Fungicidal nitroaniline substituted pyrazolesThe present invention discloses compounds of formula 1, including all geometric and stereoisomers, tautomers, N-oxides, and salts thereof, wherein R is1、R2、R3、R4、R5、R6M and n are as defined in the disclosure. Also disclosed are compositions containing the compounds of formula 1 and methods for controlling plant diseases caused by fungal pathogens comprising applying an effective amount of a compound or composition of the invention.A compound selected from formula 1, tautomers, n-oxides, and salts thereof,whereinr1is c1-c2an alkyl group;r2is cyano, halogen, c1-c2alkyl or c1-c2a haloalkyl group;r3is halogen or methyl;each r4independently halogen, cyano, nitro, c1-c3alkyl radical, c1-c3alkoxy radicalbase, c1-c3haloalkoxy, c2-c6alkenyloxy radical, c2-c6alkynyloxy, c2-c6cyanoalkoxy group, c2-c6alkoxyalkyl or c2-c6an alkoxy group;each r5independently of one another is halogen, c1-c3alkyl radical, c2-c6alkoxyalkyl group, c1-c3alkoxy radical, c1-c3haloalkoxy, c2-c6alkenyloxy radical, c2-c6alkynyloxy, c2-c6cyanoalkoxy or c2-c6an alkoxy group;m and n are each independently 0, 1,2 or 3;r6is h; or c1-c3alkyl or c1-c3haloalkyl, each of which is optionally substituted with up to 2 independently selected from r6asubstituted with the substituent(s); or amino, c2-c4alkenyl radical, c2-c4alkynyl, c3-c6cycloalkyl, ch (═ o), s (═ o)2om、s(＝o)ur7、(c＝w)r8or or9；each r6aindependently of one another is cyano, c3-c6cycloalkyl radical, c1-c3alkoxy radical, c1-c3haloalkoxy, c1-c3alkylthio radical, c1-c3alkylsulfinyl or c1-c3an alkylsulfonyl group;m is k or na;u is 0, 1 or 2;r7is c1-c3alkyl or c1-c3a haloalkyl group;w is o or s;r8is c1-c3alkyl radical, c2-c4alkoxyalkyl group, c2-c4alkylaminoalkyl, c3-c6dialkylaminoalkyl, c1-c3alkoxy radical, c1-c3alkylthio or c2-c4an alkylthio alkyl group;r9is h; or c1-c3alkyl or c1-c3haloalkyl, each of which is optionally substituted with up to 2 independently selected from r9asubstituted with the substituent(s); or ch (═ o), c3-c6cycloalkyl, s (═ o)2om or (c ═ w) r10；each r9aindependently of one another is cyano, c3-c6cycloalkyl radical, c1-c3alkoxy radical, c1-c3haloalkoxy, c1-c3alkylthio radical, c1-c3alkylsulfinyl or c1-c3an alkylsulfonyl group; and isr10is c1-c3alkyl radical, c2-c4alkoxyalkyl group, c2-c4alkylaminoalkyl, c3-c6dialkylaminoalkyl, c1-c3alkoxy radical, c1-c3alkylthio or c2-c4an alkylthio alkyl group;with the proviso that the compound of formula 1 is not:4- (2, 6-difluoro-4-methoxyphenyl) -n- (2, 4-difluoro-6-nitrophenyl) -1, 3-dimethyl-1h-pyrazol-5-amine;4- (2-chloro-4-fluorophenyl) -1, 3-dimethyl-n- (2-nitrophenyl) -1h-pyrazol-5-amine;4- (2-chloro-4-fluorophenyl) -n- (2, 4-difluoro-6-nitrophenyl) -1, 3-dimethyl-1h-pyrazol-5-amine;4- (2-chloro-4-fluorophenyl) -3-ethyl-1-methyl-n- (2-nitrophenyl) -1h-pyrazol-5-amine;4- (2-chloro-4-fluorophenyl) -1-methyl-n- (2-nitrophenyl) -3- (trifluoromethyl) -1h-pyrazol-5-amine;4- (2, 6-difluoro-4-methoxyphenyl) -n- (2-methoxy-6-nitrophenyl) -1, 3-dimethyl-1h-pyrazol-5-amine;4- (2-chloro-4-fluorophenyl) -n- (2-methoxy-6-nitrophenyl) -1, 3-dimethyl-1h-pyrazol-5-amine;n- (2-chloro-6-nitrophenyl) -4- (2, 6-difluoro-4-methoxyphenyl) -1, 3-dimethyl-1h-pyrazol-5-amine;n- (2-chloro-3-fluoro-6-nitrophenyl) -4- (2, 6-difluoro-4-methoxyphenyl) -1, 3-dimethyl-1h-pyrazol-5-amine;4- (2-chloro-4-fluorophenyl) -1, 3-dimethyl-n- (2-methyl-6-nitrophenyl) -1h-pyrazol-5-amine;n- (2-bromo-4-fluoro-6-nitrophenyl) -4- (2-chloro-4-fluorophenyl) -1, 3-dimethyl-1h-pyrazol-5-amine;4- (2-chloro-4-fluorophenyl) -n- (4-methoxy-2-nitrophenyl) -1, 3-dimethyl-1h-pyrazol-5-amine;4- (2, 6-difluoro-4-methoxyphenyl) -n- (4-fluoro-2-nitrophenyl) -1, 3-dimethyl-1h-pyrazol-5-amine;4- (2, 6-difluoro-4-methoxyphenyl) -n- (4-methoxy-2-nitrophenyl) -1, 3-dimethyl-1h-pyrazol-5-amine;n- (4-chloro-2-nitrophenyl) -4- (2, 6-difluoro-4-methoxyphenyl) -1, 3-dimethyl-1h-pyrazol-5-amine;4- (2, 6-difluoro-4-methoxyphenyl) -1, 3-dimethyl-n- [ 2-nitro-4- (2-propyn-1-yloxy) phenyl ] -1h-pyrazol-5-amine;4- (2, 6-difluoro-4-methoxyphenyl) -1, 3-dimethyl-n- [ 2-nitro-4- (2-propen-1-yloxy) phenyl ] -1h-pyrazol-5-amine;n- (4-bromo-2-nitrophenyl) -4- (2, 6-difluoro-4-methoxyphenyl) -1, 3-dimethyl-1h-pyrazol-5-amine;n- (4-chloro-2-fluoro-6-nitrophenyl) -4- (2, 6-difluoro-4-methoxyphenyl) -1, 3-dimethyl-1h-pyrazol-5-amine;3-chloro-4- (2-chloro-4-fluorophenyl) -n- (2, 4-difluoro-6-nitrophenyl) -1-methyl-1h-pyrazol-5-amine;4- (2, 6-difluoro-4-methoxyphenyl) -1, 3-dimethyl-n- [ 4-methyl-2-nitrophenyl ] -1h-pyrazol-5-amine;4- (2-chloro-4-fluorophenyl) -1, 3-dimethyl-n- (4-methyl-2-nitrophenyl) -1h-pyrazol-5-amine; andn- (4-bromo-2-fluoro-6-nitrophenyl) -4- (2, 6-difluoro-4-methoxyphenyl) -1, 3-dimethyl-1h-pyrazol-5-amine.
살진균 니트로아닐리노 치환된 피라졸모든 기하 및 입체이성질체을 포함하는 하기 화학식 1의 화합물, 그의 호변이성질체, N-옥시드 및 염이 개시된다:[이미지] 여기서 R1, R2, R3, R4, R5, R6, m 및 n은 본 개시내용에 정의된 바와 같다. 화학식 1의 화합물을 함유하는 조성물, 및 유효량의 본 발명의 화합물 또는 조성물을 적용하는 것을 포함하는 진균 병원체에 의해 유발되는 식물 질병을 방제하는 방법이 또한 개시된다.하기 화학식 1로부터 선택되는 화합물, 그의 호변이성질체, N-옥시드, 및 염:[이미지]여기서R1은 C1-C2 알킬이고;R2는 시아노, 할로겐, C1-C2 알킬 또는 C1-C2 할로알킬이고;R3은 할로겐 또는 메틸이고;각각의 R4는 독립적으로 할로겐, 시아노, 니트로, C1-C3 알킬, C1-C3 알콕시, C1-C3 할로알콕시, C2-C6 알케닐옥시, C2-C6 알키닐옥시, C2-C6 시아노알콕시, C2-C6 알콕시알킬 또는 C2-C6 알콕시알콕시이고;각각의 R5는 독립적으로 할로겐, C1-C3 알킬, C2-C6 알콕시알킬, C1-C3 알콕시, C1-C3 할로알콕시, C2-C6 알케닐옥시, C2-C6 알키닐옥시, C2-C6 시아노알콕시 또는 C2-C6 알콕시알콕시이고;m 및 n은 각각 독립적으로 0, 1, 2 또는 3이고;R6은 H; 또는 각각이 R6a로부터 독립적으로 선택된 2개 이하의 치환기로 임의로 치환된 C1-C3 알킬 또는 C1-C3 할로알킬; 또는 아미노, C2-C4 알케닐, C2-C4 알키닐, C3-C6 시클로알킬, CH(=O), S(=O)2OM, S(=O)uR7, (C=W)R8 또는 OR9이고;각각의 R6a는 독립적으로 시아노, C3-C6 시클로알킬, C1-C3 알콕시, C1-C3 할로알콕시, C1-C3 알킬티오, C1-C3 알킬술피닐 또는 C1-C3 알킬술포닐이고;M은 K 또는 Na이고;u는 0, 1 또는 2이고;R7은 C1-C3 알킬 또는 C1-C3 할로알킬이고;W는 O 또는 S이고;R8은 C1-C3 알킬, C2-C4 알콕시알킬, C2-C4 알킬아미노알킬, C3-C6 디알킬아미노알킬, C1-C3 알콕시, C1-C3 알킬티오 또는 C2-C4 알킬티오알킬이고;R9는 H; 또는 각각이 R9a로부터 독립적으로 선택된 2개 이하의 치환기로 임의로 치환된 C1-C3 알킬 또는 C1-C3 할로알킬; 또는 CH(=O), C3-C6 시클로알킬, S(=O)2OM 또는 (C=W)R10이고;각각의 R9a는 독립적으로 시아노, C3-C6 시클로알킬, C1-C3 알콕시, C1-C3 할로알콕시, C1-C3 알킬티오, C1-C3 알킬술피닐 또는 C1-C3 알킬술포닐이고;R10은 C1-C3 알킬, C2-C4 알콕시알킬, C2-C4 알킬아미노알킬, C3-C6 디알킬아미노알킬, C1-C3 알콕시, C1-C3 알킬티오 또는 C2-C4 알킬티오알킬이고;단 화학식 1의 화합물은 하기의 것은 아니다:4-(2,6-디플루오로-4-메톡시페닐)-N-(2,4-디플루오로-6-니트로페닐)-1,3-디메틸-1H-피라졸-5-아민;4-(2-클로로-4-플루오로페닐)-1,3-디메틸-N-(2-니트로페닐)-1H-피라졸-5-아민;4-(2-클로로-4-플루오로페닐)-N-(2,4-디플루오로-6-니트로페닐)-1,3-디메틸-1H-피라졸-5-아민;4-(2-클로로-4-플루오로페닐)-3-에틸-1-메틸-N-(2-니트로페닐)-1H-피라졸-5-아민; 4-(2-클로로-4-플루오로페닐)-1-메틸-N-(2-니트로페닐)-3-(트리플루오로메틸)-1H-피라졸-5-아민;4-(2,6-디플루오로-4-메톡시페닐)-N-(2-메톡시-6-니트로페닐)-1,3-디메틸-1H-피라졸-5-아민;4-(2-클로로-4-플루오로페닐)-N-(2-메톡시-6-니트로페닐)-1,3-디메틸-1H-피라졸-5-아민;N-(2-클로로-6-니트로페닐)-4-(2,6-디플루오로-4-메톡시페닐)-1,3-디메틸-1H-피라졸-5-아민;N-(2-클로로-3-플루오로-6-니트로페닐)-4-(2,6-디플루오로-4-메톡시페닐)-1,3-디메틸-1H-피라졸-5-아민;4-(2-클로로-4-플루오로페닐)-1,3-디메틸-N-(2-메틸-6-니트로페닐)-1H-피라졸-5-아민;N-(2-브로모-4-플루오로-6-니트로페닐)-4-(2-클로로-4-플루오로페닐)-1,3-디메틸-1H-피라졸-5-아민;4-(2-클로로-4-플루오로페닐)-N-(4-메톡시-2-니트로페닐)-1,3-디메틸-1H-피라졸-5-아민;4-(2,6-디플루오로-4-메톡시페닐)-N-(4-플루오로-2-니트로페닐)-1,3-디메틸-1H-피라졸-5-아민;4-(2,6-디플루오로-4-메톡시페닐)-N-(4-메톡시-2-니트로페닐)-1,3-디메틸-1H-피라졸-5-아민;N-(4-클로로-2-니트로페닐)-4-(2,6-디플루오로-4-메톡시페닐)-1,3-디메틸-1H-피라졸-5-아민;4-(2,6-디플루오로-4-메톡시페닐)-1,3-디메틸-N-[2-니트로-4-(2-프로핀-1-일옥시)페닐]-1H-피라졸-5-아민;4-(2,6-디플루오로-4-메톡시페닐)-1,3-디메틸-N-[2-니트로-4-(2-프로펜-1-일옥시)페닐]-1H-피라졸-5-아민;N-(4-브로모-2-니트로페닐)-4-(2,6-디플루오로-4-메톡시페닐)-1,3-디메틸-1H-피라졸-5-아민;N-(4-클로로-2-플루오로-6-니트로페닐)-4-(2,6-디플루오로-4-메톡시페닐)-1,3-디메틸-1H-피라졸-5-아민;3-클로로-4-(2-클로로-4-플루오로페닐)-N-(2,4-디플루오로-6-니트로페닐)-1-메틸-1H-피라졸-5-아민;4-(2,6-디플루오로-4-메톡시페닐)-1,3-디메틸-N-[4-메틸-2-니트로페닐]-1H-피라졸-5-아민;4-(2-클로로-4-플루오로페닐)-1,3-디메틸-N-(4-메틸-2-니트로페닐)-1H-피라졸-5-아민; 및N-(4-브로모-2-플루오로-6-니트로페닐)-4-(2,6-디플루오로-4-메톡시페닐)-1,3-디메틸-1H-피라졸-5-아민.