KR950011416B1 - New 2-phemoxypyrimidine derivatives process for preparation thereof and their use as herbicides - Google Patents
New 2-phemoxypyrimidine derivatives process for preparation thereof and their use as herbicides Download PDFInfo
- Publication number
- KR950011416B1 KR950011416B1 KR1019920023691A KR920023691A KR950011416B1 KR 950011416 B1 KR950011416 B1 KR 950011416B1 KR 1019920023691 A KR1019920023691 A KR 1019920023691A KR 920023691 A KR920023691 A KR 920023691A KR 950011416 B1 KR950011416 B1 KR 950011416B1
- Authority
- KR
- South Korea
- Prior art keywords
- group
- formula
- compound
- solvent
- methoxy
- Prior art date
Links
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
- C07D239/02—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings
- C07D239/24—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members
- C07D239/28—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to ring carbon atoms
- C07D239/46—Two or more oxygen, sulphur or nitrogen atoms
- C07D239/60—Three or more oxygen or sulfur atoms
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
Abstract
Description
본 발명은 하기 일반식(I)의 신규한 2-페녹시피리미딘 유도체, 그의 제조방법 및 제초제로서의 그의 용도에 관한 것이다.The present invention relates to novel 2-phenoxypyrimidine derivatives of the following general formula (I), their preparation and their use as herbicides.
[일반식 1][Formula 1]
상기식에서, R1은 수소, 또는 C1-C4알콕시기를 나타내고,R2는 C1-C4알킬기, 페닐기 또는 아세틸기를 나타내며 ; R3는 C1-C4알킬기를 나타낸다.In the above formula, R 1 represents hydrogen or a C 1 -C 4 alkoxy group, and R 2 represents a C 1 -C 4 alkyl group, a phenyl group or an acetyl group; R 3 represents a C 1 -C 4 alkyl group.
본 발명과 유사한 구조를 갖는 화합물들에 대한 선행 특허로서, 유럽 공개특허 제 223,406호, 제287,072호, 제 34, 678호 및 제 402,751호 등이 있는데, 이들 명세서에는 상기 일반식 (I)에서 R2가 수소원자이고,R1이 수소원자 또는 할로겐 원자인 화합물이 보고되어 있으며, R2가 메틸이고,R1이 페닐인 화합물에 대해서도 기재되어 있다.As prior patents for compounds having a structure similar to the present invention, there are European Patent Publication Nos. 223,406, 287,072, 34, 678 and 402,751, and the like. Compounds in which divalent hydrogen atoms, R 1 is hydrogen atoms or halogen atoms have been reported, and R 2 is methyl and R 1 is phenyl.
그러나, 상기 정의된 일반식(I) 화합물들, 보다 구체적으로는, 예컨데 R2가 메틸기이고 동시에 R1이 알콕시기인 화합물에 대해서는 기재되어 있지 않으며, 특히 R2가 에틸기, 아세틸기, 페닐기인 화합물들에 대해서도 또한 언급되어 있지 않다.However, the compounds of general formula (I) as defined above are more specifically described, for example compounds in which R 2 is a methyl group and at the same time R 1 is an alkoxy group, in particular compounds in which R 2 is an ethyl group, an acetyl group, a phenyl group Is also not mentioned.
본 발명은 제초제로서 유용한 하기 일반식(I)의 신규한 2-페녹시 피리미딘 유도체를 제공한다.The present invention provides novel 2-phenoxy pyrimidine derivatives of the general formula (I) below which are useful as herbicides.
[일반식 1][Formula 1]
상기식에서, R1,R2및 R3은 각각 상기 언급한 의미를 갖는다.In the above formula, R 1 , R 2 and R 3 each have the aforementioned meaning.
본 발명에서 일반식(I)의 2-페녹시피리미딘 유도체는 R1이 수소, 메톡시 또는 에톡시기이고, R2가 에틸기, 페닐기 또는 아세틸기인 것이 바람직하다. 특히 바람직하게는 1-(메톡시 카르보닐)에틸 2-(4, 6-디메톡시피리미딘-2-일)옥시-6-메톡시벤조에이트, 1-(메톡시카르보닐)프로필 6-메톡시-2-(4 ,6-디메톡시피리미딘-2-일)옥시벤조에이트 또는 α-(메톡시 카르보닐)벤질 6-(4, 6-디메톡시피리미딘-2-일)옥시벤조에이트 인 일반식(I) 화합물이다.In the present invention, the 2-phenoxypyrimidine derivative of the general formula (I) preferably has R 1 being a hydrogen, methoxy or ethoxy group, and R 2 is an ethyl group, a phenyl group or an acetyl group. Especially preferably 1- (methoxy carbonyl) ethyl 2- (4, 6-dimethoxypyrimidin-2-yl) oxy-6-methoxybenzoate, 1- (methoxycarbonyl) propyl 6- Methoxy-2- (4,6-dimethoxypyrimidin-2-yl) oxybenzoate or α- (methoxy carbonyl) benzyl 6- (4, 6-dimethoxypyrimidin-2-yl) It is a general formula (I) compound which is oxybenzoate.
본 발명에 따른 일반식(I)의 화합물은 하기 반응식(1)에 따라 하기 일반식(II)의 화합물은 실온 내지 120℃의 온도에서 적당한 염기 및 용매의 존재하에 하기 일반식(III)의 화합물과 1 내지 24시간동안 반응시킴으로써 제조할 수 있다.The compound of formula (I) according to the present invention is a compound of formula (II) according to the following reaction formula (1) is a compound of formula (III) in the presence of a suitable base and solvent at a temperature of room temperature to 120 ℃ It can be prepared by reacting with for 1 to 24 hours.
상기식에서, R1,R2및 R3는 상기 언급한 의미를 가지며, X는 할로겐원자(바람직하게는 염소원자), 메틸술포닐옥시기 또는 벤질 술포닐옥시기를 나타낸다.Wherein R 1 , R 2 and R 3 have the meanings mentioned above and X represents a halogen atom (preferably a chlorine atom), a methylsulfonyloxy group or a benzyl sulfonyloxy group.
반응식에서(1)에서 사용될수 있는 염기로는 정량의 수소화나트륨, 수소화칼륨, 탄산수소나트륨, 탄산수소칼륨, 탄산나트륨, 탄산칼륨 등이 바람직하며 이중에서도 탄산칼륨이 특히 바람직하다. 사용될 수 있는 용매로는 테트라히드로 푸란, 1-4-디옥산, 디메틸포름아미드, 디메틸아세트아미드, 디클로로 메탄, 벤젠 등이 있으며,이중 디메틸포름아미드가 바람직하다.Preferred bases that can be used in (1) in the reaction scheme are quantitative sodium hydride, potassium hydride, sodium hydrogen carbonate, potassium hydrogen carbonate, sodium carbonate, potassium carbonate and the like, of which potassium carbonate is particularly preferred. Solvents that may be used include tetrahydrofuran, 1-4-dioxane, dimethylformamide, dimethylacetamide, dichloromethane, benzene and the like, of which dimethylformamide is preferred.
본 발명에 따른 일반식(I)의 화합물은, 또한 하기 반응식(2)에 따라 화합물(IV)와 화합물(III)을 적당한 염기 및 용매의 존재하에 실온에서 1 내지 24시간동안 반응시켜 화합물(V)을 합성한 후 이를 다시 화합물(VI)가 염기 및 용매 존재하에서 실온 내지 120℃의 온도로 반응시켜 제조할 수도 있다.The compound of formula (I) according to the present invention is further reacted with compound (V) by reacting compound (IV) and compound (III) at room temperature for 1 to 24 hours in the presence of a suitable base and a solvent according to Scheme (2) ) May be prepared by reacting Compound (VI) at a temperature of room temperature to 120 ° C. in the presence of a base and a solvent.
상기식에서, R1,R2, R3및 X는 상기 언급한 의미를 가지며, Y는 염소원자, 메틸술포닐기, 벤질 술포닐기이다.Wherein R 1 , R 2 , R 3 and X have the meanings mentioned above and Y is a chlorine atom, methylsulfonyl group, benzyl sulfonyl group.
이 반응식(2)에서 사용되는 염기로서는 정량의 탄산나트륨, 탄산수소나트륨 등이 적당하고, 용매로는 전자의 반응에는 디메틸포름아미드, 디메틸아세틸아미드 등이 적당하며, 후자의 용매는 테트라히드로푸란, 디클로로메탄, 에틸메틸케톤, 벤젠, 또는 디메틸포름아미드등이 바람직하다.As the base used in the reaction formula (2), quantitative sodium carbonate, sodium hydrogen carbonate and the like are suitable, and as the solvent, dimethylformamide, dimethylacetylamide, and the like are suitable for the reaction of the former, and the latter solvent is tetrahydrofuran, dichloro Methane, ethyl methyl ketone, benzene, or dimethylformamide are preferable.
본 발명에서는 출발물질로 사요되는 화합물(IV)는 공지의 물질로서 문현[J. Org. Chem., 27, 3551(1962) 또는 J. Med. Chem., 31, 1039(1988)]등에 기재된 방법에 의하여 용이하게 합성할 수 있다.Compound (IV) used as a starting material in the present invention is known as a known material [J. Org. Chem., 27, 3551 (1962) or J. Med. Chem., 31, 1039 (1988)] and the like can be easily synthesized.
이하, 본 발명은 실시예에 의거하여 더욱 구체적으로 설명하면 다음과 같다.Hereinafter, the present invention will be described in more detail based on Examples.
제조예 1; α-(메톡시카르보닐)벤질 살리실레이트의 제조방법 살리실 산(1.4g)과 메틸 α-브로모페닐아세테이트(2.3g)에 탄산칼륨(1.4g) 및 디메틸포름아미드(30ml)를 첨가한 후 실온에서 6시간동안 교반한다. 교반후 에틸에테르(100ml)를 첨가하고 물로 세척한다. 유기층을 본리한 후 무수망초로 탈숴시키고 여과한 다음 감압증발시켜 잔사를 수득하고 칼럼크로마토그래피를 이용하여 분리 정제시켜 상기 목적 화합물을 80%(1.3g)의 수율로 수득한다.Preparation Example 1; Preparation of α- (methoxycarbonyl) benzyl salicylate Potassium carbonate (1.4 g) and dimethylformamide (30 ml) are added to salicylic acid (1.4 g) and methyl α-bromophenyl acetate (2.3 g). After stirring at room temperature for 6 hours. After stirring, ethyl ether (100 ml) was added and washed with water. The organic layer was isolated, desorbed with anhydrous forget-me-not, filtered and evaporated under reduced pressure to obtain a residue, which was purified by column chromatography to obtain the target compound in a yield of 80% (1.3 g).
1H NMR(CDCl3) :3.73(s, 3H), 6.28(s, 1H), 6.91(t,1H), 6.98(d, 1H), 1 H NMR (CDCl 3 ): 3.73 (s, 3H), 6.28 (s, 1H), 6.91 (t, 1H), 6.98 (d, 1H),
7.38(brs, 5H), 7.50(t,1H)7.38 (brs, 5H), 7.50 (t, 1H)
7.95(d, 1H), 10,49(s, 1H)7.95 (d, 1H), 10,49 (s, 1H)
실시예 1 : 1-(메톡시 카르보닐)에틸 2-(4, 6-디메톡시피리미딘-2-일)옥시-6-메톡시벤조에이트(3)의 제조방법Example 1 Preparation of 1- (methoxycarbonyl) ethyl 2- (4, 6-dimethoxypyrimidin-2-yl) oxy-6-methoxybenzoate (3)
2-(4, 6-디메톡시피리미딘-2-일)옥시-6-메톡시벤조산(3.1g),메틸 2-브로모 프로피오네이트(1,7g) 및 탄산칼륨(1.4g)의 화합물에 디메틸포름 아미드(50ml)를 가하고 실온에서 12시간동안 교반한다. 교반후 용매를 감압증류에 의해 제거하고 에틸아세테이트 100ml를 첨가한후 물로 세척한다. 분리한 유기층을 무수망초로 건조시키고 용매를 감압증류한 후 컬럼 크로마토그래피하여 상기 목적 화합물을 80%(3.1g)의 수율로 수득한다.Of 2- (4,6-dimethoxypyrimidin-2-yl) oxy-6-methoxybenzoic acid (3.1 g), methyl 2-bromo propionate (1,7 g) and potassium carbonate (1.4 g) Dimethylformamide (50 ml) is added to the compound and stirred at room temperature for 12 hours. After stirring, the solvent was removed by distillation under reduced pressure, and 100 ml of ethyl acetate was added, followed by washing with water. The separated organic layer was dried over anhydrous forget-me-not, the solvent was distilled under reduced pressure, and column chromatography was carried out to obtain the target compound in a yield of 80% (3.1 g).
1H NMR(CDCl3) :1.37(d, 3H), 3.68(s, 3H), 3.79(s,6H), 3.87(s, 3H), 1 H NMR (CDCl 3 ): 1.37 (d, 3H), 3.68 (s, 3H), 3.79 (s, 6H), 3.87 (s, 3H),
5.19(q, 1H), 5.74(s,1H),6.87(d, 2H), 7,38(t, 1H)5.19 (q, 1H), 5.74 (s, 1H), 6.87 (d, 2H), 7,38 (t, 1H)
실시예 2 : α-(메톡시카르보닐)벤젠 6-(4, 6-디메톡시피리미딘-2-일)옥시 벤조에이트(9)의 제조방법Example 2 Preparation of α- (methoxycarbonyl) benzene 6- (4,6-dimethoxypyrimidin-2-yl) oxy benzoate (9)
α-(메톡시카르보닐)벤진 살리실레이트(2.9g),4 6-디메톡시-2-메틸술포닐 피리미딘(2.2g)와 탄산칼륨(1.4g)의 혼합물에 디메틸케톤(30ml)을 가하고 12시간동안 환류시킨다. 에틸아세테이트(50ml)를 첨가한후 포화염수로 세척하고, 무수망초로 탈수시킨 다음 용매를 감압제거하여 상기 목적화합물을 90%(4.1g)의 수율로 수득한다.To a mixture of α- (methoxycarbonyl) benzine salicylate (2.9 g), 4 6-dimethoxy-2-methylsulfonyl pyrimidine (2.2 g) and potassium carbonate (1.4 g) was added dimethyl ketone (30 ml). And reflux for 12 hours. Ethyl acetate (50 ml) was added, washed with saturated brine, dehydrated with anhydrous forget-me-not and the solvent was removed under reduced pressure to obtain the target compound in a yield of 90% (4.1 g).
1H NMR(CDCl3) :3.72(s, 3H), 3.76(s, 6H), 5.69(s,1H), 5.59(s, 1H), 1 H NMR (CDCl 3 ): 3.72 (s, 3H), 3.76 (s, 6H), 5.69 (s, 1H), 5.59 (s, 1H),
7.35(brs, 5H), 7.62(t,1H),8.12(d, 1H)7.35 (brs, 5H), 7.62 (t, 1H), 8.12 (d, 1H)
실시예 3:1-(메톡시카르보닐)프로필 6-메톡시-2-(4, 6-디메톡시 피리미딘-2-일)옥시벤조에이트(7)의 제조방법Example 3: Preparation of 1- (methoxycarbonyl) propyl 6-methoxy-2- (4, 6-dimethoxy pyrimidin-2-yl) oxybenzoate (7)
1-(메톡시카르보닐)프로필 6-메톡시-2-히드록시 벤조에이트(2.8g), 4, 6- -디메톡시-2-메틸 술포닐 피리미딘(2.2g)과 탄산칼륨(1.4g)의 혼합물에 디메틸포름아미드(20ml)를 가하고 실온에서 12시간동안 교반한다. 교반후 에틸 아세테이트(50ml)를 첨가하고 포화염수로 세척한 후, 무수망초로 탈수시키고 용매를 감압제거하여 상기 목적 화합물을 90%(4.0g)의 수울로 수득한다.1- (methoxycarbonyl) propyl 6-methoxy-2-hydroxy benzoate (2.8 g), 4, 6-dimethoxy-2-methyl sulfonyl pyrimidine (2.2 g) and potassium carbonate (1.4 g Dimethylformamide (20 ml) is added to the mixture of and stirred at room temperature for 12 hours. After stirring, ethyl acetate (50 ml) was added, washed with saturated brine, dehydrated with anhydrous forget-me-not and the solvent was removed under reduced pressure to obtain the target compound as a 90% (4.0 g) suspension.
1H NMR(CDCl3) :0.88(t 3H), 1.80(m, 2H), 3.69(s,3H), 3.78(s, 6H), 1 H NMR (CDCl 3 ): 0.88 (t 3H), 1.80 (m, 2H), 3.69 (s, 3H), 3.78 (s, 6H),
3.85(s, 3H), 5.09(t,1H),5.72(s, 1H), 6,82(d, 2H),7.39(t,1H)3.85 (s, 3H), 5.09 (t, 1H), 5.72 (s, 1H), 6,82 (d, 2H), 7.39 (t, 1H)
하기 표1에는 상기 실시예와 유사한 방법으로 수득할 수 있는 본 발명의 2-페녹시피리미딘 유도체의 대표적인 예를 나타내었다.Table 1 below shows representative examples of the 2-phenoxypyrimidine derivatives of the present invention which can be obtained by a method similar to the above examples.
[일반식 1][Formula 1]
[표 1]TABLE 1
본 발명에서는 합성된 2-페녹시 피리미딘 유도체의 제초효력을 검정하기 위하여 온실에서 검정식물을 포트 재배 및 처리방법으로 수행하였고 효력판정은 약효 및 약해 평가기준(표2)에 따라 달관평가를 하였다.In the present invention, in order to test the herbicidal efficacy of the synthesized 2-phenoxy pyrimidine derivative, potted plants were tested by pot cultivation and treatment method in the greenhouse, and the efficacy was evaluated by the efficacy and weakness evaluation criteria (Table 2). .
효력 검정식물로서 밭 잡초는 바랭이(Digitaria sanguinalis), 강아지풀(Sataria farberi), 돌피(Echinochloa crus-galli var. caudata), 수수(Sorghum bicolor), 자귀풀(Aeschynomene indica), 까마중(Solanum nigrum), 어저귀(Abutilon theophrasti), 메꽃(Calystergia japonica)을 ; 논잡초는 강피(Echinochloa crus-gall var. oryzicola), 사마귀풀(Aneilema keisak), 올챙이 고랭이(Scirpus juncoides), 물달개비(Monochoria vaginalis), 올방개(Eleocharis kuroguwai), 너도방동산이(Cyperus serotinus), 올미(Sagittaria pygmaea)등이었다.Field test Weeds include Digitaria sanguinalis, Sataria farberi, Echinochloa crus-galli var.caudata, Sorghum bicolor, Aeschynomene indica, Solanum nigrum Abutilon theophrasti, Calystergia japonica; Paddy weeds are Echinochloa crus-gall var.oryzicola, Mantis grass (Aneilema keisak), Tadpole (Scirpus juncoides), Swallowtail (Monochoria vaginalis), Olga (Eleocharis kuroguwai), Cyperus serotin And Sagittaria pygmaea.
본 발명의 화합물은 점토, 활석, 규조토중등의 고형 물질 및 물, 알콜, 벤젠, 틀루엔, 에테르, 케톤류, 에스텔류, 산류, 아미드류 등의 액체 물질과 혼용함으로써 액체, 유제, 수화제, 분제, 입제등과 같은 임의의 제형으로 조제하여 사용할 수 있으며, 필요에 따라 유화제, 분산제, 침투제, 전착제, 안정제를 첨가할 수 있다.Compounds of the present invention are mixed with solid materials such as clay, talc, diatomaceous earth and liquid materials such as water, alcohols, benzene, toluene, ethers, ketones, esters, acids, amides, liquids, emulsions, wetting agents, powders, It can be prepared in any formulation such as granules and the like, and emulsifiers, dispersants, penetrants, electrodeposition agents, stabilizers can be added as necessary.
다음은 본 발명 화합물은 유효 성분으로 하는 제초제의 배합예를 일부 나타냈지만 이러한 방법만으로 한정시킬 필요는 없다.Next, although the compound of this invention showed some compounding examples of the herbicide which makes an active ingredient, it does not need to limit only to this method.
[배합예 1(발조건, 0.5kg/ha)][Compound Example 1 (Bal condition, 0.5kg / ha)]
본 발명 화합물 40mg을 유기용매(아세톤)160㎖에 용해시킨 후 비이온성 계면활성제 트윈-20이 0.2%함유된 160㎖에 희석시킨다.40 mg of the compound of the present invention was dissolved in 160 ml of an organic solvent (acetone) and then diluted in 160 ml of 0.2% of nonionic surfactant Tween-20.
[배합예 2(논조건, 0.5kg/ha)][Combination Example 2 (Paper Condition, 0.5kg / ha)]
본 발명 화합물 40mg을 유기용매(아세톤) 80㎖에 용해시킨 후 비이온성 계면활성제 트윈-20이 0.2%함유된 증류수 80㎖에 희석시킨다.40 mg of the compound of the present invention was dissolved in 80 ml of an organic solvent (acetone) and then diluted in 80 ml of distilled water containing 0.2% of the nonionic surfactant Tween-20.
[표 2]TABLE 2
[실험예 1]Experimental Example 1
토양처리에 의한 발아전 제초효력 검정(밭조건)Analysis of herbicidal efficacy before germination by soil treatment (field conditions)
4각 포토(21.5 × 15.5 × 7.0cm)에 살균처리한 발토양(사질양토, pH 5.5-6.0)을 충진하여 표면적 300㎠인 상태에서 밭 잡초 8초종을 두 포트에 파종하고 0.5cm 복토한다. 관수 1일후 상기 배합예의 용액에서 처리 약량(0.5kg/ha)에 해당하는 유효성분을 함유한 용액 일부(12㎖/pot)를 토양표면에 균일하게 살포하고 4주동안 재배 및 관찰한 후 작물의 약해 및 잡초에 대한 제초효과를 판정기준에 따라 달관 평가하였다. 결과표를 하기 표3에 나타내었다.Fill the quadruple photo (21.5 × 15.5 × 7.0 cm) with sterilized foot soil (sand loam, pH 5.5-6.0) and plant 8 weeds in two fields with a surface area of 300 cm 2 and cover 0.5 cm. After 1 day of irrigation, the solution of the above compounded example (12 ml / pot) containing the active ingredient (0.5 kg / ha) was evenly sprayed on the soil surface and grown and observed for 4 weeks. The herbicidal effects on weeds and weeds were assessed according to the criteria. The result table is shown in Table 3 below.
[표 3]TABLE 3
[실험예 2]Experimental Example 2
경엽처리에 의한 발아후 제초효력 검정(밭조건)Herbicide efficacy test after germination by foliage treatment (field conditions)
실험예 1과 동일한 방법으로 파종한 후 10 내지 14일 재배하여 식물체가 3 내지 4 엽기에 이르면 소정의 유효성분(0.5kg/ha)을 함유하는 배합된 용액(12㎖/pot)을 식물체 경엽부위에 균일하게 살포처리한 후 4주일 동안 재배 관리 및 관찰하여 제초효력 판정기준에 따라 달관평가 하였다. 결과표를 하기 표4에 나타내었다.After seeding in the same manner as in Experimental Example 1 and cultivating for 10 to 14 days, when the plant reaches the 3 to 4 foliar phase, a mixed solution (12 ml / pot) containing a predetermined active ingredient (0.5 kg / ha) was planted at the plant foliage area. After spreading uniformly to the cultivation management and observation for 4 weeks was evaluated by the herbicidal efficacy criteria. The result table is shown in Table 4 below.
[표 4]TABLE 4
[실험예 3]Experimental Example 3
토양처리에 의한 발아전 제초효력 검정(논조건)Analysis of herbicidal efficacy before germination by soil treatment (field conditions)
4각 포트(30 ×15cm)에 살균한 논토양(식양토, pH 5.5 내지 6.0)을 충진하고 표면적 450㎠인 상태에서 논잡초 7초종을 파종하고 토중 혼입한다. 4cm의 관수 1일후 소정의 유효성분(0.5kg/ha)를 함유하는 상기 논조건의 배합된 용액일부(8㎖/포트)를 점적처리한다. 처리후 4주 동안 재배관리 및 관찰한 후 벼에 대한 약해 및 잡초에 대한 제초효과를 판정기준에 따라 달관 평가하였다. 결과표를 하기 표5에 나타내었다.Filled with sterilized paddy soil (plant soil, pH 5.5 to 6.0) in each of the four pots (30 x 15 cm), sowing 7 weeds of nonweed weeds in a state of surface area of 450 cm 2 and mixed in soil. After one day of watering of 4 cm, a portion of the above-mentioned combined solution (8 ml / pot) containing a predetermined effective ingredient (0.5 kg / ha) is dipped. After 4 weeks of treatment and cultivation management and observation, herbicide effects on weeds against weeds and weeds were evaluated according to the criteria. The result table is shown in Table 5 below.
[표 5]TABLE 5
Claims (5)
Priority Applications (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
KR1019920023691A KR950011416B1 (en) | 1992-12-09 | 1992-12-09 | New 2-phemoxypyrimidine derivatives process for preparation thereof and their use as herbicides |
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
KR1019920023691A KR950011416B1 (en) | 1992-12-09 | 1992-12-09 | New 2-phemoxypyrimidine derivatives process for preparation thereof and their use as herbicides |
Publications (2)
Publication Number | Publication Date |
---|---|
KR940014354A KR940014354A (en) | 1994-07-18 |
KR950011416B1 true KR950011416B1 (en) | 1995-10-04 |
Family
ID=19345031
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
KR1019920023691A KR950011416B1 (en) | 1992-12-09 | 1992-12-09 | New 2-phemoxypyrimidine derivatives process for preparation thereof and their use as herbicides |
Country Status (1)
Country | Link |
---|---|
KR (1) | KR950011416B1 (en) |
-
1992
- 1992-12-09 KR KR1019920023691A patent/KR950011416B1/en not_active IP Right Cessation
Also Published As
Publication number | Publication date |
---|---|
KR940014354A (en) | 1994-07-18 |
Similar Documents
Publication | Publication Date | Title |
---|---|---|
KR950011416B1 (en) | New 2-phemoxypyrimidine derivatives process for preparation thereof and their use as herbicides | |
KR0131528B1 (en) | Novel pyrimidine derivatives, process for preparation thereof and use thereof as herbicide | |
KR950011417B1 (en) | New 2-phemoxypyrimidine derivatives and process for preparation thereof | |
KR960000049B1 (en) | 2-phenoxy pyrimidin derivatives having tetrahydropyranyl radical and method of preparing them | |
KR0174374B1 (en) | Herbicidal pyrimidine compound having benzophenoneoxime ester and process for preparation thereof | |
KR0120270B1 (en) | New weeding pyrimidine derivatives having phenyliminoester structure, process for preparing thereof and the weeding composition containing it | |
KR970001479B1 (en) | 2-(pyrimidin-2-yl) oxyacetophenone derivatives useful as a herbicide and process for preparation thereof | |
KR0120271B1 (en) | NEW WEEDING PYRIMIDINE DERIVATIVES HAVING Ñß-CARBONYL-IMINO STRUCTURE, PROCESS FOR PREPARING THEREOF AND THE WEEDIN COMPOSITION CONTAINING IT | |
KR100218195B1 (en) | 5-(4,6-dimethoxypyrimidin-2-yl)oxy-4h-(1,3)-benzodioxin-4one derivatives and process for the preparation thereof | |
KR0174375B1 (en) | Herbicidal pyrimidine derivatives having tricyclic ketone oxime ester and process for preparation thereof | |
KR0131531B1 (en) | Novel herbicidal triazole derivatives | |
KR960012180B1 (en) | Novel phenyliminoester derivative of 6-chloro-2-(4,6-dimethoxy pyrinidine-2-yl)oxybenjoic acid and process for preparation thereof | |
KR0163293B1 (en) | Substituted 5-(4,6-dimethoxyprimidin-2-yl)oxy-4h-[1,3]-benzodioxin-4-one derivatives, process for preparation thereof and its using as herbicide | |
KR100345852B1 (en) | 1-benzyl-4,5-dicarbonyl-1,2,3-triazole derivatives and preparation process thereof | |
KR960012181B1 (en) | Novel heteroarylimino ester derivative of 6-chloro-2-(4,6-dimethoxypyrimidine-2-yl)oxybenzoic acid and process for preparation thereof | |
KR960012195B1 (en) | NOVELÑß-NITRILEIMINO ESTER DERIVATIVE OF 6-CHLORO-2-(4.6-DIMETHOXYPYRIMIDINE-2-YL)OXYBENZIC ACID AND PROCESS FOR PREPARATION THEREOF | |
JP2809481B2 (en) | 2-Alkoxycarbonyl-3-pyridinecarboxylic acid derivatives, their production and herbicides | |
KR0129601B1 (en) | Novel herbicidal triagole derivatives | |
KR100256548B1 (en) | Novel fluoropropenyloxyacetamide and process for the preparation thereof | |
KR970001481B1 (en) | 2-(4,6-dimethoxy pyrimidin-2-yl) oxyacetophenone derivative, process for preparation thereof and use thereof as a herbicide | |
KR960003323B1 (en) | NOVEL HERBICIDAL PYRIMIDIN DERIVATIVES HAVING Ñß-CARBONYLIMINO STRUCTURE, THE PROCESS FOR PREPARATION THEREOF AND THE HERBICIDES CONTAING THE SAME | |
KR100345853B1 (en) | 1,2,3-Triazole-4-carboxylic acid derivative and process for preparation thereof | |
KR100345849B1 (en) | 1-Benzyl-1,2,3-triazolecarboxylic acid derivative and process for preparation thereof | |
KR0133147B1 (en) | New pyridinyloxyphenoxypropionate derivatives | |
KR100342949B1 (en) | Erythritol derivatives having herbicidal activity and preparation process thereof |
Legal Events
Date | Code | Title | Description |
---|---|---|---|
A201 | Request for examination | ||
E902 | Notification of reason for refusal | ||
G160 | Decision to publish patent application | ||
E701 | Decision to grant or registration of patent right | ||
GRNT | Written decision to grant | ||
FPAY | Annual fee payment |
Payment date: 19980925 Year of fee payment: 4 |
|
LAPS | Lapse due to unpaid annual fee |