KR0131531B1 - Novel herbicidal triazole derivatives - Google Patents
Novel herbicidal triazole derivativesInfo
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- KR0131531B1 KR0131531B1 KR1019940030432A KR19940030432A KR0131531B1 KR 0131531 B1 KR0131531 B1 KR 0131531B1 KR 1019940030432 A KR1019940030432 A KR 1019940030432A KR 19940030432 A KR19940030432 A KR 19940030432A KR 0131531 B1 KR0131531 B1 KR 0131531B1
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
- C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
- C07D405/12—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings linked by a chain containing hetero atoms as chain links
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- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
- A01N43/90—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having two or more relevant hetero rings, condensed among themselves or with a common carbocyclic ring system
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D249/00—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms
- C07D249/02—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms not condensed with other rings
- C07D249/08—1,2,4-Triazoles; Hydrogenated 1,2,4-triazoles
- C07D249/10—1,2,4-Triazoles; Hydrogenated 1,2,4-triazoles with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D249/12—Oxygen or sulfur atoms
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
- C07D307/02—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings
- C07D307/04—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having no double bonds between ring members or between ring members and non-ring members
- C07D307/10—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having no double bonds between ring members or between ring members and non-ring members with substituted hydrocarbon radicals attached to ring carbon atoms
- C07D307/14—Radicals substituted by nitrogen atoms not forming part of a nitro radical
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- General Health & Medical Sciences (AREA)
- Wood Science & Technology (AREA)
- Zoology (AREA)
- Environmental Sciences (AREA)
- Pest Control & Pesticides (AREA)
- Agronomy & Crop Science (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Plural Heterocyclic Compounds (AREA)
Abstract
Description
본 발명은 하기 일반식(Ⅰ)로 표시되는 신규 제초성 티리아졸 유도체에 관한 것이다.The present invention relates to a novel herbicidal tyrazole derivative represented by the following general formula (I).
상기식에서, X는 탄소원자, 산소원자 또는 질소원자를 나타내고, R1은 수소원자 C1-C4알킬, C2-C4알케닐, C3-C4알키닐, 페닐 또는 벤질을 나타내며, R2와 R3는 같거나 다르고, 수소, C1-C4알킬, C3-C6시클로알킬 또는 C2-C4알케닐을 나타낸다.Wherein X represents a carbon atom, an oxygen atom or a nitrogen atom, R 1 represents a hydrogen atom C 1 -C 4 alkyl, C 2 -C 4 alkenyl, C 3 -C 4 alkynyl, phenyl or benzyl, R 2 and R 3 are the same or different and represent hydrogen, C 1 -C 4 alkyl, C 3 -C 6 cycloalkyl or C 2 -C 4 alkenyl.
상기 정의 중에서, 용어 알킬은 메틸, 에틸, n-프로필, 이소프로필 또는 여러 가지 부틸 이성질체등과 같은 직쇄 또는 측쇄 포화 탄화수소 래디칼을 의미하고; 알케닐은 비닐, 1-프로페닐, 2-프로페닐 및 여러 가지 부테닐 등의 이성질체와 같은 직쇄 또는 측쇄 알켄을 의미하고; 알키닐은 프로파길과 같은 알킨을 의미한다. 종래에도 트리아졸 유도체들이 제초제로서 유용하다는 것이 잘 알려져 있었으나, 그 중에서도 1-카바모일-3-설포닐-1,2,4-트리아졸 유도체들이 특히 제초할성이 뛰어나다는 것이 밝혀진 이후(P.estic. Sei. 1975, vol 6, p665-673), 이들 유도체에 대한 연구가 활발하게 진행되어오고 있다. 본 발명은 제초제로서 유용한 신규의 트리아졸 유도체, 구체적으로 1-카바모일-3-설포닐-1,2,4-트리아졸 유도체에 관한 것이다. 본 발명과 유사한 구조를 갖는 선행 특허로서, 미합중국 특허원 제 4,889,553호, 일본국 특허 공개 제 04-187678호, 제 04-321671호, 제 05-163252호, 제 05-163253호, 제 05-140125호 및 제 05-140123호에 하기 일반식(Ⅱ)로 표시될 수 있는 트리아졸 화합물이 공지되어 있으나 본 발명에서 처럼, 테트라히드로푸란 고리가 치환되어 있는 화합물은 전혀 보고 되어 있지 않다.In the above definitions, the term alkyl means straight or branched chain saturated hydrocarbon radicals such as methyl, ethyl, n-propyl, isopropyl or various butyl isomers and the like; Alkenyl means straight or branched alkene such as isomers such as vinyl, 1-propenyl, 2-propenyl and various butenyl; Alkynyl means alkyne, such as propargyl. It is well known that triazole derivatives are useful as herbicides in the past, but among them, 1-carbamoyl-3-sulfonyl-1,2,4-triazole derivatives have been found to be particularly excellent in herbicidal activity (P. estic.Sei. 1975, vol 6, p665-673), studies of these derivatives have been actively conducted. The present invention relates to novel triazole derivatives useful as herbicides, in particular 1-carbamoyl-3-sulfonyl-1,2,4-triazole derivatives. As a prior patent having a structure similar to the present invention, U.S. Patent No. 4,889,553, Japanese Patent Application Laid-Open Nos. 04-187678, 04-321671, 05-163252, 05-163253, 05-140125 Nos. And 05-140123 disclose triazole compounds which can be represented by the following general formula (II), but as in the present invention, no compound in which the tetrahydrofuran ring is substituted is reported.
본 발명자들은 상기의 문헌들에서 공지되어 있지 않은 신규하면서도 제초력이 우수한 트리아졸 유도체를 개발하였다. 본 발명의 하기 일반식(Ⅰ)로 표시되는 신규 제초성 트리아졸 유도체에 관한 것이다.The inventors have developed a novel but excellent herbicide triazole derivative which is not known in the above documents. The present invention relates to a novel herbicidal triazole derivative represented by the following general formula (I).
상기식에서, X는 탄소원자, 산소원자 또는 질소원자를 나타내고, R1는 수소원자 C1-C4알킬, C2-C4알케닐, C3-C4알키닐, 페닐 또는 벤질을 나타내며, R2와 R3는 같거나 다르고, 수소, C1-C4알킬, C3-C6시클로알킬 또는 C2-C4알케닐을 나타낸다. 본 발명은 바람직하게는 X가 질소원자를 나타내고, R1는 수소, 메틸, 에틸, 알릴 또는 프로파길을 나타내며, R2와 R3는 같거나 다르고, 메틸, 에틸, 프로필 또는 시클로프로필을 나타내는 화합물에 관한 것이다. 본 발명에 따른 일반식(Ⅰ)로 표시되는 화합물의 대표적 예는 표 1에 제시된다.Wherein X represents a carbon atom, an oxygen atom or a nitrogen atom, R 1 represents a hydrogen atom C 1 -C 4 alkyl, C 2 -C 4 alkenyl, C 3 -C 4 alkynyl, phenyl or benzyl, R 2 and R 3 are the same or different and represent hydrogen, C 1 -C 4 alkyl, C 3 -C 6 cycloalkyl or C 2 -C 4 alkenyl. The present invention preferably is a compound in which X represents a nitrogen atom, R 1 represents hydrogen, methyl, ethyl, allyl or propargyl, and R 2 and R 3 are the same or different and represent methyl, ethyl, propyl or cyclopropyl It is about. Representative examples of the compound represented by the general formula (I) according to the present invention are shown in Table 1.
본 발명에 따른 일반식(Ⅰ)의 화합물은 하기 반응식 (A)에 따라 하기 일반식(Ⅲ)의 화합물과 하기 일반식(Ⅳ)의 화합물을 염기의 존재하에 반응시킴으로써 제조할 수 있다:Compounds of formula (I) according to the invention can be prepared by reacting a compound of formula (III) with a compound of formula (IV) in the presence of a base according to Scheme (A):
[반응식 A]Scheme A
상기식에서, X는 질소원자를 나타내고, Y는 할로겐 원자를 나타내며, R1, R2, 및 R3는 상기 언급한 바와 같다. 상기 반응식(A)에서 용매는 테트라히드로 푸란, 디클로로메탄, 에틸메틸 케톤과 같은 탄화수소계 용매나 아세토니트릴, 프로피오니트릴과 같은 니트릴류 용매 및 디메틸포름아미드, 디메틸 아세트아미드와 같은 극성용매가 바람직하다. 염기로서는 정량의 수소화 나트륨, 수소화 칼륨, 탄산수소나트륨, 탄산수소칼륨 등의 무기 염기 및 트리에틸아민, 피리딘, N,N-디에틸아닐린 등의 유기염기가 바람직하다. 반응은 고온 또는 상온에서 수행할 수 있다. 상기 반응식(A)에서 출발물질로 사용되는 일반식(Ⅲ)의 화합물은 하기 일반식(Ⅴ)의 화합물은 반응식(13)에따라 화합물로부터 용이하게 합성된다:Wherein X represents a nitrogen atom, Y represents a halogen atom, and R 1 , R 2 , and R 3 are as mentioned above. The solvent in the reaction scheme (A) is preferably a hydrocarbon solvent such as tetrahydrofuran, dichloromethane, ethylmethyl ketone, a nitrile solvent such as acetonitrile or propionitrile, and a polar solvent such as dimethylformamide or dimethyl acetamide. . As the base, inorganic bases such as quantitative sodium hydride, potassium hydride, sodium hydrogen carbonate and potassium hydrogen carbonate and organic bases such as triethylamine, pyridine, N, N-diethylaniline are preferable. The reaction can be carried out at high temperature or room temperature. Compounds of formula (III) used as starting materials in Scheme (A) are readily synthesized from compounds according to Scheme (13):
[반응식B]Scheme B
상기식에서, X는 질소원자를 나타내고, R2및 R3는 상기 언급한 바와 같다. 상기 반응식(B)에서 출발물질로 사용되는 일반식(Ⅴ)의 화하물은 공지의 방법에 따라 쉽게 합성되어진다(참조 : 세계특허 제 93-21164호, 일본국 특허공개 제 05-43557호). 적당한 용매로서 피리딘, 트리에틸아민, 디클로로메탄이 바람직하다. 이하, 본 발명을 실시예에 의거하여 보다 구체적으로 설명한다. 그러나, 이들 실시예는 본 발명에 대한 이해를 돕기 위한 것일뿐 본 발명이 여기에 한정되는 것은 아니다.Wherein X represents a nitrogen atom and R 2 and R 3 are as mentioned above. The compound of Formula (V), which is used as a starting material in Scheme (B), is easily synthesized according to a known method (see, for example, World Patent Nos. 93-21164 and Japanese Patent Publication No. 05-43557). . Pyridine, triethylamine, dichloromethane are preferred as suitable solvents. EMBODIMENT OF THE INVENTION Hereinafter, this invention is demonstrated more concretely based on an Example. However, these examples are only for the understanding of the present invention, and the present invention is not limited thereto.
[실시예 1]Example 1
N-(2-테트라히드로푸라닐메틸)[1-(디에틸카바모일)-1,2,4-트리아졸-3-일]설폰아미드(화합물 5)의 합성Synthesis of N- (2-tetrahydrofuranylmethyl) [1- (diethylcarbamoyl) -1,2,4-triazol-3-yl] sulfonamide (Compound 5)
공지의 화합물인 1-디에틸카바모일-3-클로로설포닐-1,2,4-트리아졸(Ⅴ-1)로부터 상기 반응식(B)에 따라 합성하였다. 1-디에틸카바모일-3-클로로설포닐-1,2,4-트리아졸2.5g과 2-테트라히드로푸라닐메틸아민 1.5g을 디클로로메탄 20㎖에 가하고 2시간동안 상온에서 강하게 교반시킨다. 반응 혼합물을 여과시킨후 감압증류하여 용매를 제거한 잔류물을 실리카겔 상에서 칼럼크로마토그래피(헥산 : 에틸 아세테이트 = 2 : 1)하여 표제 화합물(5) 2.1g(수율 : 90%)을 수득한다.It synthesize | combined according to said reaction formula (B) from the well-known compound 1-diethylcarbamoyl-3-chlorosulfonyl-1,2,4-triazole (V-1). 2.5 g of 1-diethylcarbamoyl-3-chlorosulfonyl-1,2,4-triazole and 1.5 g of 2-tetrahydrofuranylmethylamine are added to 20 ml of dichloromethane and stirred vigorously at room temperature for 2 hours. The reaction mixture was filtered and distilled under reduced pressure to remove the solvent, and the residue was purified by column chromatography on silica gel (hexane: ethyl acetate = 2: 1) to obtain 2.1 g (yield: 90%) of the title compound (5).
1H NMR(CDCl3, δ) : δ1.3(t, 6H), 1.7-1.9(m, 4H), 3.6(m, 4H), 3.8(m, 2H), 4.1(m, 1H), 5.7(m, 1H), 8.86(s, 1H) 1 H NMR (CDCl 3 , δ): δ 1.3 (t, 6H), 1.7-1.9 (m, 4H), 3.6 (m, 4H), 3.8 (m, 2H), 4.1 (m, 1H), 5.7 (m, 1 H), 8.86 (s, 1 H)
[실시예 2]Example 2
N-메틸-N-(2-테트라히드로푸라닐메틸)[1-(디에틸카바모일)-1,2,4-트리아졸-3-일]설폰아미드(화합물 6)의 합성Synthesis of N-methyl-N- (2-tetrahydrofuranylmethyl) [1- (diethylcarbamoyl) -1,2,4-triazol-3-yl] sulfonamide (Compound 6)
실시예 1에서 합성한 N-(2-테트라히드로푸라닐메틸)[1-(디에틸카바모일)-1,2,4-트리아졸-3-일]설폰아미드(화합물 5) 1.5g과 브로모메탄 1.0 g을 테트라히드로푸란 200㎖에 가하고 교반한다. 교반후 에틸 아세테이트 100㎖를 첨가하고 물로 세척한다. 기층을 분리한 뒤 무수망초로 탈수·여과시키고 감압증발시켜서 얻은 잔류물을 실리카겔 상에서 칼럼크로마토그래피(헥산 : 에틸아세테이트 = 1 : 1)하여 표제 화합물(6) 1.4g(수율 : 90%)을 얻는다.1.5 g of N- (2-tetrahydrofuranylmethyl) [1- (diethylcarbamoyl) -1,2,4-triazol-3-yl] sulfonamide (Compound 5) synthesized in Example 1 and bro 1.0 g of methane is added to 200 ml of tetrahydrofuran and stirred. After stirring, 100 ml of ethyl acetate is added and washed with water. After separating the base layer, dehydration and filtration with anhydrous forget-me-not and evaporation under reduced pressure, the residue obtained by column chromatography on silica gel (hexane: ethyl acetate = 1: 1) to obtain 1.4 g (yield: 90%) of the title compound (6). .
1H NMR(CDCl3, δ) : δ1.3(t, 6H), 1.7-1.9(m, 4H), 3.09(s, 3H), 3.22(d, 1H), 3.5(d, 1H), 3.6(m, 4H), 3.8(m, 2H), 4.2(m, 1H), 8086(s, 1H) 1 H NMR (CDCl 3 , δ): δ1.3 (t, 6H), 1.7-1.9 (m, 4H), 3.09 (s, 3H), 3.22 (d, 1H), 3.5 (d, 1H), 3.6 (m, 4H), 3.8 (m, 2H), 4.2 (m, 1H), 8086 (s, 1H)
실시예 1 및 실시예 2와 동일한 방법으로 행하여 상기 표1에 나타난 화합물을 합성하였다. 합성된 화합물들의 물리적 성질을 하기 표 2에 나타내었다.In the same manner as in Example 1 and Example 2, the compounds shown in Table 1 were synthesized. The physical properties of the synthesized compounds are shown in Table 2 below.
본 발명에 따른 일반식(Ⅰ)의 신규성 제초성 2.6-디(4,6-디메톡시피리미딘-2-일)옥시벤조산의 페닐이미노에스테르 유도체의 제초효력을 검정하기 위하여 온실에서 검정식물을 포트 재배 및 처리방법으로 수행하고, 효력판정은 약효 및 약해 평가기준(표 3)에 따라 달관평가를 실시한다. 효력검정을 위하여, 밭 잡초로는 바랭이(Digitaria sanguinalis), 뚝새풀(Alopecurus aequallis), 강아지풀(Setaria farberi), 돌피(Echinochgloa crus-galliva, caudata), 왕바랭이(Elrsim indica), 개밀(Agropyron tsukushiense)를 선정한다. 본 발명에 따른 화합물을 이용할 때는 검토, 활석, 규조토 등의 고형물질과 물, 알콜, 벤젠, 톨루엔, 에테르, 케톤류, 에스테르류, 산류, 아미드류 등의 액체물질과 혼용하여 액제, 유제, 분제, 입제 등의 임의의 제형으로 조제 및 사용할 수 있으며, 이때 필요에 따라 유화제, 분산제, 침투제, 전착제, 안정제를 첨가한다. 다음 본 발명에 따른 화합물을 유효성분으로 하는 제초제의 배합예를 일부 나타냈으나 이러한 방법으로 본 발명을 한정해서도 안된다.Novel herbicide of general formula (I) according to the present invention assays in greenhouses to assay the herbicidal efficacy of phenyliminoester derivatives of 2.6-di (4,6-dimethoxypyrimidin-2-yl) oxybenzoic acid It is carried out by pot cultivation and treatment method, and the efficacy judgment is carried out in accordance with the evaluation criteria of efficacy and weakness (Table 3). Field weeds include Digitaria sanguinalis, Alopecurus aequallis, Setaria farberi, Echinochgloa crus-galliva, caudata, Elrsim indica, and Wheatgrass (Agropyron tsukushiense). Select. When the compound according to the present invention is used, it is mixed with a solid substance such as talc, diatomaceous earth and liquid substances such as water, alcohol, benzene, toluene, ether, ketones, esters, acids, amides, etc. It may be prepared and used in any formulation such as granules, in which case emulsifiers, dispersants, penetrants, electrodeposition agents, stabilizers are added. Some examples of the formulation of the herbicide containing the compound according to the present invention as an active ingredient are shown, but the present invention should not be limited by this method.
[배합예 1]Formulation Example 1
(밭조건 500g/㏊)(Field conditions 500g / ㏊)
본 발명에 따른 화합물 160㎎을 유기용액(아세톤) 640㎖에 용해시킨후 비이온성 계면활성제 트윈 20이 0.2% 함유된 증류수 640㎖에 희석시켜 배합액을 만든다.160 mg of the compound according to the present invention was dissolved in 640 ml of an organic solution (acetone), and then diluted in 640 ml of distilled water containing 0.2% of the nonionic surfactant Tween 20 to prepare a blend.
[실험예 1]Experimental Example 1
(토양처리에 의한 발아전 제초력 검정(밭조건))(Measurement of herbicidal power before germination by soil treatment (field conditions))
사각 프라스틱 용기(20×15×10㎝)에 살균처리된 밭토양(사질양토, pH 5.5-6.0)을 충진한후 표면적이 300㎠인 상태에서 밭잡초 6초종을 하나의 용기에 파종하고 0.5㎝로 목토한다. 관수 1일후 상기 배합에 1의 용액에서 처리 약량(500g/㏊)에 해당하는 유효성분을 토양표면에 균일하게 살포한다. 처리후 30일동안 식물재배 및 관찰후 잡초에 대한 제초력을 평가기준을 따라 달관 평가하고, 그 결과를 표 4에 나타내었다.After filling a rectangular plastic container (20 × 15 × 10㎝) with sterilized field soil (sand loam, pH 5.5-6.0), sowing 6 weeds in one container with a surface area of 300㎠ and 0.5cm To vomiting. After 1 day of irrigation, the formulation is sprayed uniformly with the active ingredient corresponding to the treatment amount (500 g / dl) in the solution of 1. For 30 days after treatment, herbicide power on plant cultivation and weeding were observed according to the evaluation criteria, and the results are shown in Table 4.
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