KR0133146B1 - Herbicidal composition - Google Patents
Herbicidal compositionInfo
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- KR0133146B1 KR0133146B1 KR1019940033259A KR19940033259A KR0133146B1 KR 0133146 B1 KR0133146 B1 KR 0133146B1 KR 1019940033259 A KR1019940033259 A KR 1019940033259A KR 19940033259 A KR19940033259 A KR 19940033259A KR 0133146 B1 KR0133146 B1 KR 0133146B1
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom 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
- C07D213/62—Oxygen or sulfur atoms
- C07D213/63—One oxygen atom
- C07D213/64—One oxygen atom attached in position 2 or 6
- C07D213/643—2-Phenoxypyridines; Derivatives thereof
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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
- A01N43/34—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom
- A01N43/40—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom six-membered rings
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/24—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with substituted hydrocarbon radicals attached to ring carbon atoms
- C07D213/26—Radicals substituted by halogen atoms or nitro radicals
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- Agricultural Chemicals And Associated Chemicals (AREA)
- Pyridine Compounds (AREA)
Abstract
Description
본 발명은 신규한 제초성 피리디닐옥시페녹시프로피온산의 히드라지드 유도체에 관한 것이다.The present invention relates to a hydrazide derivative of a novel herbicidal pyridinyloxyphenoxypropionic acid.
좀더 구체적으로, 본 발명은 하기 일반식(I)로 표시되는 신규한 제초성 R-(+)-2-[4-(5-트리플루오로메틸피리딘-2-일옥시)페녹시]프로피온산의 히드라지드 유도체 및 활성 성분으로서 일반식(I)의 화합물을 함유하는 제초제 조성물에 관한 것이다.More specifically, the present invention relates to a novel herbicidal R-(+)-2- [4- (5-trifluoromethylpyridin-2-yloxy) phenoxy] propionic acid represented by the following general formula (I). A herbicide composition containing a hydrazide derivative and a compound of formula (I) as an active ingredient.
상기 식에서, R1 및 R2는 각각 독립적으로 수소, C1-C4알킬, C3-C6사이클로알킬, C2-C4알케닐, 아릴, 벤질, C1-C4알킬카르보닐, C1-C4알킬설포닐 또는 아릴설포닐을 나타낸다.Wherein R 1 and R 2 are each independently hydrogen, C 1 -C 4 alkyl, C 3 -C 6 cycloalkyl, C 2 -C 4 alkenyl, aryl, benzyl, C 1 -C 4 alkylcarbonyl, C 1 -C 4 alkylsulfonyl or arylsulfonyl.
일반식(I)의 화합물의 치환기에 대한 상기 정의에서 용어 알킬은 단독으로 사용될 때나 알킬카르보닐 또는 알킬설포닐과 같이 합성어로 사용될 때나 메틸, 에틸, n-프로필, 이소프로필, n-부틸 또는 그의 이성체 등과 같은 직쇄 또는 측쇄의 포화된 탄화수소 래디칼을 의미하고; 용어 알케닐은 비닐, 1-프로페닐, 2-프로페닐, 여러가지의 부테닐 이성체 등과 같은 직쇄 또는 측쇄 알켄을 의미하며; 용어 아릴은 치환기에 의해 치환되거나 비치환된 페닐을 의미한다.In the above definitions for substituents of compounds of formula (I), the term alkyl is used alone or when used in compound words such as alkylcarbonyl or alkylsulfonyl or methyl, ethyl, n-propyl, isopropyl, n-butyl or Straight chain or branched, saturated hydrocarbon radicals such as isomers and the like; The term alkenyl means straight or branched chain alkenes such as vinyl, 1-propenyl, 2-propenyl, various butenyl isomers and the like; The term aryl means phenyl unsubstituted or substituted by a substituent.
일반적으로 하기 일반식(A)로 표시되는 페녹시프로피오네이트 유도체들이 제조체로서 유용하다는 것은 공지의 사실이다.In general, it is known that phenoxypropionate derivatives represented by the following general formula (A) are useful as preparations.
상기식에서, R은 아릴, 헤테로아릴을 나타내고, R'은 수소, C1-C4알킬을 나타낸다.Wherein R represents aryl, heteroaryl, and R 'represents hydrogen, C 1 -C 4 alkyl.
특히, 이들 페녹시프로피오네이트계 화합물들은 식물체 내에서 지방피질을 생합성하는 과정에 관계하는 것으로 알려진 ACCase(Acetyl Co A Carboxylase) 효소의 활성에 대한 저해제로 작용함으로써 제초활성을 나타내는 것으로 그 작용기작이 밝혀져 있으며(참조 : Weed Sci. 39, 435-449, (1991)), 따라서 광엽식물에는 전혀 해가 없는 특이한 제초제로서 각광받아 왔다.In particular, these phenoxypropionate compounds exhibit herbicidal activity by acting as inhibitors of the activity of ACCase (Acetyl Co A Carboxylase) enzymes known to be involved in the biosynthesis of fat cortex in plants. (Weed Sci. 39, 435-449, (1991)), and have therefore been spotlighted as a unique herbicide with no harm to broadleaf plants.
지금까지 많은 페녹시프로피오네이트 유도체들이 문헌에 보고되고 상품화 되었지만 그 기본적인 골격은 상기 일반식(II)의 구조에서 크게 벗어나지 않았다. 그런데, 극히 최근에 와서 상기 일반식(II)에서 처럼 에스테르 유도체가 아닌 아미드유도체들도 어떤 경우에는 에스테르 유도체 보다 뛰어난 제초활성을 지닌다는 사실이 밝혀졌으며(참조 : 유럽 특허공개 제580,932호 및 제427,549호), 또한 상기 일반식(II)의 두가지 광학 이성체 중에서도 (R)-(+)형태 이성체의 제초활성이 훨씬 뛰어나다는 사실이 보고되었다(참조 : BCPC, p707, 1989).Many phenoxypropionate derivatives have been reported and commercialized in the literature so far, but the basic backbone does not deviate significantly from the structure of formula (II). In recent years, however, it has been found that amide derivatives, which are not ester derivatives, in some cases also have superior herbicidal activity than ester derivatives, as in the general formula (II) (see European Patent Publication Nos. 580,932 and 427,549). ), It was also reported that the herbicidal activity of the (R)-(+) type isomer is much superior among the two optical isomers of general formula (II) (see BCPC, p707, 1989).
따라서, 본 발명자들은 이러한 공지의 사실들을 기초로 하여 신규하면서 제초성이 뛰어난 페녹시프로피오네이트계 유도체를 개발하고자 광범위한 연구를 수행한 결과, 상기 일반식(I)에 나타낸 바와 같은 히드라지드기를 갖는 피리디닐옥시 페녹시프로피오네이트 유도체들이 이러한 목적에 부응하는 것을 발견하고 본 발명을 완성하게 되었다.Accordingly, the present inventors conducted extensive research to develop novel and excellent herbicidal phenoxypropionate derivatives based on these known facts, and thus have hydrazide groups as shown in the general formula (I). It has been found that pyridinyloxy phenoxypropionate derivatives serve this purpose and have completed the present invention.
이하, 본 발명의 구성을 설명하면 다음과 같다.Hereinafter, the configuration of the present invention will be described.
본 발명은 하기 일반식(I)로 표시되는 신규한 R-(t)-2-[4-(5-트리플루오로메틸피리딘-2-일옥시)페녹시]프로피온산의 히드라지드 유도체를 제공함을 목적으로 한다.The present invention provides a hydrazide derivative of the novel R- (t) -2- [4- (5-trifluoromethylpyridin-2-yloxy) phenoxy] propionic acid represented by the following general formula (I) The purpose.
상기 식에서, R1및 R2는 상기 언급한 바와 같다.Wherein R 1 and R 2 are as mentioned above.
신규한 일반식(I)의 화합물 중에서도 바람직한 화합물은, R1및 R2는 각각 독립적으로 수소, C1-C2알킬, 페닐, 벤질, 아세틸, 메틸설포닐 또는 P-틀루엔설포닐을 나타내는 화합물이다.Among the novel compounds of general formula (I), preferred compounds are those in which R 1 and R 2 each independently represent hydrogen, C 1 -C 2 alkyl, phenyl, benzyl, acetyl, methylsulfonyl or P-toluenesulfonyl Compound.
본 발명에 따른 일반식(I)의 제초제 화합물은 콩, 면화 등과 같은 광엽작물에 대해서는 약해가 전혀 없으면서도, 유해한 세엽잡초에 대해서도 탁월한 제초 활성을 지닌다.The herbicide compound of general formula (I) according to the present invention has no harmful effects on broadleaf crops such as soybeans and cotton, and has excellent herbicidal activity against harmful trifoliate weeds.
본 발명에 따른 일반식(I) 화합물의 대표적인 예는 하기 표 1에 나타내었다.Representative examples of the general formula (I) compound according to the present invention are shown in Table 1 below.
한편, 본 발명에 따른 일반식(I)의 화합물은 하기 반응식 A에 따라 하기 구조식(II)의 공지 화합물(참조 : 일본국 특허공개 제3-209366호)과 역시 공지인 하기 일반식(III)의 화합물을 디사이클로헥실카르보디이미드의 존재하에 반응시킴으로써 제조할 수 있다.On the other hand, the compound of the general formula (I) according to the present invention is a known compound of the following structural formula (II) according to Scheme A (reference: Japanese Patent Application Laid-open No. 3-209366) and also the following general formula (III) The compound of can be produced by reacting in the presence of dicyclohexylcarbodiimide.
반응식 A :Scheme A:
상기 식에서, R1및 R2는 상기 언급한 바와 같다.Wherein R 1 and R 2 are as mentioned above.
상기 반응식 A에서 용매로는 디클로로메탄, 클로로포름, 사염화탄소, 1,2-디클로로에탄과 같은 할로겐화 탄화수소를 사용하는 것이 바람직하며, 반응시 사용된 디사이클로헥실카르보디이미드는 구조식(II)의 화합물에 대해 0.5 내지 2.0몰배량, 바람직하게는 0.8 내지 1.2몰배량 사용한다. 또한, 반응은 고온 또는 상온에서 수행할 수 있다.As the solvent in Scheme A, halogenated hydrocarbons such as dichloromethane, chloroform, carbon tetrachloride and 1,2-dichloroethane are preferably used, and the dicyclohexylcarbodiimide used in the reaction may be used for the compound of formula (II). 0.5 to 2.0 mole times, preferably 0.8 to 1.2 mole times. In addition, the reaction can be carried out at a high temperature or room temperature.
이하, 본 발명을 실시예에 의거하여 보다 구체적으로 설명한다. 그러나, 이들 실시예는 본 발명에 대한 이해를 돕기 위한 것일 뿐, 어떤 의미로든 본 발명이 이들 실시예에 한정되는 것은 아니다.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 in any sense, the present invention is not limited to these examples.
[실시예 1]Example 1
화합물(4)(R1=ph, R2=H인 일반식(I)의 화합물)의 합성Synthesis of Compound (4) (Compound of Formula (I) wherein R 1 = ph, R 2 = H)
공지의 화합물인 R-(+)-2[4-(5-트리플루오로메틸피리딘-2-일옥시)페녹시]프로피온산(II) 2.7g과 페닐히드라진 1.2g을 디클로로메탄 50ml에 용해시킨 후 상온에서 교반시켰다. 5분 후에 디사이클로헥실카르보디이미드 2.0g을 첨가한 후 2시간 동안 더 교반시켰다. 반응 혼합물을 여과 농축시키고 실리카겔상에서 컬럼 크로마토그래피(헥산 : 에틸아세테이트(v/v)=2 : 1)로 분리하여 표제 화합물을 3.5g(수율 : 90%) 수득하였다.2.7 g of a known compound R-(+)-2 [4- (5-trifluoromethylpyridin-2-yloxy) phenoxy] propionic acid (II) and 1.2 g of phenylhydrazine were dissolved in 50 ml of dichloromethane. Stir at room temperature. After 5 minutes, 2.0 g of dicyclohexylcarbodiimide was added and further stirred for 2 hours. The reaction mixture was concentrated by filtration and separated by column chromatography on silica gel (hexane: ethyl acetate (v / v) = 2: 1) to obtain 3.5 g (yield: 90%) of the title compound.
실시예 1과 동일한 방법으로 행하여 상기 표 1에 나타낸 화합물들을 합성하였으며, 합성된 화합물들의 물리적 성질은 하기 표 2에 나타내었다.Compounds shown in Table 1 were synthesized in the same manner as in Example 1, and the physical properties of the synthesized compounds are shown in Table 2 below.
본 발명에 따른 일반식(I)의 신규한 제초성 R-(+)-2-[4-(5-트리플루오로메틸피리딘-2-일옥시)페녹시]프로피온산의 히드라지드 유도체의 제초효력을 검정하기 위하여 온실에서 검정식물을 포트재배 및 처리방법으로 수행하고, 효력판정은 약효 및 약해 평가기준(표 3)에 따라 달관평가를 실시한다.Herbicidal efficacy of hydrazide derivatives of novel herbicidal R-(+)-2- [4- (5-trifluoromethylpyridin-2-yloxy) phenoxy] propionic acid according to the present invention In order to test the test, potted plants are treated in the greenhouse by pot cultivation and treatment methods, and the efficacy test is carried out in accordance with the evaluation criteria for efficacy and weakness (Table 3).
효력검정을 위하여, 밭 잡초로는 바랭이(Digitaria sanguinalis), 뚝새풀(Alopecurus aequalaequallisis), 강아지풀(Setaria farberi), 돌피(Echinochgloa curs-gallivar.caudata), 미국개기장(Panicum dichotomiflorum), 왕바랭이(Eleusine indica) 등을 선정하고 작물로는 목화(Gossypium hirsutum)와 콩(Glycine max)을 선정한다.Field weeds include Digitaria sanguinalis, Alopecurus aequalaequallisis, Daria grass (Setaria farberi), Echinochgloa curs-gallivar.caudata, Panicum dichotomiflorum, and Royal Seaweed (Eleusine indica). ) And cotton (Gossypium hirsutum) and soybean (Glycine max) as crops.
본 발명에 따른 화합물을 이용할 때는 점토, 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.When using the compound according to the present invention mixed with solid materials such as clay, talc, diatomaceous earth and liquid materials such as water, alcohol, benzene, toluene, ether, ketones, esters, acids, amides, liquids, emulsions, powders, It may be prepared and used in any formulation such as granules, in which case emulsifiers, dispersants, penetrants, electrodeposition agents, stabilizers are added.
다음 본 발명에 따른 화합물을 유효성분으로 하는 제초제의 배합예를 일부 나타냈으나 이러한 방법으로 본 발명을 한정해서도 안된다.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/haField condition 500g / ha
본 발명에 따른 화합물 160mg을 유기용매(아세톤) 640ml에 용해시킨 후 비이온성 계면활성제 트윈 20이 0.2% 함유된 증류수 640ml에 희석시켜 배합액을 만든다.160 mg of the compound according to the present invention was dissolved in 640 ml of an organic solvent (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
경엽처리에 의한 발아후 제초력 검정(밭조건)Test of herbicidal power after germination by foliage treatment (field conditions)
사각 프라스틱용기(20×15×10cm)에 살균 처리된 밭토양(사질양토, pH 5.5 내지 6.0)을 충진한 후 표면적이 300cm2인 상태에서 밭잡초 6초종을 하나의 용기에 파종하였다. 파종한지 10 내지 14일 동안 재배하여 식물체가 3 내지 4엽기에 이르면 상기 배합예 1에서 처리 약량(500g/ha)에 해당하는 유효성분을 식물체 경엽부위에 균일하게 살포처리 하였다. 처리후 30일 동안 재배 및 관찰후 잡초에 대한 제초력을 평가기준에 따라 달관 평가하고 그 결과를 표 4에 나타내었다.After filling the sterilized field soil (sand loam, pH 5.5 to 6.0) in a rectangular plastic container (20 × 15 × 10 cm), 6 weeds were planted in one container with a surface area of 300 cm 2 . After planting for 10 to 14 days sowing plants reached 3 to 4 leaves, the active ingredient corresponding to the treatment amount (500 g / ha) in the compounding example 1 was uniformly sprayed on the plant leaves. The herbicidal power for weeds after cultivation and observation for 30 days after the treatment was assessed according to the evaluation criteria and the results are shown in Table 4.
[실험예 2]Experimental Example 2
발아후 처리시의 제초효력 및 작물약해 실험Herbicidal Effect and Crop Harm Test in Germination
실험예 1의 방법에 준하여, 잡초와 작물에 대한 효력을 검정하고, 그 결과를 표 5에 나타내었다.In accordance with the method of Experimental Example 1, the effects on the weeds and crops were tested, and the results are shown in Table 5.
실험예 1 및 2의 결과로부터 알 수 있듯이, 본 발명에 따른 일반식(I)의 화합물은 뚝새풀, 강아지풀 등의 세엽잡초에 대해서는 뛰어난 제초효과를 나타내는 반면에, 면화 및 콩과 같은 유용한 광엽 작물에 대해서는 우수한 안전성을 나타내었다.As can be seen from the results of Experimental Examples 1 and 2, the compound of the general formula (I) according to the present invention shows excellent herbicidal effect on tricot weeds such as tufts and pupweeds, while on useful broadleaf crops such as cotton and soybeans. Showed good safety.
Claims (3)
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| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| KR1019940033259A KR0133146B1 (en) | 1994-12-08 | 1994-12-08 | Herbicidal composition |
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| Application Number | Priority Date | Filing Date | Title |
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| KR1019940033259A KR0133146B1 (en) | 1994-12-08 | 1994-12-08 | Herbicidal composition |
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| Publication Number | Publication Date |
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| KR960022467A KR960022467A (en) | 1996-07-18 |
| KR0133146B1 true KR0133146B1 (en) | 1998-04-17 |
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| KR1019940033259A KR0133146B1 (en) | 1994-12-08 | 1994-12-08 | Herbicidal composition |
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