스아미드4- (2,2-difluoro-1,3-benzodioxol-5-yl) -N- [4- (4-difluoromethoxyphenoxy) phenyl] -3- (4-fluorophenyl Pyrazoline-1-carboxamide

[실시예 146]Example 146

N-[4-(4-클로로페녹시)페닐]-4-(2,2,-디플루오로-1,3-벤조디옥솔-5-일)-3-(4-플루오로페닐)피라졸린-1-카복스아미드N- [4- (4-chlorophenoxy) phenyl] -4- (2,2, -difluoro-1,3-benzodioxol-5-yl) -3- (4-fluorophenyl) pyra Sleepy-1-carboxamide

[실시예 147]Example 147

4,N-비스(2,2-디플루오로-1,3-벤조디옥솔-5-일)-3-(4-플루오로페닐)피라졸린-1-카복스아미드4, N-bis (2,2-difluoro-1,3-benzodioxol-5-yl) -3- (4-fluorophenyl) pyrazolin-1-carboxamide

[실시예 148]Example 148

4-(2,2-디플루오로-1,3-벤조디옥솔-5-일)-3-(4-플루오로페닐)-N-(2,3-디하이드로-2,2,3,3-테트라플루오로벤조푸란-5-일)피라졸린-1-카복스아미드4- (2,2-difluoro-1,3-benzodioxol-5-yl) -3- (4-fluorophenyl) -N- (2,3-dihydro-2,2,3, 3-tetrafluorobenzofuran-5-yl) pyrazoline-1-carboxamide

[실시예 149]Example 149

4-(2,2-디플루오로-1,3-벤조디옥솔-5-일)-3-(4-플루오로페닐)-N-(2,3-디하이드로-2,2-디메틸벤조푸란-5-일)-피라졸린-1-카복스아미드4- (2,2-difluoro-1,3-benzodioxol-5-yl) -3- (4-fluorophenyl) -N- (2,3-dihydro-2,2-dimethylbenzo Furan-5-yl) -pyrazoline-1-carboxamide

[실시예 150]Example 150

4-(2,2-디플루오로-1,3-벤조디옥솔-5-일)-N-[4-(4-디플루오로메톡시페녹시)페닐]-3-페닐피라졸린-1-카복스아미드4- (2,2-difluoro-1,3-benzodioxol-5-yl) -N- [4- (4-difluoromethoxyphenoxy) phenyl] -3-phenylpyrazoline-1- Carboxamide

[실시예 151]Example 151

N-[4-(4-클로로페녹시)페닐]-4-(2,2-디플루오로-1,3-벤조디옥솔-5-일)-3-페닐피라졸린-1-카복스아미드N- [4- (4-chlorophenoxy) phenyl] -4- (2,2-difluoro-1,3-benzodioxol-5-yl) -3-phenylpyrazolin-1-carboxamide

[실시예 152]Example 152

4,N-비스(2,2-디플루오로-1,3-벤조디옥솔-5-일)-3-페닐피라졸린-1-카복스아미드4, N-bis (2,2-difluoro-1,3-benzodioxol-5-yl) -3-phenylpyrazoline-1-carboxamide

[실시예 153]Example 153

4-(2,2-디플루오로-1,3-벤조디옥솔-5-일)-N-(2,3-디하이드로-2,2,3,3-테트라플루오로벤조푸란-5-일)-3-페닐피라졸린-1-카복스아미드4- (2,2-difluoro-1,3-benzodioxol-5-yl) -N- (2,3-dihydro-2,2,3,3-tetrafluorobenzofuran-5- I) -3-phenylpyrazoline-1-carboxamide

[실시예 154]Example 154

4-(2,2-디플루오로-1,3-벤조디옥솔-5-일)-N-(2,3-디하이드로-2,3-디메틸벤조푸란-5-일)-3-페닐피라졸린-1-카복스아미드4- (2,2-difluoro-1,3-benzodioxol-5-yl) -N- (2,3-dihydro-2,3-dimethylbenzofuran-5-yl) -3-phenyl Pyrazoline-1-carboxamide

[실시예 155]Example 155

4-(2,2-디플루오로-1,3-벤조디옥솔-5-일)-N-[4-(4-디플루오로메톡시페녹시)페닐]-3-(4-디플루오로메톡시페닐)-피라졸린-1-카복스아미드4- (2,2-difluoro-1,3-benzodioxol-5-yl) -N- [4- (4-difluoromethoxyphenoxy) phenyl] -3- (4-difluorome Methoxyphenyl) -pyrazoline-1-carboxamide

[실시예 156]Example 156

N-[4-(4-클로로페녹시)페닐]-4-(2,2-디플루오로-1,3-벤조디옥솔-5-일)-3-(4-디플루오로메톡시페닐)피라졸린-1-카복스아미드N- [4- (4-chlorophenoxy) phenyl] -4- (2,2-difluoro-1,3-benzodioxol-5-yl) -3- (4-difluoromethoxyphenyl) Pyrazoline-1-carboxamide

[실시예 157]Example 157

4,N-비스(2,2-디플루오로-1,3-벤조디옥솔-5-일)-3-(4-디플루오로메톡시페닐)피라졸린-1-카복스아미드4, N-bis (2,2-difluoro-1,3-benzodioxol-5-yl) -3- (4-difluoromethoxyphenyl) pyrazolin-1-carboxamide

[실시예 158]Example 158

4-(2,2-디플루오로-1,3-벤조디옥솔-5-일)-3-(4-디플루오로메톡시페닐)-N-(2,3-디하이드로-2,2,3,3-테트라플루오로벤조푸란-5-일)피라졸린-1-카복스아미드4- (2,2-difluoro-1,3-benzodioxol-5-yl) -3- (4-difluoromethoxyphenyl) -N- (2,3-dihydro-2,2, 3,3-tetrafluorobenzofuran-5-yl) pyrazoline-1-carboxamide

[실시예 159]Example 159

4-(2,2-디플루오로-1,3-벤조디옥솔-5-일)-3-(4-디플루오로메톡시페닐)-N-(2,3-디하이드로-2,2-디메틸벤조푸란-5-일)피라졸린-1-카복스아미드4- (2,2-difluoro-1,3-benzodioxol-5-yl) -3- (4-difluoromethoxyphenyl) -N- (2,3-dihydro-2,2- Dimethylbenzofuran-5-yl) pyrazoline-1-carboxamide

[실시예 160]Example 160

4-(1,4-벤조디옥산-6-일)-3-(4-클로로페닐)-N-[4-(4-디플루오로메톡시페녹시)페닐]피라졸린-1-카복스아미드4- (1,4-benzodioxan-6-yl) -3- (4-chlorophenyl) -N- [4- (4-difluoromethoxyphenoxy) phenyl] pyrazoline-1-carboxamide

[실시예 161]Example 161

4-(1,4-벤조디옥산-6-일)-N-[4-(4-클로로페녹시)-페닐]-3-(4-클로로페닐)피라졸린-1-카복스아미드4- (1,4-benzodioxan-6-yl) -N- [4- (4-chlorophenoxy) -phenyl] -3- (4-chlorophenyl) pyrazoline-1-carboxamide

[실시예 162]Example 162

4-(1,4-벤조디옥산-6-일)-3-(4-클로로페닐)-N-(2,2-디플루오로-1,3-벤조디옥솔-5-일)피라졸린-1-카복스아미드4- (1,4-benzodioxan-6-yl) -3- (4-chlorophenyl) -N- (2,2-difluoro-1,3-benzodioxol-5-yl) pyrazoline -1-carboxamide

[실시예 163]Example 163

4-(1,4-벤조디옥산-6-일)-3-(4-클로로페닐)-N-(2,3-디하이드로-2,2,3,3-테트라플루오로벤조푸란-5-일)피라졸린-1-카복스아미드4- (1,4-benzodioxan-6-yl) -3- (4-chlorophenyl) -N- (2,3-dihydro-2,2,3,3-tetrafluorobenzofuran-5 -Yl) pyrazoline-1-carboxamide

[실시예 164]Example 164

4-(1,4-벤조디옥산-6-일)-3-(4-클로로페닐)-N-(2,3-디하디드로-2,2-디메틸벤조푸란-5-일)피라졸린-1-카복스아미드4- (1,4-benzodioxan-6-yl) -3- (4-chlorophenyl) -N- (2,3-dihadrodro-2,2-dimethylbenzofuran-5-yl) pyrazoline -1-carboxamide

[실시예 165]Example 165

4-(1,4-벤조디옥산-6-일)-N-[4-(4-디플루오로메톡시페녹시)페닐]-3-4-디플루오로메톡시페닐)피라졸린-1-카복스아미드4- (1,4-benzodioxan-6-yl) -N- [4- (4-difluoromethoxyphenoxy) phenyl] -3-4-difluoromethoxyphenyl) pyrazoline-1-car Voxamide

[실시예 166]Example 166

4-(1,4-벤조디옥산-6-일)-N-[4-(4-클로로페녹시)페닐]-3-(4-디플루오로메톡시페닐)피라졸린-1-카복스아미드4- (1,4-benzodioxan-6-yl) -N- [4- (4-chlorophenoxy) phenyl] -3- (4-difluoromethoxyphenyl) pyrazoline-1-carboxamide

[실시예 167]Example 167

4-(1,4-벤조디옥산-6-일)-N-(2,2-디플루오로-1,3-벤조디옥솔-5-일)-3-(4-디플루오로메톡시페닐)피라졸린-1-카복스아미드4- (1,4-benzodioxan-6-yl) -N- (2,2-difluoro-1,3-benzodioxol-5-yl) -3- (4-difluoromethoxyphenyl Pyrazoline-1-carboxamide

[실시예 168]Example 168

4-(1,4-벤조디옥산-6-일)-3-(4-디플루오로메톡시페닐)-N-(2,3-디하이드로-2,2,3,3-테트라플루오로벤조푸란-5-일)-피라졸린-1-카복스아미드4- (1,4-benzodioxan-6-yl) -3- (4-difluoromethoxyphenyl) -N- (2,3-dihydro-2,2,3,3-tetrafluorobenzo Furan-5-yl) -pyrazoline-1-carboxamide

[실시예 169]Example 169

4-(1,4-벤조디옥산-6-일)-3-(4-디플루오로메톡시페닐)-N-(2,3-디하이드로-2,2-디메틸벤조푸란-5-일)피라졸린-1-카복스아미드4- (1,4-benzodioxan-6-yl) -3- (4-difluoromethoxyphenyl) -N- (2,3-dihydro-2,2-dimethylbenzofuran-5-yl) Pyrazoline-1-carboxamide

[실시예 170]Example 170

4-(1,4-벤조디옥산-6-일)-N-[4-(4-디플루오로메톡시페녹시)페닐]-3-페닐피라졸린-1-카복스아미드4- (1,4-benzodioxan-6-yl) -N- [4- (4-difluoromethoxyphenoxy) phenyl] -3-phenylpyrazolin-1-carboxamide

[실시예 171]Example 171

4-(1,4-벤조디옥산-6-일)-N-[4-(4-클로로페녹시)-페닐]-3-페닐피라졸린-1-카복스아미드4- (1,4-benzodioxan-6-yl) -N- [4- (4-chlorophenoxy) -phenyl] -3-phenylpyrazolin-1-carboxamide

[실시예 172]Example 172

4-(1,4-벤조디옥산-6-일)-N-(2,2-디플루오로-1,3-벤조디옥솔-5-일)-3-페닐피라졸린-1-카복스아미드4- (1,4-benzodioxan-6-yl) -N- (2,2-difluoro-1,3-benzodioxol-5-yl) -3-phenylpyrazoline-1-carbox amides

[실시예 173]Example 173

4-(1,4-벤조디옥산-6-일)-N-(2,3-디하이드로-2,2,3,3-테트라플루오로벤조푸란-5-일)-3-페닐피라졸린-1-카복스아미드4- (1,4-benzodioxan-6-yl) -N- (2,3-dihydro-2,2,3,3-tetrafluorobenzofuran-5-yl) -3-phenylpyrazoline -1-carboxamide

[실시예 174]Example 174

4-(1,4-벤조디옥산-6-일)-N-(2,3-디하이드로-2,2-디메틸벤조푸란-5-일)-3-페닐피라졸린-1-카복스아미드4- (1,4-benzodioxan-6-yl) -N- (2,3-dihydro-2,2-dimethylbenzofuran-5-yl) -3-phenylpyrazoline-1-carboxamide

[실시예 175]Example 175

3-(1,3-벤조디옥솔-5-일)-N-[4-(4-디플루오로메톡시페녹시)페닐]-4-(4-플루오로페닐)-N-메틸피라졸린-1-카복스아미드3- (1,3-benzodioxol-5-yl) -N- [4- (4-difluoromethoxyphenoxy) phenyl] -4- (4-fluorophenyl) -N-methylpyrazoline- 1-carboxamide

[실시예 176]Example 176

3-(1,3-벤조디옥솔-5-일)-N-[4-(4-클로로페녹시)페닐]-4-(4-플루오로페닐)피라졸린-1-카복스아미드3- (1,3-benzodioxol-5-yl) -N- [4- (4-chlorophenoxy) phenyl] -4- (4-fluorophenyl) pyrazoline-1-carboxamide

[실시예 177]Example 177

3-(1,3-벤조디옥솔-5-일)-N-(2,2-디플루오로-1,3-벤조디옥솔-5-일)-4-(4-플루오로페닐)피라졸린-1-카복스아미드3- (1,3-benzodioxol-5-yl) -N- (2,2-difluoro-1,3-benzodioxol-5-yl) -4- (4-fluorophenyl) pyra Sleepy-1-carboxamide

[실시예 178]Example 178

3-(1,3-벤조디옥솔-5-일)-4-(4-플루오로페닐)-N-(2,3-디하이드로-2,2,3,3-테트라플루오로벤조푸란-5-일)피라졸린-1-카복스아미드3- (1,3-benzodioxol-5-yl) -4- (4-fluorophenyl) -N- (2,3-dihydro-2,2,3,3-tetrafluorobenzofuran- 5-yl) pyrazoline-1-carboxamide

[실시예 179]Example 179

3-(1,3-벤조디옥솔-5-일)-4-(4-플루오로페닐)-N-(2,3-디하이드로-2,2-디메틸벤조푸란-5-일)피라졸린-1-카복스아미드3- (1,3-benzodioxol-5-yl) -4- (4-fluorophenyl) -N- (2,3-dihydro-2,2-dimethylbenzofuran-5-yl) pyrazoline -1-carboxamide

[실시예 180]Example 180

3-(2,2-디플루오로-1,3-벤조디옥솔-5-일)-N-[4-(4-디플루오로메톡시페녹시)페닐]-4-(4-플루오로페닐)피라졸린-1-카복스아미드3- (2,2-difluoro-1,3-benzodioxol-5-yl) -N- [4- (4-difluoromethoxyphenoxy) phenyl] -4- (4-fluorophenyl Pyrazoline-1-carboxamide

[실시예 181]Example 181

N-[4-(4-클로로페녹시)페닐]-3-(2,2-디플루오로-1,3-벤조디옥솔-5-일)-4-(4-플루오로페닐)-N-메틸피라졸린-1-카복스아미드N- [4- (4-chlorophenoxy) phenyl] -3- (2,2-difluoro-1,3-benzodioxol-5-yl) -4- (4-fluorophenyl) -N -Methylpyrazoline-1-carboxamide

[실시예 182]Example 182

3,N-비스(2,2-디플루오로-1,3-벤조디옥솔-5-일)-4-(4-플루오로페닐)피라졸린-1-카복스아미드3, N-bis (2,2-difluoro-1,3-benzodioxol-5-yl) -4- (4-fluorophenyl) pyrazolin-1-carboxamide

[실시예 183]Example 183

3-(2,2-디플루오로-1,3-벤조디옥솔-5-일)-4-(4-플루오로페닐)-N-(2,3-디하이드로-2,2,3,3-테르라플루오로벤조푸란-5-일)-피라졸린-1-카복스아미드3- (2,2-difluoro-1,3-benzodioxol-5-yl) -4- (4-fluorophenyl) -N- (2,3-dihydro-2,2,3, 3-terrafluorobenzofuran-5-yl) -pyrazoline-1-carboxamide

[실시예 184]Example 184

3-(2,2-디플루오로-1,3-벤조디옥솔-5-일)-4-(4-플루오로페닐)-N-(2,3-디하이드로-2,2-디메틸벤조푸란-5-일)-피라졸린-1-카복스아미드3- (2,2-difluoro-1,3-benzodioxol-5-yl) -4- (4-fluorophenyl) -N- (2,3-dihydro-2,2-dimethylbenzo Furan-5-yl) -pyrazoline-1-carboxamide

[실시예 185]Example 185

3-(1,4-벤조디옥산-6-일)-N-[4-(4-디플루오로메톡시페녹시)페닐]-4-페닐피라졸린-1-카복스아미드3- (1,4-benzodioxan-6-yl) -N- [4- (4-difluoromethoxyphenoxy) phenyl] -4-phenylpyrazolin-1-carboxamide

[실시예 186]Example 186

3-(1,4-벤조디옥산-6-일)-N-[4-(4-클로로페녹시)페닐]-4-페닐피라졸린-1-카복스아미드3- (1,4-benzodioxan-6-yl) -N- [4- (4-chlorophenoxy) phenyl] -4-phenylpyrazolin-1-carboxamide

[실시예 187]Example 187

3-(1,4-벤조디옥산-6-일)-N-(2,2-디플루오로-1,3-벤조디옥솔-5-일)-N-메틸-4-페닐피라졸린-1-카복스아미드3- (1,4-benzodioxan-6-yl) -N- (2,2-difluoro-1,3-benzodioxol-5-yl) -N-methyl-4-phenylpyrazoline- 1-carboxamide

[실시예 188]Example 188

3-(1,4-벤조디옥산-6-일)-N-(2,3-디하이드로-2,2,3,3-테트라플루오로벤조푸란-5-일)-4-페닐피라졸린-1-카복스아미드3- (1,4-benzodioxan-6-yl) -N- (2,3-dihydro-2,2,3,3-tetrafluorobenzofuran-5-yl) -4-phenylpyrazoline -1-carboxamide

[실시예 189]Example 189

3-(1,4-벤조디옥산-6-일)-N-(2,3-디하이드로-2,2-디메틸벤조푸란-5-일)-4-페닐피라졸린-1-카복스아미드3- (1,4-benzodioxan-6-yl) -N- (2,3-dihydro-2,2-dimethylbenzofuran-5-yl) -4-phenylpyrazoline-1-carboxamide

[실시예 190]Example 190

N-[4-(4-디플루오로메톡시페녹시)페닐]-3-(2,3-디하이드로-2,2-디메틸벤조푸란-5-일)-4-페닐피라졸린-1-카복스아미드N- [4- (4-difluoromethoxyphenoxy) phenyl] -3- (2,3-dihydro-2,2-dimethylbenzofuran-5-yl) -4-phenylpyrazoline-1-car Voxamide

[실시예 191]Example 191

N-[4-(4-클로로페녹시)페닐]-3-(2,3-디하이드로-2,2-디메틸벤조푸란-5-일)-4-페닐피라졸린-1-카복스아미드N- [4- (4-chlorophenoxy) phenyl] -3- (2,3-dihydro-2,2-dimethylbenzofuran-5-yl) -4-phenylpyrazoline-1-carboxamide

[실시예 192]Example 192

N-(2,2-디플루오로-1,3-벤조디옥솔-5-일)-3-(2,3-디하이드로-2,2-디메틸벤조푸란-5-일)-4-페닐피라졸린-1-카복스아미드N- (2,2-difluoro-1,3-benzodioxol-5-yl) -3- (2,3-dihydro-2,2-dimethylbenzofuran-5-yl) -4-phenyl Pyrazoline-1-carboxamide

[실시예 193]Example 193

N-(2,3-디하이드로-2,2,3,3-테트라플루오로벤조푸란-5-일)-3-(2,3-디하이드로-2,2-디메틸벤조푸란-5-일)-N-메틸-4-페닐피라졸린-1-카복스아미드N- (2,3-dihydro-2,2,3,3-tetrafluorobenzofuran-5-yl) -3- (2,3-dihydro-2,2-dimethylbenzofuran-5-yl ) -N-methyl-4-phenylpyrazoline-1-carboxamide

[실시예 194]Example 194

3,N-비스(2,3-디하이드로-2,2-디메틸벤조푸란-5-일)-4-페닐피라졸린-1-카복스아미드3, N-bis (2,3-dihydro-2,2-dimethylbenzofuran-5-yl) -4-phenylpyrazoline-1-carboxamide

[실시예 195]Example 195

N-[4-(4-디플루오로메톡시페녹시)페닐]-4-(4-플루오로페닐)-3-(4-메틸페닐)피라졸린-1-카복스아미드N- [4- (4-difluoromethoxyphenoxy) phenyl] -4- (4-fluorophenyl) -3- (4-methylphenyl) pyrazoline-1-carboxamide

[실시예 196]Example 196

N-[4-(4-클로로페녹시)페닐]-4-(4-플루오로페닐)-3-(4-메틸페닐)피라졸린-1-카복스아미드N- [4- (4-chlorophenoxy) phenyl] -4- (4-fluorophenyl) -3- (4-methylphenyl) pyrazoline-1-carboxamide

[실시예 197]Example 197

N-(2,2-디플루오로-1,3-벤조디옥솔-5-일)-4-(4-플루오로페닐)-3-(4-메틸페닐)피라졸린-1-카복스아미드N- (2,2-difluoro-1,3-benzodioxol-5-yl) -4- (4-fluorophenyl) -3- (4-methylphenyl) pyrazoline-1-carboxamide

[실시예 198]Example 198

4-(4-플루오로페닐)-N-(2,3-디하이드로-2,2,3,3-테트라플루오로벤조푸란-5-일)-3-(4-메틸페닐)피라졸린-1-카복스아미드4- (4-fluorophenyl) -N- (2,3-dihydro-2,2,3,3-tetrafluorobenzofuran-5-yl) -3- (4-methylphenyl) pyrazolin-1 Carboxamide

[실시예 199]Example 199

4-(4-플루오로페닐)-N-(2,3-디하이드로-2,2-디메틸벤조푸란-5-일)-N-메틸-3-(4-메틸페닐)피라졸린-1-카복스아미드4- (4-fluorophenyl) -N- (2,3-dihydro-2,2-dimethylbenzofuran-5-yl) -N-methyl-3- (4-methylphenyl) pyrazoline-1-car Voxamide

[실시예 200]Example 200

N-[4-(4-디플루오로메톡시페녹시)페닐]-4-(3-플루오로페닐)-N-메틸-3-(4-메틸페닐)피라졸린-1-카복스아미드N- [4- (4-difluoromethoxyphenoxy) phenyl] -4- (3-fluorophenyl) -N-methyl-3- (4-methylphenyl) pyrazoline-1-carboxamide

[실시예 201]Example 201

N-[4-(4-클로로페녹시)페닐]-4-(3-플루오로페닐)-3-(4-메틸페닐)피라졸린-1-카복스아미드N- [4- (4-chlorophenoxy) phenyl] -4- (3-fluorophenyl) -3- (4-methylphenyl) pyrazoline-1-carboxamide

[실시예 202]Example 202

N-(2,2-디플루오로-1,3-벤조디옥솔-5-일)-4-(3-플루오로페닐)-3-(4-메틸페닐)피라졸린-1-카복스아미드N- (2,2-difluoro-1,3-benzodioxol-5-yl) -4- (3-fluorophenyl) -3- (4-methylphenyl) pyrazoline-1-carboxamide

[실시예 203]Example 203

4-(3-플루오로페닐)-N-(2,3-디하이드로-2,2,3,3-테트라플루오로벤조푸란-5-일)-3-(4-메틸페닐)피라졸린-1-카복스아미도4- (3-fluorophenyl) -N- (2,3-dihydro-2,2,3,3-tetrafluorobenzofuran-5-yl) -3- (4-methylphenyl) pyrazolin-1 -Carbox Amido

[실시예 204]Example 204

4-(3-플루오로페닐)-N-(2,3-디하이드로-2,2-디메틸벤조푸란-5-일)-3-(4-메틸페닐)피라졸린-1-카복스아미드4- (3-fluorophenyl) -N- (2,3-dihydro-2,2-dimethylbenzofuran-5-yl) -3- (4-methylphenyl) pyrazolin-1-carboxamide

[실시예 205]Example 205

N-[4-(4-디플루오로메톡시페녹시)페닐]-4-(2-플루오로페닐)-3-(4-메틸페닐)피라졸린-1-카복스아미드N- [4- (4-difluoromethoxyphenoxy) phenyl] -4- (2-fluorophenyl) -3- (4-methylphenyl) pyrazoline-1-carboxamide

[실시예 206]Example 206

N-[4-(4-클로로페녹시)페닐]-4-(3-플루오로페닐)N-메틸-3-(4-메틸페닐)피라졸린-1-카복스아미드N- [4- (4-chlorophenoxy) phenyl] -4- (3-fluorophenyl) N-methyl-3- (4-methylphenyl) pyrazoline-1-carboxamide

[실시예 207]Example 207

N-(2,2-디플루오로-1,3-벤조디옥솔-5-일)-4-(2-플루오로페닐)-3-(4-메틸페닐)피라졸린-1-카복스아미드N- (2,2-difluoro-1,3-benzodioxol-5-yl) -4- (2-fluorophenyl) -3- (4-methylphenyl) pyrazoline-1-carboxamide

[실시예 208]Example 208

4-(2-플루오로페닐)-N-(2,3-디하이드로-2,2,3,3-테트라플루오로벤조푸란-5-일)-3-(4-메틸페닐)피라졸린-1-카복스아미드4- (2-fluorophenyl) -N- (2,3-dihydro-2,2,3,3-tetrafluorobenzofuran-5-yl) -3- (4-methylphenyl) pyrazolin-1 Carboxamide

[실시예 209]Example 209

4-(2-플루오로페닐)-N-(2,3-디하이드로-2,2,-디메틸벤조푸란-5-일)-3-(4-메틸페닐)피라졸린-1-카복스아미드4- (2-fluorophenyl) -N- (2,3-dihydro-2,2, -dimethylbenzofuran-5-yl) -3- (4-methylphenyl) pyrazoline-1-carboxamide

[실시예 210]Example 210

N-[4-(4-디플루오로메톡시페녹시)페닐]-3-(3-플루오로페닐)-4-(4-플루오로페닐)피라졸린-1-카복스아미드N- [4- (4-difluoromethoxyphenoxy) phenyl] -3- (3-fluorophenyl) -4- (4-fluorophenyl) pyrazoline-1-carboxamide

[실시예 211]Example 211

N-[4-(4-클로로페녹시)페닐]-3-(3-플루오로페닐)-4-(4-플루오로페닐)피라졸린-1-카복스아미드N- [4- (4-chlorophenoxy) phenyl] -3- (3-fluorophenyl) -4- (4-fluorophenyl) pyrazoline-1-carboxamide

[실시예 212]Example 212

N-(2,2-디플루오로-1,3-벤조디옥솔-5-일)-3-(3-플루오로페닐-4-(4-플루오로페닐)-N-메틸피라졸린-1-카복스아미드N- (2,2-difluoro-1,3-benzodioxol-5-yl) -3- (3-fluorophenyl-4- (4-fluorophenyl) -N-methylpyrazoline-1 Carboxamide

[실시예 213]Example 213

3-(3-플루오로페닐)-4-(4-플루오로페닐)-N-(2,3-디하이드로-2,2,3,3-테트라플루오로벤조푸란-5-일)피라졸린-1-카복스아미드3- (3-fluorophenyl) -4- (4-fluorophenyl) -N- (2,3-dihydro-2,2,3,3-tetrafluorobenzofuran-5-yl) pyrazoline -1-carboxamide

[실시예 214]Example 214

3-(3-플루오로페닐)-4-(4-플루오로페닐)-N-(2,3-디하이드로-2,2-디메틸벤조푸란-5-일)피라졸린-1-카복스아미드3- (3-fluorophenyl) -4- (4-fluorophenyl) -N- (2,3-dihydro-2,2-dimethylbenzofuran-5-yl) pyrazolin-1-carboxamide

[실시예 215]Example 215

N-[4-(4-디플루오로메톡시페녹시)페닐]-3-(2-플루오로페닐)-4-(4-플루오로페닐)피라졸린-1-카복스아미드N- [4- (4-difluoromethoxyphenoxy) phenyl] -3- (2-fluorophenyl) -4- (4-fluorophenyl) pyrazoline-1-carboxamide

[실시예 216]Example 216

N-[4-(4-클로로페녹시)페닐]-3-(2-플루오로페닐)-4-(4-플루오로페닐)피라조린-1-카복스아미드N- [4- (4-chlorophenoxy) phenyl] -3- (2-fluorophenyl) -4- (4-fluorophenyl) pyrazorin-1-carboxamide

[실시예 217]Example 217

N-(2,2-디플루오로-1,3-벤조디옥솔-5-일)-3-(2-플루오로페닐)-4-(4-플루오로페닐)피라졸린-1-카복스아미드N- (2,2-difluoro-1,3-benzodioxol-5-yl) -3- (2-fluorophenyl) -4- (4-fluorophenyl) pyrazoline-1-carbox amides

[실시예 218]Example 218

3-(2-(플루오로페닐)-4-(4-플루오로페닐)-N-(2,3-디하이드로-2,2,3,3-테트라플루오로벤조푸란-5-일)-N-메틸피라졸린-1-카복스아미드3- (2- (fluorophenyl) -4- (4-fluorophenyl) -N- (2,3-dihydro-2,2,3,3-tetrafluorobenzofuran-5-yl)- N-methylpyrazoline-1-carboxamide

[실시예 219]Example 219

3-(2-플루오로페닐)-4-(4-플루오로페닐)-N-(2,3-디하이드로-2,2-디메틸벤조푸란-5-일)피라졸린-1-카복스아미드3- (2-fluorophenyl) -4- (4-fluorophenyl) -N- (2,3-dihydro-2,2-dimethylbenzofuran-5-yl) pyrazoline-1-carboxamide

[실시예 220]Example 220

3,4-비스(4-플루오로페닐)-N-(2,3-디하이드로-2,2,3,3,7-펜타플루오로벤조푸란-5-일)피라졸린-1-카복스아미드3,4-bis (4-fluorophenyl) -N- (2,3-dihydro-2,2,3,3,7-pentafluorobenzofuran-5-yl) pyrazoline-1-carbox amides

[실시예 221]Example 221

4-(4-클로로페닐)-N-(2,3-디하이드로-2,2,3,3,7-펜타플루오로벤조푸란-5-일)-3-(4-메틸페닐)피라졸린-1-카복스아미드4- (4-Chlorophenyl) -N- (2,3-dihydro-2,2,3,3,7-pentafluorobenzofuran-5-yl) -3- (4-methylphenyl) pyrazoline- 1-carboxamide

[실시예 222]Example 222

N-(2,3-디하이드로-2,2,3,3,7-펜타플루오로벤조푸란-5-일)-3,4-디페닐피라졸린-1-카복스아미드N- (2,3-dihydro-2,2,3,3,7-pentafluorobenzofuran-5-yl) -3,4-diphenylpyrazoline-1-carboxamide

[실시예 223]Example 223

3-(4-디플루오로메톡시페닐)-N-(2,3-디하이드로-2,2,3,3,7-펜타플루오로벤조푸란-5-일)-4-페닐피라졸린-1-카복스아미드3- (4-difluoromethoxyphenyl) -N- (2,3-dihydro-2,2,3,3,7-pentafluorobenzofuran-5-yl) -4-phenylpyrazoline-1 Carboxamide

[실시예 224]Example 224

3-(4-클로로페닐)-N-(2,3-디하이드로-2,2,3,3,7-펜타플루오로벤조푸란-5-일)-4-페닐피라졸린-1-카복스아미드3- (4-chlorophenyl) -N- (2,3-dihydro-2,2,3,3,7-pentafluorobenzofuran-5-yl) -4-phenylpyrazoline-1-carbox amides

[실시예 225]Example 225

3,4-비스(4-플루오로페닐)-N-(2,2,6-트리메틸-1,3-벤조디옥솔-5-일)피라졸린-1-카복스아미드3,4-bis (4-fluorophenyl) -N- (2,2,6-trimethyl-1,3-benzodioxol-5-yl) pyrazoline-1-carboxamide

[실시예 226]Example 226

4-(4-클로로페닐)-N-(2,2,6-트리메틸-1,3-벤조디옥솔-5-일)-3-(4-메틸페닐)피라졸린-1-카복스아미드4- (4-chlorophenyl) -N- (2,2,6-trimethyl-1,3-benzodioxol-5-yl) -3- (4-methylphenyl) pyrazoline-1-carboxamide

[실시예 227]Example 227

N-(2,2,6-트리메틸-1,3-벤조디옥솔-5-일)-3,4-디페닐피라졸린-1-카복스아미드N- (2,2,6-trimethyl-1,3-benzodioxol-5-yl) -3,4-diphenylpyrazolin-1-carboxamide

[실시예 228]Example 228

3-(4-디플루오로메톡시페닐)-N-(2,2,6-트리메틸-1,3-벤조디옥솔-5-일)-4-페닐피라졸린-1-카복스아미드3- (4-difluoromethoxyphenyl) -N- (2,2,6-trimethyl-1,3-benzodioxol-5-yl) -4-phenylpyrazoline-1-carboxamide

[실시예 229]Example 229

3-(4-클로로페닐)-N-(2,2,6-트리메틸-1,3-벤조디옥솔-5-일)-4-페닐피라졸린-1-카복스아미드3- (4-chlorophenyl) -N- (2,2,6-trimethyl-1,3-benzodioxol-5-yl) -4-phenylpyrazoline-1-carboxamide

[실시예 230]Example 230

3,4-비스(4-플루오로페닐)-N-(7-메톡시-2,2-디메틸-1,3-벤조디옥솔-5-일)피라졸린-1-카복스아미드3,4-bis (4-fluorophenyl) -N- (7-methoxy-2,2-dimethyl-1,3-benzodioxol-5-yl) pyrazoline-1-carboxamide

[실시예 231]Example 231

4-(클로로페닐)-N-(7-메톡시-2,2-디메틸-1,3-벤조디옥솔-5-일)-3-(4-메틸페닐)피라졸린-1-카복스아미드4- (chlorophenyl) -N- (7-methoxy-2,2-dimethyl-1,3-benzodioxol-5-yl) -3- (4-methylphenyl) pyrazoline-1-carboxamide

[실시예 232]Example 232

N-(7-메톡시-2,2-디메틸-1,3-벤조디옥솔-5-일)-3,4-디페닐피라졸린-1-카복스아미드N- (7-methoxy-2,2-dimethyl-1,3-benzodioxol-5-yl) -3,4-diphenylpyrazoline-1-carboxamide

[실시예 233]Example 233

3-(4-디플루오로메톡시페닐)-N-(7-메톡시-2,2-디메틸-1,3-벤조디옥솔-5-일)-4-페닐피라졸린-1-카복스아미드3- (4-difluoromethoxyphenyl) -N- (7-methoxy-2,2-dimethyl-1,3-benzodioxol-5-yl) -4-phenylpyrazoline-1-carboxamide

[실시예 234]Example 234

3-(4-클로로페닐)-N-(7-메톡시-2,2-디메틸-1,3-벤조디옥솔-5-일)-4-페닐피라졸린-1-카복스아미드3- (4-chlorophenyl) -N- (7-methoxy-2,2-dimethyl-1,3-benzodioxol-5-yl) -4-phenylpyrazoline-1-carboxamide

[실시예 235]Example 235

3,4-비스(4-플루오로페닐)-N-[2,2-디메틸-7-(1-메틸에틸)-1,3-벤조디옥솔-5-일]피라졸린-1-카복스아미드3,4-bis (4-fluorophenyl) -N- [2,2-dimethyl-7- (1-methylethyl) -1,3-benzodioxol-5-yl] pyrazoline-1-carbox amides

[실시예 236]Example 236

4-(4-클로로페닐)-N-[2,2-디메틸-7-(1,메틸에틸)-1,3-벤조디옥솔-5-일]-3-(4-메틸페닐)피라졸린-1-카복스아미드4- (4-Chlorophenyl) -N- [2,2-dimethyl-7- (1, methylethyl) -1, 3-benzodioxol-5-yl] -3- (4-methylphenyl) pyrazoline- 1-carboxamide

[실시예 237]Example 237

N-[2,2-디메틸-7-(1-메틸에틸)-1,3-벤조디옥솔-5-일]-3,4-디페닐피라졸린-1-카복스아미드N- [2,2-dimethyl-7- (1-methylethyl) -1,3-benzodioxol-5-yl] -3,4-diphenylpyrazolin-1-carboxamide

[실시예 238]Example 238

3-(4-디플루오로메톡시페닐)-N-[2,2-디메틸-7-(1-메틸에틸)-1,3-벤조디옥솔-5-일]-4-페닐피라졸린-1-카복스아미드3- (4-difluoromethoxyphenyl) -N- [2,2-dimethyl-7- (1-methylethyl) -1,3-benzodioxol-5-yl] -4-phenylpyrazoline-1 Carboxamide

[실시예 239]Example 239

3-(4-클로로페닐)-N-[2,2-디메틸-7-(1-메틸에틸)-1,3-벤조디옥솔-5-일]-4-페닐피라졸린-1-카복스아미드3- (4-chlorophenyl) -N- [2,2-dimethyl-7- (1-methylethyl) -1,3-benzodioxol-5-yl] -4-phenylpyrazoline-1-carbox amides

[실시예 240]Example 240

3,4-비스(4-플루오로페닐)-N-(2,3-디하이드로-7-에틸-2,2,3,3-테트라플루오로벤조푸란-5-일)피라졸린-1-카복스아미드3,4-bis (4-fluorophenyl) -N- (2,3-dihydro-7-ethyl-2,2,3,3-tetrafluorobenzofuran-5-yl) pyrazoline-1- Carboxamide

[실시예 241]Example 241

4-(4-클로로페닐)-N-(2,3-디하이드로-7-에틸-2,2,3,3-테트라플루오로벤조푸란-5-일)-3-(4-메틸페닐)피라졸린-1-카복스아미드4- (4-chlorophenyl) -N- (2,3-dihydro-7-ethyl-2,2,3,3-tetrafluorobenzofuran-5-yl) -3- (4-methylphenyl) pyra Sleepy-1-carboxamide

[실시예 242]Example 242

N-(2,3-디하이드로-7-에틸-2,2,3,3-테트라플루오로벤조푸란-5-일)-3,4-디페닐피라졸린-1-카복스아미드N- (2,3-dihydro-7-ethyl-2,2,3,3-tetrafluorobenzofuran-5-yl) -3,4-diphenylpyrazoline-1-carboxamide

[실시예 243]Example 243

3-(4-디플루오로메톡시페닐)-N-(2,3-디하이드로-7-에틸-2,2,3,3-테트라플루오로벤조푸란-5-일)-4-페닐피라졸린-1-카복스아미드3- (4-difluoromethoxyphenyl) -N- (2,3-dihydro-7-ethyl-2,2,3,3-tetrafluorobenzofuran-5-yl) -4-phenylpyrazoline -1-carboxamide

[실시예 244]Example 244

3-(4-클로로페닐)-N-(2,3-디하이드로-7-에틸-2,2,3,3-테트라플루오로벤조푸란-5-일)-4-페닐피라졸린-1-카복스아미드3- (4-chlorophenyl) -N- (2,3-dihydro-7-ethyl-2,2,3,3-tetrafluorobenzofuran-5-yl) -4-phenylpyrazoline-1- Carboxamide

[실시예 245]Example 245

3-(4-클로로페닐)-N-[4-(4-메틸설포닐페녹시)-페닐]-4-페닐피라졸린-1-카복스아미드3- (4-chlorophenyl) -N- [4- (4-methylsulfonylphenoxy) -phenyl] -4-phenylpyrazoline-1-carboxamide

[실시예 246]Example 246

3,4-비스(4-플루오로페닐)-N-[4-(4-메틸설포닐페녹시)-페닐)피라졸린-1-카복스아미드3,4-bis (4-fluorophenyl) -N- [4- (4-methylsulfonylphenoxy) -phenyl) pyrazoline-1-carboxamide

[실시예 247]Example 247

3-(4-디플루오로메톡시페닐)-N-[4-(4-메틸설포닐페녹시)-페닐]-4-페닐피라졸린-1-카복스아미드3- (4-Difluoromethoxyphenyl) -N- [4- (4-methylsulfonylphenoxy) -phenyl] -4-phenylpyrazoline-1-carboxamide

[실시예 248]Example 248

3-(4-클로로페닐)-4-(4-플루오로페닐)-N-[4-(4-메틸설포닐페녹시)페닐]피라졸린-1-카복스아미드3- (4-chlorophenyl) -4- (4-fluorophenyl) -N- [4- (4-methylsulfonylphenoxy) phenyl] pyrazoline-1-carboxamide

[실시예 249]Example 249

N-[4-(4-메틸설포닐페녹시)페닐]-3,4-디페닐피라졸린-1-카복스아미드N- [4- (4-methylsulfonylphenoxy) phenyl] -3,4-diphenylpyrazoline-1-carboxamide

[실시예 250]Example 250

3,4-비스(4-플루오로페닐)-N-(2,3-디하이드로-7-디플루오로메톡시-2,2-디메틸벤조푸란-5-일)피라졸린-1-카복스아미드3,4-bis (4-fluorophenyl) -N- (2,3-dihydro-7-difluoromethoxy-2,2-dimethylbenzofuran-5-yl) pyrazoline-1-carboxamide

[실시예 251]Example 251

4-(4-클로로페닐)-N-(2,3-디하이드로-7-디플루오로메톡시-2,2-디메틸벤조푸란-5-일)-3-(4-메틸페닐)피라졸린-1-카복스아미드4- (4-Chlorophenyl) -N- (2,3-dihydro-7-difluoromethoxy-2,2-dimethylbenzofuran-5-yl) -3- (4-methylphenyl) pyrazoline-1 Carboxamide

[실시예 252]Example 252

N-(2,3-디하이드로-7-디플루오로메톡시-2,2-디메틸벤조푸란-5-일)-3,4-디페닐피라졸린-1-카복스아미드N- (2,3-dihydro-7-difluoromethoxy-2,2-dimethylbenzofuran-5-yl) -3,4-diphenylpyrazolin-1-carboxamide

[실시예 253]Example 253

3-(4-디플루오로메톡시페닐)-N-(2,3-디하이드로-7-디플루오로메톡시-2,2-디메틸벤조푸란-5-일)-4-페닐피라졸린-1-카복스아미드3- (4-difluoromethoxyphenyl) -N- (2,3-dihydro-7-difluoromethoxy-2,2-dimethylbenzofuran-5-yl) -4-phenylpyrazoline-1- Carboxamide

[실시예 254]Example 254

3-(4-클로로페닐)-N-(2,3-디하이드로-7-디플루오로메톡시-2,2-디메틸벤조푸란-5-일)-4-페닐피라졸린-1-카복스아미드3- (4-chlorophenyl) -N- (2,3-dihydro-7-difluoromethoxy-2,2-dimethylbenzofuran-5-yl) -4-phenylpyrazoline-1-carboxamide

[실시예 255]Example 255

N-(7-클로로메틸-2,2-디메틸-1,3-벤조디옥솔-5-일)-3,4-비스(4-플루오로페닐)피라졸린-1-카복스아미드N- (7-chloromethyl-2,2-dimethyl-1,3-benzodioxol-5-yl) -3,4-bis (4-fluorophenyl) pyrazolin-1-carboxamide

[실시예 256]Example 256

N-(7-클로로메틸-2,2-디메틸-1,3-벤조디옥솔-5-일)-4-(4-클로로페닐)-3-(4-메틸페닐)피라졸린-1-카복스아미드N- (7-chloromethyl-2,2-dimethyl-1,3-benzodioxol-5-yl) -4- (4-chlorophenyl) -3- (4-methylphenyl) pyrazoline-1-carbox amides

[실시예 257]Example 257

N-(7-클로로메틸-2,2-디메틸-1,3-벤조디옥솔-5-일)-3,4-디페닐피라졸린-1-카복스아미드N- (7-chloromethyl-2,2-dimethyl-1,3-benzodioxol-5-yl) -3,4-diphenylpyrazolin-1-carboxamide

[실시예 258]Example 258

N-(7-클로로메틸-2,2-디메틸-1,3-벤조디옥솔-5-일)-3-(4-디플루오로메톡시페닐)-4-페닐피라졸린-1-카복스아미드N- (7-chloromethyl-2,2-dimethyl-1,3-benzodioxol-5-yl) -3- (4-difluoromethoxyphenyl) -4-phenylpyrazoline-1-carboxamide

[실시예 259]Example 259

N-(7-클로로메틸-2,2-디메틸-1,3-벤조디옥솔-5-일)-3-(4-클로로페닐)-4-페닐피라졸린-1-카복스아미드N- (7-chloromethyl-2,2-dimethyl-1,3-benzodioxol-5-yl) -3- (4-chlorophenyl) -4-phenylpyrazolin-1-carboxamide

[실시예 260]Example 260

N-(2,3-디하이드로-2,2-디메틸벤조푸란-5-일)-3-[7-(1-메틸에틸)-2,2-디메틸-1,3-벤조디옥솔-5-일]4-페닐피라졸린-1-카복스아미드N- (2,3-dihydro-2,2-dimethylbenzofuran-5-yl) -3- [7- (1-methylethyl) -2,2-dimethyl-1,3-benzodioxol-5 -Yl] 4-phenylpyrazoline-1-carboxamide

[실시예 261]Example 261

N-(2,3-디하이드로-2,2-디메틸벤조푸란)-5-일)-3-(7-메톡시-2,2-디메틸-1,3-벤조디옥솔-5-일)-4-페닐피라졸린-1-카복스아미드N- (2,3-dihydro-2,2-dimethylbenzofuran) -5-yl) -3- (7-methoxy-2,2-dimethyl-1,3-benzodioxol-5-yl) -4-phenylpyrazoline-1-carboxamide

[실시예 262]Example 262

N-(2,3-디하이드로-2,2-디메틸벤조푸란-5-일)-3-(7-플루오로-2,2-디메틸-1,3-벤조디옥솔-5-일)-4-페닐피라졸린-1-카복스아미드N- (2,3-dihydro-2,2-dimethylbenzofuran-5-yl) -3- (7-fluoro-2,2-dimethyl-1,3-benzodioxol-5-yl)- 4-phenylpyrazoline-1-carboxamide

[실시예 263]Example 263

N-(2,3-디하이드로-2,2-디메틸벤조푸란-5-일)-3-(7-디플루오로메톡시-2,2-디메틸-1,3-벤조디옥솔-5-일)-4-페닐피라졸린-1-카복스아미드N- (2,3-dihydro-2,2-dimethylbenzofuran-5-yl) -3- (7-difluoromethoxy-2,2-dimethyl-1,3-benzodioxol-5-yl ) -4-phenylpyrazoline-1-carboxamide

[실시예 264]Example 264

N-(2,2-디플루오로-1,3-벤조디옥솔-5-일)-3-(4-플루오로페닐)-4-(2,3-디하이드로-2,2-디메틸벤조푸란-5-일)-피라졸린-1-카복스아미드N- (2,2-difluoro-1,3-benzodioxol-5-yl) -3- (4-fluorophenyl) -4- (2,3-dihydro-2,2-dimethylbenzo Furan-5-yl) -pyrazoline-1-carboxamide

[실시예 265]Example 265

N-(2,2-디플루오로-1,3-벤조디옥솔-5-일)-3-(4-플루오르페닐)-4-(2,3-디하이드로-2,2,3,3-테트라플루오로벤조푸란-5-일)피라졸린-1-카복스아미드N- (2,2-difluoro-1,3-benzodioxol-5-yl) -3- (4-fluorophenyl) -4- (2,3-dihydro-2,2,3,3 Tetrafluorobenzofuran-5-yl) pyrazoline-1-carboxamide

[실시예 266]Example 266

N-[3-(4-트리플루오로메틸페녹시)페닐]-3,4-비스(4-플루오로페닐)피라졸린-1-카복스아미드N- [3- (4-trifluoromethylphenoxy) phenyl] -3,4-bis (4-fluorophenyl) pyrazoline-1-carboxamide

[실시예 267]Example 267

N-[3-(4-플루오로페녹시)페닐]-3,4-비스(4-플루오로페닐)-피라졸린-1-카복스아미드N- [3- (4-fluorophenoxy) phenyl] -3,4-bis (4-fluorophenyl) -pyrazoline-1-carboxamide

[실시예 268]Example 268

N-[3-(4-디플루오로메톡시페녹시)페닐]-3,4-비스(4-플루오로페닐)피라졸린-1-카복스아미드N- [3- (4-difluoromethoxyphenoxy) phenyl] -3,4-bis (4-fluorophenyl) pyrazoline-1-carboxamide

[실시예 269]Example 269

3,4-비스(4-플루오로페닐)-N-[3-(4-메틸페녹시)페닐]-피라졸린-1-카복스아미드3,4-bis (4-fluorophenyl) -N- [3- (4-methylphenoxy) phenyl] -pyrazoline-1-carboxamide

[실시예 270]Example 270

3-(7-클로로메틸-2,2-디메틸-1,3-벤조디옥솔-5-일)-4,N-비스(4-플루오로페닐)피라졸린-1-카복스아미드3- (7-chloromethyl-2,2-dimethyl-1,3-benzodioxol-5-yl) -4, N-bis (4-fluorophenyl) pyrazoline-1-carboxamide

[실시예 271]Example 271

N-(2,3-디하이드로-2,2-디메틸벤조푸란-5-일)-4-[7-(1-메틸에틸)-2,2-디메틸-1,3-벤조디옥솔-5-일]-3-페닐피라졸린-1-카복스아미드N- (2,3-dihydro-2,2-dimethylbenzofuran-5-yl) -4- [7- (1-methylethyl) -2,2-dimethyl-1,3-benzodioxol-5 -Yl] -3-phenylpyrazoline-1-carboxamide

[실시예 272]Example 272

N-(2,3-디하이드로-2,2-디메틸벤조푸란-5-일)-4-(7-메톡시-2,2-디메틸-1,3-벤조디옥솔-5-일)-3-페닐피라졸린-1-카복스아미드N- (2,3-dihydro-2,2-dimethylbenzofuran-5-yl) -4- (7-methoxy-2,2-dimethyl-1,3-benzodioxol-5-yl)- 3-phenylpyrazoline-1-carboxamide

[실시예 273]Example 273

N-(2,3-디하이드로-2,2-디메틸벤조푸란-5-일)-4-(7-플루오로-2,2-디메틸-1,3-벤조디옥솔-5-일)-3-페닐피라졸린-1-카복스아미드N- (2,3-dihydro-2,2-dimethylbenzofuran-5-yl) -4- (7-fluoro-2,2-dimethyl-1,3-benzodioxol-5-yl)- 3-phenylpyrazoline-1-carboxamide

N-(2,3-디하이드로-2,2-디메틸벤조푸란-5-일)-4-(7-디플루오로메톡시-2,2-디메틸-1,3-벤조디옥솔-5-일)-3-페닐피라졸린-1-카복스아미드N- (2,3-dihydro-2,2-dimethylbenzofuran-5-yl) -4- (7-difluoromethoxy-2,2-dimethyl-1,3-benzodioxol-5-yl ) -3-phenylpyrazoline-1-carboxamide

[실시예 275]Example 275

4-(7-클로로메틸-2,2-디메틸-1,3-벤조디옥솔-5-일)-3, N-비스(4-플루오로페닐)피라졸린-1-카복스아미드4- (7-chloromethyl-2,2-dimethyl-1,3-benzodioxol-5-yl) -3, N-bis (4-fluorophenyl) pyrazoline-1-carboxamide

본 발명에 따르는 살충성 피라졸린의 일반적 용도에 있어서, 피라졸린은 일반적으로 혼합 또는 희석하지 않고는 사용되지 않지만, 통상적으로 살충 유효량의 피라졸린을 함유하며 시용방법에 맞도록 적절히 제형화된 조성물로 사용된다. 대부분의 농약과 같이, 본 발명의 피라졸린은 살충제의 제형 및 시용형태가 물질의 활성에 영향을 미칠 수 있다는 사실을 인지하여 활성 성분의 분산을 용이하게 하기 위해 통상 사용된 농업적으로 무독한 계면활성제 및 담체와 혼합할 수 있다. 본 발명의 피리졸린은 예를들어 분무제, 분제 또는 입제로 해충을 구제하고자 하는 지역에 사용할 수 있으며, 시용형태는 해충 및 환경에 따라 변화된다. 따라서, 본 발명의 피라졸린은 입자 크기 큰 입체, 산제, 습윤 산제, 유화성 농축물, 액제 등의 형태로 제형화 할 수 있다.In the general use of the pesticidal pyrazoline according to the invention, pyrazoline is generally not used without mixing or dilution, but usually contains a pesticide effective amount of pyrazoline and is formulated with a formulation suitably formulated for the application. Used. Like most pesticides, the pyrazoline of the present invention is an agriculturally toxic interface commonly used to facilitate dispersion of the active ingredient, recognizing that the formulation and application of the pesticide may affect the activity of the substance. It can be mixed with the active agent and the carrier. The pyrizoline of the present invention can be used, for example, in areas where pests are to be controlled by sprays, powders or granules, the application of which varies with the pest and the environment. Thus, the pyrazoline of the present invention can be formulated in the form of large particle sizes, powders, wet powders, emulsifiable concentrates, liquids and the like.

입제는 예를들어 피라졸린의 담체로 제공되는 에터펄자이트 점토 또는 모래와 같은 다공성 또는 무공성 입자로 이루어질 수 있다. 입제의 입자는 비교적 크며, 대표적으로 직경이 약 400 내지 2500미크론이다. 입자는 용액으로 부터 피라졸린을 함침시키거나 피라졸린으로 피복하는데, 때때로 접착제가 사용된다. 입제는 일반적으로 살충 유효량으로 활성성분 0.05 내지 10%, 바람직하게는 0.5 내지 5%를 함유한다.The granulation may consist of porous or nonporous particles such as, for example, etherpulzite clay or sand which is provided as a carrier of pyrazoline. The particles of the granules are relatively large, typically about 400 to 2500 microns in diameter. Particles are impregnated or coated with pyrazoline from solution, sometimes adhesives are used. Granules generally contain from 0.05 to 10%, preferably from 0.5 to 5%, of the active ingredient in an insecticidal effective amount.

분제는 탈크, 애터펄자이트 점토, 키젤거, 피이로 필라이트, 쵸오크, 규조토, 인산 칼슘, 탄산 칼슘, 탄산 마그네슘, 황, 밀가루, 및 살충제용 담체로 작용하는 다른 유기 및 무기 고체 등과 같은 미세 고체와 피라졸린과의 혼합물이다. 이들 미세 고체의 평균 입자 크기는 약 50 미크론미만이다. 해충 구제에 유용한 대표적인 분제는 3-(4-클로로페닐)-N-[4-(4-클로로페녹시)페닐]-4-페닐피라졸린-1-카복스아미드와 같은 피라졸린 1부와 탈크 99부를 함유한다.Powders such as talc, attapulgite clay, Kijelger, pyrophyllite, choke, diatomaceous earth, calcium phosphate, calcium carbonate, magnesium carbonate, sulfur, flour, and other organic and inorganic solids that act as carriers for pesticides It is a mixture of fine solids and pyrazoline. The average particle size of these fine solids is less than about 50 microns. Representative powders useful for pest control include talc and one part of pyrazoline, such as 3- (4-chlorophenyl) -N- [4- (4-chlorophenoxy) phenyl] -4-phenylpyrazoline-1-carboxamide It contains 99 parts.

본 발명의 피라졸린은 적절한 액체중에 용해 시키거나 유화시켜 액상 농축물로 제조할 수 있으며, 탈크, 점토 및 농약 분야에 사용된 다른 공지의 고체 담체와 혼합하여 고체 농축물로 제조할 수 있다. 농축물은 살충 유효량으로서 3-(4-클로로페닐)-N-(2,3-디하이드로-2,2-디메틸벤조푸란-5-일)-4-페닐피라졸린-1-카복스아미드와 같은 피라졸린 약 5 내지 50%와, 계면활성 분산제, 유화제 및 수화제를 포함한 불활성 물질 95 내지 50%를 함유하는 조성물이지만, 실험적으로 활성 성분의 농도가 훨신 더 높을 수도 있다. 농축물은 분무제로 실시하기 위해 물 또는 다른 액체로 희석하거나 분제로 사용하기 위해 추가의 고체 담체로 희석한다.The pyrazoline of the present invention can be prepared as a liquid concentrate by dissolving or emulsifying in a suitable liquid, and can be prepared as a solid concentrate by mixing with other known solid carriers used in talc, clay and pesticide applications. The concentrate was treated with pesticidal effective amounts with 3- (4-chlorophenyl) -N- (2,3-dihydro-2,2-dimethylbenzofuran-5-yl) -4-phenylpyrazoline-1-carboxamide. A composition containing about 5-50% of the same pyrazoline and 95-50% of an inert material, including surfactant dispersants, emulsifiers and hydrating agents, although experimentally the concentration of the active ingredient may be much higher. The concentrate is diluted with water or another liquid to effect a spray or with an additional solid carrier for use as a powder.

고체 농축물(또는 습윤 산제라 칭함)에 대한 대표적인 담체로는 표포토, 점토, 실리카 및 흡수력이 높고 용이하게 수화되는 다른 무기 회석제가 있다. 해충 구제에 유용한 고체 농축물 제제는 수화제로서 나트륨 리그노 설포네이트 및 나트륨 라우릴설페이트를 각각 1.5부씩, 3-(4-클로로페닐)-N-(2,3-디하이드로-2,2-디메틸벤조푸란-5-일)-4-(4-클로로페닐)피라졸린-1-카복스아미드 25부 및 애터펄자이트 점토 72부를 함유한다.Representative carriers for solid concentrates (or wet powders) include table photo, clay, silica, and other inorganic limestones that are highly absorbent and readily hydrated. Solid concentrate preparations useful for pest control include 3- (4-chlorophenyl) -N- (2,3-dihydro-2,2-dimethyl, 1.5 parts each of sodium lignosulfonate and sodium laurylsulfate as a wetting agent. 25 parts of benzofuran-5-yl) -4- (4-chlorophenyl) pyrazoline-1-carboxamide and 72 parts of attapulgite clay.

농축물을 제조하는 것은 본 발명의 저융점 생성물을 수송하는데 유용하다. 이러한 농축물은 저융점 고체 생성물을 1%이상의 용매와 함께 용융시켜 순수한 생성물의 빙점 또는 그이하까지 냉각시킬때 고화되지 않는 농축물을 수득함으로써 제조된다.Preparing the concentrate is useful for transporting the low melting product of the present invention. Such concentrates are prepared by melting a low melting solid product with at least 1% solvent to give a concentrate that does not solidify when cooled to or below the freezing point of the pure product.

유용한 액체 농축물은 유화성 농축물을 포함하며, 이는 물 또는 다른 액체 담체에 용이하게 분산된 균질의 액상 또느 페이스트상 조성물이다. 유화성 농축물은 전부 피라졸린과 액체 또는 고체유화제를 이루어질 수 있거나, 또한 크실렌, 중 방향족 나프타, 이소포론 및 비교적 비휘발성인 다른 유기 용매와 같은 액체 담체를 함유할 수 있다. 사용하는 경우, 이들 농축물은 물 또는 다른 액체 담체에 분산시키고 일반적으로 처리대상 지역에 분무제로 시용된다.Useful liquid concentrates include emulsifiable concentrates, which are homogeneous liquid or paste-like compositions readily dispersed in water or other liquid carriers. Emulsifiable concentrates can all consist of liquid or solid emulsifiers with pyrazolines or can also contain liquid carriers such as xylenes, heavy aromatic naphthas, isophorone and other organic solvents that are relatively nonvolatile. When used, these concentrates are dispersed in water or other liquid carriers and generally applied as sprays to the area to be treated.

살충제에 사용되는 대표적인 계면-활성 수화, 분산 및 유화제로는 예를들면 알킬 및 알킬아릴 설포네이트 및 설페이트, 및 이들의 나트륨염 ; 지방 메틸 타우라이드를 포함한 알킬아미드 설포네이트 ; 알킬아릴 폴리에 테르알콜, 황산화 고급 알콜, 폴리비닐알콜, 폴리에틸렌 옥사이드 ; 설폰화 동식물성 오일 ; 설폰화석유 ; 다가 알콜의 지방산 에스테로 및 이러한 에스테르의 에틸렌 옥사이드 부가 생성물 ; 및 장-쇄 메르캅탄과 메틸렌옥사이드의 부가 생성물이 있다. 유용한 계면-활성제의 여러 다른 형태가 시판되고 있다. 계면활성제는 사용시 일반적으로 살충제 조성물의 약 1 내지 15중량%를 이룬다.Representative interfacial-active hydration, dispersion and emulsifiers used in pesticides include, for example, alkyl and alkylaryl sulfonates and sulfates, and sodium salts thereof; Alkylamide sulfonates including fatty methyl taurides; Alkylaryl polyether alcohols, sulfated higher alcohols, polyvinyl alcohols, polyethylene oxides; Sulfonated animal and vegetable oils; Sulfonated petroleum; Fatty acid esters of polyhydric alcohols and ethylene oxide addition products of such esters; And addition products of long-chain mercaptans and methylene oxides. Several other forms of useful surfactants are commercially available. Surfactants generally comprise from about 1 to 15% by weight of the pesticide composition.

다른 유용한 제제는 아세톤 또는 다른 유기 용매와 같은, 활성 성분이 소기농도에서 완전히 용해되는 용매중의 활성 성분의 간단한 용액을 포함한다.Other useful formulations include simple solutions of the active ingredient in a solvent in which the active ingredient is completely dissolved at the desired concentration, such as acetone or other organic solvents.

사용할 목적으로 희석된 살충제 조성물중 피라졸린의 살충 유효량은 일반적으로 약 0.001중량% 내지 약 8중량%의 범위내이다. 본 분야에 공지된 분무제 또는 분제 조성물의 여러가지 변형물은 본 발명의 피라졸린을 본 분야에서 공지되거나 명백한 조성물로 전화시킴으로써 사용할 수 있다.Insecticidal effective amounts of pyrazoline in diluted pesticide compositions for use are generally in the range of about 0.001% to about 8% by weight. Various variations of spray or powder compositions known in the art can be used by converting the pyrazolines of the invention into compositions known or apparent in the art.

본 발명의 살충제 조성물은 다른 살충제, 살선충제, 살비제, 살진균제, 식물 성장 조절제, 비료 등을 포함한 다른 활성 성분과 함께 제형화할 수 있다. 이 조성물을 사용하여 해충을 구제하는 경우에 피라졸린의 살충유효량을 구제 대상 장소에 시용하는 것이 필요할 뿐이다. 이러한 장소는 예를들어 곤충자체, 곤충이 먹는 식물 또는 곤충 서식지일 수 있다. 그 장소가 토양, 예를들어 농작물이 재배되어 있거나 재배할 토양인 경우에 활성화합물을 토양에 시용할 수 있고 임의로 토양에 혼입할 수 있다. 대부분의 시용 경우에 살충유효량은 헥타르당 약 75 내지 4000g, 바람직하게는 헥타르당 150 내지 3000g이다.The pesticide composition of the present invention may be formulated with other active ingredients including other insecticides, nematicides, acaricides, fungicides, plant growth regulators, fertilizers and the like. In the case of exterminating pests using this composition, it is only necessary to apply an effective pesticide amount of pyrazoline to the site to be controlled. Such places may be, for example, insects themselves, plants or insect habitats that insects eat. If the site is a soil, for example a crop being grown or a soil to be grown, the active compound may be applied to the soil and optionally incorporated into the soil. In most applications, the effective amount of pesticide is about 75 to 4000 g per hectare, preferably 150 to 3000 g per hectare.

상술한 바와 같이 제조된 피라졸린의 살충 활성은 다음과 같이 평가한다 : 화합물은 10% 아세톤 및 0.25% 옥틸페녹시폴리에톡시 에탄올을 함유하는 수용액중 여러 농도에서 엽(葉)상 시용으로 시험한다. 강남콩작물을 후드내에서 회전 대상에 놓고 시험용액을 분무기로 시용한다. 시험용액을 식물 잎의 윗면과 아랫면에 시용하여 흘러내리도록 한다. 다음에 식물을 건조시키고 줄기의 기부를 떼어낸다. 각 줄기를 종이컵의 물에 넣는다. 적절한 종류의 곤충 10마리씩을 각각의 컵에 넣고 컵을 덮는다. 평가시험에는 남부 거염벌레(Spodoptera eridania), 멕시코콩 딱정벌레(Epilachna varivestis), 비이트 거염벌레(Spodoptera exigua), 및 양배추 자벌레(Trichoplusia ni)를 사용 하였다. 26°에서 4일인 경과한 후 50%RH 치사율을 판단한다. 시험 결과는 표 1에 나타내었다. 해충 치사율은 시험을 훨씬 초기에 판단하는 경우에 일반적으로 적다.The pesticidal activity of the pyrazoline prepared as described above is evaluated as follows: The compound is tested for foliar application at various concentrations in an aqueous solution containing 10% acetone and 0.25% octylphenoxypolyethoxy ethanol. . Place the Gangnam bean crop on the rotating object in the hood and apply the test solution with a nebulizer. The test solution is applied to the top and bottom of the plant leaves and flows down. The plant is then dried and the base of the stem is removed. Place each stem in water in a paper cup. Add 10 insects of the appropriate type to each cup and cover the cup. In the evaluation test, southern larvae (Spodoptera eridania), Mexican bean beetle (Epilachna varivestis), beetle worm (Spodoptera exigua), and cabbage worm (Trichoplusia ni) were used. Determine the 50% RH lethality after 4 days at 26 °. The test results are shown in Table 1. Pest mortality is generally less if the test is judged much earlier.

여러 피라졸린은 또한 토양에 시용하는 경우에 남부 옥수수 뿌리벌레 유충(Diabrotica undecimpunctata howardi Barber)에 대해 활성이 있고, 이러한 시험은 또한 콜로라도 감자 딱정벌레(Leptinotarsa decemlineata say)에 대해 매우 효과적이다.Several pyrazolines are also active against southern corn root larvae (Diabrotica undecimpunctata howardi Barber) when applied to soil, and this test is also very effective against Colorado potato beetle (Leptinotarsa decemlineata say).

[표 1]TABLE 1

엽 상 평 가Leaf evaluation

Figure kpo00030
Figure kpo00030

Figure kpo00031
Figure kpo00031

Figure kpo00032
Figure kpo00032

Figure kpo00033
Figure kpo00033

MBB=멕시코콩 딱정벌레MBB = Mexican Bean Beetle

SAW=남부 거염벌레SAW = Southern Giant Beetle

BAW=비이트 거염벌레BAW = Beat Giant Beetle

CL =양배추 자벌레CL = cabbage insect

Claims (4)

일반식(Ⅱ)의 화합물을 일반식(Ⅲ)의 화합물과 반응시킨 다음, 수득된 생성물을 임의로 알킬화시킴을 특징으로 하여, 일반식(Ｉ-5)의 피라졸린 유도체를 제조하는 방법.A process for preparing a pyrazoline derivative of formula (I-5), characterized by reacting a compound of formula (II) with a compound of formula (III) and then optionally alkylating the product obtained.
Figure kpo00034
Figure kpo00034
 상기식에서 RA는 1,3-벤조디옥솔-5-일이고 ; RB는 일반식
Figure kpo00035
의 4- 또는 5-치환체이며, 여기에서,
Figure kpo00036
는 수소, 염소, 불소, 메틸, 메톡시, 트리플루오로메틸, 및 디플루오로 메톡시 중에서 선택되고 ; RC는 2,3-디하이드로-2,2-디메틸벤조푸란-5-일, 2,3-디하이드로 벤조푸란-5-일, 2,3-디하이드로-2,2,3,3-트리플루오로벤조푸란-5-일, 1,4-벤조디옥산-5-일, 1,4-벤조디옥산-6-일, 2,2-디플루오로벤조디옥솔-5-일, 2,2-디메틸벤조디옥솔-5-일, 2,2-디에틸벤조디옥솔-5-일, 2,2-인단-5-일, 크로만-6-일, 2,2-디메틸크로만-6-일, 2,2,3-트리플루오로-1,4-벤조디옥산-5-일 또는 3-클로로-2,2,3-트리플루오로-1,4-벤조디옥산-5-일이며 ; RN은 수소 또는 메틸이고 ; W는 산소 또는 황이다.In which R A is 1,3-benzodioxol-5-yl; R B is a general formula
Figure kpo00035
Of 4- or 5-substituents, wherein
Figure kpo00036
Is selected from hydrogen, chlorine, fluorine, methyl, methoxy, trifluoromethyl, and difluoro methoxy; R C is 2,3-dihydro-2,2-dimethylbenzofuran-5-yl, 2,3-dihydro benzofuran-5-yl, 2,3-dihydro-2,2,3,3- Trifluorobenzofuran-5-yl, 1,4-benzodioxan-5-yl, 1,4-benzodioxan-6-yl, 2,2-difluorobenzodioxol-5-yl, 2, 2-dimethylbenzodioxol-5-yl, 2,2-diethylbenzodioxol-5-yl, 2,2-indan-5-yl, chroman-6-yl, 2,2-dimethylchroman- 6-yl, 2,2,3-trifluoro-1,4-benzodioxan-5-yl or 3-chloro-2,2,3-trifluoro-1,4-benzodioxane-5- Is work; R N is hydrogen or methyl; W is oxygen or sulfur. 일반식(Ｉ-5)의 피라졸린 유도체Pyrazoline Derivatives of Formula (I-5)
Figure kpo00037
Figure kpo00037
 상기식에서 RA는 1,3-벤조디옥솔-5-일이고 ; RB는 일반식
Figure kpo00038
의 4-또는 5-치환체이며, 여기에서
Figure kpo00039
는 수소, 염소, 불소, 메틸, 메톡시, 트리플루오로메틸, 및 디플루오로메톡시 중에서 선택되고 ; RC는 2,3-디하이드로-2,2-디메틸벤조푸란-5-일, 2,3-디하이드로벤조푸란-5-일, 2,3-디하이드로-2,2,3,3-테트라플루오로벤조푸란-5-일, 1,4-벤조디옥산-5-일, 1,4-벤조디옥산-6-일, 2,2-디플루오로벤조디옥솔-5-일, 2,2-디메틸벤조디옥산-5-일, 2,2-디에틸벤조디옥솔-5-일, 2,2-인단-5-일, 크로만-6-일, 2,2-디메틸크로만-6-일, 2,2,3-트리플루오로-1,4-벤조디옥산-5-일 또는 3-클로로-2,2,3-트리플루오로-벤조디옥산-5-일 이며 ; RN는 수소 또는 메틸이고 ; W는 산소 또는 황이다.In which R A is 1,3-benzodioxol-5-yl; R B is a general formula
Figure kpo00038
Is a 4- or 5-substituent of
Figure kpo00039
Is selected from hydrogen, chlorine, fluorine, methyl, methoxy, trifluoromethyl, and difluoromethoxy; R C is 2,3-dihydro-2,2-dimethylbenzofuran-5-yl, 2,3-dihydrobenzofuran-5-yl, 2,3-dihydro-2,2,3,3- Tetrafluorobenzofuran-5-yl, 1,4-benzodioxan-5-yl, 1,4-benzodioxan-6-yl, 2,2-difluorobenzodioxol-5-yl, 2, 2-dimethylbenzodioxan-5-yl, 2,2-diethylbenzodioxol-5-yl, 2,2-indan-5-yl, chroman-6-yl, 2,2-dimethylchroman- 6-yl, 2,2,3-trifluoro-1,4-benzodioxan-5-yl or 3-chloro-2,2,3-trifluoro-benzodioxan-5-yl; R N is hydrogen or methyl; W is oxygen or sulfur. 제2항에 있어서, RB가 4-치환체인 화합물.The compound of claim 2, wherein R B is 4-substituted. 제2항에 있어서, RB가 일반식
Figure kpo00040
인 그룹인 화합물.The compound of claim 2, wherein R B is a general formula
Figure kpo00040
A compound that is a phosphorus group.
KR1019870010787A 1984-10-25 1987-09-28 Pyrazoline derivatives and the manufacturing process thereof KR880001572B1 (en)

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