KR20010042147A - Fungicide Mixtures Based on Triple Oxime Ether Derivatives and Rhizoctonia Fungicides - Google Patents
Fungicide Mixtures Based on Triple Oxime Ether Derivatives and Rhizoctonia Fungicides Download PDFInfo
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Abstract
본 발명은 활성 성분으로서 a) 하기 화학식 I(식중, 치환체 및 지수는 발명의 상세한 설명에 언급된 의미를 가짐)의 페닐아세트산 유도체 및 그의 염, 및 b) 하기 화학식 II 내지 화학식 VII의 화합물중 1종 이상을 상승작용 유효량으로 포함하는 살진균제 혼합물에 관한 것이다.The present invention relates to the active ingredient a) phenylacetic acid derivatives of the formula I (wherein substituents and indices have the meanings mentioned in the detailed description of the invention) and salts thereof, and b) compounds of formulas II to VII A fungicide mixture comprising at least a species in a synergistically effective amount.
〈화학식 I〉<Formula I>
〈화학식 II〉<Formula II>
〈화학식 III〉<Formula III>
〈화학식 IV〉<Formula IV>
〈화학식 V〉<Formula V>
〈화학식 VI〉<Formula VI>
〈화학식 VII〉<Formula VII>
Description
본 발명은 a) 하기 화학식 I의 페닐아세트산 유도체 및 그의 염, 및 b) 하기 화학식 II 내지 화학식 VII의 살진균제중에서 선택된 1종 이상의 살진균제를 포함하는, 유해 진균을 방제하기 위한 살진균성 혼합물에 관한 것이다:The present invention relates to a fungicidal mixture for controlling harmful fungi comprising a) a phenylacetic acid derivative of formula (I) and a salt thereof and b) at least one fungicide selected from fungicides of formulas (II) to (VII) will be:
상기 식에서,Where
X는 NOCH3, CHOCH3또는 CHCH3이고,X is NOCH 3 , CHOCH 3 or CHCH 3 ,
Y는 산소 또는 NR이고,Y is oxygen or NR,
R1, R은 서로 독립적으로 각각 수소 또는 C1-C4-알킬이고,R 1 , R are each independently of the other hydrogen or C 1 -C 4 -alkyl,
R2는 시아노, 니트로, 트리플루오로메틸, 할로겐, C1-C4-알킬 또는 C1-C4-알콕시이고,R 2 is cyano, nitro, trifluoromethyl, halogen, C 1 -C 4 -alkyl or C 1 -C 4 -alkoxy,
m은 0, 1 또는 2이고, m이 2인 경우 라디칼 R2는 상이할 수도 있고,m is 0, 1 or 2, and when m is 2 the radicals R 2 may be different,
R3은 수소, 시아노, C1-C4-알킬, C1-C4-할로알킬 또는 C3-C6-시클로알킬이고,R 3 is hydrogen, cyano, C 1 -C 4 -alkyl, C 1 -C 4 -haloalkyl or C 3 -C 6 -cycloalkyl,
R4, R6은 서로 독립적으로 각각 수소이거나,R 4 , R 6 are each independently hydrogen,
C1-C10-알킬, C3-C6-시클로알킬, C2-C10-알케닐, C2-C10-알키닐, C1-C10-알킬카르보닐, C2-C10-알케닐카르보닐, C3-C10-알키닐카르보닐 또는 C1-C10-알킬술포닐이고, 이들 라디칼은 부분적으로 또는 완전히 할로겐화될 수 있거나, 또는 시아노, 니트로, 히드록실, 메르캅토, 아미노, 카르복실, 아미노카르보닐, 아미노티오카르보닐, 할로겐, C1-C6-알킬, C1-C6-할로알킬, C1-C6-알킬술포닐, C1-C6-알킬술폭실, C1-C6-알콕시, C1-C6-할로알콕시, C1-C6-알콕시카르보닐, C1-C6-알킬티오, C1-C6-알킬아미노, 디-C1-C6-알킬아미노, C1-C6-알킬아미노카르보닐, 디-C1-C6-알킬아미노카르보닐, C1-C6-알킬아미노티오카르보닐, 디-C1-C6-알킬아미노티오카르보닐, C2-C6-알케닐, C2-C6-알케닐옥시, C3-C6-시클로알킬, C3-C6-시클로알킬옥시, 헤테로시클릴, 헤테로시클릴옥시, 벤질, 벤질옥시, 아릴, 아릴옥시, 아릴티오, 헤타릴, 헤타릴옥시 및 헤타릴티오의 기들중 1 내지 3개를 가질 수 있으며, 이때 환상 기들 자체는 부분적으로 또는 완전히 할로겐화될 수 있거나, 또는 시아노, 니트로, 히드록실, 메르캅토, 아미노, 카르복실, 아미노카르보닐, 아미노티오카르보닐, 할로겐, C1-C6-알킬, C1-C6-할로알킬, C1-C6-알킬술포닐, C1-C6-알킬술폭실, C3-C6-시클로알킬, C1-C6-알콕시, C1-C6-할로알콕시, C1-C6-알킬옥시카르보닐, C1-C6-알킬티오, C1-C6-알킬아미노, 디-C1-C6-알킬아미노, C1-C6-알킬아미노카르보닐, 디-C1-C6-알킬아미노카르보닐, C1-C6-알킬아미노티오카르보닐, 디-C1-C6-알킬아미노티오카르보닐, C2-C6-알케닐, C2-C6-알케닐옥시, 벤질, 벤질옥시, 아릴, 아릴옥시, 아릴티오, 헤타릴, 헤타릴옥시, 헤타릴티오 또는 C(=NOR7)-An-R8의 기들중 1 내지 3개를 가질 수 있거나,C 1 -C 10 -alkyl, C 3 -C 6 -cycloalkyl, C 2 -C 10 -alkenyl, C 2 -C 10 -alkynyl, C 1 -C 10 -alkylcarbonyl, C 2 -C 10 -Alkenylcarbonyl, C 3 -C 10 -alkynylcarbonyl or C 1 -C 10 -alkylsulfonyl, these radicals may be partially or fully halogenated, or cyano, nitro, hydroxyl, mer Capto, amino, carboxyl, aminocarbonyl, aminothiocarbonyl, halogen, C 1 -C 6 -alkyl, C 1 -C 6 -haloalkyl, C 1 -C 6 -alkylsulfonyl, C 1 -C 6 -Alkylsulfoxy, C 1 -C 6 -alkoxy, C 1 -C 6 -haloalkoxy, C 1 -C 6 -alkoxycarbonyl, C 1 -C 6 -alkylthio, C 1 -C 6 -alkylamino, Di-C 1 -C 6 -alkylamino, C 1 -C 6 -alkylaminocarbonyl, di-C 1 -C 6 -alkylaminocarbonyl, C 1 -C 6 -alkylaminothiocarbonyl, di-C 1 -C 6 -alkylaminothiocarbonyl, C 2 -C 6 -alkenyl, C 2 -C 6 -alkenyloxy, C 3 -C 6 -cycloalkyl, C 3 -C 6 -cycloalkyloxy, Heterocyclyl, heterocyclyloxy, benzyl, benzyloxy, aryl, aryloxy, arylthio, hetaryl, hetaryloxy and hetarylthio may have 1 to 3 of the groups, wherein the cyclic groups themselves are partially Or completely halogenated, or cyano, nitro, hydroxyl, mercapto, amino, carboxyl, aminocarbonyl, aminothiocarbonyl, halogen, C 1 -C 6 -alkyl, C 1 -C 6- Haloalkyl, C 1 -C 6 -alkylsulfonyl, C 1 -C 6 -alkylsuloxyl, C 3 -C 6 -cycloalkyl, C 1 -C 6 -alkoxy, C 1 -C 6 -haloalkoxy, C 1- C 6 -alkyloxycarbonyl, C 1 -C 6 -alkylthio, C 1 -C 6 -alkylamino, di-C 1 -C 6 -alkylamino, C 1 -C 6 -alkylaminocarbonyl, Di-C 1 -C 6 -alkylaminocarbonyl, C 1 -C 6 -alkylaminothiocarbonyl, di-C 1 -C 6 -alkylaminothiocarbonyl, C 2 -C 6 -alkenyl, C 2 -C 6 -alkenyloxy, benzyl, benzyloxy, aryl, aryloxy, May have 1 to 3 of the groups arylthio, hetaryl, hetaryloxy, hetarylthio or C (= NOR 7 ) -A n -R 8 , or
아릴, 아릴카르보닐, 아릴술포닐, 헤타릴, 헤타릴카르보닐 또는 헤타릴술포닐이고, 이들 라디칼은 부분적으로 또는 완전히 할로겐화될 수 있거나, 또는 시아노, 니트로, 히드록실, 메르캅토, 아미노, 카르복실, 아미노카르보닐, 아미노티오카르보닐, 할로겐, C1-C6-알킬, C1-C6-할로알킬, C1-C6-알킬카르보닐, C1-C6-알킬술포닐, C1-C6-알킬술폭실, C3-C6-시클로알킬, C1-C6-알콕시, C1-C6-할로알콕시, C1-C6-알킬옥시카르보닐, C1-C6-알킬티오, C1-C6-알킬아미노, 디-C1-C6-알킬아미노, C1-C6-알킬아미노카르보닐, 디-C1-C6-알킬아미노카르보닐, C1-C6-알킬아미노티오카르보닐, 디-C1-C6-알킬아미노티오카르보닐, C2-C6-알케닐, C2-C6-알케닐옥시, 벤질, 벤질옥시, 아릴, 아릴옥시, 아릴티오, 헤타릴, 헤타릴옥시 또는 C(=NOR7)-An-R8의 기들중 1 내지 3개를 가질 수 있고,Aryl, arylcarbonyl, arylsulfonyl, hetaryl, hetarylcarbonyl or hetarylsulfonyl, these radicals may be partially or fully halogenated, or cyano, nitro, hydroxyl, mercapto, amino, carbon Carboxyl, aminocarbonyl, aminothiocarbonyl, halogen, C 1 -C 6 -alkyl, C 1 -C 6 -haloalkyl, C 1 -C 6 -alkylcarbonyl, C 1 -C 6 -alkylsulfonyl, C 1 -C 6 -alkylsuloxyl, C 3 -C 6 -cycloalkyl, C 1 -C 6 -alkoxy, C 1 -C 6 -haloalkoxy, C 1 -C 6 -alkyloxycarbonyl, C 1- C 6 -alkylthio, C 1 -C 6 -alkylamino, di-C 1 -C 6 -alkylamino, C 1 -C 6 -alkylaminocarbonyl, di-C 1 -C 6 -alkylaminocarbonyl, C 1 -C 6 -alkylaminothiocarbonyl, di-C 1 -C 6 -alkylaminothiocarbonyl, C 2 -C 6 -alkenyl, C 2 -C 6 -alkenyloxy, benzyl, benzyloxy, aryl, aryloxy, arylthio, taril H., H. taril oxy or a C (= NOR 7) -A n -R 8 May have from one to three of,
R5는 수소이거나,R 5 is hydrogen,
C1-C6-알킬, C2-C6-알케닐, C2-C6-알키닐이고, 이들 기의 탄화수소 라디칼은 부분적으로 또는 완전히 할로겐화될 수 있거나, 또는 시아노, 니트로, 히드록실, 메르캅토, 아미노, 카르복실, 아미노카르보닐, 아미노티오카르보닐, 할로겐, C1-C6-알킬아미노카르보닐, 디-C1-C6-알킬아미노카르보닐, C1-C6-알킬아미노티오카르보닐, 디-C1-C6-알킬아미노티오카르보닐, C1-C6-알킬술포닐, C1-C6-알킬술폭실, C1-C6-알콕시, C1-C6-할로알콕시, C1-C6-알콕시카르보닐, C1-C6-알킬티오, C1-C6-알킬아미노, 디-C1-C6-알킬아미노, C2-C6-알케닐옥시, C3-C6-시클로알킬, C3-C6-시클로알킬옥시, 헤테로시클릴, 헤테로시클릴옥시, 아릴, 아릴옥시, 아릴-C1-C4-알콕시, 아릴티오, 아릴-C1-C4-알킬티오, 헤타릴, 헤타릴옥시, 헤타릴-C1-C4-알콕시, 헤타릴티오, 헤타릴-C1-C4-알킬티오의 기들중 1 내지 3개를 가질 수 있으며, 이때 환상 기들 자체는 부분적으로 또는 완전히 할로겐화될 수 있고(있거나), 시아노, 니트로, 히드록실, 메르캅토, 아미노, 카르복실, 아미노카르보닐, 아미노티오카르보닐, C1-C6-알킬, C1-C6-할로알킬, C1-C6-알킬술포닐, C1-C6-알킬술폭실, C3-C6-시클로알킬, C1-C6-알콕시, C1-C6-할로알콕시, C1-C6-알콕시카르보닐, C1-C6-알킬티오, C1-C6-알킬아미노, 디-C1-C6-알킬아미노, C1-C6-알킬아미노카르보닐, 디-C1-C6-알킬아미노카르보닐, C1-C6-알킬아미노티오카르보닐, 디-C1-C6-알킬아미노티오카르보닐, C2-C6-알케닐, C2-C6-알케닐옥시, 벤질, 벤질옥시, 아릴, 아릴옥시, 아릴티오, 헤타릴, 헤타릴옥시, 헤타릴티오 및 C(=NOR7)-An-R8의 기들중 1 내지 3개를 가질 수 있거나,C 1 -C 6 -alkyl, C 2 -C 6 -alkenyl, C 2 -C 6 -alkynyl, and the hydrocarbon radicals of these groups may be partially or fully halogenated, or may be cyano, nitro, hydroxyl , Mercapto, amino, carboxyl, aminocarbonyl, aminothiocarbonyl, halogen, C 1 -C 6 -alkylaminocarbonyl, di-C 1 -C 6 -alkylaminocarbonyl, C 1 -C 6- alkylamino-thiocarbonyl, di -C 1 -C 6 - alkylamino-thiocarbonyl, C 1 -C 6 - alkylsulfonyl, C 1 -C 6 - alkyl sulfoxylates, C 1 -C 6 - alkoxy, C 1 -C 6 -haloalkoxy, C 1 -C 6 -alkoxycarbonyl, C 1 -C 6 -alkylthio, C 1 -C 6 -alkylamino, di-C 1 -C 6 -alkylamino, C 2 -C 6 -alkenyloxy, C 3 -C 6 -cycloalkyl, C 3 -C 6 -cycloalkyloxy, heterocyclyl, heterocyclyloxy, aryl, aryloxy, aryl-C 1 -C 4 -alkoxy, aryl thio, aryl -C 1 -C 4 - alkylthio, taril H., H. taril oxy, H. taril -C 1 -C 4 - alkoxy, H. Reel alkylthio, H. taril -C 1 -C 4 - may have 1 to 3 groups among the groups, and alkylthio, wherein the cyclic groups may be itself partially or completely halogenated (or), cyano, nitro, hydroxyl , Mercapto, amino, carboxyl, aminocarbonyl, aminothiocarbonyl, C 1 -C 6 -alkyl, C 1 -C 6 -haloalkyl, C 1 -C 6 -alkylsulfonyl, C 1 -C 6 -Alkylsulfoxy, C 3 -C 6 -cycloalkyl, C 1 -C 6 -alkoxy, C 1 -C 6 -haloalkoxy, C 1 -C 6 -alkoxycarbonyl, C 1 -C 6 -alkylthio, C 1 -C 6 -alkylamino, di-C 1 -C 6 -alkylamino, C 1 -C 6 -alkylaminocarbonyl, di-C 1 -C 6 -alkylaminocarbonyl, C 1 -C 6- Alkylaminothiocarbonyl, di-C 1 -C 6 -alkylaminothiocarbonyl, C 2 -C 6 -alkenyl, C 2 -C 6 -alkenyloxy, benzyl, benzyloxy, aryl, aryloxy, aryl Have 1 to 3 of the groups thio, hetaryl, hetaryloxy, hetarylthio and C (= NOR 7 ) -A n -R 8 Can be, or
C3-C6-시클로알킬, C3-C6-시클로알케닐, 헤테로시클릴, 아릴, 헤타릴이고, 이때 환상 라디칼들은 부분적으로 또는 완전히 할로겐화될 수 있거나, 또는 시아노, 니트로, 히드록실, 메르캅토, 아미노, 카르복실, 아미노카르보닐, 아미노티오카르보닐, 할로겐, C1-C6-알킬, C1-C6-할로알킬, C1-C6-알킬술포닐, C1-C6-알킬술폭실, C3-C6-시클로알킬, C1-C6-알콕시, C1-C6-할로알콕시, C1-C6-알콕시카르보닐, C1-C6-알킬티오, C1-C6-알킬아미노, 디-C1-C6-알킬아미노, C1-C6-알킬아미노카르보닐, 디-C1-C6-알킬아미노카르보닐, C1-C6-알킬아미노티오카르보닐, 디-C1-C6-알킬아미노티오카르보닐, C2-C6-알케닐, C2-C6-알케닐옥시, 벤질, 벤질옥시, 아릴, 아릴옥시, 헤타릴 및 헤타릴옥시의 기들중 1 내지 3개를 가질 수 있고,C 3 -C 6 -cycloalkyl, C 3 -C 6 -cycloalkenyl, heterocyclyl, aryl, hetaryl, wherein the cyclic radicals can be partially or fully halogenated, or cyano, nitro, hydroxyl , Mercapto, amino, carboxyl, aminocarbonyl, aminothiocarbonyl, halogen, C 1 -C 6 -alkyl, C 1 -C 6 -haloalkyl, C 1 -C 6 -alkylsulfonyl, C 1- C 6 -alkylsuloxyl, C 3 -C 6 -cycloalkyl, C 1 -C 6 -alkoxy, C 1 -C 6 -haloalkoxy, C 1 -C 6 -alkoxycarbonyl, C 1 -C 6 -alkyl Thio, C 1 -C 6 -alkylamino, di-C 1 -C 6 -alkylamino, C 1 -C 6 -alkylaminocarbonyl, di-C 1 -C 6 -alkylaminocarbonyl, C 1 -C 6 -alkylaminothiocarbonyl, di-C 1 -C 6 -alkylaminothiocarbonyl, C 2 -C 6 -alkenyl, C 2 -C 6 -alkenyloxy, benzyl, benzyloxy, aryl, aryloxy May have 1 to 3 of the groups hetaryl and hetaryloxy,
A는 산소, 황 또는 질소이고, 이때 질소는 수소 또는 C1-C6-알킬을 가지며,A is oxygen, sulfur or nitrogen, wherein nitrogen has hydrogen or C 1 -C 6 -alkyl,
n은 0 또는 1이고,n is 0 or 1,
R7은 수소 또는 C1-C6-알킬이고,R 7 is hydrogen or C 1 -C 6 -alkyl,
R8은 수소 또는 C1-C6-알킬이다.R 8 is hydrogen or C 1 -C 6 -alkyl.
본 발명의 목적은 살진균성 혼합물 성분들 각자의 살진균 활성을 초과하는 우수한 살진균 활성을 갖는, 특히 벼의 진균 질병에 대한 살진균성 혼합물을 제공하는 것이다.It is an object of the present invention to provide fungicidal mixtures, in particular against fungal diseases of rice, with good fungicidal activity exceeding the fungicidal activity of each of the fungicidal mixture components.
본 발명자들은 이 목적이 청구의 범위 제1항에 청구된 바와 같은 혼합물에 의해 달성됨을 발견하였다.The inventors have found that this object is achieved by a mixture as claimed in claim 1.
화학식 I의 화합물은 그 자체로서 공지되어 있으며, 문헌(WO 제97/15552호)에 기술되어 있다.Compounds of formula (I) are known per se and are described in WO 97/15552.
화학식 II 내지 화학식 VII의 살진균제 또한 공지되어 있으며, 문헌에 기술되어 있다. 또한, 이들은 하기 괄호안에 언급된 상표명으로 시중에서 입수된다:Fungicides of Formulas II-VII are also known and described in the literature. They are also commercially available under the trade names mentioned in parentheses below:
II: DE-A 제27 32 257호, 일반명: 펜시쿠론 (상표명: 몬세렌 (Monceren(R), 바이엘(Bayer)사)II: DE-A No. 27 32 257, common name: Pensicuron ( trade name: Monceren (R) , Bayer)
III: JP-A 제01/104,514호, 일반명: 플루톨라닐 (상표명: 몬컷 (Moncut(R)), 니혼 노야쿠(Nihon Noyaku)사)III: JP-A No. 01 / 104,514, common name: flutolanil (trade name: Moncut (R ), Nihon Noyaku)
IV: US 제3,937,840호, 일반명: 메프로닐 (상표명: 바시탁 (Basitac(R), 쿠미아이(Kumiai)사)IV: US 3,937,840, common name: Mepronil (trade name: Basitac (R) , Kumiai)
V: 일반명: 티플루자미드 (상표명: 그레아탐 (Greatam(R), 몬사토 (Monsato)사)V: common name: Tifluzamide ( trade name: Greatam (R) , Monsato)
VI: GB-A 제1,312,536호, US 제3,755,350호, 일반명: 이프로디온 (상표명: 로브랄 (Rovral(R)), 롱-쁠랑(Rhone-Poulenc)사)VI: GB-A No. 1,312,536, US No. 3,755,350, common name: Iprodion (trade name: Rovral (R ), Ron-Poulenc)
VII: 문헌 [AG Chem New Compound Review, Vol. 15 (1997), 50], 일반명: 푸라메트피르 (상표명: 림버 (Limber(R), 스미토모(Sumitomo)사)VII: AG Chem New Compound Review, Vol. 15 (1997), 50], common name: Purametpir ( trade name: Limber (R) , Sumitomo)
C=C 및 C=N 이중결합 때문에, 화학식 I의 화합물의 제조는 통상의 방식으로, 예를 들어 결정화 또는 크로마토그래피에 의해 개개의 화합물로 분리될 수 있는 E/Z 이성질체 혼합물을 생기게 할 수 있다.Because of the C═C and C═N double bonds, the preparation of compounds of formula (I) may give rise to E / Z isomer mixtures which may be separated into individual compounds in conventional manner, for example by crystallization or chromatography. .
그러나, 합성에 의해 이성질체 혼합물이 생기면, 일부 경우에 개개의 이성질체는 사용을 위해 제조하는 동안이나 사용할 때에 서로 전환될 수 있기 때문에(예를 들어 빛, 산 또는 염기의 작용하에) 분리는 일반적으로 반드시 필요하지는 않다. 유사한 전환은 또한, 예를 들어 식물의 치료 또는 방제할 유해 진균 또는 동물 해충에 사용한 후에 일어날 수도 있다.However, if synthesis results in an isomeric mixture, the separation is usually necessarily necessarily because in some cases the individual isomers can be converted to one another during or during use for use (eg under the action of light, acid or base). It is not necessary. Similar conversions may also occur after use, for example, in harmful fungi or animal pests to treat or control plants.
C=X 이중결합에 관해서는, 활성에 관하여 화학식 I의 화합물의 E 이성질체(-CO2R1- 기에 관해 -OCH3또는 -CH3기를 기준으로 한 배위)가 바람직하다.Regarding C = X double bonds, the E isomer of the compound of formula (I) with respect to activity (coordination based on —OCH 3 or —CH 3 groups relative to —CO 2 R 1 — groups) is preferred.
-C-(R3)=NOCH2- 이중결합에 관해서는, 활성에 관하여 화학식 I의 화합물의 시스 이성질체(-OCH2- 기에 관해 라디칼 R3을 기준으로 한 배위)가 바람직하다.With regard to -C- (R 3 ) = NOCH 2 -double bonds, the cis isomer of the compound of formula (I) with respect to activity (coordination based on the radical R 3 with respect to the -OCH 2 -group) is preferred.
처음에 주어진 화학식 I의 화합물의 정의에서, 일반적으로 다음의 기를 나타내는 집합적 용어를 사용하였다.In the definition of a compound of formula (I) given at first, a collective term is generally used which represents the following group.
할로겐: 플루오르, 염소, 브롬 및 요오드;Halogen: fluorine, chlorine, bromine and iodine;
알킬: 탄소수 1 내지 4, 6 또는 10의 직쇄 또는 분지쇄 알킬 기, 예를 들어 C1-C6-알킬(예: 메틸, 에틸, 프로필, 1-메틸에틸, 부틸, 1-메틸프로필, 2-메틸프로필, 1,1-디메틸에틸, 펜틸, 1-메틸부틸, 2-메틸부틸, 3-메틸부틸, 2,2-디메틸프로필, 1-에틸프로필, 헥실, 1,1-디메틸프로필, 1,2-디메틸프로필, 1-메틸펜텔, 2-메틸펜틸, 3-메틸펜틸, 4-메틸펜틸, 1,1-디메틸부틸, 1,2-디메틸부틸, 1,3-디메틸부틸, 2,2-디메틸부틸, 2,3-디메틸부틸, 3,3-디메틸부틸, 1-에틸부틸, 2-에틸부틸, 1,1,2-트리메틸프로필, 1,2,2-트리메틸프로필, 1-에틸-1-메틸프로필 및 1-에틸-2-메틸프로필);Alkyl: straight or branched chain alkyl groups of 1 to 4, 6 or 10 carbon atoms, for example C 1 -C 6 -alkyl (eg methyl, ethyl, propyl, 1-methylethyl, butyl, 1-methylpropyl, 2 -Methylpropyl, 1,1-dimethylethyl, pentyl, 1-methylbutyl, 2-methylbutyl, 3-methylbutyl, 2,2-dimethylpropyl, 1-ethylpropyl, hexyl, 1,1-dimethylpropyl, 1 , 2-dimethylpropyl, 1-methylpentel, 2-methylpentyl, 3-methylpentyl, 4-methylpentyl, 1,1-dimethylbutyl, 1,2-dimethylbutyl, 1,3-dimethylbutyl, 2,2 -Dimethylbutyl, 2,3-dimethylbutyl, 3,3-dimethylbutyl, 1-ethylbutyl, 2-ethylbutyl, 1,1,2-trimethylpropyl, 1,2,2-trimethylpropyl, 1-ethyl- 1-methylpropyl and 1-ethyl-2-methylpropyl);
할로알킬: 탄소수 1 내지 6의 직쇄 또는 분지쇄 알킬 기(이들 기의 수소 원자의 일부 또는 전부는 전술한 바와 같은 할로겐 원자로 대체될 수 있음), 예를 들어 C1-C2-할로알킬(예: 클로로메틸, 디클로로메틸, 트리클로로메틸, 플루오로메틸, 디플루오로메틸, 트리플루오로메틸, 클로로플루오로메틸, 디클로로플루오로메틸, 클로로디플루오로메틸, 1-플루오로에틸, 2-플루오로에틸, 2,2-디플루오로에틸, 2,2,2-트리플루오로에틸, 2-클로로-2-플루오로에틸, 2-클로로-2,2-디플루오로에틸, 2,2-디클로로-2-플루오로에틸, 2,2,2-트리클로로에틸 및 펜타플루오로에틸);Haloalkyl: straight or branched chain alkyl groups of 1 to 6 carbon atoms (some or all of the hydrogen atoms of these groups may be replaced by halogen atoms as described above), for example C 1 -C 2 -haloalkyl (eg : Chloromethyl, dichloromethyl, trichloromethyl, fluoromethyl, difluoromethyl, trifluoromethyl, chlorofluoromethyl, dichlorofluoromethyl, chlorodifluoromethyl, 1-fluoroethyl, 2-fluoro Roethyl, 2,2-difluoroethyl, 2,2,2-trifluoroethyl, 2-chloro-2-fluoroethyl, 2-chloro-2,2-difluoroethyl, 2,2- Dichloro-2-fluoroethyl, 2,2,2-trichloroethyl and pentafluoroethyl);
시클로알킬: 탄소 고리원수 3 내지 6의 단환상 알킬 기, 예를 들어 시클로프로필, 시클로부틸, 시클로펜틸 및 시클로헥실;Cycloalkyl: monocyclic alkyl groups having 3 to 6 carbon atoms, such as cyclopropyl, cyclobutyl, cyclopentyl and cyclohexyl;
알케닐: 탄소수 2 내지 6 또는 10이고 임의의 위치에 이중결합을 갖는 직쇄 또는 분지쇄 알케닐 기, 예를 들어 C2-C6-알케닐(예: 에테닐, 1-프로페닐, 2-프로페닐, 1-메틸에테닐, 1-부테닐, 2-부테닐, 3-부테닐, 1-메틸-1-프로페닐, 2-메틸-1-프로페닐, 1-메틸-2-프로페닐, 2-메틸-2-프로페닐, 1-펜테닐, 2-펜테닐, 3-펜테닐, 4-펜테닐, 1-메틸-1-부테닐, 2-메틸-1-부테닐, 3-메틸-1-부테닐, 1-메틸-2-부테닐, 2-메틸-2-부테닐, 3-메틸-2-부테닐, 1-메틸-3-부테닐, 2-메틸-3-부테닐, 3-메틸-3-부테닐, 1,1-디메틸-2-프로페닐, 1,2-디메틸-1-프로페닐, 1,2-디메틸-2-프로페닐, 1-에틸-1-프로페닐, 1-에틸-2-프로페닐, 1-헥세닐, 2-헥세닐, 3-헥세닐, 4-헥세닐, 5-헥세닐, 1-메틸-1-펜테닐, 2-메틸-1-펜테닐, 3-메틸-1-펜테닐, 4-메틸-1-펜테닐, 1-메틸-2-펜테닐, 2-메틸-2-펜테닐, 3-메틸-2-펜테닐, 4-메틸-2-펜테닐, 1-메틸-3-펜테닐, 2-메틸-3-펜테닐, 3-메틸-3-펜테닐, 4-메틸-3-펜테닐, 1-메틸-4-펜테닐, 2-메틸-4-펜테닐, 3-메틸-4-펜테닐, 4-메틸-4-펜테닐, 1,1-디메틸-2-부테닐, 1,1-디메틸-3-부테닐, 1,2-디메틸-1-부테닐, 1,2-디메틸-2-부테닐, 1,2-디메틸-3-부테닐, 1,3-디메틸-1-부테닐, 1,3-디메틸-2-부테닐, 1,3-디메틸-3-부테닐, 2,2-디메틸-3-부테닐, 2,3-디메틸-1-부테닐, 2,3-디메틸-2-부테닐, 2,3-디메틸-3-부테닐, 3,3-디메틸-1-부테닐, 3,3-디메틸-2-부테닐, 1-에틸-1-부테닐, 1-에틸-2-부테닐, 1-에틸-3-부테닐, 2-에틸-1-부테닐, 2-에틸-2-부테닐, 2-에틸-3-부테닐, 1,1,2-트리메틸-2-프로페닐, 1-에틸-1-메틸-2-프로페닐, 1-에틸-2-메틸-1-프로페닐 및 1-에틸-2-메틸-2-프로페닐);Alkenyl: straight or branched chain alkenyl groups having 2 to 6 or 10 carbon atoms and having a double bond in any position, for example C 2 -C 6 -alkenyl (eg ethenyl, 1-propenyl, 2- Propenyl, 1-methylethenyl, 1-butenyl, 2-butenyl, 3-butenyl, 1-methyl-1-propenyl, 2-methyl-1-propenyl, 1-methyl-2-propenyl , 2-methyl-2-propenyl, 1-pentenyl, 2-pentenyl, 3-pentenyl, 4-pentenyl, 1-methyl-1-butenyl, 2-methyl-1-butenyl, 3- Methyl-1-butenyl, 1-methyl-2-butenyl, 2-methyl-2-butenyl, 3-methyl-2-butenyl, 1-methyl-3-butenyl, 2-methyl-3-part Tenyl, 3-methyl-3-butenyl, 1,1-dimethyl-2-propenyl, 1,2-dimethyl-1-propenyl, 1,2-dimethyl-2-propenyl, 1-ethyl-1- Propenyl, 1-ethyl-2-propenyl, 1-hexenyl, 2-hexenyl, 3-hexenyl, 4-hexenyl, 5-hexenyl, 1-methyl-1-pentenyl, 2-methyl- 1-pentenyl, 3-methyl-1-pentenyl, 4-methyl-1-pentenyl, 1-methyl-2-pentenyl, 2-methyl-2-pentenyl, 3-methyl-2-pentenyl, 4-methyl-2-pentenyl, 1-methyl-3-pentenyl, 2-methyl-3-pentenyl, 3-methyl-3-pentenyl, 4-methyl-3-pentenyl, 1-methyl-4-pentenyl, 2-methyl-4 -Pentenyl, 3-methyl-4-pentenyl, 4-methyl-4-pentenyl, 1,1-dimethyl-2-butenyl, 1,1-dimethyl-3-butenyl, 1,2-dimethyl- 1-butenyl, 1,2-dimethyl-2-butenyl, 1,2-dimethyl-3-butenyl, 1,3-dimethyl-1-butenyl, 1,3-dimethyl-2-butenyl, 1 , 3-dimethyl-3-butenyl, 2,2-dimethyl-3-butenyl, 2,3-dimethyl-1-butenyl, 2,3-dimethyl-2-butenyl, 2,3-dimethyl-3 -Butenyl, 3,3-dimethyl-1-butenyl, 3,3-dimethyl-2-butenyl, 1-ethyl-1-butenyl, 1-ethyl-2-butenyl, 1-ethyl-3- Butenyl, 2-ethyl-1-butenyl, 2-ethyl-2-butenyl, 2-ethyl-3-butenyl, 1,1,2-trimethyl-2-propenyl, 1-ethyl-1-methyl -2-propenyl, 1-ethyl-2-methyl-1-propenyl and 1-ethyl-2-methyl-2-propenyl);
알키닐: 탄소수 2 내지 10이고 임의의 위치에 삼중결합을 갖는 직쇄 또는 분지쇄 알키닐 기, 예를 들어 C2-C6-알키닐(예: 에티닐, 2-프로피닐, 2-부티닐, 3-부티닐, 1-메틸-2-프로피닐, 2-펜티닐, 3-펜티닐, 4-펜티닐, 1-메틸-2-부티닐, 1-메틸-3-부티닐, 2-메틸-3-부티닐, 1,1-디메틸-2-프로피닐, 1-에틸-2-프로피닐, 2-헥시닐, 3-헥시닐, 4-헥시닐, 5-헥시닐, 1-메틸-2-펜티닐, 1-메틸-3-펜티닐, 1-메틸-4-펜티닐, 2-메틸-3-펜티닐, 2-메틸-4-펜티닐, 3-메틸-4-펜티닐, 4-메틸-2-펜티닐, 1,1-디메틸-2-부티닐, 1,1-디메틸-3-부티닐, 1,2-디메틸-3-부티닐, 2,2-디메틸-3-부티닐, 1-에틸-2-부티닐, 1-에틸-3-부티닐, 2-에틸-3-부티닐 및 1-에틸-1-메틸-2-프로피닐);Alkynyl: straight or branched chain alkynyl groups having 2 to 10 carbon atoms and having triple bonds at any position, for example C 2 -C 6 -alkynyl (eg ethynyl, 2-propynyl, 2-butynyl , 3-butynyl, 1-methyl-2-propynyl, 2-pentynyl, 3-pentynyl, 4-pentynyl, 1-methyl-2-butynyl, 1-methyl-3-butynyl, 2- Methyl-3-butynyl, 1,1-dimethyl-2-propynyl, 1-ethyl-2-propynyl, 2-hexynyl, 3-hexynyl, 4-hexynyl, 5-hexynyl, 1-methyl -2-pentynyl, 1-methyl-3-pentynyl, 1-methyl-4-pentynyl, 2-methyl-3-pentynyl, 2-methyl-4-pentynyl, 3-methyl-4-pentynyl , 4-methyl-2-pentynyl, 1,1-dimethyl-2-butynyl, 1,1-dimethyl-3-butynyl, 1,2-dimethyl-3-butynyl, 2,2-dimethyl-3 -Butynyl, 1-ethyl-2-butynyl, 1-ethyl-3-butynyl, 2-ethyl-3-butynyl and 1-ethyl-1-methyl-2-propynyl);
헤테로시클릴 또는 헤테로시클릴옥시, 헤테로시클릴티오 및 헤테로시클릴아미노: 산소, 질소 및 황으로 이루어진 군에서 선택된 1 내지 3개의 헤테로원자를 함유하고, 골격에 직접 결합되거나 또는 산소 원자에 의해(헤테로시클릴옥시) 또는 황 원자에 의해(헤테로시클릴티오) 또는 질소 원자에 의해(헤테로시클릴아미노) 결합된 3원 내지 6원의 포화 또는 부분 불포화된 단환상 또는 다환상 헤테로환(예: 2-테트라히드로푸라닐, 옥시라닐, 3-테트라히드로푸라닐, 2-테트라히드로티에닐, 3-테트라히드로티에닐, 2-피롤리디닐, 3-피롤리디닐, 3-이속사졸리디닐, 4-이속사졸리디닐, 5-이속사졸리디닐, 3-이소티아졸리디닐, 4-이소티아졸리디닐, 5-이소티아졸리디닐, 3-피라졸리디닐, 4-피라졸리디닐, 5-피라졸리디닐, 2-옥사졸리디닐, 4-옥사졸리디닐, 5-옥사졸리디닐, 2-티아졸리디닐, 4-티아졸리디닐, 5-티아졸리디닐, 2-이미다졸리디닐, 4-이미다졸리디닐, 1,2,4-옥사졸리딘-3-일, 1,2,4-옥사디아졸리딘-5-일, 1,2,4-티아디아졸리딘-3-일, 1,2,4-티아디아졸리딘-5-일, 1,2,4-트리아졸리딘-3-일, 1,3,4-옥사디아졸리딘-2-일, 1,3,4-티아디아졸리딘-2-일, 1,3,4-트리아졸리딘-2-일, 2,3-디히드로푸르-2-일, 2,3-디히드로푸르-3-일, 2,3-디히드로푸르-4-일, 2,3-디히드로푸르-5-일, 2,5-디히드로푸르-2-일, 2,5-디히드로푸르-3-일, 2,3-디히드로티엔-2-일, 2,3-디히드로티엔-3-일, 2,3-디히드로티엔-4-일, 2,3-디히드로티엔-5-일, 2,5-디히드로티엔-2-일, 2,5-디히드로티엔-3-일, 2,3-디히드로피롤-2-일, 2,3-디히드로피롤-3-일, 2,3-디히드로피롤-4-일, 2,3-디히드로피롤-5-일, 2,5-디히드로피롤-2-일, 2,5-디히드로피롤-3-일, 2,3-디히드로이속사졸-3-일, 2,3-디히드로이속사졸-4-일, 2,3-디히드로이속사졸-5-일, 4,5-디히드로이속사졸-3-일, 4,5-디히드로이속사졸-4-일, 4,5-디히드로이속사졸-5-일, 2,5-디히드로이소티아졸-3-일, 2,5-디히드로이소티아졸-4-일, 2,5-디히드로이소티아졸-5-일, 2,3-디히드로이소피라졸-3-일, 2,3-디히드로이소피라졸-4-일, 2,3-디히드로이소피라졸-5-일, 4,5-디히드로이소피라졸-3-일, 4,5-디히드로이소피라졸-4-일, 4,5-디히드로이소피라졸-5-일, 2,5-디히드로이소피라졸-3-일, 2,5-디히드로이소피라졸-4-일, 2,5-디히드로이소피라졸-5-일, 2,3-디히드로옥사졸-3-일, 2,3-디히드로옥사졸-4-일, 2,3-디히드로옥사졸-5-일, 4,5-디히드로옥사졸-3-일, 4,5-디히드로옥사졸-4-일, 4,5-디히드로옥사졸-5-일, 2,5-디히드로옥사졸-3-일, 2,5-디히드로옥사졸-4-일, 2,5-디히드로옥사졸-5-일, 2,3-디히드로티아졸-2-일, 2,3-디히드로티아졸-4-일, 2,3-디히드로티아졸-5-일, 4,5-디히드로티아졸-2-일, 4,5-디히드로티아졸-4-일, 4,5-디히드로티아졸-5-일, 2,5-디히드로티아졸-2-일, 2,5-디히드로티아졸-4-일, 2,5-디히드로티아졸-5-일, 2,3-디히드로이미다졸-2-일, 2,3-디히드로이미다졸-4-일, 2,3-디히드로이미다졸-5-일, 4,5-디히드로이미다졸-2-일, 4,5-디히드로이미다졸-4-일, 4,5-디히드로이미다졸-5-일, 2,5-디히드로이미다졸-2-일, 2,5-디히드로이미다졸-4-일, 2,5-디히드로이미다졸-5-일, 2-모르폴리닐, 3-모르폴리닐, 2-피페리디닐, 3-피페리디닐, 4-피페리디닐, 3-테트라히드로피리다지닐, 4-테트라히드로피리다지닐, 2-테트라히드로피리미디닐, 4-테트라히드로피리미디닐, 5-테트라히드로피리미디닐, 2-테트라히드로피라지닐, 1,3,5-테트라히드로트리아진-2-일, 1,2,4-테트라히드로트리아진-3-일, 1,3-디히드로옥사진-2-일, 1,3-디티안-2-일, 2-테트라히드로피라닐, 1,3-디옥솔란-2-일, 3,4,5,6-테트라히드로피리딘-2-일, 4H-1,3-티아진-2-일, 4H-3,1-벤조티아진-2-일, 1,1-디옥소-2,3,4,5-테트라히드로티엔-2-일, 2H-1,4-벤조티아진-3-일, 2H-1,4-벤족사진-3-일, 1,3-디히드로옥사진-2-일, 1,3-디티안-2-일);Heterocyclyl or heterocyclyloxy, heterocyclylthio and heterocyclylamino: contain one to three heteroatoms selected from the group consisting of oxygen, nitrogen and sulfur and are directly attached to the backbone or by an oxygen atom ( Heterocyclyloxy) or a 3- to 6-membered saturated or partially unsaturated monocyclic or polycyclic heterocycle (e.g., bonded by a hetero atom (heterocyclylthio) or by a nitrogen atom (heterocyclylamino) 2-tetrahydrofuranyl, oxiranyl, 3-tetrahydrofuranyl, 2-tetrahydrothienyl, 3-tetrahydrothienyl, 2-pyrrolidinyl, 3-pyrrolidinyl, 3-isoxazolidinyl, 4-isoxazolidinyl, 5-isoxazolidinyl, 3-isothiazolidinyl, 4-isothiazolidinyl, 5-isothiazolidinyl, 3-pyrazolidinyl, 4-pyrazolidinyl, 5-pyra Zolidinyl, 2-oxazolidinyl, 4-oxazolidinyl, 5-oxazolidinyl , 2-thiazolidinyl, 4-thiazolidinyl, 5-thiazolidinyl, 2-imidazolidinyl, 4-imidazolidinyl, 1,2,4-oxazolidin-3-yl, 1,2 , 4-oxadiazolidin-5-yl, 1,2,4-thiadiazolidin-3-yl, 1,2,4-thiadiazolidin-5-yl, 1,2,4-triazoli Din-3-yl, 1,3,4-oxadiazolidin-2-yl, 1,3,4-thiadiazolidin-2-yl, 1,3,4-triazolidin-2-yl, 2,3-dihydrofur-2-yl, 2,3-dihydrofur-3-yl, 2,3-dihydrofur-4-yl, 2,3-dihydrofur-5-yl, 2, 5-dihydrofur-2-yl, 2,5-dihydrofur-3-yl, 2,3-dihydrothien-2-yl, 2,3-dihydrothien-3-yl, 2,3- Dihydrothien-4-yl, 2,3-dihydrothien-5-yl, 2,5-dihydrothien-2-yl, 2,5-dihydrothien-3-yl, 2,3-dihydro Pyrrole-2-yl, 2,3-dihydropyrrole-3-yl, 2,3-dihydropyrrole-4-yl, 2,3-dihydropyrrole-5-yl, 2,5-dihydropyrrole- 2-yl, 2,5-dihydropyrrole-3-yl, 2,3-dihydroisoxazol-3-yl, 2,3-dihydroisoxazol-4-yl, 2, 3-dihydroisoxazol-5-yl, 4,5-dihydroisoxazol-3-yl, 4,5-dihydroisoxazol-4-yl, 4,5-dihydroisoxazol-5-yl, 2,5-dihydroisothiazol-3-yl, 2,5-dihydroisothiazol-4-yl, 2,5-dihydroisothiazol-5-yl, 2,3-dihydroisopyra Zol-3-yl, 2,3-dihydroisopyrazol-4-yl, 2,3-dihydroisopyrazol-5-yl, 4,5-dihydroisopyrazol-3-yl, 4, 5-dihydroisopyrazol-4-yl, 4,5-dihydroisopyrazol-5-yl, 2,5-dihydroisopyrazol-3-yl, 2,5-dihydroisopyrazol- 4-yl, 2,5-dihydroisopyrazol-5-yl, 2,3-dihydrooxazol-3-yl, 2,3-dihydrooxazol-4-yl, 2,3-dihydro Oxazol-5-yl, 4,5-dihydrooxazol-3-yl, 4,5-dihydrooxazol-4-yl, 4,5-dihydrooxazol-5-yl, 2,5- Dihydrooxazol-3-yl, 2,5-dihydrooxazol-4-yl, 2,5-dihydrooxazol-5-yl, 2,3-dihydrothiazol-2-yl, 2, 3-dihydrothiazol-4-yl, 2,3-dihydrothiazole-5 -Yl, 4,5-dihydrothiazol-2-yl, 4,5-dihydrothiazol-4-yl, 4,5-dihydrothiazol-5-yl, 2,5-dihydrothiazole -2-yl, 2,5-dihydrothiazol-4-yl, 2,5-dihydrothiazol-5-yl, 2,3-dihydroimidazol-2-yl, 2,3-dihydro Imidazol-4-yl, 2,3-dihydroimidazol-5-yl, 4,5-dihydroimidazol-2-yl, 4,5-dihydroimidazol-4-yl, 4,5- Dihydroimidazol-5-yl, 2,5-dihydroimidazol-2-yl, 2,5-dihydroimidazol-4-yl, 2,5-dihydroimidazol-5-yl, 2- Morpholinyl, 3-morpholinyl, 2-piperidinyl, 3-piperidinyl, 4-piperidinyl, 3-tetrahydropyridazinyl, 4-tetrahydropyridazinyl, 2-tetrahydropyrimidy Nyl, 4-tetrahydropyrimidinyl, 5-tetrahydropyrimidinyl, 2-tetrahydropyrazinyl, 1,3,5-tetrahydrotriazin-2-yl, 1,2,4-tetrahydrotriazine -3-yl, 1,3-dihydrooxazin-2-yl, 1,3-ditian-2-yl, 2-tetrahi Ropyranyl, 1,3-dioxolan-2-yl, 3,4,5,6-tetrahydropyridin-2-yl, 4H-1,3-thiazin-2-yl, 4H-3,1- Benzothiazin-2-yl, 1,1-dioxo-2,3,4,5-tetrahydrothien-2-yl, 2H-1,4-benzothiazin-3-yl, 2H-1,4 Benzoxazine-3-yl, 1,3-dihydrooxazin-2-yl, 1,3-dithiane-2-yl);
아릴 또는 아릴옥시, 아릴티오, 아릴카르보닐 및 아릴술포닐: 골격에 직접 결합되거나 또는 산소 원자(-O-)에 의해(아릴옥시) 또는 황 원자(-S-)에 의해(아릴티오) 또는 카르보닐 기(-CO-)에 의해(아릴카르보닐) 또는 술포닐 기(-SO2-)에 의해(아릴술포닐) 결합되는 방향족 단환상 또는 다환상 수소 라디칼(예: 페닐, 나프틸 및 페난트레닐 또는 페닐옥시, 나프틸옥시 및 페난트레닐옥시 및 상응하는 카르보닐 및 술포닐 라디칼);Aryl or aryloxy, arylthio, arylcarbonyl and arylsulfonyl: bonded directly to the backbone or by an oxygen atom (-O-) (aryloxy) or by a sulfur atom (-S-) (arylthio) or Aromatic monocyclic or polycyclic hydrogen radicals (e.g., phenyl, naphthyl and the like) bonded by a carbonyl group (-CO-) (arylcarbonyl) or by a sulfonyl group (-SO 2- ) (arylsulfonyl) Phenanthrenyl or phenyloxy, naphthyloxy and phenanthrenyloxy and corresponding carbonyl and sulfonyl radicals);
헤타릴 또는 헤타릴옥시, 헤타릴티오, 헤타릴카르보닐 및 헤타릴술포닐: 탄소 고리원 외에 추가로 1 내지 4개의 질소 원자 또는 1 내지 3개의 질소 원자 및 1개의 산소 또는 1개의 황 원자 또는 1개의 산소 또는 1개의 황 원자를 함유할 수 있고, 골격에 직접 결합되거나 또는 산소 원자(-O-)에 의해(헤타릴옥시) 또는 황 원자(-S-)에 의해(헤타릴티오), 카르보닐 기(-CO-)에 의해(헤타릴카르보닐) 또는 술포닐 기(-SO2-)에 의해(헤타릴술포닐) 결합된 방향족 단환상 또는 다환상 라디칼, 예를 들면Hetaryl or hetaryloxy, hetarylthio, hetarylcarbonyl and hetarylsulfonyl: in addition to carbon ring members, additionally 1 to 4 nitrogen atoms or 1 to 3 nitrogen atoms and 1 oxygen or 1 sulfur atom or 1 May contain one oxygen or one sulfur atom, directly attached to the skeleton, or by an oxygen atom (-O-) (hetaryloxy) or by a sulfur atom (-S-) (hetarylthio) Aromatic monocyclic or polycyclic radicals bound by a carbonyl group (-CO-) (hetarylcarbonyl) or by a sulfonyl group (-SO 2- ) (hetarylsulfonyl), for example
- 1 내지 3개의 질소 원자를 함유하는 5원의 헤테로아릴: 탄소 원자 외에 고리원으로서 1 내지 3개의 질소 원자를 함유할 수 있는 5원의 헤테로아릴 기(예: 2-피롤릴, 3-피롤릴, 3-피라졸릴, 4-피라졸릴, 5-피라졸릴, 2-이미다졸릴, 4-이미다졸릴, 1,2,4-트리아졸-3-일 및 1,3,4-트리아졸-2-일);5 membered heteroaryl containing 1 to 3 nitrogen atoms: 5 membered heteroaryl groups which may contain 1 to 3 nitrogen atoms as ring members in addition to carbon atoms (eg 2-pyrrolyl, 3-py) Rollyl, 3-pyrazolyl, 4-pyrazolyl, 5-pyrazolyl, 2-imidazolyl, 4-imidazolyl, 1,2,4-triazol-3-yl and 1,3,4-triazole -2 days);
- 1 내지 4개의 질소 원자 또는 1 내지 3개의 질소 원자 및 1개의 황 또는 산소 원자 또는 1개의 산소 또는 1개의 황 원자를 함유하는 5원의 헤테로아릴: 탄소 원자 외에 고리원으로서 1 내지 4개의 질소 원자 또는 1 내지 3개의 질소 원자 및 1개의 황 또는 산소 원자 또는 1개의 산소 또는 황 원자를 함유할 수 있는 5원의 헤테로아릴 기(예: 2-푸릴, 3-푸릴, 2-티에닐, 3-티에닐, 2-피롤릴, 3-피롤릴, 3-이속사졸릴, 4-이속사졸릴, 5-이속사졸릴, 3-이소티아졸릴, 4-이소티아졸릴, 5-이소티아졸릴, 3-피라졸릴, 4-피라졸릴, 5-피라졸릴, 2-옥사졸릴, 4-옥사졸릴, 5-옥사졸릴, 2-티아졸릴, 4-티아졸릴, 5-티아졸릴, 2-이미다졸릴, 4-이미다졸릴, 1,2,4-옥사디아졸-3-일, 1,2,4-옥사디아졸-5-일, 1,2,4-티아디아졸-3-일, 1,2,4-티아디아졸-5-일, 1,2,4-트리아졸-3-일, 1,3,4-옥사디아졸-2-일, 1,3,4-티아디아졸-2-일, 1,3,4-트리아졸-2-일);5 membered heteroaryl containing 1 to 4 nitrogen atoms or 1 to 3 nitrogen atoms and 1 sulfur or oxygen atom or 1 oxygen or 1 sulfur atom: 1 to 4 nitrogens as ring members in addition to carbon atoms 5 membered heteroaryl groups which may contain atoms or 1 to 3 nitrogen atoms and 1 sulfur or oxygen atom or 1 oxygen or sulfur atom (e.g. 2-furyl, 3-furyl, 2-thienyl, 3 -Thienyl, 2-pyrrolyl, 3-pyrrolyl, 3-isoxazolyl, 4-isoxazolyl, 5-isoxazolyl, 3-isothiazolyl, 4-isothiazolyl, 5-isothiazolyl, 3-pyrazolyl, 4-pyrazolyl, 5-pyrazolyl, 2-oxazolyl, 4-oxazolyl, 5-oxazolyl, 2-thiazolyl, 4-thiazolyl, 5-thiazolyl, 2-imidazolyl , 4-imidazolyl, 1,2,4-oxadiazol-3-yl, 1,2,4-oxadiazol-5-yl, 1,2,4-thiadiazol-3-yl, 1 , 2,4-thiadiazol-5-yl, 1,2,4-triazol-3-yl, 1,3,4-oxadiazol-2-yl, 1,3,4-thia Diazol-2-yl, 1,3,4-triazol-2-yl);
- 1 내지 3개의 질소 원자 또는 1개의 질소 원자 및(또는) 1개의 산소 또는 황 원자를 함유하는 벤조-융합된 5원의 헤테로아릴: 탄소 원자 외에 고리원으로서 1 내지 4개의 질소 원자 또는 1 내지 3개의 질소 원자 및 1개의 황 또는 산소 원자 또는 1개의 산소 또는 1개의 황 원자를 함유할 수 있고, 2개의 인접한 탄소 고리원 또는 1개의 질소 원자와 1개의 인접한 탄소 고리원이 부타-1,3-디엔-1,4-디일 기에 의해 가교될 수 있는 5원의 헤테로아릴 기;Benzo-fused 5 membered heteroaryl containing 1 to 3 nitrogen atoms or 1 nitrogen atom and / or 1 oxygen or sulfur atom: from 1 to 4 nitrogen atoms or from 1 to 4 as ring members in addition to carbon atoms It may contain three nitrogen atoms and one sulfur or oxygen atom or one oxygen or one sulfur atom, and two adjacent carbon ring members or one nitrogen atom and one adjacent carbon ring member are buta-1,3 5-membered heteroaryl groups which may be crosslinked by diene-1,4-diyl groups;
- 질소에 의해 결합되고 1 내지 4개의 질소 원자를 함유하는 5원의 헤테로아릴, 또는 질소에 의해 결합되고 1 내지 3개의 질소 원자를 함유하는 벤조-융합된 5원의 헤테로아릴: 탄소 원자 외에 고리원으로서 각각 1 내지 4개의 질소 원자 및 1 내지 3개의 질소 원자를 함유할 수 있고, 2개의 인접한 탄소 고리원 또는 1개의 질소와 1개의 인접한 탄소 고리원이 부타-1,3-디엔-1,4-디일 기에 의해 가교될 수 있는 5원의 헤테로아릴 기(이들 고리는 질소 고리원중 1개에 의해 골격에 결합됨);5-membered heteroaryl bonded by nitrogen and containing 1 to 4 nitrogen atoms, or benzo-fused 5-membered heteroaryl bonded by nitrogen and containing 1 to 3 nitrogen atoms: ring in addition to carbon atoms As a circle, it may contain 1 to 4 nitrogen atoms and 1 to 3 nitrogen atoms, respectively, and two adjacent carbon ring members or one nitrogen and one adjacent carbon ring member may be buta-1,3-diene-1, 5-membered heteroaryl groups which can be crosslinked by 4-diyl groups (these rings are attached to the backbone by one of the nitrogen ring members);
- 각각 1 내지 3개의 질소 원자 및 1 내지 4개의 질소 원자를 함유하는 6원의 헤테로아릴: 탄소 원자 외에 고리원으로서 각각 1 내지 3개의 질소 원자 및 1 내지 4개의 질소 원자를 함유할 수 있는 6원의 헤테로아릴 기(예: 2-피리디닐, 3-피리디닐, 4-피리디닐, 3-피리다지닐, 4-피리다지닐, 2-피리미디닐, 4-피리미디닐, 5-피리미디닐, 2-피라지닐, 1,3,5-트리아진-2-일, 1,2,4-트리아진-3-일 및 1,2,4,5-테트라진-3-일);6-membered heteroaryl containing 1 to 3 nitrogen atoms and 1 to 4 nitrogen atoms each: 6 which may contain 1 to 3 nitrogen atoms and 1 to 4 nitrogen atoms respectively as ring members in addition to carbon atoms Circle heteroaryl groups such as 2-pyridinyl, 3-pyridinyl, 4-pyridinyl, 3-pyridazinyl, 4-pyridazinyl, 2-pyrimidinyl, 4-pyrimidinyl, 5-pyri Midinyl, 2-pyrazinyl, 1,3,5-triazin-2-yl, 1,2,4-triazin-3-yl and 1,2,4,5-tetrazin-3-yl);
- 1 내지 4개의 질소 원자를 함유하는 벤조-융합된 6원의 헤테로아릴: 2개의 인접한 탄소 고리원이 부타-1,3-디엔-1,4-디일 기에 의해 가교될 수 있는 6원의 헤테로아릴 기(예: 퀴놀린, 이소퀴놀린, 퀴나졸린 및 퀴녹살린),Benzo-fused 6 membered heteroaryl containing 1 to 4 nitrogen atoms: 6 membered hetero where two adjacent carbon ring members can be crosslinked by buta-1,3-diene-1,4-diyl groups Aryl groups (e.g. quinoline, isoquinoline, quinazoline and quinoxaline),
및 상응하는 옥시, 티오, 카르보닐 또는 술포닐 기;And corresponding oxy, thio, carbonyl or sulfonyl groups;
헤타릴아미노: 탄소 고리원 외에 추가로 1 내지 4개의 질소 원자 또는 1 내지 3개의 질소 원자 및 1개의 산소 또는 1개의 황 원자를 함유할 수 있고, 질소 원자에 의해 골격에 결합되는 방향족 단환상 또는 다환상 라디칼.Hetarylamino: Aromatic monocyclic or containing 1 to 4 nitrogen atoms or 1 to 3 nitrogen atoms and 1 oxygen or 1 sulfur atom in addition to the carbon ring member and bonded to the skeleton by a nitrogen atom or Polycyclic radicals.
"부분적으로 또는 완전히 할로겐화된"이란 설명은 그렇게 특징화된 기의 수소 원자의 일부 또는 전부가 전술한 바와 같은 동일하거나 상이한 할로겐 원자로 대체될 수 있음을 표현하려는 것이다.The description “partially or fully halogenated” is intended to indicate that some or all of the hydrogen atoms of the groups so characterized may be replaced with the same or different halogen atoms as described above.
그의 생물학적 활성에 관해서는, m이 0인 화학식 I의 화합물이 바람직하다.As for its biological activity, compounds of formula (I) in which m is zero are preferred.
마찬가지로, R1이 메틸인 화학식 I의 화합물이 바람직하다.Likewise preferred are compounds of formula I, wherein R 1 is methyl.
그 외에, R3이 수소, 시아노, 시클로프로필, 메틸, 에틸, 1-메틸에틸 또는 CF3인 화학식 I의 화합물이 바람직하다.In addition, preference is given to compounds I in which R 3 is hydrogen, cyano, cyclopropyl, methyl, ethyl, 1-methylethyl or CF 3 .
게다가, R3이 메틸인 화학식 I의 화합물이 바람직하다.Furthermore, preference is given to compounds of the formula (I) in which R 3 is methyl.
그 외에, R3이 시아노인 화학식 I의 화합물이 바람직하다.In addition, preference is given to compounds I in which R 3 is cyano.
게다가, R3이 시클로프로필인 화학식 I의 화합물이 바람직하다.Furthermore, preference is given to compounds of the formula (I) in which R 3 is cyclopropyl.
또한, R3이 CF3인 화학식 I의 화합물이 바람직하다.Also preferred are compounds of formula I, wherein R 3 is CF 3 .
또한, R5가 수소, 시클로프로필, 메틸, 에틸, 이소프로필, 치환되지 않거나 치환된 아릴 또는 헤타릴인 화학식 I의 화합물이 바람직하다.Also preferred are compounds of formula I, wherein R 5 is hydrogen, cyclopropyl, methyl, ethyl, isopropyl, unsubstituted or substituted aryl or hetaryl.
게다가, R5가 메틸인 화학식 I의 화합물이 바람직하다.Furthermore, preference is given to compounds of the formula (I) in which R 5 is methyl.
또한, R5가 에틸인 화학식 I의 화합물이 바람직하다.Also preferred are compounds of formula I, wherein R 5 is ethyl.
게다가, R5가 이소프로필인 화학식 I의 화합물이 바람직하다.Furthermore, preference is given to compounds of the formula (I) in which R 5 is isopropyl.
게다가, R5가 시클로프로필인 화학식 I의 화합물이 바람직하다.Furthermore, preference is given to compounds of the formula (I) in which R 5 is cyclopropyl.
게다가, R5가 CF3인 화학식 I의 화합물이 바람직하다.Furthermore, compounds of formula I wherein R 5 is CF 3 are preferred.
또한, R5가 치환되지 않거나 치환된 아릴 또는 헤타릴인 화학식 I의 화합물이 바람직하다.Also preferred are compounds of formula I, wherein R 5 is unsubstituted or substituted aryl or hetaryl.
또한, R5가 치환되지 않거나 치환된 피리딜, 피리미딜, 피라지닐, 피리다니질 또는 트리아지닐인 화학식 I의 화합물이 바람직하다.Preference is furthermore given to compounds of the formula (I) in which R 5 is unsubstituted or substituted pyridyl, pyrimidyl, pyrazinyl, pyridanizyl or triazinyl.
또한, R5가 치환되지 않거나 치환된 푸릴, 티에닐 또는 피롤릴인 화학식 I의 화합물이 바람직하다.Also preferred are compounds of formula I, wherein R 5 is unsubstituted or substituted furyl, thienyl or pyrrolyl.
또한, R5가 치환되지 않거나 치환된 옥사졸릴, 티아졸릴, 이속사졸릴, 이소티아졸릴, 피라졸릴 또는 이미다졸릴인 화학식 I의 화합물이 바람직하다.Also preferred are compounds of formula I, wherein R 5 is unsubstituted or substituted oxazolyl, thiazolyl, isoxazolyl, isothiazolyl, pyrazolyl or imidazolyl.
또한, R5가 치환되지 않거나 치환된 옥사디아졸릴, 티아디아졸릴 또는 트리아졸릴인 화학식 I의 화합물이 바람직하다.Preference is furthermore given to compounds of the formula (I) in which R 5 is unsubstituted or substituted oxadiazolyl, thiadiazolyl or triazolyl.
게다가, R5가 치환되지 않거나 또는 니트로, 시아노, 히드록실, 아미노, 아미노카르보닐, 아미노티오카르보닐, 할로겐, C1-C4-알킬, C1-C4-할로알킬, C1-C4-알콕시, C1-C4-할로알콕시, C1-C4-알킬아미노, 디-C1-C4-알킬아미노, C1-C4-알킬술포닐, C1-C4-알콕시카르보닐, C1-C4-알킬아미노카르보닐 또는 디-C1-C4-알킬아미노카르보닐의 기들중 1 또는 2개를 갖는 화학식 I의 화합물이 바람직하다.Furthermore, R 5 is unsubstituted or nitro, cyano, hydroxyl, amino, aminocarbonyl, aminothiocarbonyl, halogen, C 1 -C 4 -alkyl, C 1 -C 4 -haloalkyl, C 1- C 4 -alkoxy, C 1 -C 4 -haloalkoxy, C 1 -C 4 -alkylamino, di-C 1 -C 4 -alkylamino, C 1 -C 4 -alkylsulfonyl, C 1 -C 4- Preference is given to compounds of the formula (I) having one or two of the groups of alkoxycarbonyl, C 1 -C 4 -alkylaminocarbonyl or di-C 1 -C 4 -alkylaminocarbonyl.
게다가, R4가 수소, C1-C6-알킬, C2-C6-알케닐, C2-C6-알키닐, 알릴, 아릴알킬, 헤타릴알킬, 아릴옥시알킬, 헤타릴옥시알킬, 아릴 또는 헤타릴인 화학식 I의 화합물이 바람직하다.Furthermore, R 4 is hydrogen, C 1 -C 6 -alkyl, C 2 -C 6 -alkenyl, C 2 -C 6 -alkynyl, allyl, arylalkyl, hetarylalkyl, aryloxyalkyl, hetaryloxyalkyl Preference is given to compounds of the formula (I) which are aryl or hetaryl.
또한, R4가 C1-C6-알킬인 화학식 I의 화합물이 바람직하다.Also preferred are compounds of formula I, wherein R 4 is C 1 -C 6 -alkyl.
추가의 바람직한 화학식 I의 화합물은 WO 제97/15,552호에 개시되어 있다.Further preferred compounds of formula I are disclosed in WO 97 / 15,552.
본 발명에 따른 혼합물에 함유된 화학식 I의 화합물은 광범위한 식물병원성 진균, 특히 아스코미세테스(Ascomycetes), 듀테로미세테스(Deuteromycetes), 피코미세테스(Phycomycetes) 및 바시디오미세테스(Basidiomycetes) 부류의 진균에 대해 탁월한 활성을 갖는다.The compounds of formula (I) contained in the mixtures according to the invention are of the broad range of phytopathogenic fungi, in particular Ascomycetes, Deuteromycetes, Phycomycetes and Basidiomycetes. Has excellent activity against fungi.
이들은 면, 야채 종(예를 들어 오이, 콩, 토마토, 감자 및 호리병박), 보리, 잔디, 귀리, 바나나, 커피, 옥수수, 과일 종, 벼, 호밀, 대두, 포도덩굴, 밀, 장식용 식물, 사탕수수와 같은 각종 농작물 및 각종 종자에서 다수의 진균을 방제하는데 특히 중요하다.These include cotton, vegetable species (e.g. cucumbers, beans, tomatoes, potatoes and calabash), barley, grass, oats, bananas, coffee, corn, fruit species, rice, rye, soybeans, grapevines, wheat, decorative plants, candy It is particularly important for controlling a large number of fungi in various crops such as sorghum and various seeds.
이들은 다음의 식물병원성 진균을 방제하기에 특히 적합하다: 곡물의 에리시페 그라미니스(Erysiphe graminis)(분말상 흰가루병 병균), 호리병박의 에리시페 치코라세아룸(Erysiphe cichoracearum) 및 스파에로쎄카 풀리기네아(Sphaerotheca fuliginea), 사과의 포도스파에라 류코트리카(Podosphaera leucotricha), 포도덩굴의 운치눌라 네카토르(Uncinula necator), 곡물의 푸치니아(Puccinia) 종, 면, 벼 및 잔디의 리족토니아(Rhizoctonia) 종, 곡물 및 사탕수수의 우스틸라고(Ustilago) 종, 사과의 벤투리아 이나에쿠알리스(Venturia inaequalis)(반점병), 곡물 및 벼의 헬민토스포리움(Helminthosporium) 종, 밀의 셉토리아 노도룸(Septoria nodorum), 딸기, 야채, 장식용 식물 및 포도덩굴의 보트리티스 치네라(Botrytis cinera)(회색 곰팡이), 그라운드너트의 체르코스포라 아라키디콜라(Cercospora arachidicola), 밀 및 보리의 슈도체르코스포렐라 헤르포트리코이데스(Pseudocercosporella herpotrichoides), 벼 및 잔디의 피리쿨라리아 오리자에(Pyricularia oryzae), 감자 및 토마토의 피토프토라 인페스탄스(Phytophthora infestans), 포도덩굴의 플라스모파라 비티콜라(Plasmopara viticola), 홉 및 오이의 슈도페로노스포라(Pseudoperonospora) 종, 야채 및 과일의 알테르나리아(Alternaria) 종, 바나나의 미코스파에렐라(Mycosphaerella) 종 및 푸사리움(Fusarium) 및 베르티칠리움(Verticillium) 종.They are particularly suitable for controlling the following phytopathogenic fungi: Erysiphe graminis (powdery powdery mildew) on grains, Erysiphe cichoracearum and Sageroseca on calabash. Sphaerotheca fuliginea, Podosphaera leucotricha of apples, Uncinula necator of grapevines, Puccinia species of grains, lyctonia of cotton, rice and grass Rhizoctonia species, Ustilago species in cereals and sugar cane, Venturia inaequalis (spot disease) in apples, Helminthosporium species in cereals and rice, Septoria nordo in wheat Botrytis cinera (gray mold) in the room (Septoria nodorum), berries, vegetables, decorative plants and grapevines, Cecospora arachidicola of groundnuts, wheat and barley Pseudocercosporella herpotrichoides, Pyricularia oryzae of rice and grass, Phytophthora infestans of potatoes and tomatoes, Plasmo of grapevines Plasmopara viticola, Pseudoperonospora species of hops and cucumbers, Alternaria species of vegetables and fruits, Mycosphaerella species of bananas and Fusarium and ber Verticillium species.
화학식 II 내지 화학식 VII의 화합물은 살진균제로서 시중에서 입수할 수 있다.Compounds of formulas (II) to (VII) are commercially available as fungicides.
혼합물을 제조할 때, 순수한 활성 성분 화학식 I 및 화학식 II 내지 화학식 VII의 화합물을 사용하는 것이 바람직하고, 이들과 함께 유해 진균 또는 다른 해충(예: 곤충, 절지동물 또는 선충류)에 대한 추가의 활성 성분, 또는 그밖에 제초성 또는 성장-조절성 활성 성분 또는 비료를 혼합할 수 있다.When preparing the mixture, it is preferred to use the pure active ingredients of the compounds of the formulas (I) and (II) to (VII) together with further active ingredients against harmful fungi or other pests (eg insects, arthropods or nematodes). Or other herbicidal or growth-regulating active ingredients or fertilizers.
화학식 I의 화합물과 화학식 II 내지 화학식 VII의 화합물중 1종 이상의 화합물의 혼합물은 동시에, 즉 연합하여 또는 별개로 적용될 수 있고, 광범위한 식물병원성 진균, 특히 아스코미세테스, 바시디오미세테스, 피코미세테스 및 듀테로미세테스 부류의 식물병원성 진균에 대해 뛰어난 작용을 나타낸다. 이들중 일부는 전신적으로 작용하며, 따라서 잎-작용성 및 토양-작용성 살진균제로서 사용하기에 또한 적합하다.Mixtures of compounds of formula (I) with at least one of the compounds of formulas (II) to (VII) may be applied simultaneously, ie in association or separately, and can be applied to a wide range of phytopathogenic fungi, in particular ascomycetes, bacidiomycetes, picomicetes And phytopathogenic fungi of the Deuteromycetes family. Some of these act systemically and are therefore also suitable for use as leaf- and soil-acting fungicides.
이들은 면, 야채 종(예를 들어, 오이, 콩, 토마토, 감자 및 호리병박), 보리, 잔디, 귀리, 바나나, 커피, 옥수수, 과일 종, 벼, 호밀, 대두, 포도덩굴, 밀, 장식용 식물, 사탕수수와 같은 각종 농작물 및 각종 종자에서 다수의 진균을 방제하는데 특히 중요하다.These include cotton, vegetable species (e.g. cucumbers, beans, tomatoes, potatoes and calabash), barley, grass, oats, bananas, coffee, corn, fruit species, rice, rye, soybeans, grapevines, wheat, decorative plants, It is particularly important for controlling a large number of fungi in various crops such as sugar cane and various seeds.
이들은 다음의 식물병원성 진균을 방제하기에 특히 적합하다: 곡물의 에리시페 그라미니스(흰가루병 병균), 호리병박의 에리시페 치코라세아룸 및 스파에로쎄카 풀리기네아, 사과의 포도스파에라 류코트리카, 포도덩굴의 운치눌라 네카토르, 곡물의 푸치니아 종, 면, 벼 및 잔디의 리족토니아 종, 곡물 및 사탕수수의 우스틸라고 종, 사과의 벤투리아 이나에쿠알리스(반점병), 곡물 및 벼의 헬민토스포리움 종, 밀의 셉토리아 노도룸, 딸기, 야채, 장식용 식물 및 포도덩굴의 보트리티스 치네라(회색 곰팡이), 그라운드너트의 체르코스포라 아라키디콜라, 밀 및 보리의 슈도체르코스포렐라 헤르포트리코이데스, 벼 및 잔디의 피리쿨라리아 오리자에, 감자 및 토마토의 피토프토라 인페스탄스, 포도덩굴의 플라스모파라 비티콜라, 홉 및 오이의 슈도페로노스포라 종, 야채 및 과일의 알테르나리아 종, 바나나의 미코스파에렐라 종 및 푸사리움 및 베르티칠리움 종.They are particularly suitable for controlling the following phytopathogenic fungi: erythrophe graminis (powdery mildew) of grains, erythrope chicolacearum of calabash, and spaeroceca pulliginea, grapes of spara of apples. Cortica, Cunchinula necka of grapevines, Puccinia species of grains, Lithuanian species of cotton, rice and grass, Ustilago species of cereals and sugar cane, Venturia inaqualis of apples, grains And Helmintosporium species of rice, Septoria nodorum of wheat, strawberries, vegetables, botanicals Chineris (grey mold) of grapevines and ground vines, chercospora arachidola of groundnuts, shu of wheat and barley Dochercosporella herporticoides, Pycuraria orizae of rice and grass, phytophthora infestans of potatoes and tomatoes, Plasmopara viticola of grapevines, Pseudoferono of cucumbers and cucumbers Fora kinds of vegetables and fruits altereuna Leah species, in Mico Relais Spa in bananas and Fusarium species and Bell tichil Leeum species.
본 발명에 따른 혼합물은 피리쿨라리아 오리자에를 방제하는데 특히 바람직하게 사용할 수 있다.The mixtures according to the invention can be used particularly preferably for controlling pyricuria orissa.
화학식 I의 화합물 및 화학식 II 내지 화학식 VII의 화합물중 1종 이상을 함께 또는 별개로 동시에 적용하거나 또는 연속적으로 적용할 수 있으며, 별개 적용의 경우에 순서는 일반적으로 방제 결과에 어떠한 영향도 주지 않는다.One or more of the compounds of formula (I) and compounds of formulas (II) to (VII) may be applied together or separately simultaneously or sequentially, in the case of separate applications the order generally does not have any effect on the control results.
원하는 효과의 성질에 따라, 본 발명에 따른 혼합물의 적용률은, 특히 농작물에서, 0.01 내지 8㎏/ha, 바람직하게는 0.1 내지 5㎏/ha, 특히 0.5 내지 3.0㎏/ha이다.Depending on the nature of the desired effect, the application rate of the mixture according to the invention is, in particular in crops, from 0.01 to 8 kg / ha, preferably from 0.1 to 5 kg / ha, in particular from 0.5 to 3.0 kg / ha.
화학식 I의 화합물의 경우, 적용률은 0.01 내지 2.5㎏/ha, 바람직하게는 0.05 내지 2.5㎏/ha, 특히 0.1 내지 1.0㎏/ha이다.For compounds of formula (I), the application rate is from 0.01 to 2.5 kg / ha, preferably from 0.05 to 2.5 kg / ha, in particular from 0.1 to 1.0 kg / ha.
상응하게, 화학식 II 내지 화학식 VII의 화합물의 경우, 적용률은 0.001 내지 5㎏/ha, 바람직하게는 0.005 내지 2㎏/ha, 특히 0.01 내지 1.0㎏/ha이다.Correspondingly, for compounds of the formulas (II) to (VII), the application rate is from 0.001 to 5 kg / ha, preferably from 0.005 to 2 kg / ha, in particular from 0.01 to 1.0 kg / ha.
종자 처리의 경우, 혼합물의 적용률은 일반적으로 0.001 내지 250g/㎏(종자), 바람직하게는 0.01 내지 100g/㎏, 특히 0.01 내지 50g/㎏이다.In the case of seed treatment, the application rate of the mixture is generally from 0.001 to 250 g / kg (seed), preferably from 0.01 to 100 g / kg, in particular from 0.01 to 50 g / kg.
식물병원성 유해 진균을 방제하려는 경우, 화학식 I의 화합물 및 화학식 II 내지 화학식 VII의 화합물중 1종 이상의 별개 또는 연합 적용은 식물을 심기 전 또는 후에, 또는 식물이 발아하기 전 또는 후에 종자, 식물 또는 토양에 분무하거나 흩뿌려 행한다.In the case of controlling phytopathogenic harmful fungi, one or more separate or combined applications of the compounds of formula (I) and compounds of formulas (II) to (VII) may be used to seed, plant or soil before or after planting or before or after plant germination. Spray or spray on.
본 발명에 따른 살진균성 상승작용성 혼합물은, 예를 들어 즉시 분무할 수 있는 용액, 분말 및 현탁액 형태로 또는 진하게 농축된 수성, 오일상 또는 다른 현탁액, 분산액, 유화액, 오일 분산액, 페이스트, 가루, 살포용 물질 또는 과립 현태로 배합되고, 분무, 분사, 흩뿌리기, 살포 또는 살수에 의해 적용될 수 있다. 사용 형태는 소기의 목적에 따라 좌우되는데, 어느 경우에서나 본 발명에 따른 혼합물의 분포를 가능한 미세하고 균일하게 하여야 한다.The fungicidal synergistic mixtures according to the invention are, for example, in the form of solutions, powders and suspensions which can be sprayed immediately or in concentrated, aqueous or oily or other suspensions, dispersions, emulsions, oil dispersions, pastes, powders, It can be formulated as a spraying material or granules and applied by spraying, spraying, spraying, spraying or spraying. The form of use depends on the intended purpose, in which case the distribution of the mixtures according to the invention should be as fine and uniform as possible.
배합물은 공지의 방식으로, 예를 들어 활성 성분을 용매 및(또는) 담체로 팽창시킴으로써, 바람직한 경우 유화제 및 분산제를 사용하여 제조한다. 사용된 희석제가 물인 경우, 보조 용매로서 다른 유기 용매를 사용하는 것도 가능하다. 적합한 보조제는 본질적으로 방향족(예를 들어, 크실렌), 염화 방향족(예를 들어, 클로로벤젠), 파라핀(예를 들어, 미네랄 유분), 알콜(예를 들어, 메탄올, 부탄올), 케톤(예를 들어, 시클로헥산온), 아민(예를 들어, 에탄올아민, 디메틸포름아미드) 및 물과 같은 용매; 천연 분쇄 미네랄(예를 들어, 카올린, 점토, 활석, 백악) 및 분쇄된 합성 미네랄(예를 들어, 미분된 실리카, 실리케이트)과 같은 담체; 비이온성 및 음이온성 유화제(예를 들어, 폴리옥시에틸렌 지방 알콜 에테르, 알킬술포네이트 및 아릴술포네이트)와 같은 유화제; 및 리그노술파이트 폐수 및 메틸셀룰로즈와 같은 분산제이다.The formulation is prepared in a known manner, for example by swelling the active ingredient into a solvent and / or carrier, using emulsifiers and dispersants, if desired. If the diluent used is water, it is also possible to use other organic solvents as auxiliary solvents. Suitable auxiliaries are essentially aromatic (eg xylenes), chlorinated aromatics (eg chlorobenzene), paraffins (eg mineral fractions), alcohols (eg methanol, butanol), ketones (eg Solvents such as, for example, cyclohexanone), amines (eg ethanolamine, dimethylformamide) and water; Carriers such as natural ground minerals (eg kaolin, clay, talc, chalk) and ground synthetic minerals (eg finely divided silica, silicates); Emulsifiers such as nonionic and anionic emulsifiers (eg, polyoxyethylene fatty alcohol ethers, alkylsulfonates and arylsulfonates); And dispersants such as lignosulphite wastewater and methylcellulose.
적합한 계면활성제는 방향족 설폰산, 예컨대 리그노-, 페놀-, 나프탈렌- 및 디부틸나프탈렌-술폰산의 알칼리 금속 염, 알칼리 토금속 염 및 암모늄 염, 및 지방산, 알킬- 및 알킬아릴-술포네이트, 알킬, 라우릴 에테르 및 지방 알콜 술페이트의 알칼리 금속 염, 알칼리 토금속 염 및 암모늄 염, 및 술페이트화 헥사-, 헵타- 및 옥타-데칸올의 염, 또는 지방 알콜 글리콜 에테르의 염, 술포네이트화 나프탈렌 및 그의 유도체와 포름알데히드의 축합물, 나프탈렌 또는 나프탈렌술폰산과 페놀 및 포름알데히드의 축합물, 폴리옥시에틸렌 옥틸페놀 에테르, 에톡실화 이소옥틸-, 옥틸- 또는 노닐-페놀, 알킬페놀 폴리글리콜 에테르, 트리부틸페닐 폴리글리콜 에테르, 알킬아릴 폴리에테르 알콜, 이소트리데실 알콜, 지방 알콜 에틸렌 옥사이드 축합물, 에톡실화 아주까리유, 폴리옥시에틸렌 알킬 에테르 또는 폴리옥시프로필렌, 라우릴 알콜 폴리글리콜 에테르 아세테이트, 소르비톨 에스테르, 리그노술파이트 폐수 또는 메틸셀룰로즈이다.Suitable surfactants include alkali metal salts, alkaline earth metal salts and ammonium salts of aromatic sulfonic acids such as ligno-, phenol-, naphthalene- and dibutylnaphthalene-sulfonic acid, and fatty acids, alkyl- and alkylaryl-sulfonates, alkyl, Alkali metal salts, alkaline earth metal salts and ammonium salts of lauryl ether and fatty alcohol sulfates, and salts of sulfated hexa-, hepta- and octa-decanol, or salts of fatty alcohol glycol ethers, sulfonated naphthalenes and Condensates of derivatives thereof with formaldehyde, condensates of naphthalene or naphthalenesulfonic acids with phenols and formaldehydes, polyoxyethylene octylphenol ethers, ethoxylated isooctyl-, octyl- or nonyl-phenols, alkylphenol polyglycol ethers, tributyl Phenyl Polyglycol Ether, Alkylaryl Polyether Alcohol, Isotridecyl Alcohol, Fatty Alcohol Ethylene Oxide Condensate, Ethoxylated Castor Lye, polyoxyethylene alkyl ether or polyoxypropylene, lauryl alcohol polyglycol ether acetate, sorbitol ester, lignosulphite wastewater or methylcellulose.
분말, 살포용 물질 및 가루는 화학식 I의 화합물 및 화학식 II 내지 화학식 VII의 화합물중 1종 이상 또는 화학식 I의 화합물 및 화학식 II 내지 화학식 VII의 화합물 1종 이상과 고체 담체의 혼합물을 혼합하거나 함께 분쇄함으로써 제조할 수 있다.The powders, spargers and powders are mixed or pulverized with a mixture of at least one of the compounds of formula (I) and compounds of formulas (II) to (VII) or at least one compound of formula (I) and at least one compound of formulas (II) to (VII) It can manufacture by doing.
과립(예컨대, 피복된 과립, 함침된 과립 또는 균질 과립)은 일반적으로 활성 성분 또는 활성 성분들을 고체 담체에 결합시킴으로써 제조한다.Granules (eg coated granules, impregnated granules or homogeneous granules) are generally prepared by binding the active ingredient or active ingredients to a solid carrier.
충전제 또는 고체 담체는, 예를 들어 미네랄 토(예: 실리카 겔, 규산, 실리카 겔, 실리케이트, 활석, 카올린, 석회석, 석회, 백악, 교회 점토, 황토, 점토, 백운석, 규조토, 황산 칼슘, 황산 마그네슘, 산화 마그네슘, 분쇄된 합성 물질), 비료(예: 황산 암모늄, 인산 암모늄, 질산 암모늄, 우레아), 식물 기원의 생성물(예: 곡물 가루, 나무 껍질 가루, 나무 가루 및 견과 껍질 가루), 셀룰로즈 분말 또는 기타 고체 담체이다.Fillers or solid carriers are for example mineral earth (e.g. silica gel, silicic acid, silica gel, silicates, talc, kaolin, limestone, lime, chalk, church clay, ocher, clay, dolomite, diatomaceous earth, calcium sulfate, magnesium sulfate) , Magnesium oxide, ground synthetic materials), fertilizers (e.g. ammonium sulfate, ammonium phosphate, ammonium nitrate, urea), products of plant origin (e.g. grain flour, bark powder, wood flour and nut shell powder), cellulose powder Or other solid carriers.
배합물은 일반적으로 화학식 I의 화합물중 1종 및 화학식 II 내지 화학식 VII의 화합물중 1종 이상 또는 화학식 I의 화합물과 화학식 II 내지 화학식 VII의 화합물중 1종 이상의 혼합물 0.1 내지 95중량%, 바람직하게는 0.5 내지 90중량%를 포함한다. 활성 성분은 순도 90% 내지 100%, 바람직하게는 95% 내지 100%(NMR 또는 HPLC 스펙트럼에 따라)로 사용된다.The blend is generally 0.1 to 95% by weight, preferably a mixture of at least one of the compounds of formula (I) and at least one of the compounds of formulas (II) to (VII) or at least one of 0.5 to 90% by weight. The active ingredient is used at a purity of 90% to 100%, preferably 95% to 100% (according to NMR or HPLC spectra).
상응하는 배합물은 유해 진균, 이들의 번식지 또는 식물, 종자, 토양, 지면, 유해 진균을 제거해야 하는 물질 또는 공간을 살진균 유효량의 상기 혼합물 또는 별개 적용의 경우에는 살진균 유효량의 화학식 I의 화합물 및 화학식 II 내지 화학식 VII의 화합물중 1종 이상으로 처리함으로써 적용한다.Corresponding combinations include fungicidally effective amounts of the compounds of formula I in the case of a fungicidally effective amount of said mixture or separate application of harmful fungi, their breeding grounds or plants, seeds, soil, ground, substances or spaces to which harmful fungi are to be removed, and It is applied by treating with one or more of the compounds of the formulas (II) to (VII).
적용은 유해 진균에 의한 감염 전 또는 후에 행할 수 있다.Application can be done before or after infection with harmful fungi.
활성 성분을 포함하는 그러한 제제의 예는 다음과 같다.Examples of such formulations comprising the active ingredient are as follows.
I. 활성 성분 90중량부 및 N-메틸피롤리돈 10중량부의 용액; 이 용액은 미소점적약 형태로 사용하기에 적합하다.I. A solution of 90 parts by weight of active ingredient and 10 parts by weight of N-methylpyrrolidone; This solution is suitable for use in the form of microdroplets.
II. 활성 성분 20중량부, 크실렌 80중량부, 산화 에틸렌 8 내지 10몰과 올레산 N-모노에탄올아미드 1몰의 부가물 10중량부, 도데실벤젠술포네이트의 칼슘 염 5중량부, 산화 에틸렌 40몰과 아주까리유 1몰의 부가물 5중량부의 혼합물; 이 용액을 물에 미세하게 분산시켜 분산액을 얻는다.II. 20 parts by weight of the active ingredient, 80 parts by weight of xylene, 10 parts by weight of an adduct of 8 to 10 moles of ethylene oxide and 1 mole of oleic acid N-monoethanolamide, 5 parts by weight of calcium salt of dodecylbenzenesulfonate, and 40 moles of ethylene oxide A mixture of 5 parts by weight of an adduct of 1 mol of castor oil; The solution is finely dispersed in water to obtain a dispersion.
III. 활성 성분 20중량부, 시클로헥산온 40중량부, 이소부탄올 30중량부, 산화 에틸렌 40몰과 아주까리유 1몰의 부가물 20중량부의 수성 분산액.III. 20 parts by weight of the active ingredient, 40 parts by weight of cyclohexanone, 30 parts by weight of isobutanol, 20 parts by weight of an adduct of 40 moles of ethylene oxide and 1 mole of castor oil.
IV. 활성 성분 20중량부, 시클로헥산올 25중량부, 비점 210 내지 280℃의 미네랄 유분 65중량부 및 산화 에틸렌 40몰과 아주까리유 1몰의 부가물 10중량부의 수성 분산액.IV. An aqueous dispersion of 20 parts by weight of active ingredient, 25 parts by weight of cyclohexanol, 65 parts by weight of mineral oil having a boiling point of 210 to 280 ° C., and 10 parts by weight of an adduct of 40 parts of ethylene oxide and 1 part of castor oil.
V. 활성 성분 80중량부, 디이소부틸나프탈렌-1-술폰산의 나트륨 염 3중량부, 술파이트 폐수로부터의 리그노술폰산의 나트륨 염 10중량부 및 미분 실리카 겔 7중량부를 해머 밀(hammer mill)에서 분쇄한 혼합물; 이 혼합물을 물에 미세하게 분포시켜 분무 혼합물을 얻는다.V. 80 parts by weight of active ingredient, 3 parts by weight of sodium salt of diisobutylnaphthalene-1-sulfonic acid, 10 parts by weight of sodium salt of lignosulfonic acid from sulfite wastewater and 7 parts by weight of finely divided silica gel hammer mill A mixture ground in the; This mixture is finely distributed in water to obtain a spray mixture.
VI. 활성 성분 3중량부 및 미분된 카올린 97중량부의 균질 혼합물; 이 가루는 활성 성분 3중량%를 포함한다.VI. A homogeneous mixture of 3 parts by weight of the active ingredient and 97 parts by weight of finely divided kaolin; This powder contains 3% by weight of active ingredient.
VII. 활성 성분 30중량부, 미분 실리카 겔 92중량부 및 이 실리카 겔의 표면에 분무된 파라핀 오일 8중량부의 균질 혼합물; 이 배합은 활성 성분에 우수한 부착력을 부여한다.VII. A homogeneous mixture of 30 parts by weight of the active ingredient, 92 parts by weight of finely divided silica gel and 8 parts by weight of paraffin oil sprayed onto the surface of the silica gel; This formulation imparts good adhesion to the active ingredient.
VIII. 활성 성분 40중량부, 페놀술폰산/우레아/포름알데히드 축합물의 나트륨 염 10중량부, 실리카 겔 2중량부 및 물 48중량부의 안정한 수성 분산액; 이 분산액은 추가로 희석될 수 있다.VIII. 40 parts by weight of the active ingredient, 10 parts by weight of the sodium salt of the phenolsulfonic acid / urea / formaldehyde condensate, 2 parts by weight of silica gel and 48 parts by weight of water, a stable aqueous dispersion; This dispersion may be diluted further.
IX. 활성 성분 20중량부, 도데실벤젠술폰산의 칼슘 염 2중량부, 지방 알콜 폴리글리콜 에테르 8중량부, 페놀술폰산/우레아/포름알데히드 축합물의 나트륨 염 20중량부 및 파라핀 미네랄 오일 88중량부의 안정한 오일상 분산액.IX. 20 parts by weight of active ingredient, 2 parts by weight of calcium salt of dodecylbenzenesulfonic acid, 8 parts by weight of fatty alcohol polyglycol ether, 20 parts by weight of sodium salt of phenolsulfonic acid / urea / formaldehyde condensate and 88 parts by weight of paraffin mineral oil Dispersion.
본 발명에 따른 혼합물의 상승작용성 활성은 하기 실험에 의해 증명될 수 있다.The synergistic activity of the mixtures according to the invention can be demonstrated by the following experiment.
활성 성분들은 별개로 또는 함께 시클로헥산온 63중량% 및 유화제 27중량%의 혼합물내 10% 유화액으로서 배합되고, 원하는 농도로 물로 상응하게 희석된다.The active ingredients are separately or together formulated as 10% emulsions in a mixture of 63% cyclohexanone and 27% by weight emulsifier and correspondingly diluted with water to the desired concentration.
감염된 잎 면적을 백분율로 결정함으로써 평가를 수행한다. 이 백분율을 효능으로 환산한다. 효능(W)은 아보트(Abbot)의 식을 사용하여 다음과 같이 계산한다.The evaluation is performed by determining the infected leaf area as a percentage. This percentage is converted into efficacy. Efficacy (W) is calculated as follows using Abbot's formula.
상기 식에서,Where
α는 처리된 식물의 진균 감염률(%)에 해당하고,α corresponds to the percentage of fungal infections of treated plants,
β는 처리되지 않은(콘트롤) 식물의 진균 감염률(%)에 해당한다.β corresponds to the percentage of fungal infection of untreated (control) plants.
효능이 0이라는 것은 처리된 식물의 감염 수준이 처리되지 않은 콘트롤 식물의 감염 수준에 해당함을 뜻하며, 효능이 100이라는 것은 처리된 식물이 감염되지 않았음을 뜻한다.An efficacy of zero means that the infection level of the treated plant corresponds to that of an untreated control plant, while an efficacy of 100 means that the treated plant is not infected.
활성 성분들의 혼합물의 예상 효능은 하기 콜비(Colby)의 식(콜비(R. S. Colby)의 문헌[Weeds 15, 20-22 (1967)]을 사용하여 결정하였고, 관측된 효능과 비교하였다.The expected potency of the mixture of active ingredients was determined using the following Colby's formula (Weeds 15, 20-22 (1967) by R. S. Colby) and compared with the observed potency.
상기 식에서,Where
E는 농도 a 및 b의 활성 성분 A 및 B의 혼합물을 사용하였을 때, 처리되지 않은 콘트롤의 백분율(%)로 표현된 예상 효능이고,E is the expected potency expressed as a percentage of untreated control when using a mixture of active ingredients A and B at concentrations a and b,
x는 농도 a의 활성 성분 A를 사용하였을 때, 처리되지 않은 콘트롤의 백분율(%)로 표현된 효능이고,x is the efficacy expressed as percent of untreated control when using active ingredient A at concentration a,
y는 농도 b의 활성 성분 B를 사용하였을 때, 처리되지 않은 콘트롤의 백분율(%)로 표현된 효능이다.y is the efficacy expressed as percentage of untreated control when using active ingredient B at concentration b.
사용예 1-피리쿨라리아 오리자에에 대한 활성(예방적)Use Example 1-Activity against Pycurularia Oryza (prophylactic)
화분에 심은 벼 묘종 품종 "타이-농(Tai-Nong) 67"의 잎에, 활성 성분 10%, 시클로헥산온 63% 및 유화제 27%를 포함하는 모액으로부터 제조한 활성 성분의 수성 제제를 분무하여 흘러내리게 하였다. 다음날, 식물에 피리쿨라리아 오리자에의 수성 포자 현탁액을 접종하였다. 이어서 시험 식물을 22 내지 24℃ 및 상대 대기 습도 95 내지 99%의 기후 조절된 챔버에 6일동안 두었다. 그 다음, 잎의 감염 진행 정도를 육안으로 결정하였다.To the leaves of the potted rice seedling variety "Tai-Nong 67", sprayed with an aqueous formulation of the active ingredient prepared from the mother liquor comprising 10% active ingredient, 63% cyclohexanone and 27% emulsifier Let it flow down. The next day, the plants were inoculated with an aqueous spore suspension of Pycuraria Orissa. The test plants were then placed in a climate controlled chamber at 22-24 ° C. and 95-99% relative atmospheric humidity for 6 days. Then, the extent of infection of the leaves was visually determined.
병에 걸린 잎 면적의 백분율에 대해 육안으로 결정한 값을 처리되지 않은 콘트롤의 백분율로서 효능으로 환산하였다. 효능 0은 처리되지 않은 콘트롤에서와 같은 질병 수준을 뜻하고, 효능 100은 질병 0%를 뜻한다. 활성 성분 조합물의 예상 효능은 콜비의 식(콜비의 문헌["Calculating synergistic and antagonistic responses of herbicide combinations", Weeds, 15, pp.20-22, 1967])을 사용하여 결정하였고, 관측된 효능과 비교하였다.The visually determined value for the percentage of diseased leaf area was converted into efficacy as a percentage of untreated control. Efficacy 0 means the same disease level as in untreated control, and efficacy 100 means 0% disease. The expected efficacy of the active ingredient combination was determined using Colby's formula ("Calculating synergistic and antagonistic responses of herbicide combinations", Weeds, 15, pp.20-22, 1967) and compared with the observed efficacy. It was.
하기 화학식 I'의 화합물을 성분 a)로서 사용하였다:The following compound of formula I 'was used as component a):
실험의 결과를 하기 표 1 및 표 2에 나타낸다.The results of the experiments are shown in Tables 1 and 2 below.
시험 결과, 모든 혼합 비율에서 콜비의 식을 사용하여 사전에 계산된 효능보다 관측된 효능이 더 높았다.The test results showed that the observed efficacy was higher than previously calculated efficacy using Colby's equation at all mixing ratios.
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