CN1049439A - 棉花脱落剂 - Google Patents
棉花脱落剂 Download PDFInfo
- Publication number
- CN1049439A CN1049439A CN90106897A CN90106897A CN1049439A CN 1049439 A CN1049439 A CN 1049439A CN 90106897 A CN90106897 A CN 90106897A CN 90106897 A CN90106897 A CN 90106897A CN 1049439 A CN1049439 A CN 1049439A
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- CN
- China
- Prior art keywords
- methyl
- alkyl
- chlorine
- hydrogen
- disleave
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Pending
Links
- 229920000742 Cotton Polymers 0.000 title claims abstract description 36
- 239000000460 chlorine Substances 0.000 claims abstract description 42
- -1 alkaline earth metal salt Chemical class 0.000 claims abstract description 36
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims abstract description 28
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims abstract description 25
- GHDLZGOOOLEJKI-UHFFFAOYSA-N benzenesulfonylurea Chemical compound NC(=O)NS(=O)(=O)C1=CC=CC=C1 GHDLZGOOOLEJKI-UHFFFAOYSA-N 0.000 claims abstract description 25
- 229910052801 chlorine Inorganic materials 0.000 claims abstract description 25
- 239000001257 hydrogen Substances 0.000 claims abstract description 25
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 25
- 150000002431 hydrogen Chemical class 0.000 claims abstract description 20
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims abstract description 14
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims abstract description 14
- 229910052794 bromium Inorganic materials 0.000 claims abstract description 14
- 229910052731 fluorine Inorganic materials 0.000 claims abstract description 12
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims abstract description 12
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims abstract description 11
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims abstract description 11
- 239000011737 fluorine Substances 0.000 claims abstract description 11
- 229910052736 halogen Inorganic materials 0.000 claims abstract description 10
- 229910052783 alkali metal Inorganic materials 0.000 claims abstract description 9
- 150000001340 alkali metals Chemical class 0.000 claims abstract description 8
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 6
- 150000002367 halogens Chemical class 0.000 claims abstract description 6
- 125000005843 halogen group Chemical group 0.000 claims abstract description 3
- 239000003814 drug Substances 0.000 claims description 22
- 238000000034 method Methods 0.000 claims description 19
- XKJCHHZQLQNZHY-UHFFFAOYSA-N phthalimide Chemical compound C1=CC=C2C(=O)NC(=O)C2=C1 XKJCHHZQLQNZHY-UHFFFAOYSA-N 0.000 claims description 13
- 229910052757 nitrogen Inorganic materials 0.000 claims description 10
- 239000002585 base Substances 0.000 claims description 8
- 239000000654 additive Substances 0.000 claims description 7
- 150000001447 alkali salts Chemical class 0.000 claims description 7
- 159000000000 sodium salts Chemical class 0.000 claims description 7
- 229910052760 oxygen Inorganic materials 0.000 claims description 6
- 239000001301 oxygen Substances 0.000 claims description 6
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 5
- 239000005864 Sulphur Chemical group 0.000 claims description 5
- 230000035613 defoliation Effects 0.000 claims description 5
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 4
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 4
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 4
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 4
- 230000000996 additive effect Effects 0.000 claims description 3
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims description 2
- 125000004200 2-methoxyethyl group Chemical group [H]C([H])([H])OC([H])([H])C([H])([H])* 0.000 claims description 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims 4
- KHHDRKQLFDZVEC-UHFFFAOYSA-N [S].NC(=O)N.C1=CC=CC=C1 Chemical compound [S].NC(=O)N.C1=CC=CC=C1 KHHDRKQLFDZVEC-UHFFFAOYSA-N 0.000 claims 1
- 229910052784 alkaline earth metal Inorganic materials 0.000 abstract description 2
- 150000001875 compounds Chemical class 0.000 description 29
- 150000003839 salts Chemical class 0.000 description 26
- 239000000203 mixture Substances 0.000 description 22
- 230000000694 effects Effects 0.000 description 18
- 241000219146 Gossypium Species 0.000 description 16
- 240000002024 Gossypium herbaceum Species 0.000 description 14
- 235000004341 Gossypium herbaceum Nutrition 0.000 description 14
- 150000002148 esters Chemical class 0.000 description 13
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 11
- 239000004480 active ingredient Substances 0.000 description 11
- 239000004202 carbamide Substances 0.000 description 10
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- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 9
- 150000001408 amides Chemical class 0.000 description 9
- 239000002872 contrast media Substances 0.000 description 9
- 239000007788 liquid Substances 0.000 description 9
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 9
- 238000006243 chemical reaction Methods 0.000 description 8
- 239000003795 chemical substances by application Substances 0.000 description 7
- 239000002837 defoliant Substances 0.000 description 7
- 238000002360 preparation method Methods 0.000 description 7
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 description 7
- 241000196324 Embryophyta Species 0.000 description 6
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 6
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- 239000002253 acid Substances 0.000 description 6
- 238000011010 flushing procedure Methods 0.000 description 6
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 5
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 5
- 230000012010 growth Effects 0.000 description 5
- 150000002466 imines Chemical class 0.000 description 5
- RBTFLBJQWSIAGL-UHFFFAOYSA-N C(=O)OC1=CC=CC=C1.N Chemical compound C(=O)OC1=CC=CC=C1.N RBTFLBJQWSIAGL-UHFFFAOYSA-N 0.000 description 4
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 4
- 125000004453 alkoxycarbonyl group Chemical group 0.000 description 4
- 150000001412 amines Chemical class 0.000 description 4
- 239000004359 castor oil Substances 0.000 description 4
- 235000019438 castor oil Nutrition 0.000 description 4
- 239000007859 condensation product Substances 0.000 description 4
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 4
- 239000000839 emulsion Substances 0.000 description 4
- ZEMPKEQAKRGZGQ-XOQCFJPHSA-N glycerol triricinoleate Natural products CCCCCC[C@@H](O)CC=CCCCCCCCC(=O)OC[C@@H](COC(=O)CCCCCCCC=CC[C@@H](O)CCCCCC)OC(=O)CCCCCCCC=CC[C@H](O)CCCCCC ZEMPKEQAKRGZGQ-XOQCFJPHSA-N 0.000 description 4
- 238000000227 grinding Methods 0.000 description 4
- 239000006072 paste Substances 0.000 description 4
- 230000001105 regulatory effect Effects 0.000 description 4
- 239000000741 silica gel Substances 0.000 description 4
- 229910002027 silica gel Inorganic materials 0.000 description 4
- 239000002904 solvent Substances 0.000 description 4
- 239000007921 spray Substances 0.000 description 4
- 239000005995 Aluminium silicate Substances 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 3
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- 229920002257 Plurafac® Polymers 0.000 description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- XBDQKXXYIPTUBI-UHFFFAOYSA-N Propionic acid Substances CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- LSNNMFCWUKXFEE-UHFFFAOYSA-N Sulfurous acid Chemical compound OS(O)=O LSNNMFCWUKXFEE-UHFFFAOYSA-N 0.000 description 3
- 239000003513 alkali Substances 0.000 description 3
- 235000012211 aluminium silicate Nutrition 0.000 description 3
- 239000007864 aqueous solution Substances 0.000 description 3
- 238000009835 boiling Methods 0.000 description 3
- 239000002274 desiccant Substances 0.000 description 3
- 238000009472 formulation Methods 0.000 description 3
- NLYAJNPCOHFWQQ-UHFFFAOYSA-N kaolin Chemical compound O.O.O=[Al]O[Si](=O)O[Si](=O)O[Al]=O NLYAJNPCOHFWQQ-UHFFFAOYSA-N 0.000 description 3
- 150000002576 ketones Chemical class 0.000 description 3
- 239000000463 material Substances 0.000 description 3
- 150000002790 naphthalenes Chemical class 0.000 description 3
- 230000000422 nocturnal effect Effects 0.000 description 3
- 239000012188 paraffin wax Substances 0.000 description 3
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 3
- 239000000377 silicon dioxide Substances 0.000 description 3
- 239000007787 solid Substances 0.000 description 3
- 239000000243 solution Substances 0.000 description 3
- 239000002699 waste material Substances 0.000 description 3
- 239000000080 wetting agent Substances 0.000 description 3
- UWNADWZGEHDQAB-UHFFFAOYSA-N 2,5-dimethylhexane Chemical group CC(C)CCC(C)C UWNADWZGEHDQAB-UHFFFAOYSA-N 0.000 description 2
- ANHAEBWRQNIPEV-UHFFFAOYSA-N 2-chloroethyl dihydrogen phosphate Chemical compound OP(O)(=O)OCCCl ANHAEBWRQNIPEV-UHFFFAOYSA-N 0.000 description 2
- 125000001340 2-chloroethyl group Chemical group [H]C([H])(Cl)C([H])([H])* 0.000 description 2
- DUIOKRXOKLLURE-UHFFFAOYSA-N 2-octylphenol Chemical compound CCCCCCCCC1=CC=CC=C1O DUIOKRXOKLLURE-UHFFFAOYSA-N 0.000 description 2
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- GUVLYNGULCJVDO-UHFFFAOYSA-N EPTC Chemical compound CCCN(CCC)C(=O)SCC GUVLYNGULCJVDO-UHFFFAOYSA-N 0.000 description 2
- CPLXHLVBOLITMK-UHFFFAOYSA-N Magnesium oxide Chemical compound [Mg]=O CPLXHLVBOLITMK-UHFFFAOYSA-N 0.000 description 2
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 2
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 2
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- 239000002202 Polyethylene glycol Substances 0.000 description 2
- SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 description 2
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 2
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- 125000003545 alkoxy group Chemical group 0.000 description 2
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- 125000001494 2-propynyl group Chemical group [H]C#CC([H])([H])* 0.000 description 1
- LQJBNNIYVWPHFW-UHFFFAOYSA-N 20:1omega9c fatty acid Natural products CCCCCCCCCCC=CCCCCCCCC(O)=O LQJBNNIYVWPHFW-UHFFFAOYSA-N 0.000 description 1
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Classifications
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- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- 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)
- Wood Science & Technology (AREA)
- Engineering & Computer Science (AREA)
- Zoology (AREA)
- Health & Medical Sciences (AREA)
- Environmental Sciences (AREA)
- Dentistry (AREA)
- General Health & Medical Sciences (AREA)
- Agronomy & Crop Science (AREA)
- Plant Pathology (AREA)
- Pest Control & Pesticides (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Polysaccharides And Polysaccharide Derivatives (AREA)
- Saccharide Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Treatments For Attaching Organic Compounds To Fibrous Goods (AREA)
Abstract
棉花作物可被具有脱叶有效量的苯磺酰脲Ia和
Ib或它们的碱金属或碱土金属盐作用而脱叶
其中R′代表C1-C4烷基或C3-C5烷氧基烷基,
烷基又可带有1至3个卤素原子;R′还可以是C3-或
C4-链烯基或者是C3-或C4-链炔基,R2为氟、氯或
溴,R2′为氢、氯或溴;R3为氢、甲基或乙基,R4为卤
素、甲基或甲氧基,R5为甲基或甲氧基;R6为卤素、
C1-或C2-烷基、C1或C2-烷氧基、C1-或C2烷硫基
或C1-或C2-烷基胺;Z为CH或N。
Description
本发明涉及一种使棉花作物脱叶的方法,其中使用脱叶有效量的通式Ⅰa或Ⅰb所示的苯磺酰脲或它们的碱金属或碱土金属盐作用于棉花植物,通式Ⅰa或Ⅰb为:
其中R1代表C1-C4烷基或C3-C5烷氧基烷基,这些基团中的每个基团又可带有多至3个卤素原子;R1还可以是C3-或C4-链烯基或者是C3-或C4-链炔基,R2为氟、氯或溴,R2′为氢、氯、氟或溴;R3为氢、甲基或乙基,R4为卤素、甲基或甲氧基,R5为甲基或甲氧基;R6为卤素、C1-或C2-烷基,C1或C2-烷氧基,C1-或C2烷硫基或C1-或C2-烷基胺;Z为CH或N,
本发明进一步涉及一种使棉花作物脱叶的药剂,这种药剂除含有常规添加剂外,还含有苯磺酰脲Ⅰa或Ⅰb,或其碱金属或碱土金属盐,和作为增效剂的某一种N-苯基-3,4,5,6-四氢-邻苯甲酰亚胺类化合物(Ⅱ)
联邦德国专利申请413 565公开了苯磺酰脲的脱叶作用,这种苯磺酰脲的特点是在磺酰基的邻位带有含末端杂环取代基的烷氧基或链烯氧基。然而实例3表明叶子脱落的同时伴随着干燥。
美国专利申请4 127 405描述了下述苯磺酰脲对矮莱豆的除草作用,该苯磺酰脲的苯基是未被取代的或者在磺酰基的邻位被氟原子取代的。脱叶作用被作为一种伴随现象来描述,但是,对棉株的脱叶作用很差。
此外,欧洲专利申请0291 851和136 061介绍了在磺酰基邻位上带有烷氧基羰基的苯磺酰脲,但是,文中仅介绍了它的除草作用和生长调节作用。
欧洲专利申请0318 620公开了在磺酰基邻位上带有烷氧基羰基并且在间位上带有杂链烷基的苯磺酰脲。但是,文中仅介绍了它们的除莠作用和生长调节作用,以及对棉花作物的抑制生长作用。
在联邦德国专利申请3413490中,介绍了一种在磺酰基邻位上带有烷氧基羰基的苯磺酰脲,在该烷氧基上又带有肟基团,尽管文中指出了其用作脱落剂的可能性,但是特别提到了植物对其有很强的耐性,并举了棉花作物的例子。
欧洲专利申请7687公开了在磺酰基邻位带有烷氧基羰基的苯磺酰脲对矮菜豆的脱叶作用,对于棉株仅产生除莠作用而无脱叶作用。
人们也知道,磺酰脲的生物作用通常开始的很慢。例如,文献Proc.Br.Crof.Weeds 1980,I 7-14指出,在用磺酰脲2-氯-N-[[(4-甲氧基-6-甲基-1,3,5-三嗪-2-基)-氨基]-羰基]-苯磺酰胺处理敏感植物时,除莠作用或干燥作用出现的很慢,并伴随着褪绿、坏死、嫩芽枯萎和叶脉腿色的现象。
德国专利申请3905916介绍了N-苯基-3,4,5,6-四氢邻苯甲酰亚胺对植物器官的干燥和脱落作用
由于干燥剂和脱落剂可提高产量,所以引起了巨大的商业兴趣,特别在对棉花精耕细作时,必须使用脱落剂才能有效地使用拨毛机来收获棉桃,由于收获的原因,最好叶子以绿叶的形式脱下,而不使棉株枝干燥和枯萎,因为枯萎的残留叶子能够对土壤作用进而对以后棉纱的质量产生极为不利的影响。此外,迄今使用的脱叶剂并不能有效地阻止叶子的再生。
本发明的目的在于提供一种特殊的更好的脱除棉株叶子的方法和独特的更好的脱叶剂,这种脱叶剂对棉花作物最为有效。
我们已经发现,采用开头所述的方法来脱除棉株叶子可达到此目的,我们还发现了无前述缺点的棉株脱叶剂。
优选化合物Ⅰa或Ⅰb是那些式中具有下列意义的取代基的化合物:
R1为C1-C4烷基,如:甲基、乙基、正丙基、异丙基,正丁基、异丁基、仲丁基或叔丁基,C3-或C4-链烯基,具体地为2-丙烯基;C3-或C4-炔基,具体地为2-丙炔基;C1-C4卤代烷基,具体地为2-氯乙基;C3-C5-烷氧基烷基,具体地为2-甲氧基乙基;C或C-卤代烷氧基烷基,具体地为2-(2-氯乙氧基)-乙基:
R2为氟、氯或溴;
R2′为氢、氟、氯或溴;
R3为氢,甲基或乙基;
R4为卤素,(具体地为氯)甲基或甲氧基;
R5为甲基或甲氧基
R6为卤素(具体地为氯),也可以是甲基,乙基,甲氧基,乙氧基,甲硫基,乙硫基,甲胺基或乙胺基
适合于作棉花脱叶剂的化合物Ⅰa和Ⅰb列于表1和表2,表3和表4所列为此类化合物的具体的优选化合物
表4
R1R6
CH3Cl
CH3OCH3
C2H5OCH3
n-C3H7OCH3
由于磺酰基和羰基之间氮原子上的质子极易脱去,所以化合物Ⅰa和Ⅰb具有酸性。与碱结合则得到相应的盐,例如碱金属或碱土金属氢氧化物就是比较合适的碱,象氢氧化钠或氢氧化钾。合适的碱还有碱金属或碱土金属的醇盐,优选者是甲醇钠或甲醇钾。
合适的盐列于表5
表5
式Ⅰa化合物的盐
化合物 R1R2R3R4R5Z mp.[℃]
No.
3.1 CH3F H Cl OCH3CH >300
3.2 C2H5F H Cl OCH3CH >300
3.3 n-C3H7F H Cl OCH3CH >300
3.4 i-C3H7F H Cl OCH3CH
3.5 n-C4H9F H Cl OCH3CH
3.6 i-C4H9F H Cl OCH3CH
3.7 sec.-C4H9F H Cl OCH3CH
3.8 CH2-CH=CH2F H Cl OCH3CH
3.9 CH2-CH2Cl F H Cl OCH3CH
3.10 CH2-CH2-O-CH3F H Cl OCH3CH 167(分解)
3.11 CH3F H CH3OCH3CH
3.12 C2H5F H CH3OCH3CH >300
3.13 n-C3H7F H CH3OCH3CH
3.14 CH3Cl H OCH3OCH3CH
3.15 C2H5Cl H OCH3OCH3CH
3.16 n-C3H7Cl H OCH3OCH3CH
3.17 -i-C3H7Cl H OCH3OCH3N 185(分解)
3.18 CH2-CH2-O-CH3Cl H OCH3OCH3CH 154
在化合物Ⅰa的盐中,特别优选的是具有下式的钠盐:
例如,在欧洲专利申请2291851和0338424中公开了苯磺酰脲Ⅰa和Ⅰb,并且可以按上述文献介绍的方法制备这些化合物。
原则上,苯磺酰脲Ⅰa和Ⅰb可用下述方法获得
a)用异氰酸酯Ⅲa与胺Ⅳa反应
或者,用式Ⅲb异氰酸酯与胺Ⅳb反应
式Ⅲb为:
式Ⅳb为:
b)用磺酰胺Ⅴa与氨甲酸苯酯Ⅵa反应
式Ⅴa为:
或者,
用磺酰胺Ⅴb与氨甲酸苯酯Ⅵb反应
式Ⅴb为;
c)用氨甲酸苯酯Ⅶa与胺Ⅳa反应
式Ⅶa为:
或者
用氨甲酸苯酯Ⅶb与胺Ⅳb反应
式Ⅶb为:
苯磺酰脲Ⅰa和Ⅰb是收获棉桃前的适宜棉花作物脱叶剂,它们以很低的施用比作用即能有效也防止新芽的生长。在使用上述脲时,对绿叶的脱除作用比起干燥作用更占优势,即,枯萎现象有随着脱叶作用而产生的。这样可使收获后棉纱质量提高。
苯磺酰脲能够以下列形式使用:直接可喷洒溶液,粉剂、悬浮液(包括浓缩含水液,油状液或其它的悬浮液和分散液)、乳液、油分散液、糊剂、粉尘剂、撒播剂或颗粒剂,使用的方法可以是喷洒、雾化、撒播或浇注,应用的形式完全取决于使用方法,在任何情况下都应当保证有效成分能够极细地分散开来。
适合于制作直接可喷洒溶液、乳液,糊剂或油分散液的液体载体包括沸点适中至高沸点的矿物油馏分(例如:煤油或柴油,煤焦油)和植物油或动物油,脂肪烃、环烃和芳香烃例如苯,甲苯,二甲苯,石蜡,四氢化萘,烷基化萘或它们的衍生物如:甲醇、乙醇、丙醇、丁醇、氯仿、四氯化碳、环己醇、环己酮、氯苯或异佛尔酮、或强极性溶剂如:二甲基甲酰胺,二甲基亚砜,N-甲基吡咯烷酮或水。
向浓缩乳液、糊剂或可湿性粉剂(喷洒粉剂、油分散液)中加入水便可以水状施用。为了制备乳液、糊剂或油分散液及类似物质,将溶解在油或溶剂中的物质加入润湿剂,粘合剂,分散剂或乳化剂使其均匀分散在水中即得。然而,亦可制成可用水稀释的浓缩物,这种浓缩物由有效成分、润湿剂、粘合剂、分散剂或乳化剂组成,还可以含有溶剂或油。
合适的表面活性剂有下述化合物的碱金属盐,碱土金属盐,和铵盐。这些化合物包括木素磺酸,萘磺酸,苯磺酸,烷基芳基磺酸盐、烷基磺酸盐,烷基硫酸盐,二丁基萘磺酸的碱金属和碱土金属盐,月桂基醚硫酸盐,脂肪醇硫酸盐,脂及酸的碱金属和碱土金属盐,硫酸十六烷醇的盐,硫酸十七烷醇的盐,硫酸十八烷醇的盐,硫酸脂肪醇二醇醚的盐,磺化萘及萘衍生物与甲醛的缩合物,萘或萘磺酸与酚和甲醛的缩合物,聚氧化乙烯辛基苯酚醚,乙氧基异辛基苯酚,辛基苯酚,癸基苯酚,烷基苯酚聚乙二醇醚,三丁基苯酚乙二醇醚,烷基芳基聚醚醇,异三癸醇,脂肪醇/氧化乙烯缩合物,乙氧基蓖麻油,聚氧化乙烯烷基醚,乙氧基化聚氧化丙烯,月桂醇聚乙二醇醚缩醛,山梨醇酯,木素亚硫酸酯废液和甲基纤维素。
粉剂和散播、涂覆、浸渍的均匀粒剂是通过将活性组分结合进固体载体之中的方法来制备的。这些固体载体是矿物土,如:硅胶、硅石、硅酸盐、滑石、高岭土、粘土、石灰石、石灰、白垩、胶块土、黄土、白土、白云石、硅藻土、硫酸钙、硫酸镁、氧化镁等。还可以是粉状塑料、肥料(如:硫酸铵,磷酸铵,硝酸铵、脲素)、植物产品(如:谷类细粒,磨碎的树皮,木屑,果壳屑)、塞路路粉和其它固体载体。
配方中有效成分的重量百分含量为0.1%~95%,优选0.5%~90%。
配方实例:
Ⅰ.含90份重量的化合物No.1.13和10份重量的N-甲基-α-吡咯烷酮的溶液,适合于以极小的液滴状使用
Ⅱ.一种混合物,其组成如下:20份(重量)化合物No.1.25;80份(重量)二甲苯;10份(重量)由8~10摩尔氧化乙烯,1摩尔油酸N-单-乙醇酰胺组成的加合物;5份(重量)由40摩尔氧化乙烯,1摩尔蓖麻油组成的加合物,将其仔细地分散可水中便可得到分散液。
Ⅲ.一种含水分散液,其中含20份重量的化合物No.1.36,40份重量的环己酮,30份重量的异丙醇和20份重量的由40摩尔氧化乙烯和1摩尔蓖麻油组成的加合物。
Ⅳ.一种由下列物质组成的水分散液,20份重量的化合物No.1.60;25份重量的环己醇;65份重量沸程为210至280℃的矿物油;10份重量的由40摩尔氧化乙烯和1摩尔蓖麻油组成的加合物。
Ⅴ.一种由下列化合物组成的在研磨机中研磨过的混合物。80份重量的化合物No.1.73,3份重量的二异丁基萘-α-磺酸钠,10份重量的从亚硫酸盐废液提出的木素磺酸钠盐;7份重量的硅胶粉,将该混合物仔细地分散于水中便可得到喷洒液。
Ⅵ.一种充分混合的混合物,由3份重量的化合物No.1.84和97份重量的细分散高岭土组成,此粉剂有效成分含量3%(重量百分数)。
Ⅶ.一种由30份重量的化合物No.2.12,92份重量的硅胶粉和8份重量的液状石腊(液状石腊事先已喷洒于硅胶上)组成的充分混合的混合物,本配方使有效成分具有很好的粘着力。
Ⅷ.一种稳定的水分散液,它可进一步稀释。该水分散液的配方是:40份重量的化合物No.2.62;10份重量的苯酚磺酸/脲/甲醛缩合物的钠盐。2份重量的硅胶和48份重量的水。
Ⅸ.一种由下列物质组成的在研磨机中研磨过的混合物:10份重量的化合物No.3.17,4份重量的二异丁基萘-α-磺酸的钠盐,20份重量的从亚硫酸废液中提出的木素磺酸钠盐;38份重量的硅胶和38份重量的高岭土。将混合物极细地分散于10,000份重量的水中便可得到0.1%(重量百分数)的有效成分的喷洒液。
它们的作用和作用速率可通过加入提高效率的添加剂得到增加,这些添加剂可以是有机溶剂、润湿剂和油等。这样,实际使用的有效成分用量比例可以减少。
主要通过向叶子喷洒的方法来施用药剂。例如,可用下述方法来实施,用水作载体,通过常用的喷洒方法,每公顷地用喷洒液100~1,000升。可通过少量和超少量方法施用药剂,也可以用微粒的形式施用。
这种新药剂的施用比率可以是0.1至3,000g/ha优选0.5至1,000g/ha,特别是1至500g/ha。
这种药剂可以单独使用,也可以与其它的药剂或与其它的有效成分混合使用,如有必要,还可加入其它的脱叶剂、干燥剂、植物保护剂或杀虫剂,这完全取决于目的所在。
我们还发现这一新型药剂的混合物与下述的有效成分(A)-(C)结合使用,可以更好地控制棉花在干燥和脱叶后的嫩芽生长,脱叶作用可以成功地保留下来,甚至得到提高。
(A)除草有效成分
a.氯代N-乙酰苯胺类,例如:2-氯-N-(2,6-二甲基苯基)-N-(1H-吡唑-1-基甲基)-乙酰胺(俗名metazochlor),详见德专利申请第2648008号,
b.取代的喹啉-8-羧酸类,例如:3,7-二氯喹啉-8-羧酸(详见欧洲专利申请第104389号)和3-甲基-7-氯喹啉-8-羧酸(详见欧洲专利申请第60429号),
c.环己酮衍生物,例如:2-[(1-乙氧基亚胺)-丁基]-5-[2-(乙硫基)-丙基]-3-羟基-2-环己酮-1(俗名sethoxydim)(详见德国专利申请第2822304号和2-[1-(乙氧基亚胺)-丁基]-3-羟基-5-(2H-四氢噻喃-3-基]-2-环己酮-1(俗名cycloxydim)(详见德国专利申请第3121355号,
d.苯氧基烷基羧酸类,例如,(4-氯-2-甲基苯氧基)-乙酸,
e.3-异丙基-1H-2,1,3-苯并噻二嗪-4(3H)-酮2,2-二氧化物(详见德国专利申请第1542836号),
f.二硝基苯胺类,例如:N-(1-乙基丙基)-3,4-二甲基-2,6-二硝基苯胺。(详见德国专利申请第2241408号),
g.咪唑啉酮类,例如:2-[4,5-二氢-4-甲基-4-(1-甲基乙基)-5-氧代-1H-咪唑-2-基]-3-喹啉-羧酸
h.3,4,5,6-四氢苯邻二甲酰亚胺,例如:N-[5-(乙基-α-氯代丙烯酸酯)-4-氯代苯基]-3,4,5,6-四氢苯邻二甲酰亚胺(详见欧洲专利申请第0240659),以及
i.二苯醚,例如:5-[2-氯-4-(三氟甲基)-苯氧基]-2-硝基苯甲酸钠盐(详见德国专利申请第2311638号),
混合物的优选成分是:
2-甲基-6-乙基乙氧基甲基-2-氯代-N-乙酰苯胺
2-甲基-6-乙基-N-(甲氧基-1-甲基乙基)-2-氯-N-乙酰苯胺
2,6-二甲基-N-(1H-吡唑-1-基甲基)-2-氯-N-乙酰苯胺
2,6-二乙基-N-(甲氧基甲基)-2-氯-N-乙酰苯胺
3-甲基-7-氯代喹啉-8-羧酸(盐、酯)
3,7-二氯代喹啉-8-羧酸(盐、酯)
2-[(1-乙氧基亚胺)-丁基]-5-[2-(乙硫基)丙基]-3-羟基-2-环己酮-1(盐)
2-[(1-反式-氯烯丙基肟基)-丁基]-5-[2-(乙硫基)丙基]-3-羟基-2-环己酮-1(盐)
2-[(1-反式-氯烯丙基肟基)-丙基]-5-[2-(乙硫基)丙基]-3-羟基-2-环己酮-1(盐)
2-[(1-乙氧基亚胺)-丁基]-5-[2H-四氢噻喃-3-基)-3-羟基-2-环己酮-1(盐)
2-[(1-乙氧基亚胺)-丙基]-5-[2,4,6-三甲基苯基)-3-羟基-2-环己酮-1(盐)
2-甲基-4-氯苯氧基乙酸(盐、酯、酰胺)
2-[2-甲基-4-氯苯氧基]-丙酸(盐、酯、酰胺)
4-[2-甲基-4-氯苯氧基]-丁酸(盐、酯、酰胺)
4-[2,4-二氯苯氧基]-丁酸(盐、酯、酰胺)
2-[2,4-二氯苯氧基]-丙酸(盐、酯、酰胺)
2,4-二氯苯氧基乙酸(盐、酯、酰胺)
3,5,6-三氯吡啶-2-基氧代乙酸(盐、酯、酰胺)
3-(1-甲基乙基)-1H-2,1,3-苯并噻三嗪-4(3H)-酮2,2-二氧化物(盐)
3-(1-甲基乙基)-1-氰基-2,1,3-苯并噻三嗪-4(3H)-酮2,2-二氧化物(盐)
N-(1-乙基丙基)-3,4-二甲基-2,6-二硝基苯胺
2-[4,5-二氢-4-甲基-4-(1-甲基乙基)-5-氧-1H-咪唑-2-基]-3-喹啉羧酸
N-[5-(乙基α-氯代丙烯酸酯)-4-氯苯基]-3,4,5,6-四氢邻苯二甲酰亚胺
5-[2-氯-4-(四氟甲基)-苯氧基]-2-硝基苯甲酸乙氧基羰基甲基酯
5-[2-氯-4-(三氟甲基)-苯氧基]-2-硝基苯甲酸甲基磺酰胺
(B)脱叶剂和干燥剂
这些是众所周知的,例如下列文献有详述。Cathey,G.W.(1986)Physiology of defoliation in cotton production,in Cotton Physiology(J.R.Mauney,J.McD Stewart,eds)The Cotton Foundation Reference Book Series No.1第14章,第143-153页,Morgn P.W.(1985)Chemical manipulation of absci-ssion and desiccation,in Agricultural Chemicals of the Future(J.L.Hilton,ed.)BARC Symposium 8,第61-74页,Rowman & Allanheld公司出版,渥太华
a.脲衍生物,例如N-苯基-N′-1,2,3-噻二唑-5-基脲(已在德国专利申请第2506 690号和第2619861号中公开);N-苯基-N′-1,3,4-噻二唑-2-基脲(详见德国专利申请第3612830号),或N-苯基-N′-2-氯吡啶-3-基脲(详见德国专利申请第2843711号)
b.(2-氯乙基)-磷酸
c.S,S,S-三丁基硫代磷酸酯和S,S,S-三丁基三硫代亚磷酸酯
d.2,3-二氢-5,6-二甲基-1,4-二硫杂环己烷-1,1,4,4-四氧化物
e.N-(磷酰甲基)-甘氨酸盐,例如:异丙基铵盐
f.氯酸镁和氯酸钠
g.1,2-二氢哒嗪-3,6-二酮
h.7-氧二环[2.2.1]庚烷-2,3-二羧酸(俗名:endothall)
i.6,7-二氢二吡啶酚(1,2-α:2′,1′-C)吡啶鎓离子二溴化物单水合物(俗名diquat)和1,1′-二甲基-4,4′-双吡啶鎓离子二氯化物或二甲基硫酸盐(俗名:paraquat)
混合物的优选成分是:
N-苯基-N′-1,2,3-噻二唑-5-基脲
N-苯基-N′-1,3,4-噻二唑-2-基脲
N-苯基-N′-2-二氯吡啶-3-基脲
N-(3,4-二氯苯基)-N′,N′-二甲基脲
2-氯乙基膦酸
S,S,S-三丁基三硫代磷酸酯,S,S,S-三丁基三硫代亚磷酸酯。
2,3-二氢-5,6-二甲基-1,4-二硫杂环己烷1,1,4,4-四氧化物
N-(磷酰甲基)甘氨酸(盐)
1,2-二氢哒嗪-3,6-二酮
高氯酸盐
7-氧杂双环[2.2.1]庚烷-2,3-二羧酸(盐、酯、酰胺)
1,1-乙烯-2,2-双吡啶鎓二溴化物
(C)生长抑制剂
a.下列各种季铵盐:N,N-二甲基氮杂环庚烷鎓盐,N,N-二甲基哌啶鎓盐,N,N-二甲基六氢哒嗪鎓盐,N,N-二甲基四氢哒嗪鎓盐,N-甲基吡啶鎓盐,N,N-二甲基吡咯烷鎓盐和N,N,N-三甲基-N-2-氯代乙基铵盐,特别是,N-2-氯代乙基-N-三甲基氯化铵(俗名:Chlormequat Chloride)和N,N-二甲基哌啶氯化物(俗名:Mepiquat Chloride)
b.嘧啶化合物,详见美国专利第3,818,009号和“植物生长调节杂志”第27卷,第7期(1988年)(例如:俗名为ancimidol或flurpimidol的化合物)
c.吡啶化合物,详见联邦德国专利申请第3015025号。
d.降冰片烷基二氮杂环丁烯,详见德国公开申请第2,615,878和第2,742,034号
e.具有生长调节作用的三唑类化合物。详见下列文献:欧洲申请P88104320.2;British Crop Protection Conference-Weeds1982,Vol.1.BCPC Publications,Croydon,1982,Page 3;Plant Cell Physiol.25,611;Pestic.Sci.19,153;J.Agron.Crop Sci.158,324或J.Plant Growth Regul.4,181。例如:1-苯氧基-3-(1H-1,2,4-三唑-1-基)-4-羟基-5,5-二甲基-己烷
f.2-酰基-3-羟基环己-2-烯基-1-酮类,详见欧洲专利申请126713或123001。
g.1-(4-氯代苯氧基)-3,3-二甲基-1-[1,2,4-三唑-1-基]-丁酮-2(俗名:triadimefon)N-[2,4-二甲基-5-(三氟甲基磺酰胺基)]-苯基乙酰胺(俗名:mefluidide)
2-氯代-2′,6′-二甲基-N-[甲氧基甲基]-2酰苯胺(俗名:alachlor)
S-乙基二丙基硫代氨基甲酸酯(俗名:EPTC)琥珀2,2-二甲基酰肼(俗名:daminozide)
混合物的优选成分是:
N,N,N-三甲基-N-2-氯代乙基铵盐类
N,N-二甲基哌啶鎓盐
N-甲基吡啶鎓盐
α-环丙基-α-(4-甲氧基苯基)-5-嘧啶甲醇
α-环丙基-α-(4-三氟甲氧基苯基)-5-嘧啶甲醇
5-(4-氯代苯基)-3,4,5,9,10-五氮杂四环-[5.4.1.02,6.08,11]-十二-3,9-二酮
全反式-8-(4-氯代苯基)-3,4,8-三氮杂四环-[4.3.1.0.02,5.07,9]-癸酮-3
琥珀单-N,N-二甲基酰肼
N,N-二丙基硫代氨基甲酸乙基酯
N-2,4-二甲基-5-(三氟甲基)-磺酰基胺基苯基-乙酰胺
1-(4-氯代苯氧基)-3,3-二甲基-1-(1,2,4-三唑-1-基)-2-丁酮
2-丙基羰基-5-乙氧基羰基-3-羟基-2-环己酮-1
1-(1,2,4-三唑-1-基)-1-甲氧基-2-(2,4-二氯苯基)-丙醇-2
2,2-二甲基-4-(1,2,4-三唑-1-基)-6-苯氧基己醇-3
2,2-二甲基-4-(1,2,4-三唑-1-基)-5-(4-氯代苯基)戊醇-1
2,2-二甲基-4-(1,2,4-三唑-1-基)-5-(4-氯苯基)戊烯-4-醇-1
2,2-二甲基-4-(1,2,4-三唑-1-基)-5-环己基戊烯-4-醇-3
1-(5-甲基-1,3-二噁烷-5-基)-4-(1,2,4-三唑-1-基)-4-(4-三氟甲基苯基)-丙烯醇-2
化合物Ⅰa或Ⅰb的特别优选的化合物是或Ⅱ所示的取代的N-苯基-3,4,5,6-四氢邻苯二甲酰亚胺:
式中R7为氢,氟或氯
R8为氯,且,
R9为
a)基团
其中
Q为氧或硫
R10为氢、氯、溴、氰基或C1-C6烷基,且,
R11为氢,C1-C8烷基,C1-C8-链烯基,C3-或C4-炔基,C1-C8-烷氧基烷基,C1-C8-烷硫基烷基,苯基-C1-C8烷基或C3-C6-环烷基
或
b)基团
其中
X为氧或硫
n取0或1
R12为氢或C1-C4烷基,该烷基又可以被下列基团取代:羟基,卤素,氰基,巯基,C1-C4烷氧基,C1-C4-烷硫基,C1-C4烷基碳酰氧基或C1-C4-烷氧基羰基-C1-C4-烷硫基,且,
R13为氢或C1-C3-烷基
或者
c)基团OR14,其中
R14为C1-C4-烷基,C3-或C4-链烯基;C3-或C4-炔基,C1-C4-烷基羰基,C1-C4-烷氧基羰基-C1-C4-烷基,四氢糠基,二氢吡喃甲基,二氢噻喃甲基,四氢吡喃甲基或四氢噻喃甲基。
关于N-取代的四氢苯邻二甲酰亚胺(Ⅱ)的制备方法,德国专利申请……(申请号:P3905916.2)中有详细叙述,它们可以从3,4,5,6-四氢邻苯二甲酸酐和相应的取代苯胺衍生物来制备,而上述原料又可通过还原相应的硝基化合物获取,反应在惰性溶剂中进行,温度为20-200℃,优选40-150℃。适宜的溶剂是低级烷基羧酸,如:冰乙酸或丙酸,或者是对质子惰性溶剂,如甲苯或二甲苯,反应过程中使用酸性催化剂,如:芳香族磺酸。化合物Ⅱ和Ⅱa的制备可按类似于下述文献所述方法进行,欧洲专利申请第240659,第300387,第300398,第236916,第313963,第319791和320677号或德国专利申请第8109035和第3533440号或英国专利申请第207100号。
苯磺酰脲Ⅰa或Ⅰb以及四氢邻苯二甲酰亚胺Ⅱ的用量比例为100∶1至1∶100(重量比),但是混合物的优选比例是50∶1至1∶50。
应用实例:
下列化合物被用作对比药剂
A.6,7-二氢二吡啶酚(1,2-α:2′,1′-C)吡啶鎓二溴化物单水合物
B.2-氯乙基磷酸
C.N-苯基-N′-(1,2,3-噻二唑-5-基)-脲
D.德国专利申请第3413565号公开的
以及
E.欧洲专利申请第0240659号公开的增效剂
对比药剂A、B和C以最常见的商品形式使用,对比药剂E按配方实例Ⅲ类似方法配制,对比药剂D和苯磺酰脲ⅠA或Ⅰb按配方实例Ⅸ类似方法配制
配方中水用量换算为1,000l/ha
所用植物试样为初生的,六个叶子的棉株(无子叶),牌号是Stoneville 825,试样在温室中长成(相对湿度50~70%)
实施例1
将上述有效成分的水溶液制剂充分喷注在叶子上(喷洒液中又加入重量百分数为0.15%的脂肪醇烷氧基化合物Plurafac LF 700),10天后,测定脱落的叶子数和脱落的百分数,对于未经处理的棉株,则未见脱落现象。同时测定了棉株的抽芽情况。(白天/夜间温度:25/18℃)
含有效成分 换算施用 脱叶 抽芽情况
药剂序号No. 比率[kg/ha] %
1.13 0.016 80 +
1.25 0.016 69 +++
1.36 0.016 50 ++
1.60 0.016 86 +
1.84 0.016 73 +
1.108 0.016 68 +
2.12 0.016 95 0
2.62 0.016 61 ++++
对比药剂 0.500 46 ++++
B
*)评定:++++显著抽芽,+轻微抽芽,0无抽芽。
实施例1的结果表明,即使施用的比率很低,这种新药剂也可以使棉株脱叶并有效地抑制抽芽,显然它优于对药试剂。
实施例2
将上述有效成分的水溶液制剂充分喷注在叶子上(喷洒液中又加入重量百分数为0.15%的脂肪醇烷氧基化合物Plurafac LF 700),10天后,测定脱落的叶子数和脱落的百分数,对于未经处理棉株,则未见脱落现象。同时测定了棉株的抽芽情况。(白天/夜间温度:25/18℃)
含有效成分 换算施用 脱叶
药剂序号No. 比率[kg/ha] %
1.36 0.031 74
1.48 0.031 61
1.72 0.031 65
1.73 0.031 80
1.74 0.031 35
1.4 0.031 31
3.17 0.031 60
对比药剂 A 0.062 16
对比药剂 B 0.031 4
对比药剂 C 0.031 27
对比药剂 D 0.031 0
实施例2的结果表明,新药剂与有效成分A,B和C,特别与密切相关的化合物D比较,其脱叶作用显著提高
实施例3
将上述有效成分的水溶液制剂充分喷注在叶子上(喷洒液中又加入重量百分数为0.15%的脂肪醇烷氧基化合物Plurafac LF 700),10天后,测定脱落的叶子数和脱落的百分数,对于未经处理的棉株,则未见脱落现象。同时测定了棉株的抽芽情况。(白天/夜间温度:26/18℃)
含有效成分 换算施用 脱叶 抽芽情况
药剂序号No. 比率[kg/ha] %
1.36 0.031 94 +++
1.36+E 0.031+0.125 90 ++
E 0.125 77 ++++
*)评定:++++显著,+轻微,0无
实施例3的结果表明,N-[5-(乙基α-氯代丙烯酸酯)-4-氯苯基]-3,4,5,6-四氢邻苯二甲酰亚胺E增强了化合物No.1.36对棉株抽芽的抑制作用。
Claims (10)
2、按权利要求1所述的使棉花作物脱叶子的方法,其中使用脱叶有效量的苯磺酰脲Ⅰa作用于棉花作物,式中,R1为甲基、乙基、正丙基、异丙基或2-甲氧基乙基,R2为氟、氯或溴,R3为氢或甲基,R4为氯,甲基或甲氧基,R5为甲基或甲氧基,Z为CH。
3、按权利要求1所述的使棉花脱叶子的方法,其中使用脱叶有效量的苯磺酰脲Ⅰa作用于棉花作物,式中R1为甲基,R2为氟,R3为氢,R4和R5分别为甲基或甲氧基,Z为氮。
4、按权利要求1所述的使棉花脱叶子的方法,其中使用脱叶有效量的苯磺酰脲Ⅰa钠盐作用于棉花作物,式中R1为异丙基、R2为氟、R3为氢,R4和R5分别为甲氧基,Z为氮。
5、按权利要求1所述的使棉花脱叶子的方法,其中使用脱叶有效量的苯磺脲Ⅰb作用于棉花作物,式中R1为甲基、乙基或正丙基,R2′和R3分别为氢,R6为氯,甲氧基或甲硫基。
6、按照权利要求1或2或3或4或5所述的用于使棉花作物脱叶的药剂,该药剂除含有常用添加剂外,还含有苯磺酰脲Ⅰa或Ⅰb,或它们的碱金属盐或碱土金属盐和作为增效剂的N-苯基-3,4,5,6-四氢邻苯二甲酰亚胺Ⅱ
式中R7为氢,氟或氯
R8为氯,且,
R9为
a)基团
其中
Q为氧或硫
R10为氢、氯、溴、氰基或C1-C6烷基,且,
R11为氢,C1-C8烷基,C3-C4-链烯基,C1-或C8-炔基,C1-C8-烷氧基烷基,C1-C8-烷硫基烷基,苯基-C1-C8烷基或C3-C6-环烷基
或
b)基团
其中
X为氧或硫
n取0或1
R12为氢或C1-C4烷基,该烷基又可以被下列基团取代:羟基,卤素,氰基,巯基,C1-C4烷氧基,C1-C4-烷硫基,C1-C4烷基羰基氧基或C1-C4-烷氧基羰基-C1-C4-烷硫基,且,
R13为氢或C1-C3-烷基
或者
c)基团OR14,其中
R14为C1-C4-烷基,C3-或C4-链烯基;C3-或C4-炔基,C1-C4-烷基羰基,C1-C4-烷氧基羰基-C1-C4-烷基,四氢糠基,二氢吡喃甲基,二氢噻喃甲基,四氢吡喃甲基或四氢噻喃甲基。
8、按权利要求1或3或4所述的用于使棉花作物脱叶的药剂,该药剂除含有常用的添加剂外,还含有苯磺酰脲Ⅰa和作为增效剂的N-苯基-3,4,5,6-四氢邻苯二甲酰亚胺(Ⅱ),式(Ⅱ)中R7为氢,R8为氯,R9为基团
R10为氯或溴R11为甲基或乙基。
9、按权利要求5所述的用于使棉花作物脱叶的药剂,该药剂含有常用的添加剂外,还含有苯磺酰脲Ⅰb和作为增效剂的N-苯基-3,4,5,6-四氢邻苯二甲酰亚胺(Ⅱ)式(Ⅱ)中R7为氢,R8为氯,R9为基团
R10为氯或溴,R11为甲基或乙基
10、一种使棉花脱叶的方法,其中使用脱叶有效量的权利要求6或7或8或9所述药剂作用于棉花作物。
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JPS61103809A (ja) * | 1984-10-25 | 1986-05-22 | Sumitomo Chem Co Ltd | 除草組成物 |
AU574859B2 (en) * | 1984-11-13 | 1988-07-14 | Sumitomo Chemical Company, Limited | Herbicidal compositions containing tetrahydro-isoindole-1,3-diones and pyrimidinyl amino carbonyl amino sulphonyl benzoates |
JPS63179805A (ja) * | 1987-01-22 | 1988-07-23 | Sumitomo Chem Co Ltd | 除草組成物 |
DE3716657A1 (de) * | 1987-05-19 | 1988-12-01 | Basf Ag | Herbizide sulfonamide, verfahren zu ihrer herstellung und ihre verwendung zur beeinflussung des pflanzenwachstums |
EP0318620A1 (en) * | 1987-12-04 | 1989-06-07 | E.I. Du Pont De Nemours And Company | Herbicidal sulfonamides |
DE3905916A1 (de) * | 1989-02-25 | 1990-08-30 | Basf Ag | Verwendung von derivaten des n-phenyl-3,4,5,6-tetrahydrophthalimids zur desikkation und abszission von pflanzenorganen |
-
1990
- 1990-07-19 GR GR900100558A patent/GR1000753B/el not_active IP Right Cessation
- 1990-07-23 IL IL9515690A patent/IL95156A/en not_active IP Right Cessation
- 1990-08-02 US US07/561,611 patent/US5171352A/en not_active Expired - Lifetime
- 1990-08-02 IT IT02117990A patent/IT1243190B/it active IP Right Grant
- 1990-08-06 BR BR909003846A patent/BR9003846A/pt not_active IP Right Cessation
- 1990-08-06 ZA ZA906169A patent/ZA906169B/xx unknown
- 1990-08-06 AU AU60151/90A patent/AU6015190A/en not_active Abandoned
- 1990-08-07 CN CN90106897A patent/CN1049439A/zh active Pending
- 1990-08-07 TR TR90/0740A patent/TR24994A/xx unknown
- 1990-08-07 ES ES9002135A patent/ES2032252B1/es not_active Expired - Fee Related
Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO2009052701A1 (fr) | 2007-10-16 | 2009-04-30 | Sinopec Yangzi Petrochemical Company Ltd. | Catalyseur non métallocène supporté sur un composé de magnésium et son procédé de préparation |
Also Published As
Publication number | Publication date |
---|---|
IT1243190B (it) | 1994-05-24 |
ES2032252B1 (es) | 1994-01-16 |
BR9003846A (pt) | 1991-09-03 |
ES2032252A1 (es) | 1993-01-16 |
IT9021179A1 (it) | 1992-02-02 |
IL95156A0 (en) | 1991-06-10 |
TR24994A (tr) | 1992-08-21 |
GR1000753B (el) | 1992-12-30 |
IL95156A (en) | 1994-07-31 |
GR900100558A (en) | 1991-12-30 |
AU6015190A (en) | 1991-02-07 |
ZA906169B (en) | 1992-04-29 |
US5171352A (en) | 1992-12-15 |
IT9021179A0 (it) | 1990-08-02 |
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