KR100345850B1 - 1-Benzyl-4,5-dicarbonyl-1,2,3-triazole derivative and process for preparation thereof - Google Patents
1-Benzyl-4,5-dicarbonyl-1,2,3-triazole derivative and process for preparation thereof Download PDFInfo
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- KR100345850B1 KR100345850B1 KR1019970000117A KR19970000117A KR100345850B1 KR 100345850 B1 KR100345850 B1 KR 100345850B1 KR 1019970000117 A KR1019970000117 A KR 1019970000117A KR 19970000117 A KR19970000117 A KR 19970000117A KR 100345850 B1 KR100345850 B1 KR 100345850B1
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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
- C07D249/04—1,2,3-Triazoles; Hydrogenated 1,2,3-triazoles
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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
- A01N43/64—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with three nitrogen atoms as the only ring hetero atoms
- A01N43/647—Triazoles; Hydrogenated triazoles
Abstract
Description
본 발명은 하기 일반식 (I)로 표시되는 1,2,3-트리아졸 구조를 갖는 신규한 제초성 화합물에 관한 것이다. 좀 더 구체적으로, 본 발명은 하기 일반식 (I)의 신규한 1-벤질-4,5-디카르보닐-1,2,3-트리아졸 유도체, 그의 제조방법 및 그 화합물을 유효성분으로 함유함을 특징으로하는 제초제 조성물에 관한 것이다.The present invention relates to a novel herbicidal compound having a 1,2,3-triazole structure represented by the following general formula (I). More specifically, the present invention contains a novel 1-benzyl-4,5-dicarbonyl-1,2,3-triazole derivative of the following general formula (I), a preparation method thereof and a compound thereof as an active ingredient It relates to a herbicide composition characterized in that.
상기식에서In the above formula
Q 는 디(Cl-C4알킬)아미노, 디(C3-C6사이클로알킬)아미노를 나타내거나, 1 내지 5개의 R(여기서, R 은 할로겐, 시아노, 니트로, Cl-C4알킬, 벤질 또는 Cl-C4알콕시이다)에 의해 치환될 수 있는 1-피롤릴, 1-이미다졸릴, 1-피라졸릴, 1,2,3-트리아졸릴, 1,2,4-트리아졸릴, 1,3,4-트리아졸릴, 1-피페리디닐, 1-피페라지닐,4-모폴리닐, 4-황화모폴리닐을 나타내고,Q represents di (C 1 -C 4 alkyl) amino, di (C 3 -C 6 cycloalkyl) amino, or 1 to 5 R, wherein R is halogen, cyano, nitro, C 1 -C 4 1-pyrrolyl, 1-imidazolyl, 1-pyrazolyl, 1,2,3-triazolyl, 1,2,4-tria which may be substituted by alkyl, benzyl or C 1 -C 4 alkoxy) Zolyl, 1,3,4-triazolyl, 1-piperidinyl, 1-piperazinyl, 4-morpholinyl, 4-sulfonyl sulfide,
W 는 하이드록시, Cl-C4알콕시 또는 Q 를 나타낸다.W represents hydroxy, C 1 -C 4 alkoxy or Q.
상기 치환체의 정의 중에서 용어 '알킬'은 메틸, 에틸, n-프로필, 이소프로필, 또는 여러가지의 부틸 이성체 등과 같은 직쇄 또는 측쇄 포화 탄화수소 라디칼을 의미하고, 용어 '사이클로알킬'은 사이클로프로필, 사이클로부틸, 사이클로펜틸, 사이클로헥실을 의미하며, 용어 '알콕시'는 메톡시, 에톡시, n-프로폭시, 이소프로폭시 또는 여러가지의 부톡시 이성체를 의미하고, 용어 '할로겐'은 불소, 염소, 브롬 또는 요오드를 의미한다.In the definition of the substituent, the term 'alkyl' refers to a straight or branched chain saturated hydrocarbon radical such as methyl, ethyl, n-propyl, isopropyl, or various butyl isomers, etc., and the term 'cycloalkyl' refers to cyclopropyl, cyclobutyl, Meaning cyclopentyl, cyclohexyl, the term 'alkoxy' means methoxy, ethoxy, n-propoxy, isopropoxy or various butoxy isomers, and the term 'halogen' means fluorine, chlorine, bromine or iodine Means.
종래에도 1,2,3-트리아졸 유도체들이 유용한 약리 작용을 보이는 것으로 알려져 있었으나(참조: 유럽특허원 제 229011 호, 199262 호, 일본특허공개 59118775 호), 이들 화합물은 의약물질로서만 소개되어 있을 뿐, 아직까지 1,2,3-트리아졸 유도체들이 제초제로서 사용되었다는 보고는 없다.Conventionally, 1,2,3-triazole derivatives have been known to exhibit useful pharmacological action (see European Patent Application No. 229011, 199262, and Japanese Patent Publication No. 59118775), but these compounds may be introduced only as pharmaceuticals. However, there are no reports of 1,2,3-triazole derivatives being used as herbicides.
이에 본 발명자들은 신규한 구조를 갖고 있으면서도 제초력이 뛰어난 1,2,3-트리아졸 유도체를 개발하고자 1,2,3-트리아졸-4,5-디카르보닐 골격에 대해 광범위한 연구를 수행하였으며, 그 결과 상기 일반식 (I)로 표시되는 화합물이 이러한 목적에 부합됨을 발견하고 본 발명을 완성하게 되었다. 이하, 본 발명의 구성을 상세히 설명한다.Accordingly, the present inventors conducted extensive research on the 1,2,3-triazole-4,5-dicarbonyl skeleton to develop 1,2,3-triazole derivatives having a novel structure and excellent herbicidal power. As a result, the inventors have found that the compound represented by the general formula (I) meets this purpose, and have completed the present invention. Hereinafter, the configuration of the present invention will be described in detail.
본 발명은 하기 일반식 (I)의 신규한 1-벤질-4,5-디카르보닐-1,2,3-트리아졸유도체를 제공함을 목적으로 한다.An object of the present invention is to provide a novel 1-benzyl-4,5-dicarbonyl-1,2,3-triazole derivative of the following general formula (I).
상기식에서In the above formula
Q 는 디(Cl-C4알킬)아미노, 디(C3-C6사이클로알킬)아미노를 나타내거나, 1 내지 5개의 R(여기서, R 은 할로겐, 시아노, 니트로, Cl-C4알킬, 벤질 또는 Cl-C4알콕시이다)에 의해 치환될 수 있는 1-피롤릴, 1-이미다졸릴, 1-피라졸릴, 1,2,3-트리아졸릴, 1,2,4-트리아졸릴, 1,3,4-트리아졸릴, 1-피페리디닐, 1-피페라지닐, 4-모폴리닐, 4-황화모폴리닐을 나타내고,Q represents di (C 1 -C 4 alkyl) amino, di (C 3 -C 6 cycloalkyl) amino, or 1 to 5 R, wherein R is halogen, cyano, nitro, C 1 -C 4 1-pyrrolyl, 1-imidazolyl, 1-pyrazolyl, 1,2,3-triazolyl, 1,2,4-tria which may be substituted by alkyl, benzyl or C 1 -C 4 alkoxy) Zolyl, 1,3,4-triazolyl, 1-piperidinyl, 1-piperazinyl, 4-morpholinyl, 4-sulfonyl sulfide,
W 는 하이드록시, Cl-C4알콕시 또는 Q 를 나타낸다.W represents hydroxy, C 1 -C 4 alkoxy or Q.
상기 본 발명에 따른 일반식 (I)의 화합물은 화본 및 광엽잡초에 대해서 광범위한 제초활성을 나타내며, 일반식 (I) 화합물의 대표적인 예는 하기 표 1 에 나타내었다.The compound of general formula (I) according to the present invention exhibits a wide range of herbicidal activity against flowering plants and broadleaf weeds, and representative examples of the compound of general formula (I) are shown in Table 1 below.
표 1Table 1
표 1. (계속)Table 1. (continued)
한편, 본 발명에 따른 일반식 (I)의 화합물은 하기 반응식 A 및 B 에 나타낸 바에 따라 제조할 수 있으며, 따라서 본 발명은 일반식 (I) 화합물의 제조방법을 제공하는 것을 목적으로 한다.On the other hand, the compound of the general formula (I) according to the present invention can be prepared as shown in the following schemes A and B, and therefore the present invention aims to provide a method for preparing the compound of the general formula (I).
먼저, 일반식 (I)의 화합물 중에서 W 가 하이드록시 또는 Q 인 일반식 (Ia)의 화합물은 하기 반응식 A 에 나타낸 바와 같이 공지의 화합물인 하기 일반식 (II) 의 화합물을 용매중에서 커플링제의 존재하에 하기 일반식 (III) 의 화합물과반응시켜 제조할 수 있다.First, among the compounds of the general formula (I), a compound of the general formula (Ia) in which W is hydroxy or Q is a compound of the general formula (II) below, which is a known compound, as shown in Scheme A below. It may be prepared by reacting with a compound of the general formula (III) in the presence.
반응식 A :Scheme A:
상기식에서,In the above formula,
Q 는 앞에서 정의한 바와 같고,Q is as defined above,
W' 는 하이드록시 또는 Q 를 나타낸다.W 'represents hydroxy or Q.
상기 반응식 A 에 따른 제조방법에서 용매로는 테트라하이드로푸란, 디에틸 에테르 등의 에테르류, 디클로로메탄, 클로로포름, 사염화탄소, 1,2-디클로로에탄 등의 할로겐화 탄화수소류 등을 사용할 수 있으며, 이중에서도 테트라하이드로푸란 또는 디에틸에테르가 바람직하다. 또한, 카복실기를 활성화시키는 커플링제로는 포스겐, 디포스겐, 트리포스겐 등을 바람직하게 사용할 수 있다, 반응은 고온 또는 저온에서 수행될 수 있으며 0 내지 60℃ 범위에서 수행하는 것이 바람직하다. 이러한 조건에서 일반식 (III)의 화합물을 일반식 (II)의 화합물에 대하여 1 내지 2 당량배량으로 사용하여 일반식 (Ia) 화합물을 제조한다.In the preparation method according to Scheme A, ethers such as tetrahydrofuran and diethyl ether, halogenated hydrocarbons such as dichloromethane, chloroform, carbon tetrachloride and 1,2-dichloroethane may be used. Hydrofuran or diethyl ether is preferred. In addition, as the coupling agent for activating the carboxyl group, phosgene, diphosgene, triphosgene, and the like may be preferably used. The reaction may be performed at a high temperature or a low temperature, and is preferably performed at a range of 0 to 60 ° C. Under these conditions, the compound of formula (III) is used in an amount of 1 to 2 equivalents based on the compound of formula (II) to prepare compound of formula (Ia).
일반식 (I)의 화합물에서 W 가 Cl-C4알콕시인 일반식 (Ib)의 화합물은 또한, 하기 반응식 B 에 나타낸 바와 같이 반응식 A 에서 수득된 일반식 (la)의 화합물중에서 W' 가 하이드록시인 하기 일반식 (Ia-1)의 화합물을 용매중에서 촉매의 존재하에 하기 일반식 (IV)의 알콜과 에스테르화 반응을 수행함으로써 제조할 수 있다.Compounds of formula (Ib) wherein W is C 1 -C 4 alkoxy in the compound of formula (I) also have W 'in the compound of formula (la) obtained in Scheme A as The compound of the following general formula (Ia-1) which is hydroxy can be prepared by carrying out an esterification reaction with an alcohol of the following general formula (IV) in the presence of a catalyst in a solvent.
반응식 B :Scheme B:
상기식에서,In the above formula,
Q 는 앞에서 정의한 바와 같고,Q is as defined above,
R 은 Cl-C4알킬을 나타낸다.R represents C 1 -C 4 alkyl.
상기 반응식 B 에 따른 제조방법에서 용매로는 톨루엔, 벤젠 등의 방향족 탄화수소류를 바람직하게 사용하며, 촉매로는 황산, 인산, 톨루엔설폰산 등의 양자성 산을 사용하는 것이 바람직하다. 또한, 반응시 부산물로 생성되는 물은 공비증류에 의해 제거하는 것이 좋다.In the production method according to Scheme B, aromatic hydrocarbons such as toluene and benzene are preferably used as a solvent, and protons such as sulfuric acid, phosphoric acid and toluenesulfonic acid are preferably used as a catalyst. In addition, the water produced as a by-product during the reaction is preferably removed by azeotropic distillation.
본 발명의 또 다른 목적은 유효성분으로서 일반식 (I) 의 화합물을 농약분야에서 사용되는 통상의 담체와 함께 함유함을 특징으로 하는 농작물에 유해한 식물퇴치용 제초제 조성물을 제공하는 것이다.It is still another object of the present invention to provide a herbicide composition for eradicating plants harmful to crops, comprising the compound of formula (I) as an active ingredient together with a conventional carrier used in the agricultural industry.
본 발명에서는 일반식 (I)의 화합물이 소기에 목적하는 바와 같은 제초 효력을 나타내는지 보다 명확하게 검정하기 위하여 온실에서 검정식물에 대해 포트재배 및 약제처리를 수행하였으며 효력판정은 하기 표 2 의 약효 및 약해 평가기준표에 따라 달관평가를 실시하였다.In the present invention, pot cultivation and pharmaceutical treatment were performed on the assay plants in a greenhouse to more clearly verify whether the compound of formula (I) exhibits herbicidal effect as desired. And month-of-month evaluations were conducted according to the weak evaluation criteria table.
표 2 약효 및 약해 평가기준표Table 2 Table of efficacy and weakness evaluation criteria
본 발명에 따른 일반식 (I) 화합물의 효력을 검정하기 위하여, 밭 잡초로는 바랭이(Digitaria sanguinalis), 돌피(Echinochloa crus-galli var.caudata), 자귀풀(Aeschynomene indica), 어저귀(Abutilon theophrasti), 도꼬마리(Xanthium stromarium), 왕바랭이(Eleusine indica), 나팔꽃(Ipomoea spp)을 선정하였고, 논 잡초로는 강피(Echinochloa crus-galli var. oryzicola), 올챙이고랭이(Scirpus juncoides), 물달개비(Monochoria vaginalis), 너도방동산이(Cyperus serotinus), 벗풀(Sagittaria trifolia) 등을 선정하여 실험하였다.To test the efficacy of the compound of formula (I) according to the present invention, field weeds include Digitaria sanguinalis, Echinochloa crus-galli var.caudata, Aeschynomene indica, Abutilon theophrasti, Xanthium stromarium, Eleusine indica, and morning glory (Ipomoea spp) were selected. Echinochloa crus-galli var. Oryzicola, Scirpus juncoides, and moth (Monochoria vaginalis) were selected as paddy weeds. ), Cyperus serotinus, and Sagittaria trifolia were selected and tested.
본 발명의 화합물을 유효성분으로 하여 제초제 조성물을 제조하는 경우에, 일반식 (I)의 화합물은 점토, 활석, 규조토 등의 고형물질 또는 물, 알콜, 벤젠,톨루엔, 에테르, 케톤류, 에스테르류, 산류, 아미드류의 액체물질과 혼용하여 액제, 유제, 분제, 입제 등 임의의 제형으로 조제되어 사용될 수 있으며, 이때 필요에 따라 유화제, 분산제, 침투제, 전착제 및 안정제 중에서 선택된 1 종 이상의 물질을 첨가할 수 있다.When preparing the herbicide composition using the compound of the present invention as an active ingredient, the compound of the general formula (I) may be a solid substance such as clay, talc, diatomaceous earth or water, alcohol, benzene, toluene, ether, ketones, esters, It can be mixed with liquid materials of acids and amides and used in any formulation such as liquids, emulsions, powders, granules, etc.At this time, one or more substances selected from emulsifiers, dispersants, penetrants, electrodeposition agents and stabilizers can be added. Can be.
방제하고자 하는 대상, 연중시기, 대상이 되는 식물 및 그의 성장단계에 따라 본 발명에 따른 활성화합물의 사용량이 변화할 수 있으나, 통상 활성화합물 0.001 내지 5.Okg/ha의 비율로 사용한다.The amount of the active compound according to the present invention may vary depending on the object to be controlled, year-round time, the plant to be grown, and the growth stage thereof, but the active compound is generally used at a ratio of 0.001 to 5.Okg / ha.
이하, 본 발명을 하기 실시예에 의거하여 보다 구체적으로 설명한다. 그러나, 이들 실시예는 본 발명에 대한 이해를 돕기 위한 것일 뿐, 어떤 의미로든 본 발명의 범위가 이들에 의해 한정되는 것은 아니다.Hereinafter, the present invention will be described in more detail based on the following examples. However, these examples are only for the understanding of the present invention, and the scope of the present invention is not limited by them in any sense.
실시예 1: 1-벤질-4-(디사이클로헥실아미노)카르보닐-1H-1,2,3-트리아졸-5-카르복실산(I-10)의 합성Example 1 Synthesis of 1-benzyl-4- (dicyclohexylamino) carbonyl-1H-1,2,3-triazole-5-carboxylic acid (I-10)
1-벤질-lH-1,2,3-트리아졸-4,5-디카르복실산 2.5g 을 질소조건하에 테트라하이드로푸란 50㎖에 가하고 0℃에서 트리에틸아민 1.Og 및 트리포스겐 1.Og을 순서대로 서서히 첨가하였다. 반응 혼합물을 상온에서 1 시간동안 교반하고 5 시간 동안 환류시킨 다음, 뜨거운 반응 혼합물을 여과하였다. 여과시킨 반응 혼합물에 0℃에서 디사이클로헥실아민 1.8g을 서서히 가하고 상온에서 3 시간동안 교반하였다. 반응 혼합물을 여과한 후 감압 증류하여 테트라하이드로푸란을 제거하였다. 잔류물을 디클로로메탄과 탄산수소나트륨 수용액으로 추출하고, 수용액층을 산성화시킨 다음 디클로로메탄으로 추출하였다. 유기층을 감압 증류하여 디클로로메탄을 제거한 다음 실리카겔 칼럼 크로마토그래피(헥산/에틸아세테이트=1/1, v/v)로 분리하여 표제화합물 2.1g(수율: 51%)을 수득하였다.2.5 g of 1-benzyl-lH-1,2,3-triazole-4,5-dicarboxylic acid was added to 50 ml of tetrahydrofuran under nitrogen, followed by triethylamine 1.Og and triphosgene 1. Og was added slowly in order. The reaction mixture was stirred at room temperature for 1 hour and refluxed for 5 hours, then the hot reaction mixture was filtered. 1.8 g of dicyclohexylamine was slowly added to the filtered reaction mixture at 0 ° C. and stirred at room temperature for 3 hours. The reaction mixture was filtered and distilled under reduced pressure to remove tetrahydrofuran. The residue was extracted with dichloromethane and aqueous sodium hydrogen carbonate solution, the aqueous layer was acidified and then extracted with dichloromethane. The organic layer was distilled under reduced pressure to remove dichloromethane, and then separated by silica gel column chromatography (hexane / ethyl acetate = 1/1, v / v) to give 2.1 g (yield: 51%) of the title compound.
실시예 2: 1-벤질-4-(디사이클로헥실아미노)카르보닐-1H-1,2,3-트리아졸-5-카르복실산 메틸에스테르(I-11)의 합성Example 2: Synthesis of 1-benzyl-4- (dicyclohexylamino) carbonyl-1H-1,2,3-triazole-5-carboxylic acid methyl ester (I-11)
실시예 1에서 수득한 1-벤질-4-(디사이클로헥실아미노)카르보닐-lH-1,2,3-트리아졸-5-카르복실산 2.Og 및 메탄올 0.15g을 벤젠 30㎖에 용해시킨 후, 상온에서 진한 황산 몇방울을 적가하였다. 반응혼합물을 딘-스탁 트랩 기구하에 10 시간 동안 환류시킨 다음 벤젠으로 추출하였다. 유기층을 탄산수소나트륨 포화수용액으로 세척해내고, 무수 황산나트륨으로 건조시켰다. 유기층을 감압 증류한 후 실리카겔 칼럼 크로마토그래피(헥산/에틸아세테이트=1/1, v/v)로 분리하여 표제화합물 2.1g(수율: 90%)을 수득하였다.2.Og of 1-benzyl-4- (dicyclohexylamino) carbonyl-lH-1,2,3-triazole-5-carboxylic acid obtained in Example 1 and 0.15 g of methanol were dissolved in 30 ml of benzene. After the addition, a few drops of concentrated sulfuric acid were added dropwise at room temperature. The reaction mixture was refluxed for 10 hours under a Dean-Stark trap apparatus and then extracted with benzene. The organic layer was washed with saturated aqueous sodium hydrogen carbonate solution and dried over anhydrous sodium sulfate. The organic layer was distilled under reduced pressure and separated by silica gel column chromatography (hexane / ethyl acetate = 1/1, v / v) to give 2.1 g (yield: 90%) of the title compound.
실시예 3: 1-벤질-4,5-[(N,N-디에틸아미노)카르보닐]-1H-1,2.3-트리아졸(I-3)의 합성Example 3: Synthesis of 1-benzyl-4,5-[(N, N-diethylamino) carbonyl] -1H-1,2.3-triazole (I-3)
1-벤질-lH-1,2,3-트리아졸-4,5-디카르복실산 2.5g 을 질소조건하에 테트라하이드로푸란 50㎖에 가하고 0℃에서 트리에틸아민 2.Og 및 트리포스겐 2.Og을 순서대로 서서히 첨가하였다. 반응 혼합물을 상온에서 1 시간동안 교반하고 5 시간 동안 환류시킨 다음, 뜨거운 반응 혼합물을 여과하였다. 여과시킨 반응 혼합물에 0℃에서 디에틸아민 1.5g을 서서히 가하고 상온에서 3 시간동안 교반하였다. 반응 혼합물을 여과한 후 감압 증류하여 테트라하이드로푸란을 제거하였다. 잔류물을 디클로로메탄과 탄산수소나트륨 수용액으로 추출하고, 수용액층을 산성화시킨 다음 디클로로메탄으로 추출하였다. 유기층을 감압 증류하여 디클로로메탄을 제거한 다음 실리카겔 칼럼 크로마토그래피(헥산/에틸아세테이트=1/1, v/v)로 분리하여 표제 화합물 2.86g(수율: 80%)을 수득하였다.2.5 g of 1-benzyl-lH-1,2,3-triazole-4,5-dicarboxylic acid was added to 50 ml of tetrahydrofuran under nitrogen, followed by triethylamine 2.Og and triphosgene 2. Og was added slowly in order. The reaction mixture was stirred at room temperature for 1 hour and refluxed for 5 hours, then the hot reaction mixture was filtered. To the filtered reaction mixture was slowly added 1.5 g of diethylamine at 0 ° C. and stirred at room temperature for 3 hours. The reaction mixture was filtered and distilled under reduced pressure to remove tetrahydrofuran. The residue was extracted with dichloromethane and aqueous sodium hydrogen carbonate solution, the aqueous layer was acidified and then extracted with dichloromethane. The organic layer was distilled under reduced pressure to remove dichloromethane, and then separated by silica gel column chromatography (hexane / ethyl acetate = 1/1, v / v) to give 2.86 g (yield: 80%) of the title compound.
상기 실시예 1 내지 3 에 나타낸 것과 동일하게 실시하여 표 1 에 나타낸 화합물들을 합성할 수 있었다.Compounds shown in Table 1 were synthesized in the same manner as described in Examples 1 to 3.
다음은 본 발명에 따른 화합물을 유효 성분으로하는 제초제의 배합예 및 사용예를 일부 나타내었다. 그러나, 이들 배합예 및 사용예도 하나의 예시일 뿐 본 발명의 기술적 범위를 한정하는 것은 아니다.The following shows some examples of the formulation and use of herbicides containing the compound according to the invention as an active ingredient. However, these compounding examples and use examples are only one illustration, and do not limit the technical scope of the present invention.
배합예 1: 유제Formulation Example 1: Emulsion
본 발명의 화합물(10%)을 유기 용매(60%; 아세톤 또는 크실렌 등의 방향족 탄화수소)에 용해시킨 후 계면활성제(30%; 트윈 20 또는 트리톤)를 첨가하여 유제를 수득하였다.The compound (10%) of the present invention was dissolved in an organic solvent (60%; aromatic hydrocarbon such as acetone or xylene) and then surfactant (30%; Tween 20 or Triton) was added to give an emulsion.
배합예 2: 수화제Formulation Example 2: Hydration
본 발명의 화합물(10%), 중량제(80%; 지올라이트, 화이트 카본, 벤토나이트) 및 계면활성제(10%; 폴리옥시에틸렌 알킬아릴설페이트)를 균일하게 혼합한 후 에어 밀로 곱게 분쇄하여 수화제를 수득하였다.A compound of the present invention (10%), a weighting agent (80%; zeolite, white carbon, bentonite) and a surfactant (10%; polyoxyethylene alkylarylsulfate) are uniformly mixed and finely ground with an air mill to hydrate the hydrating agent. Obtained.
배합예 3: 입제Formulation Example 3: Granulation
본 발명의 화합물(3%), 중량제(92%; 탈크와 벤토나이트, 화이트카본) 및 계면활성제(5%; 폴리비닐아세테이트 또는 리그노설포네이트)를 균일하게 혼합하여 펠릿 형태로 살포용 혼합물을 수득하였다.The compound for spraying (3%), the weighting agent (92%; talc and bentonite, white carbon) and the surfactant (5%; polyvinylacetate or lignosulfonate) are uniformly mixed to form a spraying mixture in the form of pellets. Obtained.
배합예 4: 액제Compounding Example 4: Liquid
본 발명의 화합물(20%)을 용매(70%; 이소프로필알콜 또는 물)에 용해시킨 후 계면활성제(10%; 폴리옥시에틸 알킬페닐에테르)를 첨가하여 액제를 수득하였다.Compound (20%) of the present invention was dissolved in a solvent (70%; isopropyl alcohol or water), and then a surfactant (10%; polyoxyethyl alkylphenyl ether) was added to obtain a liquid.
사용예 1: 밭 조건Example 1: Field Conditions
사각 플라스틱 용기(20×15×10cm)에 살균처리된 토양(사질토양, pH 5.5-6.0)을 충진한 후 표면적이 300㎠ 인 상태에서 시험식물의 종자를 종별로 따로 파종한 후 0.5 cm로 목토하였다. 토양처리에 의한 발아전 제초력 검정을 위해서는 관수 1일 후에 정해진 처리약량에 해당하는 유효성분의 배합액을 토양표면에 균일하게 살포하였다. 발아 후의 처치를 위해서는, 시험식물을 먼저 성장 형태에 따라 3 내지 15㎝의 성장 크기로 자라게 한 후, 정해진 처리 약량에 해당하는 유효성분의 배합액을 식물체 경엽부위에 균일하게 살포처리하였다.After filling sterilized soil (sand soil, pH 5.5-6.0) in a rectangular plastic container (20 × 15 × 10 cm), sowing the seeds of each test plant with a surface area of 300 cm2 It was. In order to test the herbicidal power before germination by soil treatment, a mixture of the active ingredients corresponding to the prescribed dose was sprayed uniformly on the soil surface after 1 day of watering. For the treatment after germination, the test plants were first grown to a growth size of 3 to 15 cm according to the growth form, and then the compound solution of the active ingredient corresponding to the prescribed treatment dose was uniformly sprayed on the plant foliage.
식물들은 종에 따라 10-25℃ 또는 20-30℃의 온도로 유지시키고, 실험은 2 내지 4 주에 걸쳐 수행하였으며, 이 기간 동안 식물을 돌보고 각 처리에 따른 식물의 반응을 평가하였다.The plants were kept at a temperature of 10-25 ° C. or 20-30 ° C. depending on the species, and experiments were carried out over two to four weeks, during which time the plants were cared for and the response of the plants with each treatment was evaluated.
사용예 2: 논 조건Use Example 2: Rice Field Conditions
4각 포트(30×15cm)에 살균한 논 토양(식양토, pH 5.5-6.0)을 충진한 후, 표면적이 450㎠ 인 상태에서 벼와 논 잡초를 파종하고 토중 혼입하였다. 토양처리에 의한 발아전 제초력 검정을 위해서는, 관수 1 일 후 정해진 처리약량에 해당하는 유효성분의 배합액을 점적처리하였으며, 발아 후의 처치를 위해서는, 20-25℃의 온실에서 12 내지 14일 동안 재배하여 식물체가 2 내지 3 엽기에 이르면 정해진 처리약량에 해당하는 유효성분의 배합액을 식물체 경엽부위에 균일하게 살포처리하였다. 처리 후 4 내지 5 주동안 재배 및 관찰한 후 각 처리에 따른 식물의 반응을 평가하였다.After filling the sterilized paddy soil (plow soil, pH 5.5-6.0) to each square pot (30 × 15 cm), rice and paddy weeds were sown in the surface area of 450 cm 2 and mixed in soil. In order to test the herbicidal power before germination by soil treatment, a mixture of the active ingredients corresponding to the prescribed treatment amount was dipped after 1 day of watering, and for treatment after germination, it was cultivated for 12 to 14 days in a greenhouse at 20-25 ° C. Thus, when the plants reached 2-3 leaves, the compound solution of the active ingredient corresponding to the prescribed amount of treatment was uniformly sprayed on the plant leaves. After the cultivation and observation for 4 to 5 weeks after the treatment, the response of the plants with each treatment was evaluated.
대표적으로 일반식 (I) 화합물의 제초력을 하기 표 3 에 나타내었다.Representatively, the herbicidal power of the compound of general formula (I) is shown in Table 3 below.
표 3 경엽처리에 의한 발아후 제초력(밭조건, 2kg/ha)Table 3 Weeding power after germination by foliage treatment (field conditions, 2kg / ha)
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| JPS61210075A (en) * | 1985-03-15 | 1986-09-18 | Kureha Chem Ind Co Ltd | Dihydrotriazole and herbicide |
| US5051517A (en) * | 1989-05-20 | 1991-09-24 | Bayer Aktiengesellschaft | Process for the preparation of herbicidally active 3-amino-5-aminocarbonyl-1,2,4-triazoles |
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| Publication number | Priority date | Publication date | Assignee | Title |
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| JPS61210075A (en) * | 1985-03-15 | 1986-09-18 | Kureha Chem Ind Co Ltd | Dihydrotriazole and herbicide |
| US5051517A (en) * | 1989-05-20 | 1991-09-24 | Bayer Aktiengesellschaft | Process for the preparation of herbicidally active 3-amino-5-aminocarbonyl-1,2,4-triazoles |
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| Title |
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| 728쪽 요약, 729쪽 그림, 730쪽 표1, 735쪽 12~22행, Farmaco[Sci], 37(11), 728~739 * |
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