KR20000076184A - 아미노술포닐우레아 제초제 - Google Patents
아미노술포닐우레아 제초제 Download PDFInfo
- Publication number
- KR20000076184A KR20000076184A KR1019997008278A KR19997008278A KR20000076184A KR 20000076184 A KR20000076184 A KR 20000076184A KR 1019997008278 A KR1019997008278 A KR 1019997008278A KR 19997008278 A KR19997008278 A KR 19997008278A KR 20000076184 A KR20000076184 A KR 20000076184A
- Authority
- KR
- South Korea
- Prior art keywords
- straight
- groups
- formula
- branched
- dimethoxypyrimidin
- Prior art date
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- 230000002363 herbicidal effect Effects 0.000 title claims abstract description 20
- 241000196324 Embryophyta Species 0.000 claims abstract description 20
- OJXASOYYODXRPT-UHFFFAOYSA-N sulfamoylurea Chemical compound NC(=O)NS(N)(=O)=O OJXASOYYODXRPT-UHFFFAOYSA-N 0.000 claims abstract description 10
- -1 4,6-dimethoxypyrimidin-2-yl Chemical group 0.000 claims description 50
- 239000000203 mixture Substances 0.000 claims description 16
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 claims description 14
- 125000000217 alkyl group Chemical group 0.000 claims description 12
- 238000000034 method Methods 0.000 claims description 12
- 239000004009 herbicide Substances 0.000 claims description 11
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 10
- 239000000460 chlorine Substances 0.000 claims description 10
- 229910052801 chlorine Inorganic materials 0.000 claims description 10
- 125000001188 haloalkyl group Chemical group 0.000 claims description 9
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 9
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 8
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 8
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 8
- 229910052794 bromium Inorganic materials 0.000 claims description 8
- 229910052731 fluorine Inorganic materials 0.000 claims description 8
- 239000011737 fluorine Substances 0.000 claims description 8
- 125000005843 halogen group Chemical group 0.000 claims description 8
- 150000003839 salts Chemical class 0.000 claims description 7
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 claims description 6
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 6
- 125000003342 alkenyl group Chemical group 0.000 claims description 6
- 239000002585 base Substances 0.000 claims description 6
- 150000003944 halohydrins Chemical class 0.000 claims description 6
- 239000011630 iodine Substances 0.000 claims description 6
- 229910052740 iodine Inorganic materials 0.000 claims description 6
- 239000003960 organic solvent Substances 0.000 claims description 6
- 239000007787 solid Substances 0.000 claims description 6
- 239000004480 active ingredient Substances 0.000 claims description 5
- 239000004202 carbamide Substances 0.000 claims description 5
- 125000004397 aminosulfonyl group Chemical group NS(=O)(=O)* 0.000 claims description 4
- 150000007530 organic bases Chemical class 0.000 claims description 4
- 239000004094 surface-active agent Substances 0.000 claims description 4
- 239000013543 active substance Substances 0.000 claims description 3
- 150000003973 alkyl amines Chemical class 0.000 claims description 3
- 125000000304 alkynyl group Chemical group 0.000 claims description 3
- 150000004945 aromatic hydrocarbons Chemical class 0.000 claims description 3
- 125000001316 cycloalkyl alkyl group Chemical group 0.000 claims description 3
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 3
- 125000005265 dialkylamine group Chemical group 0.000 claims description 3
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- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 3
- 238000002360 preparation method Methods 0.000 claims description 3
- 239000002904 solvent Substances 0.000 claims description 3
- QAKDVXYDGVNTSD-UHFFFAOYSA-N 2-[(4,6-dimethoxypyrimidin-2-yl)carbamoylsulfamoylamino]-n-ethylbenzamide Chemical compound CCNC(=O)C1=CC=CC=C1NS(=O)(=O)NC(=O)NC1=NC(OC)=CC(OC)=N1 QAKDVXYDGVNTSD-UHFFFAOYSA-N 0.000 claims description 2
- KPXBDJXUIHVSGT-UHFFFAOYSA-N 2-[(4,6-dimethoxypyrimidin-2-yl)carbamoylsulfamoylamino]-n-methoxy-n-methylbenzamide Chemical compound CON(C)C(=O)C1=CC=CC=C1NS(=O)(=O)NC(=O)NC1=NC(OC)=CC(OC)=N1 KPXBDJXUIHVSGT-UHFFFAOYSA-N 0.000 claims description 2
- JEADOQBHOQICLR-UHFFFAOYSA-N 2-[(4,6-dimethoxypyrimidin-2-yl)carbamoylsulfamoylamino]-n-methoxybenzamide Chemical compound CONC(=O)C1=CC=CC=C1NS(=O)(=O)NC(=O)NC1=NC(OC)=CC(OC)=N1 JEADOQBHOQICLR-UHFFFAOYSA-N 0.000 claims description 2
- AGBBOZCOFQXSDU-UHFFFAOYSA-N 2-[(4,6-dimethoxypyrimidin-2-yl)carbamoylsulfamoylamino]-n-methylbenzamide Chemical compound CNC(=O)C1=CC=CC=C1NS(=O)(=O)NC(=O)NC1=NC(OC)=CC(OC)=N1 AGBBOZCOFQXSDU-UHFFFAOYSA-N 0.000 claims description 2
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 claims description 2
- 238000009835 boiling Methods 0.000 claims description 2
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- 239000012442 inert solvent Substances 0.000 claims description 2
- 229910052783 alkali metal Inorganic materials 0.000 claims 1
- 150000001340 alkali metals Chemical class 0.000 claims 1
- 229910052784 alkaline earth metal Inorganic materials 0.000 claims 1
- 150000001342 alkaline earth metals Chemical class 0.000 claims 1
- 150000003863 ammonium salts Chemical class 0.000 claims 1
- 150000001875 compounds Chemical class 0.000 description 43
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 18
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- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 3
- 231100000331 toxic Toxicity 0.000 description 3
- 230000002588 toxic effect Effects 0.000 description 3
- 238000009333 weeding Methods 0.000 description 3
- OVXMBIVWNJDDSM-UHFFFAOYSA-N (benzhydrylideneamino) 2,6-bis[(4,6-dimethoxypyrimidin-2-yl)oxy]benzoate Chemical compound COC1=CC(OC)=NC(OC=2C(=C(OC=3N=C(OC)C=C(OC)N=3)C=CC=2)C(=O)ON=C(C=2C=CC=CC=2)C=2C=CC=CC=2)=N1 OVXMBIVWNJDDSM-UHFFFAOYSA-N 0.000 description 2
- KBPLFHHGFOOTCA-UHFFFAOYSA-N 1-Octanol Chemical compound CCCCCCCCO KBPLFHHGFOOTCA-UHFFFAOYSA-N 0.000 description 2
- MZHCENGPTKEIGP-UHFFFAOYSA-N 2-(2,4-dichlorophenoxy)propanoic acid Chemical compound OC(=O)C(C)OC1=CC=C(Cl)C=C1Cl MZHCENGPTKEIGP-UHFFFAOYSA-N 0.000 description 2
- KFEFNHNXZQYTEW-UHFFFAOYSA-N 2-(4-isopropyl-4-methyl-5-oxo-4,5-dihydro-1H-imidazol-2-yl)-4-methylbenzoic acid Chemical compound N1C(=O)C(C(C)C)(C)N=C1C1=CC(C)=CC=C1C(O)=O KFEFNHNXZQYTEW-UHFFFAOYSA-N 0.000 description 2
- NUPJIGQFXCQJBK-UHFFFAOYSA-N 2-(4-isopropyl-4-methyl-5-oxo-4,5-dihydro-1H-imidazol-2-yl)-5-(methoxymethyl)nicotinic acid Chemical compound OC(=O)C1=CC(COC)=CN=C1C1=NC(C)(C(C)C)C(=O)N1 NUPJIGQFXCQJBK-UHFFFAOYSA-N 0.000 description 2
- PXBFMLJZNCDSMP-UHFFFAOYSA-N 2-Aminobenzamide Chemical compound NC(=O)C1=CC=CC=C1N PXBFMLJZNCDSMP-UHFFFAOYSA-N 0.000 description 2
- ADZSGNDOZREKJK-UHFFFAOYSA-N 4-amino-6-tert-butyl-3-ethylsulfanyl-1,2,4-triazin-5-one Chemical compound CCSC1=NN=C(C(C)(C)C)C(=O)N1N ADZSGNDOZREKJK-UHFFFAOYSA-N 0.000 description 2
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- QNXAVFXEJCPCJO-UHFFFAOYSA-N Diclosulam Chemical compound N=1N2C(OCC)=NC(F)=CC2=NC=1S(=O)(=O)NC1=C(Cl)C=CC=C1Cl QNXAVFXEJCPCJO-UHFFFAOYSA-N 0.000 description 2
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- LLQPHQFNMLZJMP-UHFFFAOYSA-N Fentrazamide Chemical compound N1=NN(C=2C(=CC=CC=2)Cl)C(=O)N1C(=O)N(CC)C1CCCCC1 LLQPHQFNMLZJMP-UHFFFAOYSA-N 0.000 description 2
- RXCPQSJAVKGONC-UHFFFAOYSA-N Flumetsulam Chemical compound N1=C2N=C(C)C=CN2N=C1S(=O)(=O)NC1=C(F)C=CC=C1F RXCPQSJAVKGONC-UHFFFAOYSA-N 0.000 description 2
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D521/00—Heterocyclic compounds containing unspecified hetero rings
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N47/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid
- A01N47/08—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid the carbon atom having one or more single bonds to nitrogen atoms
- A01N47/28—Ureas or thioureas containing the groups >N—CO—N< or >N—CS—N<
- A01N47/36—Ureas or thioureas containing the groups >N—CO—N< or >N—CS—N< containing the group >N—CO—N< directly attached to at least one heterocyclic ring; Thio analogues thereof
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- Life Sciences & Earth Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Pest Control & Pesticides (AREA)
- Plant Pathology (AREA)
- Agronomy & Crop Science (AREA)
- Engineering & Computer Science (AREA)
- Dentistry (AREA)
- General Health & Medical Sciences (AREA)
- Wood Science & Technology (AREA)
- Zoology (AREA)
- Environmental Sciences (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
화학식 1 의 아미노술포닐우레아는 수많은 잡초에 대해 높은 제초능력을 가진다.
Description
제초능력이 있는 아미노술포닐우레아는 미국특허 4,515,620, 4,559,081, 4,592,776, 4,622,065 및 4,666,508 에 발표된다. 그러나 이들 제품은 일반적으로 농작물에 대해 독성이 있으며 매우 나쁜 선택성을 가짐이 드러났다.
본 발명은 아미노술포닐우레아에 관계한다. 특히, 본 발명은 높은 제초능력을 갖는 아미노술포닐우레아, 그 제조방법 및 농업에서 잡초 조절용 제초제로서의 용도에 관계한다.
본 출원인은 수많은 잡초에 대해 더 높은 제초능력을 가지며 동시에 작물에 대해 낮은 독성을 보이는 새로운 아미노술포닐우레아를 발견하였다. 그러므로 이들은 더 높은 선택성을 가진다.
따라서 본 발명의 목적은 다음 화학식 1 을 가지는 아미노술포닐우레아이다:
여기서, - R 은 염소, 불소, 브롬 또는 요오드와 같은 할로겐 원자; 직쇄형 또는 측쇄형 알킬 또는 할로알킬 C1-C4기; 직쇄형 또는 측쇄형 알콜 또는 할로알콜 C1-C4기이며
- N 은 0 또는 1 이고
- R1및 R2는 동일 또는 상이하며 수소원자; 직쇄 또는 측쇄형 알킬 또는 할로알킬 C1-C4기; 직쇄 또는 측쇄형 알콜 또는 할로알콜 C1-C4기; 또는 결합하여 알켄일 또는 옥시알켄일 C2-C5체인이며
- R3및 R4는 동일 또는 상이하며 수소원자; 직쇄 또는 측쇄형 알킬 또는 할로알킬 C3-C6기; 직쇄 또는 측쇄형 알켄일 또는 할로알켄일 C3-C6기; 직쇄 또는 측쇄형 알킨일 또는 할로알킨일 C3-C6기이며
- R5및 R6는 동일 또는 상이하며 수소원자; 염소, 불소, 브롬 또는 요오드와 같은 할로겐 원자; 직쇄 또는 측쇄형 알킬 또는 할로알킬 C1-C6기; 직쇄 또는 측쇄형 알킬아민 C1-C6기; 직쇄 또는 측쇄형 디알킬 아민 C2-C8기; 시클로알킬 또는 시클로알콕실 C3-C6기; 시클로알킬알킬 또는 시클로알킬알콕실 C4-C7기이며
- Z 는 CH 또는 N 이다.
화학식 1 의 아미노술포닐우레아는 높은 제초능을 가진다. 제초능을 갖는 화학식 1 의 아미노술포닐우레아의 예로는 다음과 같은 것이 있다:
- 2-[(4,6-디메톡시피리미딘-2-일)카바모일술파모일아미노]-N,N-디메틸-벤자미드;
- 1-[(4,6-디메톡시피리미딘-2-일)-3-{[2-(1-피롤리도노카르보닐)페닐]술파모일}우레아;
- 2-[(4,6-디메톡시피리미딘-2-일)카바모일술파모일아미노]-N-에틸-N-메틸벤자미드;
- 2-[(4,6-디메톡시피리미딘-2-일)카바모일술파모일아미노]-N-메틸벤자미드;
- 2-[(4,6-디메톡시피리미딘-2-일)카바모일술파모일아미노]-N-에틸벤자미드;
- 2-[(4,6-디메톡시피리미딘-2-일)카바모일술파모일아미노]-N-메톡시벤자미드;
- 2-[(4,6-디메톡시피리미딘-2-일)카바모일술파모일아미노]-N-메톡시-N-메틸벤자미드;
- 2-[(4,6-디메톡시피리미딘-2-일)카바모일술파모일아미노]-N-벤자미드;
- 2-[(4,6-디메톡시피리미딘-2-일)카바모일술파모일메틸아미노]-N,N-디메틸벤자미드;
- N-시클로프로필-2-[(4,6-디메톡시피리미딘-2-일)카바모일술파모일아미노]-벤자미드;
- 2-[(4,6-디메톡시피리미딘-2-일)카바모일술파모일아미노]-N-(2,2,2-트리플루오로에틸)벤자미드;
- 4-클로로-6-[(4,6-디메톡시피리미딘-2-일)카바모일술파모일아미노]-N,N-디메틸벤자미드;
- 3-클로로-6-[(4,6-디메톡시피리미딘-2-일)카바모일술파모일아미노]-N,N-디메틸벤자미드;
- 2-[(4,6-디메톡시피리미딘-2-일)카바모일술파모일아미노]-5-플루오로-N,N-디메틸벤자미드;
- 2-[(4,6-디메톡시피리미딘-2-일)카바모일술파모일아미노]-6-플루오로-N,N-디메틸벤자미드;
- 2-[(4,6-디메톡시피리미딘-2-일)카바모일술파모일아미노]-5-메틸-N,N-디메틸벤자미드;
- 2-[(4,6-디메톡시피리미딘-2-일)카바모일술파모일아미노]-6-메틸-N,N-디메틸벤자미드;
- N,N-디메틸-2-[(4-메톡시-6-메틸피리미딘-2-일)카바모일술파모일아미노]-벤자미드;
- N,N-디메틸-2-[(4,6-디메틸피리미딘-2-일)카바모일술파모일아미노]-벤자미드.
화학식 1 의 아미노술포닐우레아는 산성이어서 알카리금속 및 알카리토금속 수산화물, 아민 및 기타 유기염기와 같은 염기성 물질과 염을 형성하거나 4차 아민염이다.
염 형태의 화학식 1 의 아미노술포닐우레아 역시 본 발명의 범위에 속한다.
본 발명의 또다른 목적은 화학식 1 의 화합물 제조방법이다.
화학식 1 의 화합물은 다음 단계에 의해 수득된다:
(a) 화학식 2 의 헤테로고리형 아민을 불활성 유기용매하에서 화학식 3 의 할로술포닐 이소시아네이트와 반응시켜 화학식 4 의 할로술파모일우레아를 수득하며;
여기서, R4, R5, R6 및 Z 는 위에서 기술된 것과 동일한 의미를 가지며
여기서 X 는 염소, 불소 또는 브롬과 같은 할로겐 원자, 특히 염소이며
여기서 X, R4, R5, R6및 Z 는 위와 동일한 의미를 가지며
(b) 단계(a)에서 수득된 화학식 4 의 할로술파모일우레아를 염기의 존재 또는 부재하에서, 특히 염기와 불활성 용매의 존재하에서 화학식 5 의 아닐린과 반응시키는 단계.
여기서 R, R1, R2및 R3는 위와 동일한 의미를 가진다.
단계(a) 및 (b)에서 사용된 불활성 유기용매는 방향족 탄화수소(예, 벤젠, 톨루엔, 크실렌), 염소첨가된 탄화수소(예, 염화메틸렌, 클로로포름, 사염화탄소, 클로로벤젠) 및 에테르(예, 에틸에테르, 디메톡시에탄, 테트라히드로퓨란)이다.
단계 (b)에서 유용한 염기는 지방족 아민과 같은 유기염기, 예컨대 트리에틸아민이다.
단계 (a) 및 (b)는 -70℃와 사용된 용매의 비점사이의 온도, 특히 -20 내지 30℃에서 수행된다.
화학식 5 의 아닐린과 화학식 4 의 할로술파모일우레아간의 반응단계(b)는 아닐린(화학식 5)과 염기(단계(a)에 사용된 유기 용매로 희석된)를 첨가함으로써 상기 할로술파모일우레아(화학식 4)를 분리시키지 않고도 수행될 수 있다.
화학식 2 의 헤테로고리형 아민과 화학식 3 의 할로술포닐이소시아네이트는 당해 분야에서 공지된 화합물이다.
화학식 5 의 아닐린은 당해분야에서 공지된 방법에 따라 제조될 수 있다.
화학식 1 의 화합물은 생물학적 활성, 특히 높은 제초능을 가지므로 잡초로부터 유용한 작물을 보호하는데 사용하기 적합하다.
특히, 화학식 1 의 화합물은 수많은 쌍떡잎 잡초의 발생전후에 잡초를 조절하는데 효과적이다. 동시에 이 화합물은 잡초 발생전후에 처리하는 동안 유용한 작물에 대해 독성을 보이지 않는다.
화학식 1 의 화합물을 사용함으로써 효과적으로 조절되는 잡초의 예는 다음과 같다: 어저귀속 테오프라스티(Abutilon theofrasti), 아마란스 레트로플렉서스(Amaranthus retroflexus), 암니 마이우스(Amni maius), 캡셀라 버사 파스토리스(Capsella bursa pastoris), 케노포듐 앨범(Chenopodium Album), 콘볼부루스 세퓸(Convolvulus sepium), 갈륨 아파린(Galium Aparine), 제라늄 디코토미플로룸(Geranium dicotomiflorum), 이포미아 에스피피.(Ipomea spp.), 매트리카리아 에스피피.(Matricaria spp), 파파베르 로에아스(Papaver rhoeas), 포르툴라카 올레라시나(Portulaca oleracea), 시다 스피노사(Sida spinosa), 솔라늄 니그룸(Solanum nigrum), 스텔라리아 메디아(Stellaria media), 알로페쿠루스 미오수로이데스(Alopecurus myosuroides), 디지타리아 산구닌알리스(Digitaria sanguinalis), 에치노클로아 에스피피.(Echinocloa spp.), 시리푸스 에스피피.(Scirpus spp.), 시페루스 에스피피.(Cyperus spp.).
작물에 유용한 투여량에서 상기 화합물은 쌀(오리자 사티바), 밀(트리티큠 에스피피.), 옥수수(지아 마이스), 콩(글리신 맥스)과 같은 중요한 작물에 독성을 보이지 않는다.
본 발명의 또다른 목적은 화학식 1 의 화합물을 적용함으로써 재배지에서 잡초를 조절하는 방법이다.
필요한 결과를 얻는데 요구되는 화합물의 양은 사용될 화합물, 보존될 작물, 제거될 잡초, 침략 정도, 기후 조건, 토양 특성, 적용 방법과 같은 여러 인자에 따라 가변적이다.
1 헥타아르당 1 내지 1000g의 화합물 투여량이 적당하다.
실제 농업분야에서 활성성분으로서 하나 이상의 화학식 1 화합물을 포함한 제초능을 가진 조성물 또는 이성질체와 화합물을 염형태 또는 유리형태로 사용한다.
건조분말, 습윤가능한 분말, 유화가능한 농축물, 마이크로에멀젼, 페이스트, 과립, 용액, 현탁액 형태의 화합물을 사용할 수 있으며 조성물의 형태는 사용분야에 달려있다.
조성물은 활성 물질을 계면활성제 존재하에서 용매 또는 고체 매체에 희석 또는 용해시킴으로써 제조될 수 있다.
고체 불활성 희석제 또는 담체로 사용될 물질은 카올린, 알루미나, 실리카, 탈크, 벤토나이트, 석고, 석영, 돌로마이트, 아타풀자이트, 몬트모릴로나이트, 규조트, 셀룰로오스, 전분등이다.
불활성 액체 희석제로 사용될 물질은 물에 추가적으로 방향족 탄화수소(크실렌, 알킬벤젠 혼합물), 지방족 탄화수소(헥산, 시클로헥산), 방향족 할로겐화 탄화수소(클로로벤젠), 알콜(메탄올, 프로판올, 부탄올, 옥탄올), 에테르(이소부틸아세테이트), 케톤(아세톤, 시클로헥사논, 아세토페논, 이소포론, 에틸아밀케톤), 식물 오일, 광물 오일 및 그 혼합물이다.
계면활성제로서 비이온성(폴리에톡실화 알킬페놀, 폴리에톡실화 지방알콜), 음이온성(알킬벤젠술포네이트, 알킬술포네이트), 양이온성(4차 알킬암모늄염)을 갖는 습윤제 및 유화제가 사용된다.
분산제(리그닌 및 그 염, 셀룰로오스 유도체, 알기네이트), 안정화제(항산화제, 자외선 흡수제)를 첨가할 수도 있다.
조성물의 작용 범위를 증가시키기 위해서 다른 제초제, 살균제, 살충제 또는 진드기 제거제 및 비료와 같은 다른 활성성분이 첨가될 수 있다. 화학식 1 화합물을 하나 이상 함유한 조성물에 첨가될 수 있는 다른 제초제의 예는 다음과 같다:
아세토클로르(Acetochlor), 아시플루오르펜(acifluorfen), 아클로니펜 (aclonifen), AKH-7088, 알라클로르(alachlor), 알록시딤(alloxydim), 아메트린 (ametryn), 아미도술푸론(amidosulfuron), 아미크롤레(amicrole), 아닐로포스 (anilofos), 아수람(asulam), 아트라진(atrazine), 아자페니딘(azafenidin) (DPX-R6447), 아짐술푸론(azimsulfuron) (DPX-A8947), 아지프로트린(aziprotrine), 벤아졸린(benazolin), 벤플루랄린(benfluralin), 벤푸레세이트(benfuresate), 벤술푸론 (bensulfuron), 벤술리드(bensulide), 벤타존(bentazone), 벤조페납(benzofenap), 벤즈티아주론(benzthiazuron), 비페녹스(bifenox), 빌라노포스(bilanafos), 비스피리박-소듐(bispyribac-sodium)(KIH-2023), 브로마실(bromacil), 브로모부티드 (bromobutide), 브로모페녹심(bromofenoxim), 브로모옥시닐(bromoxynil), 부타클로르(butachlor), 부타미포스(butamiphos), 부텐아클로르(butenachlor), 부트랄린 (butralin), 부트록시딤(butroxydim), 부틸레이트(butylate), 카펜스트롤 (cafenstrole) (CH-900), 카베타미드 (carbetamide), 카펜트라존-에틸 (carfentrazone-ethyl) (F-8426), 클로로메톡시펜(chloromethoxyfen), 클로람벤 (chloramben), 클로르브로무론(chlorbromuron), 클로르부팜(chlorbufam), 클로르푸레놀(chlorfurenol), 클로리다존(chloridazon), 클로리무론(chlorimuron), 클로르니트로펜(chlornitrofen), 클로르톨루론(chlorotoluron), 클로록수론 (chloroxuron), 클로로프로팜(chlorpropham), 클로르술포론(chlorsulforon), 클로르탈(chlorthal), 클로르티아미드(chlorthiamid), 시니돈 에틸(cinidon ethyl), 신메틸린(cinmethylin), 시노술푸론(cinosulfuron), 클레토딤(clethodim), 클로디나폽(chlodinafop), 클로마존(clomazone), 클로메프롭(clomeprop), 클로피랄리드 (clopyralid), 클로란술람-메틸(chloransulam-methyl) (XDE-565), 큐밀유론 (cumyluron) (JC-940), 시아나진(cyanazine), 시클로에이트(cycloate), 시클로술팜우론(cyclosulfamuron) (AC-322140), 시클록시딤(cycloxydim), 시할로폽-부틸 (cyhalofop-butyl) (XDE-537), 2,4-D, 2,4-DB, 다이무론(daimuron), 달라폰 (dalapon), 데스네디팜(desnedipham), 데스메트린(desmetryn), 디캄바(dicamba), 디클로벤일(dichlobenil), 디클로르프롭(dichlorprop), 디클로르프롭-P (dichlorprop-P), 디클로폽(diclofop), 디클로술람(diclosulam) (XDE-564), 디에타틸(diethatyl), 디페녹스우론(difenoxuron), 디펜조쿠아트(difenzoquat), 디플루페니칸(diflufenican), 디플루펜조피르(diflufenzopyr) (SAN 835H), 디메푸론 (dimefuron), 디메피페레이트(dimepiperate), 디메타클로르(dimethachlor), 디메타메트린(dimethametryn), 디메틴아미드(dimethenamid), 디니트라민(dinitramine), 디노셉(dinoseb), 디노셉 아세테이트(dinoseb acetate), 디노터브(dinotherb), 디펜아미드(diphenamid), 디프로페트린(dipropetryn), 디쿠아트(diquat), 디티오피르 (dithiopyr), 1-디유론(1-diuron), 에글리나진(eglinazine), 에토탈(endothal), 에포프로단(epoprodan) (MK-243), EPTC, 에스프로카브(esprocarb), 에탈플루랄린 (ethalfluralin), 에타메트술푸론-메틸(ethametsulfuron-methyl) (DPX-A7881), 에티디무론(ethidimuron), 에티오진(ethiozin) (SMY 1500), 에토퓸세이트 (ethofumesate), 에톡시펜-에틸(ethoxyfen-ethyl) (HC-252), 에톡시술푸론 (ethoxysulfuron) (HOE 095404), 에토벤즈아니드(ethobenzanid) (HW 52), 페녹사프로프(fenoxaprop), 페녹사프로프-P(fenoxaprop-P), 펜트라즈아미드(fentrazamide) (BAY YRC 2388), 펜우론(fenuron), 플레임프로프(flamprop), 플레임프로프 (flamprop-M), 플라자술푸론(flazasulfuron), 플루아지포프(fluazifop), 플루아지포프-P(fluazifop-P), 플루클로랄린(fluchloralin), 플루메트술람(flumetsulam) (DE-498), 플루미클로락-펜틸(flumiclorac-pentyl), 플루미옥사진(flumioxazin), 플루미프로핀(flumipropin), 플루메트우론(flumeturon), 플로오로글리코펜 (fluoroglycofen), 플루오로니트로펜(fluoronitrofen), 플루폭삼(flupoxam), 플루프로판에트(flupropanate), 플루피르술푸론(flupyrsulfuron) (DPX-KE459), 플루레놀(flurenol), 플루리돈(fluridone), 플루클로리돈(flurochloridone), 플루록시피르(fluroxypyr), 플루타몬(flurtamone), 플루티아세트-메틸(fluthiacet-methyl) (KIH-9201), 플루티아미드(fluthiamide) (BAY FOE 5043), 포메사펜(fomesafen), 포사민(fosamine), 푸릴옥시펜(furyloxyfen), 글루포시네이트(glufosinate), 글리포세이트(glyphosate), 할로술푸론-메틸(halosulfuron-methyl) (NC-319), 할록시포프 (haloxyfop), 할록시포프-P-메틸(haloxyphop-P-methyl), 헥사지논(hexazinone), 이마자메타벤즈(imazamethabenz), 이마자목스(imazamox) (AC-299263), 이마자픽 (imazapic) (AC-263222), 이마자피르(imazapyr), 아마자퀸(amazaquin), 이마제타피르(imazethapyr), 이마조술푸론(imazosulfuron), 이옥시닐(ioxynil), 이소프로팔린 (isopropalin), 이소프로파졸(isopropazol) (JV 485), 이소프로투론(isoproturon), 이소우론(isouron), 이소작벤(isoxaben), 이소자플루톨(isoxaflutole) (RPA 201772), 이소자피리포프(isoxapyrifop), KPP-421, 락토펜(lactofen), 레나실 (lenacil), 리누론(linuron), LS830556, MCPA, MCPA-티오에틸(MCPA-thioethyl), MCPB, 메코프로프(mecoprop), 메코프로프-P(mecoprop-P), 메펜아세트(mefenacet), 메타미트론(metamitron), 메타자클로르(metazachlor), 메타벤즈티아즈우론 (methabenzthiazuron), 메타졸(methazole), 메토프로트린(methoprotryne), 메틸딤론(methyldymron), 메토벤즈우론(metobenzuron), 메타브롬우론(metobromuron), 메톨라클로르(metolachlor), 메토술람(metosulam) (DE-511), 메톡스우론(metoxuron), 메트리부진(metribuzin), 메트술푸론(metsulfuron), 몰리네이트(molinate), 모날리드(monalide), 모놀린우론(monolinuron), 나프로아닐리드(naproanilide), 나프로프아미드(napropamide), 나프탈람(naptalam), NC-330, 네부론(neburon), 니코술푸론 (nicosulfuron), 니프르아클로펜(nipyraclofen), 노르플루라존(norflurazon), 오벤카브(orbencarb), 옥시잘린(oryzalin), 옥사디아질(oxadiargyl), 옥사디아존 (oxadiazon), 옥사술푸론(oxasulfuron) (CGA-277476), 옥사지클로메폰 (oxaziclomefone) (MY-100), 옥시플루오르펜(oxyfluorfen), 파라큐아트(paraquat), 페불레이트(pebulate), 펜디메탈린(pendimethalin), 펜타노클로르(pentanochlor), 펜톡사존(pentoxazone) (KPP-314), 펜메디팜(phenmedipham), 피클로람(picloram), 피페로포스(piperophos), 프레닐아클로르(prenilachlor), 프리미술푸론 (primisulfuron), 프로디아민(prodiamine), 프로글리나진(proglinazine), 프로메톤 (prometon), 프로메트린(prometryne), 프로파클로르(propachlor), 프로판일 (propanil), 프로파퀴자포프(propaquizafop), 프로파진(propazine), 프로팜 (propham), 프로피소클로르(propisochlor), 프로피자미드(propyzamide), 프로술포카브(prosulfocarb), 프로술푸론(prosulfuron)(CGA-152005), 피라플루펜-에틸 (pyraflufen-ethyl) (ET-751), 피라졸리네이트(pyrazolynate), 피라졸술푸론 (pyrazolsulfuron), 피라족시펜(pyrazoxyfen), 피리벤족심(pyribenzoxim) (LGC-40863), 피리부티카브(pyributicarb), 피리데이트(pyridate), 피리민오박-메틸 (pyriminobac-methyl) (KIH-6127), 피리티오박-소듐(pyrithiobac-sodium) (KIH-2031), 퀸클로락(quinchlorac), 퀸메락(quinmerac), 퀴즈알로포프(quizalofop), 퀴잘로포프-P(quizalofop-P), 리마술푸론(rimasulfuron), 세톡시딤(sethoxydim), 시드우론(siduron), 시마진(simazine), 시메트린(simetryn), 술코트리온 (sulcotrione), 술펜트라존(sulfentrazone) (F6285), 술포메투론(sulfometuron) (DPX-5648), 술포술푸론(sulfosulfuron) (MON 37500), 2,3,6-TBA, TCA-소듐(TCA-sodium), 테부탐(tebutam), 테부티우론(tebuthiuron), 테프랄옥시딤(tepraloxydim) (BAS 620H), 터바실(terbacil), 터부메톤(terbumeton), 터부틸-아진(terbuthyl-azine), 터부티린(terbutryn), 테릴클로르(therylchlor) (NSK-850), 티아자플루론 (thiazafluron), 티아조피르(thiazopyr) (MON 13200), 티디아지민(thidiazimin), 티펜술푸론(thifensulfuron), 티오엔카브(thioencarb), 티오카브아질 (tiocarbazil), 티오클로림(tioclorim), 트랄콕시딤(tralkoxydim), 트리-알레이트 (tri-allate), 트리아술푸론(triasulfuron) (CGA-131036), 트리악스플람 (triaxiflam) (IDH-1105), 트리벤우론(tribenuron), 트리클로피르(triclopyr), 트리에타진(trietazine), 트리플루랄린(trifluralin), 트리플루실푸론-메틸 (triflusilfuron-methyl) (DPX-66037), UBI-C4874, 버놀레이트(vernolate).
화학식 1 활성성분의 농도는 활성 화합물 종류, 용도, 환경조건 및 배합물 종류에 따라 다양하다. 일반적으로 활성성분의 농도는 1 내지 90%, 특히 5 내지 50%이다.
실시예 1: 2-[(4,6-디메톡시피리미딘-2-일)카바모일술파모일아미노]-N,N-디메틸벤즈아미드(화합물 제 1) 제조
질소대기 하에서 염화메틸렌(10㎖)에 용해된 클로로술포닐 이소시아네이트(4.3g; 30.5mmol)가 염화메틸렌(50㎖)에 든 2-아미노-4,6-디메톡시피리미딘(5.2g; 33.6mmol)에 -5℃에서 적가된다.
혼합물을 1시간동안 0℃에서 교반한다. 염화메틸렌(20㎖)에 든 트리에틸렌아민(3.1g; 30.6mmol)과 2-아미노-N,N-디메틸벤즈아미드(5g; 30.5mmol) 용액이 첨가되고 혼합물을 0℃에서 30분간 교반하고 실온에서 3시간 교반한다. 반응 혼합물을 염과 1% 수성 HCl의 용액 2ℓ에 붓고 염화메틸렌으로 추출한다. 염으로 유기상을 세척하고 황산나트륨으로 건조하고 감압하에서 농축한다. 잔류물(12.8g)을 50℃에서 에틸 아세테이트와 함께 교반한다. 냉각후 고체를 여과하고 디에틸에테르를 써서 세척한다. 생성물(11.3g)은 160-162℃의 융점을 가진다.
실시예 2
실시예 1 에 기술된 것과 유사하게 적절한 2-아미노피리미딘과 2-아미노벤즈아미드에서 시작하여 다음 화합물이 제조된다:
- 1-(4,6-디메톡시피리미딘-2-일)-{[2-(1-피롤리디노카르보닐)페닐]술파모일}우레아 (화합물 제 2): m.p. 154-156℃;
- 2-(4,6-디메톡시피리미딘-2-일)카바모일술파모일아미노]-N-에틸-N-메틸벤자미드 (화합물 제 3): m.p. 136-138℃;
- 2-(4,6-디메톡시피리미딘-2-일)카바모일술파모일아미노]-N-메틸벤자미드 (화합물 제 4): m.p. 98-100℃;
- 2-(4,6-디메톡시피리미딘-2-일)카바모일술파모일아미노]-N-에틸벤자미드 (화합물 제 5): m.p. 98-100℃;
- 2-(4,6-디메톡시피리미딘-2-일)카바모일술파모일아미노]-N-메톡시벤자미드 (화합물 제 6): m.p. 147-149℃;
- 2-(4,6-디메톡시피리미딘-2-일)카바모일술파모일아미노]-N-메톡시-N-메틸벤자미드 (화합물 제 7): m.p. 137-139℃;
- 2-(4,6-디메톡시피리미딘-2-일)카바모일술파모일아미노]벤자미드 (화합물 제 8): m.p. 164-166℃;
- 2-(4,6-디메톡시피리미딘-2-일)카바모일술파모일아미노]-N,N-디메틸벤자미드 (화합물 제 9): m.p. 120-121℃;
- N-시클로프로필-2-(4,6-디메톡시피리미딘-2-일)카바모일술파모일아미노)벤자미드 (화합물 제 10);
- 2-(4,6-디메톡시피리미딘-2-일)카바모일술파모일아미노]-N-(2,2,2-트리플루오로에틸)-벤자미드 (화합물 제 11);
- 4-클로로-6-[(4,6-디메톡시피리미딘-2-일)카바모일술파모일아미노]-N,N-디메틸벤자미드 (화합물 제 12): m.p. 161-163℃;
- 3-클로로-6-[(4,6-디메톡시피리미딘-2-일)카바모일술파모일아미노]-N,N-디메틸벤자미드 (화합물 제 13): m.p. 156-158℃;
- 2-(4,6-디메톡시피리미딘-2-일)카바모일술파모일아미노)-5-플루오로-N,N-디메틸벤자미드 (화합물 제 14): m.p. 171-173℃;
- 2-(4,6-디메톡시피리미딘-2-일)카바모일술파모일아미노]-6-플루오로-N,N-디메틸벤자미드 (화합물 제 15): m.p. 165-167℃;
- 2-(4,6-디메톡시피리미딘-2-일)카바모일술파모일아미노]-5-메틸-N,N-디메틸벤자미드 (화합물 제 16): m.p. 164-166℃;
- 2-(4,6-디메톡시피리미딘-2-일)카바모일술파모일아미노]-6-메틸-N,N-디메틸벤자미드 (화합물 제 17): m.p. 169-171℃;
- N,N-디메틸-2-[(4-메톡시-6-메틸피리미딘-2-일)카바모일술파모일아미노]벤자미드 (화합물 제 18): m.p. 147-149℃;
- N,N-디메틸-2-[(4,6-디메틸피리미딘-2-일)카바모일술파모일아미노]벤자미드 (화합물 제 19): m.p. 163-165℃;
실시예 3: 2-[(4,6-디메톡시피리미딘-2-일)카바모일술파모일아미노]-N,N-디메틸벤자미드 모노소듐염 (화합물 제 20) 제조
수산화나트륨(400㎎; 10mmol)을 디클로로메탄 100㎖에든 화합물 제 1 (실시예 1; 4.25g; 10mmol) 용액에 첨가한다.
혼합물을 실온에서 18시간 교반하고 감압하에서 농축한다. 고체 잔류물(4.3g)은 190℃의 융점을 가진다.
실시예 4 : 제초능력 및 독성 결정
미국특허 4,515,620 (RC)의 실시예 2 에 발표된 1-[(4,6-디메톡시피리미딘-2-일)-3-[(2-메톡시카르보닐페닐)술파모일)우레아와 비교하여 잡초 발생후 처리시 잡초에 대한 화합물 제 1, 2 및 4 의 제초능력과 밀에 대한 독성이 평가된다.
각 화합물의 경우에 다음 절차에 따라서 평가가 수행되었다.
사토를 담은 단지(직경 10㎝, 높이 10㎝)가 준비되고 다음 식물이 심어진다:
잡초 : 아뷰틸론 테오프라스티(ABUTH), 아마란스 리트로플렉서스(AMARE), 암니 마이우스(MNMA), 콘볼불러스 세퓐(CONSE), 갈륨 아파린(GALAP), 이포미아 퍼퓨리아(IPOPU), 파파베르 로에아스(PAPRH), 솔라늄 니그룸(SOLNI)
작물 : 트리티큠 에스피. (밀)
각 단지에 씨앗의 발아에 충분한 양의 물이 첨가된다. 단지를 두 그룹으로 나누며, 제 1 그룹은 화합물로 처리되지 않은 것으로 비교용이며 제 2 그룹은 잡초를 심은지 15일후, 밀을 심은지 10일후 화합물과 Tween 20 (0.5%)을 포함한 히드로아세톤 분산물(20부피% 아세톤)로 처리한다.
모든 단지는 다음 조건하에 유지한다:
- 온도 : 24℃
- 상대습도 : 60%
- 조광 기간 : 16시간
- 광도 : 10,000룩스
식물의 양호한 성장을 위한 충분한 습도를 유지하기 위해 이틀마다 단지에 물을 준다.
처리 21일후 처리 안된 것에 비해서 처리된 식물의 손상 비율을 기초로 제초능력이 평가된다.
0 = 0 - 9% 손상
1 = 10 - 29% 손상
2 = 30 - 49% 손상
3 = 50 - 69% 손상
4 = 70 - 89% 손상
5 = 90% 손상 - 식물 사망
수득된 결과는 표 1 에 도시된다.
| 잡초/작물 | 화합물(g/헥타아르) | Nr.1150-50 | Nr.2150-50 | Nr.4150-50 | RC150-50 |
| ABUTH | 5 - 3 | 4 - 2 | 5 - 3 | 5 - 2 | |
| AMARE | 5 - 3 | 1 - 0 | 5 - 4 | 3 - 1 | |
| AMNMA | 4 - 3 | 4 - 3 | 5 - 4 | 2 - 1 | |
| CONSE | 5 - 5 | 5 - 5 | 5 - nt | 3 - 1 | |
| GALAP | 5 - 3 | 4 - 1 | 5 - 4 | 4 - 2 | |
| IPOPU | 5 - 3 | nt - nt | 5 - 4 | nt - 0 | |
| PAPRH | 5 - 4 | 5 - 4 | nt - nt | nt - 0 | |
| SOLNI | 5 - 3 | 3 - 2 | nt - nt | nt - 0 | |
| WHEAT | 0 - 0 | 0 - 0 | 0 - 0 | 0 - 0 |
nt = 테스트 안됨.
Claims (21)
- 화학식 1 의 아미노술포닐우레아:여기서, - R 은 염소, 불소, 브롬 또는 요오드와 같은 할로겐 원자; 직쇄형 또는 측쇄형 알킬 또는 할로알킬 C1-C4기; 직쇄형 또는 측쇄형 알콜 또는 할로알콜 C1-C4기이며- N 은 0 또는 1 이고- R1및 R2는 동일 또는 상이하며 수소원자; 직쇄 또는 측쇄형 알킬 또는 할로알킬 C1-C4기; 직쇄 또는 측쇄형 알콜 또는 할로알콜 C1-C4기; 또는 결합하여 알켄일 또는 옥시알켄일 C2-C5체인이며- R3및 R4는 동일 또는 상이하며 수소원자; 직쇄 또는 측쇄형 알킬 또는 할로알킬 C3-C6기; 직쇄 또는 측쇄형 알켄일 또는 할로알켄일 C3-C6기; 직쇄 또는 측쇄형 알킨일 또는 할로알킨일 C3-C6기이며- R5및 R6는 동일 또는 상이하며 수소원자; 염소, 불소, 브롬 또는 요오드와 같은 할로겐 원자; 직쇄 또는 측쇄형 알킬 또는 할로알킬 C1-C6기; 직쇄 또는 측쇄형 알킬아민 C1-C6기; 직쇄 또는 측쇄형 디알킬 아민 C2-C8기; 시클로알킬 또는 시클로알콕실 C3-C6기; 시클로알킬알킬 또는 시클로알킬알콕실 C4-C7기이며- Z 는 CH 또는 N 이다.
- 화학식 1을 가진 아미노술포닐우레아로 구성된 제초제:여기서, - R 은 염소, 불소, 브롬 또는 요오드와 같은 할로겐 원자; 직쇄형 또는 측쇄형 알킬 또는 할로알킬 C1-C4기; 직쇄형 또는 측쇄형 알콜 또는 할로알콜 C1-C4기이며- N 은 0 또는 1 이고- R1및 R2는 동일 또는 상이하며 수소원자; 직쇄 또는 측쇄형 알킬 또는 할로알킬 C1-C4기; 직쇄 또는 측쇄형 알콜 또는 할로알콜 C1-C4기; 또는 결합하여 알켄일 또는 옥시알켄일 C2-C5체인이며- R3및 R4는 동일 또는 상이하며 수소원자; 직쇄 또는 측쇄형 알킬 또는 할로알킬 C3-C6기; 직쇄 또는 측쇄형 알켄일 또는 할로알켄일 C3-C6기; 직쇄 또는 측쇄형 알킨일 또는 할로알킨일 C3-C6기이며- R5및 R6는 동일 또는 상이하며 수소원자; 염소, 불소, 브롬 또는 요오드와 같은 할로겐 원자; 직쇄 또는 측쇄형 알킬 또는 할로알킬 C1-C6기; 직쇄 또는 측쇄형 알킬아민 C1-C6기; 직쇄 또는 측쇄형 디알킬 아민 C2-C8기; 시클로알킬 또는 시클로알콕실 C3-C6기; 시클로알킬알킬 또는 시클로알킬알콕실 C4-C7기이며- Z 는 CH 또는 N 이다.
- 제 2항에 있어서, 2-[(4,6-디메톡시피리미딘-2-일)카바모일술파모일아미노]-N,N-디메틸-벤자미드로 구성된 제초제.
- 제 2 항에 있어서, 1-[(4,6-디메톡시피리미딘-2-일)-3-{[2-(1-피롤리도노카르보닐)페닐]술파모일}우레아로 구성된 제초제.
- 제 2항에 있어서, 2-[(4,6-디메톡시피리미딘-2-일)카바모일술파모일아미노]-N-메틸벤자미드로 구성된 제초제.
- 제 2항에 있어서, 2-[(4,6-디메톡시피리미딘-2-일)카바모일술파모일아미노]-N-에틸벤자미드로 구성된 제초제.
- 제 2항에 있어서, 2-[(4,6-디메톡시피리미딘-2-일)카바모일술파모일아미노]-N-메톡시벤자미드로 구성된 제초제.
- 제 2항에 있어서, 2-[(4,6-디메톡시피리미딘-2-일)카바모일술파모일아미노]-N-메톡시-N-메틸벤자미드로 구성된 제초제.
- 다음 단계로 구성된 화학식 1 의 아미노술포닐우레아 제조방법:(a) 화학식 2 의 헤테로고리형 아민을 불활성 유기용매하에서 화학식 3 의 할로술포닐이소시아네이트와 반응시켜 화학식 4 의 할로술파모일우레아를 수득하며;여기서, R4, R5, R6및 Z 는 위에서 기술된 것과 동일한 의미를 가지며X-SO2-NCO여기서 X 는 염소, 불소 또는 브롬과 같은 할로겐 원자, 특히 염소이며여기서 X, R4, R5, R6및 Z 는 위와 동일한 의미를 가지며(b) 단계(a)에서 수득된 화학식 4 의 할로술파모일우레아를 염기의 존재 또는 부재하에서, 특히 염기와 불활성 용매의 존재하에서 화학식 5 의 아닐린과 반응시키는 단계여기서 R, R1, R2및 R3는 위와 동일한 의미를 가진다.
- 제 9 항에 있어서, 단계 (a) 및 (b)에서 사용된 불활성 유기 용매가 방향족 탄화수소, 염소첨가된 탄화수소 또는 에테르에서 선택됨을 특징으로 하는 방법.
- 제 9 항 또는 10 항에 있어서, 단계 (b)의 유기 염기가 지방족 아민에서 선택됨을 특징으로 하는 방법.
- 제 9 항 내지 11 항중 한 항에 있어서, 단계 (a) 및 (b)가 -70℃와 사용된 용매의 비점 사이의 온도에서 수행됨을 특징으로 하는 방법.
- 제 12 항에 있어서, 단계 (a) 및 (b)가 -20 내지 30℃에서 수행됨을 특징으로 하는 방법.
- 제 9 항에 있어서, 화학식 Ⅴ의 아닐린과 화학식 4 의 할로술파모일우레아간의 반응단계(b)가 단계 (a)에서 사용된 불활성 유기용매로 희석된 유기 염기와 아닐린(화학식 5)을 직접 첨가하여 상기 할로술파모일우레아(화학식 4)를 분리시키지 않고 수행됨을 특징으로 하는 방법.
- 단독으로 또는 고체 담체, 액체 희석제, 계면활성제 또는 기타 활성성분과 조합으로 청구항 제 2 내지 8 중 한 항에 따른 아미노술포닐우레아를 포함하는 제초능력을 갖는 조성물.
- 제 15 항에 있어서, 활성물질의 농도가 1 내지 90%임을 특징으로 하는 조성물.
- 재배지에 청구항 15 및 16 의 조성물을 적용하는 것으로 구성된 잡초 조절 방법.
- 제 1 항 내지 8 항에 따른 화학식 1 의 아미노술포닐우레아의 알카리 금속, 알카리토금속, 알킬화 암모늄 또는 유기 아민염.
- 단독으로 또는 고체 담체, 액체 희석제, 계면활성제 또는 기타 활성성분과 조합으로 제 18 항에 따른 화학식 1 아미노술포닐우레아의 염을 포함한 제초제 조성물.
- 제 19 항에 있어서, 활성 물질의 농도가 1 내지 90%임을 특징으로 하는 조성물.
- 재배지에 제 19 항 및 20 항에 따른 조성물을 적용하는 단계로 구성된 잡초 조절방법.
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| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| ITMI97A000554 | 1997-03-13 | ||
| IT97MI000554A IT1290062B1 (it) | 1997-03-13 | 1997-03-13 | Amminosolfoniluree ad attivita' erbicida |
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| Publication Number | Publication Date |
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| KR20000076184A true KR20000076184A (ko) | 2000-12-26 |
| KR100356385B1 KR100356385B1 (ko) | 2002-10-19 |
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| KR1019997008278A KR100356385B1 (ko) | 1997-03-13 | 1998-03-09 | 아미노술포닐우레아 제초제 |
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| US (1) | US6329323B1 (ko) |
| EP (1) | EP0971902B1 (ko) |
| JP (1) | JP4351741B2 (ko) |
| KR (1) | KR100356385B1 (ko) |
| CN (2) | CN1129585C (ko) |
| AT (1) | ATE211133T1 (ko) |
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| DE (1) | DE69803048T2 (ko) |
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| ES (1) | ES2165151T3 (ko) |
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| DE102004062541A1 (de) * | 2004-12-24 | 2006-07-06 | Bayer Cropscience Ag | Synergistische herbizide Wirkstoffkombination |
| ITMI20062368A1 (it) | 2006-12-11 | 2008-06-12 | Isagro Spa | Composizioni erbicide |
| EP2052606A1 (de) | 2007-10-24 | 2009-04-29 | Bayer CropScience AG | Herbizid-Kombination |
| DE102008037620A1 (de) | 2008-08-14 | 2010-02-18 | Bayer Crop Science Ag | Herbizid-Kombination mit Dimethoxytriazinyl-substituierten Difluormethansulfonylaniliden |
| CN102020613B (zh) * | 2009-09-21 | 2012-11-07 | 中国中化股份有限公司 | 具有除草活性的氨基磺酰脲类化合物及其应用 |
| ES2891316T3 (es) | 2010-10-15 | 2022-01-27 | Bayer Cropscience Ag | Uso de herbicidas inhibidores de ALS para el control de vegetación indeseada en plantas Beta vulgaris tolerantes a herbicidas inhibidores de ALS |
| AU2012251597B2 (en) | 2011-05-04 | 2015-11-05 | Bayer Intellectual Property Gmbh | Use of ALS inhibitor herbicides for control of unwanted vegetation in ALS inhibitor herbicide tolerant Brassica, such as B. napus, plants |
| MA38173B2 (fr) | 2012-12-13 | 2017-12-29 | Bayer Cropscience Ag | Utilisation d'herbicides inhibiteurs de l'als pour la lutte contre une végétation indésirable chez des plantes de type betterave fourragère tolérantes aux herbicides inhibiteurs de l'als |
| CN103288750A (zh) * | 2013-03-04 | 2013-09-11 | 盐城工学院 | 新型氨基磺酰脲类化合物 |
| CN103288749A (zh) * | 2013-03-04 | 2013-09-11 | 盐城工学院 | 可作除草剂的氨基磺酰脲类化合物 |
| CN104365641B (zh) * | 2014-10-30 | 2017-07-28 | 广东中迅农科股份有限公司 | 一种含有嘧苯胺磺隆和嘧草醚的除草组合物 |
| CN104430448B (zh) * | 2014-11-25 | 2017-07-28 | 广东中迅农科股份有限公司 | 一种含有嘧苯胺磺隆和嘧啶肟草醚的农药组合物 |
| CN104770382A (zh) * | 2015-04-03 | 2015-07-15 | 北京燕化永乐生物科技股份有限公司 | 一种除草组合物 |
| CN106332902A (zh) * | 2015-07-14 | 2017-01-18 | 江苏扬农化工股份有限公司 | 一种含草铵膦与磺酰脲类除草剂的除草组合物及其应用 |
| CN110612278A (zh) | 2017-03-09 | 2019-12-24 | 贝尔维迪尔弗里叶有限责任公司 | 苗后除草剂 |
| GB201721185D0 (en) | 2017-12-18 | 2018-01-31 | Nodthera Ltd | Sulphonyl urea derivatives |
| WO2020249667A1 (en) | 2019-06-12 | 2020-12-17 | NodThera Limited | Sulfonylurea derivatives and uses thereof |
| EP4415527A1 (en) | 2021-10-15 | 2024-08-21 | KWS SAAT SE & Co. KGaA | Als inhibitor herbicide tolerant beta vulgaris mutants |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4414840A (en) * | 1980-02-22 | 1983-11-15 | Nippon Soken, Inc. | Knock detecting apparatus for internal combustion engines |
| CH649081A5 (de) * | 1982-01-12 | 1985-04-30 | Ciba Geigy Ag | Triaza-verbindungen. |
| CA1235450A (en) * | 1983-05-11 | 1988-04-19 | Kazunori Ishii | Flexible heating cable |
| US4696695A (en) * | 1985-10-25 | 1987-09-29 | Ppg Industries, Inc. | Sulfamoyl urea derivatives |
| DE4414840A1 (de) | 1994-04-28 | 1995-11-02 | Bayer Ag | Substituierte Phenylaminosulfonylharnstoffe |
| CZ287105B6 (en) * | 1995-06-06 | 2000-09-13 | American Cyanamid Co | Process for preparing l-{[2-(cyclopropylcarbonyl)phenyl]sulfamoyl}-3-(4,6-dialkoxy-2-pyrimidinyl)urea and intermediates for such preparation process |
| CN100499337C (zh) * | 2006-12-12 | 2009-06-10 | 浙江大学 | 高增益隔离式有源箝位升压型变换器 |
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| IL131855A (en) | 2006-08-01 |
| CN1446806A (zh) | 2003-10-08 |
| EP0971902A1 (en) | 2000-01-19 |
| DK0971902T3 (da) | 2002-02-18 |
| JP2001516347A (ja) | 2001-09-25 |
| AU6830698A (en) | 1998-09-29 |
| WO1998040361A1 (en) | 1998-09-17 |
| ES2165151T3 (es) | 2002-03-01 |
| EP0971902B1 (en) | 2001-12-19 |
| CN1129585C (zh) | 2003-12-03 |
| JP4351741B2 (ja) | 2009-10-28 |
| DE69803048T2 (de) | 2002-07-11 |
| CU22862A3 (es) | 2003-06-13 |
| BR9808327A (pt) | 2000-05-16 |
| AU727086B2 (en) | 2000-11-30 |
| IT1290062B1 (it) | 1998-10-19 |
| BR9808327B1 (pt) | 2009-05-05 |
| CN1252062A (zh) | 2000-05-03 |
| ID22748A (id) | 1999-12-09 |
| ATE211133T1 (de) | 2002-01-15 |
| ITMI970554A1 (it) | 1998-09-13 |
| US6329323B1 (en) | 2001-12-11 |
| KR100356385B1 (ko) | 2002-10-19 |
| DE69803048D1 (de) | 2002-01-31 |
| PT971902E (pt) | 2002-04-29 |
| OA11157A (en) | 2003-04-17 |
| CN1203064C (zh) | 2005-05-25 |
| CA2283570A1 (en) | 1998-09-17 |
| IL131855A0 (en) | 2001-03-19 |
| CA2283570C (en) | 2008-09-23 |
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