KR930021607A - Hydrazone derivatives, processes for their preparation, pesticides and / or acaricides containing them as active ingredients, and intermediate compounds thereof - Google Patents

Hydrazone derivatives, processes for their preparation, pesticides and / or acaricides containing them as active ingredients, and intermediate compounds thereof Download PDF

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KR930021607A
KR930021607A KR1019930006859A KR930006859A KR930021607A KR 930021607 A KR930021607 A KR 930021607A KR 1019930006859 A KR1019930006859 A KR 1019930006859A KR 930006859 A KR930006859 A KR 930006859A KR 930021607 A KR930021607 A KR 930021607A
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alkyl
hydrogen
compound
haloalkyl
alkynyl
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KR1019930006859A
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도시아끼 다끼
히로시 기시다
시게루 사이또
신지 이사야마
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모리 히데오
시미또모가가꾸고오교 가부시끼가이샤
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Priority claimed from US07/988,548 external-priority patent/US5378759A/en
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Publication of KR930021607A publication Critical patent/KR930021607A/en

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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C251/00—Compounds containing nitrogen atoms doubly-bound to a carbon skeleton
    • C07C251/72—Hydrazones
    • C07C251/88—Hydrazones having also the other nitrogen atom doubly-bound to a carbon atom, e.g. azines
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N33/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic nitrogen compounds
    • A01N33/26—Biocides, pest repellants or attractants, or plant growth regulators containing organic nitrogen compounds containing nitrogen-to-nitrogen bonds, e.g. azides, diazo-amino compounds, diazonium compounds, hydrazine derivatives
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N35/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having two bonds to hetero atoms with at the most one bond to halogen, e.g. aldehyde radical
    • A01N35/08—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having two bonds to hetero atoms with at the most one bond to halogen, e.g. aldehyde radical at least one of the bonds to hetero atoms is to nitrogen
    • A01N35/10—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having two bonds to hetero atoms with at the most one bond to halogen, e.g. aldehyde radical at least one of the bonds to hetero atoms is to nitrogen containing a carbon-to-nitrogen double bond

Abstract

하기 일반식[Ⅰ]의 히드라존 유도체.Hydrazone derivatives of the general formula [I].

[상기 식에서, R1은 할로겐 등이고, R2는 수소 또는 C1∼C6알킬 등이고, R3는 수소 또는 C1∼C6알킬 등이고, R4는 수소 또는 C1∼C6알킬 등이고, R5는 C1∼C6알킬 등이고, R6는 수소 또는 C1∼C6알킬 등이고, A는 (CH2)t,O, S(0)n, 등이고, a는 1∼4의 정수이고, n은 0∼2의 정수이며, t는 1∼3의 정수이다], 및 그의 제조방법, 활성성분으로서 이를 함유하는 살충제 및/또는 살진드기제, 및 그의 중간체 화합물이 개시되어 있다.[Wherein, R 1 is halogen or the like, R 2 is hydrogen or C 1 -C 6 alkyl or the like, R 3 is hydrogen or C 1 -C 6 alkyl or the like, R 4 is hydrogen or C 1 -C 6 alkyl or the like, R 5 is C 1 -C 6 alkyl or the like, R 6 is hydrogen or C 1 -C 6 alkyl or the like, A is (CH 2 ) t, O, S (0) n, or the like, a is an integer of 1 to 4, n is an integer of 0 to 2, t is an integer of 1 to 3], and methods for preparing the same, pesticides and / or acaricides containing the same as active ingredients, and intermediate compounds thereof are disclosed.

Description

히드라존 유도체, 그의 제조 방법, 활성 성분으로서 이를 함유하는 살충제 및/또는 살진드기제, 및 그의 중간체 화합물Hydrazone derivatives, processes for their preparation, pesticides and / or acaricides containing them as active ingredients, and intermediate compounds thereof

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

Claims (31)

하기 일반식[Ⅰ]의 히드라존 유도체.Hydrazone derivatives of the general formula [I]. [상기 식에서, R1은R7, 할로겐, 시아노, 니트로, 아지드, OR7, S(0)nR7, NR7RB, C(0)R7, CO2R7, C(0)NR7R3, OC(0)R7, OCO2R7, OC(0)NR7RB, NR3C(0)R7, NR8C(0)NR7R8,OSO2R1또는 NR8SO2R7이거나, 또는 a가 1일때, 두개의 R1기는 결합하여 OCH20, OCH2CH2O 또는 CH2CH2O로부터 5― 또는 6-원 고리을 형성하고,이들은 각각 할로겐 또는 메틸로 임의로 치환될 수도 있고, R2는 수소, C1~C6, 알킬, C|1~C6할로알킬, C3~C6시클로알킬, C3~C6시클로알킬 (C1~C4),C2~C6알케닐, C2~C6할로알케닐, C2~C6알키닐, C2~C6할로알키닐, C1~C6알콕시 ː C1~C4) 알킬, C1~C6알킬티오 (C1~C4) 알킬, C2~C6시아노알킬, C1~C6알콕시카르보닐(C1~C4)알킬, OR7, S(0)R7, NR7R3, 시아노, CO2R7, C(0)R7, C(0)NR7R|3, C(S)NR7RB, C(S)R7, C(S)SR7,또는 할로겐, 메틸 또는 트리플루오로메틸로 임의로 치환된 C3~C6시클로알킬이고, R3는 수소, C1~C|6알킬, C1~C6할로알킬, C2~C6알케닐, C2~C6할로알케닐, C2~C6알키닐, C2~C6할로알키닐, C1~C6알콕시( C1~C4)알킬, C1~C6알킬티오-(C1~C4)알킬, C2~C6시아노알킬, Wherein R 1 is R 7 , halogen, cyano, nitro, azide, OR 7 , S (0) nR 7 , NR 7 R B , C (0) R 7 , CO 2 R 7 , C (0 ) NR 7 R 3 , OC (0) R 7 , OCO 2 R 7 , OC (0) NR 7 R B , NR 3 C (0) R 7 , NR 8 C (0) NR 7 R 8 , OSO 2 R or 1, or NR 8 SO 2 R 7, or when a is 1, two R 1 groups bonded to OCH 2 0, OCH 2 CH 2 O or CH 2 CH 2 O from 5- or 6-membered gorieul formed, and these Each may be optionally substituted with halogen or methyl, and R 2 is hydrogen, C 1 -C 6 , alkyl, C | 1 to C 6 haloalkyl, C 3 to C 6 cycloalkyl, C 3 to C 6 cycloalkyl (C 1 to C 4 ) , C 2 to C 6 alkenyl, C 2 to C 6 haloalkenyl, C 2 to C 6 alkynyl, C 2 to C 6 haloalkynyl, C 1 to C 6 alkoxy ː C 1 to C 4 ) alkyl, C 1 to C 6 alkylthio (C 1 to C 4 ) alkyl, C 2 to C 6 Cyanoalkyl, C 1 -C 6 alkoxycarbonyl (C 1 -C 4 ) alkyl, OR 7 , S (0) R 7 , NR 7 R 3 , cyano, CO 2 R 7 , C (0) R 7 , C (0) NR 7 R | 3 , C (S) NR 7 R B , C (S) R 7 , C (S) SR 7 , Or C 3 -C 6 cycloalkyl optionally substituted with halogen, methyl or trifluoromethyl, R 3 is hydrogen, C 1 -C | 6 alkyl, C 1 to C 6 haloalkyl, C 2 to C 6 alkenyl, C 2 to C 6 haloalkenyl, C 2 to C 6 alkynyl, C 2 to C 6 haloalkynyl, C 1 to C 6 Alkoxy (C 1 -C 4 ) alkyl, C 1 -C 6 alkylthio- (C 1 -C 4 ) alkyl, C 2 -C 6 cyanoalkyl, 또는또는 할로겐, 또는 메틸로 임의로 치환된 C1~C5알킬렌이고, 단R2및 R3기는 양 말단에서 결합하여, 고리내에 0∼2개의 산소 또는 황 원자를 함유하는 3- 내지 6- 원 고리를 형성하며, R4는 수소, C1~C6알킬 또는 C1~C6할로알킬이고, R5는 C1~C6알킬, C1~C6할로알킬, C2~C|6알케닐, C2~C6할로알케닐, C2~C6알키닐, C2~C6할로알키닐, C1~C6알콕시(C1~C4)알킬, C1~C6알킬티오(C1~C4)알킬, C1~C6할로알콕시(C1~C4)알킬, C1~C6할로알킬티오(C1~C4)알킬, C2~C6시아노알킬, C2~C6히드록시알킬, C1~C4알킬아미노(C1~C4)알킬, 디(C1~C4)알킬아미노(C1~C4)알킬, C1~C6알킬카르보닐, C1~C6할로알킬카르보닐 또는이고, R6는 수소, C1~C6알킬, C2~C6할로알킬, C2~C6알케닐, C1~C6알콕시(C1~C4)알킬, C2~C6시아노알킬 또는 C2~C6알키닐이거나, 또는 할로겐 또는 메틸로 임의로 치환된 C2~C5알킬렌이고, 단 R5및 R5기는 양 말단에서 결합하여 고리내에 0∼2개의 산소 또는 황 원자를 함유하는 3― 내지 6- 원 고리를 형성하며, R7은 수소, C1~C6알킬, C1~C|6할로알킬, C3~C6시클로알킬 (C1~C4)알킬, C3~C6할로시클로알킬(C1~C4)알킬, C2~C6알케닐, C2~C6할로알케닐, C2~C6알키닐, C2~C6할로알키닐, C1~C|6알콕시(C1~C4)알킬, C1~C6알킬티오(C1~C4)알킬, C1~C6니트로알킬, C2~C6사이노알킬, C1~C6알콕시카르보닐(C1~C4)알킬, C3~C6시클로알킬, C3~C|6할로시클로알킬,또는이고, R8은 수소, C1~C4알킬, C2~C6알케닐 또는 C2~C6알키닐이거나, 또는 할로겐 또는 메틸로 임의로 치환된 C2~C5알킬렌이고, 단 R7및 R8기는 양말단에서 결합하여 고리내에 0∼2개의 산소 또는 황 원자를 함유하는3- 내지 6-원 고리를 형성하며, R9는R7, 할로겐, 시아노, 니트로, 아지드, OR7, S(0)nR|7, NR7R3, C(0)R7, CO2R7, C(O)NR7R8, SO2NR7R8, OC(0)R7,OCO2R7,OC(O)NR|7R8, NR8C(0)R7, NR8C(O)NR7R8, OSO2R7또는 NR8SO2R7이거나, 또는 m이 2일때 2개의 R9기는 결합하여 OCH2O, OCH2CH2O 또는 CH2CH2O로 부터 5- 또는 6― 원 고리를 형성하며, 이들은 각각 할로겐 또는 메틸로 임의로 치환될 수도 있고, R10은 수소, C1~C4알킬,|S(0)nR7, C(0)R7, CO2R7, C(0)NR7R8,C(S)NR|7R8, C(S)R7, P(0) (0R7)2, P(S) (OR7)|2또는 P(O)(R7)(OR7)이고, 단 R10기가 C(0)R7,C(O)NR7R|8및 C(S)NR7R8이외의 어떠한 것일때, R7기는 수소가 아니고, A는 (CH2)t, 산소, S(0)n, NR10, OCH2또는 S(0)nCH2고, 여기에서 각각의 탄소원자에 결합된 수소원자(들)는 할로겐, C1~C6알킬, C3~C|6시클로알킬, C3~C6할로시클로알킬, C3~C6시클로알킬 (C1~C4) 알킬, C2~C4알콕시카르보닐 또는로, 임의로 치환될 수도 있고, W는 할로겐,or Or C 1 -C 5 alkylene optionally substituted with halogen, or methyl, provided that R 2 and R 3 groups are bonded at both ends to contain 3- to 6-membered atoms containing 0 to 2 oxygen or sulfur atoms in the ring; Forming a ring, R 4 is hydrogen, C 1 -C 6 alkyl or C 1 -C 6 haloalkyl, R 5 is C 1 -C 6 alkyl, C 1 -C 6 haloalkyl, C 2 -C | 6 alkenyl, C 2 to C 6 haloalkenyl, C 2 to C 6 alkynyl, C 2 to C 6 haloalkynyl, C 1 to C 6 alkoxy (C 1 to C 4 ) alkyl, C 1 to C 6 Alkylthio (C 1 -C 4 ) alkyl, C 1 -C 6 haloalkoxy (C 1 -C 4 ) alkyl, C 1 -C 6 haloalkylthio (C 1 -C 4 ) alkyl, C 2 -C 6 Noalkyl, C 2 -C 6 hydroxyalkyl, C 1 -C 4 alkylamino (C 1 -C 4 ) alkyl, di (C 1 -C 4 ) alkylamino (C 1 -C 4 ) alkyl, C 1- C 6 alkylcarbonyl, C 1 to C 6 haloalkylcarbonyl or R 6 is hydrogen, C 1 -C 6 alkyl, C 2 -C 6 haloalkyl, C 2 -C 6 alkenyl, C 1 -C 6 alkoxy (C 1 -C 4 ) alkyl, C 2 -C 6 Cyanoalkyl or C 2 to C 6 alkynyl, or C 2 to C 5 alkylene optionally substituted with halogen or methyl, provided that R 5 and R 5 groups are bonded at both ends to form 0-2 oxygen or A 3- to 6-membered ring containing a sulfur atom, R 7 is hydrogen, C 1 -C 6 alkyl, C 1 -C | 6 haloalkyl, C 3 to C 6 cycloalkyl (C 1 to C 4 ) alkyl, C 3 to C 6 halocycloalkyl (C 1 to C 4 ) alkyl, C 2 to C 6 alkenyl, C 2 to C 6 Haloalkenyl, C 2 to C 6 alkynyl, C 2 to C 6 haloalkynyl, C 1 to C | 6 alkoxy (C 1 -C 4 ) alkyl, C 1 -C 6 alkylthio (C 1 -C 4 ) alkyl, C 1 -C 6 nitroalkyl, C 2 -C 6 cyanoalkyl, C 1 -C 6 alkoxy Carbonyl (C 1 -C 4 ) alkyl, C 3 -C 6 cycloalkyl, C 3 -C | 6 halocycloalkyl, or R 8 is hydrogen, C 1 -C 4 alkyl, C 2 -C 6 alkenyl or C 2 -C 6 alkynyl, or C 2 -C 5 alkylene optionally substituted with halogen or methyl, provided that The 7 and R 8 groups are bonded at the end of the ring to form a 3- to 6-membered ring containing 0-2 oxygen or sulfur atoms in the ring, R 9 is R 7 , halogen, cyano, nitro, azide, OR 7 , S (0) nR | 7 , NR 7 R 3 , C (0) R 7 , CO 2 R 7 , C (O) NR 7 R 8 , SO 2 NR 7 R 8 , OC (0) R 7 , OCO 2 R 7 , OC (O ) NR | 7 R 8 , NR 8 C (0) R 7 , NR 8 C (O) NR 7 R 8 , OSO 2 R 7 or NR 8 SO 2 R 7 , or when m is 2, two R 9 groups combine to form OCH Form a 5- or 6-membered ring from 2 O, OCH 2 CH 2 O or CH 2 CH 2 O, which may be optionally substituted with halogen or methyl, respectively, R 10 is hydrogen, C 1 -C 4 alkyl , | S (0) nR 7 , C (0) R 7 , CO 2 R 7 , C (0) NR 7 R 8 , C (S) NR | 7 R 8 , C (S) R 7 , P (0) (0R 7 ) 2 , P (S) (OR 7 ) | 2 or P (O) (R 7 ) (OR 7 ) provided that the R 10 groups are C (0) R 7 , C (O) NR 7 R | When any other than 8 and C (S) NR 7 R 8 , the R 7 group is not hydrogen and A is (CH 2 ) t, oxygen, S (0) n, NR 10 , OCH 2 or S (0) nCH 2 , wherein the hydrogen atom (s) bonded to each carbon atom is halogen, C 1 -C 6 alkyl, C 3 -C | 6 cycloalkyl, C 3 -C 6 halocycloalkyl, C 3 -C 6 cycloalkyl (C 1 -C 4 ) alkyl, C 2 -C 4 alkoxycarbonyl or May be optionally substituted, W is halogen, 시아노, 니트로, C1~C2알킬, C1~C2할로알킬, C1~C|2알콕시, C1~C2할로알콕시, C1~C2알킬티오, C1~C2할로알킬티오, C1~C2알킬술포닐 또는 C1~C2할로알킬술포닐이고, a는 1∼4의 정수이고, m은 0∼3의 정수이고, t는 1∼3의 정수이고, n은 0∼2의 정수이며, p는 0~5의 정수이다]Cyano, nitro, C 1 -C 2 alkyl, C 1 -C 2 haloalkyl, C 1 -C | 2 alkoxy, C 1 -C 2 haloalkoxy, C 1 -C 2 alkylthio, C 1 -C 2 haloalkylthio, C 1 -C 2 alkylsulfonyl or C 1 -C 2 haloalkylsulfonyl, a is Is an integer of 1 to 4, m is an integer of 0 to 3, t is an integer of 1 to 3, n is an integer of 0 to 2, and p is an integer of 0 to 5] 제1항에 있어서, A가 CH2, CH2CH2, 산소, 황, NR10, OCH2또는 SCH2(여기에서, 각각의 탄소원자에 결합된 수소원자(들)은 C1~C6알킬 또는로 임의로 치환될 수도 있다)인 히드라존 유도체.The compound of claim 1, wherein A is CH 2 , CH 2 CH 2 , oxygen, sulfur, NR 10 , OCH 2 or SCH 2 , wherein the hydrogen atom (s) bonded to each carbon atom is C 1 to C 6 Alkyl or Hydrazone derivative. 제2항에 있어서, R1및 R9가 각각 독립적으로 R7, 할로겐, 시아노, 니트로, OR7, SR7또는 NR7R8이거나,또는 a 또는 m이 2일때 2개 R1또는 R9기가 결합하여 OCH20, OCH2CH2O 또는 CH2CH2O로 부터 5- 또는 6―원고리를 형성하고, 이들은 각각 할로겐 또는 메틸로 임의로 치환될 수도 있고, R2는 수소, C1~C6알킬, C1~C6할로알킬, C3~C6시클로알킬, C3~C6시클로알킬(C1~C4)알킬, C3~C6알케닐, C3~C6할로알케닐, C3~C6알키닐, C3~C6할로알키닐, C1~C6알콕시(C1~C4)알킬, C1~C6알킬티오( C1~C4) 알킬, C2~C6시아노알킬, CO2R7, C(O)NR7R8 이거나, 또는 할로겐, 메틸 또는 트리플루오로메틸로 임의로 치환된 C3~C6시클로알킬이고, R3는 수소, C1~C6알킬, C1~C6할로알킬, C3~C6알케닐, C3~C6할로알케닐, C3~C6알키닐, C3~C6할로알키닐, C1~C6알콕시 (C1~C4)알킬, C1~C6알킬티오(C1~C4)알킬,C2~C6시아노알킬,,또는 할로겐 또는, 메틸로 임의로 치환된 C1~C5알킬렌이고, 단 R2및 R3기는 양 말단에서 결합하여 고리내에 0 또는 1개의 산소 또는 황원자를 함유하는 3― 내지 6―원 고리를 형성하며, R4는 수소, C1~C6알킬 또는 C1~C6할로알킬이고, R5는 C1~C6알킬, C1~C|6할로알킬, C3~C6알케닐, C3~C6할로알케닐, C3~C6알키닐, C3~C6할로알키닐, C1~C6알콕시(C1~C6)알킬, C1~C6일킬티오(C1~C4)알킬, C1~C6할로알콕시 (C1~C4)알킬, C1~C6할로알킬티오(C1~C4) 알킬, C2~C6시아노알킬, C2~C6히드록시알킬, C1~C4알킬아미노(C1~C|4)알킬 또는 디(C1~C4)알킬아미노(C1~C4)알킬이고, R6는 수소, C1~C6알킬, C2~C6할로알킬, C3~C6알케닐 또는 C3~C6알키닐, C1~C6알콕시 (C1~C4)알킬, 또는 메틸로 임의로 치환되는 C2~C5알킬렌이고, 단 R5및 R6기는 양 말단에서 결합하여 고리내에 0∼2개의 산소 또는 황 원자를 함유하는 3― 내지 6- 원 고리를 형성하고, R7은 수소, C1~C6알킬, C1~C6할로알킬, C3~C4알케닐, C3~C4알키닐, C1~C6알콕시(C1~C4)알킬, C1~C6알킬티오(C1~C4)알킬,또는 -CH2 이고, R8은 수소, C1~C4알킬, C3~C4알케닐 또는 C3~C4알키닐이거나, 또는 할로겐 또는 메틸로 임의로 치환되는 C1~C|5알킬렌이고, 단 R7및 R8기는 양 말단에서 결합하여 고리내에 0∼1개의 산소 또는 황원자를 함유하는 3- 내지 6- 원 고리를 형성하며, R10은 수소, C1~C4알킬,|C(0)R7, CO2R7또는 C(0)NR7R8이고, 단 R10기가 CO2R7일때 R7기는 수소가 아니며, W는 할로겐, 시아노, 니트로 C1~C2알킬, C1~C2할로알킬, C1~C2알콕시, C1~C2할로알콕시 또는 C1~C2알킬티오이고, a는 1∼2의 정수이고, m은 0∼2의 정수이고, n은 0∼2의 정수이며, p는 0∼2의 정수인 히드라존 유도체.The compound of claim 2, wherein R 1 and R 9 are each independently R 7 , halogen, cyano, nitro, OR 7 , SR 7 or NR 7 R 8 , or two R 1 or R when a or m is 2 9 group is bonded to OCH 2 0, OCH 2 CH 2 O or CH 2 CH 2 O and may be optionally substituted with a 5- or 6-membered from halogen or methyl, and each of which may form a ring, R 2 is hydrogen, C 1 to C 6 alkyl, C 1 to C 6 haloalkyl, C 3 to C 6 cycloalkyl, C 3 to C 6 cycloalkyl (C 1 to C 4 ) alkyl, C 3 to C 6 alkenyl, C 3 to C 6 haloalkenyl, C 3 to C 6 alkynyl, C 3 to C 6 haloalkynyl, C 1 to C 6 alkoxy (C 1 to C 4 ) alkyl, C 1 to C 6 alkylthio (C 1 to C 4 ) Alkyl, C 2 to C 6 cyanoalkyl, CO 2 R 7 , C (O) NR 7 R 8 Or C 3 -C 6 cycloalkyl optionally substituted with halogen, methyl or trifluoromethyl, R 3 is hydrogen, C 1 -C 6 alkyl, C 1 -C 6 haloalkyl, C 3 -C 6 eggs Kenyl, C 3 to C 6 haloalkenyl, C 3 to C 6 alkynyl, C 3 to C 6 haloalkynyl, C 1 to C 6 alkoxy (C 1 to C 4 ) alkyl, C 1 to C 6 alkylthio (C 1 -C 4 ) alkyl, C 2 -C 6 cyanoalkyl, Or halogen or C 1 -C 5 alkylene optionally substituted with methyl, provided that R 2 and R 3 groups are bonded at both ends to contain 3- or 6-membered rings containing 0 or 1 oxygen or sulfur atom in the ring; Wherein R 4 is hydrogen, C 1 -C 6 alkyl or C 1 -C 6 haloalkyl, R 5 is C 1 -C 6 alkyl, C 1 -C | 6 haloalkyl, C 3 to C 6 alkenyl, C 3 to C 6 haloalkenyl, C 3 to C 6 alkynyl, C 3 to C 6 haloalkynyl, C 1 to C 6 alkoxy (C 1 to C 6 ) alkyl, C 1 ~ C 6 ilkil thio (C 1 ~ C 4) alkyl, C 1 ~ C 6 haloalkoxy (C 1 ~ C 4) alkyl, C 1 ~ C 6 haloalkylthio (C 1 ~ C 4) Alkyl, C 2 -C 6 cyanoalkyl, C 2 -C 6 hydroxyalkyl, C 1 -C 4 alkylamino (C 1 -C | 4 ) alkyl or di (C 1 -C 4 ) alkylamino (C 1 C 6 ) alkyl, R 6 is hydrogen, C 1 -C 6 alkyl, C 2 -C 6 haloalkyl, C 3 -C 6 alkenyl or C 3 -C 6 alkynyl, C 1 -C 6 alkoxy ( C 1 -C 4 ) alkyl, or C 2 -C 5 alkylene optionally substituted with methyl, provided that R 5 and R 6 groups are bonded at both ends to contain 3-2 oxygen or sulfur atoms in the ring; To 6-membered ring, R 7 is hydrogen, C 1 -C 6 alkyl, C 1 -C 6 haloalkyl, C 3 -C 4 alkenyl, C 3 -C 4 alkynyl, C 1 -C 6 Alkoxy (C 1 -C 4 ) alkyl, C 1 -C 6 alkylthio (C 1 -C 4 ) alkyl, Or -CH 2 And R 8 is hydrogen, C 1 -C 4 alkyl, C 3 -C 4 alkenyl or C 3 -C 4 alkynyl, or C 1 -C | optionally substituted with halogen or methyl; 5 alkylene, provided that R 7 and R 8 groups are bonded at both ends to form a 3- to 6-membered ring containing 0 to 1 oxygen or sulfur atom in the ring, R 10 is hydrogen, C 1 to C 4 Alkyl, | C (0) R 7 , CO 2 R 7 or C (0) NR 7 R 8 , provided that when the R 10 group is CO 2 R 7 the R 7 group is not hydrogen, W is halogen, cyano, nitro C 1 -C 2 alkyl, C 1 -C 2 haloalkyl, C 1 -C 2 alkoxy, C 1 -C 2 haloalkoxy or C 1 -C 2 alkylthio, a is an integer of 1-2, m is 0-2 An integer, n is an integer of 0-2, p is an integer of 0-2, a hydrazone derivative. 제3항에 있어서, R1및 R9가 각각 독립적으로 R7, 할로겐, 시아노, 니트로 또는 OR7이거나, a 또는 m이 2일때, 2개의 R1또는 R9기가 결합하여 OCH2O로 부터 5― 원 고리를 형성하고 이는 할로겐 또는 메틸로 임의로 치환될 수도 있으며, R2는 수소, C1~C6알킬, C1~C6할로알킬, C3~C4알케닐, C3~C4알키닐, C2~C6시아노알킬,CO2R7 이고, R3는 수소, C1~C6알킬, C1~C6할로알킬, C3~C6알케닐, C3~C6알키닐 또는 C2~C|6시아노알킬이거나, 또는 메틸로 임의로 치환되는 C1~C5알킬렌이고, 단 R2및 R3기는 양 말단에서 결합하여 고리내에 0 또는 1개의 산소 또는 황 원자를 함유하는 3- 내지 6- 원 고리를 형성하고, R4는 수소 또는 C1~C6알킬이고, R5는 C1~C6알킬, C1~C6할로알킬, C3~C6알케닐, C3~C6알키닐, C1~C6알콕시 (C1~C4)알킬, C2~C6시아노알킬, C2~C6히드록시알킬, C1~C4알킬아미노(C1~C4)알킬 또는 디(C1~C4)알킬아미노(C1~C|4)알킬이고, R6는 수소, C1~C6알킬, C2~C6할로알킬, C3~C6알케닐, C3~C6알키닐 또는 C1~C6알콕시 (C1~C4)알킬이거나, 또는 메틸로 임의로 치환되는 C2~C5알킬렌이고, 단 R5및 R6기는 양 말단에서 결합하여 고리내에 0∼1개의 산소 또는 황 원자를 함유하는 3- 내지 6- 원 고리를 형성하며, R7은 수소, C1~C3알킬 또는 C1~C3할로알킬이고, R10은 수소, C1~C4알킬 또는 (C1~C4알콕시)카르보닐인 히드라존 유도체.The compound of claim 3, wherein R 1 and R 9 are each independently R 7 , halogen, cyano, nitro or OR 7 , or when a or m is 2, two R 1 or R 9 groups are bonded to OCH 2 O. To 5-membered ring, which may be optionally substituted with halogen or methyl, R 2 is hydrogen, C 1 -C 6 alkyl, C 1 -C 6 haloalkyl, C 3 -C 4 alkenyl, C 3- C 4 alkynyl, C 2 -C 6 cyanoalkyl, CO 2 R 7 And R 3 is hydrogen, C 1 -C 6 alkyl, C 1 -C 6 haloalkyl, C 3 -C 6 alkenyl, C 3 -C 6 alkynyl or C 2 -C | 6 cyanoalkyl, or C 1 -C 5 alkylene optionally substituted with methyl, provided that R 2 and R 3 groups are bonded at both ends to contain 3- or 6 oxygen or sulfur atoms in the ring -Form a ring, R 4 is hydrogen or C 1 -C 6 alkyl, R 5 is C 1 -C 6 alkyl, C 1 -C 6 haloalkyl, C 3 -C 6 alkenyl, C 3 -C 6 alkynyl, C 1 -C 6 alkoxy (C 1 -C 4 ) alkyl, C 2 -C 6 cyanoalkyl, C 2 -C 6 hydroxyalkyl, C 1 -C 4 alkylamino (C 1 -C 4 ) Alkyl or di (C 1 -C 4 ) alkylamino (C 1 -C | 4 ) alkyl, R 6 is hydrogen, C 1 -C 6 alkyl, C 2 -C 6 haloalkyl, C 3 -C 6 eggs Is kenyl, C 3 -C 6 alkynyl or C 1 -C 6 alkoxy (C 1 -C 4 ) alkyl, or C 2 -C 5 alkylene optionally substituted with methyl, provided that R 5 and R 6 groups are both terminal and combine to form a 3-to 6-membered ring containing 0 to 1 oxygen atoms or sulfur atoms in the ring from, R 7 is hydrogen, C 1 ~ C 3 alkyl in C 1 ~ C 3 haloalkyl, R 10 is hydrogen, C 1 ~ C 4 alkyl or (C 1 ~ C 4 alkoxy) carbonyl is a hydrazone derivative. 제4항에 있어서, A가 CH2, CH2CH2, 산소, 황, NR10또는 SCH|2이고, 여기에서 CH2및 CH2CH2의 각각의 탄소원자에 결합된 수소 원자(들)는 임의로 메틸 또는으로 치환될 수도 있고, 단, A가 산소, 황 또는 NR10일때, R2및 R3의 각각은이외의 어느 하나인 히드라존 유도체.The process of claim 4, wherein A is CH 2 , CH 2 CH 2 , oxygen, sulfur, NR 10 or SCH | 2 , wherein the hydrogen atom (s) bonded to each carbon atom of CH 2 and CH 2 CH 2 are optionally methyl or Provided that when A is oxygen, sulfur or NR 10 , each of R 2 and R 3 Hydrazone derivative which is any other than. 제5항 있어서, R1, R9및 W의 각각은 독립적으로 수소, 메틸, 트리플루오로메틸, 불소, 염소, 브롬, 시아노, 메톡시, 트리플루오로메톡시 또는 디플루오로메톡시이거나, 또는 a 또는 m이 2일때, 2개의 R1또는 R9기는 메틸렌디옥시 또는 디플루오로메틸렌디옥시이고, R2는 수소, C1~C6알킬, C1~C6할로알킬, C3~C4알케닐, C3~C4알키닐,이고, R3는 수소, C1~C2알킬, C3~C4알케닐 또는 C3~C4알키닐이거나, 또는 C4~C5알킬렌이고, 단, R2및 R3기는 양 말단에서 결합하여 5- 내지 6- 원 고리를 형성하고, R4는 수소 또는 C1~C6알킬이고, R5는 C1~C6알킬, C3~C4알케닐, C3~C4알키닐 또는 C1~C3알콕시(C1~C3)알킬인 히드라존 유도체.The compound of claim 5, wherein each of R 1 , R 9 and W is independently hydrogen, methyl, trifluoromethyl, fluorine, chlorine, bromine, cyano, methoxy, trifluoromethoxy or difluoromethoxy, or When a or m is 2, two R 1 or R 9 groups are methylenedioxy or difluoromethylenedioxy, and R 2 is hydrogen, C 1 -C 6 alkyl, C 1 -C 6 haloalkyl, C 3- C 4 alkenyl, C 3 to C 4 alkynyl, R 3 is hydrogen, C 1 -C 2 alkyl, C 3 -C 4 alkenyl or C 3 -C 4 alkynyl or C 4 -C 5 alkylene, provided that R 2 and R 3 groups are positive Bond at the end to form a 5- to 6-membered ring, R 4 is hydrogen or C 1 -C 6 alkyl, R 5 is C 1 -C 6 alkyl, C 3 -C 4 alkenyl, C 3 -C A hydrazone derivative that is 4 alkynyl or C 1 -C 3 alkoxy (C 1 -C 3 ) alkyl. 제6항에 있어서, A가 CH2또는 CH2CH2이고, 여기에서 각각의 탄소원자에 결합된 수소원자(들)가 임의로 메틸 또는로 치환될 수도 있는 히드라존 유도체.The compound of claim 6, wherein A is CH 2 or CH 2 CH 2 , wherein the hydrogen atom (s) bonded to each carbon atom is optionally methyl or Hydrazone derivatives which may be substituted with. 제6항에 있어서, A가 산소, 황 또는 NR10이고, R2및 R3가 각각이외의 어느 하나인 히드라존 유도체.The compound of claim 6, wherein A is oxygen, sulfur or NR 10 , and R 2 and R 3 are each Hydrazone derivative which is any other than. 제6항에 있어서, A가 SCH2인 히드라존 유도체.The hydrazone derivative according to claim 6 wherein A is SCH 2 . 제6항에 있어서, A가 CH2인 히드라존 유도체.The hydrazone derivative according to claim 6 wherein A is CH 2 . 제6항에 있어서, A가인 히드라존 유도체.A compound according to claim 6 wherein A is Phosphorus hydrazone derivatives. 제10항에 있어서, R2가 C1~C6알킬, 알릴, 프로파르길 또는이고, R3가 수소 또는 C1~C3알킬 : 또는 C4~C5알킬렌이고, 단, R2및 R3기는 양 말단에서 결합하여 5― 또는 6- 원고리를 형성하며, R4는 수소 또는 C1~C4알킬이고, R5는 C1~C6알킬, 아릴 또는 프로파르길이고, R6는 C1~C6알킬인 히드라존 유도체.The compound of claim 10, wherein R 2 is C 1 -C 6 alkyl, allyl, propargyl or R 3 is hydrogen or C 1 -C 3 alkyl: or C 4 -C 5 alkylene, provided that R 2 and R 3 groups are bonded at both ends to form a 5- or 6-membered ring, R 4 Is a hydrogen or C 1 -C 4 alkyl, R 5 is C 1 -C 6 alkyl, aryl or propargyl, and R 6 is C 1 -C 6 alkyl. 제12항에 있어서, R1,R9및 W가 각각 독립적으로 수소, 메틸, 불소, 염소, 브롬, 메톡시 또는 디플루오로메톡시인 히드라존 유도체.13. The hydrazone derivative according to claim 12, wherein R 1 , R 9 and W are each independently hydrogen, methyl, fluorine, chlorine, bromine, methoxy or difluoromethoxy. 제11항에 있어서, R2및 R3가 각각 독립적으로 수소 또는 C1~C4알킬이고, R4가 수소 또는 C1~C6알킬이고, R5가 C1~C6알킬, 알릴 또는 프로파르길이며, R6가 C1~C6알킬인 히드라존 유도체.12. The compound of claim 11, wherein R 2 and R 3 are each independently hydrogen or C 1 -C 4 alkyl, R 4 is hydrogen or C 1 -C 6 alkyl, and R 5 is C 1 -C 6 alkyl, allyl or A hydrazone derivative wherein propargyl is R 6 is C 1 -C 6 alkyl. 제14항에 있어서, R1및 W가 각각 독립적으로 수소, 메틸, 불소, 염소, 브롬, 메톡시 또는 디플루오로메톡시인 히드라존 유도체.The hydrazone derivative according to claim 14, wherein R 1 and W are each independently hydrogen, methyl, fluorine, chlorine, bromine, methoxy or difluoromethoxy. 하기 식의 화합물 :Compound of the formula 하기 식의 화합물:Compound of the formula 하기 식의 화합물:Compound of the formula 하기 식의 화합물:Compound of the formula [상기 식에서, R1, R2, R3, A 및 a는 각각 제1항에 정의된 바와 같다]의 화합물을 하기 일반식 :Wherein R 1 , R 2 , R 3 , A and a are each as defined in claim 1. [상기식에서, R4, R5및 R6는 각각 제1항에 정의된 바와 같고; R은 C1∼C4알킬이다]의 화합물과 반응시킴을 특징으로 하는 하기 일반식 :[Wherein R 4 , R 5 and R 6 are each as defined in claim 1; R is C 1 -C 4 alkyl]. [상기 식에서, R1, R2, R3, R4, R5, R6, A 및 a는 각각 제1항에 정의된 바와 같다]의 히드라존 유도체의 제조방법.Wherein R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , A and a are as defined in claim 1, respectively. 하기 일반식:General formula: [상기식에서, R1, R2, R3, R4, A 및 a는 각각 제1항에 정의된 바와 같다]의 화합물을 하기 일반식 :Wherein R 1 , R 2 , R 3 , R 4 , A and a are each as defined in claim 1. [상기 식에서, R5및 R6는 각각 제1항에 정의된 바와 같다]의 아민 화합물과 반응시킴을 특징으로 하는 하기 일반식 :Wherein R 5 and R 6 are each as defined in claim 1, and react with an amine compound of the general formula [상기식에서, R1, R2, R3, R4, R5, R6, A 및 a는 각각 제1항에 정의된 바와 같다]의 히드라존 유도체의 제조방법.Wherein R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , A and a are as defined in claim 1, respectively. 하기 일반식:General formula: [상기식에서, R1, R2, R3, A 및 a는 각각 제1항에 정의된 바와 같다]의 화합물을 하기 일반식 :Wherein R 1 , R 2 , R 3 , A and a are each as defined in claim 1. [상기식에서, R4, R5및 R6는 각각 제1항에 정의된 바와 같다]의 화합물과 반응시킴을 특징으로 하는 하기 일반식:Wherein R 4 , R 5 and R 6 are each as defined in claim 1, wherein the compound is reacted with [상기식에서, R1, R2, R3, R4, R5, R6,A 및 a는 각각 제1항에 정의된 바와 같다]의 히드라존 유도체 또는 농업적으로 허용 가능한 그의 염의 제조방법.A process for preparing a hydrazone derivative or an agriculturally acceptable salt thereof, wherein R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , A and a are each as defined in claim 1. . 활성 성분으로서의 제1항에 따른 히드라존 유도체 및 불활성 캐리어를 함유하는 살충 및/또는 살진드기 조성물.Insecticidal and / or acaricide composition containing the hydrazone derivative according to claim 1 as an active ingredient and an inert carrier. 제1항에 따른 히드라존 유도체의 살충 또는 살진드기 유효량을 해충 및/또는 진드기가 서식하는 지역에 살포함을 특징으로 하는 해충 및/또는 진드기의 방제방법.A method for controlling insect pests and / or mites by spraying the pesticide and / or mite effective amount of the hydrazone derivative according to claim 1 to an area where pests and / or mites live. 제1항에 따른 히드라존 유도체의 살충제 및/또는 살진드기제로서의 용도.Use of the hydrazone derivatives according to claim 1 as insecticides and / or mites. 하기 식의 화합물 :Compound of the formula [상기식에서, R1, R2, R3, R4, A 및 a는 각각 제1항에 정의된 바와 같다][Wherein R 1 , R 2 , R 3 , R 4 , A and a are as defined in claim 1, respectively] 제25항에 있어서, R1, R2, R3, R4, A 및 a가 각각 제5항에 정의된 바와 같은 화합물.The compound of claim 25, wherein R 1 , R 2 , R 3 , R 4 , A and a are each as defined in claim 5. 제25항에 있어서, R1, R2, R3, R4, A 및 a가 각가 제7항에 정의된 바와 같은 화합물.The compound of claim 25, wherein R 1 , R 2 , R 3 , R 4 , A and a are each as defined in claim 7. 제25항에 있어서, R1, R2, R3, R4,A 및 a가 각가 제10항에 정의된 바와 같은 화합물.The compound of claim 25, wherein R 1 , R 2 , R 3 , R 4 , A and a are each as defined in claim 10. 제25항에 있어서, R1, R2, R3, R4,A 및 a가 각가 제12항에 정의된 바와 같은 화합물.The compound of claim 25, wherein R 1 , R 2 , R 3 , R 4 , A and a are each as defined in claim 12. 제25항에 있어서, R1, R2, R3, R4, A 및 a가 각가 제13항에 정의된 바와 같은 화합물.The compound of claim 25, wherein R 1 , R 2 , R 3 , R 4 , A and a are each as defined in claim 13. 하기 일반식의 화합물.Compound of the following general formula. ※ 참고사항 : 최초출원 내용에 의하여 공개하는 것임.※ Note: The disclosure is based on the initial application.
KR1019930006859A 1992-04-23 1993-04-23 Hydrazone derivatives, processes for their preparation, pesticides and / or acaricides containing them as active ingredients, and intermediate compounds thereof KR930021607A (en)

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