KR0163591B1 - Uracil derivatives and herbicides containing the same as active ingredient - Google Patents

Uracil derivatives and herbicides containing the same as active ingredient Download PDF

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KR0163591B1
KR0163591B1 KR1019900010635A KR900010635A KR0163591B1 KR 0163591 B1 KR0163591 B1 KR 0163591B1 KR 1019900010635 A KR1019900010635 A KR 1019900010635A KR 900010635 A KR900010635 A KR 900010635A KR 0163591 B1 KR0163591 B1 KR 0163591B1
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준 사또
겐조 후꾸다
가오루 이또
고이찌 스즈끼
쯔또무 나와마끼
시게오미 와따나베
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나까이 다께오
닛산 가가꾸 고교 가부시끼가이샤
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    • C07D239/00Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
    • C07D239/02Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings
    • C07D239/24Heterocyclic 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
    • C07D239/28Heterocyclic 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
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    • AHUMAN NECESSITIES
    • A01AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01NPRESERVATION 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
    • A01N43/00Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/48Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with two nitrogen atoms as the only ring hetero atoms
    • A01N43/541,3-Diazines; Hydrogenated 1,3-diazines
    • AHUMAN NECESSITIES
    • A01AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01NPRESERVATION 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
    • A01N43/00Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/72Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms
    • A01N43/82Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms five-membered rings with three ring hetero atoms
    • AHUMAN NECESSITIES
    • A01AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01NPRESERVATION 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
    • A01N43/00Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/72Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms
    • A01N43/84Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms six-membered rings with one nitrogen atom and either one oxygen atom or one sulfur atom in positions 1,4
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    • C07D403/04Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings directly linked by a ring-member-to-ring-member bond
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    • C07D413/00Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
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    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D417/00Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
    • C07D417/02Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings
    • C07D417/04Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings directly linked by a ring-member-to-ring-member bond

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Abstract

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Description

우라실 유도체 및 활성성분으로서 이를 함유하는 제초제Uracil derivatives and herbicides containing the same as active ingredients

본 발명은 신규한 우라실 유도체 및 활성성분으로서 우라실 유도체를 함유하는 선택적 제초제에 관한 것이다.The present invention relates to novel uracil derivatives and selective herbicides containing uracil derivatives as active ingredients.

벼, 대두, 밀, 옥수수, 목화, 사탕수수 등과 같은 중요한 농작물을 잡초로부터 보호하고 이들 농작물의 생산성을 높이기 위하여 다양한 제초제를 제조 및 실제 사용해왔다. 제초제는 투여 장소에 따라 하기의 3가지 형으로 크게 분류될 수 있다:(1) 산지 경작용 제초제, (2) 논용 제초제 및 (3) 비경지용 제초제. 각 부류의 제초제는 투여방법에 따라 토양 혼입 처리형, 발아전 처리형 및 발아후 처리(엽면 처리)형 같은 부그룹으로 다시 분류될 수 있다.Various herbicides have been manufactured and used in practice to protect important crops such as rice, soybeans, wheat, corn, cotton, sugarcane, etc. from weeds and increase their productivity. Herbicides can be broadly classified into the following three types according to the place of administration: (1) mountain cultivating herbicides, (2) rice herbicides and (3) parenteral herbicides. Herbicides of each class can be subdivided into subgroups, such as soil incorporation type, pre-germination type and post-germination type (leaf surface treatment) type, depending on the method of administration.

최근 지구상의 인구가 증가하면서, 주식용 농작물의 생산성이 각국의 식량 경계면에 심각한 영향을 끼쳐 이제 주식용 농작물의 생산성 향상이 특히 중요한 문제로 대두됨을 부인할 수 없다. 실제로, 농업에 종사하는 사람들에게는 농작물의 경작에 해를 끼치는 잡초를 죽이거나 또는 잡초의 생장을 조절하는데 효과적이며 경제적인 제초제를 개발하는 것이 더욱 필요하다.With the recent increase in the global population, it is undeniable that the productivity of stock crops has seriously affected the food boundaries of each country, and the productivity improvement of stock crops is now a particularly important issue. Indeed, there is a greater need for people in agriculture to develop effective and economical herbicides to kill weeds or to control the growth of weeds that are harmful to the cultivation of crops.

이러한 제초제로서, 하기 조건을 만족시킬 수 있는 것이 요구된다:(1) 적은 투여량으로도 제초 효과가 높다.(특히 환경 보호의 관점에서 가능한한 소량의 제초제를 투여하여 잡초를 죽일 수 있어야 한다.)As such herbicides, it is required to be able to satisfy the following conditions: (1) The herbicidal effect is high even at a small dose. (In particular, from the viewpoint of environmental protection, weeds should be able to kill small amounts of herbicide as much as possible. )

(2) 잔류 효과가 적절하다.(최근, 토양에서 장기간동안 그 효과를 유지하는 화학약품으로 인해 다음번의 농작물이 해를 입을 수 있다는 문제점이 지적되었다. 따라서 화학약품이 투여후 적절한 잔류 효과를 유지하는 것이 중요하다.)(2) Residual effects are adequate. (Recently, it has been pointed out that the chemicals that maintain their effects for a long time in the soil may cause the next crop to be harmed. It is important to do that.)

(3) 투여후 잡초가 빨리 죽는다.(화학약품 처리후 단시간내에 다음번 농작물을 파종 및 이식할 수 있다.)(3) Weeds die quickly after administration. (The next crop can be sown and transplanted within a short time after chemical treatment.)

(4) 제초제 처리(투여)를 해야하는 횟수가 적다.(농부들에게는 잡초-방제 작업의 횟수가 최소화되어야 하는 것이 중요하다.)(4) Fewer herbicide treatments (administration). (It is important for farmers to minimize the number of weed-control operations.)

(5) 1종의 제초제에 의해 죽거나 또는 억제되는 잡초가 광범위하다.(1종의 제초제를 투여함으로써 활엽 잡초, 포아풀과의 잡초 및 다년생 잡초 같은 상이한 잡초를 죽이거나 억제할 수 있는 것이 바람직하다.)(5) The weeds that are killed or suppressed by one herbicide are widespread. (The administration of one herbicide is preferred to be able to kill or suppress different weeds such as broadleaf weeds, weeds with poapools and perennial weeds. )

(6) 투여방법이 다양하다.(토양 처리, 엽면 처리 등과 같은 다양한 방식으로 투여할 수 있는 경우 제초효과가 강화된다.)(6) There are various methods of administration. (If the method can be administered in various ways such as soil treatment, foliar treatment, etc., the herbicidal effect is enhanced.)

(7) 농작물에 피해가 없다.(농작물과 잡초가 공존하는 경작지에서는 잡초만이 제초제에 의해 선택적으로 죽는 것이 바람직하다.)(7) There is no damage to crops. (In farmland where crops and weeds coexist, it is preferable that only weeds are selectively killed by herbicides.)

그러나, 상기 조건을 모두 만족시킬 수 있는 제초제는 아직 없다.However, no herbicides can satisfy all of the above conditions.

우라실 유도체중 일부 화합물에 제초활성이 있다는 것이 공지되어 있다. 예를 들어, Pesticide Manual, 8판, 89페이지(The British Crop Protection Council, 1987)에는 우라실 구조를 갖는 제초제로서 브로마실이 기재되어 있다.It is known that some compounds in uracil derivatives have herbicidal activity. For example, the Pesticide Manual, 8th edition, page 89 (The British Crop Protection Council, 1987) describes bromasil as a herbicide with uracil structure.

또한 제초제용 활성성분으로서 제공될 수 있는 하기 헤테로-고리 유도체도 공지되어 있다:Also known are the following hetero-ring derivatives which may serve as active ingredients for herbicides:

(1) 하기 일반식의 3-아릴우라실-알킬, 알켄일 및 알킨일에놀에테르(일본국 특허 공개 63-107967호):(1) 3-aryluracil-alkyl, alkenyl and alkynylenol ethers of the following general formula (Japanese Patent Laid-Open No. 63-107967):

Figure kpo00000
Figure kpo00000

상기 식에서, R1은 C1-8알킬, C2-6알켄일, C2-6알킨일, C2-8알콕시알킬 또는

Figure kpo00001
이고, R2는 할로겐 또는 시아노이고, R3은 수소 또는 할로겐이며, R4는 수소, 플루오르 또는 C1-4알킬이고, R5는 C1-4알킬 또는 C1-4할로알킬이며, 또는 R4와 R5는 함께 트리-또는 테트라-메틸렌일 수 있고, R6과 R7은 독립적으로 C1-4알킬이고, m은 1 또는 2이며, X는 O, O-C(O), O-C(O)-O 또는 C(O)-O이다.Wherein R 1 is C 1-8 alkyl, C 2-6 alkenyl, C 2-6 alkynyl, C 2-8 alkoxyalkyl or
Figure kpo00001
R 2 is halogen or cyano, R 3 is hydrogen or halogen, R 4 is hydrogen, fluorine or C 1-4 alkyl, R 5 is C 1-4 alkyl or C 1-4 haloalkyl, Or R 4 and R 5 together may be tri- or tetra-methylene, R 6 and R 7 are independently C 1-4 alkyl, m is 1 or 2, and X is O, OC (O), OC (O) -O or C (O) -O.

(2) 하기 일반식의 화합물 및 R1이 수소인 그의 염(일본국 특허 공개 63-41466호):(2) The compound of the following general formula and its salt whose R <1> is hydrogen (Japanese Patent Laid-Open No. 63-41466):

Figure kpo00002
Figure kpo00002

상기 식에서, R1은 수소, C1-4알킬, C1-4할로알킬, 포르밀 또는 C2-6알칸온일이고, R2는 에테르, 또는 (티오)카르보닐옥시 또는 술폰일옥시를 함유하며 산소 원자를 통해 벤젠핵 A에 직접 결합되는 잔기이고, R3은 할로겐 또는 시아노이며, R4는 수소 또는 할로겐이고, R5는 수소, 할로겐 또는 C1-4알킬이고, R6은 C1-4알킬 또는 C1-4할로알킬이며, 또는 R5와 R6은 함께 트리-또는 테트라메틸렌일 수 있다.Wherein R 1 is hydrogen, C 1-4 alkyl, C 1-4 haloalkyl, formyl or C 2-6 alkanonyl, and R 2 contains ether or (thio) carbonyloxy or sulfonyloxy And a residue directly bonded to benzene nucleus A via an oxygen atom, R 3 is halogen or cyano, R 4 is hydrogen or halogen, R 5 is hydrogen, halogen or C 1-4 alkyl, and R 6 is C 1-4 alkyl or C 1-4 haloalkyl, or R 5 and R 6 together may be tri- or tetramethylene.

(3) 하기 일반식의 벤조티아졸론 유도체(일본국 특허 공개 62-155276호):(3) Benzothiazolone derivatives of the following general formula (Japanese Patent Laid-Open No. 62-155276):

Figure kpo00003
Figure kpo00003

상기 식에서, R은 수소, 저급 알킬, 저급 알켄일, 저급 알킨일, 저급 할로알킬, 저급 할로알케일, 저급 할로알킨일, 저급 알콕시-저급 알킬, 저급 알콕시-저급 알콕시-저급 알킬, 신나밀 또는 저급 시아노알킬이다.Wherein R is hydrogen, lower alkyl, lower alkenyl, lower alkynyl, lower haloalkyl, lower haloalkale, lower haloalkynyl, lower alkoxy-lower alkyl, lower alkoxy-lower alkoxy-lower alkyl, cinnamil or Lower cyanoalkyl.

(4) 하기 일반식의 축합된 헤테로-고리 유도체(일본국 특허 공개 1-250388호):(4) Condensed hetero-ring derivatives of the following general formula (Japanese Patent Laid-Open No. 1-250388):

Figure kpo00004
Figure kpo00004

상기 식에서, X는 산소 원자 또는 황 원자이고, Z는Wherein X is an oxygen atom or a sulfur atom, and Z is

Figure kpo00005
Figure kpo00005

이고, G는 수소원자 또는 할로겐원자이며, A는 할로겐 원자 또는 NO2이고, E는 수소 원자, 할로겐 원자, C≡N, NO2, NH2, OH, SH, OR1이고, R1은 C1-5알킬, C3-6시클로알킬, C3-6시클로알킬-(C1-2)알킬, C2-4알켄일, C3-4알킨일,G is a hydrogen atom or a halogen atom, A is a halogen atom or NO 2 , E is a hydrogen atom, a halogen atom, C≡N, NO 2 , NH 2 , OH, SH, OR 1 , and R 1 is C 1-5 alkyl, C 3-6 cycloalkyl, C 3-6 cycloalkyl- (C 1-2 ) alkyl, C 2-4 alkenyl, C 3-4 alkynyl,

Figure kpo00006
Figure kpo00006

CH2C≡N, 테트라히드로피란일, 테트라히드로티오피란일, CH2COR1e',CH 2 C≡N, tetrahydropyranyl, tetrahydrothiopyranyl, CH 2 COR 1e ' ,

Figure kpo00007
Figure kpo00007

또는 C1-2알콕시-(C1-2)알킬, SR3, CO2R5, NHR6, 또는 CH=NOR7이며, Qa및 Qb는 독립적으로 산소원자 또는 황원자이고, R1a는 수소원자 또는 C1-3알킬이고, R1b는 수소원자, C1-5알킬, C2-5알켄일, C3-5알킨일, C2-3할로알킬, C1-2알콕시-(C1-2)알킬, C3-4시클로알킬-(C1-2)알킬, C3-6시클로알킬, CH2CO2-(C1-3알킬), 또는 CH(CH3)-CO2-(C1-2알킬)이며, 또는 R1a와 R1b는 합쳐져서 메틸렌 사슬로 구성된 4- 내지 6-원 고리 락톤을 형성하고, R1c및 R1d는 독립적으로 수소원자, C1-5알킬, C2-5알켄일, C3-5알킨일, C2-5할로알킬, C3-6시클로알킬 또는 C3-6시클로알킬-(C1-2)알킬이고, 또는 R1d와 R1c는 합쳐져서 메틸렌 사슬로 구성된 5- 내지 7-원 고리를 형성하고, R1e는 C1-3알킬이며, R1f는 수소원자, C1-3알킬, CH2CO2-(C1-3)알킬 또는 COCH3이고, R3은 상기 R1과 동일한 의미를 가지며, R5는 수소원자, C1-5알킬, C3-6시클로알킬 또는 C3-6시클로알킬-(C1-2)알킬이고, R6은 C1-5알킬, C3-6시클로알킬, C3-6시클로알킬-(C1-2)알킬, C2-4알켄일 또는 C3-4알킨일이며, R7은 수소원자, C1-5알킬, C3-6시클로알킬, C3-6시클로알킬-(C1-2)알킬, C2-4알켄일 또는 C3-4알킨일이고, L은 수소원자 또는 할로겐 원자이고, Y는 산소원자 또는 황원자이며, n은 0 또는 1이며, J는 수소원자, 할로겐 원자, C1-5알킬, C3-6시클로알킬, C3-6시클로알킬-(C1-2)알킬, C2-4알켄일, C3-4알킨일, C1-5할로알킬, C3-4할로알켄일, C3-4할로알킨일, C1-2알콕시-(C1-2)알킬, CH2C≡N, CH2CO2R8, 또는 CH2CH2CO2R9이고, R8및 R9는 수소원자, C1-5알킬, C3-6시클로알킬 또는 C3-6시클로알킬-(C1-2)알킬이다.Or C 1-2 alkoxy- (C 1-2 ) alkyl, SR 3 , CO 2 R 5 , NHR 6 , or CH = NOR 7 , Q a and Q b are independently an oxygen atom or a sulfur atom, and R 1a is Hydrogen atom or C 1-3 alkyl, R 1b is hydrogen atom, C 1-5 alkyl, C 2-5 alkenyl, C 3-5 alkynyl, C 2-3 haloalkyl, C 1-2 alkoxy- ( C 1-2 ) alkyl, C 3-4 cycloalkyl- (C 1-2 ) alkyl, C 3-6 cycloalkyl, CH 2 CO 2- (C 1-3 alkyl), or CH (CH 3 ) -CO 2- (C 1-2 alkyl), or R 1a and R 1b combine to form a 4- to 6-membered ring lactone consisting of a methylene chain, and R 1c and R 1d are independently a hydrogen atom, C 1-5 Alkyl, C 2-5 alkenyl, C 3-5 alkynyl, C 2-5 haloalkyl, C 3-6 cycloalkyl or C 3-6 cycloalkyl- (C 1-2 ) alkyl, or R 1d with R 1c combine to form a 5- to 7-membered ring consisting of a methylene chain, R 1e is C 1-3 alkyl, R 1f is a hydrogen atom, C 1-3 alkyl, CH 2 CO 2- (C 1- 3 ) alkyl or COCH 3 , R 3 is a phase Has the same meaning as group R 1 , R 5 is a hydrogen atom, C 1-5 alkyl, C 3-6 cycloalkyl or C 3-6 cycloalkyl- (C 1-2 ) alkyl, R 6 is C 1- 5 alkyl, C 3-6 cycloalkyl, C 3-6 cycloalkyl- (C 1-2 ) alkyl, C 2-4 alkenyl or C 3-4 alkynyl, R 7 is a hydrogen atom, C 1-5 Alkyl, C 3-6 cycloalkyl, C 3-6 cycloalkyl- (C 1-2 ) alkyl, C 2-4 alkenyl or C 3-4 alkynyl, L is a hydrogen atom or a halogen atom, Y is Oxygen atom or sulfur atom, n is 0 or 1, J is hydrogen atom, halogen atom, C 1-5 alkyl, C 3-6 cycloalkyl, C 3-6 cycloalkyl- (C 1-2 ) alkyl, C 2-4 alkenyl, C 3-4 alkynyl, C 1-5 haloalkyl, C 3-4 haloalkenyl, C 3-4 haloalkynyl, C 1-2 alkoxy- (C 1-2 ) alkyl, CH 2 C≡N, CH 2 CO 2 R 8 , or CH 2 CH 2 CO 2 R 9 , R 8 and R 9 are hydrogen atoms, C 1-5 alkyl, C 3-6 cycloalkyl or C 3-6 Cycloalkyl- (C 1-2 ) alkyl.

(5) 하기 일반식의 화합물 및 R1및/또는 R2가 수소인 그의 염(일본국 특허 공개 61-221178호):(5) The compound of the following general formula and its salt whose R <1> and / or R <2> is hydrogen (Japanese Patent Laid-Open No. 61-221178):

Figure kpo00008
Figure kpo00008

상기 식에서, R1은 수소, C1-4알킬, C2-4알켄일, C2-4알킨일, C2-6알콕시알킬, 포르밀, C2-6알카노일 또는 C2-6알콕시카르보닐이고; R2는 수소, C1-6알킬, C2-4알켄일, C2-4알킨일 또는 C2-6알콕시알킬이고; R3은 할로겐 또는 니트로이고; R4는 수소 또는 할로겐이며; R5는 수소, 할로겐, C1-4알킬, 클로로메틸, 브로모메틸, 히드록시메틸, (C1-5알콕시)메틸, (C1-5알킬티오)메틸, 시아노, 니트로 또는 티오시아네이토이고; R6은 수소, C1-4알킬 또는 C1-4플루오로알킬이며, 또는 R5와 R6은 합쳐져서 트리-또는 테트라메틸렌이고, 이때 상기 메틸렌기 중 하나는 산소 또는 황으로 치환될 수 있거나 또는 이들 기는 C1-3알킬로 치환될 수 있으며; X는 산소 또는 황이고, (i) R5가 플루오르인 경우 R6은 C1-4알킬 또는 C1-4플루오로알킬이고, (ii) R5가 시아노인 경우 R6은 수소 또는 C1-4알킬이고 X는 산소이다.Wherein R 1 is hydrogen, C 1-4 alkyl, C 2-4 alkenyl, C 2-4 alkynyl, C 2-6 alkoxyalkyl, formyl, C 2-6 alkanoyl or C 2-6 alkoxy Carbonyl; R 2 is hydrogen, C 1-6 alkyl, C 2-4 alkenyl, C 2-4 alkynyl or C 2-6 alkoxyalkyl; R 3 is halogen or nitro; R 4 is hydrogen or halogen; R 5 is hydrogen, halogen, C 1-4 alkyl, chloromethyl, bromomethyl, hydroxymethyl, (C 1-5 alkoxy) methyl, (C 1-5 alkylthio) methyl, cyano, nitro or thiooxy Anatomic; R 6 is hydrogen, C 1-4 alkyl or C 1-4 fluoroalkyl, or R 5 and R 6 combined are tri- or tetramethylene, wherein one of the methylene groups may be substituted with oxygen or sulfur Or these groups may be substituted with C 1-3 alkyl; X is oxygen or sulfur, (i) R 6 is C 1-4 alkyl or C 1-4 fluoroalkyl when R 5 is fluorine, and (ii) R 6 is hydrogen or C 1 when R 5 is cyano -4 alkyl and X is oxygen.

(6) 하기 일반식의 테트라히드로프탈이미드 유도체(일본국 특허 공개 61-85385호):(6) Tetrahydrophthalimide derivatives of the following general formula (Japanese Patent Laid-Open No. 61-85385):

Figure kpo00009
Figure kpo00009

상기 식에서, R1은 C1-5알킬, C3-5알켄일, C3-5알킨일 또는 C1-3알콕시메틸이고, X는 수소, 플루오르 또는 염소이며, A는 질소 원자가 벤젠 고리에 결합된

Figure kpo00010
또는
Figure kpo00011
이고, R2및 R3은 수소 또는 메틸이다.Wherein R 1 is C 1-5 alkyl, C 3-5 alkenyl, C 3-5 alkynyl or C 1-3 alkoxymethyl, X is hydrogen, fluorine or chlorine, and A is a nitrogen atom in the benzene ring Combined
Figure kpo00010
or
Figure kpo00011
And R 2 and R 3 are hydrogen or methyl.

(7) 하기 일반식의 테트라히드로프탈이미드 유도체(일본국 특허 공개 61-30586호):(7) Tetrahydrophthalimide derivatives of the following general formula (Japanese Patent Laid-Open No. 61-30586):

Figure kpo00012
Figure kpo00012

상기 식에서, R1은 알킬, 알켄일, 알킨일, 알콕시알킬 또는 알콕시알콕시알킬이고, R2는 수소 또는 메틸이다.Wherein R 1 is alkyl, alkenyl, alkynyl, alkoxyalkyl or alkoxyalkoxyalkyl and R 2 is hydrogen or methyl.

(8) 하기 일반식의 테트라히드로프탈이미드 유도체(일본국 특허 공개 61-76486호):(8) Tetrahydrophthalimide derivatives of the following general formula (Japanese Patent Laid-Open No. 61-76486):

Figure kpo00013
Figure kpo00013

상기 식에서, R1은 알킬, 알켄일, 알킨일, 알콕시알킬 또는 알콕시알콕시알킬이고, R2는 수소 또는 메틸이다.Wherein R 1 is alkyl, alkenyl, alkynyl, alkoxyalkyl or alkoxyalkoxyalkyl and R 2 is hydrogen or methyl.

(9) 하기 일반식의 테트라히드로프탈이미드 유도체(일본국 특허 61-43188호):(9) Tetrahydrophthalimide derivatives of the following general formula (Japanese Patent No. 61-43188):

Figure kpo00014
Figure kpo00014

상기 식에서, R은 C1-5알킬, C3-5알켄일, C3-5알킨일 또는 C1-3알콕시메틸이고, X는 수소 또는 플루오르이다.Wherein R is C 1-5 alkyl, C 3-5 alkenyl, C 3-5 alkynyl or C 1-3 alkoxymethyl, and X is hydrogen or fluorine.

(10) 하기 일반식의 제초성 화합물 및 그의 치환된 유도체(미합중국 특허 3,981,715호):(10) herbicidal compounds of the general formula and substituted derivatives thereof (US Pat. No. 3,981,715):

Figure kpo00015
Figure kpo00015

상기 식에서, X는 수소 또는 히드록시이고, R1은 수소 또는 할로이며, R2는 알킬, 시클로알킬, 페닐, 알켄일이다.Wherein X is hydrogen or hydroxy, R 1 is hydrogen or halo, and R 2 is alkyl, cycloalkyl, phenyl, alkenyl.

(11) 하기 일반식의 제초성 화합물 및 그의 치환된 유도체(미합중국 특허 3,869,457호):(11) herbicidal compounds of the general formula and substituted derivatives thereof (US Pat. No. 3,869,457):

Figure kpo00016
Figure kpo00016

상기 식에서, X는 수소 또는 히드록시이고, R1은 수소 또는 할로이며, R2는 알킬, 시클로알킬, 페닐, 알켄일이다.Wherein X is hydrogen or hydroxy, R 1 is hydrogen or halo, and R 2 is alkyl, cycloalkyl, phenyl, alkenyl.

(12) 일반식(I)의 화합물 및 그의 에놀 에테르와 염(WO 88/10254호):(12) A compound of formula (I) and an enol ether and salt thereof (WO 88/10254):

Figure kpo00017
Figure kpo00017

상기 식에서, R1은 수소, C1-4알킬, C3-4알켄일, C3-4알킨일 또는 C1-4할로알킬이고, R2

Figure kpo00018
이고, 또는 R1이 할로알킬, 수소, C1-8알킬, C2-8알켄일, C2-8알킨일 또는 C2-8알콕시알킬인 경우, R3은 할로겐 또는 시아노이며, R4는 수소 또는 할로겐이고, R5는 수소, 플루오르 또는 C1-4할로알킬이다.Wherein R 1 is hydrogen, C 1-4 alkyl, C 3-4 alkenyl, C 3-4 alkynyl or C 1-4 haloalkyl, R 2 is
Figure kpo00018
When R 1 is haloalkyl, hydrogen, C 1-8 alkyl, C 2-8 alkenyl, C 2-8 alkynyl or C 2-8 alkoxyalkyl, R 3 is halogen or cyano, R 4 is hydrogen or halogen and R 5 is hydrogen, fluorine or C 1-4 haloalkyl.

전술한 조건(1) 내지 (7)을 충족시킬 수 있는 제초제, 즉 농작물에 아무런 손상(농작물 피해)도 끼치지 않으면서 효력상 선택성을 나타내고 낮은 투여량으로도 광범위한 잡초에 대해 탁월한 제초 효과를 나타내며 또한 토양처리 및 엽면처리 모두에 의해서 목적하는 효과를 나타낼 수 있는 제초제의 개발이 강하게 요구된다.Herbicides capable of meeting the above conditions (1) to (7), i.e., have no effect on crops (crop damage) and are effectively selective and exhibit excellent herbicidal effects against a wide range of weeds at low doses. There is also a strong demand for the development of herbicides that can achieve the desired effect by both soil treatment and foliar treatment.

본 발명자들이 예의 연구한 결과, 5-위치에 할로알킬기 및 특수 치환체를 가지는 2-위치에 페닐기를 갖는 하기 일반식(I)의 우라실 유도체가 침투성 이동 활성 및 매우 높은 제초 활성을 가지며, 종래의 제초성 화합물과 비교하여 상기 우라실 유도체가 토양처리 또는 엽면처리에 의해 투여될 수 있으며 따라서 다년생 잡초를 포함하여 다양한 잡초에 대해서 매우 낮은 투여량으로도 신속하고 높은 제초효과를 일으키고 적절한 기간동안 잔류효과를 나타내는 특성을 갖는다는 것을 발견하였다.As a result of diligent study by the present inventors, the uracil derivatives of the following general formula (I) having a haloalkyl group at the 5-position and a phenyl group at the 2-position have permeability transfer activity and very high herbicidal activity. Compared with herbaceous compounds, the uracil derivatives can be administered by soil treatment or foliar treatment, thus causing rapid and high herbicidal effects at very low dosages for a variety of weeds, including perennial weeds and exhibiting residual effects over an appropriate period of time. It has been found to have properties.

본 발명의 제1요지에서, 하기 일반식(I)의 우라실 유도체가 제공된다:In a first aspect of the invention, uracil derivatives of the general formula (I) are provided:

Figure kpo00019
Figure kpo00019

상기 식에서, R1은 수소, C1-3알킬, 히드록시메틸 또는 C1-3할로알킬이고, R2는 C1-6할로알킬이고, R3은 수소, C1-6알킬, C1-6할로알킬, 히드록시메틸, 할로겐 또는 니트로이며, R4는 수소 또는 할로겐이고, (i) R5와 R6이 개별적으로 취해지는 경우, R5는 할로겐, 니트로 또는 시아노이고, R6은 -S-B1,Wherein R 1 is hydrogen, C 1-3 alkyl, hydroxymethyl or C 1-3 haloalkyl, R 2 is C 1-6 haloalkyl, R 3 is hydrogen, C 1-6 alkyl, C 1 -6 haloalkyl, hydroxymethyl, halogen or nitro, R 4 is hydrogen or halogen, (i) when R 5 and R 6 are taken separately, R 5 is halogen, nitro or cyano, R 6 Is -SB 1 ,

Figure kpo00020
Figure kpo00020

Figure kpo00021
Figure kpo00021

Figure kpo00022
Figure kpo00022

B1은 수소, C1-5알킬, C3-6시클로알킬, C2-4알켄일, C3-4알킨일, 시아노메틸, 히드록시메틸, 클로로메틸, 벤질,B 1 is hydrogen, C 1-5 alkyl, C 3-6 cycloalkyl, C 2-4 alkenyl, C 3-4 alkynyl, cyanomethyl, hydroxymethyl, chloromethyl, benzyl,

Figure kpo00023
Figure kpo00023

CH2-(CH2)n-CO2B22, CH2-Y-B23, CH2-Y-CH(B21)CO2B22, 또는 CH2-Y-CH2-(CH2)n-CO2B22이며, B21은 수소, C1-3알킬, 메틸티오, 페닐티오 또는 메톡시메틸이고, B22는 수소, 나트륨, 칼륨, 암모늄, 이소프로필암모늄, C1-5알킬, C2-5알켄일, C3-5알킨일, C3-6시클로알킬, C3-6시클로알킬-C1-2알킬, C2-3할로알킬, 펜에틸, α-메틸벤질, 3-디메틸아미노프로필; 할로겐, C1-4알킬, C1-3알콕실, C1-2알킬아미노, 디메틸아미노, C1-2알콕시-카르보닐, C2-3아실, C1-2할로알킬 또는 C1-2할로알킬옥실로부터 선정된 치환체 1 이상에 의해 치환될 수 있는 페닐; 할로겐, C1-4알킬, C1-3알콕실, C1-2알킬아미노, 디메틸아미노, C2-3아실, 트리플루오로아세틸아미노, C1-2알콕시-카르보닐, 메틸술폰일, 트리플루오로메틸-술폰일, C1-2할로알킬 또는 C1-2할로알킬옥실로부터 선정된 치환체 1 이상에 의해 치환될 수 있는 벤질이며, n은 1 내지 4의 정수이고, B23은 수소, C1-5알킬, 시아노메틸, C2-5아실, 클로로아세틸 또는 디메틸카르바모일이고, Y는 산소 또는 황이며, D21은 수소, C1-3알킬, C1-3알콕실 또는 C1-3알콕시-C1-2알킬이고, D22는 수소, C1-4알킬, C3-6시클로알킬, C2-3할로알킬, 페닐 또는 벤질이며, D23은 수소 또는 C1-3알킬이고, D24는 수소, C1-3알킬 또는 C1-3알콕시-C1-2알킬이고, Z는 산소, 황 또는 NH이고, D25는 수소, 나트륨, C1-4알킬, C2-5알켄일, C3-5알킨일, C2-5아실, C1-4알킬술폰일 또는 C1-3알콕시-C1-2알킬이며, D26은 C1-4알킬 또는 C1-3할로알킬이고, D27은 수소, C1-6알킬, C3-6시클로알킬, C1-3할로알킬, C1-4알콕실, C1-4알킬티오, C1-4알콕시-카르보닐, 메르캅토, 히드록실, C1-3알콕시-C1-2알킬, C1-4알킬아미노, ND28(D29), 디메틸카르바모일, CONHSO2CH3, C1-4알킬술폰일, 또는 N(D30)SO2D31이며, D28및 D29는 독립적으로 C1-4알킬이고, D30은 수소, 나트륨, C1-4알킬, C1-4알킬술폰일, C1-3알콕시-C1-2알킬이고, D31은 C1-4알킬 또는 C1-3할로알킬이고, D32는 C1-6알킬 또는 C3-6시클로알킬이며, D33, D34및 D35는 독립적으로 수소 또는 C1-6알킬이고, D36및 D37은 독립적으로 수소, C1-6알킬 또는 디메틸아미노이며, D38은 수소, 할로겐, 메르캅토, 히드록실, C1-6알킬, C3-6시클로알킬, C1-3할로알킬, C1-4알콕실, C1-4알킬티오, C1-4알콕시-카르보닐, 디메틸카르바모일, C1-3알콕시-C1-2알킬, C1-4알킬아미노, ND28(D29), CONHSO2CH3, C1-4알킬술폰일, 페닐, 벤질 또는 N(D39)SO2D31이며, D39는 수소, C1-4알킬, 나트륨, 칼륨, C1-4알킬술포닐 또는 C1-3알콕시-C1-2알킬이고, D40은 수소, C1-6알킬, C3-6시클로알킬, 페닐, 벤질 또는 2-피리딜이고, D41은 수소, 할로겐, 메르캅토, 히드록실, 아미노, C1-6알킬, C1-4알킬아미노, ND28(D29), C1-4알킬티오, CO2D28, C1-4알킬술폰일, C1-4알콕실 또는 N(D39)SO2D31이며, D42는 수소, 할로겐, 니트로, 아미노, 시아노, C1-4알킬아미노, N(D28)D29, C1-4알킬카르보닐 또는 C1-4알콕시-카르보닐이며, D43은 수소, 히드록실, 메톡시, 아미노, 벤조일 또는 C1-4알킬이고, D44는 수소, 시아노, 아세틸, C1-4알킬, 카르복실 또는 C1-4알콕시-카르보닐이고, D45및 D46은 독립적으로 수소, 페닐, 히드록실, 메톡시 또는 C1-4알킬이며, D47및 D48은 독립적으로 수소 또는 C1-4알킬이고, X는 산소 또는 황이고, (ii) R5와 R6이 고리를 형성하는 경우, 상기 우라실 유도체는 일반식CH 2- (CH 2 ) n -CO 2 B 22 , CH 2 -YB 23 , CH 2 -Y-CH (B 21 ) CO 2 B 22 , or CH 2 -Y-CH 2- (CH 2 ) n- CO 2 B 22 , B 21 is hydrogen, C 1-3 alkyl, methylthio, phenylthio or methoxymethyl, B 22 is hydrogen, sodium, potassium, ammonium, isopropylammonium, C 1-5 alkyl, C 2-5 alkenyl, C 3-5 alkynyl, C 3-6 cycloalkyl, C 3-6 cycloalkyl-C 1-2 alkyl, C 2-3 haloalkyl, phenethyl, α-methylbenzyl, 3- Dimethylaminopropyl; Halogen, C 1-4 alkyl, C 1-3 alkoxyl, C 1-2 alkylamino, dimethylamino, C 1-2 alkoxy-carbonyl, C 2-3 acyl, C 1-2 haloalkyl or C 1- Phenyl which may be substituted by one or more substituents selected from 2 haloalkyloxyl; Halogen, C 1-4 alkyl, C 1-3 alkoxyl, C 1-2 alkylamino, dimethylamino, C 2-3 acyl, trifluoroacetylamino, C 1-2 alkoxy-carbonyl, methylsulfonyl, Benzyl which may be substituted by one or more substituents selected from trifluoromethyl-sulfonyl, C 1-2 haloalkyl or C 1-2 haloalkyloxyl, n is an integer from 1 to 4, B 23 is hydrogen , C 1-5 alkyl, cyanomethyl, C 2-5 acyl, chloroacetyl or dimethylcarbamoyl, Y is oxygen or sulfur, D 21 is hydrogen, C 1-3 alkyl, C 1-3 alkoxyl Or C 1-3 alkoxy-C 1-2 alkyl, D 22 is hydrogen, C 1-4 alkyl, C 3-6 cycloalkyl, C 2-3 haloalkyl, phenyl or benzyl, D 23 is hydrogen or C 1-3 alkyl, D 24 is hydrogen, C 1-3 alkyl or C 1-3 alkoxy-C 1-2 alkyl, Z is oxygen, sulfur or NH, D 25 is hydrogen, sodium, C 1-4 Alkyl, C 2-5 alkenyl, C 3-5 alkynyl, C 2-5 acyl, C 1-4 alkylsulfonyl or C 1-3 alkoxy-C 1-2 alkyl, D 26 is C 1-4 alkyl or C 1-3 haloalkyl, D 27 is hydrogen, C 1-6 alkyl, C 3-6 cycloalkyl, C 1- 3 haloalkyl, C 1-4 alkoxyl, C 1-4 alkylthio, C 1-4 alkoxy-carbonyl, mercapto, hydroxyl, C 1-3 alkoxy-C 1-2 alkyl, C 1-4 alkyl Amino, ND 28 (D 29 ), dimethylcarbamoyl, CONHSO 2 CH 3 , C 1-4 alkylsulfonyl, or N (D 30 ) SO 2 D 31 , and D 28 and D 29 are independently C 1- 4 alkyl, D 30 is hydrogen, sodium, C 1-4 alkyl, C 1-4 alkylsulfonyl, C 1-3 alkoxy-C 1-2 alkyl, D 31 is C 1-4 alkyl or C 1- 3 haloalkyl, D 32 is C 1-6 alkyl or C 3-6 cycloalkyl, D 33 , D 34 and D 35 are independently hydrogen or C 1-6 alkyl, and D 36 and D 37 are independently Hydrogen, C 1-6 alkyl or dimethylamino, D 38 is hydrogen, halogen, mercapto, hydroxyl, C 1-6 alkyl, C 3-6 cycloalkyl, C 1-3 haloalkyl, C 1-4 al Coxyl, C 1-4 Alkyl Tea Oh, C 1-4 alkoxy-carbonyl, dimethylcarbamoyl, C 1-3 alkoxy-C 1-2 alkyl, C 1-4 alkylamino, ND 28 (D 29 ), CONHSO 2 CH 3 , C 1- 4 alkylsulfonyl, phenyl, benzyl or N (D 39 ) SO 2 D 31 , where D 39 is hydrogen, C 1-4 alkyl, sodium, potassium, C 1-4 alkylsulfonyl or C 1-3 alkoxy-C 1-2 alkyl, D 40 is hydrogen, C 1-6 alkyl, C 3-6 cycloalkyl, phenyl, benzyl or 2-pyridyl, D 41 is hydrogen, halogen, mercapto, hydroxyl, amino, C 1-6 alkyl, C 1-4 alkylamino, ND 28 (D 29 ), C 1-4 alkylthio, CO 2 D 28 , C 1-4 alkylsulfonyl, C 1-4 alkoxyl or N (D 39 ) SO 2 D 31 , D 42 is hydrogen, halogen, nitro, amino, cyano, C 1-4 alkylamino, N (D 28 ) D 29 , C 1-4 alkylcarbonyl or C 1-4 alkoxy- Carbonyl, D 43 is hydrogen, hydroxyl, methoxy, amino, benzoyl or C 1-4 alkyl, D 44 is hydrogen, cyano, acetyl, C 1-4 alkyl, carboxyl or C 1-4 alkoxy Ka A carbonyl, D 45 and D 46 are independently hydrogen, phenyl, hydroxyl, methoxy or a C 1-4 alkyl, D 47 and D 48 are independently hydrogen or C 1-4 alkyl, X is oxygen or sulfur And (ii) when R 5 and R 6 form a ring, the uracil derivative is of the general formula

Figure kpo00024
Figure kpo00024

Figure kpo00025
Figure kpo00025

Figure kpo00026
Figure kpo00026

Figure kpo00027
Figure kpo00027

Figure kpo00028
Figure kpo00028

이고, A1은 수소 및 C1-4알킬이고, A2는 수소, C1-5알킬, C2-5알켄일, C3-5알킨일, C3-6시클로알킬-C1-2알킬, C1-6할로알킬, C1-6할로알켄일, C1-6할로알킨일, 시아노메틸, 히드록시메틸, 클로로메틸, C1-3알콕시-C1-2알킬, -CH2CO2A21, -CH2CON(A22)A23; C1-4알킬, C1-4할로알킬, C1-4알콕시 또는 할로겐에 의해 치환될 수 있는 페닐; C1-4알킬, C1-4할로알킬, C1-4알콕시, C1-4알콕시-카르보닐, C1-3알콕시-C1-2알킬 또는 할로겐에 의해 치환될 수 있는 벤질; 또는 -CH2A24이며, A21은 수소, C1-5알킬, 나트륨, 할로겐에 의해 치환될 수 있는 페닐, 또는 할로겐에 의해 치환될 수 있는 벤질이고, A22및 A23은 독립적으로 수소 또는 C1-3알킬이고, A24는 C1-4알킬 또는 할로겐에 의해 치환될 수 있는 2-피리딜; C1-4알킬 또는 할로겐에 의해 치환될 수 있는 2-피리다질; 3-이소티아졸 또는 3-이소옥사졸이며, J는 수소, C1-4알킬, C2-4알켄일, C3-4알킨일, 히드록시메틸, 클로로메틸, 카르바모일메틸, 시아노메틸, C1-4알콕시-카르보닐메틸,

Figure kpo00029
, C3-6시클로알킬,
Figure kpo00030
, C3-6시클로알킬-C1-2알킬, C1-2알콕시-C1-2알킬; C1-4알킬, C1-4알콕시, C1-4알콕시-카르보닐, C1-4알콕시-C1-2알킬 또는 할로겐에 의해 치환될 수 있는 페닐; 또는 C1-4알킬, C1-4알콕실, C1-4알콕시-카르보닐, C1-4알콕시-C1-2알킬 또는 할로겐에 의해 치환될 수 있는 벤질이다., A 1 is hydrogen and C 1-4 alkyl, A 2 is hydrogen, C 1-5 alkyl, C 2-5 alkenyl, C 3-5 alkynyl, C 3-6 cycloalkyl-C 1-2 Alkyl, C 1-6 haloalkyl, C 1-6 haloalkenyl, C 1-6 haloalkynyl, cyanomethyl, hydroxymethyl, chloromethyl, C 1-3 alkoxy-C 1-2 alkyl, -CH 2 C0 2 A 21 , -CH 2 CON (A 22 ) A 23 ; Phenyl which may be substituted by C 1-4 alkyl, C 1-4 haloalkyl, C 1-4 alkoxy or halogen; Benzyl which may be substituted by C 1-4 alkyl, C 1-4 haloalkyl, C 1-4 alkoxy, C 1-4 alkoxy-carbonyl, C 1-3 alkoxy-C 1-2 alkyl or halogen; Or —CH 2 A 24 , A 21 is hydrogen, C 1-5 alkyl, sodium, phenyl which may be substituted by halogen, or benzyl which may be substituted by halogen, and A 22 and A 23 are independently hydrogen Or C 1-3 alkyl, A 24 is 2-pyridyl, which may be substituted by C 1-4 alkyl or halogen; 2-pyridazyl, which may be substituted by C 1-4 alkyl or halogen; 3-isothiazole or 3-isoxazole, J is hydrogen, C 1-4 alkyl, C 2-4 alkenyl, C 3-4 alkynyl, hydroxymethyl, chloromethyl, carbamoylmethyl, cyano Methyl, C 1-4 alkoxy-carbonylmethyl,
Figure kpo00029
, C 3-6 cycloalkyl,
Figure kpo00030
, C 3-6 cycloalkyl-C 1-2 alkyl, C 1-2 alkoxy-C 1-2 alkyl; Phenyl which may be substituted by C 1-4 alkyl, C 1-4 alkoxy, C 1-4 alkoxy-carbonyl, C 1-4 alkoxy-C 1-2 alkyl or halogen; Or benzyl which may be substituted by C 1-4 alkyl, C 1-4 alkoxyl, C 1-4 alkoxy-carbonyl, C 1-4 alkoxy-C 1-2 alkyl or halogen.

본 발명의 제2요지에서는, 제1요지에서 정의한 우라실 유도체 제초 유효량과 허용가능한 담체 또는 희석제를 포함하는 제초성 조성물이 제공된다.In a second aspect of the invention there is provided a herbicidal composition comprising an herbicidally effective amount of the uracil derivative defined in the first aspect and an acceptable carrier or diluent.

본 발명의 제3요지에서는, 제1요지에서 정의한 우라실 유도체 제초 유효량을 투여하는 것을 포함하는, 잡초를 죽이거나 또는 잡초의 생장을 억제하는 방법이 제공된다.In a third aspect of the present invention, there is provided a method for killing or inhibiting weed growth, comprising administering an effective amount of the uracil derivative herbicide defined in the first aspect.

본 발명에 따라 상기 일반식(I)로 나타내어진 우라실 유도체는 신규하다.According to the invention the uracil derivatives represented by the general formula (I) are novel.

일반식(I)의 우라실 유도체 중에서, 일반식(II), (III) 및 (IV)의 화합물이 본 발명의 목적에 바람직하다. 즉, 일반식(II)의 우라실 유도체는 하기와 같다:Among the uracil derivatives of general formula (I), the compounds of general formulas (II), (III) and (IV) are preferred for the purposes of the present invention. That is, the uracil derivatives of general formula (II) are as follows:

Figure kpo00031
Figure kpo00031

상기 식에서, R1은 수소, C1-3알킬, 히드록시메틸 또는 할로메틸이고, R2는 C1-6할로알킬이며, R3은 수소, C1-6알킬, C1-6할로알킬, 히드록시메틸, 할로겐 또는 니트로이고, R4는 수소 또는 할로겐이고, A1은 수소 또는 C1-4알킬이고, A2는 수소, C1-5알킬, C2-5알켄일, C3-5알킨일, C3-6시클로알킬-C1-2알킬, C1-6할로알킬, C1-6할로알켄일, C1-6할로알킨일, 시아노메틸, 히드록시메틸, 클로로메틸, C1-3알콕시-C1-2알킬, -CH2CO2A21, -CH2CON(A22)A23; C1-4알킬, C1-4할로알킬, C1-4알콕실 또는 할로겐에 의해 치환될 수 있는 페닐; C1-4알킬, C1-4할로알킬, C1-4알콕실, C1-4알콕시-카르보닐, C1-3알콕시-C1-2알킬 또는 할로겐에 의해 치환될 수 있는 벤질; 또는 -CH2A24이고, A21은 수소, C1-5알킬, 나트륨, 할로겐에 의해 치환될 수 있는 페닐, 또는 할로겐에 의해 치환될 수 있는 벤질이며, A22및 A23은 독립적으로 수소 또는 C1-3알킬이고, A24는 C1-4알킬 또는 할로겐에 의해 치환될 수 있는 2-피리딜; C1-4알킬 또는 할로겐에 의해 치환될 수 있는 2-피리다질; 3-이소티아졸 또는 3-이소옥사졸이며, X는 산소 또는 황이다.Wherein R 1 is hydrogen, C 1-3 alkyl, hydroxymethyl or halomethyl, R 2 is C 1-6 haloalkyl, R 3 is hydrogen, C 1-6 alkyl, C 1-6 haloalkyl , Hydroxymethyl, halogen or nitro, R 4 is hydrogen or halogen, A 1 is hydrogen or C 1-4 alkyl, A 2 is hydrogen, C 1-5 alkyl, C 2-5 alkenyl, C 3 -5 alkynyl, C 3-6 cycloalkyl-C 1-2 alkyl, C 1-6 haloalkyl, C 1-6 haloalkenyl, C 1-6 haloalkinyl, cyanomethyl, hydroxymethyl, chloro Methyl, C 1-3 alkoxy-C 1-2 alkyl, —CH 2 CO 2 A 21 , —CH 2 CON (A 22 ) A 23 ; Phenyl which may be substituted by C 1-4 alkyl, C 1-4 haloalkyl, C 1-4 alkoxyl or halogen; Benzyl which may be substituted by C 1-4 alkyl, C 1-4 haloalkyl, C 1-4 alkoxyl, C 1-4 alkoxy-carbonyl, C 1-3 alkoxy-C 1-2 alkyl or halogen; Or —CH 2 A 24 , A 21 is hydrogen, C 1-5 alkyl, sodium, phenyl which may be substituted by halogen, or benzyl which may be substituted by halogen, and A 22 and A 23 are independently hydrogen Or C 1-3 alkyl, A 24 is 2-pyridyl, which may be substituted by C 1-4 alkyl or halogen; 2-pyridazyl, which may be substituted by C 1-4 alkyl or halogen; 3-isothiazole or 3-isoxazole and X is oxygen or sulfur.

일반식(III)의 우라실 유도체는 하기와 같다:The uracil derivatives of formula (III) are as follows:

Figure kpo00032
Figure kpo00032

상기 식에서, R1은 수소, C1-3알킬, 히드록시메틸 또는 할로메틸이고, R2는 C1-6할로알킬이고, R3은 수소, C1-6알킬, C1-6할로알킬, 히드록시메틸, 할로겐 또는 니트로이며, R4는 수소 또는 할로겐이고, R5는 할로겐, 니트로 또는 시아노이고, B1은 수소, C1-5알킬, C3-6시클로알킬, C2-4알켄일, C3-4알킨일, 시아노메틸, 히드록시메틸, 클로로메틸, 벤질,Wherein R 1 is hydrogen, C 1-3 alkyl, hydroxymethyl or halomethyl, R 2 is C 1-6 haloalkyl, R 3 is hydrogen, C 1-6 alkyl, C 1-6 haloalkyl , Hydroxymethyl, halogen or nitro, R 4 is hydrogen or halogen, R 5 is halogen, nitro or cyano, B 1 is hydrogen, C 1-5 alkyl, C 3-6 cycloalkyl, C 2- 4 alkenyl, C 3-4 alkynyl, cyanomethyl, hydroxymethyl, chloromethyl, benzyl,

Figure kpo00033
Figure kpo00033

CH2-Y-B23, CH2-Y-CH(B21)CO2B22, 또는 CH2-Y-CH2-(CH2)n-CO2B22이며, B21은 수소, C1-3알킬, 메틸티오, 페닐티오 또는 메톡시메틸이고, B22는 수소, 나트륨, 칼륨, 암모늄, 이소프로필암모늄, C1-5알킬, C2-5알켄일, C3-5알킨일, C3-6시클로알킬, C3-6시클로알킬-C1-2알킬, C2-3할로알킬, 펜에틸, α-메틸벤질, 3-디메틸아미노프로필; 할로겐, C1-4알킬, C1-3알콕실, C1-2알킬아미노, 디메틸아미노, C1-2알콕시-카르보닐, C2-3아실, C1-2할로알킬 또는 C1-2할로알킬옥실로부터 선정된 1이상의 치환체로 치환될 수 있는 페닐; 또는 할로겐, C1-4알킬, C1-3알콕실, C1-2알킬아미노, 디메틸아미노, C2-3아실, 트리플루오로아세틸아미노, C1-2알콕시-카르보닐, 메틸술폰일, 트리플루오로메틸-술폰일, C1-2할로알킬 또는 C1-2할로알킬옥실로부터의 치환체 1 이상에 의해 치환될 수 있는 벤질이며, n은 1 내지 4의 정수이고, B23은 수소, C1-5알킬, 시아노메틸, C2-5아실, 클로로아세틸 또는 디메틸-카르바모일이고, X 및 Y는 산소 또는 황이다.CH 2 -YB 23 , CH 2 -Y-CH (B 21 ) CO 2 B 22 , or CH 2 -Y-CH 2- (CH 2 ) n -CO 2 B 22 , B 21 is hydrogen, C 1- 3 alkyl, methylthio, phenylthio or methoxymethyl, B 22 is hydrogen, sodium, potassium, ammonium, isopropylammonium, C 1-5 alkyl, C 2-5 alkenyl, C 3-5 alkynyl, C 3-6 cycloalkyl, C 3-6 cycloalkyl-C 1-2 alkyl, C 2-3 haloalkyl, phenethyl, α-methylbenzyl, 3-dimethylaminopropyl; Halogen, C 1-4 alkyl, C 1-3 alkoxyl, C 1-2 alkylamino, dimethylamino, C 1-2 alkoxy-carbonyl, C 2-3 acyl, C 1-2 haloalkyl or C 1- Phenyl which may be substituted with one or more substituents selected from 2 haloalkyloxyl; Or halogen, C 1-4 alkyl, C 1-3 alkoxyl, C 1-2 alkylamino, dimethylamino, C 2-3 acyl, trifluoroacetylamino, C 1-2 alkoxy-carbonyl, methylsulfonyl Benzyl which may be substituted by one or more substituents from trifluoromethyl-sulfonyl, C 1-2 haloalkyl or C 1-2 haloalkyloxyl, n is an integer from 1 to 4, B 23 is hydrogen , C 1-5 alkyl, cyanomethyl, C 2-5 acyl, chloroacetyl or dimethyl-carbamoyl, and X and Y are oxygen or sulfur.

일반식(IV)의 우라실 유도체는 하기와 같다:The uracil derivatives of general formula (IV) are as follows:

Figure kpo00034
Figure kpo00034

상기 식에서, R1은 수소, C1-3알킬 또는 C1-3할로알킬이고, R2는 C1-6할로알킬이고, R3은 수소, C1-6알킬, C1-6할로알킬, 히드록시메틸, 할로겐 또는 니트로이며, R4는 수소 또는 할로겐이고, (i) R5와 D1을 개별적으로 취하는 경우, R5는 할로겐, 니트로 또는 시아노이고, D1Wherein R 1 is hydrogen, C 1-3 alkyl or C 1-3 haloalkyl, R 2 is C 1-6 haloalkyl, R 3 is hydrogen, C 1-6 alkyl, C 1-6 haloalkyl , Hydroxymethyl, halogen or nitro, R 4 is hydrogen or halogen, (i) when R 5 and D 1 are taken separately, R 5 is halogen, nitro or cyano, and D 1 is

Figure kpo00035
Figure kpo00035

Figure kpo00036
Figure kpo00036

Figure kpo00037
Figure kpo00037

또는or

Figure kpo00038
Figure kpo00038

이며, D21은 수소, C1-3알킬, C1-3알콕실 또는 C1-3알콕시-C1-2알킬이고, D22는 수소, C1-4알킬, C3-6시클로알킬, C2-3할로알킬, 페닐 또는 벤질이고, D23은 수소 또는 C1-3알킬이고, D24는 수소, C1-3알킬 또는 C1-3알콕시-C1-2알킬이며, Z는 산소, 황 또는 NH이고, D25는 수소, 나트륨, C1-4알킬, C2-5알켄일, C3-5알킨일, C2-5아실, C1-4알킬술폰일 또는 C1-3알콕시-C1-2알킬이고, D26은 C1-4알킬 또는 C1-3할로알킬이고, D27은 수소, C1-6알킬, C3-6시클로알킬, C1-3할로알킬, C1-4알콕실, C1-4알킬티오, C1-4알콕시-카르보닐, 메르캅토, 히드록실, C1-3알콕시-C1-2알킬, C1-4알킬아미노, ND28(D29), 디메틸카르바모일, CONHSO2CH3, C1-4알킬술폰일, 또는 N(D30)SO2D31이며, D28및 D29는 독립적으로 C1-4알킬이고, D30은 수소, 나트륨, C1-4알킬, C1-4알킬술폰일 또는 C1-3알콕시-C1-2알킬이며, D31은 C1-4알킬 또는 C1-3할로알킬이고, D32는 C1-6알킬 또는 C3-6시클로알킬이고, D33, D34및 D35는 독립적으로 수소 또는 C1-6알킬이고, D36및 D37은 각각 독립적으로 수소, C1-6알킬 또는 디메틸아미노이며, D38은 수소, 할로겐, 메르캅토, 히드록실, C1-6알킬, C3-6시클로알킬, C1-3할로알킬, C1-4알콕실, C1-4알킬티오, C1-4알콕시-카르보닐, 디메틸카르바모일, C1-3알콕시-C1-2알킬, C1-4알킬아미노, ND28(D29), CONHSO2CH3, C1-4알킬술폰일, 페닐, 벤질 또는 N(D39)SO2D31이며, D39는 수소, C1-4알킬, 나트륨, 칼륨, C1-4알킬술폰일 또는 C1-3알콕시-C1-2알킬이고, D40은 수소, C1-6알킬, C3-6시클로알킬, 페닐, 벤질 또는 2-피리딜이고, D41은 수소, 할로겐, 메르캅토, 히드록실, 아미노, C1-6알킬, C1-4알킬아미노, ND28(D29), C1-4알킬티오, CO2D28, C1-4알킬술폰일, C1-4알콕실 또는 N(D39)SO2D31이며, D42는 수소, 할로겐, 니트로, 아미노, 시아노, C1-4알킬아미노, N(D28)D29, C1-4알킬카르보닐 또는 C1-4알콕시-카르보닐이고, D43은 수소, 히드록실, 메톡시, 아미노, 벤조일 또는 C1-4알킬이며, D44는 수소, 시아노, 아세틸, C1-4알킬, 카르복실 또는 C1-4알콕시-카르보닐이며, D45및 D46은 각각 독립적으로 수소, 페닐, 히드록실, 메톡시 또는 C1-4알킬이며, D47및 D48은 각각 독립적으로 수소 또는 C1-4알킬이고, X는 산소 또는 황이며, (ii) R5와 D1이 고리를 형성하는 경우, 상기 우라실 유도체는 일반식D 21 is hydrogen, C 1-3 alkyl, C 1-3 alkoxyl or C 1-3 alkoxy-C 1-2 alkyl, D 22 is hydrogen, C 1-4 alkyl, C 3-6 cycloalkyl , C 2-3 haloalkyl, phenyl or benzyl, D 23 is hydrogen or C 1-3 alkyl, D 24 is hydrogen, C 1-3 alkyl or C 1-3 alkoxy-C 1-2 alkyl, Z Is oxygen, sulfur or NH and D 25 is hydrogen, sodium, C 1-4 alkyl, C 2-5 alkenyl, C 3-5 alkynyl, C 2-5 acyl, C 1-4 alkylsulfonyl or C 1-3 alkoxy-C 1-2 alkyl, D 26 is C 1-4 alkyl or C 1-3 haloalkyl, D 27 is hydrogen, C 1-6 alkyl, C 3-6 cycloalkyl, C 1- 3 haloalkyl, C 1-4 alkoxyl, C 1-4 alkylthio, C 1-4 alkoxy-carbonyl, mercapto, hydroxyl, C 1-3 alkoxy-C 1-2 alkyl, C 1-4 alkyl Amino, ND 28 (D 29 ), dimethylcarbamoyl, CONHSO 2 CH 3 , C 1-4 alkylsulfonyl, or N (D 30 ) SO 2 D 31 , and D 28 and D 29 are independently C 1- 4 alkyl, D 30 is hydrogen, sodium, C 1-4 alkyl, C 1-4 al Kilssulfonyl or C 1-3 alkoxy-C 1-2 alkyl, D 31 is C 1-4 alkyl or C 1-3 haloalkyl, D 32 is C 1-6 alkyl or C 3-6 cycloalkyl, D 33 , D 34 and D 35 are independently hydrogen or C 1-6 alkyl, D 36 and D 37 are each independently hydrogen, C 1-6 alkyl or dimethylamino, D 38 is hydrogen, halogen, mercapto , Hydroxyl, C 1-6 alkyl, C 3-6 cycloalkyl, C 1-3 haloalkyl, C 1-4 alkoxyl, C 1-4 alkylthio, C 1-4 alkoxy-carbonyl, dimethylcarba Moyl, C 1-3 alkoxy-C 1-2 alkyl, C 1-4 alkylamino, ND 28 (D 29 ), CONHSO 2 CH 3 , C 1-4 alkylsulfonyl, phenyl, benzyl or N (D 39 ) SO 2 D 31 , D 39 is hydrogen, C 1-4 alkyl, sodium, potassium, C 1-4 alkylsulfonyl or C 1-3 alkoxy-C 1-2 alkyl, D 40 is hydrogen, C 1- 6 alkyl, C 3-6 cycloalkyl, phenyl, benzyl or 2-pyridyl, D 41 is hydrogen, halogen, mercapto, hydroxyl, amino, C 1-6 alkyl, C 1-4 al Kylamino, ND 28 (D 29 ), C 1-4 alkylthio, CO 2 D 28 , C 1-4 alkylsulfonyl, C 1-4 alkoxyl or N (D 39 ) SO 2 D 31 , D 42 Is hydrogen, halogen, nitro, amino, cyano, C 1-4 alkylamino, N (D 28 ) D 29 , C 1-4 alkylcarbonyl or C 1-4 alkoxy-carbonyl, D 43 is hydrogen, Hydroxyl, methoxy, amino, benzoyl or C 1-4 alkyl, D 44 is hydrogen, cyano, acetyl, C 1-4 alkyl, carboxyl or C 1-4 alkoxy-carbonyl, D 45 and D 46 are each independently hydrogen, phenyl, hydroxyl, methoxy or C 1-4 alkyl, D 47 and D 48 are each independently hydrogen or C 1-4 alkyl, X is oxygen or sulfur, (ii) When R 5 and D 1 form a ring, the uracil derivative is a general formula

Figure kpo00039
Figure kpo00039

Figure kpo00040
Figure kpo00040

Figure kpo00041
Figure kpo00041

Figure kpo00042
Figure kpo00042

이고, J는 수소, C1-4알킬, C2-4알켄일, C3-4알킨일, 히드록시메틸, 클로로메틸, 카르바모일메틸, 시아노메틸, C1-4알콕시-카르보닐메틸,

Figure kpo00043
, C3-6시클로알킬,
Figure kpo00044
, C3-6시클로알킬-C1-2알킬, C1-2알콕시-C1-2알킬; C1-4알킬, C1-4알콕실, C1-4알콕시-카르보닐, C1-4알콕시-C1-2알킬 또는 할로겐에 의해 치환될 수 있는 페닐; 또는 C1-4알킬, C1-4알콕실, C1-4알콕시-카르보닐, C1-4알콕시-C1-2알킬 또는 할로겐에 의해 치환될 수 있는 벤질이다.And J is hydrogen, C 1-4 alkyl, C 2-4 alkenyl, C 3-4 alkynyl, hydroxymethyl, chloromethyl, carbamoylmethyl, cyanomethyl, C 1-4 alkoxy-carbonyl methyl,
Figure kpo00043
, C 3-6 cycloalkyl,
Figure kpo00044
, C 3-6 cycloalkyl-C 1-2 alkyl, C 1-2 alkoxy-C 1-2 alkyl; Phenyl which may be substituted by C 1-4 alkyl, C 1-4 alkoxyl, C 1-4 alkoxy-carbonyl, C 1-4 alkoxy-C 1-2 alkyl or halogen; Or benzyl which may be substituted by C 1-4 alkyl, C 1-4 alkoxyl, C 1-4 alkoxy-carbonyl, C 1-4 alkoxy-C 1-2 alkyl or halogen.

일반식(II), (III) 및 (IV)의 화합물 중에서 하기가 더욱 바람직하다.Among the compounds of the formulas (II), (III) and (IV), the following are more preferred.

하기 일반식(II')의 우라실 유도체:Uracil derivatives of the general formula (II ′)

Figure kpo00045
Figure kpo00045

상기 식에서, R1은 수소 또는 C1-3알킬이고, R2는 C1-4할로알킬이고, R4는 수소 또는 할로겐이며, A2는 수소, C1-5알킬, C2-5알켄일, C3-5알킨일, C3-6시클로알킬-C1-2알킬, 시아노메틸, 히드록시메틸, 클로로메틸, C1-3알콕시-C1-2알킬, -CH2CO2A21, -CH2CON(A22)A23; C1-4알킬, C1-4할로알킬, C1-4알콕시 또는 할로겐에 의해 치환될 수 있는 벤질; 또는 -CH2A24이고, A21은 수소 또는 C1-5알킬이고, A22및 A23은 독립적으로 수소 또는 C1-3알킬이며, A24는 C1-4알킬 또는 할로겐에 의해 치환될 수 있는 2-피리딜이다.Wherein R 1 is hydrogen or C 1-3 alkyl, R 2 is C 1-4 haloalkyl, R 4 is hydrogen or halogen, A 2 is hydrogen, C 1-5 alkyl, C 2-5 al Kenyl, C 3-5 alkynyl, C 3-6 cycloalkyl-C 1-2 alkyl, cyanomethyl, hydroxymethyl, chloromethyl, C 1-3 alkoxy-C 1-2 alkyl, -CH 2 CO 2 A 21 , -CH 2 CON (A 22 ) A 23 ; Benzyl, which may be substituted by C 1-4 alkyl, C 1-4 haloalkyl, C 1-4 alkoxy or halogen; Or -CH 2 A 24 , A 21 is hydrogen or C 1-5 alkyl, A 22 and A 23 are independently hydrogen or C 1-3 alkyl, A 24 is substituted by C 1-4 alkyl or halogen 2-pyridyl which may be used.

하기 일반식(III')의 우라실 유도체:Uracil derivatives of the general formula (III ′)

Figure kpo00046
Figure kpo00046

상기 식에서, R1은 수소 또는 C1-3알킬이고, R2는 C1-4할로알킬이고, R4는 수소 또는 할로겐이고, R5는 염소 또는 니트로이며, B1은 수소, C1-5알킬, C3-6시클로알킬, C2-4알켄일, C3-4알킨일, 시아노메틸, 히드록시메틸, 벤질,Wherein R 1 is hydrogen or C 1-3 alkyl, R 2 is C 1-4 haloalkyl, R 4 is hydrogen or halogen, R 5 is chlorine or nitro, B 1 is hydrogen, C 1- 5 alkyl, C 3-6 cycloalkyl, C 2-4 alkenyl, C 3-4 alkynyl, cyanomethyl, hydroxymethyl, benzyl,

Figure kpo00047
Figure kpo00047

CH2-(CH2)n-CO2B22, CH2-O-B23, 또는 CH2-O-CH(B21)CO2B22이고, B21은 수소, C1-3알킬 또는 메톡시메틸이고, B22는 수소, C1-5알킬, C2-5알켄일, C3-5알킨일, C3-6시클로알킬, C3-6시클로알킬-C1-2알킬, C2-3할로알킬; 또는 할로겐, C1-4알킬, C1-3알콕실, 디메틸아미노, C2-3아실, C1-2알콕시-카르보닐, C1-2할로알킬 또는 C1-2할로알킬옥실로부터 선정된 1 이상의 치환체에 의해 치환될 수 있는 벤질이고, n은 1 내지 3의 정수이며, B23은 수소, C1-5알킬, 시아노메틸, C2-5아실, 클로로아세틸 또는 디메틸카르바모일이다.CH 2- (CH 2 ) n -CO 2 B 22 , CH 2 -OB 23 , or CH 2 -O-CH (B 21 ) CO 2 B 22 , B 21 is hydrogen, C 1-3 alkyl or methoxy Methyl, B 22 is hydrogen, C 1-5 alkyl, C 2-5 alkenyl, C 3-5 alkynyl, C 3-6 cycloalkyl, C 3-6 cycloalkyl-C 1-2 alkyl, C 2 -3 haloalkyl; Or selected from halogen, C 1-4 alkyl, C 1-3 alkoxyl, dimethylamino, C 2-3 acyl, C 1-2 alkoxy-carbonyl, C 1-2 haloalkyl or C 1-2 haloalkyloxyl Benzyl, which may be substituted by one or more substituents, n is an integer from 1 to 3, and B 23 is hydrogen, C 1-5 alkyl, cyanomethyl, C 2-5 acyl, chloroacetyl or dimethylcarbamoyl to be.

하기 일반식(IV')의 우라실 유도체:Uracil derivatives of the general formula (IV ′)

Figure kpo00048
Figure kpo00048

상기 식에서, R1은 수소 또는 C1-3알킬이고, R2는 C1-4할로알킬이고, R4는 수소 또는 할로겐이며, (i) R5와 D1을 개별적으로 취한 경우, R5는 염소 또는 니트로이고, D1Wherein R 1 is hydrogen or C 1-3 alkyl, R 2 is C 1-4 haloalkyl, R 4 is hydrogen or halogen, and (i) when R 5 and D 1 are taken separately, R 5 Is chlorine or nitro, and D 1 is

Figure kpo00049
Figure kpo00049

Figure kpo00050
Figure kpo00050

Figure kpo00051
Figure kpo00051

이고, D21은 수소, 메틸, 메톡시 또는 메톡시메틸이고, D22는 수소, C1-4알킬, C3-6시클로알킬 또는 벤질이며, D23은 수소 또는 메틸이고, D24는 수소, 메틸 또는 메톡시메틸이고, Z는 산소, 황 또는 NH이며, D25는 수소, C1-4알킬, C2-5알켄일, C3-5알킨일, 또는 C1-4알킬술폰일이고, D26은 C1-4알킬이고, D27은 수소, C1-6알킬, C1-4알콕실, C1-4알콕시-카르보닐, 메르캅토, 히드록실, C1-3알콕시-C1-2알킬, C1-4알킬아미노, ND28(D29), 디메틸카르바모일, CONHSO2CH3또는 N(D30)SO2D31이며, D28및 D29는 각각 C1-4알킬이고, D30은 수소, C1-4알킬 또는 C1-4알킬술폰일이고, D31은 C1-4알킬이며, D32는 C1-6알킬이고, D36및 D37은 각각 독립적으로 수소 또는 C1-6알킬이고, D38은 수소, C1-6알킬, C1-4알콕실, C1-4알콕시-카르보닐, 메르캅토, 히드록실, C1-3알콕시-C1-2알킬, C1-4알킬아미노, ND28(D29), CONHSO2CH3또는 N(D39)-SO2D31이며, D39는 수소, C1-4알킬 또는 C1-4알킬술폰일이고, D47및 D48은 각각 독립적으로 수소 또는 C1-4알킬이고, (ii) R5와 D1이 고리를 형성하는 경우, 상기 우라실 유도체는 일반식D 21 is hydrogen, methyl, methoxy or methoxymethyl, D 22 is hydrogen, C 1-4 alkyl, C 3-6 cycloalkyl or benzyl, D 23 is hydrogen or methyl, and D 24 is hydrogen , Methyl or methoxymethyl, Z is oxygen, sulfur or NH, D 25 is hydrogen, C 1-4 alkyl, C 2-5 alkenyl, C 3-5 alkynyl, or C 1-4 alkylsulfonyl D 26 is C 1-4 alkyl, D 27 is hydrogen, C 1-6 alkyl, C 1-4 alkoxyl, C 1-4 alkoxy-carbonyl, mercapto, hydroxyl, C 1-3 alkoxy -C 1-2 alkyl, C 1-4 alkylamino, ND 28 (D 29 ), dimethylcarbamoyl, CONHSO 2 CH 3 or N (D 30 ) SO 2 D 31 , wherein D 28 and D 29 are each C 1-4 alkyl, D 30 is hydrogen, C 1-4 alkyl or C 1-4 alkylsulfonyl, D 31 is C 1-4 alkyl, D 32 is C 1-6 alkyl, D 36 and D 37 is each independently hydrogen or C 1-6 alkyl, D 38 is hydrogen, C 1-6 alkyl, C 1-4 alkoxyl, C 1-4 alkoxy-carbonyl, mercapto, hydroxyl, C 1-3 alkoxy-C 1-2 alkyl, C 1-4 alkylamino, ND 28 (D 29 ), CONHSO 2 CH 3 or N (D 39 ) -SO 2 D 31 , D 39 is hydrogen, C 1- 4 alkyl or C 1-4 alkylsulfonyl, D 47 and D 48 are each independently hydrogen or C 1-4 alkyl, and (ii) when R 5 and D 1 form a ring, the uracil derivatives are expression

Figure kpo00052
Figure kpo00052

Figure kpo00053
Figure kpo00053

Figure kpo00054
Figure kpo00054

이고, J는 수소, C1-4알킬, C2-4알켄일, C3-4알킨일, 히드록시메틸, 클로로메틸, 카르바모일메틸, 시아노메틸, C1-4알콕시-카르보닐메틸,

Figure kpo00055
, C3-6시클로알킬, C3-6시클로알킬-C1-2알킬, C1-2알콕시-C1-2알킬; 또는 C1-4알킬, C1-4알콕실, C1-4알콕시-카르보닐, 메톡시메틸 또는 할로겐에 의해 치환될 수 있는 벤질이다.And J is hydrogen, C 1-4 alkyl, C 2-4 alkenyl, C 3-4 alkynyl, hydroxymethyl, chloromethyl, carbamoylmethyl, cyanomethyl, C 1-4 alkoxy-carbonyl methyl,
Figure kpo00055
, C 3-6 cycloalkyl, C 3-6 cycloalkyl-C 1-2 alkyl, C 1-2 alkoxy-C 1-2 alkyl; Or benzyl which may be substituted by C 1-4 alkyl, C 1-4 alkoxyl, C 1-4 alkoxy-carbonyl, methoxymethyl or halogen.

일반식(II'), (III') 및 (IV')의 화합물 중에서, 하기가 더욱 바람직하다.Among the compounds of the general formulas (II ′), (III ′) and (IV ′), the following are more preferred.

하기 일반식(II)의 우라실 유도체:Uracil derivatives of the general formula (II)

Figure kpo00056
Figure kpo00056

상기 식에서, R1은 수소 또는 메틸이고, R2는 C1-2할로알킬이고, R4는 수소 또는 플루오르이며, A2는 수소, C1-5알킬, C2-5알켄일, C3-5알킨일, 시아노메틸, 메톡시메틸, -CH2CONH2; C1-4알킬, 트리플루오로메틸, 메톡시 또는 할로겐에 의해 치환될 수 있는 벤질; 또는 -CH2A24이고, A24는 2-피리딜이다.Wherein R 1 is hydrogen or methyl, R 2 is C 1-2 haloalkyl, R 4 is hydrogen or fluorine, A 2 is hydrogen, C 1-5 alkyl, C 2-5 alkenyl, C 3 -5 alkynyl, cyanomethyl, methoxymethyl, -CH 2 CONH 2 ; Benzyl which may be substituted by C 1-4 alkyl, trifluoromethyl, methoxy or halogen; Or -CH 2 A 24 , A 24 is 2-pyridyl.

하기 일반식(III)의 우라실 유도체:Uracil derivatives of the general formula (III)

Figure kpo00057
Figure kpo00057

상기 식에서, R1은 수소 또는 메틸이고, R2는 C1-2할로알킬이고, R4는 수소 또는 플루오르이며, R5는 염소이고, B1은 수소, C1-5알킬, C3-6시클로알킬, C2-4알켄일, C3-4알킨일, 벤질, 또는

Figure kpo00058
이며, B21은 수소 또는 메틸이고, B22은 수소, C1-5알킬, C2-5알켄일, C3-5알킨일, C3-6시클로알킬 또는 벤질이다.Wherein R 1 is hydrogen or methyl, R 2 is C 1-2 haloalkyl, R 4 is hydrogen or fluorine, R 5 is chlorine, B 1 is hydrogen, C 1-5 alkyl, C 3- 6 cycloalkyl, C 2-4 alkenyl, C 3-4 alkynyl, benzyl, or
Figure kpo00058
And B 21 is hydrogen or methyl and B 22 is hydrogen, C 1-5 alkyl, C 2-5 alkenyl, C 3-5 alkynyl, C 3-6 cycloalkyl or benzyl.

하기 일반식(IV)의 우라실 유도체:Uracil derivatives of the general formula (IV)

Figure kpo00059
Figure kpo00059

상기 식에서, R1은 수소 또는 메틸이고, R2는 C1-2할로알킬이고, R4는 수소, 또는 플루오르이며, (i) R5와 D1을 개별적으로 취한 경우, R5는 염소이고, D1Wherein R 1 is hydrogen or methyl, R 2 is C 1-2 haloalkyl, R 4 is hydrogen or fluorine, and (i) when R 5 and D 1 are taken separately, R 5 is chlorine , D 1

Figure kpo00060
Figure kpo00060

이며, D27은 C1-6알킬이고, (ii) R5와 D1이 고리를 형성하는 경우, 상기 우라실 유도체는 일반식And D 27 is C 1-6 alkyl and (ii) when R 5 and D 1 form a ring, the uracil derivative is of the general formula

Figure kpo00061
Figure kpo00061

Figure kpo00062
Figure kpo00062

Figure kpo00063
Figure kpo00063

이고, J는 수소, C1-4알킬, C2-4알켄일, C3-4알킨일, 시아노메틸,

Figure kpo00064
, C1-2알콕시-C1-2알킬; 또는 C1-4알킬, 메톡시 또는 할로겐으로 치환될 수 있는 벤질이다.J is hydrogen, C 1-4 alkyl, C 2-4 alkenyl, C 3-4 alkynyl, cyanomethyl,
Figure kpo00064
, C 1-2 alkoxy-C 1-2 alkyl; Or benzyl, which may be substituted with C 1-4 alkyl, methoxy or halogen.

본 발명의 화합물 중에서, 화합물 번호 A-1 내지 A-33, B-1, B-2 및 C-1 내지 C-3이 제초제의 활성성분으로서 사용하기에 특히 바람직하다.Among the compounds of the present invention, compound numbers A-1 to A-33, B-1, B-2 and C-1 to C-3 are particularly preferred for use as active ingredients of herbicides.

본 발명의 우라실 유도체는 하기 반응 도식에 따라 합성될 수 있다.The uracil derivatives of the present invention can be synthesized according to the following reaction scheme.

Figure kpo00065
Figure kpo00065

Figure kpo00066
Figure kpo00066

Figure kpo00067
Figure kpo00067

Figure kpo00068
Figure kpo00068

Figure kpo00069
Figure kpo00069

(1) 도식 1에서는, 제1단계에서 β-아미노아크릴산 에스테르(V)와 페닐 이소(티오)시아네이트(VI)를 반응시켜 우라실 유도체(I')를 생성시키고 제2단계에서 상기 유도체(I')를 단리한 후 또는 단리하지 않고 그 우라실 고리의 1-위치를 알킬화시켜 일반식(I)의 우라실 유도체를 생성시킨다.(1) In Scheme 1, β-aminoacrylic acid ester (V) and phenyl iso (thio) cyanate (VI) are reacted in the first step to produce uracil derivative (I '), and in the second step, the derivative (I) After isolating ') or without isolation, the 1-position of the uracil ring is alkylated to give the uracil derivative of formula (I).

[제1단계에서의 반응][Reaction in Step 1]

페닐 이소(티오)시아네이트(VI)는 β-아미노아크릴산 에스테르(V)에 대해 통상 0.5 내지 1.5당량, 바람직하게는 0.9 내지 1.1당량으로 사용된다.Phenyl iso (thio) cyanate (VI) is usually used in 0.5 to 1.5 equivalents, preferably 0.9 to 1.1 equivalents, relative to the β-aminoacrylic acid ester (V).

반응은 용매 없이 진행될 수 있으나, 통상적으로 반응을 촉진하기 위하여 용매를 사용한다. 이 반응에서의 상기 목적에 사용할 수 있는 용매로서는 헥산, 헵탄, 리그로인 및 석유 에테르 같은 지방족 탄화수소; 벤젠, 톨루엔, 크실렌 및 클로로벤젠 같은 방향족 탄화수소; 클로로포름 및 메틸렌 클로라이드 같은 할로겐화 탄화수소; 디에틸 에테르, 디옥산 및 테트라히드로푸란 같은 에테르; 아세톤 및 메틸 에틸 케톤 같은 케톤; 아세토니트릴 및 이소부티로니트릴 같은 니트릴; 피리딘 및 N,N-디에틸아닐린 같은 3급 아민; 포름아미드, N,N-디메틸포름아미드 및 N-메틸피롤리돈 같은 산 아미드; 디메틸 술폭시드 및 술폴란 같은 황-함유 화합물; 및 이들의 혼합물을 그 예로 들 수 있다. 이중에서, 지방족 탄화수소, 산 아미드, 황-함유 화합물 및 이들의 혼합물이 바람직하다.The reaction can proceed without solvent, but usually a solvent is used to promote the reaction. Solvents usable for this purpose in this reaction include aliphatic hydrocarbons such as hexane, heptane, ligroin and petroleum ether; Aromatic hydrocarbons such as benzene, toluene, xylene and chlorobenzene; Halogenated hydrocarbons such as chloroform and methylene chloride; Ethers such as diethyl ether, dioxane and tetrahydrofuran; Ketones such as acetone and methyl ethyl ketone; Nitriles such as acetonitrile and isobutyronitrile; Tertiary amines such as pyridine and N, N-diethylaniline; Acid amides such as formamide, N, N-dimethylformamide and N-methylpyrrolidone; Sulfur-containing compounds such as dimethyl sulfoxide and sulfolane; And mixtures thereof. Of these, aliphatic hydrocarbons, acid amides, sulfur-containing compounds and mixtures thereof are preferred.

염기를 사용하지 않고서도 반응시킬 수 있지만, 일반적으로 염기는 β-아미노아크릴산 에스테르(V)에 대해 0.5 내지 10당량, 바람직하게는 1.0 내지 2.0당량이 사용된다. 염기로서 예컨대 피리딘, 트리에티랑민 및 1,4-디아자비시클로-2,2,2-옥탄 같은 질소-함유 유기 염기; 수소화나트륨, 수소화칼륨, 수산화나트륨, 수산화칼륨, 탄산나트륨 및 탄산칼륨 같은 무기염기; 메톡시화나트륨, 에톡시화나트륨 및 3급-부톡시화칼륨 같은 금속 알코올레이트를 사용할 수 있다 이중에서, 수소화나트륨, 수산화나트륨 및 수산화칼륨이 바람직하다.Although the reaction can be carried out without using a base, in general, 0.5 to 10 equivalents, preferably 1.0 to 2.0 equivalents, are used for the β-aminoacrylic acid ester (V). Bases such as nitrogen-containing organic bases such as pyridine, triethyramine and 1,4-diazabicyclo-2,2,2-octane; Inorganic bases such as sodium hydride, potassium hydride, sodium hydroxide, potassium hydroxide, sodium carbonate and potassium carbonate; Metal alcoholates such as sodium methoxide, sodium ethoxylate and tert-butoxylate can be used, of which sodium hydride, sodium hydroxide and potassium hydroxide are preferred.

반응온도는 통상 -40 내지 200℃, 바람직하게는 상온 내지 반응혼합물의 환류온도이다.The reaction temperature is usually -40 to 200 ° C, preferably room temperature to reflux temperature of the reaction mixture.

반응시간은 통상 10분 내지 72시간, 바람직하게는 30분 내지 24시간이다.The reaction time is usually 10 minutes to 72 hours, preferably 30 minutes to 24 hours.

반응이 종결된 후, 무기산(mineral acid, 예:염산) 또는 유기산(예:아세트산, 트리플루오로아세트산, p-톨루엔술폰산 등)을 사용하여 반응생성물을 산성으로 만듦으로써 유도체(I')를 단리할 수 있다.After the reaction is completed, the derivative (I ') is isolated by making the reaction product acidic using inorganic acid (e.g. hydrochloric acid) or organic acid (e.g. acetic acid, trifluoroacetic acid, p-toluenesulfonic acid, etc.). can do.

[제2단계에서의 반응][Reaction in Step 2]

반응의 제2단계에서는 알킬화제를 유도체(I')에 대해 1.0 내지 10당량, 바람직하게는 1.0 내지 5.0당량으로 사용하여 유도체(I')를 알킬화시킨다. 알킬화제로서는 예컨대 디메틸황산 및 디에틸황산 같은 알킬황산; 메틸 클로라이드, 에틸 클로라이드, 메틸 브로마이드, 에틸 브로마이드, 메틸 아이오다이드 및 에틸 아이오다이드 같은 알킬 할라이드를 사용할 수 있다.In the second stage of the reaction, the alkylating agent is alkylated using an alkylating agent in an amount of 1.0 to 10 equivalents, preferably 1.0 to 5.0 equivalents, relative to the derivative (I '). Alkylating agents include, for example, alkylsulfuric acids such as dimethylsulfuric acid and diethylsulfuric acid; Alkyl halides such as methyl chloride, ethyl chloride, methyl bromide, ethyl bromide, methyl iodide and ethyl iodide can be used.

용매 없이도 반응을 진행시킬 수 있으나, 통상적으로 반응을 촉진시키기 위하여 용매를 사용한다. 상기 반응에서의 상기 목적에 사용할 수 있는 용매로서 헥산, 헵탄, 리그로인 및 석유 에테르 같은 지방족 탄화수소; 벤젠, 톨루엔, 크실렌 및 클로로벤젠 같은 방향족 탄화수소; 클로로포름 및 메틸렌 클로라이드 같은 할로겐화 탄화수소; 디에틸 에테르, 디옥산 및 테트라히드로푸란 같은 에테르; 아세톤 및 메틸 에틸 케톤 같은 케톤; 아세토니트릴 및 이소부티로니트릴 같은 니트릴; 피리딘 및 N,N-디에틸아닐린 같은 3급 아민; 포름아미드, N,N-디메틸포름아미드 및 N-메틸피롤리돈 같은 산 아미드; 디메틸 술폭시드 및 술폴란 같은 황-함유 화합물; 물 및 이들의 혼합물을 예로 들 수 있다. 이들 중에서, 지방족 탄화수소, 산 아미드, 황-함유 화합물 및 이들의 혼합물이 바람직하다.The reaction can proceed without the solvent, but usually a solvent is used to promote the reaction. As a solvent which can be used for this purpose in the said reaction, Aliphatic hydrocarbons, such as hexane, heptane, ligroin, and a petroleum ether; Aromatic hydrocarbons such as benzene, toluene, xylene and chlorobenzene; Halogenated hydrocarbons such as chloroform and methylene chloride; Ethers such as diethyl ether, dioxane and tetrahydrofuran; Ketones such as acetone and methyl ethyl ketone; Nitriles such as acetonitrile and isobutyronitrile; Tertiary amines such as pyridine and N, N-diethylaniline; Acid amides such as formamide, N, N-dimethylformamide and N-methylpyrrolidone; Sulfur-containing compounds such as dimethyl sulfoxide and sulfolane; Water and mixtures thereof are exemplified. Of these, aliphatic hydrocarbons, acid amides, sulfur-containing compounds and mixtures thereof are preferred.

상기 반응에서, 염기는 유도체(I')에 대해 통상 1.0 내지 10당량, 바람직하게는 1.0 내지 2.0당량으로 사용된다. 염기로서, 피리딘, 트리에틸아민 및 1,4-디아자비시클로-2,2,2-옥탄 같은 질소-함유 유기 염기; 수소화나트륨, 수소화칼륨, 수산화나트륨, 수산화칼륨, 탄산나트륨 및 탄산칼륨 같은 무기염기를 사용할 수 있다. 이중에서 수소화나트륨 및 탄산칼륨 같은 무기염기가 바람직하다.In this reaction, the base is usually used in an amount of 1.0 to 10 equivalents, preferably 1.0 to 2.0 equivalents, relative to derivative (I ′). As the base, nitrogen-containing organic bases such as pyridine, triethylamine and 1,4-diazabicyclo-2,2,2-octane; Inorganic bases such as sodium hydride, potassium hydride, sodium hydroxide, potassium hydroxide, sodium carbonate and potassium carbonate can be used. Of these, inorganic bases such as sodium hydride and potassium carbonate are preferred.

반응온도는 통상 0 내지 150℃, 바람직하게는 상온 내지 반응혼합물의 환류온도이다.The reaction temperature is usually from 0 to 150 캜, preferably from room temperature to the reflux temperature of the reaction mixture.

반응시간은 통상 10분 내지 96시간, 바람직하게는 30분 내지 48시간이다.The reaction time is usually 10 minutes to 96 hours, preferably 30 minutes to 48 hours.

(2) 도식 2에 따라, 제1단계에서 N-페닐 카르바메이트(VII)를 β-아미노아크릴산 에스테르(V)와 반응시켜 우라실 유도체(I')를 생성시키고, 유도체(I')를 단리한 후 또는 단리하지 않고 제2단계에서 그 우라실 고리의 1-위치를 알킬화시켜 일반식(I)의 우라실 유도체를 제조한다.(2) According to Scheme 2, in the first step, N-phenyl carbamate (VII) is reacted with β-aminoacrylic acid ester (V) to produce uracil derivative (I '), and derivative (I') is isolated. The uracil derivatives of general formula (I) are prepared by alkylating the 1-position of the uracil ring after this or without isolation in a second step.

[제1단계에서의 반응][Reaction in Step 1]

N-페닐 카르바메이트(VII)는 β-아미노 아크릴산 에스테르(V)에 대해 0.5 내지 1.5당량, 바람직하게는 0.9 내지 1.1당량으로 사용된다.N-phenyl carbamate (VII) is used in 0.5 to 1.5 equivalents, preferably 0.9 to 1.1 equivalents relative to β-amino acrylic acid ester (V).

일반적으로 반응에는 용매가 필요하다. 용매로서는 예컨대 헥산, 헵탄, 리그로인 및 석유 에테르 같은 지방족 탄화수소; 벤젠, 톨루엔, 크실렌 및 클로로벤젠 같은 방향족 탄화수소; 클로로포름 및 메틸렌 클로라이드 같은 할로겐화 탄화수소; 디에틸 에테르, 디옥산 및 테트라히드로푸란 같은 에테르; 아세톤 및 메틸 에틸 케톤 같은 케톤; 아세토니트릴 및 이소부티로니트릴 같은 니트릴; 피리딘 및 N,N-디에틸아닐린 같은 3급 아민; 포름아미드, N,N-디메틸포름아미드 및 N-메틸피롤리돈 같은 산 아미드; 디메틸 술폭시드 및 술폴란 같은 황-함유 화합물;메탄올, 에탄올, 프로판올 및 부탄올 같은 알코올; 물; 및 이들의 혼합물을 사용할 수 있다. 이들 중에서, 지방족 탄화수소, 산 아미드, 황-함유 화합물 및 이들의 혼합물이 바람직하다.In general, the reaction requires a solvent. Examples of the solvent include aliphatic hydrocarbons such as hexane, heptane, ligroin and petroleum ether; Aromatic hydrocarbons such as benzene, toluene, xylene and chlorobenzene; Halogenated hydrocarbons such as chloroform and methylene chloride; Ethers such as diethyl ether, dioxane and tetrahydrofuran; Ketones such as acetone and methyl ethyl ketone; Nitriles such as acetonitrile and isobutyronitrile; Tertiary amines such as pyridine and N, N-diethylaniline; Acid amides such as formamide, N, N-dimethylformamide and N-methylpyrrolidone; Sulfur-containing compounds such as dimethyl sulfoxide and sulfolane; alcohols such as methanol, ethanol, propanol and butanol; water; And mixtures thereof. Of these, aliphatic hydrocarbons, acid amides, sulfur-containing compounds and mixtures thereof are preferred.

상기 반응에서, 염기는 β-아미노아크릴산 에스테르(V)에 대해 통상 0.5 내지 10당량, 바람직하게는 1.0 내지 2.0당량으로 사용된다. 상기 반응에 사용할 수 있는 염기는 수소화나트륨, 수소화칼륨, 수산화나트륨, 수산화칼륨, 탄산나트륨 및 탄산칼륨 같은 무기염기; 메톡시화나트륨, 에톡시화나트륨 및 3급-부톡시화칼륨 같은 금속 알코올레이트; 및 나트륨 메틸 메르캅티드 및 나트륨 에틸 메르캅티드 같은 금속 알킬 메르캅티드를 포함한다. 이들 중에서, 수소화나트륨 같은 무기염기와 메톡시화나트륨 같은 금속 알코올레이트가 바람직하다.In this reaction, the base is usually used in 0.5 to 10 equivalents, preferably 1.0 to 2.0 equivalents, relative to the β-aminoacrylic acid ester (V). Bases that can be used for the reaction include inorganic bases such as sodium hydride, potassium hydride, sodium hydroxide, potassium hydroxide, sodium carbonate and potassium carbonate; Metal alcoholates such as sodium methoxylated, sodium ethoxylated and tert-butoxylated; And metal alkyl mercaptides such as sodium methyl mercaptide and sodium ethyl mercaptide. Among them, inorganic bases such as sodium hydride and metal alcoholates such as sodium methoxide are preferable.

반응은 통상 0 내지 200℃, 바람직하게는 상온 내지 반응 혼합물의 환류온도에서 행해진다.The reaction is usually carried out at 0 to 200 ° C, preferably at room temperature to the reflux temperature of the reaction mixture.

반응시간은 통상 10분 내지 72시간, 바람직하게는 30분 내지 12시간이다.The reaction time is usually 10 minutes to 72 hours, preferably 30 minutes to 12 hours.

반응이 종결된 후, 무기산(예:염산)또는 유기산(예:아세트산, 트리플루오로아세트산 및 p-톨루엔술폰산)으로 산성화시킴으로써 반응 혼합물로부터 유도체(I')를 단리할 수 있다.After the reaction is complete, the derivative (I ′) can be isolated from the reaction mixture by acidifying with an inorganic acid (eg hydrochloric acid) or an organic acid (eg acetic acid, trifluoroacetic acid and p-toluenesulfonic acid).

[제2단계에서의 반응][Reaction in Step 2]

도식 1의 제2단계에서와 동일한 반응 조건하에서 유도체(I')를 알킬화시킨다.The derivative (I ′) is alkylated under the same reaction conditions as in the second step of Scheme 1.

(3) 도식 3에서는 단일 단계에서 페닐 이소(티오)시아네이트(VI)를 N-치환된 β-아미노아크릴산 에스테르(VIII)와 반응시켜 일반식(I)의 우라실 유도체를 제조한다. 도식 1에서 이용한 것과 동일한 반응조건을 이용할 수 있다.(3) In Scheme 3, phenyl iso (thio) cyanate (VI) is reacted with N-substituted β-aminoacrylic acid ester (VIII) in a single step to prepare uracil derivatives of general formula (I). The same reaction conditions as those used in Scheme 1 can be used.

(4) 도식 4에서는 단일단계에서 N-페닐 카르바메이트(VII)를 N-치환된 β-아미노아크릴산 에스테르(VIII)와 반응시켜 일반식(I)의 우라실 유도체를 제조한다. 도식 2에서 이용한 것과 동일한 반응 조건 하에서 반응을 행할 수 있다.(4) In Scheme 4, N-phenyl carbamate (VII) is reacted with N-substituted β-aminoacrylic acid ester (VIII) in a single step to prepare uracil derivatives of general formula (I). The reaction can be carried out under the same reaction conditions as those used in Scheme 2.

본 발명의 우라실 유도체는 토양처리 또는 엽면처리를 통해 산지, 논 및 비경지용 제초제로서 투여될 수 있다. 또한 이들은 낮은 투여량으로도 예컨대 하기와 같은 잡초에 대해 높은 제초 활성을 나타낸다:솔라늄 니그룸(Solanum nigrum) 및 다투라 니그룸(Datura nigrum) 같은 가지과(Solanaceae) 잡초, 아부틸론 테오프라스티(Abutilon theophrasti) 및 시드 스피노사(Side spinosa) 같은 아욱과(Malvaceae) 잡초, 이포모에아(Ipomoea)종[예:이포모에아 푸르푸레아(Ipomoea purpurea)] 및 칼리스테기아(Calystegia)종 같은 메꽃과(Convolvulaceae) 잡초, 아마란투스 리비두스(Amaranthus lividus) 및 아마란투스 레트로플렉수스(Amaranthus retroflexus) 같은 비름과(Amaranthaceae) 잡초, 크산티움 펜실바니쿰(Xantbium pensylvanicum), 암브로시아 아르테미시아에폴리아(Ambrosia artemisiaefolia), 헬리안투스 안누스(Helianthus annuus), 갈린소가 실리아타(Galinsoga ciliata), 시르슘 아르벤스(Cirsium arvense), 세네시오 불가리스(Senecio vulgaris) 및 에리게론 안누스(Erigeron annus) 같은 콤포지타에(Compositae) 잡초, 로리파 인디카(Rorippa indica), 시나피스 아르벤시스(Sinapis arvensis) 및 캅셀라 부르사파스트리스(Capsella bursapastris) 같은 겨자과(Crucifereae) 잡초, 폴리고눔 블루메(Polygonum blume) 및 폴리고눔 콘볼불루스(Polygonum convolvulus) 같은 폴리조나세아에(Polyzonaceae) 잡초, 포르툴라카 올레라세아(Portulaca oleracea) 같은 쇠비름과(Portulacaceae) 잡초, 케노포듐 알붐(Chenopodium album), 케노포듐 피시폴륨(Chenopodium ficifolium) 및 코키아스 코파리아(Kochias coparia) 같은 명아주과(Chenopodiaceae) 잡초, 스텔라리아 메디아(Stellaria media) 같은 카리오필라세아에(Caryophyllaceae) 잡초, 베로니카 페르시카(Veronica persica) 같은 현삼과(Scrophulariaceae) 잡초, 콤멜리나 콤무니스(Commelina communis) 같은 닭의 장풀과(Commelinaceae) 잡초, 라미움 암플렉시카울레(Lamium amplexicaule) 및 라미움 푸르푸레움(Lamium purpureum) 같은 꿀풀과(Labiatae) 잡초, 유포르비아 수피나(Euphorbia supina) 및 유포르비아 마쿨라타(Euphorbia maculata) 같은 대극과(Euphorbiaceae) 잡초, 갈륨 스푸륨(Galium spurium), 갈륨 아파리네(Galium aparine) 및 루비아칸(Rubiaakane) 같은 꼭두서니과(Rubiaceae) 잡초, 비올라 아르벤시스(Viola arvensis) 같은 제비꽃과(Violaceae) 잡초, 세르바니아 엑살타타(Sesbania exaltata) 및 카씨아 오브투시폴리아(Cassia obtusifolia) 같은 콩과(Leguminosae) 잡초 등의 활엽 잡초; 소르감 비콜로르(Sorgham bicolor), 파니쿰 디코토미플로룸(Panicum dichotomiflorum), 소르품 할레펜세(Sorphum halepense), 에키노클로아 크루스-갈리(Echinochloa crus-galli), 디기타리아 아드센덴스(Digitaria adscendens), 아베나 파투아(Avena fatua), 엘류시네 인디카(Eleusine indica), 세타리아 비리디스(Setaria viridis) 및 알루페쿠루스 아에콸리스(Alopecurus aequalis) 같은 포아풀과 잡초; 시페루스 로툰두스(Cyperus rotundus) 같은 방동사니과 잡초; 및 알리스마 카날리쿨라툼(Alisma canaliculatum), 사기타리아 트리폴리아(Sagittaria trifolia) 및 사기타리아 피그마에아(Sagittaria pygmaea) 같은 택사과(Alismataceae) 잡초, 시페루스 디포르미스(Cyperus difformis), 시페루스 세로티누스(Cyperus serotinus), 씨르푸스 준코이데스(Scirpus juncoides) 및 엘레오카리스 쿠로구와이(Eleocharis kuroguwai) 같은 방동사니과(Cyperaceae) 잡초, 린데미아 픽시다리아(Lindemia pyxidaria) 같은 스크로툴라리아세아에(Scrothulariaceae) 잡초, 모노코리아 바기날리스(Monochoria vaginalis) 같은 포텐데리아세아에(Potenderiaceae) 잡초, 포타모게톤 디스틴크투스(Potamogeton distinctus) 같은 가래과(Potamogetonaceae) 잡초, 로탈라 인디카(Rotala indica) 같은 부처꽃과(Lythraceae) 잡초 및 에키노클로아 크루스-갈리(Echinochloa crus-galli) 같은 포아풀과(Gramineae) 잡초 등의 논 잡초. 또한 본 발명의 우라실 유도체가 밀, 옥수수, 보리, 대두, 벼, 목화, 사탕수수 및 소금(sorghum) 같은 중요한 농작물에 해를 끼치지 않는다는 것도 두드러진다.The uracil derivatives of the present invention can be administered as herbicides for mountainous, paddy, and parentage lands through soil treatment or foliar treatment. They also show high herbicidal activity at low doses, for example against the following weeds: Solanaceae weeds such as Solanum nigrum and Datura nigrum, Abutlon teoplasti Malvaceae weeds, such as Abutilon theophrasti and Seed spinosa, Ipomoea species (eg, Ipomoea purpurea), and calendulas such as Calistegia species Amaranthaceae weeds such as Convolvulaceae weeds, Amaranthus lividus and Amaranthus retroflexus, Xantbium pensylvanicum, Ambrosia Artemisia efolia ( Ambrosia artemisiaefolia, Helianthus annuus, Galinsoga ciliata, Cisium arvense, Senesio vulgaris and Erice Compositeae weeds, such as the Erwinon annus, mustard plants such as Rorippa indica, Sinapis arvensis, and Capsella bursapastris, and polygonum. Polyzonaceae weeds such as Polygonum blume and Polygonum convolvulus, Purslane and Wenopodium album, such as Portulaca oleracea ), Chenopodiaceae weeds, such as Kenopodium ficifolium and Kochias coparia, Caryophyllaceae weeds such as Stellaria media, Veronica persica ) Scrophulariaceae weeds, Commelinaceae weeds such as Commelina commelina communis, Lamium amflexiuale Labiatae weeds such as plexicaule and Lamium purpureum, Euphorbia supina and Euphorbia maculata, Euphorbiaaceae weeds, and Galium spurium ), Rubiaceae weeds, such as Gallium aparine and Rubiaakane, Violaceae weeds such as Viola arvensis, Serbania exaltata and Cassia orb Broad-leaved weeds such as Leguminosae weeds, such as Cassia obtusifolia; Sorgham bicolor, Panicum dichotomiflorum, Sorphum halepense, Echinochloa crus-galli, Digitaria Adsendens Poop grasses and weeds such as Digitaria adscendens, Avena fatua, Eleusine indica, Setaria viridis, and Alopecurus aequalis; Roomworms and weeds such as Cyperus rotundus; And Alismataceae weeds such as Alisma canaliculatum, Sagittaria trifolia and Sagittaria pygmaea, Cyperus difformis. Scrotulans, such as Cyperaceae weeds such as Cyperus serotinus, Scirpus juncoides, and Eleocharis kuroguwai, and Lindemia pyxidaria. Scrothulariaceae weeds, Potenderiaceae weeds like Monochoria vaginalis, Potatogegeton distinctus weeds, Potamogetonaceae weeds, Rotala indica Paddy weeds such as Lythraceae weeds, such as indica, and Gramineae weeds, such as Echinochloa crus-galli. It is also prominent that the uracil derivatives of the present invention do not harm important crops such as wheat, corn, barley, soybean, rice, cotton, sugar cane and salt (sorghum).

본 발명의 우라실 유도체는 낙엽제(defoliant)로서도 유용하다.The uracil derivatives of the present invention are also useful as defoliants.

본 발명에 따른 화합물을 제초제로서 사용하는 경우, 이들은 통상 담체, 예컨대 진흙, 활석, 벤토나이트, 규조토 및 화이트 카본(미세한 실리카 분말) 같은 고체 담체, 또는 물, 알코올(이소프로판올, 부탄올, 벤질 알코올, 푸르푸릴 알코올 등), 방향족 탄화수소(톨루엔, 크실렌 등), 에테르(아니솔 등), 케톤(시클로헥산온, 이소포론 등), 에스테르(부틸 아세테이트 등), 산 아미드(N-메틸피롤리돈 등) 및 할로겐화 탄소(클로로벤젠 등) 같은 액체 담체와 혼합된다. 또한 필요한 경우, 계면활성제, 유화제, 분산제, 침투제, 전착제(spreader), 증점제, 동결방지제, 응고방지제, 안정화제 등과 같은 적합한 보조제를 첨가할 수 있으며, 액체 제제, 유화농축액, 습윤성분말, 무수유동제, 유동제, 살포제 및 과립제 같은 다양한 제형으로 실제용도에 제공될 수 있다.When the compounds according to the invention are used as herbicides, they are usually carriers, for example solid carriers such as mud, talc, bentonite, diatomaceous earth and white carbon (fine silica powder), or water, alcohols (isopropanol, butanol, benzyl alcohol, furfuryl Alcohols, etc.), aromatic hydrocarbons (toluene, xylenes, etc.), ethers (anisoles, etc.), ketones (cyclohexanone, isophorone, etc.), esters (butyl acetate, etc.), acid amides (such as N-methylpyrrolidone), and Mixed with a liquid carrier such as halogenated carbon (chlorobenzene, etc.). If necessary, suitable auxiliaries such as surfactants, emulsifiers, dispersants, penetrants, spreaders, thickeners, cryoprotectants, anticoagulants, stabilizers and the like may be added, and liquid preparations, emulsion concentrates, wetting ingredients, anhydrous agents Various formulations can be provided for practical use, such as flow agents, sprays and granules.

필요한 경우 제조중에 또는 제제 투여시에, 본 발명의 화합물을 다른 종류의 제초제, 각종 살충제, 살진균제, 식물 생장 조절제, 상승제(相昇劑) 등과 혼합할 수 있다.If necessary, during preparation or administration of the formulation, the compounds of the present invention may be mixed with other types of herbicides, various insecticides, fungicides, plant growth regulators, synergists and the like.

본 발명에 따른 화합물의 사용시 혼합될 수 있는 제초제의 종류로서는 예컨대 Farm Chemicals Handbook(1989)에 기재되어 있는 화합물을 언급할 수 있다.As a class of herbicides which can be mixed in the use of the compounds according to the invention, mention may be made of the compounds described in, for example, Farm Chemicals Handbook (1989).

본 발명에 따른 화합물의 투여율은 투여장소, 투여시간, 투여방법, 처리되는 농작물의 종류 등에 따라 달라지지만, 본 발명의 화합물을 활성성분 기준으로 통상 약 0.0001 내지 10kg/ha, 바람직하게는 0.001 내지 5kg/ha만큼 투여하는 것이 적합하다.The dosage rate of the compound according to the present invention depends on the place of administration, the time of administration, the method of administration, the type of crops to be treated, etc., but the compound of the present invention is usually about 0.0001 to 10 kg / ha, preferably 0.001 to 10 based on the active ingredient It is suitable to administer as much as 5kg / ha.

기존의 제초제와 비교하여 본 발명의 화합물은 매우 낮은 투여랑에서도 신속하고 높은 제초효과를 가지며 토양처리 또는 엽면처리를 통해 광범위한 잡초에 투여될 수 있다.Compared with conventional herbicides, the compounds of the present invention have a rapid and high herbicidal effect even at very low dose levels and can be administered to a wide range of weeds through soil treatment or foliar treatment.

하기 실시예에서 본 발명을 더욱 상세하게 설명하지만 본 발명의 영역이 이들 실시예로 한정되는 것은 아니다.The present invention is explained in more detail in the following Examples, but the scope of the present invention is not limited to these Examples.

[실시예 A-1]Example A-1

3-(7-플루오로-3-옥소-4-프로파르길-2H-1,4-벤조옥사진-6-일)-1-메틸-6-트리플루오로메틸-2,4(1H,3H)-피리미딘디온(화합물 A-1)의 합성3- (7-fluoro-3-oxo-4-propargyl-2H-1,4-benzooxazin-6-yl) -1-methyl-6-trifluoromethyl-2,4 (1H, Synthesis of 3H) -pyrimidinedione (Compound A-1)

Figure kpo00070
Figure kpo00070

상온에서, 수소화나트륨(순도:55%) 0.02g이 현탁된 디메틸포름아미드 용액(2ml)에 3-(7-플루오로-3-옥소-4-프로파르길-2H-1,4-벤조옥사진-6-일)-6-트리플루오로메틸-2,4(1H,3H)-피리미딘디온 0.18g을 첨가하였다. 20분동안 정치시킨 후, 디메틸황산 0.09g을 용액에 더 첨가하고 하룻밤동안 교반하였다. 디메틸포름아미드를 증류해내고 물을 첨가하여 잔류물을 에틸 아세테이트로 추출하였다. 염화나트륨 포화 수용액으로 추출물을 세척하고 무수 황산나트륨 상에서 건조시킨 후 에틸 아세테이트를 증류해내어 조 생성물을 수득하였다. 전개용매로서 헥산/에틸 아세테이트(3:1)를 사용하는 예비 박층 크로마토그래피에 의해 조 생성물을 정제하여 무색 점성 오일 형태의 목적 화합물 0.15g을 수득하였다. 그대로 방치하였을 때 응고되었다.At room temperature, in a solution of dimethylformamide (2 ml) in which 0.02 g of sodium hydride (purity: 55%) was suspended, 3- (7-fluoro-3-oxo-4-propargyl-2H-1,4-benzooxane Photo-8-yl) -6-trifluoromethyl-2,4 (1H, 3H) -pyrimidinedione 0.18 g was added. After standing for 20 minutes, 0.09 g of dimethyl sulfuric acid was further added to the solution and stirred overnight. Dimethylformamide was distilled off and water was added to extract the residue with ethyl acetate. The extract was washed with saturated aqueous sodium chloride solution and dried over anhydrous sodium sulfate, and then ethyl acetate was distilled off to obtain the crude product. The crude product was purified by preparative thin layer chromatography using hexane / ethyl acetate (3: 1) as developing solvent to afford 0.15 g of the target compound in the form of a colorless viscous oil. It solidified when left as it was.

[실시예 A-2]Example A-2

3-(7-플루오로-3-옥소-4-프로파르길-2H-1,4-벤조옥사진-6-일)-6-트리플루오로메틸-2,4(1H,3H)-피리미딘디온(화합물 A-2)의 합성3- (7-fluoro-3-oxo-4-propargyl-2H-1,4-benzooxazin-6-yl) -6-trifluoromethyl-2,4 (1H, 3H) -pyri Synthesis of Middinedione (Compound A-2)

Figure kpo00071
Figure kpo00071

상온에서 메톡시화나트륨 0.33g과 디메틸포름아미드 5ml의 혼합물에 3-아미노-4,4,4-트리플루오로크로토네이트 1.10g을 첨가하였다. 20분간 정치시킨 후, 혼합된 용액에 6-에톡시카르보닐아미노-7-플루오로-3-옥소-4-프로파르길-2H-1,4-벤조옥사진 1.76g을 첨가하고 130℃에서 4시간 동안 가열하였다. 용액을 상온까지 냉각시킨 후, 용액을 얼음물에 부어넣고 생성된 용액을 디에틸 에테르로 2회 추출하였다. 묽은 염산으로 수성층을 산성으로 만들고 에틸 아세테이트로 3회 추출하였다. 염화나트륨 포화 수용액으로 에틸 아세테이트 추출물을 세척하고 무수 황산나트륨 상에서 건조시켰다. 에틸 아세테이트를 증류해낸 후, 전개용매로서 클로로포름을 사용하는 컬럼 크로마토그래피에 의해 잔류물을 정제하여 목적 화합물 0.20g을 담황색 결정 형태로 수득하였다.1.10 g of 3-amino-4,4,4-trifluorocrotonate was added to a mixture of 0.33 g of sodium methoxide and 5 ml of dimethylformamide at room temperature. After standing for 20 minutes, 1.76 g of 6-ethoxycarbonylamino-7-fluoro-3-oxo-4-propargyl-2H-1,4-benzoxazine was added to the mixed solution, and the mixture was stirred at 130 deg. Heated for 4 hours. After the solution was cooled to room temperature, the solution was poured into iced water and the resulting solution was extracted twice with diethyl ether. The aqueous layer was made acidic with dilute hydrochloric acid and extracted three times with ethyl acetate. The ethyl acetate extract was washed with saturated aqueous sodium chloride solution and dried over anhydrous sodium sulfate. After distilling off ethyl acetate, the residue was purified by column chromatography using chloroform as developing solvent to give 0.20 g of the target compound as pale yellow crystalline form.

[실시예 A-3]Example A-3

3-(7-플루오로-3-옥소-4-(2-피리딜메틸)-2H-1,4-벤조옥사진-6-일)-1-메틸-6-트리플루오로메틸-2,4(1H,3H)-피리미딘디온(화합물 A-3)의 합성3- (7-fluoro-3-oxo-4- (2-pyridylmethyl) -2H-1,4-benzooxazin-6-yl) -1-methyl-6-trifluoromethyl-2, Synthesis of 4 (1H, 3H) -pyrimidinedione (Compound A-3)

Figure kpo00072
Figure kpo00072

상온에서, 수소화나트륨(순소:55%) 0.05g이 현탁된 N,N-디메틸포름아미드 용액(5ml)에 3-(7-플루오로-3-옥소-2H-1,4-벤조옥사진-6-일)-1-메틸-6-트리플루오로메틸-2,4(1H,3H)-피리미딘디온 0.20g을 첨가하였다. 20분간 정치시킨 후, 이 용액에 2-클로로메틸피리딘 히드로클로라이드 0.09g을 첨가하고 4시간동안 교반하였다. N,N-디메틸포름아미드를 증류해내고 물을 첨가하여 잔류물을 에틸 아세테이트로 추출하였다. 염화나트륨 포화 수용액으로 추출물을 세척하고 무수 황산나트륨 상에서 건조시킨 후, 에틸 아세테이트를 증류해내어 조 생성물을 수득하였다. 전개용매로서 헥산/에틸 아세테이트(2:3)를 사용하는 예비 박층 크로마토그래피에 의해 이 생성물을 정제시켜 목적 화합물 0.09g을 담황색 결정 형태로 수득하였다.At room temperature, 3- (7-fluoro-3-oxo-2H-1,4-benzoxazine- in a N, N-dimethylformamide solution (5 ml) in which 0.05 g of sodium hydride (pure: 55%) was suspended. 0.20 g of 6-yl) -1-methyl-6-trifluoromethyl-2,4 (1H, 3H) -pyrimidinedione was added. After standing for 20 minutes, 0.09 g of 2-chloromethylpyridine hydrochloride was added to the solution and stirred for 4 hours. N, N-dimethylformamide was distilled off and water was added to extract the residue with ethyl acetate. The extract was washed with saturated aqueous sodium chloride solution and dried over anhydrous sodium sulfate, and then ethyl acetate was distilled off to obtain the crude product. The product was purified by preparative thin layer chromatography using hexane / ethyl acetate (2: 3) as developing solvent to afford 0.09 g of the target compound as pale yellow crystalline form.

[실시예 A-4]Example A-4

3-(7-플루오로-3-옥소-2H-1,4-벤조옥사진-6-일)-1-메틸-6-트리플루오로메틸-2,4(1H,3H)-피리미딘디온(화합물 A-4)의 합성3- (7-fluoro-3-oxo-2H-1,4-benzooxazin-6-yl) -1-methyl-6-trifluoromethyl-2,4 (1H, 3H) -pyrimidinedione Synthesis of (Compound A-4)

Figure kpo00073
Figure kpo00073

3-(7-플루오로-3-옥소-2H-1,4-벤조옥사진-6-일)-6-트리플루오로메틸-2,4(1H,3H)-피리미딘디온 0.85g을 N,N-디메틸포름아미드 8.5ml에 용해시켰다. 무수 탄산칼륨 0.17g과 메틸 아이오다이드 0.15ml를 첨가하고 혼합된 용액을 4시간 동안 교반하였다. 반응이 종결된 후, N,N-디메틸포름아미드를 증류해내고 물을 첨가하여 잔류물을 에틸 아세테이트로 추출하였다. 염화나트륨 포화수용액으로 추출물을 세척하고 무수 황산나트륨 상에서 건조시킨 후, 에틸 아세테이트를 증류해내어 조 생성물을 수득하였다. 전개용매로서 클로로포름을 사용하는 컬럼 크로마토그래피에 의해 이 생성물을 정제하여 목적 화합물 0.53g을 담황색 결정 형태로 수득하였다.0.85 g of 3- (7-fluoro-3-oxo-2H-1,4-benzooxazin-6-yl) -6-trifluoromethyl-2,4 (1H, 3H) -pyrimidinedione is N It was dissolved in 8.5 ml of N-dimethylformamide. 0.17 g of anhydrous potassium carbonate and 0.15 ml of methyl iodide were added and the mixed solution was stirred for 4 hours. After the reaction was completed, N, N-dimethylformamide was distilled off and water was added to extract the residue with ethyl acetate. The extract was washed with saturated aqueous sodium chloride solution and dried over anhydrous sodium sulfate, and then ethyl acetate was distilled off to obtain the crude product. The product was purified by column chromatography using chloroform as the developing solvent to give 0.53 g of the target compound in the form of pale yellow crystals.

[실시예 B-1]Example B-1

3-(4-클로로-2-플루오로-5-메톡시카르보닐메틸티오페닐)-1-메틸-6-트리플루오로메틸-2,4(1H,3H)-피리미딘디온(화합물 B-1)의 합성3- (4-Chloro-2-fluoro-5-methoxycarbonylmethylthiophenyl) -1-methyl-6-trifluoromethyl-2,4 (1H, 3H) -pyrimidinedione (Compound B- 1) Synthesis

Figure kpo00074
Figure kpo00074

상온에서, 디메틸포름아미드 5ml중 수소화나트륨(순도:55%) 0.16g의 현탁액에 디메틸포름아미드 10ml중 3-(4-클로로-2-플루오로-5-메톡시카르보닐메틸티오페닐)-6-트리플루오로메틸-2,4(1H,3H)-피리미딘디온 1.5g의 용액을 적가하였다. 수소가 더 이상 발생하지 않을 때 디메틸황산 0.59g을 첨가하고 생성된 용액을 상온에서 3시간동안 교반하였다. 반응 혼합물을 물 300ml에 부어넣고 에틸 아세테이트로 2회 추출하였다. 추출물을 염화나트륨 포화 수용액으로 세척하고 무수 황산나트륨 상에서 건조시킨 후 에틸 아세테이트를 증류해내어 조 생성물을 수득하였다. 수득한 생성물을 예비 박층 크로마토그래피(전개용매:CHCl3), 또 예비 고성능 액체 크로마토그래피(용리액:CHCN/H2O(5:1))로 정제하여 목적 화합물 0.1g을 점성 오일 형태로 수득하였다.At room temperature, in a suspension of 0.16 g of sodium hydride (purity: 55%) in 5 ml of dimethylformamide, 3- (4-chloro-2-fluoro-5-methoxycarbonylmethylthiophenyl) -6 in 10 ml of dimethylformamide A solution of 1.5 g of -trifluoromethyl-2,4 (1H, 3H) -pyrimidinedione was added dropwise. When hydrogen no longer generated, 0.59 g of dimethyl sulfate was added and the resulting solution was stirred at room temperature for 3 hours. The reaction mixture was poured into 300 ml of water and extracted twice with ethyl acetate. The extract was washed with saturated aqueous sodium chloride solution and dried over anhydrous sodium sulfate and then ethyl acetate was distilled off to give the crude product. The obtained product was purified by preparative thin layer chromatography (developing solvent: CHCl 3 ) and preparative high performance liquid chromatography (eluent: CHCN / H 2 O (5: 1)) to obtain 0.1 g of the target compound in the form of a viscous oil. .

[실시예 B-2]Example B-2

3-(4-클로로-2-플루오로-5-메톡시카르보닐메틸티오페닐)-6-트리플루오로메틸-2,4(1H,3H)-피리미딘디온(화합물 B-2)의 합성Synthesis of 3- (4-chloro-2-fluoro-5-methoxycarbonylmethylthiophenyl) -6-trifluoromethyl-2,4 (1H, 3H) -pyrimidinedione (Compound B-2)

Figure kpo00075
Figure kpo00075

디메틸포름아미드 110ml에 수소화나트륨(순도:55%) 1.14g을 현탁시켜 제조한 용액에 무수 톨루엔 5ml중 에틸 3-아미노-4,4,4-트리플루오로크로토네이트 4.75g의 용액을 적가하였다. 0℃에서 15분에 걸쳐 교반하면서 상기와 같이 적가하였다. 생성된 혼합물을 0℃에서 15분동안 더 교반하였다. 반응 혼합물을 -30℃까지 냉각시키고 무수 톨루엔 50ml와 4-클로로-2-플루오로-5-메톡시카르보닐메틸티오페닐 이소시아네이트 6.9g으로 된 용액을 여기에 적가하였다. 생성된 반응 혼합물을 다시 상온으로 한 후 2시간동안 교반하였다. 용매를 증류해낸 후, 잔류 용액에 에틸 아세테이트를 첨가하고 2N 염산 20ml와 물 500ml의 용액으로 2회 세척하며 염화나트륨 포화 수용액으로 세척한 후 무수 황산나트륨 상에서 건조시키고 에틸 아세테이트를 증류해내어 조 생성물을 수득하였다. 이 조 생성물을 전개용매로서 CHCl3를 사용하는 실리카겔 컬럼 크로마토그래피에 의해 예비 정제하고 전개용매로서 에틸 아세테이트/헥산(3:1]을 사용하는 실리카겔 컬럼 크로마토그래피에 의해 정제시켜 목적 화합물 1.5g을 점성 오일 형태로 수득하였다.To a solution prepared by suspending 1.14 g of sodium hydride (purity: 55%) in 110 ml of dimethylformamide, a solution of 4.75 g of ethyl 3-amino-4,4,4-trifluorocrotonate in 5 ml of anhydrous toluene was added dropwise. It was added dropwise as above with stirring at 0 ° C. over 15 minutes. The resulting mixture was further stirred at 0 ° C. for 15 minutes. The reaction mixture was cooled to −30 ° C. and a solution of 50 ml of anhydrous toluene and 6.9 g of 4-chloro-2-fluoro-5-methoxycarbonylmethylthiophenyl isocyanate was added dropwise thereto. The resulting reaction mixture was returned to room temperature and stirred for 2 hours. After distilling off the solvent, ethyl acetate was added to the remaining solution, washed twice with a solution of 20 ml of 2N hydrochloric acid and 500 ml of water, washed with a saturated aqueous sodium chloride solution, dried over anhydrous sodium sulfate, and the ethyl acetate was distilled off to obtain a crude product. . The crude product was preliminarily purified by silica gel column chromatography using CHCl 3 as the developing solvent and silica gel column chromatography using ethyl acetate / hexane (3: 1] as the developing solvent to give the desired compound 1.5g. Obtained in oil form.

[실시예 C-1]Example C-1

3-(4-클로로-2-플루오로-5-(5-메틸-1,3,4-옥사디아졸-2-일)페닐-1-메틸-6-트리플루오로메틸-2,4(1H,3H)-피리미딘디온(화합물 C-1)의 합성3- (4-chloro-2-fluoro-5- (5-methyl-1,3,4-oxadiazol-2-yl) phenyl-1-methyl-6-trifluoromethyl-2,4 ( Synthesis of 1H, 3H) -pyrimidinedione (Compound C-1)

Figure kpo00076
Figure kpo00076

25℃에서, 디메틸포름아미드 13ml중 수소화나트륨(오일, 순도:55%) 0.31g의 현탁액에 N,N-디메틸포름아미드 20ml와 3-(4-클로로-2-플루오로-5-(5-메틸-1,3,4-옥사디아졸-2-일)페닐)-6-트리플루오로메틸-2,4(1H,3H)-피리미딘디온 2.5g으로 이루어진 용액을 적가하였다. 수소가 더 이상 발생하지 않으면 15분에 걸쳐 디메틸황산 1.02g을 첨가하였다. 혼합된 용액을 상온에서 2시간동안 교반하고 물을 첨가하여 에틸 아세테이트로 추출하였다. 추출물을 무수 황산나트륨 상에서 건조시켰다. 용매를 증류해내고 용리액으로서 아세토니트릴/물(5:1)을 사용하는 예비 고성능 액체 크로마토그래피에 의해 잔류물을 정제하여 목적 화합물 0.78g을 수득하였다.At 25 ° C., in a suspension of 0.31 g of sodium hydride (oil, purity: 55%) in 13 ml of dimethylformamide, 20 ml of N, N-dimethylformamide and 3- (4-chloro-2-fluoro-5- (5- A solution consisting of 2.5 g of methyl-1,3,4-oxadiazol-2-yl) phenyl) -6-trifluoromethyl-2,4 (1H, 3H) -pyrimidinedione was added dropwise. 1.02 g of dimethylsulphuric acid was added over 15 minutes when hydrogen no longer occurred. The mixed solution was stirred at room temperature for 2 hours and extracted with ethyl acetate by adding water. The extract was dried over anhydrous sodium sulfate. The solvent was distilled off and the residue was purified by preparative high performance liquid chromatography using acetonitrile / water (5: 1) as eluent to afford 0.78 g of the desired compound.

[실시예 C-2]Example C-2

3-(4-클로로-2-플루오로-5-(5-메틸-1,3,4-옥사디아졸-2-일)페닐)-6-트리플루오로메틸-2,4(1H,3H)-피리미딘디온(화합물 C-2)의 합성3- (4-chloro-2-fluoro-5- (5-methyl-1,3,4-oxadiazol-2-yl) phenyl) -6-trifluoromethyl-2,4 (1H, 3H Synthesis of) -pyrimidinedione (Compound C-2)

Figure kpo00077
Figure kpo00077

0℃에서 15분에 걸쳐, 디메틸포름아미드 75ml중 수소화나트륨(오일, 순도:55%) 1.04g의 현탁액에 톨루엔 58ml와 에틸 3-아미노-4,4,4-트리플루오로크로토네이트 4.3g으로 된 용액을 적가하였다. 그후, 용액을 0℃에서 15분동안 교반한 다음 -30℃까지 냉각시키고 톨루엔 60ml와 4-클로로-2-플루오로-5-(5-메틸-1,3,4-옥사디아졸-2-일)페닐 이소시아네이트 5.7g으로 된 용액을 적가하였다. 그 결과 생성된 혼합 용액을 상온에서 3시간동안 교반하였다.Over 15 minutes at 0 ° C., in a suspension of 1.04 g of sodium hydride (oil, purity: 55%) in 75 ml of dimethylformamide, 58 ml of toluene and 4.3 g of ethyl 3-amino-4,4,4-trifluorocrotonate Solution was added dropwise. The solution was then stirred at 0 ° C. for 15 minutes, then cooled to −30 ° C. and 60 ml of toluene and 4-chloro-2-fluoro-5- (5-methyl-1,3,4-oxadiazole-2- A solution of 5.7 g of 1) phenyl isocyanate was added dropwise. The resulting mixed solution was stirred at room temperature for 3 hours.

감압하에 용매를 증류해내고 그 결과 수득된 오일성 물질에 물 300ml와 2N 염산 13.3ml로 된 용액을 첨가한 후 에틸 아세테이트로 2회 추출하였다. 에틸 아세테이트 층을 염화나트륨 포화 수용액으로 세척하고 무수 황산나트륨 상에서 건조시켰다. 용매를 증류해내고 생성된 조 생성물을 용리액으로서 아세토니트릴/물(5:1)을 사용하는 예비 고성능 액체 크로마토그래피에 의해 정제하여 목적 화합물 1.78g을 수득하였다.The solvent was distilled off under reduced pressure, and 300 ml of water and 13.3 ml of 2N hydrochloric acid were added to the resulting oily substance, followed by extraction twice with ethyl acetate. The ethyl acetate layer was washed with saturated aqueous sodium chloride solution and dried over anhydrous sodium sulfate. The solvent was distilled off and the resulting crude product was purified by preparative high performance liquid chromatography using acetonitrile / water (5: 1) as eluent to afford 1.78 g of the desired compound.

상기 실시예에 따라, 또 상기 실시예 또는 도식과 유사한 공정에 따라 합성된 본 발명의 우라실 유도체가 표 1a, 1b 및 1c에 기재되어 있으며, 이들 화합물의 물리적 특성이 표 2a, 2b 및 2c에 기재되어 있다. 그러나, 본 발명에 의해 수득될 수 있는 우라실 유도체는 하기 표에 기재된 것들로 한정되지는 않는다.The uracil derivatives of the present invention synthesized according to the above examples and according to processes similar to the above examples or schemes are described in Tables 1a, 1b and 1c, and the physical properties of these compounds are described in Tables 2a, 2b and 2c. It is. However, the uracil derivatives obtainable by the present invention are not limited to those listed in the table below.

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상기 실시예에 따라, 또 상기 실시예 또는 도식에 따라 합성되는 본 발명의 우라실 유도체가 표 3aa 내지 3cj에 기재되어 있다. 그러나, 본 발명에 따라 수득할 수 있는 화합물은 하기 표에 나타낸 것들로 한정되지는 않는다.According to the above examples, the uracil derivatives of the present invention synthesized according to the above examples or schemes are described in Tables 3aa to 3cj. However, the compounds obtainable according to the invention are not limited to those shown in the table below.

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하기에 나타낸 것은 본 발명의 화합물을 사용한 제형의 예이다. 그러나, 본 발명의 요지에 속하는 제형은 하기의 것들로 한정되지는 않는다. 하기 제형 실시예의 설명에서, 달리 언급하지 않는 한 부는 모두 중량 기준이다.Shown below are examples of formulations using the compounds of the invention. However, formulations belonging to the gist of the present invention are not limited to the following. In the description of the formulation examples below, all parts are by weight unless otherwise indicated.

[제형 실시예 1]Formulation Example 1

습윤성 분말Wettable powder

Figure kpo00179
Figure kpo00179

상기 성분을 균일하게 혼합 및 분쇄하여 습윤성 분말을 제형한다.The ingredients are uniformly mixed and ground to formulate wettable powders.

[제형 실시예 2]Formulation Example 2

유화 농축액Emulsion concentrate

Figure kpo00180
Figure kpo00180

Figure kpo00181
Figure kpo00181

상기 성분을 균일하게 혼합하여 유화 농축액을 제조한다.The components are uniformly mixed to prepare an emulsion concentrate.

[제형 실시예 3]Formulation Example 3

유동제Fluid

Figure kpo00182
Figure kpo00182

상기 성분을 균일하게 혼합하여 유동제를 제형한다.The ingredients are uniformly mixed to formulate a flow agent.

[제형 실시예 4]Formulation Example 4

과립상 습윤성 분말(무수 유동제)Granular Wetting Powder (Anhydrous Fluid)

Figure kpo00183
Figure kpo00183

Figure kpo00184
Figure kpo00184

상기 성분을 균일하게 혼합 및 분말화하여 무수 유동제를 제조한다.The components are uniformly mixed and powdered to produce anhydrous fluidizing agents.

[제형 실시예 5]Formulation Example 5

습윤성 분말Wettable powder

Figure kpo00185
Figure kpo00185

상기 성분을 균일하게 혼합 및 분쇄하여 습윤성 분말을 제조한다.The ingredients are uniformly mixed and ground to produce a wettable powder.

[제형 실시예 6]Formulation Example 6

유화 농축액Emulsion concentrate

Figure kpo00186
Figure kpo00186

Figure kpo00187
Figure kpo00187

상기 성분을 균일하게 혼합하여 유화 농축액을 제조한다.The components are uniformly mixed to prepare an emulsion concentrate.

[제형 실시예 7]Formulation Example 7

유동제Fluid

Figure kpo00188
Figure kpo00188

상기 성분을 균일하게 혼합하여 유동제를 제조한다.The components are mixed uniformly to prepare a flow agent.

[제형 실시예 8]Formulation Example 8

과립제Granules

Figure kpo00189
Figure kpo00189

Figure kpo00190
Figure kpo00190

상기 성분을 균일하게 혼합 및 분쇄한 후 소량의 물을 첨가하여 교반하면서 반죽하고 압출 과립기로 과립화한 다음 건조시켜 과립제를 제조한다.The ingredients are uniformly mixed and pulverized, then a small amount of water is added to knead with stirring, granulated with an extruder granulator and dried to prepare a granule.

[제형 실시예 9][Formulation Example 9]

과립상 습윤성 분말(무수 유동제)Granular Wetting Powder (Anhydrous Fluid)

Figure kpo00191
Figure kpo00191

상기 성분을 균일하게 혼합 및 분말화하여 무수 유동제를 수득한다.The components are uniformly mixed and powdered to obtain anhydrous flow agent.

[제형 실시예 10]Formulation Example 10

습윤성 분말Wettable powder

Figure kpo00192
Figure kpo00192

Figure kpo00193
Figure kpo00193

상기 성분을 균일하게 혼합 및 분쇄하여 습윤성 분말을 제조한다.The ingredients are uniformly mixed and ground to produce a wettable powder.

[제형 실시예 11]Formulation Example 11

유화 농축액Emulsion concentrate

Figure kpo00194
Figure kpo00194

상기 성분을 균일하게 혼합하여 유화 농축액을 제조한다.The components are uniformly mixed to prepare an emulsion concentrate.

[제형 실시예 12]Formulation Example 12

유동제Fluid

Figure kpo00195
Figure kpo00195

Figure kpo00196
Figure kpo00196

상기 성분을 균일하게 혼합하여 유동제를 제조한다.The components are mixed uniformly to prepare a flow agent.

[제형 실시예 13]Formulation Example 13

과립제Granules

Figure kpo00197
Figure kpo00197

상기 성분을 균일하게 혼합 및 분쇄하고 소량의 물을 첨가하여 교반하면서 반죽한 후, 압출 과립기로 과립화하고 건조시켜 과립제를 제조한다.The ingredients are uniformly mixed and pulverized, kneaded with the addition of a small amount of water and stirred, followed by granulation with an extruder granulator and drying to prepare a granule.

[제형 실시예 14]Formulation Example 14

과립상 습윤성 분말(무수 유동제)Granular Wetting Powder (Anhydrous Fluid)

Figure kpo00198
Figure kpo00198

상기 성분을 균일하게 혼합 및 분말화하여 무수 유동제를 제조한다.The components are uniformly mixed and powdered to produce anhydrous fluidizing agents.

상기 제제를 실제로 사용함에 있어서, 습윤성 분말, 유화 농축액, 유동제 및 과립상 습윤성 분말의 경우, 이들을 물로 50 내지 1,000배 희석시키고 활성성분이 헥타아르당 0.0001 내지 10kg의 비율로 공급되도록 투여한다.In practical use of the formulations, for wettable powders, emulsion concentrates, flow agents and granular wettable powders, they are diluted 50 to 1,000 times with water and administered so that the active ingredient is supplied at a rate of 0.0001 to 10 kg per hectare.

본 발명에 따른 화합물의 제초제용 활성성분으로서의 유용성은 하기 시험 실시예의 결과로부터 명백하게 평가된다.The utility of the compounds according to the invention as herbicidal active ingredients is clearly assessed from the results of the following test examples.

[시험 실시예 1][Test Example 1]

토양처리에 의한 제초효과의 시험Test of herbicidal effect by soil treatment

살균한 홍적 토양을 15cm×22cm×6cm 플라스틱 용기에 넣었다. 이어 반야드그래스[barnyardgrass(Echinochloa crus-galli)], 바랭이류[crabgrass(Digitaria adscendens)], 1년생 사초속 잡초(sedge(Cyperus microiria)], 까마종이(black nightshade(Solanum nigrum)], 헤어리 갈린소가(hairly galinsoga(Galinsoga ciliate)], 피일드크레스(fieldcress(Rorippa indica)], 벼(Oryza sativa), 옥수수(Zea mays), alf(Triticum aestivum), 대두(Glycine max) 및 목화(Cossipium herbaceuThe sterilized redness soil was placed in a 15 cm x 22 cm x 6 cm plastic container. Followed by barnyardgrass (Echinochloa crus-galli), crabgrass (Digitaria adscendens), annual herb (syperus microiria), black nightshade (Solanum nigrum), hairy Hairly galinsoga (Galinsoga ciliate), fieldcress (Rorippa indica), rice (Oryza sativa), corn (Zea mays), alf (Triticum aestivum), soy (Glycine max) and cotton (Cossipium) herbaceu

m)의 종자를 혼합하여 용기에 파종하고, 토양으로 약 1cm 덮은 후 활성성분이 예정된 비율로 공급되도록 소규모의 분무기를 사용하여 액체 시험 제초제를 토양 표면에 균일하게 분무하였다. 상기 적절한 제형 실시예에 따라 제조된 제제를 물로 희석함으로써 각각의 액체 시험 제초제를 제조하였다. 액체 시험 제초제를 투여(분무)한 지 3주 후, 상기 잡초 및 농작물의 각 종에 대한 그 제초효과를 검사하고 하기 표준 등급에 따라 평가하였다. 그 결과는 표 4-A-1, 4-A-2, 4-B, 4-C-1 및 4-C-2에 기재되어 있다.m) seeds were mixed and seeded in a container, covered about 1 cm with soil, and then evenly sprayed with a liquid test herbicide on the soil surface using a small atomizer so that the active ingredient was supplied at a predetermined rate. Each liquid test herbicide was prepared by diluting the formulation prepared according to the appropriate formulation example above with water. Three weeks after the administration (spray) of the liquid test herbicide, the herbicidal effects on each species of the weeds and crops were examined and evaluated according to the following standard grades. The results are shown in Tables 4-A-1, 4-A-2, 4-B, 4-C-1 and 4-C-2.

[표준 등급][Standard grade]

5:생장 조절률이 90% 이상이다.(식물이 거의 완전히 시들었다.)5: Growth rate is over 90% (plant is almost completely withered)

4:생장 조절률이 70 내지 90%이다.4: growth control rate is 70-90%.

3:생장 조절률이 40 내지 70%이다.3: The growth control rate is 40 to 70%.

2:생장 조절률이 20 내지 40%이다.2: growth control rate is 20 to 40%.

1:생장 조절률이 5% 미만이다.(거의 효과가 없다.)1: Growth control rate is less than 5% (almost no effect)

처리지역 및 미처리지역에서 식물의 지상 부위의 중량을 측정한 후 하기 식으로부터 생장 조절률을 결정하였다:Growth control rates were determined from the following equations after weighing the ground areas of the plants in the treated and untreated areas:

Figure kpo00199
Figure kpo00199

[시험 실시예 2][Test Example 2]

엽면 처리에 의한 제초효과 시험Herbicide effect test by foliar treatment

살균한 홍적 토양이 채워진 15cm×22cm×6cm 플라스틱 용기에 반야드그래스[barnyardgrass(Echinochloa crus-galli)], 바랭이류[crabgrass(Digitaria adscendens)], 1년생 사초속 잡초(sedge(Cyperus microiria)], 까마종이[black nightshade(Solanum nigrum)], 헤어리 갈린소가(hairly galinsoga(Galinsoga ciliate)], 피일드크레스(Fieldcress(Rorippa indica)], 벼(Oryza sativa), 옥수수(Zea mays), 밀(Triticum aestivum), 대두(Glycine max), 목화(Cossipium herbaceum) 및 사탕수수(Beta vulgaris)의 종자를 흩부려 파종하고 토양으로 약 1cm 가량 덮었다. 식물이 2 내지 3-엽 단계까지 자라면 활성성분이 예정된 비율로 공급되도록 액체 시험 제초제를 식물의 잎에 균일하게 분무하였다.Barnyardgrass (Echinochloa crus-galli), crabgrass (Digitaria adscendens), annual soybean weed (Cyperus microiria), in a plastic container filled with sterile redness soil. Black nightshade (Solanum nigrum), hairy galinsoga (Galinsoga ciliate), fieldcress (Rorippa indica), rice (Oryza sativa), corn (Zea mays), wheat ( Seeds of Triticum aestivum, Glycine max, Cotton (Cossipium herbaceum) and Sugarcane (Beta vulgaris) were sown and covered with soil about 1 cm in length. Liquid test herbicides were evenly sprayed on the leaves of the plants to be fed at a predetermined rate.

상기 적절한 제형 실시예에 따라 제조된 제제를 물로 희석시킴으로써 각각의 액체 시험 제초제를 제조하였으며 소규모 분무기로 잡초의 잎 전체에 분무하였다. 액체 시험 제초제를 분무한 지 4주 후, 잡초 및 유용 식물의 상기 종에 대한 제초효과를 검사하고 시험 실시예 1에서 이용한 것과 동일한 표준 등급에 따라 평가하였다. 결과는 표 5aa, 5ab, 5b, 5ca 및 5cb에 기재되어 있다.Each liquid test herbicide was prepared by diluting the formulation prepared according to the appropriate formulation example above and sprayed over the leaves of the weeds with a small atomizer. Four weeks after spraying the liquid test herbicide, the herbicidal effects on the species of weeds and useful plants were examined and evaluated according to the same standard grade as used in Test Example 1. The results are described in Tables 5aa, 5ab, 5b, 5ca and 5cb.

[시험 실시예 3][Test Example 3]

물을 댄 논에서의 제초효과 시험Herbicide test in watered paddy fields

1/5000아르의 바그너(Wagner) 화분에 충적 토양을 넣은 후, 물을 부어넣어 토양을 반죽하고 물이 토양 위 2cm까지 찬 논의 소규모 모형을 만들었다. 이어 반야드그래스[barnyardgrass(Echinochloa crus-galli)], 덕샐러드(ducksalad(Monochoria vaginalis)], 투스컵[toothcup(Rotala indica)] 및 불러쉬[Bullrush(Scirpus juncoides)]의 종자를 혼합하여 상기 화분에 파종하였다. 또한 다년생 사초속 잡초[sedge(Cyperus serotinus)] 및 쇠귀나물[arrowhead(Sagittaria pygmaea)]의 줄기를 토양층에 심고 잎이 2.5장 있는 모를 이식하였다. 화분을 25 내지 30℃의 온실에 두어 식물이 정상적으로 생장하도록 하였다. 파종한 지 2일째 되는 날에, 예정된 양의 화합물이 공급되도록 눈금 피렛을 사용하여 각 화분의 물 표면에 희석된 시험 제초제액을 떨어뜨렸다. 액체 제초제를 투여한 지 3주 후, 벼 및 상기 잡초 종에 대한 제초효과를 검사하고 시험 실시예 1에서 사용하는 것과 동일한 표준 등급에 따라 평가하였다. 결과는 표 6에 기재되어 있다.After alluvial soil was placed in a 1/5000 Wagner pot, water was poured to knead the soil and a small model of rice paddy filled with water up to 2 cm above the soil. The pot was then mixed with seeds from barnyardgrass (Echinochloa crus-galli), duck salad (ducksalad (Monochoria vaginalis)), toothcup (Rotala indica) and Boulrush (Bullrush (Scirpus juncoides)). In addition, stems of perennial weeds (Syperus serotinus) and arrowhead (arrowhead (Sagittaria pygmaea)] were planted in the soil layer and seeded with 2.5 leaves. Pots were transplanted in a greenhouse at 25 to 30 ° C. On the second day after planting, the scale herbicide was used to drop the diluted test herbicide solution on the water surface of each pot to provide the desired amount of compound. Three weeks later, herbicidal effects on rice and the weed species were examined and evaluated according to the same standard grade as used in Test Example 1. The results are shown in Table 6.

표에서 밑줄이 그어진 부호는 하기와 같은 의미이다:The underlined symbols in the table have the following meanings:

N:반야드그래스[barnyardgrass(Echinochloa crus-galli)]N: Barnyardgrass [barnyardgrass (Echinochloa crus-galli)]

M:바랭이류[crabgrass(Digitaria adscendens)]M: Crabgrass (Digitaria adscendens)

K:1년생 사초속 잡초(Cyperus microiria)K: 1 year old Weed (Cyperus microiria)

H:까마종이(Solanum nigrum)H: Solanum nigrum

D:헤어리 갈린소가[hairly galinsoga(Galinsoga ciliate)]D: Hairy galinsoga (Galinsoga ciliate)

I:피일드크레스[fieldcress(Rorippa indica)]I: Field Cress (Rorippa indica)

R:벼(Oryza sativa)R: Rice (Oryza sativa)

T:옥수수(Zea mays)T: Zea mays

W:alf(Triticum aestivum)W: alf (Triticum aestivum)

S:대두(Glycine max)S: Glycine max

C:목화(Cossipium herbaceum)C: cotton (Cossipium herbaceum)

B:사탕수수(Beta vulgaris)B: sugar cane (Beta vulgaris)

하기 구조를 갖는 브로마실을 대조용 화합물로서 사용하였다:Bromacil having the following structure was used as a control compound:

Figure kpo00200
Figure kpo00200

Figure kpo00201
Figure kpo00201

Figure kpo00202
Figure kpo00202

Figure kpo00204
Figure kpo00204

Figure kpo00205
Figure kpo00205

Figure kpo00206
Figure kpo00206

Figure kpo00207
Figure kpo00207

Figure kpo00208
Figure kpo00208

Figure kpo00209
Figure kpo00209

Figure kpo00210
Figure kpo00210

Figure kpo00211
Figure kpo00211

Figure kpo00212
Figure kpo00212

Figure kpo00213
Figure kpo00213

Figure kpo00214
Figure kpo00214

Figure kpo00215
Figure kpo00215

Claims (3)

하기 일반식(IV)로 나타내어지는 우라실 유도체:Uracil derivatives represented by the following general formula (IV):
Figure kpo00216
Figure kpo00216
상기 식에서, R1은 수소 또는 C1-3알킬이고, R2는 C1-6할로알킬이고, R3은 수소이며, R4는 수소 또는 할로겐이고, R5는 할로겐, 니트로 또는 시아노이고, D1Wherein R 1 is hydrogen or C 1-3 alkyl, R 2 is C 1-6 haloalkyl, R 3 is hydrogen, R 4 is hydrogen or halogen, R 5 is halogen, nitro or cyano , D 1
Figure kpo00217
Figure kpo00217
D21은 수소, C1-3알킬, C1-3알콕실 또는 C1-3알콕시-C1-2알킬이고, D22는 수소, C1-4알킬, C3-6시클로알킬, C2-3할로알킬, 페닐 또는 벤질이고, D23은 수소 또는 C1-3알킬이고, D24는 수소, C1-3알킬 또는 C1-3알콕시-C1-2알킬이며, Z는 산소, 황 또는 NH이고, D25는 수소, 나트륨, C1-4알킬, C2-5알켄일, C3-5알킨일, C2-5아실, C1-4알킬술폰일 또는 C1-3알콕시-C1-2알킬이며, D26은 C1-4알킬 또는 C1-3할로알킬이고, D27은 수소, C1-6알킬, C3-6시클로알킬, C1-3할로알킬, C1-4알콕실, C1-4알킬티오, C1-4알콕시-카르보닐, 메르캅토, 히드록실, C1-3알콕시-C1-2알킬, C1-4알킬아미노, ND28(D29), 디메틸카르바모일, CONHSO2CH3, C1-4알킬술폰일, 또는 N(D30)SO2D31이며, D28및 D29는 독립적으로 C1-4알킬이고, D30은 수소, 나트륨, C1-4알킬, C1-4알킬술폰일 또는 C1-3알콕시-C1-2알킬이며, D31은 C1-4알킬 또는 C1-3할로알킬이고, D32는 C1-6알킬 또는 C3-6시클로알킬이고, D33, D34및 D35는 독립적으로 수소 또는 C1-6알킬이고, D36및 D37은 독립적으로 수소, C1-6알킬 또는 디메틸아미노이며, D38은 수소, 할로겐, 메르캅토, 히드록실, C1-6알킬, C3-6시클로알킬, C1-3할로알킬, C1-4알콕실, C1-4알킬티오, C1-4알콕시-카르보닐, 디메틸카르바모일, C1-3알콕시-C1-2알킬, C1-4알킬아미노, ND28(D29), CONHSO2CH3, C1-4알킬술폰일, 페닐, 벤질 또는 N(D39)SO2D31이며, D39는 수소, C1-4알킬, 나트륨, 칼륨, C1-4알킬술포닐 또는 C1-3알콕시-C1-2알킬이고, D40은 수소, C1-6알킬, C3-6시클로알킬, 페닐, 벤질 또는 2-피리딜이고, D41은 수소, 할로겐, 메르캅토, 히드록실, 아미노, C1-6알킬, C1-4알킬아미노, ND28(D29), C1-4알킬티오, CO2D28, C1-4알킬술폰일, C1-4알콕실 또는 N(D39)SO2D31이며, D42는 수소, 할로겐, 니트로, 아미노, 시아노, C1-4알킬아미노, N(D28)D29, C1-4알킬카르보닐 또는 C1-4알콕시-카르보닐이고, D43은 수소, 히드록실, 메톡시, 아미노, 벤조일 또는 C1-4알킬이며, D44는 수소, 시아노, 아세틸, C1-4알킬, 카르복실 또는 C1-4알콕시-카르보닐이며, D45및 D46은 각각 독립적으로 수소, 페닐, 히드록실, 메톡시 또는 C1-4알킬이며, D47및 D48은 각각 독립적으로 수소 또는 C1-4알킬이고, X는 산소 또는 황이다.D 21 is hydrogen, C 1-3 alkyl, C 1-3 alkoxyl or C 1-3 alkoxy-C 1-2 alkyl, D 22 is hydrogen, C 1-4 alkyl, C 3-6 cycloalkyl, C 2-3 haloalkyl, phenyl or benzyl, D 23 is hydrogen or C 1-3 alkyl, D 24 is hydrogen, C 1-3 alkyl or C 1-3 alkoxy-C 1-2 alkyl, Z is oxygen , Sulfur or NH, D 25 is hydrogen, sodium, C 1-4 alkyl, C 2-5 alkenyl, C 3-5 alkynyl, C 2-5 acyl, C 1-4 alkylsulfonyl or C 1- 3 alkoxy-C 1-2 alkyl, D 26 is C 1-4 alkyl or C 1-3 haloalkyl, D 27 is hydrogen, C 1-6 alkyl, C 3-6 cycloalkyl, C 1-3 halo Alkyl, C 1-4 alkoxyl, C 1-4 alkylthio, C 1-4 alkoxy-carbonyl, mercapto, hydroxyl, C 1-3 alkoxy-C 1-2 alkyl, C 1-4 alkylamino, ND 28 (D 29 ), dimethylcarbamoyl, CONHSO 2 CH 3 , C 1-4 alkylsulfonyl, or N (D 30 ) SO 2 D 31 , and D 28 and D 29 are independently C 1-4 alkyl and, D 30 is hydrogen, sodium, C 1-4 alkyl, C 1-4 alkylsulfonyl And one or a C 1-3 alkoxy -C 1-2 alkyl, D 31 is a C 1-4 alkyl or C 1-3 haloalkyl, D 32 is a C 1-6 alkyl or C 3-6 cycloalkyl, D 33 , D 34 and D 35 are independently hydrogen or C 1-6 alkyl, D 36 and D 37 are independently hydrogen, C 1-6 alkyl or dimethylamino, D 38 is hydrogen, halogen, mercapto, hydroxide Hydroxyl, C 1-6 alkyl, C 3-6 cycloalkyl, C 1-3 haloalkyl, C 1-4 alkoxyl, C 1-4 alkylthio, C 1-4 alkoxy-carbonyl, dimethylcarbamoyl, C 1-3 alkoxy-C 1-2 alkyl, C 1-4 alkylamino, ND 28 (D 29 ), CONHSO 2 CH 3 , C 1-4 alkylsulfonyl, phenyl, benzyl or N (D 39 ) SO 2 D 31 , D 39 is hydrogen, C 1-4 alkyl, sodium, potassium, C 1-4 alkylsulfonyl or C 1-3 alkoxy-C 1-2 alkyl, D 40 is hydrogen, C 1-6 alkyl , C 3-6 cycloalkyl, phenyl, benzyl or 2-pyridyl, D 41 is hydrogen, halogen, mercapto, hydroxyl, amino, C 1-6 alkyl, C 1-4 alkylamino, N D 28 (D 29 ), C 1-4 alkylthio, CO 2 D 28 , C 1-4 alkylsulfonyl, C 1-4 alkoxyl or N (D 39 ) SO 2 D 31 , D 42 is hydrogen, Halogen, nitro, amino, cyano, C 1-4 alkylamino, N (D 28 ) D 29 , C 1-4 alkylcarbonyl or C 1-4 alkoxy-carbonyl, D 43 is hydrogen, hydroxyl, Methoxy, amino, benzoyl or C 1-4 alkyl, D 44 is hydrogen, cyano, acetyl, C 1-4 alkyl, carboxyl or C 1-4 alkoxy-carbonyl, D 45 and D 46 are each Independently hydrogen, phenyl, hydroxyl, methoxy or C 1-4 alkyl, D 47 and D 48 are each independently hydrogen or C 1-4 alkyl, and X is oxygen or sulfur.
제1항의 우라실 유도체 제초 유효량 및 허용가능한 체 또는 희석제를 포함하는 제초성 조성물.A herbicidal composition comprising the herbicidal effective amount of the uracil derivative of claim 1 and an acceptable sieve or diluent. 제2항의 우라실 유도체 제초 유효량을 투여하는 것을 포함하는, 잡초를 죽이거나 또는 잡초의 생장을 억제하는 방법.A method of killing or inhibiting weed growth, comprising administering an effective amount of the uracil derivative herbicide of claim 2.
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