CN1107147A - 取代的苯氨基磺酰脲类除草剂 - Google Patents
取代的苯氨基磺酰脲类除草剂 Download PDFInfo
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- CN1107147A CN1107147A CN94118195A CN94118195A CN1107147A CN 1107147 A CN1107147 A CN 1107147A CN 94118195 A CN94118195 A CN 94118195A CN 94118195 A CN94118195 A CN 94118195A CN 1107147 A CN1107147 A CN 1107147A
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- Prior art keywords
- alkyl
- och
- chlorine
- methyl
- randomly
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- 230000002363 herbicidal effect Effects 0.000 title claims description 5
- 150000001875 compounds Chemical class 0.000 claims abstract description 54
- 238000002360 preparation method Methods 0.000 claims abstract description 22
- 238000000034 method Methods 0.000 claims abstract description 20
- 150000003839 salts Chemical class 0.000 claims abstract description 12
- 239000000460 chlorine Substances 0.000 claims description 124
- -1 sulphinyl Chemical group 0.000 claims description 66
- 125000000217 alkyl group Chemical group 0.000 claims description 38
- 229910052801 chlorine Inorganic materials 0.000 claims description 36
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 34
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 27
- 229910052731 fluorine Inorganic materials 0.000 claims description 27
- 239000011737 fluorine Substances 0.000 claims description 27
- 125000004432 carbon atom Chemical group C* 0.000 claims description 24
- 229910052739 hydrogen Inorganic materials 0.000 claims description 24
- 239000001257 hydrogen Substances 0.000 claims description 24
- 229910052736 halogen Inorganic materials 0.000 claims description 23
- 150000002367 halogens Chemical class 0.000 claims description 23
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 22
- 229910052794 bromium Inorganic materials 0.000 claims description 20
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 19
- 241000196324 Embryophyta Species 0.000 claims description 19
- 150000002431 hydrogen Chemical class 0.000 claims description 18
- 229910052799 carbon Inorganic materials 0.000 claims description 16
- 239000000203 mixture Substances 0.000 claims description 15
- 125000003545 alkoxy group Chemical group 0.000 claims description 13
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- 125000004390 alkyl sulfonyl group Chemical group 0.000 claims description 12
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- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 11
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- 125000003282 alkyl amino group Chemical group 0.000 claims description 9
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- 125000004663 dialkyl amino group Chemical group 0.000 claims description 8
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- 239000013543 active substance Substances 0.000 claims description 6
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 claims description 6
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 6
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims description 6
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 6
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 5
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- 125000003806 alkyl carbonyl amino group Chemical group 0.000 claims description 4
- 125000004448 alkyl carbonyl group Chemical group 0.000 claims description 4
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- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 4
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 4
- 125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 claims description 4
- 125000000031 ethylamino group Chemical group [H]C([H])([H])C([H])([H])N([H])[*] 0.000 claims description 4
- MDQRDWAGHRLBPA-UHFFFAOYSA-N fluoroamine Chemical compound FN MDQRDWAGHRLBPA-UHFFFAOYSA-N 0.000 claims description 4
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 4
- CFHIDWOYWUOIHU-UHFFFAOYSA-N oxomethyl Chemical compound O=[CH] CFHIDWOYWUOIHU-UHFFFAOYSA-N 0.000 claims description 4
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- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 3
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- 125000004455 (C1-C3) alkylthio group Chemical group 0.000 claims description 2
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- 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 2
- 125000004850 cyclobutylmethyl group Chemical group C1(CCC1)C* 0.000 claims description 2
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims description 2
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 2
- 125000004851 cyclopentylmethyl group Chemical group C1(CCCC1)C* 0.000 claims description 2
- 125000005448 ethoxyethyl group Chemical group [H]C([H])([H])C([H])([H])OC([H])([H])C([H])([H])* 0.000 claims description 2
- 125000005745 ethoxymethyl group Chemical group [H]C([H])([H])C([H])([H])OC([H])([H])* 0.000 claims description 2
- 125000002541 furyl group Chemical group 0.000 claims description 2
- 125000001188 haloalkyl group Chemical group 0.000 claims description 2
- 125000001160 methoxycarbonyl group Chemical group [H]C([H])([H])OC(*)=O 0.000 claims description 2
- 125000002816 methylsulfanyl group Chemical group [H]C([H])([H])S[*] 0.000 claims description 2
- 125000006216 methylsulfinyl group Chemical group [H]C([H])([H])S(*)=O 0.000 claims description 2
- 125000004092 methylthiomethyl group Chemical group [H]C([H])([H])SC([H])([H])* 0.000 claims description 2
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 2
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 2
- 125000001544 thienyl group Chemical group 0.000 claims description 2
- 230000002508 compound effect Effects 0.000 claims 1
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- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 10
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 10
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 9
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 9
- 230000000694 effects Effects 0.000 description 9
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 9
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- 239000002904 solvent Substances 0.000 description 8
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- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 6
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- 125000001931 aliphatic group Chemical group 0.000 description 4
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- 239000004459 forage Substances 0.000 description 1
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- XDDAORKBJWWYJS-UHFFFAOYSA-N glyphosate Chemical compound OC(=O)CNCP(O)(O)=O XDDAORKBJWWYJS-UHFFFAOYSA-N 0.000 description 1
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- 125000005842 heteroatom Chemical group 0.000 description 1
- GNOIPBMMFNIUFM-UHFFFAOYSA-N hexamethylphosphoric triamide Chemical compound CN(C)P(=O)(N(C)C)N(C)C GNOIPBMMFNIUFM-UHFFFAOYSA-N 0.000 description 1
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- REEQLXCGVXDJSQ-UHFFFAOYSA-N trichlopyr Chemical compound OC(=O)COC1=NC(Cl)=C(Cl)C=C1Cl REEQLXCGVXDJSQ-UHFFFAOYSA-N 0.000 description 1
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Classifications
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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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C225/00—Compounds containing amino groups and doubly—bound oxygen atoms bound to the same carbon skeleton, at least one of the doubly—bound oxygen atoms not being part of a —CHO group, e.g. amino ketones
- C07C225/20—Compounds containing amino groups and doubly—bound oxygen atoms bound to the same carbon skeleton, at least one of the doubly—bound oxygen atoms not being part of a —CHO group, e.g. amino ketones having amino groups bound to carbon atoms of rings other than six-membered aromatic rings of the carbon skeleton
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Agronomy & Crop Science (AREA)
- Pest Control & Pesticides (AREA)
- Plant Pathology (AREA)
- Health & Medical Sciences (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)
- Plural Heterocyclic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
本发明涉及式(I)的新的取代的苯氨基磺酰脲
类及其盐,它们的制备方法和作为除草剂的用途。式(I)中的R1至R4和R5具有说明书中给出的意义。
Description
本发明涉及新的苯氨基磺酰脲类,它们的制备方法以及作为除草剂的用途。
已经公开了化合物N-(4,6-二甲氧基-嘧啶-2-基)-N′-(2-环丙基-羰基-苯氨基磺酰)-脲可以作为选择性除草剂使用(参见欧洲专利EP-A463287/美国专利5009699)。
在先前的专利申请中公开了一些烷基羰基苯氨基磺酰脲,但尚未受到重视(参见EP-A264467/美国专利4622065)。
现在发现了通式(Ⅰ)的新的取代的苯氨基磺酰脲类及式(Ⅰ)化合物的盐
其中:
R1代表氢、卤素,或者代表烷基、烷氧基、烷硫基、烷基亚磺酰基、烷基磺酰基、烷氨基或二烷氨基,它们在各自的烷基中各有1到4个碳原子,而且均可任选地被卤素或C1-C3烷氧基取代,
R2代表氢或卤素,
R3代表卤素,或者代表烷基、烷氧基、烷硫基、烷基亚磺酰基、烷基磺酰基、烷氨基或二烷氨基,它们在各自的烷基中各有1至4个碳原子,而且均可任选地被卤素或C1-C3烷氧基取代,
R4代表氢、氨基、卤素或甲酰基,或者代表烷基、烷氧基、烷硫基、烷基亚磺酰基、烷基磺酰基、烷基羰基、烷氧基羰基、烷基羰基氨基、烷氧羰基氨基或烷基磺酰基氨基,它们在各自的烷基中各有1到4个碳原子,而且均可任选地被卤素或C1-C3烷氧基取代,和
R5代表氢,或是代表有1到8个碳原子的烷基,该烷基可任选地被卤素、C1-C4烷氧基、C1-C4烷硫基、C1-C4烷基亚磺酰基或C1-C4烷基磺酰基取代,或者代表环烷基、环烷基-C1-C4烷基、环烯基或环烯基-C1-C4烷基,它们在环烷基或环烯基中各有4到7个碳原子,而且均可任选地被卤素和/或C1-C4烷基取代,或者代表均可任选地被卤素、C1-C4烷基或C1-C4卤代烷基取代的苯基或苯基-C1-C4烷基,或者代表有2到6个碳原子和1到3个氮原子以及/或1个氧或硫原子的杂环基或杂环-C1-C4烷基,它们均可任选地被卤素、C1-C4烷基或C1-C4卤代烷基取代。
这种通式(Ⅰ)的新的取代的苯氨基磺酰脲类是通过以下反应制得的:通式(Ⅱ)的氨基嘧啶与异氰酸氯磺酰酯反应,如果合适,在稀释剂存在下反应:
其中R1、R2和R3的意义如上述,此过程中形成的通式(Ⅲ)的氯磺酰脲类与通式(Ⅳ)的芳基胺反应
其中R1、R2、R3、R4和R5的意义如上述,如果合适,此反应在酸性接受体和稀释剂存在下进行,而且如果合适,用常用方法将所形成的式(Ⅰ)化合物转化成盐。
制备本发明式(Ⅰ)化合物的另一种可能的方法概述如下,其中R1、R2、R3、R4和R5的意义同上述,R代表烷基(特别是甲基或乙基)、芳烷基(特别是苄基)或芳基(特别是苯基):
通式(Ⅰ)的新的取代的苯氨基磺酰脲类显示出强有力的和选择性的除草活性。
令人惊奇的是,式(Ⅰ)的新化合物显示出比类似结构的已知化合物N-(4,6-二甲氧基-嘧啶-2-基)-N′-(2-环丙基-羰基-苯氨基磺酰)-脲强得多的除草活性。
本发明优选涉及该式(Ⅰ)化合物,其中;
R1代表氢、氟、氯或溴,或者代表烷基、烷氧基、烷硫基、烷基亚磺酰基、烷基磺酰基、烷氨基或二烷氨基,它们在各自的烷基中各有1到3个碳原子,而且均可任选地被氟、氯、甲氧基或乙氧基取代,
R2代表氢、氟、氯或溴,
R3代表氟、氯或溴,或者代表烷基、烷氧基、烷硫基、烷基亚磺酰基、烷基磺酰基、烷氨基或二烷氨基,它们在各自的烷基中各有1到3个碳原子,而且均可任选地被氟、氯、甲氧基或乙氧基取代,
R4代表氢、氨基、氟、氯、溴或甲酰基,或者代表烷基、烷氧基、烷硫基、烷基亚磺酰基、烷基磺酰基、烷基羰基、烷氧基羰基、烷基羰基氨基、烷氧羰基氨基或烷基磺酰氨基,它们在各自的烷基中各有1到3个碳原子,而且均可任选地被氟、氯、甲氧基或乙氧基取代,
R5代表氢,或者代表有1到6个碳原子的烷基,它可任选地被氟、氯、溴C1-C3烷氧基、C1-C3烷硫基、C1-C3烷基亚磺酰基或C1-C3烷基磺酰基取代,或者代表环烷基、环烷基-C1-C3烷基、环烯基或环烯基-C1-C3烷基,它们在环烷基或环烯基中有4到6个碳原子,而且均可任选地被氟、氯、溴和/或C1-C3烷基取代,或者代表苯基或苯基-C1-C3烷基,它们均可任选地被氟、氯、溴C1-C3烷基或C1-C3卤代烷基取代,或者代表杂环基或杂环基-C1-C3烷基,各有3到5个碳原子和1到3个氮原子和/或一个氧或硫原子,而且均可任选地被氟、氯、溴、C1-C3烷基或C1-C3卤代烷基取代。
本发明还优选地涉及式该(Ⅰ)化合物的钠盐、钾盐、镁盐、钙盐、铵盐、C1-C4烷基-铵盐、二-(C1-C4烷基)-铵盐,三-(C1-C4-烷基)-铵盐、C5或C6-环烷基-铵盐和二(C1-C2烷基)-苄基-铵盐,其中R1、R2、R3、R4和R5具有上面给出的优选含义。
本发明特别涉及该式(Ⅰ)化合物,其中:
R1代表氢、氯、甲基、乙基、三氟甲基、甲氧基、乙氧基、二氟甲氧基、甲硫基、乙硫基、甲氨基、乙氨基或二甲氨基,
R2代表氢,
R3代表氯、甲基、乙基、三氟甲基、甲氧基、乙氧基、二氟甲氧基、甲硫基、乙硫基、甲氨基、乙氨基或二甲氨基,
R4代表氢、氨基、氟、氯、溴、甲基、三氟甲基、甲氧基、甲硫基、甲基亚磺酰基、甲基磺酰基、乙酰基或甲氧羰基,以及
R5代表氢或代表可任选地被氟和/或氯取代的甲基,乙基,正或异丙基,正、异或仲丁基,或者正、异或仲戊基;或者代表甲氧甲基、甲氧乙基、乙氧甲基、乙氧乙基、甲硫基甲基、甲硫基乙基、乙硫基甲基、乙硫基乙基、甲基亚磺酰甲基、乙基亚磺酰甲基、甲基磺酰甲基或乙基磺酰甲基;或者代表可任选地被氟、氯和/或甲基取代的环丁基、环丁基甲基、环戊基、环戊基甲基、环戊烯基甲基、环己基、环己烯基甲基、苯基、苄基、苯乙基、呋喃基、呋喃甲基、噻吩基、噻吩甲基、四氢呋喃基或四氢呋喃甲基。
根据本发明特别优选的一组本发明化合物由下述的通式(Ⅰa)化合物构成,其中基团R1、R2、R3、R4和R5具有以上给出的特别优选的含义。
上述的各基团的一般定义,或者已给出优选范围的各基团的定义,适用于该式(Ⅰ)的最终产物,同样也适用于各种情形里制备所需的起始物或中间体。各基团的这些定义可以彼此组合,也就是说,可以在列出的优选范围之间组合。
在各基团的定义中提到的烃基,例如烷基,以及与杂原子结合的烷基(例如在烷氧基、烷硫基或烷氨基中),即使没有特地说明,也都是直链或支链的。
卤素一般代表氟、氯、溴或碘,优选氟、氯或溴,特别是氟或氯。
例如,如果用4-氯-6-甲氧基-2-氨基-嘧啶、异氰酸氯磺酰酯和2-丙酰-苯胺作为起始物,可以用以下反应式概括表示本发明方法的反应过程:
在根据本发明方法中作为起始物使用的该式(Ⅱ)氨基嘧啶是用于合成的已知化学物,其中有一些是市售商品。
所需要的另一种起始物式(Ⅸ)芳基胺也是用于合成的已知化学物,它们有一些是市售商品(关于合成,参见EP-A 325 247;J.Org,Chem.44(1979),578-586以及制备实施例)。
根据本发明的制备该式(Ⅰ)新化合物的方法优选用稀释剂进行。合适的稀释剂事实上包括所有的惰性有机溶剂。优选的稀释剂包括可任意卤化的脂族和芳族烃类,例如戊烷、己烷、庚烷、环己烷、石油醚、汽油、粗汽油、苯、甲苯、二甲苯、二氯甲烷、氯化乙烯、氯仿、四氯化碳氯苯和邻二氯苯;醚类,例如乙醚和二丁醚、乙二醇二甲醚和二乙二醇二甲醚、四氢呋喃和二噁烷;酮类,例如丙酮、甲乙酮、甲基异丙基酮和甲基异丁基酮;酯类,例如乙酸甲酯和乙酸乙酯;腈类,例如乙腈和丙腈;酰类,例如二甲基甲酰胺、二甲基乙酰胺和N-甲基吡咯烷酮,还包括二甲基亚砜、四亚甲基砜和六甲基磷酰三胺。
可以在本发明使用的酸性接受体是通常可用于这类反应的所有酸结合剂。优选适用的是碱金属氢氧化物,例如氢氧化钠和氢氧化钾;碱土金属氢氧化物,例如氢氧化钙;碱金属碳酸盐和碱金属醇盐,例如碳酸钠和碳酸钾、叔丁醇钠和叔丁醇钾;还有脂族、芳族或杂环胺类,例如,三乙胺、三甲胺、二甲基苯胺、二甲基苄胺、吡啶、1,5-二氮杂二环[4,3,0]-壬-5-烯(DBN)、1,8-二氮杂二环-[5,4,0]、十一碳-7-烯(DBU)和1,4-二氮杂二环[2,2,2]-辛烷(DABCO)。
在进行本发明的方法时,反应温度可以在很大的范围内变化。一般来说,此方法在-30℃和+80℃之间的温度下进行,优选的温度为-10℃和+60℃。
根据本发明的方法通常在大气压下进行。但是,也可以在高压或低压下进行。
为了进行本发明的方法,各种情形里需要的起始物通常按大约等摩尔数量使用。但是,在每种情形里也可以使两种组分之一大量过剩。一般来说,反应是在合适的稀释剂中于酸性接受体存在下进行,该反应混合物在各种情形里要求的温度下搅拌几小时。根据本发明的方法中的后期处理在每种情形里都用常用方法进行(参见制备实施例)。
如果合适,可以用本发明的通式(Ⅰ)化合物制成盐。这些盐是用常规的成盐方法以简单的方式制得的,例如,将该式(Ⅰ)化合物溶解或分散在合适的溶剂中(例如,二氯甲烷、丙酮、叔丁基甲醚或甲苯),加入合适的碱。盐可以随后用浓缩或抽气过滤的方法分离出来。如果合适,在长时间搅拌之后分离。
本发明的活性化合物可以用于例如以下植物:
以下各属双子叶杂草:欧白芥属、独行菜属、拉拉藤属、繁缕属、母菊属、春黄菊属、牛膝菊属、藜属、荨麻属、千里光属、苋属、马齿苋属、苍耳属、旋花属、番薯属、蓼属、田菁属、豚草属、蓟属、飞廉属、苦苣菜属、茄属、蔊菜属、节节菜属、母草属、野芝麻属、婆婆纳属、苘麻属、刺酸模属、曼陀罗属、堇菜属、鼬瓣花属、罂粟属、矢车菊属、车轴草属、毛茛属和蒲公英属。
以下各属双子叶栽培作物:
棉属、大豆属、甜菜属、胡萝卜属、菜豆属、豌豆属、茄属、亚麻属、番薯属、野豌豆属、烟草属、番茄属、花生属、芸苔属、莴苣属、黄瓜属和南瓜属。
以下各属的单子叶杂草:稗属、狗尾草属、黍属、马唐属、梯牧草属、早熟禾属、羊茅属、蟋蟀草属、臂形草属、黑麦草属、雀麦属、燕麦属、莎草属、高梁属、冰草属、狗牙根属、雨久花属、飘拂草属、慈姑属、荸荠属、蔗草属、雀稗属、鸭嘴草属、尖瓣花属、龙爪茅属、剪股颖属、看麦娘属和风草属。
以下各属的单子叶栽培作物:稻属、玉蜀黍属、小麦属、大麦属、燕麦属、黑麦属、高梁属、黍属、甘蔗属、凤梨属、天门冬属和葱属。
然而,根据本发明的活性化合物的用途绝不限于以上各属,而是以同样的方式也扩展到其它植物。
这类化合物,按照使用浓度的不同,适合于清除工业场地、铁路轨道、有树或无树的小路和广场的所有杂草。同样,该化合物也可用于清除多年生栽培作物(例如人造林、观赏林、果园、葡萄园、柑桔园、坚果林、香蕉林、咖啡园、茶园、橡胶园、油棕榈林、可可林、浆果园和啤酒花藤栽培园)中的杂草,以及林间空地、草皮和牧场中的杂草。和选择性地清除一年生栽培作物中的杂草。
根据本发明的式(Ⅰ)化合物特别适合于用出土前和出土后施用的方法选择性地清除单子叶栽培作物中的单子叶和双子叶杂草。
该活性化合物可以转化成常用的制剂,例如溶液、乳状液、可润湿的粉末、悬浮液、粉剂、喷撒剂、糊剂、可溶性粉末、粒剂、悬浮液-乳状液浓缩物、浸渍了活性化合物的天然和合成物质,以及用聚合物物质制成的细小胶囊。
这些制剂用已知方式制备,例如将活性化合物与增量剂混合,增量剂是液体溶剂和/或固体载体,可以任选地使用表面活性剂,也就是乳化剂和/或分散剂和/或起泡剂。
在使用水作为增量剂的情形,也可以使用有机溶剂作为辅助溶剂。合适的液体溶剂主要有:芳族化合物,例如二甲苯、甲苯或烷基萘;氯化的芳族化合物和氯化的脂族烃,例如氯苯、氯乙烯或二氯乙烯;脂族烃,例如环己烷或链烷烃,如石油级分、矿物油和植物油;醇类,例如丁醇或乙二醇以及它们的醚和酯;酮类,例如丙酮、甲乙酮、甲基异丁基酮或环己酮;强极性溶剂,例如二甲基甲酰胺和二甲基亚砜。以及水。
合适的固体载体的实例有:铵盐和磨细的天然矿物(例如高岭土、粘土、滑石、白垩、石英、绿坡缕石、濛脱土或硅藻土)以及磨细的合成矿物(例如高度分散的二氧化硅、氧化铝和硅酸盐);适合作为颗粒剂的固体载体有:粉碎并分级过的天然岩石(例如方解石、大理石、浮石、海泡石和白云石)和合成的无机和有机粉的颗粒,以及有机材料颗粒(如锯末、椰壳、玉米芯和烟草杆);适合作为乳化剂和/或起泡剂的有:例如非离子型和阴离子型表面活性剂,如聚氧乙烯脂肪酸酯、聚氧乙烯脂肪醇醚(如烷基芳基聚乙二醇醚)、烷基磺酸盐、烷基硫酸盐、芳基磺酸盐及蛋白水解产物;适合作为分散剂的有:例如木质素亚硫酸盐废液和甲基纤维素。
在制剂中可以加入粘合剂,例如羧甲基纤维素和粉末、颗粒、或胶乳状的天然和合成聚合物(如阿拉伯树胶、聚乙烯醇和聚乙酸乙烯酯),以及天然磷脂(如脑磷脂和卵磷脂)和合成磷脂。其它的粘合剂可以是矿物油和植物油。
可以使用着色剂,例如无机颜料(如氧化铁、氧化钛和普鲁士蓝)和有机染料(如茜素染料、偶氮染料和金属酞菁染料)以及微量的营养素(如铁、锰、硼、铜、钴、钼和锌的盐)。
制剂中一般含有0.1至95%(重量)、优选0.5至90%(重量)的活性化合物。
为清除杂草,也可以将本发明的活性化合物(原料或制剂形式)与已知的除草剂以混合物形式使用(可以是成品制剂或桶装混合物)。
适合与本发明的化合物混合使用的除草剂是已知的除草剂,例如N-酰苯胺类(如diflufenican和敌稗);芳基羧酸类(如二氯吡啶甲酸、麦草畏和毒莠定);芳氧基链烷酸类(如2,4-滴、2,4-滴丁酸、2,4-滴丙酸、fluroxypyr、2甲4氯、2甲4氯丙酸和定草酯);烷氧苯氧基链烷酸酯类(如氯甲草、fenoxaprop-ethyl、fluazifop-butyl、haloxyfop-methyl和quizalofop-ethyl);连氮酮类(如chloridazon和达草灭);氨基甲酸酯类(如氯苯胺灵、异苯敌草、苯敌草和苯胺灵);乙酰氯苯胺类(如杂草锁、乙基乙草安、丁草锁、metazachlor、丙草安、pretilachlor和毒草安);二硝基苯胺类(如黄草消、胺硝草和氟乐灵);二苯醚类(如氟锁草醚、治草醚、fluoroglycofen、fomesafen、halosafen、lactofen和乙氧氟甲氧醚);脲类(如绿麦隆、敌草隆、伏草隆、异丙隆、利谷隆和噻唑隆);羟胺类(如枯杀达、Clethodim、Cycloxydim、sethoxydim和tralkoxydim);咪唑啉酮类(如imazethapyr、imazamethabenz、imazapyr和imazaquin);腈类(如溴苯腈、敌草腈和碘草腈);氧乙酰胺类(如mefenacet);磺酰脲类(如amidosufuron、bensulfuron-methyl、chlorimuron-ethyl、chlorsulfuron、cinosulfuron、metsulfuron-methyl,nicosulfuron,primisulfuron,pyrazosulfuron-ethyl、thifensulfuron-methyl、triasulfuron和tribenuron-methyl),硫代氨基甲酸酯类(如苏达灭、草灭特、燕麦敌、扑草灭、esprocarb、草达灭、prosulfocarb、杀草丹和野麦畏);三嗪类(如阿特拉津、草净津、西玛津、西草净、去草净和特丁津);三嗪农类(如六嗪农、甲苯嗪和赛克津);以及其它类(如氨三唑、benfuresate、噻草平、Cinmethylin、clomazone、clopyralid、苯敌快、dithiopyr、灭草呋喃、氟氯酮、glufosinate、草甘膦、isoxaben、达草止、quinchlorac、quinmerac、sulphosate和tridiphane)。
也可以与其它的已知活性化合物(例如杀真菌剂、杀虫剂、杀螨剂、杀线虫剂、驱鸟剂、植物营养剂和土壤结构改良剂等)混合使用。
该活性化合物可以以原料形式、制剂形式或由其配制的使用形式使用,例如配好待用的溶液、悬浮液、乳状液、粉剂、糊剂和颗粒剂。它们以惯用方式使用,例如浇灌、喷洒、喷雾或撒布。
本发明的该活性化合物可以在植物出土前或出土后使用,它们也可以在播种前掺到土壤中。
该活性化合物的用量可以很大范围内变化。这主要取决于所要求的效果的本质。一般来说,用量为每公顷地面10g到10kg,优选50g到5kg活性化合物。
由以下实施例可以看出本发明该活性化合物的制备和用途。
制备实施例
实施例1
在-5℃和搅拌下将4.2g(33mmol)2-氨基-4-甲氧基-6-甲基嘧啶加到4.3g(30mmol)异氰酸氯磺酰酯和50ml二氯甲烷的混合物中。将该混合物在0℃下搅拌30分钟。
然后加入4.7g(30mmol)2-氨基-苯基乙基酮、3.5g(35mmol)三乙胺和50ml二氯甲烷,在20℃下继续搅拌此反应混合物18小时。
随后用水和10%的盐酸洗产物,用硫酸钠干燥、过滤。
将滤液减压浓缩,残余物用乙醇溶解结晶,抽气过滤分离出产物。
得到6.9克(理论值的58.5%)的N-(4-甲氧基-6-甲基-嘧啶-2-基)-N′-(2-丙酰基-苯氨基磺酰)脲,熔点为126℃。
可以与实施例1类似地胺着本发明制备方法的一般说明制备的式(Ⅰ)化合物的其它实例列在下面的表1中。
表1:式(Ⅰ)化合物的实例
实施例 R1R2R3位置 R5
编号 R4熔点(℃)
2 OCH3H OCH3H C2H5184
3 OCH3H OCH3H CH3145
4 CH3H OCH3H CH3172
5 Cl H OCH3H CH3158
6 CH3H CH3H CH3171
7 H H CH3H CH3171
8 CH3H CH3H C2H5172
9 Cl H OCH3H C2H5152
10 OCH3H OCH3(6-)Cl C2H5162
11 OCH3H CH3(6-)Cl C2H5157
12 OCH3H OCH3(5-)Cl CH3172
13 OCH3H OCH3(5-)Cl CH(CH3)2166
14 CH3H OCH3H CH(CH3)2149
15 OCH3H OCH3(6-)F CH3
16 OCH3H OCH3(6-)CH3CH3184
17 OCH3H OCH3(6-)Cl CH3174
18 OCH3H OCH3(6-)OCH3CH3
表1:(续)
实施例 R1R2R3位置 R5
编号 R4熔点(℃)
19 OCH3H OCH3(6-)SCH3CH3162
20 OCH3H OCH3(6-)COOCH3CH3
21 OCH3H OCH3(6-)F C2H5155
22 OCH3H OCH3(6-)CH3C2H5164
23 OCH3H OCH3(6-)OCH3C2H5
24 OCH3H OCH3(6-)SCH3C2H5220
25 OCH3H OCH3(6-)COOCH3C2H5
26 OCH3H OCH3(4-)Cl n-C4H9165
27 OCH3H OCH3(5-)Cl CH(CH3)2160
28 CH3H OCH3(6-)F CH3
29 CH3H OCH3(6-)Cl CH3
30 CH3H OCH3(6-)CH3CH3136
31 CH3H OCH3(6-)OCH3CH3
32 CH3H OCH3(6-)SCH3CH3
33 CH3H OCH3(6-)COOCH3CH3
34 CH3H OCH3(6-)F C2H5161
35 CH3H OCH3(6-)CH3C2H5212
表1:(续)
实施例 R1R2R3位置 R5
编号 R4熔点(℃)
36 CH3H OCH3(6-)OCH3C2H5
37 CH3H OCH3(6-)SCH3C2H5
38 CH3H OCH3(6-)COOCH3C2H5
39 Cl H OCH3(6-)F CH3
40 Cl H OCH3(6-)Cl CH3154
41 Cl H OCH3(6-)CH3CH3145
42 Cl H OCH3(6-)OCH3CH3
43 Cl H OCH3(6-)SCH3CH3
44 Cl H OCH3(6-)COOCH3CH3
45 Cl H OCH3(6-)F C2H5180
46 Cl H OCH3(6-)Cl C2H5184
47 Cl H OCH3(6-)CH3C2H5158
48 Cl H OCH3(6-)OCH3C2H5
49 Cl H OCH3(6-)SCH3C2H5196
50 Cl H OCH3(6-)COOCH3C2H5
51 H H CH3(6-)F CH3
52 H H CH3(6-)Cl CH3
表1:(续)
实施例 R1R2R3位置 R5
编号 R4熔点(℃)
53 H H CH3(6-)CH3CH3
54 H H CH3(6-)OCH3CH3
55 H H CH3(6-)SCH3CH3
56 H H CH3(6-)COOCH3CH3
57 H H CH3H C2H5
58 H H CH3(6-)F C2H5
59 H H CH3(6-)Cl C2H5
60 H H CH3(6-)CH3C2H5
61 H H CH3(6-)OCH3C2H5
62 H H CH3(6-)SCH3C2H5
63 H H CH3(6-)COOCH3C2H5
64 H H OCH3H CH3
65 H H OCH3(6-)F CH3
66 H H OCH3(6-)Cl CH3
67 H H OCH3(6-)CH3CH3
68 H H OCH3(6-)SCH3CH3
69 H H OCH3(6-)OCH3CH3
表1:(续)
实施例 R1R2R3位置 R5
编号 R4熔点(℃)
70 H H OCH3(6-)COOCH3CH3
71 H H OCH3H C2H5
72 H H OCH3(6-)F C2H5
73 H H OCH3(6-)Cl C2H5
74 H H OCH3(6-)OCH3C2H5
75 H H OCH3(6-)SCH3C2H5
76 H H OCH3(6-)CH3C2H5
77 H H OCH3(6-)COOCH3C2H5
78 CH3H CH3(6-)F CH3
79 CH3H CH3(6-)Cl CH3158
80 CH3H CH3(6-)CH3CH3128
81 CH3H CH3(6-)SCH3CH3
82 CH3H CH3(6-)OCH3CH3
83 CH3H CH3(6-)COOCH3CH3
84 CH3H CH3(6-)F C2H5160
85 CH3H CH3(6-)Cl C2H5
86 CH3H CH3(6-)OCH3C2H5
表1:(续)
实施例 R1R2R3位置 R5
编号 R4熔点(℃)
87 CH3H CH3(6-)SCH3C2H5174
88 CH3H CH3(6-)CH3C2H5178
89 CH3H CH3(6-)COOCH3C2H5
90 CF3H CF3H CH3
91 CF3H CF3(6-)F CH3
92 CF3H CF3(6-)Cl CH3
93 CF3H CF3(6-)CH3CH3
94 CF3H CF3(6-)SCH3CH3
95 CF3H CF3(6-)OCH3CH3
96 CF3H CF3(6-)COOCH3CH3
97 CF3H CF3H C2H5
98 CF3H CF3(6-)F C2H5
99 CF3H CF3(6-)Cl C2H5
100 CF3H CF3(6-)OCH3C2H5
101 CF3H CF3(6-)SCH3C2H5
102 CF3H CF3(6-)CH3C2H5
103 CF3H CF3(6-)COOCH3C2H5
表1:(续)
实施例 R1R2R3位置 R5
编号 R4熔点(℃)
104 CF3H OCH3H CH3
105 CF3H OCH3(6-)F CH3
106 CF3H OCH3(6-)Cl CH3
107 CF3H OCH3(6-)CH3CH3
108 CF3H OCH3(6-)SCH3CH3
109 CF3H OCH3(6-)OCH3CH3
110 CF3H OCH3(6-)COOCH3CH3
111 CF3H OCH3H C2H5
112 CF3H OCH3(6-)F C2H5
113 CF3H OCH3(6-)Cl C2H5
114 CF3H OCH3(6-)OCH3C2H5
115 CF3H OCH3(6-)SCH3C2H5
116 CF3H OCH3(6-)CH3C2H5
117 CF3H OCH3(6-)COOCH3C2H5
118 OCHF2H OCHF2H CH3
119 OCHF2H OCHF2(6-)F CH3
120 OCHF2H OCHF2(6-)Cl CH3
表1:(续)
实施例 R1R2R3位置 R5
编号 R4熔点(℃)
121 OCHF2H OCHF2(6-)CH3CH3
122 OCHF2H OCHF2(6-)SCH3CH3
123 OCHF2H OCHF2(6-)OCH3CH3
124 OCHF2H OCHF2(6-)COOCH3CH3
125 OCHF2H OCHF2H C2H5
126 OCHF2H OCHF2(6-)F C2H5
127 OCHF2H OCHF2(6-)Cl C2H5
128 OCHF2H OCHF2(6-)OCH3C2H5
129 OCHF2H OCHF2(6-)SCH3C2H5
130 OCHF2H OCHF2(6-)CH3C2H5
131 OCHF2H OCHF2(6-)COOCH3C2H5
132 OCH3H NHCH3H CH3
133 OCH3H NHCH3(6-)F CH3
134 OCH3H NHCH3(6-)Cl CH3
135 OCH3H NHCH3(6-)CH3CH3
136 OCH3H NHCH3(6-)SCH3CH3
137 OCH3H NHCH3(6-)OCH3CH3
R3位置 R5
R4熔点(℃)
138 OCH3NHCH3(6-)COOCH3CH3
139 OCH3H NHCH3H C2H5
140 OCH3H NHCH3(6-)F C2H5
141 OCH3H NHCH3(6-)Cl C2H5
142 OCH3H NHCH3(6-)OCH3C2H5
143 OCH3H NHCH3(6-)SCH3C2H5
144 OCH3H NHCH3(6-)CH3C2H5
145 OCH3H NHCH3(6-)COOCH3C2H5
146 OC2H5H NHCH3H CH3
147 OC2H5H NHCH3(6-)F CH3
148 OC2H5H NHCH3(6-)Cl CH3
149 OC2H5H NHCH3(6-)CH3CH3
150 OC2H5H NHCH3(6-)SCH3CH3
151 OC2H5H NHCH3(6-)OCH3CH3
152 OC2H5H NHCH3(6-)COOCH3CH3
153 OC2H5H NHCH3H C2H5
154 OC2H5H NHCH3(6-)F C2H5
实施例 R1R2R3位置 R5
编号 R4熔点(℃)
231 OCH3H OCH3(6-)SO2C2H5C3H7-n 125
232 OCH3H OCH3(6-)SCH3C3H7-n 148
233 CH3H OCH3(6-)SCH3C3H7-n 137
234 OCH3H OCH3(6-)SO2CH3C3H7-n 132
235 Cl H OCH3H C3H7-n 129
236 Cl H OCH3(6-)SCH3C3H7-n 139
237 Cl H OCH3(6-)Cl C3H7-n 148
238 CH3H OCH3(6-)Cl C3H7-n 145
239 CH3H OCH3(6-)SC2H5C3H7-n 168
240 CH3H OCH3(6-)F C3H7-n 149
241 Cl H OCH3(6-)F C3H7-n 148
242 OCH3H OCH3(6-)SO2CH3CH3182
243 CH3H OC2H5H CH3180
244 OCH3H OCH3(6-)Br C2H5185
245 CH3H OCH3(6-)Br C2H5169
246 Cl H OCH3(6-)Br C2H5161
247 CH3H CH3(6-)Br C2H5181
表1:(续)
实施例 R1R2R3位置 R5
编号 R4熔点(℃)
248 OCH3H OCH3(6-)Br CH3195
249 CH3H OCH3(6-)Br CH3191
250 OCH3H OCH3(6-)CH3-CH2SCH3148
251 Cl H OCH3(6-)CH3-CH2SCH3102
252 CH3H OCH3(6-)CH3-CH2SCH385
253 Cl H OCH3(6-)CH3-CH2SOCH3112
254 OCH3H OCH3(6-)Br C3H7-n 174
255 Cl H OCH3(6-)Br C3H7-n 152
256 CH3H OCH3(6-)Br C3H7-n 148
257 Cl H OCH3(6-)Br CH3182
258 CH3H CH3(6-)Br CH3177
259 Cl H OC2H5(6-)SCH3CH3150
260 Cl H OC2H5(6-)Cl C2H5174
261 Cl H OC2H5(6-)Cl CH3174
262 Cl H OC2H5H C2H5124
263 Cl H CH3H C2H5161
264 Cl H CH3H CH3196
表1:(续)
实施例 R1R2R3位置 R5
编号 R4熔点(℃)
265 Cl H CH3(6-)CH3CH3201
266 Cl H CH3(6-)SCH3CH3158
267 Cl H CH3(6-)SCH3C2H5140
268 OCH3H OCH3H -CH2Cl 244
269 Cl H OCH3H -CH2Cl 194
270 CH3H OCH3H -CH2Cl 177
271 CH3H CH3H -CH2Cl 156
272 Cl H CH3H -CH2Cl 140
273 Cl H OC2H5H -CH2Cl 112
274 CH3H OC2H5H -CH2Cl 175
275 OCH3H OCH3(6-)CH3-CH2Cl 178
276 Cl H OCH3(6-)CH3-CH2Cl 128
277 CH3H OCH3(6-)CH3-CH2Cl 153
278 CH3H CH3(6-)CH3-CH2Cl 164
279 Cl H CH3(6-)CH3-CH2Cl 171
280 Cl H OC2H5(6-)CH3-CH2Cl 136
281 CH3H OC2H5(6-)CH3-CH2Cl 155
表1:(续)
实施例 R1R2R3位置 R5
编号 R4熔点(℃)
282 OCH3H OCH3(6-)Cl -CH2Cl 155
283 Cl H OCH3(6-)F -CH2Cl 158
284 OCH3H OCH3(6-)Br -CH2Cl 155
285 Cl H OCH3(6-)Br -CH2Cl 105
式(Ⅳ)的起始物
实施例(Ⅳ-1)
将100ml(0.1mol)三氯化硼和100ml 1,2-二氯乙烷的混合物冷却到0℃。在此温度在15分钟内于搅拌下逐滴加入12.3g(0.1mol)4-甲氧基苯胺。然后逐滴加入10.4g(0.15mol)异丁腈在100ml 1,2-二氯乙烷中的溶液,在将该混合物搅拌5分钟后,在0℃向混合物中分批加入14.7g(0.11mol)三氯化铝。随后将该反应混合物在80℃搅拌5小时,接着用冰冷却,逐滴加入300ml水。然后分离出有机相,水相用二氯甲烷再萃取三次。将合并的有机相在硫酸钠上干燥,过滤,将滤液浓缩。残余物用柱状色谱法分离(硅胶;己烷/乙酸乙酯,体积比4∶1)。
得到5.3g(理论值的27.5%)4-甲氧基-2-异丁酰苯胺。
实施例(Ⅳ-2)
将10.9g(72mmol)2-氰基-4-氯-苯胺溶在30ml乙醚中,将该混合物冷却至0℃。在这人温度加入氯化环戊基镁在乙醚中的2mol/l溶液,将该反应混合物在20℃时再搅拌4.5小时。在将该混合物冷却到0℃之后,逐滴加入150ml 10%的盐酸,将该混合物在20℃搅拌1小时。在将该混合物再次冷却到0℃之后,向该混合物加入25g氢氧化钠,分离出有机相,用乙醚再萃取水相三次,合并的有机相在硫酸钠上干燥并浓缩之。
残余物用柱状色谱法分离(硅胶;己烷/乙酸乙酯,体积比4∶1)。
得到11.9g(理论值的74%)4-氯-2-环戊酰苯胺,熔点73℃。
可以类似于实施例(Ⅳ-1)或(Ⅳ-2)制得的其它的式(Ⅳ)化合物列在下面的表2中。
应用实施例
在应用实施例中,使用下面的化合物(A)作为对照物:
N-(4,6-二甲氧基-嘧啶-2-基)-N′-(2-环丙基-羰基-苯氨基磺酰)-脲(公开在EP-A463287/美国专利5009699)。
实施例A
出土后试验
溶剂:5重量份丙酮
乳化剂:1重量份烷基芳基聚乙二醇醚
为制备合适的活性化合物制剂,将1重量份的活性化合物与所述数量的溶剂混合,加入所述数量的乳化剂,用水将此浓缩物稀释到所要求的浓缩。
用活性化合物制剂喷洒高5-15cm的试验植物,以便在每单位面积上施加所要求的特定数量的活性化合物。选择喷洒液的浓度,使得所要求的特定数量的活性化合物以每公顷2000升水的方式施用。三周后,与未处理的对照样的发育情况比较,按照损伤%将植物的操作程度分级。
0%=无作用(与未处理的对照样相同)
100%=完全毁坏
在此试验中,与已知化合物(A)相比,制备实施例1和2的化合物显示出强得多的灭草作用,而且作物(例如小麦)有很好的耐受性。
实施例B
溶剂:5重量份丙酮
乳化剂:1重量份烷基芳基聚乙二醇醚
为制备合适的活性化合物制剂,将1重量份的活性化合物与所述数量的溶剂混合,加入所述数量的乳化剂,用水将此浓缩物稀释到所要求的浓度。
将试验植物的种子播在普通土壤中。24小时后用活性化合物制剂浇灌土壤。最好是保持每单位面积的水是恒定。制剂中的活性化合物浓度并不重要,起决定作用的只是单位面积施加的活性化合物数量。三周后,与未处理的对照样的发育情况比较,按照损伤%将损伤程度分级。数字表示:
0%=无作用(与未处理的对照样相同)
100%=完全毁坏
在此试验中,与已知化合物(A)相比,制备实施例1和2的化合物显示出强得多的灭草作用,而且作物(例如小麦)有很好的耐受性。
应当明白,本说明书和权利要求的陈述仅为示例说明而非限制,可以作出各种修改和变动而不偏离本发明的精神和范围。
Claims (9)
1、通式(Ⅰ)的取代的苯氨基磺酰脲类及式(Ⅰ)化合物的盐:
其中
R1代表氢、卤素、或者代表烷基、烷氧基、烷硫基、烷基亚磺酰基、烷基磺酰基、烷氨基或二烷氨基,它们在各自的烷基中各有1到4个碳原子,而且均可任选地被卤素或C1-C3烷氧基取代。
R2代表氢或卤素,
R3代表卤素,或者代表烷基、烷氧基、烷硫基、烷基亚磺酰基、烷基磺酰基、烷氨基或二烷氨基,它们在各自的烷基中各有1至4个碳原子,而且均可任选地被卤素或C1-C3烷氧基取代,
R4代表氢、氨基、卤素或甲酰基,或者代表烷基、烷氧基、烷硫基、烷基亚磺酰基、烷基磺酰基、烷基羰基、烷氧基羰基、烷基羰基氨基、烷氧羰基氨基或烷基磺酰氨基,它们在各自的烷基中各有1到4个碳原子,而且均可任选地被卤素或C1-C3烷氧基取代,
R5代表氢,或者代表有1到8个碳原子的烷基,该烷基可任选地被卤素、C1-C4烷氧基、C1-C4烷硫基、C1-C4烷基亚磺酰基或C1-C4烷基磺酰基取代,或者代表环烷基、环烷基-C1-C4烷基、环烯基或环烯基-C1-C4烷基,它们在环烷基或环烯基中各有4到7个碳原子,而且均可任选地被卤素和/或C1-C4烷基取代,或者代表可任选地被卤素、C1-C4烷基或C1-C4卤代烷基取代的苯基或苯基-C1-C4烷基,或者代表有2到6个碳原子和1到3个氮原子以及/或1个氧或硫原子的杂环基或杂环基-C1-C4烷基,而且可任选地被卤素、C1-C4烷基或C1-C4卤代烷基取代。
2、根据权利要求1的式(Ⅰ)化合物及其盐,其特征在于,在式(Ⅰ)中,
R1代表氢、氟、氯或溴,或者代表烷基、烷氧基、烷硫基、烷基亚磺酰基、烷基磺酰基、烷氨基或二烷氨基,它们在各自的烷基中各有1到3个碳原子,而且均可任选地被氟、氯、甲氧基或乙氧基取代,
R2代表氢、氟、氯或溴,
R3代表氟、氯或溴,或者代表烷基、烷氧基、烷硫基、烷基亚磺酰基、烷基磺酰基、烷氨基或二烷氨基,它们在各自的烷基中各有1到3个碳原子,而且均可任选地被氟、氯、甲氧基或乙氧基取代,
R4代表氢、氨基、氟、氯、溴或甲酰基,或者代表烷基、烷氧基、烷硫基、烷基亚磺酰基、烷基磺酰基、烷基羰基、烷氧羰基、烷基羰基氨基、烷氧羰基氨基或烷基磺酰氨基,它们在各自的烷基中各有1到3个碳原子,而且均可任选地被氟、氯、甲氧基或乙氧基取代,
R5代表氢,或者代表有1到6个碳原子的烷基,它可任选地被氟、氯、溴、C1-C3烷氧基、C1-C3烷硫基、C1-C3烷基亚磺酰基或C1-C3烷基磺酰基取代,或者代表环烷基、环烷基-C1-C3烷基、环烯基或环烯基-C1-C3烷基,它们在环烷基或环烯基中有4到6个碳原子,而且均可任选地被氟、氯、溴和/或C1-C3烷基取代,或者代表苯基或苯基-C1-C3烷基,它们均可任选地被氟、氯、溴、C1-C3烷基或C1-C3卤代烷基取代,或者代表杂环基或杂环基-C1-C3烷基,它们各有3到5个碳原子和1到3个氮原子和/或一个氧或硫原子,而且均可任选地被氟、氯、溴、C1-C3烷基或C1-C3卤代烷基取代。
3、根据权利要求1的式(Ⅰ)化合物及其盐,其特征在于,在式(Ⅰ)中,
R1代表氢、氯、甲基、乙基、三氟甲基、甲氧基、乙氧基、二氟甲氧基、甲硫基、乙硫基、甲氨基、乙氨基或二甲氨基,
R2代表氢,
R3代表氯、甲基、乙基、三氟甲基、甲氧基、乙氧基、二氟甲氧基、甲硫基、乙硫基、甲氨基、乙氨基或二甲氨基,
R4代表氢、氨基、氟、氯、溴、甲基、三氟甲基、甲氧基、甲硫基、甲基亚磺酰基、甲基磺酰基、乙酰基或甲氧羰基,
R5代表氢,或者代表可任选地被氟和/或氯取代的甲基,乙基,正或异丙基,正、异或仲丁基,或者正、异或仲戊基;或者代表甲氧甲基、甲氧乙基、乙氧甲基、乙氧乙基、甲硫基甲基、甲硫基乙基、乙硫基甲基、乙硫基乙基、甲基亚磺酰甲基、乙基亚磺酰甲基、甲基磺酰甲基或乙基磺酰甲基;或者代表均可任选地被氟、氯和/或甲基取代的环丁基、环丁基甲基、环戊基、环戊基甲基、环戊烯基甲基、环己基、环己烯基甲基、苯基、苄基、苯乙基、呋喃基、呋喃甲基、噻吩基、噻吩甲基、四氢呋喃基或四氢呋喃甲基。
4、式(Ⅰa)化合物及其盐
其中R1、R2、R3、R4和R5具有权利要求3中给出的意义。
6、除草组合物,其特征在于,它们含有至少一种根据权利要求1的式(Ⅰ)化合物。
7、使用权利要求1的通式(Ⅰ)化合物消除不想要的杂草生长。
8、消除杂草的方法,其特征在于,使根据权利要求1的通式(Ⅰ)化合物作用在杂草或其环境上。
9、制备除草组合物的方法,其特征在于,将权利要求1的通式(Ⅰ)化合物与增量剂和/或表面活性剂混合。
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
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DEP4337847.1 | 1993-11-05 | ||
DE4337847A DE4337847A1 (de) | 1993-11-05 | 1993-11-05 | Substituierte Phenylaminosulfonylharnstoffe |
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CN1107147A true CN1107147A (zh) | 1995-08-23 |
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CN94118195A Pending CN1107147A (zh) | 1993-11-05 | 1994-11-05 | 取代的苯氨基磺酰脲类除草剂 |
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EP (1) | EP0661276A1 (zh) |
JP (1) | JPH07188184A (zh) |
CN (1) | CN1107147A (zh) |
AU (1) | AU7751394A (zh) |
BR (1) | BR9404345A (zh) |
CA (1) | CA2134915A1 (zh) |
DE (1) | DE4337847A1 (zh) |
RU (1) | RU94040154A (zh) |
ZA (1) | ZA948720B (zh) |
Cited By (1)
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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 |
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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 |
US5847140A (en) * | 1995-06-06 | 1998-12-08 | American Cyanamid Company | Intermediates for the manufacture of herbicidal 1-{ 2-(cyclopropylcarbonyl) Phenyl! Sulfamoyl}-3-(4,6-dialkoxy-2-pyrimidinyl) urea compounds |
IT1275813B1 (it) * | 1995-10-27 | 1997-10-17 | Isagro Ricerca Srl | Amminosolfoniluree |
US6127576A (en) * | 1996-12-20 | 2000-10-03 | American Cyanamid Company | Aminophenyl ketone derivatives and a method for the preparation thereof |
US5856576A (en) * | 1997-02-04 | 1999-01-05 | American Cyanamid Company | Aryne intermediates and a process for the preparation thereof |
DE19707580A1 (de) * | 1997-02-26 | 1998-08-27 | Bayer Ag | Phenylaminosulfonylharnstoffderivate |
US7279576B2 (en) | 2002-12-31 | 2007-10-09 | Deciphera Pharmaceuticals, Llc | Anti-cancer medicaments |
US7202257B2 (en) | 2003-12-24 | 2007-04-10 | Deciphera Pharmaceuticals, Llc | Anti-inflammatory medicaments |
US7144911B2 (en) | 2002-12-31 | 2006-12-05 | Deciphera Pharmaceuticals Llc | Anti-inflammatory medicaments |
EP1835934A4 (en) | 2004-12-23 | 2010-07-28 | Deciphera Pharmaceuticals Llc | ENZYME MODULATORS AND TREATMENTS |
US8188113B2 (en) | 2006-09-14 | 2012-05-29 | Deciphera Pharmaceuticals, Inc. | Dihydropyridopyrimidinyl, dihydronaphthyidinyl and related compounds useful as kinase inhibitors for the treatment of proliferative diseases |
US7790756B2 (en) | 2006-10-11 | 2010-09-07 | Deciphera Pharmaceuticals, Llc | Kinase inhibitors useful for the treatment of myleoproliferative diseases and other proliferative diseases |
BRPI0807717A2 (pt) | 2007-04-20 | 2014-05-20 | Deciphera Pharmaceuticals Llc | Inibidores de quinase úteis para o tratamento de doenças mieloproliferativas e outras doenças proliferativas. |
EP2365752B1 (en) | 2008-10-29 | 2014-09-24 | Deciphera Pharmaceuticals, Llc | Cyclopropane amides and analogs exhibiting anti-cancer and anti-proliferative activities |
US8461179B1 (en) | 2012-06-07 | 2013-06-11 | Deciphera Pharmaceuticals, Llc | Dihydronaphthyridines and related compounds useful as kinase inhibitors for the treatment of proliferative diseases |
DE102015104306B4 (de) * | 2015-03-23 | 2018-05-03 | Papierfabrik August Koehler Se | Wärmeempfindliches Aufzeichnungsmaterial |
KR20200115607A (ko) | 2018-01-31 | 2020-10-07 | 데시페라 파마슈티칼스, 엘엘씨. | 위장관 기질 종양의 치료를 위한 병용 요법 |
KR20220045189A (ko) | 2019-08-12 | 2022-04-12 | 데시페라 파마슈티칼스, 엘엘씨. | 위장관 기질 종양을 치료하는 방법 |
WO2021030405A1 (en) | 2019-08-12 | 2021-02-18 | Deciphera Pharmaceuticals, Llc | Ripretinib for treating gastrointestinal stromal tumors |
KR20220123057A (ko) | 2019-12-30 | 2022-09-05 | 데시페라 파마슈티칼스, 엘엘씨. | 비정질 키나아제 억제제 제형 및 이의 사용 방법 |
IL293864A (en) | 2019-12-30 | 2022-08-01 | Deciphera Pharmaceuticals Llc | Preparations of 1-(4-bromo-5-(1-ethyl-7-(methylamino)-2-oxo-1,2-dihydro-1,6-naphthyridin-3-yl)-2-fluorophenyl)-3- phenylurea |
US11779572B1 (en) | 2022-09-02 | 2023-10-10 | Deciphera Pharmaceuticals, Llc | Methods of treating gastrointestinal stromal tumors |
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US4191553A (en) * | 1978-03-02 | 1980-03-04 | E. I. Du Pont De Nemours And Company | Herbicidal sulfamates |
DE3243533A1 (de) * | 1981-12-03 | 1983-06-09 | Sandoz-Patent-GmbH, 7850 Lörrach | Sulfonamide als herbizide |
CH649081A5 (de) * | 1982-01-12 | 1985-04-30 | Ciba Geigy Ag | Triaza-verbindungen. |
US4559081A (en) * | 1984-12-03 | 1985-12-17 | Ppg Industries, Inc. | Sulfamoyl urea derivatives |
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DE3816704A1 (de) * | 1988-05-17 | 1989-11-30 | Hoechst Ag | Heterocyclische 2-alkoxyphenoxysulfonylharnstoffe und ihre verwendung als herbizide oder pflanzenwachstumsregulatoren |
US5009699A (en) * | 1990-06-22 | 1991-04-23 | American Cyanamid Company | 1-{[O-(cyclopropylcarbonyl)phenyl]sulfamoyl}-3-(4,6-dimethoxy-2-pyrimidinyl)urea herbicidal composition and use |
US5280007A (en) * | 1991-12-18 | 1994-01-18 | American Cyanamid Company | Method for safening rice against the phytotoxic effects of a sulfamoyl urea herbicide |
-
1993
- 1993-11-05 DE DE4337847A patent/DE4337847A1/de not_active Withdrawn
-
1994
- 1994-10-24 EP EP94116723A patent/EP0661276A1/de not_active Withdrawn
- 1994-10-27 AU AU77513/94A patent/AU7751394A/en not_active Abandoned
- 1994-11-02 CA CA002134915A patent/CA2134915A1/en not_active Abandoned
- 1994-11-04 ZA ZA948720A patent/ZA948720B/xx unknown
- 1994-11-04 BR BR9404345A patent/BR9404345A/pt not_active Application Discontinuation
- 1994-11-04 RU RU94040154/04A patent/RU94040154A/ru unknown
- 1994-11-04 JP JP6295906A patent/JPH07188184A/ja active Pending
- 1994-11-05 CN CN94118195A patent/CN1107147A/zh active Pending
Cited By (1)
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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 |
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RU94040154A (ru) | 1996-10-10 |
EP0661276A1 (de) | 1995-07-05 |
CA2134915A1 (en) | 1995-05-06 |
AU7751394A (en) | 1995-05-18 |
DE4337847A1 (de) | 1995-05-11 |
ZA948720B (en) | 1995-07-03 |
JPH07188184A (ja) | 1995-07-25 |
BR9404345A (pt) | 1995-07-04 |
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