KR100370872B1 - Substituted aromatic thiocarboxylic acid amides and their use as herbicides - Google Patents

Substituted aromatic thiocarboxylic acid amides and their use as herbicides Download PDF

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KR100370872B1
KR100370872B1 KR1019960706166A KR19960706166A KR100370872B1 KR 100370872 B1 KR100370872 B1 KR 100370872B1 KR 1019960706166 A KR1019960706166 A KR 1019960706166A KR 19960706166 A KR19960706166 A KR 19960706166A KR 100370872 B1 KR100370872 B1 KR 100370872B1
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링커 칼-하인즈
핀다이젠 쿠르트
안드레 롤란트
빌헬름 드레베스 마르크
렌더 안드레아스
샬너 오토
하스 빌헬름
잔텔 한스-요하힘
돌링거 마르쿠스
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바이엘 악티엔게젤샤프트
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Abstract

본 발명은 하기 일반식(I)의 신규한 치환된 방향족 티오카복스아미드 및 제초제로서의 그의 용도에 관한 것이다.The present invention relates to novel substituted aromatic thiocarboxamides of the general formula (I) and their use as herbicides.

상기 식에서,Where

R1, R2및 R3는 수소 또는 여러 치환체이며,R 1 , R 2 and R 3 are hydrogen or several substituents,

Z 는 임의로 치환된 모노사이클릭 또는 비사이클릭의 포화 또는 불포화 헤테로사이클릴, 헤테로사이클릴아미노 또는 혜테로사이클릴이미노이다.Z is optionally substituted monocyclic or bicyclic saturated or unsaturated heterocyclyl, heterocyclylamino or heterocyclylimino.

Description

치환된 방향족 티오카복실산 아미드 및 제초제로서의 그의 용도Substituted aromatic thiocarboxylic acid amides and their use as herbicides

본 발명은 신규한 치환된 방향족 티오카복스아미드, 그의 제조 방법 및 제초제로서의 그의 용도에 관한 것이다.The present invention relates to novel substituted aromatic thiocarboxamides, processes for their preparation and their use as herbicides.

특정의 방향족 카보티오아미드, 예를 들어 2,6-디클로로벤조티오아미드("클로르티아미드")가 제초 성질을 가지고 있음은 이미 알려져 있다(참조 : GB-B 987253). 그러나, 이러한 공지된 화합물의 활성은, 특히 낮은 적용 비율 및 농도로 사용하는 경우에, 모든 적용 분야에서 전적으로 완전히 만족스럽지는 않다.It is already known that certain aromatic carbothioamides, for example 2,6-dichlorobenzothioamide (“chlortiamide”), have herbicidal properties (GB-B 987253). However, the activity of such known compounds is not entirely satisfactory in all applications, especially when used at low application rates and concentrations.

본 발명에 따라 하기 일반식(I)의 신규한 치환된 방향족 티오카복스아미드가 밝혀졌다.According to the invention a novel substituted aromatic thiocarboxamide of the general formula (I)

상기 식에서,Where

R1은 수소 또는 할로겐을 나타내고,R 1 represents hydrogen or halogen,

R2는 그룹 -A1-A2-A3를 나타내며,R 2 represents a group -A 1 -A 2 -A 3 ,

여기에서,From here,

A1은 단일 결합을 나타내거나, 산소, 황, -SO-, -SO2-, -CO- 또는 그룹 -N-A4-(여기에서 A4는 수소, 하이드록실, 알킬, 알케닐, 알키닐, 알콕시, 아릴, 알킬설포닐 또는 아릴설포닐을 나타낸다)을 나타내거나,A 1 represents a single bond or is oxygen, sulfur, —SO—, —SO 2 —, —CO— or group —NA 4 —, where A 4 is hydrogen, hydroxyl, alkyl, alkenyl, alkynyl, Alkoxy, aryl, alkylsulfonyl or arylsulfonyl).

A1은 또한 각 경우에 임의로 치환된 알칸디익, 알켄디일, 알킨디일, 사이클로알칸디일, 사이클로알켄디일 또는 아렌디일을 나타내고,A 1 also in each case represents an optionally substituted alkanedik, alkenediyl, alkyndiyl, cycloalkanediyl, cycloalkenediyl or arerendiyl,

A2는 단일 결합을 나타내거나, 산소, 황, -SO-, -SO2-, -CO- 또는 그룹 -N-A4-(여기에서 A4는 수소, 하이드록실, 알킬, 알케널, 알키닐, 아릴, 알콕시, 알킬설포닐 또는 아릴설포닐을 나타낸다)을 나타내거나,A 2 represents a single bond, or oxygen, sulfur, —SO—, —SO 2 —, —CO— or group —NA 4 —, where A 4 is hydrogen, hydroxyl, alkyl, alkenal, alkynyl, Aryl, alkoxy, alkylsulfonyl or arylsulfonyl)

A2는 또한 각 경우에 임의로 치환된 알칸디일, 알켄디일, 알킨디일, 사이클로알칸디일, 사이클로알켄디일 또는 아렌디일을 나타내며,A 2 also represents in each case an optionally substituted alkanediyl, alkenediyl, alkyndiyl, cycloalkanediyl, cycloalkenediyl or arerendiyl,

A3은 수소, 하이드록실, 아미노, 시아노, 이소시아노, 티오시아네이토, 니트로, 카복실, 카바모일, 티오카바모일, 설포, 클로로설포닐 또는 할로겐을 나타내거나, 각 경우에 임의로 치환된 알킬, 알콕시, 알킬티오, 알킬설피닐, 알킬설포닐, 알킬아미노, 디알킬아미노, 알콕시카보닐, 디알콕시(티오)포스포릴, 알케닐, 알케닐옥시, 알케닐아미노, 알킬리덴아미노, 알케닐옥시카보닐, 알키닐, 알키닐옥시, 알키닐아미노, 알키닐옥시카보닐, 사이클로알킬, 사이클로알킬옥시, 사이클로알킬알킬, 사이클로알킬알콕시, 사이클로알킬리덴아미노, 사이클로알킬옥시카보닐, 사이클로알킬알콕시카보닐, 아릴, 아릴옥시, 아릴알킬, 아릴알옥시, 아릴옥시카보닐, 아릴알콕시카보닐, 혜테로사이클릴, 혜테로사이클릴알킬, 혜테로사이클릴알콕시 또는 혜테로사이클릴알콕시카보닐을 나타내고,A 3 represents hydrogen, hydroxyl, amino, cyano, isocyano, thiocyanato, nitro, carboxyl, carbamoyl, thiocarbamoyl, sulfo, chlorosulfonyl or halogen, or optionally substituted in each case Alkyl, alkoxy, alkylthio, alkylsulfinyl, alkylsulfonyl, alkylamino, dialkylamino, alkoxycarbonyl, dialkoxy (thio) phosphoryl, alkenyl, alkenyloxy, alkenylamino, alkylideneamino, al Kenyloxycarbonyl, alkynyl, alkynyloxy, alkynylamino, alkynyloxycarbonyl, cycloalkyl, cycloalkyloxy, cycloalkylalkyl, cycloalkylalkoxy, cycloalkylideneamino, cycloalkyloxycarbonyl, cycloalkyl Alkoxycarbonyl, aryl, aryloxy, arylalkyl, arylaloxy, aryloxycarbonyl, arylalkoxycarbonyl, heterocyclyl, heterocyclylalkyl, heterocyclylalkoxyalk or heterocyclyl Alkoxycarbonyl,

R3는 수소 또는 할로겐을 나타내거나, R2와 함께 임의로 개시부(또는 말단부)에 또는 탄화수소쇄 내에 산소원자, 황 원자, SO2그룹, NH 그룹, N-알킬 그룹, 카보닐 그룹 및/또는 티오카보닐 그룹을 함유하는 알칸디일 또는 알켄디일 그룹을 나타내며,R 3 represents hydrogen or halogen, optionally together with R 2 , at the beginning (or at the end) or in a hydrocarbon chain, an oxygen atom, a sulfur atom, a SO 2 group, an NH group, an N-alkyl group, a carbonyl group and / or An alkanediyl or alkenediyl group containing a thiocarbonyl group,

Z 는 각 경우에 임의로 치환된 모노사이클릭 또는 비사이클릭의 포화 또는 불포화 헤테로사이클릴, 혜테로사이클릴아미노 또는 헤테로사이클릴이미노를 나타낸다.Z represents in each case an optionally substituted monocyclic or bicyclic saturated or unsaturated heterocyclyl, heterocyclylamino or heterocyclylimino.

일반식 (I) 의 신규한 치환된 방향족 티오카복스아미드는 하기 일반식 (II) 의 치환된 방향족 니트릴을, 임의로 반응 보조제의 존재하 및 임의로 희석제의 존재하에서 황화수소(H2S)또는 티오아세트아미드와 반응시킴으로써 수득된다.The novel substituted aromatic thiocarboxamides of the general formula (I) are hydrogen sulfide (H 2 S) or thioacetic acid of the following substituted aromatic nitriles of the general formula (II), optionally in the presence of a reaction aid and optionally in the presence of a diluent. Obtained by reaction with an amide.

상기 식에서, R1R2, R3및 Z 는 상기 언급된 의미를 갖는다.Wherein R 1 R 2 , R 3 and Z have the meanings mentioned above.

일반식 (I) 의 신규한 치환된 방향족 티오카복스아미드는 강력하고 선택적인제초 활성을 나타낸다.The novel substituted aromatic thiocarboxamides of general formula (I) exhibit potent and selective herbicidal activity.

정의에서, 알킬, 알칸디일, 알케닐 또는 알키닐과 같은 포화 또는 불포화 탄화수소쇄는 단독으로 또는 알콕시, 알킬티오 또는 알킬아미노와 같이 헤테로 원자와 함깨 각각 직쇄 또는 측쇄이다.In the definition, saturated or unsaturated hydrocarbon chains such as alkyl, alkanediyl, alkenyl or alkynyl are each straight or branched chain alone or with heteroatoms such as alkoxy, alkylthio or alkylamino.

할로겐은 일반적으로 불소, 염소, 브롬 또는 요오드, 바람직하게는 불소, 염소 또는 브롬, 특히 불소 또는 염소를 나타낸다.Halogen generally represents fluorine, chlorine, bromine or iodine, preferably fluorine, chlorine or bromine, in particular fluorine or chlorine.

본 발명은 바람직하게는The present invention preferably

R1이 수소, 불소, 염소 또는 브롬을 나타내고,R 1 represents hydrogen, fluorine, chlorine or bromine,

R2는 그름 -A1-A2-A3를 나타내며,R 2 represents group -A 1 -A 2 -A 3 ,

여기에서,From here,

A1은 단일 결합을 나타내거나, 산소, 황, -SO-, -SO2-, -CO- 또는 그룹 -N-A4-(여기에서 A4는 수소, 하이드록실, C1-C4-알킬, C3-C4-알케닐, C3-C4-알키닐, C1-C4-알콕시, 페닐, C1-C4-알킬설포닐 또는 페닐설포닐을 나타낸다)을 나타내거나,A 1 represents a single bond or is oxygen, sulfur, —SO—, —SO 2 —, —CO— or a group —NA 4 —, where A 4 is hydrogen, hydroxyl, C 1 -C 4 -alkyl, C 3 -C 4 -alkenyl, C 3 -C 4 -alkynyl, C 1 -C 4 -alkoxy, phenyl, C 1 -C 4 -alkylsulfonyl or phenylsulfonyl).

A1은 또한 각 경우에 임의로 불소- 또는 염소-치환된 C1-C6-알칸디일, C2-C6-알켄디일, C2-C6-알킨디일, C3-C6-사이클로알칸디일, C3-C6-사이클로알켄디일 또는 페닐렌을 나타내고,A 1 is also optionally in each case fluorine- or chlorine-substituted C 1 -C 6 - alkanediyl, C 2 -C 6 - Al canned yl, C 2 -C 6 - alkynyl-diyl, C 3 -C 6 - Cycloalkanediyl, C 3 -C 6 -cycloalkenediyl or phenylene,

A2는 단일 결합을 나타내거나, 산소, 황, -SO-, -SO2-, -CO- 또는 그룹 -N-A4-(여기에서 A4는 수소, 하이드록실, C1-C4-알킬, C3-C4-알케닐, C3-C4-알키닐, C1-C4-알콕시, 페닐, C1-C4-알킬설포닐 또는 페닐설포닐을 나타낸다)을 나타내거나,A 2 represents a single bond or is oxygen, sulfur, —SO—, —SO 2 —, —CO— or group —NA 4 —, where A 4 is hydrogen, hydroxyl, C 1 -C 4 -alkyl, C 3 -C 4 -alkenyl, C 3 -C 4 -alkynyl, C 1 -C 4 -alkoxy, phenyl, C 1 -C 4 -alkylsulfonyl or phenylsulfonyl).

A2는 또한 각 경우에 임의로 불소- 또는 염소-치환된 C1-C6-알칸디일, C2-C6-알켄디일, C2-C6-알킨디일, C3-C6-사이클로알칸디일, C3-C6-사이클로알켄디일 또는 페닐렌을 나타내고,A 2 is also optionally in each case fluorine- or chlorine-substituted C 1 -C 6 - alkanediyl, C 2 -C 6 - Al canned yl, C 2 -C 6 - alkynyl-diyl, C 3 -C 6 - Cycloalkanediyl, C 3 -C 6 -cycloalkenediyl or phenylene,

A3은 수소, 하이드록실, 아미노, 시아노, 이소시아노, 티오시아네이토, 니트로, 카복실, 카바모일, 티오카바모일, 설포, 클로로설포닐 또는 할로겐을 나타내거나, 각 경우에 알킬 그룹에 1 내지 6 개의 탄소 원자를 가지며 각 경우에 임의로 할로겐- 또는 C1-C4-알콕시-치환된 알킬, 알콕시, 알킬티오, 알킬설피닐, 알킬설포닐, 알킬아미노, 디알킬아미노, 알콕시카보닐 또는 디알콕시(티오)포스포릴을 나타내거나, 각 경우에 알케닐, 알킬리덴 또는 알키닐 그룹에 2 내지 6 개의 탄소 원자를 가지며 각 경우에 임의로 할로겐-치환전 알케닐, 알케닐옥시, 알케닐아미노, 알킬리덴아미노, 알케닐옥시카보닐, 알키닐, 알키닐옥시, 알키닐아미노 또는 알키닐옥시카보닐을 나타내거나, 각 경우에 사이클로알킬 그룹에 3 내지 6 개의 탄소 원자 및 임의로 알킬 그룹에 1 내지 4 개의 탄소 원자를 가지며 각 경우에 임의로 할로겐-, 시아노-, 카복실-, C1-C4-알킬- 및/또는 C1-C4-알콕시-카보닐-치환된 사이클로알킬, 사이클로알킬옥시, 사이클로알킬알킬, 사이클로알킬알콕시, 사이클로알킬리덴아미노, 사이클로알킬옥시카보닐 또는 사이클로알킬알콕시카보닐을 나타내거나, 각 경우에 임의로 니트로-, 시아노-, 카복실-, 할로겐-, C1-C4-알킬-, C1-C4-할로게노알킬-, C1-C4-알킬옥시-, C1-C4-할로게노알킬옥시- 및/또는 C1-C4-알콕시-카보닐-치환된 페닐, 페닐옥시, 페닐-C1-C4-알킬, 페닐-C1-C4-알콕시, 페닐옥시카보닐 또는 페닐-C1-C4-알콕시카보닐, 각 경우에 임의로 완전히 또는 부분적으로 수소화된 피롤릴, 피라졸릴, 이미다졸릴, 트리아졸릴, 푸릴, 티에닐, 옥사졸릴, 이속사졸릴, 티아졸릴, 이소티아졸릴, 옥사디아졸릴, 티아디아졸릴, 피리디닐, 피리미디닐, 트리아지닐, 피라졸릴-C1-C4-알킬, 푸릴-C1-C4-알킬, 티에닐-C1-C4-알킬, 옥사졸릴-C1-C4-알킬, 이속사졸-C1-C4-알킬, 티아졸-C1-C4-알킬, 피리디닐-C1-C4-알킬, 피리미디닐-C1-C4-알킬, 피라졸릴메톡시 또는 푸릴메톡시를 나타내거나, 퍼하이드로피라닐메톡시 또는 피리딜메톡시를 나타내고,A 3 represents hydrogen, hydroxyl, amino, cyano, isocano, thiocyanato, nitro, carboxyl, carbamoyl, thiocarbamoyl, sulfo, chlorosulfonyl or halogen, in each case to an alkyl group Having 1 to 6 carbon atoms and in each case optionally halogen- or C 1 -C 4 -alkoxy-substituted alkyl, alkoxy, alkylthio, alkylsulfinyl, alkylsulfonyl, alkylamino, dialkylamino, alkoxycarbonyl Or dialkoxy (thio) phosphoryl, in each case having 2 to 6 carbon atoms in the alkenyl, alkylidene or alkynyl group and in each case optionally halogen-substituted alkenyl, alkenyloxy, alkenyl Amino, alkylideneamino, alkenyloxycarbonyl, alkynyl, alkynyloxy, alkynylamino or alkynyloxycarbonyl, or in each case 3 to 6 carbon atoms and optionally an alkyl group Having 1 to 4 carbon atoms in each case optionally halogen -, cyano-, carboxyl -, C 1 -C 4 - alkyl-and / or C 1 -C 4 - alkoxy-carbonyl-substituted cycloalkyl, cycloalkyl Alkyloxy, cycloalkylalkyl, cycloalkylalkoxy, cycloalkylideneamino, cycloalkyloxycarbonyl or cycloalkylalkoxycarbonyl, or in each case optionally nitro-, cyano-, carboxyl-, halogen-, C 1 -C 4 - alkyl -, C 1 -C 4 - halogenoalkyl -, C 1 -C 4 - alkyloxy -, C 1 -C 4 - halogenoalkyl oxy-and / or C 1 -C 4 - alkoxy - Carbonyl-substituted phenyl, phenyloxy, phenyl-C 1 -C 4 -alkyl, phenyl-C 1 -C 4 -alkoxy, phenyloxycarbonyl or phenyl-C 1 -C 4 -alkoxycarbonyl, in each case Optionally fully or partially hydrogenated pyrrolyl, pyrazolyl, imidazolyl, triazolyl, furyl, thienyl, oxazolyl, isoxazolyl, thiazolyl, isothiazolyl, Four thiadiazolyl, thiadiazolyl, pyridinyl, pyrimidinyl, triazinyl, pyrazolyl -C 1 -C 4 - alkyl, furyl -C 1 -C 4 - alkyl, thienyl -C 1 -C 4 - alkyl, oxazolyl -C 1 -C 4 - alkyl, isoxazol--C 1 -C 4 - alkyl, thiazol--C 1 -C 4 - alkyl, pyridinyl -C 1 -C 4 - alkyl, -C 1-pyrimidinyl -C 4 -alkyl, pyrazolylmethoxy or furylmethoxy, or perhydropyranylmethoxy or pyridylmethoxy,

R3는 수소, 불소, 염료 또는 브롬을 나타내거나, R2와 함께 각 경우에 4 개 이하의 탄소 원자를 가지며 임의로 개시부(또는 말단부)에 또는 탄화수소쇄 내에 산소원자, 황 원자, SO2그룹, NH 그룹, N-C1-C4-알킬 그룹, 카보닐 그룹 및/또는 티오카보닐 그룹을 함유하는 알칸디일 또는 알켄디일 그룹을 나타내며,R 3 represents hydrogen, fluorine, dye or bromine or, together with R 2 , has up to 4 carbon atoms in each case and optionally an oxygen atom, a sulfur atom, a SO 2 group at the initiation (or end) or in the hydrocarbon chain; , An alkanediyl or alkenediyl group containing an NH group, an NC 1 -C 4 -alkyl group, a carbonyl group and / or a thiocarbonyl group,

Z 는 각 경우에 헤테펄사이클릭 환 계에 1 내지 4개의 질소 원자 및 2 내지 8개의 탄소 원자를 가지며 임의로 산소 원자 또는 황 원자 및/또는 임의로 -CO-, -CS-, -SO- 및/또는 SO2- 중에서 선택된 3개 이하의 그룹을 함유하고 니트로, 하이드록실, 아미노, 시아노, 카복실, 카바모일, 티오카바모일, 할로겐, C1-C6-알킬(할로겐 또는 C1-C4-알콕시에 의해 임의로 치환된다), C2-C6-알케닐 및 C2-C6-알키닐(이들은 각 경우에 할로겐에 의해 임의로 치환된다), C1-C6-알콕시 및 C1-C6-알콕시카보닐(이들은 각 경우에 할로겐 또는 C1-C4-알콕시에 의해 임의로 치환된다), C2-C6-알케닐옥시 및 C2-C6-알키닐옥시(이들은 각 경우에 할로겐에 의해 임의로 치환된다), C1-C6-알킬티오, C2-C6-알케닐티오 및 C2-C6-알키닐티오(이들은 각 경우에 할로겐에 의해 임의로 치환된다), C1-C6-알킬아미노 및 디-(C1-C4-알킬)-아미노, C3-C6-사이클로알킬 및 C3-C6-사이클로알킬-C1-C4-알킬(이들은 각 경우에 할로겐 및/또는 C1-C4-알킬에 의해 임의로 치환된다), 및 페닐, 페녹시, 페닐티오, 페닐설피닐, 페닐설포닐 또는 페닐아미노(이들은 각 경우에 니트로, 시아노, 할로겐, C1-C4-알킬, C1-C4-할로게노알킬, C1-C4-알킬옥시, C1-C4-할로게노알킬옥시 및/또는 C1-C4-알콕시카보닐에 의해 임의로 치환된다)로 구성된 그룹중에서 선택된 하나 이상의 그룹에 의해 임의로 치환되고 각 경우에 모노사이클릭 또는 비사이클릭인 포화 또는 불포화 헤테로사이클릴, 해테로사이클릴아미노 또는 헤테로사이클릴이미노를 나타내는 일반식 (I) 의 화합물에 관한 것이다.Z in each case has 1 to 4 nitrogen atoms and 2 to 8 carbon atoms in the heterocyclic ring system and optionally an oxygen atom or a sulfur atom and / or optionally -CO-, -CS-, -SO- and / Or up to 3 groups selected from SO 2 -and nitro, hydroxyl, amino, cyano, carboxyl, carbamoyl, thiocarbamoyl, halogen, C 1 -C 6 -alkyl (halogen or C 1 -C 4 -Optionally substituted by alkoxy), C 2 -C 6 -alkenyl and C 2 -C 6 -alkynyl, which in each case are optionally substituted by halogen, C 1 -C 6 -alkoxy and C 1- C 6 -alkoxycarbonyl, which in each case is optionally substituted by halogen or C 1 -C 4 -alkoxy, C 2 -C 6 -alkenyloxy and C 2 -C 6 -alkynyloxy, which in each case Is optionally substituted by halogen), C 1 -C 6 -alkylthio, C 2 -C 6 -alkenylthio and C 2 -C 6 -alkynylthio, which in each case are optionally substituted by halogen ), C 1 -C 6 -alkylamino and di- (C 1 -C 4 -alkyl) -amino, C 3 -C 6 -cycloalkyl and C 3 -C 6 -cycloalkyl-C 1 -C 4 -alkyl, which in each case is optionally substituted by halogen and / or C 1 -C 4 -alkyl, and phenyl, phenoxy, phenylthio, phenylsulfinyl, phenylsulfonyl or phenylamino in each case Nitro, cyano, halogen, C 1 -C 4 -alkyl, C 1 -C 4 -halogenoalkyl, C 1 -C 4 -alkyloxy, C 1 -C 4 -halogenoalkyloxy and / or C 1- Saturated or unsaturated heterocyclyl, heterocyclylamino or hetero optionally substituted by one or more groups selected from the group consisting of C 4 -alkoxycarbonyl) and in each case monocyclic or bicyclic It relates to a compound of the general formula (I) representing cyclimino.

본 발명은 특히The present invention is particularly

R1이 수소, 불소 또는 염소를 나타내고,R 1 represents hydrogen, fluorine or chlorine,

R2는 그룹 -A1-A2-A3를 나타내며,R 2 represents a group -A 1 -A 2 -A 3 ,

여기에서,From here,

A1은 단일 결합을 나타내거나, 산소, 황, -SO-, -SO2-, -CO- 또는 그룹 -N-A4-(여기에서 A4는 수소, 하이드록실, 메틸, 애틸, n- 또는 i-프로필, 메톡시, 에톡시, n- 또는 i-프로폭시, 메틸설포닐, 또는 에틸설포닐을 나타낸다)을 나타내거나,A 1 represents a single bond or is oxygen, sulfur, -SO-, -SO 2- , -CO- or group -NA 4- (wherein A 4 is hydrogen, hydroxyl, methyl, ethyl, n- or i -Propyl, methoxy, ethoxy, n- or i-propoxy, methylsulfonyl, or ethylsulfonyl).

A1은 또한 메틸렌, 에탄-1,1-디일, 에탄-1,2-디일, 프로판-1,1-디일, 프로판-1,2-디일, 프로판-1,3-디일, 에텐-1,2-디일, 프로펜-1,2-티일, 프로펜-1,3-디일, 에틴-1,2-디일, 프로핀-1,2--디일 또는 프로핀-1,3-디일을 나타내고,A 1 is also methylene, ethane-1,1-diyl, ethane-1,2-diyl, propane-1,1-diyl, propane-1,2-diyl, propane-1,3-diyl, ethene-1, 2-diyl, propene-1,2-thiyl, propene-1,3-diyl, ethyn-1,2-diyl, propyne-1,2--diyl or propyne-1,3-diyl ,

A2는 단일 결합을 나타내거나, 산소, 황, -SO-, -SO2-, -CO- 또는 그룹 -N-A4-(여기에서 A4는 수소, 하이드록실, 메틸, 에틸, n- 또는 i-프로필, 메톡시, 에톡시, n- 또는 i-프로폭시, 메틸설포닐, 에틸설포닐, n- 또는 i-프로필설포닐, 또는 페닐설포닐을 나타낸다)을 나타내거나,A 2 represents a single bond or is oxygen, sulfur, —SO—, —SO 2 —, —CO— or a group —NA 4 —, where A 4 is hydrogen, hydroxyl, methyl, ethyl, n- or i -Propyl, methoxy, ethoxy, n- or i-propoxy, methylsulfonyl, ethylsulfonyl, n- or i-propylsulfonyl, or phenylsulfonyl).

A2는 또한 메틸렌, 에탄-1,1-디일, 에탄-1,2-디일, 프로판-1,1-디일, 프로판-1,2-디일, 프로판-1,3-디일, 에텐-1,2-디일, 프로펜-1,2-디일, 프로펜-1,3-디일, 에틸-1,2-디일, 프로핀-1,2-디일 또는 프로핀-1,3-디일을 나타내고,A 2 is also methylene, ethane-1,1-diyl, ethane-1,2-diyl, propane-1,1-diyl, propane-1,2-diyl, propane-1,3-diyl, ethene-1, 2-diyl, propene-1,2-diyl, propene-1,3-diyl, ethyl-1,2-diyl, propyne-1,2-diyl or propyne-1,3-diyl,

A3은 수소, 하이드록실, 아미노, 시아노, 니트로, 카복실, 카바모일, 설포, 불소, 염소 또는 브롬을 나타내거나, 각 경우에 임의로 불소-, 염소-, 메톡시- 또는 에톡시-치환된 메틸, 에틸, n- 또는 i-프로필, n-, i-, s- 또는 t-부틸, n-, i-, s- 또는 t-펜틸, 메톡시, 에톡시, n- 또는 i-프로폭시, n-, i-, s- 또는 t-부톡시, n-, i-, s- 또는 t-펜틸옥시, 메틸티오, 에틸티오, n- 또는 i-프로필티오, n-, i-, s- 또는 t-부틸티오, 메틸설피닐, 에틸설피닐, n- 또는 i-프로필설피닐, 메틸설포닐, 에틸설포닐, n- 또는 i-프로필설포닐, 메틸아미노, 에틸아미노, n- 또는 i-프로필아미노, n-, i-, s- 또는 t-부틸아미노, 디메틸아미노, 디에틸아미노, 메톡시카보닐, 애톡시카보닐, n- 또는 i-프로폭시카보닐, 디메톡시포스포릴, 디에톡시포스포릴, 디프로폭시포스포릴, 또는 디이소프로폭시포스포릴을 나타내거나, 각 경우에 임의포 불소- 또는 염소-치환된 프로페닐, 부테닐, 프로페닐옥시, 부테닐옥시, 프로페닐아미노, 부테닐아미노, 프로필리덴아미노, 부틸리덴아미노, 프로페닐옥시카보닐, 부테닐옥시카보닐, 프로피닐, 부티닐, 프로피닐옥시, 부티닐옥시, 프로피닐아미노, 부티닐아미노, 프로피닐옥시카보닐, 부티닐옥시카보닐을 나타내거나, 각 경우에 임의로 불소-, 염소-, 시아노, 카복실-, 메틸-, 에틸-, n- 또는 i-프로필-, 메톡시카보닐-, 또는 에톡시카보닐-치환된 사이클로프로필, 사이클로부틸, 사이클로펜틸, 사이클로헥실, 사이클로프로필옥시, 사이클로부틸옥시, 사이클로펜틸옥시, 사이클로헥실옥시, 사이클로프로필메틸, 사이클로부틸메틸, 사이클로펜틸메틸, 사이클로헥실메틸, 사이클로프로필메톡시, 사이클로부틸메톡시, 사이클로펜틸메톡시, 사이클로헥실메톡시, 사이클로펜틸리덴아미노, 사이클로헥실리덴아미노, 사이클로펜틸옥시카보닐, 사이클로헥실옥시카보닐, 사이클로펜틸메톡시카보닐 또는 사이클로헥실메톡시카보닐을 나타내거나, 각 경우에 임의로 니트로-, 시아노-, 카복실-, 불소-, 염소-, 브롬-, 메틸-, 에틸-, n- 또는 i-프로필-, 트리플루오로메틸-, 메톡시-, 에톡시-, n- 또는 i-프로폭시-, 디플루오로메톡시-, 트리플루오로메톡시-, 메톡시카보닐- 및/또는 에톡시카보닐-치환된 페닐, 페닐옥시, 벤질, 페닐에틸, 벤질옥시, 페닐옥시카보닐, 벤질옥시카보닐, 각 경우에 임의로 완전히 또는 부분적으로 수소화된 피롤릴, 피라졸릴, 이미다졸릴, 트리아졸릴, 푸릴, 티에닐, 옥사졸릴, 이속사졸릴, 티아졸릴, 이소티아졸릴, 옥사디아졸릴, 티아디아졸릴, 피리디닐, 피리미디닐, 트리아지닐, 피라졸릴메틸, 푸릴메틸, 티에닐메틸, 옥사졸릴메틸, 이속사졸메틸, 티아졸메틸, 피리디닐메틸, 피리미디닐메틸, 피라졸릴메톡시, 푸릴메톡시 또는 피리딜메톡시를 나타내고,A 3 represents hydrogen, hydroxyl, amino, cyano, nitro, carboxyl, carbamoyl, sulfo, fluorine, chlorine or bromine, or in each case optionally fluorine-, chlorine-, methoxy- or ethoxy-substituted Methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, n-, i-, s- or t-pentyl, methoxy, ethoxy, n- or i-propoxy , n-, i-, s- or t-butoxy, n-, i-, s- or t-pentyloxy, methylthio, ethylthio, n- or i-propylthio, n-, i-, s Or t-butylthio, methylsulfinyl, ethylsulfinyl, n- or i-propylsulfinyl, methylsulfonyl, ethylsulfonyl, n- or i-propylsulfonyl, methylamino, ethylamino, n- or i-propylamino, n-, i-, s- or t-butylamino, dimethylamino, diethylamino, methoxycarbonyl, ethoxycarbonyl, n- or i-propoxycarbonyl, dimethoxyphosphoryl , Diethoxyphosphoryl, dipropoxyphosphoryl, or diisopropoxyphosphoryl Fluorine- or chlor-substituted propenyl, butenyl, propenyloxy, butenyloxy, propenylamino, butenylamino, propylideneamino, butylideneamino, propenyloxycarbo Nil, butenyloxycarbonyl, propynyl, butynyl, propynyloxy, butynyloxy, propynylamino, butynylamino, propynyloxycarbonyl, butynyloxycarbonyl, or in each case optionally fluorine Chlorine-, cyano, carboxyl-, methyl-, ethyl-, n- or i-propyl-, methoxycarbonyl-, or ethoxycarbonyl-substituted cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl , Cyclopropyloxy, cyclobutyloxy, cyclopentyloxy, cyclohexyloxy, cyclopropylmethyl, cyclobutylmethyl, cyclopentylmethyl, cyclohexylmethyl, cyclopropylmethoxy, cyclobutylmethoxy, cyclopene Butylmethoxy, cyclohexylmethoxy, cyclopentylideneamino, cyclohexylideneamino, cyclopentyloxycarbonyl, cyclohexyloxycarbonyl, cyclopentylmethoxycarbonyl or cyclohexylmethoxycarbonyl, or each Optionally nitro-, cyano-, carboxyl-, fluorine-, chlorine-, bromine-, methyl-, ethyl-, n- or i-propyl-, trifluoromethyl-, methoxy-, ethoxy-, n- or i-propoxy-, difluoromethoxy-, trifluoromethoxy-, methoxycarbonyl- and / or ethoxycarbonyl-substituted phenyl, phenyloxy, benzyl, phenylethyl, benzyloxy, phenyl Oxycarbonyl, benzyloxycarbonyl, in each case optionally fully or partially hydrogenated pyrrolyl, pyrazolyl, imidazolyl, triazolyl, furyl, thienyl, oxazolyl, isoxazolyl, thiazolyl, isothiazolyl , Oxadiazolyl, thiadiazolyl, pyridinyl, pyrimidinyl, t Represents an azinyl, pyrazolyl-methyl, furylmethyl, thienylmethyl, oxazolyl methyl, isoxazole methyl, thiazol-methyl, pyridinyl-methyl, pyrimidinyl, methyl, pyrazolyl-methoxy, Fu rilme ethoxy or pyrido dilme ethoxy,

R3는 수소, 불소 또는 염소를 나타내거나, R2와 함께 각 경우에 1 내지 3 개의 탄소 원자를 가지며 임의로 개시부(또는 말단부)에 또는 탄화수소쇄 내에 산소원자, 황 원자, NH 그룹, N-메틸 그룹, 카보닐 그룹 및/또는 티오카보닐 그룹을 함유하는 알칸디일 또는 알켄디일 그룹을 나타내며,R 3 represents hydrogen, fluorine or chlorine, or together with R 2 in each case has 1 to 3 carbon atoms and optionally at the beginning (or at the end) an oxygen atom, sulfur atom, NH group, N— An alkanediyl or alkenediyl group containing a methyl group, a carbonyl group and / or a thiocarbonyl group,

Z 는 각 경우에 헤테로사이클릭 환 계에 1 내지 3 개의 질소 원자 및 2 내지 8개의 탄소 원자를 가지며 임의로 산소 원자 또는 황 원자 및/또는 임의로 -CO-, -CS-, -SO- 및/또는 SO2- 중에서 선택된. 2 개 이하의 그룹을 함유하고 니트로, 하이드록실, 아미노, 시아노, 카복실, 카바모일, 티오카바모일, 불소, 염소, 브롬; 메틸, 에틸, n- 또는 i-프로필, 또는 n-, i-, s- 또는 t-부틸(이들은 각 경우에 불소, 염소, 메톡시 또는 에톡시에 의해 임의로 치환된다); 프로페닐, 부테닐, 프로피닐 또는 부티닐(이들은 각 경우에 불소 또는 염소에 의해 임의로 치환된다:); 메톡시, 에톡시, n- 또는 i-프로폭시, n-, i-, s- 또는 t-부톡시, 메톡시카보닐, 또는 에톡시카보닐(이들은 각 경우에 불소, 염소, 메톡시 또는 에톡시에 의해 임의로 치환된다); 프로페닐옥시, 부테닐옥시, 프로피닐옥시 또는 부티닐옥시(이들은 각 경우에 불소 또는 염소에 의해 임의로 치환된다); 메틸티오, 에틸티오, n- 또는 i-프로필티오, n-, i-, s-- 또는 t-부틸티오, 프로페닐티오, 부테닐티오, 프로피닐티오, 또는 부티닐티오(이들은 각 경우에 불소 또는 염소에의해 임의로 치환된다); 메틸아미노, 에틸아미노, n- 또는 i-프로필아미노, n-, i-, s- 또는 t-부틸아미노, 디메틸아미노, 또는 디에틸아미노: 사이클로프로필, 사이클로부틸, 사이클로펜틸, 사이클로헥실, 사이클로프로필메틸, 사이클로부틸메틸, 사이클로펜틸메틸 또는 사이클로헥실메틸(이들은 각 경우에 불소, 염소, 메틸, 에틸, n- 또는 i-프로필에 의해 임의로 치환된다), 페닐, 페녹시, 페닐티오, 페닐설피닐, 페닐설포닐 또는 페닐아미노(이들은 각 경우에 니트로, 시아노, 불소, 염소, 브롬, 메틸, 에틸, n- 또는i-프로필, 트리플루오로메틸, 메톡시, 에톡시, n- 또는 1-프로폭시, 디플루오로메톡시, 트리플루오로메톡시, 메톡시카보닐, 또는 에톡시카보닐에 의해 임의로 치환된다)로 구성된 그룹중에서 선택된 하나 이상의 그룹에 의해 임의로 치환되고 각 경우에 모노사이클릭 또는 비사이클릭인 포화 또는 불포화 헤테로사이클릴, 헤테로사이클릴아미노 또는 헤테로사이클릴아미노를 나타내는 일반식 (I) 의 화합물에 관한 것이다.Z has in each case 1 to 3 nitrogen atoms and 2 to 8 carbon atoms in the heterocyclic ring system and optionally an oxygen atom or a sulfur atom and / or optionally -CO-, -CS-, -SO- and / or SO 2 -selected from. Nitro, hydroxyl, amino, cyano, carboxyl, carbamoyl, thiocarbamoyl, fluorine, chlorine, bromine; Methyl, ethyl, n- or i-propyl, or n-, i-, s- or t-butyl (they are optionally substituted in each case by fluorine, chlorine, methoxy or ethoxy); Propenyl, butenyl, propynyl or butynyl (they are optionally substituted in each case by fluorine or chlorine); Methoxy, ethoxy, n- or i-propoxy, n-, i-, s- or t-butoxy, methoxycarbonyl, or ethoxycarbonyl (these are in each case fluorine, chlorine, methoxy or Optionally substituted by ethoxy); Propenyloxy, butenyloxy, propynyloxy or butynyloxy, which in each case are optionally substituted by fluorine or chlorine; Methylthio, ethylthio, n- or i-propylthio, n-, i-, s-- or t-butylthio, propenylthio, butenylthio, propynylthio, or butynylthio (these are in each case Optionally substituted by fluorine or chlorine); Methylamino, ethylamino, n- or i-propylamino, n-, i-, s- or t-butylamino, dimethylamino, or diethylamino: cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cyclopropyl Methyl, cyclobutylmethyl, cyclopentylmethyl or cyclohexylmethyl (they are optionally substituted in each case by fluorine, chlorine, methyl, ethyl, n- or i-propyl), phenyl, phenoxy, phenylthio, phenylsulfinyl , Phenylsulfonyl or phenylamino (these in each case are nitro, cyano, fluorine, chlorine, bromine, methyl, ethyl, n- or i-propyl, trifluoromethyl, methoxy, ethoxy, n- or 1- Optionally substituted by one or more groups selected from the group consisting of propoxy, difluoromethoxy, trifluoromethoxy, methoxycarbonyl, or ethoxycarbonyl) and in each case are monocyclic or It relates to a compound of formula (I) which represents a saturated or unsaturated heterocyclyl, heterocyclylamino or heterocyclylamino which is acyclic.

일반식 (I) 의 매우 특히 바람직한 그룹은 하기 일반식 (Ia), (Ib) 및 (Ic)의 화합물이다:Very particularly preferred groups of general formula (I) are compounds of the general formulas (Ia), (Ib) and (Ic):

상기 식에서,Where

R1, R2및 Z는 상기에 특히 바람직한 것으로 언급된 의미를 가지며,R 1 , R 2 and Z have the meanings mentioned as particularly preferred above,

R4및 R5는 동일하거나 상이하고 서로 독립적으로 각 경우에 수소, 불소, 염소, 메틸 또는 에틸을 나타내거나, 일반식 (Ib)에서는 또한 이들이 함께 산소 또는 황을 나타내고,R 4 and R 5 are the same or different and independently from each other represent in each case hydrogen, fluorine, chlorine, methyl or ethyl, or in general formula (Ib) they together represent oxygen or sulfur,

Q는 산소, 황, N-메틸 또는 N-에틸을 나타낸다.Q represents oxygen, sulfur, N-methyl or N-ethyl.

일반식 (I), (Ia), (Ib) 및 (Ic) 에서 Z 는 특히 다음에 기재된 헤테로사이클릭 그룹을 나타낸다.Z in general formulas (I), (Ia), (Ib) and (Ic) in particular represent the heterocyclic groups described below.

상기 식에서, 각 경우에In the above formula, in each case

Q1은 -CO-, -CS-, -CH2-, -CH(OH)-, -CHCl-, -CHBr-, -C(=CH2)-, -C(=CHF)-, -C(=CF2)-, -C(=CHCl)-, -C(=CHBr)-, -C(=CHOCHF2)-, -C(=CHOCF3)- 및 -C(=CHOCH2CF3)- 로 구성된 그룹중에서 선택된 그룹을 나타내고,Q 1 is -CO-, -CS-, -CH 2- , -CH (OH)-, -CHCl-, -CHBr-, -C (= CH 2 )-, -C (= CHF)-, -C (= CF 2 )-, -C (= CHCl)-, -C (= CHBr)-, -C (= CHOCHF 2 )-, -C (= CHOCF 3 )-and -C (= CHOCH 2 CF 3 ) -Represents a group selected from the group consisting of

Q2는 산소, 황, 또는 -CO-, -CS-, -CH2-, -CHF-, -CF2-, -CHCl-, -CHBr-, -CHOCHF2-, -CHOCF3- 및 -CHOCH2CF3- 로 구성된 그룹중에서 선택된 그룹을 나타내며,Q 2 is oxygen, sulfur, or -CO-, -CS-, -CH 2- , -CHF-, -CF 2- , -CHCl-, -CHBr-, -CHOCHF 2- , -CHOCF 3 -and -CHOCH 2 CF 3 -represents the group selected from the group consisting of

R6은 수소, 아미노, 니트로, 시아노, 카복실, 카바모일, 불소, 염소, 브롬, 메틸, 에틸, n- 또는 i-프로필, 사이클로프로필, 디플루오로메틸, 프리플루오로메틸, 클로로디플루오로메틸, 메톡시, 에톡시, n- 또는 i-프로폭시, 디플루오로메톡시, 트리플루오로메톡시, 클로로디플루오로메톡시, 메틸티오, 에틸티오, n- 또는 i-프로필티오, 디플루오로메틸티오, 트리플루오로메틸티오, 클로로디플루오로메틸티오, 메틸아미노, 에틸아미노, n- 또는 i-프로필아미노, 디메틸아미노, 디에틸아미노, 메톡시카보닐, 또는 에톡시카보닐을 나타내고,R 6 is hydrogen, amino, nitro, cyano, carboxyl, carbamoyl, fluorine, chlorine, bromine, methyl, ethyl, n- or i-propyl, cyclopropyl, difluoromethyl, prefluoromethyl, chlorodifluoro Rhomethyl, methoxy, ethoxy, n- or i-propoxy, difluoromethoxy, trifluoromethoxy, chlorodifluoromethoxy, methylthio, ethylthio, n- or i-propylthio, difluoro Methylthio, trifluoromethylthio, chlorodifluoromethylthio, methylamino, ethylamino, n- or i-propylamino, dimethylamino, diethylamino, methoxycarbonyl, or ethoxycarbonyl;

R7은 수소, 하이드록실, 아미노, 시아노, 메틸, 에틸, n- 또는 i-프로필, 디플루오로메틸, 메톡시, 에톡시, 또는 n- 또는 i-프로폭시를 나타내거나, 임의로 인접한 그룹 R5및 R6또는 R7및 R7또는 R6및 R7과 함께 각 경우에 4 개 이하의 탄소 원자를 가지며 임의로 개시부(또는 말단부)에서 또는 탄화수소쇄 내에서 산소, 황 또는 -SO-, SO2-, -N(CH3)- 및 N(C2H5)- 로 구성된 그룹중에서 선택된 그룹에 의해 임의로 차단되고 각 경우에 임의로 불소-, 염소-, 브롬-, 메틸-, 에틸-, n- 또는 i-프로필-치환된 알칸디일 또는 알켄디일 그룹을 나타낸다.R 7 represents hydrogen, hydroxyl, amino, cyano, methyl, ethyl, n- or i-propyl, difluoromethyl, methoxy, ethoxy, or n- or i-propoxy, or an optionally adjacent group Together with R 5 and R 6 or R 7 and R 7 or R 6 and R 7 in each case up to 4 carbon atoms and optionally oxygen, sulfur or —SO— at the initiation (or end) or in the hydrocarbon chain; , Is optionally interrupted by a group selected from the group consisting of, SO 2- , -N (CH 3 )-and N (C 2 H 5 )-and in each case is optionally fluorine-, chlorine-, bromine-, methyl-, ethyl- , n- or i-propyl-substituted alkanediyl or alkenediyl groups.

일반적이거나 바람직한 것으로 상기에서 언급한 라디칼의 정의는 일반식 (I) 의 최종 생성물 및, 또한 상응하게 제조에 필요한 출발 물질 및 중합체에 각각 적용된다. 이들 라디칼의 정의를 목적하는 대로 서로 조합할 수 있고, 따라서 지정한바람직한 범위 사이에서 목적하는 대로 마음대로 조합할 수 있다.The definitions of the radicals mentioned above as general or preferred apply respectively to the final product of general formula (I) and also to the starting materials and polymers correspondingly required for the preparation. The definitions of these radicals can be combined with each other as desired, and therefore can be combined freely as desired between the specified ranges.

본 발명에 따른 일반식 (I) 의 화합물의 예를 하기 그룹으로 나타내었다.Examples of compounds of the general formula (I) according to the invention are shown in the following groups.

그룹 1Group 1

상기 식에서, R1, R2및 R3는 하기 지정된 의미를 갖는다 :Wherein R 1 , R 2 and R 3 have the meanings specified below:

그룹 2Group 2

상기 식에서, R1, R2및 R3는 예를 들어 그룹 1 에서 제시된 의미를 갖는다.Wherein R 1 , R 2 and R 3 have the meanings given for example in group 1.

그룹 3Group 3

상기 식에서, R1, R2및 R3는 예를 들어 그룹 1 에서 제시된 의미를 갖는다.Wherein R 1 , R 2 and R 3 have the meanings given for example in group 1.

그룹 4Group 4

상기 식에서, R1, R2및 R3는 예를 들어 그룹 1 에서 제시된 의미를 갖는다.Wherein R 1 , R 2 and R 3 have the meanings given for example in group 1.

그룹 5Group 5

상기 식에서, R1, R2및 R3는 예를 들어 그룹 1 에서 제시된 의미를 갖는다.Wherein R 1 , R 2 and R 3 have the meanings given for example in group 1.

그룹 6Group 6

상기 식에서, R1, R2및 R3는 예를 들어 그룹 1 에서 제시된 의미를 갖는다.Wherein R 1 , R 2 and R 3 have the meanings given for example in group 1.

그룹 7Group 7

상기 식에서, R1, R2및 R3는 예를 들어 그룹 1 에서 제시된 의미를 갖는다.Wherein R 1 , R 2 and R 3 have the meanings given for example in group 1.

그룹 8Group 8

상기 식에서, R1, R2및 R3는 예를 들어 그를 1 에서 제시된 의미를 갖는다.Wherein R 1 , R 2 and R 3 have the meaning given for example in 1 above.

그룹 9Group 9

상기 식에서, R1, R2및 R3는 예를 들어 그룹 1 에서 제시된 의미를 갖는다.Wherein R 1 , R 2 and R 3 have the meanings given for example in group 1.

그룹 10Group 10

상기 식에서, R1, R2및 R3는 예를 들어 그룹 1 에서 제시된 의미를 갖는다.Wherein R 1 , R 2 and R 3 have the meanings given for example in group 1.

그룹 11Group 11

상기 식에서, R1, R2및 R3는 예를 들어 그룹 1 에서 제시된 의미를 갖는다.Wherein R 1 , R 2 and R 3 have the meanings given for example in group 1.

그룹 12Group 12

상기 식에서, R1, R2및 R3는 예를 들어 그룹 1 애서 제시된 의미를 갖는다.Wherein R 1 , R 2 and R 3 have the meanings given for example in group 1.

그룹 13Group 13

상기 식에서, R1, R2및 R3는 예를 들어 그룹 1 에서 제시된 의미를 갖는다.Wherein R 1 , R 2 and R 3 have the meanings given for example in group 1.

그룹 14Group 14

상기 식에서, R1, R2및 R3는 예를 들어 그룹 1 에서 제시된 의미를 갖는다.Wherein R 1 , R 2 and R 3 have the meanings given for example in group 1.

그룹 15Group 15

상기 식에서, R1, R2및 R3는 예를 들어 그룹 1 에서 제시된 의미를 갖는다.Wherein R 1 , R 2 and R 3 have the meanings given for example in group 1.

그룹 16Group 16

상기 식에서, R1, R2및 R3는 예를 들어 그룹 1 에서 제시된 의미를 갖는다.Wherein R 1 , R 2 and R 3 have the meanings given for example in group 1.

그룹 17Group 17

상기 식에서, R1, R2및 R3는 예를 들어 그룹 1 에서 제시된 의미를 갖는다.Wherein R 1 , R 2 and R 3 have the meanings given for example in group 1.

그룹 18Group 18

상기 식에서, R1, R2및 R3는 예를 들어 그름 1 에서 제시된 의미를 갖는다.In the above formula, R 1 , R 2 and R 3 have the meanings given for example in 1.

그룹 19Group 19

상기 식에서, R1, R2및 R3는 예를 들어 그룹 1 에서 제시된 의미를 갖는다.Wherein R 1 , R 2 and R 3 have the meanings given for example in group 1.

그룹 20Group 20

상기 식에서, R1, R2및 R3는 예를 들어 그름 1 에서 제시된 의미를 갖는다.In the above formula, R 1 , R 2 and R 3 have the meanings given for example in 1.

그룹 21Group 21

상기 식에서, R1, R2및 R3는 예를 들어 그룹 1 에서 제시된 의미를 갖는다.Wherein R 1 , R 2 and R 3 have the meanings given for example in group 1.

그룹 22Group 22

상기 식에서, R1, R2및 R3는 예를 들어 그룹 1 에서 제시된 의미를 갖는다.Wherein R 1 , R 2 and R 3 have the meanings given for example in group 1.

그룹 23Group 23

상기 식에서, R1, R2및 R3는 예를 들어 그룹 1 에서 제시된 의미를 갖는다.Wherein R 1 , R 2 and R 3 have the meanings given for example in group 1.

그룹 24Group 24

상기 식에서, R1, R2및 R3는 예를 들어 그룹 1 에서 제시된 의미를 갖는다.Wherein R 1 , R 2 and R 3 have the meanings given for example in group 1.

그룹 25Group 25

상기 식에서, R1, R2및 R3는 예를 들어 그룹 1 에서 제시된 의미를 갖는다.Wherein R 1 , R 2 and R 3 have the meanings given for example in group 1.

그룹 26Group 26

상기 식에서, R1, R2및 R3는 예를 들어 흐름 1 에서 제시된 의미를 갖는다.Wherein R 1 , R 2 and R 3 have the meanings given for example in flow 1.

그룹 27Group 27

상기 식에서, R1, R2및 R3는 예를 들어 그룹 1 에서 제시된 의미를 갖는다.Wherein R 1 , R 2 and R 3 have the meanings given for example in group 1.

그룹 28Group 28

상기 식에서, R1, R2및 R3는 예를 들어 그룹 1 에서 제시된 의미를 갖는다.Wherein R 1 , R 2 and R 3 have the meanings given for example in group 1.

그룹 29Group 29

상기 식에서, R1, R2및 R3는 예를 들어 그룹 1 에서 제시된 의미를 갖는다.Wherein R 1 , R 2 and R 3 have the meanings given for example in group 1.

그룹 30Group 30

상기 식에서, R1, R2및 R3는 예를 들어 그룹 1 애서 제시된 의미를 갖는다.Wherein R 1 , R 2 and R 3 have the meanings given for example in group 1.

그룹 31Group 31

상기 식에서, R1, R2및 R3는 예를 들어 그룹 1 에서 제시된 의미를 갖는다.Wherein R 1 , R 2 and R 3 have the meanings given for example in group 1.

그룹 32Group 32

상기 식에서, R1, R2및 R3는 예를 들어 그룹 1 에서 제시된 의미를 갖는다.Wherein R 1 , R 2 and R 3 have the meanings given for example in group 1.

그룹 33Group 33

상기 식에서, R1, R2및 R3는 예를 들어 그룹 1 에서 제시된 의미를 갖는다.Wherein R 1 , R 2 and R 3 have the meanings given for example in group 1.

그룹 34Group 34

상기 식에서, R1, R2및 R3는 예를 들어 그룹 1 에서 제시된 의미를 갖는다.Wherein R 1 , R 2 and R 3 have the meanings given for example in group 1.

그룹 35Group 35

상기 식에서, R1, R2및 R3는 예를 들어 그룹 1 에서 제시된 의미를 갖는다.Wherein R 1 , R 2 and R 3 have the meanings given for example in group 1.

그룹 36Group 36

상기 식에서, R1, R2및 R3는 예를 들어 그룹 1 에서 제시된 의미를 갖는다.Wherein R 1 , R 2 and R 3 have the meanings given for example in group 1.

그룹 37Group 37

상기 식에서, R1, R2및 R3는 예를 들어 그룹 1 에서 제시된 의미를 갖는다.Wherein R 1 , R 2 and R 3 have the meanings given for example in group 1.

그룹 38Group 38

상기 식에서, R1, R2및 R3는 예를 들어 그룹 1에서 제시된 의미를 갖는다.Wherein R 1 , R 2 and R 3 have the meanings given for example in group 1.

그룹 39Group 39

상기 식에서, R1, R2및 R3는 예를 들어 그룹 1 에서 제시된 의미를 갖는다.Wherein R 1 , R 2 and R 3 have the meanings given for example in group 1.

그룹 40Group 40

상기 식에서, R1, R2및 R3는 예를 들어 그룹 1 에서 제시된 의미를 갖는다.Wherein R 1 , R 2 and R 3 have the meanings given for example in group 1.

그룹 41Group 41

상기 식에서 R1, R2및 R3는 예를 들어 그룹 1 에서 제시된 의미를 갖는다.Wherein R 1 , R 2 and R 3 have the meanings given for example in group 1.

그룹 42Group 42

상기 식에서, R1, R2및 R3는 예를 들어 그룹 1 에서 제시된 의미를 갖는다.Wherein R 1 , R 2 and R 3 have the meanings given for example in group 1.

그룹 43Group 43

상기 식에서, R1, R2및 R3는 예를 들어 그룹 1 에서 제시된 의미를 갖는다.Wherein R 1 , R 2 and R 3 have the meanings given for example in group 1.

그룹 44Group 44

상기 식에서, R1, R2및 R3는 예를 들어 그룹 1 에서 제시된 의미를 갖는다.Wherein R 1 , R 2 and R 3 have the meanings given for example in group 1.

그룹 45Group 45

상기 식에서, R1, R2및 R3는 예를 들어 그룹 1 에서 제시된 의미를 갖는다.Wherein R 1 , R 2 and R 3 have the meanings given for example in group 1.

그룹 46Group 46

상기 식에서, R1, R2및 R3는 예를 들어 그룹 1 에서 제시된 의미를 갖는다.Wherein R 1 , R 2 and R 3 have the meanings given for example in group 1.

그룹 47Group 47

상기 식에서, R1, R2및 R3는 예를 들어 그룹 1 에서 제시된 의미를 갖는다.Wherein R 1 , R 2 and R 3 have the meanings given for example in group 1.

그룹 48Group 48

상기 식에서, R1, R2및 R3는 예를 들어 그룹 1 에서 제시된 의미를 갖는다.Wherein R 1 , R 2 and R 3 have the meanings given for example in group 1.

그룹 49Group 49

상기 식에서, R1, R2및 R3는 예를 들어 그룹 1 에서 제시된 의미를 갖는다.Wherein R 1 , R 2 and R 3 have the meanings given for example in group 1.

그룹 50Group 50

상기 식에서, R1, R2및 R3는 예를 들어 그룹 1 에서 제시된 의미를 갖는다.Wherein R 1 , R 2 and R 3 have the meanings given for example in group 1.

그룹 51Group 51

상기 식에서, R1, R2및 R3는 예를 들어 그룹 1 에서 제시된 의미를 갖는다.Wherein R 1 , R 2 and R 3 have the meanings given for example in group 1.

그룹 52Group 52

상기 식에서, R1, R2및 R3는 예를 들어 그룹 1 에서 제시된 의미를 갖는다.Wherein R 1 , R 2 and R 3 have the meanings given for example in group 1.

그룹 53Group 53

상기 식에서, R1, R2및 R3는 예를 들어 그룹 1 에서 제시된 의미를 갖는다.Wherein R 1 , R 2 and R 3 have the meanings given for example in group 1.

그룹 54Group 54

상기 식에서, R1, R2및 R3는 예를 들어 그룹 1 애서 제시된 의미를 갖는다.Wherein R 1 , R 2 and R 3 have the meanings given for example in group 1.

그룹 55Group 55

상기 식에서, R1, R2및 R3는 예를 들어 그룹 1 에서 제시된 의미를 갖는다.Wherein R 1 , R 2 and R 3 have the meanings given for example in group 1.

그룹 56Group 56

상기 식에서, R1, R2및 R3는 예를 들어 그룹 1 애서 제시된 의미를 갖는다.Wherein R 1 , R 2 and R 3 have the meanings given for example in group 1.

그룹 57Group 57

상기 식에서, R1, R2및 R3는 예를 들어 그룹 1 에서 제시된 의미를 갖는다.Wherein R 1 , R 2 and R 3 have the meanings given for example in group 1.

그룹 58Group 58

상기 식에서, R1, R2및 R3는 예를 들어 그름 1 에서 제시된 의미를 갖는다.In the above formula, R 1 , R 2 and R 3 have the meanings given for example in 1.

그룹 59Group 59

상기 식에서, R1, R2및 R3는 예를 들어 그룹 1 에서 제시된 의미를 갖는다.Wherein R 1 , R 2 and R 3 have the meanings given for example in group 1.

그룹 60Group 60

상기 식에서, R1, R2및 R3는 예를 들어 그룹 1 에서 제시된 의미를 갖는다.Wherein R 1 , R 2 and R 3 have the meanings given for example in group 1.

그룹 61Group 61

상기 식에서, R1, R2및 R3는 예를 들어 그룹 1 에서 제시된 의미를 갖는다.Wherein R 1 , R 2 and R 3 have the meanings given for example in group 1.

그룹 62Group 62

상기 식에서, R1, R2및 R3는 예를 들어 그룹 1 에서 제시된 의미를 갖는다.Wherein R 1 , R 2 and R 3 have the meanings given for example in group 1.

그룹 63Group 63

상기 식에서, R1, R2및 R3는 예를 들어 그룹 1 에서 제시된 의미를 갖는다.Wherein R 1 , R 2 and R 3 have the meanings given for example in group 1.

그룹 64Group 64

상기 식에서, R1, R2및 R3는 예를 들어 그룹 1 에서 제시된 의미를 갖는다.Wherein R 1 , R 2 and R 3 have the meanings given for example in group 1.

그룹 65Group 65

상기 식에서, R1, R2및 R3는 예를 들어 그룹 1 에서 제시된 의미를 갖는다.Wherein R 1 , R 2 and R 3 have the meanings given for example in group 1.

그룹 66Group 66

상기 식에서, R1, R2및 R3는 예를 들어 그룹 1 에서 제시된 의미를 갖는다.Wherein R 1 , R 2 and R 3 have the meanings given for example in group 1.

그룹 67Group 67

상기 식에서, R1, R2및 R3는 예를 들어 그룹 1 에서 제시된 의미를 갖는다.Wherein R 1 , R 2 and R 3 have the meanings given for example in group 1.

그룹 68Group 68

상기 식에서, R1, R2및 R3는 예를 들어 그룹 1 에서 제시된 의미를 갖는다.Wherein R 1 , R 2 and R 3 have the meanings given for example in group 1.

그룹 69Group 69

상기 식에서, R1, R2및 R3는 예를 들어 그룹 1 에서 제시된 의미를 갖는다.Wherein R 1 , R 2 and R 3 have the meanings given for example in group 1.

그룹 70Group 70

상기 식에서, R1, R2및 R3는 예를 들어 그룹 1 에서 제시된 의미를 갖는다.Wherein R 1 , R 2 and R 3 have the meanings given for example in group 1.

그룹 71Group 71

상기 식에서, R1, R2및 R3는 예를 들어 그룹 1 에서 제시된 의미를 갖는다.Wherein R 1 , R 2 and R 3 have the meanings given for example in group 1.

그룹 72Group 72

상기 식에서, R1, R2및 R3는 예를 들어 그룹 1 에서 제시된 의미를 갖는다.Wherein R 1 , R 2 and R 3 have the meanings given for example in group 1.

그룹 73Group 73

상기 식에서, R1, R2및 R3는 예를 들어 그룹 1 에서 제시된 의미를 갖는다.Wherein R 1 , R 2 and R 3 have the meanings given for example in group 1.

그룹 74Group 74

상기 식에서, R1, R2및 R3는 예를 들어 그룹 1 에서 제시된 의미를 갖는다.Wherein R 1 , R 2 and R 3 have the meanings given for example in group 1.

그룹 75Group 75

상기 식에서, R1, R2및 R3는 예를 들어 그룹 1 에서 제시된 의미를 갖는다.Wherein R 1 , R 2 and R 3 have the meanings given for example in group 1.

그룹 76Group 76

상기 식에서, R1, R2및 R3는 예를 들어 그룹 1 에서 제시된 의미를 갖는다.Wherein R 1 , R 2 and R 3 have the meanings given for example in group 1.

그룹 77Group 77

상기 식에서, R1, R2및 R3는 예를 들어 그룹 1 에서 제시된 의미를 갖는다.Wherein R 1 , R 2 and R 3 have the meanings given for example in group 1.

그룹 78Group 78

상기 식에서, R1, R2및 R3는 예를 들어 그룹 1 에서 제시된 의미를 갖는다.Wherein R 1 , R 2 and R 3 have the meanings given for example in group 1.

그룹 79Group 79

상기 식에서, R1, R2및 R3는 예를 들어 그룹 1 에서 제시된 의미를 갖는다.Wherein R 1 , R 2 and R 3 have the meanings given for example in group 1.

그룹 80Group 80

상기 식에서, R1, R2및 R3는 예를 들어 그룹 1 에서 제시된 의미를 갖는다.Wherein R 1 , R 2 and R 3 have the meanings given for example in group 1.

그룹 81Group 81

상기 식에서, R1, R2및 R3는 예를 들어 그룹 1 에서 제시된 의미를 갖는다.Wherein R 1 , R 2 and R 3 have the meanings given for example in group 1.

그룹 82Group 82

상기 식에서, R1, R2및 R3는 예를 들어 그룹 1 에서 제시된 의미를 갖는다.Wherein R 1 , R 2 and R 3 have the meanings given for example in group 1.

그룹 83Group 83

상기 식에서, R1, R2및 R3는 예를 들어 그룹 1 에서 제시된 의미를 갖는다.Wherein R 1 , R 2 and R 3 have the meanings given for example in group 1.

그룹 84Group 84

상기 식에서, R1, R2및 R3는 예를 들어 그룹 1 에서 제시된 의미를 갖는다.Wherein R 1 , R 2 and R 3 have the meanings given for example in group 1.

그룹 85Group 85

상기 식에서, R1, R4및 R5는 하기 의미를 갖는다 :Wherein R 1 , R 4 and R 5 have the following meanings:

그룹 86Group 86

상기 식에서, R1, R4및 R5는 예를 들어 그룹 85 에서 제시된 의미를 갖는다.Wherein R 1 , R 4 and R 5 have the meanings given for example in group 85.

그룹 87Group 87

상기 식에서, R1, R4및 R5는 예를 들어 그룹 85 에서 제시된 의미를 갖는다.Wherein R 1 , R 4 and R 5 have the meanings given for example in group 85.

그룹 88Group 88

상기 식에서, R1, R4및 R5는 예를 들어 그룹 85 에서 제시된 의미를 갖는다.Wherein R 1 , R 4 and R 5 have the meanings given for example in group 85.

그룹 89Group 89

상기 식에서, R1, R4및 R5는 예를 들어 그룹 85 에서 제시된 의미를 갖는다.Wherein R 1 , R 4 and R 5 have the meanings given for example in group 85.

예를들어, 2-(2-플루오로-4-시아노-5-메톡시-페닐)-4-메틸-5-디플루오로메틸-2,4-디하이드로-3H-1,2,4-트리아졸-3-온 및 황화수소가 출발 물질로서 사용될 경우, 본 발명에 따르는 방법의 반응 과정은 다음 식으로 나타낼 수 있다.For example, 2- (2-fluoro-4-cyano-5-methoxy-phenyl) -4-methyl-5-difluoromethyl-2,4-dihydro-3H-1,2,4 When -triazol-3-one and hydrogen sulfide are used as starting materials, the reaction process of the process according to the invention can be represented by the following formula.

일반식(I) 의 화합물을 제조하기 인한 본 발명에 따르는 방법에서 출발물질로서 사용되는 치환된 방향족 니트릴의 일반적인 정의는 일반식(II) 로 제시된다. 이 일반식 (II)에서, R1, R2, R3및 Z 는 바람직하게는 또는 특히는 R1, R2, R3및 Z에 대하여 바람직하거나 또는 특히 바람직한 것으로서 상기에서 정의한 의미를 갖는다.The general definition of the substituted aromatic nitrile used as starting material in the process according to the invention for the preparation of compounds of general formula (I) is given by general formula (II). In this general formula (II), R 1 , R 2 , R 3 and Z preferably have the meanings defined above as preferred or particularly preferred or particularly preferred for R 1 , R 2 , R 3 and Z.

일반식 (II)의 출발물질은 공지되어 있고/있거나, 공지되어 있는 방법에 의하여 제조할 수 있다(참조: EP-A 370332; DE-A 4238125; DE-A 4303376; US-P 5084084; 제조 실시예).Starting materials of formula (II) are known and / or can be prepared by known methods (see EP-A 370332; DE-A 4238125; DE-A 4303376; US-P 5084084; Yes).

본 발명에 따른 방법을 수행하는데 적합한 희석제는 통상적인 유기 용매이다. 이들은 특히는 예를 들어 벤진, 벤젠, 톨루엔, 크실렌, 클로로벤젠, 디클로로벤젠, 석유 에테르, 헥산, 사이클로헥산, 디클로로메탄, 클로로포름 또는 사염화탄소와 같은 임의로 할로겐화된 지방족, 지환식 또는 방향족 탄화수소; 디에틸 에테르, 이소프로필 에테르, 디옥산, 테트라하이드로푸란 또는 에틸렌 글리콜 디메틸 또는 디에틸 에테르와 같은 에테르; 아세톤, 부타논 또는 메틸 이소부틸 케톤과 같은 케톤; 아세토니트릴, 프로피오니트릴 또는 벤조니트릴과 같은 니트릴; N,N-디메틸포름아미드, N,N-디에틸아세트아미드, N-메틸포름아닐라이드, N-메틸피롤리돈 또는 헥사메틸인산 트리아미드와 같은 아미드; 메틸아세이트 또는 에틸아세테이트와 같은 에스테르; 디메틸설폭사이드와 같은 설폭사이드; 피리딘과 같은 아진; 메탄올, 에탄올, n- 또는 i-프로판올, 에틸렌 글리콜 모노메틸 에테르, 에틸렌 글리콜 모노에틸 에테르, 디에틸렌 글리콜 모노메틸 에테르 또는 디에틸렌 모노에틸 글리콜 에테르와 같은 알콜; 이들과 물과의 혼합물, 또는 순수한 물이 포함된다.Suitable diluents for carrying out the process according to the invention are conventional organic solvents. These are, in particular, optionally halogenated aliphatic, alicyclic or aromatic hydrocarbons such as, for example, benzine, benzene, toluene, xylene, chlorobenzene, dichlorobenzene, petroleum ether, hexane, cyclohexane, dichloromethane, chloroform or carbon tetrachloride; Ethers such as diethyl ether, isopropyl ether, dioxane, tetrahydrofuran or ethylene glycol dimethyl or diethyl ether; Ketones such as acetone, butanone or methyl isobutyl ketone; Nitriles such as acetonitrile, propionitrile or benzonitrile; Amides such as N, N-dimethylformamide, N, N-diethylacetamide, N-methylformanilide, N-methylpyrrolidone or hexamethyl phosphate triamide; Esters such as methyl acetate or ethyl acetate; Sulfoxides such as dimethyl sulfoxide; Azines such as pyridine; Alcohols such as methanol, ethanol, n- or i-propanol, ethylene glycol monomethyl ether, ethylene glycol monoethyl ether, diethylene glycol monomethyl ether or diethylene monoethyl glycol ether; Mixtures of these with water, or pure water.

본 발명에 따른 방법은 바람직하게는 적합한 반응 보조제의 존재하에 수행된다. 적합한 반응 보조제는 모든 통상적인 무기 또는 유기 염기이다. 이들로는 알칼리 금속 또는 알칼리 토금속 수소화물, 수산화물, 아미드, 알콜레이트, 아세테이트, 탄산염 또는 중탄산염, 예를 들어 수소화나트륨, 나트륨 아미드, 나트륨 메틸레이트, 나트륨 에틸레이트, 칼륨 t-부틸레이트, 수산화나트륨, 수산화칼륨, 수산화암모늄, 나트륨 아세테이트, 칼륨 아세테이트, 칼슘 아세테이트, 암모늄 아세테이트, 탄산나트륨, 탄산칼륨, 중탄산칼륨, 중탄산나트륨 또는 탄산암모늄 및 또한 트리메틸아민, 트리에틸아민, 트리부틸아민, N,N-디메틸아닐린, 피리딘, N-메틸피페리딘, N,N-디메틸아미노피리딘, 디아자비사이클로옥탄(DABCO), 디아자비사이클로노넨(DBN) 또는 디아자비사이클로운데센(DBU)과 같은 염기성 유기 질소 화합물이 포함된다.The process according to the invention is preferably carried out in the presence of a suitable reaction aid. Suitable reaction aids are all customary inorganic or organic bases. These include alkali or alkaline earth metal hydrides, hydroxides, amides, alcoholates, acetates, carbonates or bicarbonates such as sodium hydride, sodium amide, sodium methylate, sodium ethylate, potassium t-butylate, sodium hydroxide, Potassium hydroxide, ammonium hydroxide, sodium acetate, potassium acetate, calcium acetate, ammonium acetate, sodium carbonate, potassium carbonate, potassium bicarbonate, sodium bicarbonate or ammonium carbonate and also trimethylamine, triethylamine, tributylamine, N, N-dimethylaniline , Basic organic nitrogen compounds such as pyridine, N-methylpiperidine, N, N-dimethylaminopyridine, diazabicyclooctane (DABCO), diazabicyclononene (DBN) or diazabicycloundecene (DBU) do.

반응 온도는 비교적 넓은 범위내에서 변할 수 있다. 반응은 일반적으로 0 내지 약 100 ℃,바람직하게는 10 내지 약 80 ℃ 의 온도에서 수행한다.The reaction temperature can vary within a relatively wide range. The reaction is generally carried out at a temperature of 0 to about 100 ° C, preferably 10 to about 80 ° C.

본 발명에 따른 방법은 일반적으로 대기압하에서 수행한다. 그러나, 반응을 승압 또는 감압, 일반적으로 0.1 내지 10 바에서 수행하는 것이 또한 가능하다.The process according to the invention is generally carried out at atmospheric pressure. However, it is also possible to carry out the reaction at elevated or reduced pressure, generally from 0.1 to 10 bar.

본 발명에 따른 방법을 수행하는 경우, 일반식 (II) 의 출발 물질을 일반적으로 적합판 희석제중, 반응 보조제의 존재하에서 도입하고, 황화수소 또는 티오아세트아미드를 천천히 계량하여 첨가한다. 황화수소 또는 티오아세트아미드는 바람직하게는 상대적으로 과량으로 사용된다. 반응 혼합물을 필요한 특정 온도에서 수시간동안 교반한다. 본 발명에서 따른 방법에서 후처리는 각 경우에 통상적인 방법에 따라 수행된다(제조 실시예 참조).When carrying out the process according to the invention, starting materials of the general formula (II) are generally introduced in the presence of a reaction aid in a suitable plate diluent, and hydrogen sulfide or thioacetamide is slowly added by metering. Hydrogen sulfide or thioacetamide is preferably used in relatively excess. The reaction mixture is stirred for several hours at the specific temperature required. The post-treatment in the process according to the invention is carried out according to the usual method in each case (see preparation examples).

본 발명에 따른 활성 화합물들은 낙엽제, 건조제, 줄기-킬러 및, 특히 잡초제거제로서 사용될 수 있다. "잡초"란 용어는 넓은 의미로는, 원치 않는 장소에 자라는 모든 식물들을 의미한다. 본 발명의 물질이 총체적인 제초제로서 작용하는지 또는 선택적인 제초제로서 작용하는지의 여부는 기본적으로 적용 비율에 따라 좌우된다.The active compounds according to the invention can be used as deciduous, desiccant, stem-killer and, in particular, weed removers. The term "weeds" broadly means all plants that grow in unwanted places. Whether the substance of the invention acts as a total herbicide or as a selective herbicide depends essentially on the application rate.

본 발명에 따른 활성 화합물을 예를 들어 하기의 식물에 사용할 수 있다;The active compounds according to the invention can be used, for example, in the following plants;

하기 속의 쌍자엽 잡초들: 시나피스(Sinapis), 레피듐(Lepidium), 갈륨(Galium), 스텔라리아(Stellaria), 마트리카리아(Matricaria), 안테미스(Anthemis), 갈린소가(Galinsoga), 케노포듐(Chenopodium), 우르티카(Urtica), 세네시오(Senecio), 아마란투스(Amaranthus), 포르톨라카(Portulaca), 크산튬(Xanthium), 콘볼부루스(Convolvulus), 이포모에아(Ipomoea), 폴리고눔(Polygonum), 세스바니아(Sesbania), 암브로시아(Ambrosia), 시르슘(Cirsium), 카르두스(Carduus), 손쿠스(Sonchus), 솔라눔(Solanum), 로리파(Rorippa), 로탈라(Rotala), 린데르니아(Lindernia), 라미움(Lamium), 베로니카(Vcronica), 아부틸론(Abutilon), 에멕스(Emex), 다투라(Datura), 비올라(Viola), 갈레옵시스(Galeopsis), 파파베르(Papaver), 센타우레아(Centaurea), 트리폴리움(Trifolium), 라눈쿨루스(Ranunculus) 및 타락사쿰(Taraxacum).Dicotyledonous weeds in the following genus : Sinapis, Lepidium, Gallium, Stellaria, Matricaria, Anthemis, Galinsoga, Ke Norpodium, Urtica, Senesio, Amaranthus, Portulaca, Xanthium, Convolvulus, Ipomoea, Polygonum, Sesbania, Ambrosia, Cirsium, Carduus, Sonchus, Solanum, Rorippa, Rotala ), Lindernia, Lamium, Vcronica, Abutilon, Emex, Datura, Viola, Galeopsis, Papaver, Centaurea, Trifolium, Ranunculus and Taraxacum.

하기 속의 쌍자엽 작물들: 고시피움(Gossypium), 글리시네(Glycine), 베타(Beta), 다우크스(Daucus), 파세올루스(Phaseolus), 피숨(Pisum), 솔라눔(Solanum), 리눔(Linum), 이포모에아(Ipomoca), 비시아(Vicia),니코티아나(Nicotiana), 리로퍼시콘(Lycopersicon), 아라키스(Arachis), 브라시카(Brassica), 락투카(Lactuca), 쿠쿠미스(Cucumis) 및 쿠쿠르비타(Cucurbita). Dicotyledonous crops of the following genus : Gossypium, Glycine, Beta, Dauscus, Phaseolus, Pisum, Solanum, Linum ), Ipomoca, Vicia, Nicotiana, Lycopersicon, Arachis, Brassica, Lactuca, Cucumis ) And Cucurbita.

하기 속의 단자엽 잡초들:에키노글로아(Echinochloa), 세타리아(Setaria), 파니쿰(Panicum), 디기타리아(Digitaria), 플레움(Phleum), 포아(Poa), 페스투카(Festuca), 엘레우신(Eleusin), 브라키아리아(Brachiaria), 롤리움(Lolium), 브로무스(Bromus), 아베나(Avena), 시페루스(Cyperus), 소르굼(Sorghum), 아그로피론(Agropyron), 시노돈(Cynodon), 모노로리아(Monochoria), 핌브리스틸리스(Fimbristylis), 사기타리아(Sagittaria), 엘레오카리스(Eleocharis), 쉬르푸스(Scirpus), 파스팔룸(Paspalum), 이스카에뭄(Ischaemum), 스페노클레아(Sphenoclea), 닥틸로크테니움(Dactyloctenium), 아그로스티스(Agrostis), 알로페쿠루스(Alopecurus) 및 아페라(Apera).Monocot weeds in the following genus: Echinochloa, Setaria, Panicum, Digitaria, Phleum, Poa, Festusca, Ele Eleusin, Brachiaria, Lolium, Bromus, Avena, Cyperus, Sorghum, Agropyron, and Sinodon (Cynodon, Monochoria, Fimbristylis, Sagittaria, Eleocharis, Scirpus, Paspalum, Iscamum) , Sphenoclea, Dactyloctenium, Agrostis, Alopecurus and Apera.

하기 속의 단자엽 작물들:오리자(Oryza), 제아(Zea), 트리티쿰(Triticum), 호르데움(Hordeum), 아베나(Avena), 세칼레(Secale), 소르굼(Sorghum), 파니쿰(Panicum), 사카룸(Saccharum), 아나나스(Ananas), 아스파라구스(Asparagus) 및 알리움(Allium). Monocot crops of the following genus: Oryza, Zea, Triticum, Hordeum, Avena, Secale, Sorghum, Panicum Panicum), Saccharum, Ananas, Asparagus and Allium.

그러나, 본 발명에 따른 활성 화합물의 용도는 상기 속에 전혀 제한되지 않고, 동일한 방식으로 다른 식물들에까지도 확장된다.However, the use of the active compounds according to the invention is not limited at all in the above and extends to other plants in the same way.

추가로, 본 발명의 화합물은, 농도에 따라, 예를 들어 산업 지역 및 철로위에, 그리고 나무가 심어져 있거나 심어져 있지 않은 보도 및 광장위에 있는 잡초들의 전체적인 구제에 적당하다. 마찬가지로, 본 발명의 화합물을 예를 들면 조립지, 관상수 재배장, 과수원, 포도원, 감귤밭, 견과류 과수원, 바나나 농장, 커피 농장, 차 농장, 고무 농장, 야자 농장, 코코아 농장, 연한 과일 식림지, 홉밭, 잔디, 경마장 및 목장에 자라는 다년생 작물중의 잡초를 구제하기 위해, 그리고 일년생 작물중의 잡초를 선택적으로 구제하기 위해 사용할 수 있다.In addition, the compounds of the present invention are suitable for the overall control of weeds, depending on concentration, for example on industrial areas and railway lines, and on sidewalks and plazas with or without trees. Similarly, the compounds of the present invention include, for example, granulated paper, ornamental water plantations, orchards, vineyards, citrus fields, nut orchards, banana plantations, coffee plantations, tea plantations, rubber plantations, palm plantations, cocoa plantations, soft fruit plantations, It can be used to control weeds in perennial crops growing on hop fields, grasses, race tracks and ranches, and to selectively control weeds in annual crops.

본 발명에 따른 일반식 (I) 의 화합물은 특히 단자엽 및 쌍자엽 작물에서 발아전 및 발아후 방법에 의해 단자엽 및 쌍자엽 잡초를 선택적으로 구제하는데 특히 적합하다.The compounds of general formula (I) according to the invention are particularly suitable for the selective control of monocotyledonous and dicotyledonous weeds by pre- and post-germination methods, in particular in monocotyledonous and dicotyledonous crops.

특정의 정도까지, 일반식 (I) 의 화합물은 또한 예를 들어 벼에서 피리쿨라리아 오리아에 대해 살진균 활성을 나타낸다.To a certain degree, the compounds of general formula (I) also exhibit fungicidal activity against pyricularia aria, for example in rice.

활성 화합물은 용액제, 유제, 수화성 분제, 현탁액, 분제, 연무제, 페이스트, 가용성 분제, 과립제, 현탁액-유제 농축액, 활성 화합물로 함침된 천연 및 합성 물질, 및 중합체 물질중의 미소 캡슐과 같은 통상적인 제제로 전환시킬 수 있다.The active compounds are such as solutions, emulsions, hydrating powders, suspensions, powders, mists, pastes, soluble powders, granules, suspension-emulsion concentrates, natural and synthetic materials impregnated with the active compounds, and microcapsules in polymeric materials. It may be converted to a conventional formulation.

이들 제제는 공지된 방법으로, 예를 들어, 임의로 계면활성제, 즉 유화제 및/또는 분산제 및/또는 포움-형성제를 사용하여 활성 화합물을 증량제, 즉 액체 용매 및/또는 고형 담체와 혼합함으로써 제조한다.These formulations are prepared by known methods, for example by mixing the active compounds with extenders, ie liquid solvents and / or solid carriers, optionally using surfactants, ie emulsifiers and / or dispersants and / or foam-forming agents. .

물을 증량제로서 사용하는 경우에는, 예를 들어 유기용매를 또한 보조 용매로 사용할 수 있다. 액체 용매로서는, 주로 크실렌, 톨루엔 또는 알킬나프탈렌과같은 방향족 화합물, 클로로벤젠, 클로로에틸렌 또는 메틸렌 클로라이드와 같은 염소화 방향족 및 염소화 지방족 탄화수소, 사이클로헥산 또는 파라핀, 예를들어, 석유 분획물, 광유 및 식물유와 같은 지방족 탄화수소, 부탄올 또는 글리콜과 같은 알콜 및 이들의 에테르 및 에스테르, 아세톤, 메틸 에틸 케톤, 메틸 이소부틸 케톤 또는 사이클로헥사논과 같은 케톤, 디메틸포름아미드 및 디메틸설폭사이드와 같은 강한 극성 용매 뿐만 아니라 물이 적당하다.When water is used as the extender, for example an organic solvent can also be used as an auxiliary solvent. Liquid solvents are mainly aromatic compounds such as xylene, toluene or alkylnaphthalene, chlorinated aromatic and chlorinated aliphatic hydrocarbons such as chlorobenzene, chloroethylene or methylene chloride, cyclohexane or paraffins, for example petroleum fractions, mineral oils and vegetable oils. Alcohols such as aliphatic hydrocarbons, butanol or glycol and ethers and esters thereof, as well as strong polar solvents such as ketones such as acetone, methyl ethyl ketone, methyl isobutyl ketone or cyclohexanone, dimethylformamide and dimethyl sulfoxide, are suitable Do.

고형 담체로는 예를들어 암모늄염 및 카올린, 점토, 활석, 쵸크, 석영, 아타풀가이트, 몬모릴로나이트 또는 규조토와 같은 천연 암석 가루, 및 고분산 실리카, 산화 알루미늄 및 실리케이트와 같은 합성 암석 가루가 적당하다. 과립제용 고형 담체로는 예를 들어 방해석, 대리석, 경석, 해포석 및 백운석과 같은 분쇄 및 분류된 천연 암석, 및 무기 및 유기 가루의 합성 과립, 및 톱밥, 코코넛 껍질, 옥수수 속대 및 담배줄기와 같은 유기물질의 과립이 적당하다. 유화제 및/또는 포움-형성제로는 예를 들어 비이온성 및 음이온성 유화제, 예를 들어 폴리옥시에틸렌 지방산 에스테르, 알킬아릴 폴리글리콜 에테르와 같은 폴리옥시에틸렌 지방 알콜 에테르 알킬설포네이트, 알킬 설페이트, 아릴 설포네이트 및 단백질 가수분해 생성물이 적당하다. 분산제로는 예를들어 리그닌-설파이트 폐액 및 메틸셀룰로오즈가 적당하다.Solid carriers are suitable, for example, ammonium salts and natural rock powders such as kaolin, clay, talc, chalk, quartz, attapulgite, montmorillonite or diatomaceous earth, and synthetic rock powders such as highly dispersed silica, aluminum oxide and silicate. Solid carriers for granulation include, for example, pulverized and classified natural rocks such as calcite, marble, pumice, calcite and dolomite, and synthetic granules of inorganic and organic powders, and organic such as sawdust, coconut husk, corncobs and tobacco stems. Granules of material are suitable. Emulsifiers and / or foam-forming agents include, for example, nonionic and anionic emulsifiers, for example polyoxyethylene fatty alcohol ether alkylsulfonates such as polyoxyethylene fatty acid esters, alkylaryl polyglycol ethers, alkyl sulfates, aryl sulfo Nate and proteolytic products are suitable. Suitable dispersants are, for example, lignin-sulfite waste liquors and methylcellulose.

접착제, 예를 들어 카복시메틸셀룰로오즈, 및 아라비아고무, 폴리비닐 알콜, 폴리비닐 아세테이트와 같은 분말, 과립 또는 유액 형태의 천연 및 합성 중합체, 및 세팔린 및 레시틴과 같은 천연 인지질, 및 합성 인지질이 제제에 사용될 수 있다. 그외의 다른 첨가제로는 광유 및 식물유가 사용될 수 있다.Adhesives such as carboxymethylcellulose, and natural and synthetic polymers in the form of powders, granules or emulsions, such as gum arabic, polyvinyl alcohol, polyvinyl acetate, and natural phospholipids such as cephalin and lecithin, and synthetic phospholipids Can be used. As other additives, mineral oil and vegetable oil may be used.

산화철, 산화티탄 및 프루시안 블루 등의 무기안료, 및 알리자린 염료, 아조 염료 및 금속 프탈로시아닌 염료 등의 유기염료와 같은 착색제 및 철, 망간, 붕소, 구리, 코발트, 몰리브덴 및 아연의 염과 같은 미량 영양소를 사용할 수도 있다.Inorganic pigments such as iron oxide, titanium oxide and prussian blue, and colorants such as alizarin dyes, azo dyes and organic dyes such as metal phthalocyanine dyes and micronutrients such as salts of iron, manganese, boron, copper, cobalt, molybdenum and zinc You can also use

제제는 일반적으로 0.1 내지 95 중량%, 바람직하개는 0.5 내지 90 중량%의 활성 화합물을 함유한다.The formulations generally contain 0.1 to 95% by weight, preferably 0.5 to 90% by weight of active compound.

잡초를 방제하기 위하여, 본 발명의 활성 화합물은 그 자체로 또는 그들키고, 내부온도는 33 ℃ 로 상승된다. 반응을 1 시간후에 완결한다. 용액을 회전 증발기상에서 농축시키고, 잔류물을 이소프로판올로 부터 개결정화시킨다.In order to control the weeds, the active compounds of the present invention by themselves or them, the internal temperature is raised to 33 ℃. The reaction is complete after 1 hour. The solution is concentrated on a rotary evaporator and the residue is crystallized from isopropanol.

융점 161 ℃ 인 2-(2-플루오로-4-티오카바모일-5-아미노-페닐)-4-에틸-5-트리플루오로메틸-2,4-디하이드로-3H-1,2,4-트리아졸-3-온 2.9 g(이론치의 42%) 을 수득한다.2- (2-fluoro-4-thiocarbamoyl-5-amino-phenyl) -4-ethyl-5-trifluoromethyl-2,4-dihydro-3H-1,2,4 having a melting point of 161 ° C 2.9 g (42% of theory) of -triazol-3-one are obtained.

실시예 3Example 3

11 g(0.0276 mol)의 2-(2-플루오로-4-시아노-5-에틸설포닐아미노페닐)-4-메틸-5-디플루오로메틸-2,4-디하이드로-3H-1,2,4-트리아졸-3-티온을 100 ㎖의 피리딘중에서 황화수소를 통과시키면서 70 ℃에서 4.5 시간동안 교반한다. 용액을 회전 증발기상에서 농축시키고, 잔류물을 물에서 교반하고, 혼합물을 농염산으로 산성화시킨 후, 침전 생성물을 여과하고, 물로 세척하여 이소프로판올로 부터 개결정화시킨다.11 g (0.0276 mol) of 2- (2-fluoro-4-cyano-5-ethylsulfonylaminophenyl) -4-methyl-5-difluoromethyl-2,4-dihydro-3H-1 The, 2,4-triazole-3-thione is stirred at 70 ° C. for 4.5 hours while passing hydrogen sulfide in 100 ml of pyridine. The solution is concentrated on a rotary evaporator, the residue is stirred in water, the mixture is acidified with concentrated hydrochloric acid, the precipitated product is filtered off and washed with water to crystallize from isopropanol.

융점 183 ℃ 인 2-(2-플루오로-4-티오카바모일-5-에틸설포닐아미노페닐)-4-메틸-5-디플루오로메틸-2,4-디하이드로-3H-1,2,4-트리아졸-3-티온 9 g(이론치의 77%) 을 수득한다.Melting point 183 ° C. Phosphorus 2- (2-fluoro-4-thiocarbamoyl-5-ethylsulfonylaminophenyl) -4-methyl-5-difluoromethyl-2,4-dihydro-3H-1,2 9 g (77% of theory) of, 4-triazole-3-thione are obtained.

제조 실시예 1, 2 및 3 과 유사하게, 그리고, 본 발명에 따른 제조방법의 일반적인 설명에 따라, 예를 들어 하기 표 1 에 기재된 일반식 (I) 을 화합물을 제조할 수 있다 :Similarly to Preparation Examples 1, 2 and 3 and according to the general description of the preparation process according to the invention, for example, the compounds of formula (I) described in Table 1 below can be prepared:

표 1 : 일반식 (I) 의 화합물의 예Table 1: Examples of Compounds of General Formula (I)

출발 화합물의 제조Preparation of Starting Compound

실시예 II-1 :Example II-1:

5.8g(0.042 mol) 의 탄산칼륨을 실온에서 150 ㎖ 중의 디메틸 설폭사이드중의 5.4g(0.034 mol) 의 2,4,5-트리플루오로벤조니트릴(참조예: EP 191181) 및 6.3g(0.034 mol) 의 4-메틸-3-트리플루오로메틸-1,2,4-트리아졸린-5-온(참조예: US 3,785,052) 에 가하고, 계속해서 혼합물을 100 ℃ 에서 14 시간동안 가열한다. 후처리를 위해, 냉각 반응 혼합물을 물에 가하고, 묽은 염산으로 pH 를 2 로 조정한 다음, 디클로로메탄으로 수회 추출한다. 유기상을 합하여 황산나트륨 상에서 건조시키고, 진공중에서 농축시킨다. 잔류물을 실리카겔 상에서 크로마토그래피한다(용리제: 디클로로메탄),5.8 g (0.042 mol) of potassium carbonate was added to 5.4 g (0.034 mol) of 2,4,5-trifluorobenzonitrile (see EP 191181) and 6.3 g (0.034) in dimethyl sulfoxide in 150 ml at room temperature. mol) of 4-methyl-3-trifluoromethyl-1,2,4-triazolin-5-one (see eg US 3,785,052) and then the mixture is heated at 100 ° C. for 14 hours. For workup, the cold reaction mixture is added to water, the pH is adjusted to 2 with dilute hydrochloric acid and then extracted several times with dichloromethane. The combined organic phases are dried over sodium sulphate and concentrated in vacuo. The residue is chromatographed on silica gel (eluent: dichloromethane),

융점 74 ℃ 인 1-(4-시아노-2,5-디플루오로페닐)-4-메틸-3-트리플루오로메틸-1,2,4-트리아졸린-5-온 6.2 g(이론치의 60%) 을 수득한다.6.2 g of 1- (4-cyano-2,5-difluorophenyl) -4-methyl-3-trifluoromethyl-1,2,4-triazolin-5-one having a melting point of 74 deg. 60%) is obtained.

실시예 II-2 :Example II-2

0.83g(0.006 mol) 의 탄산칼륨을 실온에서 50 ㎖ 중의 디메틸 설폭사이드중의 0.48g(0.005 mol) 의 메탄설폰아미드 및 1.52g(0.005 mol) 의 1-(4-시아노-2,5-디플루오로페닐)-4-메틸-3-트리플루오로메틸-1,2,4-트리아졸린-5-온에 가하고, 계속해서 혼합물을 120 ℃ 에서 12 시간동안 가열한다. 후처리를 위해, 냉각 반응 혼합물을 물에 가하고, 묽은 염산으로 pH 를 2 로 조정한 다음, 디클로로메탄으로 수회 추출한다. 유기상을 합하여 황산나트륨 상에서 건조시키고, 진공중에서 농축시킨다. 잔류물을 실리카겔 상에서 크로마토그래피한다(용리제: 디클로로메탄/메탄올 20:1).0.83 g (0.006 mol) of potassium carbonate was added to 0.48 g (0.005 mol) of methanesulfonamide in 50 ml of dimethyl sulfoxide and 1.52 g (0.005 mol) of 1- (4-cyano-2,5- at room temperature. Difluorophenyl) -4-methyl-3-trifluoromethyl-1,2,4-triazolin-5-one is added and the mixture is then heated at 120 ° C. for 12 hours. For workup, the cold reaction mixture is added to water, the pH is adjusted to 2 with dilute hydrochloric acid and then extracted several times with dichloromethane. The combined organic phases are dried over sodium sulphate and concentrated in vacuo. The residue is chromatographed on silica gel (eluent: dichloromethane / methanol 20: 1).

융점 67 ℃ 인 1-(4-시아노-2-플루오로-5-메틸설포닐아미노페닐)-4-메틸-3-트리플루오로메틸-1,2,4-트리아졸린-5-온 0.55 g(이론치의 28%) 을 수득한다.1- (4-cyano-2-fluoro-5-methylsulfonylaminophenyl) -4-methyl-3-trifluoromethyl-1,2,4-triazolin-5-one 0.55 having a melting point of 67 ° C. g (28% of theory) is obtained.

실시예 II-3 :Example II-3:

0.3g(10 mmol) 의 수소화나트륨(80%)을 0 내지 5 ℃ 에서 2 ㎖ 의 톨루엔 및 30 ㎖ 의 디메틸포름아미드중의 1.8g(10 mmol) 의 에틸 3-아미노-4,4,4-트리플루오로크로토네이트의 초기 충전물에 가한다. 혼합물을 0 내지 5 ℃ 에서 30 분동안 교반한다. 혼합물을 -70 ℃ 로 냉각시킨 후, 10 ㎖ 의 톨루엔에 용해시킨 0.9g(5 mmol) 의 4-시아노-2,5-디플루오로-페닐 이소시아네이트를 가하고, 혼합물을 -60 내지 -70 ℃ 에서 150 분동안 교반한다. 냉각 배쓰를 제거한 후, 2 ㎖ 의 아세트산을 가한다. 혼합물을 물로 약 2 배 부피로 희석시키고, 에틸 아세테이트로 추출한다. 유기상을 농축시키고, 잔류물을 디이소프로필 에테르로 결정화시킨다.0.3 g (10 mmol) of sodium hydride (80%) was added 1.8 g (10 mmol) of ethyl 3-amino-4,4,4- in 2 ml of toluene and 30 ml of dimethylformamide at 0-5 ° C. To the initial charge of trifluorocrotonate. The mixture is stirred at 0-5 ° C. for 30 minutes. After the mixture was cooled to -70 ° C, 0.9 g (5 mmol) of 4-cyano-2,5-difluoro-phenyl isocyanate dissolved in 10 ml of toluene was added and the mixture was -60 to -70 ° C. Stir for 150 minutes. After removing the cooling bath, 2 ml of acetic acid is added. The mixture is diluted to about two volumes with water and extracted with ethyl acetate. The organic phase is concentrated and the residue is crystallized with diisopropyl ether.

융점 194 ℃ 인 1-(4-시아노-2,5-디플루오로-페닐)-3,6-디하이드로-2,6-디옥소-4-트리플루오로메틸-1-(2H)-피리디민 1.1 g(이론치의 69%) 을 수득한다.1- (4-cyano-2,5-difluoro-phenyl) -3,6-dihydro-2,6-dioxo-4-trifluoromethyl-1- (2H)-having a melting point of 194 ° C 1.1 g (69% of theory) of pyrididimine are obtained.

실시예 II-4 :Example II-4:

0.83g(3 mmol) 의 1-(4-시아노-2,5-디플루오로페닐)-3,6-디하이드로-2,6-디옥소-3,4-디메틸-1-(2H)-피리디민, 0.32g(3 mmol) 의 메탄설폰아미드, 0.6g 의 탄산칼륨 및 10 ㎖ 의 디메틸 설폭사이드의 혼합물을 120 ℃ 에서 10 시간동안 가열한다. 냉각후, 혼합물을 빙수에 붓고, 2N 염산으로 산성화시킨다. 그후, 에틸아세테이트로 추출하고, 유기상을 물로 세척하고, 황산나트륨으로 건조시킨 다음, 여과한다. 수류 진공하에서 여액으로 부터 용매를 조심스럽게 제거한다.0.83 g (3 mmol) of 1- (4-cyano-2,5-difluorophenyl) -3,6-dihydro-2,6-dioxo-3,4-dimethyl-1- (2H) -A mixture of pyrididimine, 0.32 g (3 mmol) methanesulfonamide, 0.6 g potassium carbonate and 10 ml dimethyl sulfoxide is heated at 120 ° C. for 10 hours. After cooling, the mixture is poured into ice water and acidified with 2N hydrochloric acid. Then extracted with ethyl acetate, the organic phase is washed with water, dried over sodium sulfate and filtered. The solvent is carefully removed from the filtrate under water vacuum.

1-(4-시아노-2-플루오로-5-메틸설포닐아미노페닐)-3,6-디하이드로-2,6-디옥소-3,4-디메틸-1-(2H)-피리디민 0.8 g(이론치의 76%) 을 결정성 잔류물로 수득한다(융점 >250 ℃).1- (4-cyano-2-fluoro-5-methylsulfonylaminophenyl) -3,6-dihydro-2,6-dioxo-3,4-dimethyl-1- (2H) -pyridimine 0.8 g (76% of theory) are obtained as crystalline residue (melting point> 250 ° C.).

사용 실시예Example of use

실시예 AExample A

발아전 시험Germination test

용매 : 아세톤 5 중량부Solvent: 5 parts by weight of acetone

유화제 : 알킬아릴 폴리글리콜 에테르 1 중량부Emulsifier: 1 part by weight of alkylaryl polyglycol ether

활성 화합물 1 중량부를 상기 지정량의 용매와 혼합하고, 상기 지정량의 유화제를 가한 후, 농축물을 목적 농도가 되도록 물로 희석하여 활성 화합물의 적당한 제제를 제조한다.1 part by weight of the active compound is mixed with the specified amount of solvent, the specified amount of emulsifier is added, and the concentrate is diluted with water to the desired concentration to prepare a suitable formulation of the active compound.

시험 식물의 종자를 표준 토양에 파종하고, 24 시간후예 활성 화합물 제제를 관수한다. 단위 면적당 물의 양을 일정하게 유지시키는 것이 편리하다. 제제중의 활성 화합물 농도는 중요하지 않으며, 단위 면적당 활성 화합물의 적용 비율만이 중요하다. 3 주후, 식물의 손상도를 무처리 대조유의 전개와 비교하여 손상%로 평가하였다. 수치는 다음과 같은 의미를 갖는다:Seeds of the test plants are sown in standard soil and after 24 hours, the active compound preparations are irrigated. It is convenient to keep the amount of water per unit area constant. The concentration of active compound in the formulation is not critical, only the rate of application of the active compound per unit area is important. Three weeks later, the degree of damage of the plants was assessed as% damage compared to the development of the untreated control. Numbers have the following meanings:

0% = 효과가 없음(무처리 대조용과 마찬가지)0% = no effect (just like untreated control)

100% = 완전 사멸.100% = complete kill.

표 ATable A

발아전 시험/온실Germination Test / Greenhouse

표 BTABLE B

발아전 시험/온실Germination Test / Greenhouse

실시예 BExample B

발아후 시험Post Germination Test

용매 : 아세톤 5 중량부Solvent: 5 parts by weight of acetone

유화제 : 알킬아릴 폴리글리콜 에테르 1 중량부Emulsifier: 1 part by weight of alkylaryl polyglycol ether

활성 화합물 1 중량부를 상기 지정량의 용매와 혼합하고, 상기 지정량의 유화제를 가한 후, 농축물을 목적 농도가 되도록 물로 희석하여 활성 화합물의 적당한 제제를 제조하였다.1 part by weight of the active compound was mixed with the solvent of the specified amount, the emulsifier of the specified amount was added, and the concentrate was diluted with water to the desired concentration to prepare a suitable formulation of the active compound.

높이 5 내지 15 cm 의 시험 식물에 활성 화합물 제제를 단위 면적당 목적하는 특정양의 화합물이 적용되도록 분무한다. 3 주후, 식물의 손상도를 무처리 대조용의 전개와 비교하여 손상%로 평가하였다. 수치는 다음과 같은 의미를 갖는다:The test compound of 5 to 15 cm in height is sprayed with the active compound preparation to apply the desired amount of compound per unit area. Three weeks later, the degree of damage of the plants was assessed as% damage compared to the development of the untreated control. Numbers have the following meanings:

0% = 효과가 없음(무처리 대조용과 마찬가지)0% = no effect (just like untreated control)

100% = 완전 사멸.100% = complete kill.

표 CTable C

발아후 시험/온실After germination test / greenhouse

Claims (8)

일반식 (I)의 치환된 방향족 티오카복스아미드 :Substituted aromatic thiocarboxamides of general formula (I): 상기 식에서,Where R1은 수소 또는 할로겐을 나타내고,R 1 represents hydrogen or halogen, R2는 그룹 -A1-A2-A3를 나타내며,R 2 represents a group -A 1 -A 2 -A 3 , 여기에서,From here, A1은 단일 결합을 나타내거나, -O- 또는 그룹 -N-A4- (여기에서, A4는 수소 또는 C1-C4-알킬을 나타낸다)을 나타내고,A 1 represents a single bond or -O- or a group -NA 4- (wherein A 4 represents hydrogen or C 1 -C 4 -alkyl), A2는 단일 결합, -SO2- 또는 C1-C6-알칸디일을 나타내며,A 2 represents a single bond, -SO 2 -or C 1 -C 6 -alkanediyl, A3은 하이드록실, 아미노, 할로겐, 또는 2 내지 6 개의 탄소 원자를 가지는 알키닐을 나타내거나, 또는 각 경우에 알킬 그룹에 1 내지 6 개의 탄소 원자를 가지며 임의로 할로겐 또는 C1-C4-알콕시 치환된 알킬 또는 알콕시를 나타내고,A 3 represents hydroxyl, amino, halogen, or alkynyl having 2 to 6 carbon atoms, or in each case has 1 to 6 carbon atoms in the alkyl group and optionally halogen or C 1 -C 4 -alkoxy Substituted alkyl or alkoxy, R3은 수소를 나타내며,R 3 represents hydrogen, Z 는 각 경우에 헤테로사이클릭 환 계에 1 내지 4 개의 질소 원자 및 2 내지 8개의 탄소 원자를 가지며 임의로 -CO- 및/또는 -CS- 중에서 선택된 3 개 이하의 그룹을 함유하고, 할로겐, C1-C6-알킬 (할로겐에 의해 임의로 치환된다), C1-C6-알킬아미노, 디-(C1-C4-알킬)-아미노 및 C3-C6-사이클로알킬로 구성된 그룹중에서 선택된 하나 이상의 그룹에 의해 임의로 치환되는, 각 경우에 모노사이클릭 또는 비사이클릭인 포화 또는 불포화 헤테로사이클릴, 헤테로사이클릭아미노 또는 헤테로사이클릴이미노를 나타낸다.Z in each case has 1 to 4 nitrogen atoms and 2 to 8 carbon atoms in the heterocyclic ring system and optionally contains up to 3 groups selected from -CO- and / or -CS-, halogen, C From the group consisting of 1 -C 6 -alkyl (optionally substituted by halogen), C 1 -C 6 -alkylamino, di- (C 1 -C 4 -alkyl) -amino and C 3 -C 6 -cycloalkyl Saturated or unsaturated heterocyclyl, heterocyclicamino or heterocyclylimino, which in each case is monocyclic or bicyclic, optionally substituted by one or more groups selected. 제 1 항에 있어서,The method of claim 1, R1이 수소, 불소 또는 염소를 나타내고,R 1 represents hydrogen, fluorine or chlorine, R2는 그룹 -A1-A2-A3를 나타내며,R 2 represents a group -A 1 -A 2 -A 3 , 여기에서,From here, A1은 단일 결합, -O- 또는 그룹 -N-A4- (여기에서, A4는 수소 또는 메틸을 나타낸다)을 나타내고,A 1 represents a single bond, -O- or group -NA 4- , wherein A 4 represents hydrogen or methyl, A2는 단일 결합, -SO2-, 메틸렌 또는 에탄-1,1-디일을 나타내며,A 2 represents a single bond, -SO 2- , methylene or ethane-1,1-diyl, A3은 하이드록실, 아미노, 불소, 메틸, 에틸, n- 또는 i-프로필, 임의로 불소- 또는 메톡시-치환된 에톡시, n- 또는 i-프로폭시, 메톡시에톡시에톡시, 또는 에티닐을 나타내고,A 3 is hydroxyl, amino, fluorine, methyl, ethyl, n- or i-propyl, optionally fluorine- or methoxy-substituted ethoxy, n- or i-propoxy, methoxyethoxyethoxy, or Represent tinyl, R3은 수소를 나타내며,R 3 represents hydrogen, Z 는 각 경우에 헤테로사이클릭 환 계에 1 내지 3 개의 질소 원자 및 2 내지 8개의 탄소 원자를 가지며 임의로 -CO- 및/또는 -CS- 중에서 선택된 2 개 이하의 그룹을 함유하고 염소, 임의로 불소-치환된 메틸, 에틸, n- 또는 i-프로필, n-부틸, 메틸아미노, 디메틸아미노 및 사이클로프로필로 구성된 그룹중에서 선택된 하나 이상의 그룹에 의해 임의로 치환되는, 각 경우에 모노사이클릭 또는 비사이클릭인 포화 또는 불포화 헤테로사이클릴, 헤테로사이클릴아미노 또는 헤테로사이클릴이미노를 나타냄을 특징으로 하는 일반식 (I)의 치환된 방향족 티오카복스아미드.Z has in each case 1 to 3 nitrogen atoms and 2 to 8 carbon atoms in the heterocyclic ring system and optionally contains up to 2 groups selected from -CO- and / or -CS- and chlorine, optionally fluorine Monocyclic or acyclic in each case optionally substituted by one or more groups selected from the group consisting of substituted methyl, ethyl, n- or i-propyl, n-butyl, methylamino, dimethylamino and cyclopropyl Substituted aromatic thiocarboxamides of formula (I) characterized by representing phosphorus saturated or unsaturated heterocyclyl, heterocyclylamino or heterocyclylimino. 일반식 (II) 의 치환된 방향족 니트릴을, 임의로 반응 보조제의 존재하 및 임의로 희석제의 존재하에서 황화수소(H2S) 또는 티오아세트아미드와 반응시킴을 특징으로 하여, 일반식 (I) 의 치환된 방향족 티오카복스아미드를 제조하는 방법 :The substituted aromatic nitrile of formula (II) is reacted with hydrogen sulfide (H 2 S) or thioacetamide, optionally in the presence of a reaction aid and optionally in the presence of a diluent, so that the substituted aromatic nitrile of formula (I) How to prepare aromatic thiocarboxamides: 상기 식에서, R1, R2, R3및 Z 는 제 2 항에 언급된 의미를 갖는다.Wherein R 1 , R 2 , R 3 and Z have the meanings mentioned in claim 2. 제 1 항 또는 2 항에 따른 일반식 (I) 의 치환된 방향족 티오카복스 아미드를 원치않는 식물 및/또는 그들의 서식지에 작용시킴을 특징으로 하여 원치않는 식물을 구제하는 방법.A method for controlling unwanted plants, characterized in that the substituted aromatic thiocarbox amides of formula (I) according to claim 1 or 2 are acted on unwanted plants and / or their habitats. 제 1 항 또는 2 항에 따른 일반식 (I) 의 치환된 방향족 티오카복스 아미드를 증량제 및/또는 계면활성물질과 혼합함을 특징으로 하여 제초제 조성물을 제조하는 방법.A process for preparing herbicide composition, characterized in that the substituted aromatic thiocarbox amide of formula (I) according to claim 1 or 2 is mixed with an extender and / or a surfactant. 제 1 항 또는 2 항에 따른 일반식 (I) 의 치환된 방향족 티오카복스 아미드를 적어도 하나 함유함을 특징으로 하는 제초제 조성물.Herbicide composition characterized in that it contains at least one substituted aromatic thiocarbox amide of formula (I) according to claim 1. 제 1 항에 있어서,The method of claim 1, Z는 식 Z1, Z2, Z3, Z9, Z10또는 Z15를 나타내고,Z represents the formula Z 1 , Z 2 , Z 3 , Z 9 , Z 10 or Z 15 , 여기에서, Q1은 -CO- 또는 -CS- 를 나타내며,Wherein Q 1 represents -CO- or -CS-, R6은 수소, 불소, 염소, 브롬, 메틸, 에틸, n- 또는 i-프로필, 사이클로프로필, 디플루오로메틸, 트리플루오로메틸 또는 클로로디플루오로메틸을 나타내고,R 6 represents hydrogen, fluorine, chlorine, bromine, methyl, ethyl, n- or i-propyl, cyclopropyl, difluoromethyl, trifluoromethyl or chlorodifluoromethyl, R7은 메틸, 에틸, n- 또는 i-프로필을 나타내거나, 두개의 인접한 그룹 -R6및 R6또는 R6및 R7- 이 함께 C1-C4-알칸디일을 나타냄을 특징으로 하는 일반식 (I) 의 치환된 방향족 티오카복스아미드.R 7 represents methyl, ethyl, n- or i-propyl, or two adjacent groups -R 6 and R 6 or R 6 and R 7 -together represent C 1 -C 4 -alkanediyl Substituted aromatic thiocarboxamide of formula (I). 제 1 항에 있어서,The method of claim 1, R1은 불소를 나타내고,R 1 represents fluorine, R2는 -NH-SO2-C2H5를 나타내며,R 2 represents -NH-SO 2 -C 2 H 5 , R3은 수소를 나타내고,R 3 represents hydrogen, Z는를 나타냄을 특징으로 하는 일반식 (I) 의 치환된 방향족 티오카복스아미드.Z is Substituted aromatic thiocarboxamide of formula (I).
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