GB2038334A - O-Sulfamoylglycolic acid amide derivatives - Google Patents

O-Sulfamoylglycolic acid amide derivatives Download PDF

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GB2038334A
GB2038334A GB7944535A GB7944535A GB2038334A GB 2038334 A GB2038334 A GB 2038334A GB 7944535 A GB7944535 A GB 7944535A GB 7944535 A GB7944535 A GB 7944535A GB 2038334 A GB2038334 A GB 2038334A
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sulfamoylglycolic
acid amide
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amide derivative
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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D295/00—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms
    • C07D295/16—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms acylated on ring nitrogen atoms
    • C07D295/18—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms acylated on ring nitrogen atoms by radicals derived from carboxylic acids, or sulfur or nitrogen analogues thereof
    • C07D295/182—Radicals derived from carboxylic acids
    • C07D295/185—Radicals derived from carboxylic acids from aliphatic carboxylic acids
    • 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
    • A01N41/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a sulfur atom bound to a hetero atom
    • A01N41/02—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a sulfur atom bound to a hetero atom containing a sulfur-to-oxygen double bond
    • A01N41/04—Sulfonic acids; Derivatives thereof
    • A01N41/08—Sulfonic acid halides; alpha-Hydroxy-sulfonic acids; Amino-sulfonic acids; Thiosulfonic acids; Derivatives thereof
    • 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
    • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/34—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom
    • A01N43/46—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom rings with more than six members
    • 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
    • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/72—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms
    • A01N43/84—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms six-membered rings with one nitrogen atom and either one oxygen atom or one sulfur atom in positions 1,4
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D295/00—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms
    • C07D295/22—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with hetero atoms directly attached to ring nitrogen atoms
    • C07D295/26—Sulfur atoms

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  • Life Sciences & Earth Sciences (AREA)
  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Dentistry (AREA)
  • Wood Science & Technology (AREA)
  • Plant Pathology (AREA)
  • Health & Medical Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Agronomy & Crop Science (AREA)
  • General Health & Medical Sciences (AREA)
  • Pest Control & Pesticides (AREA)
  • Zoology (AREA)
  • Environmental Sciences (AREA)
  • Agricultural Chemicals And Associated Chemicals (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
  • Hydrogenated Pyridines (AREA)
  • Plural Heterocyclic Compounds (AREA)

Abstract

O-Sulfamoylglycolic acid amide derivatives represented by the general formula <IMAGE> wherein R1 and R2, which may be the same or different, each represent a substituted or unsubstituted alkyl, alkenyl, alkynyl, cycloalkyl or alkoxy group which may be substituted with a halogen atom, an alkoxy or alkylthio group, or R1 and R2 may form in cooperation with each other a heterocyclic ring which may be substituted with a lower alkyl group, R3 represents a hydrogen atom or a lower alkyl group, and <IMAGE> represents a monocyclic or bicyclic ring which may be substituted with a lower alkyl group which are useful as herbicides may be obtained either by reacting <IMAGE> wherein X is, for example, chlorine; or by reacting <IMAGE> with <IMAGE>

Description

SPECIFICATION O-sulfamoylglycolic acid amide derivatives This invention relates to novel O-sulfamoylglycolic acid amide derivatives and utilization thereof as herbicide. More particularly, the invention is concerned with an O-sulfamoyglycolic acid amide derivative represented by the general formula (I)
wherein R1 and R2, which may be the same or different, each represent a substituted or unsubstituted alkyl, alkenyl, alkynyl, cycloalkyl or alkoxy group which may be substituted with a halogen atom, an alkoxy or akylthio group, or R1 and R2 may form in cooperation with each other a heterocyclic ring which may be substituted with a lower alkvl (generally of 1 to 6 carbon atoms) group, F3 represents a hydrogen atom or a lower alkyl group, and Nffi) represents a monocylic or bicyclic ring which may be substituted with a lower alkyl group, and further with a herbicide comprising as its active ingredient the O-sulfamoylglycolic acid amide derivative.
As compounds heretofore known to be similar in structure to the compounds of the present invention, there are disclosed in Japanese Pre-Exam. Publication No. 20331/1 974 those represented by the general formula
wherein R represents hydrogen, alkyl, cycloalkyl or halogen-alkyl residue.
We synthesized a series of O-sulfamoylglycolic acid amide derivatives and studied extensively and assiduously their practical usefulness as herbicides. As the result, it has been found that specific compounds of the aforesaid general formula (I), when they are applied to a paddy field or farmland, exhibit excellent herbicidal effects on paddy field weeds, such as Echinochloa dryzicola, manochoria, false pimpernel, toothcup, bulrush and water plantain, and farmland weeks such as crab-grass, chickweel, common purslane, lambsquarter and amaranth, at either stage before or after germination thereof.Thus, the compounds of the present invention as mentioned above can be said to be exceilent herbicides since they possess strong herbicidal effects on weeds without any phytotoxicity on useful crops, such as paddy rice, soy bean, radish, wheat, beet, corn, etc. and, moreover, are usable without anxiety about harmfulness to mammals or fish poison.
Such features of the present invention are those which cannot be anticipated by any of those skilled in the art from the technical level prevailing at that time when known compounds similar in structure to the present compounds became available, and thus the present compounds are fully of practical usefulness as herbicide.
The compounds of the present invention can be prepared by either process (A) or (B) as will be explained hereinafter.
Process (A) The present compound can be prepared by allowing disubstituted aminosulfonyl halides to react with oxyacid amide derivatives. The reaction may be represented by the reaction formula mentioned below.
wherein R1, R2, R3 and
are each as defined in the general formula (I).
In preparing the present compounds according to the process w, Ills usuaiiy prulL'Lduly LU un L organic solvents such as hydrocarbons, halogen-substituted hydrocarbons, ethers, etc., though the compounds (II) or (III) may be usable as solvent. Usable as acid binding agents in this process are any of organic and inorganic bases. For carrying out the reaction smoothly, it is preferably to subject to the reaction the compounds (III) after converting them with sodium hydride, sodium amide, sodium alcolate or alkali metals into corresponding metal salts. For the purpose of shortening the reaction time, it may be as well to carry out the reaction by elevating the reaction temperature up to a boiling point of the solvent used, though the reaction proceeds either at room temperature or under cooling.After completion of the reaction, the compound (I) of the present invention can be obtained by separating salts of the acid binding agent by filtration from the reaction mixture, followed by distilling off the solvent therefrom.
Process (B) The present compounds can be prepared by allowing O-(N-substituted or monosubstituted aminosulfony I)oxyacid amide derivatives to react with alkylating agents such as sulfuric acid diesters. This reaction may be represented by the following reaction formula
wherein R1, R2, R3 and
are each as defined in the general formula (I).
The process (B) is applied to the preparation of such ones out of the present compounds (I) as having no ring formed by combination of R1 and R2. For the purpose of obtaining the present compounds in high purity according to this process, it may be as well to use such ones out of the compounds (V) as being of symmetrical type, though the compounds (V), which are either of symmetrical or asymmetrical type, are usable. Further, it is usually preferably to use, as the reaction solvent, hydrocarbons, halogen-substituted hydrocarbons, ethers, ketones, water, etc., though the compounds (V) may be used as the reaction solvent.
Usable acid binding agents include inorganic bases such as potassium carbonate, etc. or organic bases such as tertiary amines, etc. The reaction may be usually carried out at any temperatures elevated up to a boiling point of the solvent used, though the reaction proceeds even at room temperature. Although the reaction time varies according to the kind of solvent used orto the reaction temperature employed, the reaction can be terminated in a short period of time by using potassium carbonate as the acid binding agent in ketones and elevating the reaction temperature. After completion of the reaction, the present compounds can be obtained by treating the reaction mixture in the same manner as in the process (A).
Typical examples of the present compounds prepared by the processes (A) and (B) are illustrated below with reference to Examples 1 - 5 and 6 - 9, respectively. It should be construed, however, that the scope of the present invention is not limited only to these examples.
Example 1
A 300 ml flask was charged with 100 ml of tetrahydrofuran and 2.6 g of sodium hydride, and thereto were dropwise added with stirring a solution of 12.9 g of glycolic acid tetramethyleneamide in 30 ml of tetrhydrofuran. The resulting mixture in the flask was heated until evolution of hydrogen gas ceased to form completely alcolate of glycolic acid tetramethyleneamide, followed by cooling. to the mixture was dropwise added with water-cooling a solution of 17.2 g of diethylaminosulfonyl chloride in 30 ml of tetrahydrofuran, and the resulting mixture was further stirred for 30 minutes.
After completion of the reaction, the reaction mixture was charged with benzene and water, and an organic layer formed was collected by separation. After having been washed with water, the organic layer was dried over anhydrous sodium sulfate. On distilling off the solvent under reduced pressure, 24.0 g of the title compound was obtained as a brownish yellow liquid. Purification by centrifugal chromatography over silica gel gave a pale yellow liquid showing n25 = 1.4850. The chemical shift of nuclear magnetic resonance spectrum as measured (in deuterochloroform) was found to be as follows:
A solution of 2.3 g of sodium in 100 ml of ethanol was charged with 14.3 g of glycolic acid pentamethyleneamide.The resulting solution was evaporated to dryness, and the resulting solid was suspended in benzene, followed by addition thereto of 14.4 g of dimethylaminosulfonyl chloride. The resulting mixture was then stirred under reflux for 2 hours. After cooling, the mixture was charged with water, and a benzene layer formed was collected by separation. The benzene layer, after washing with water, was dried over anhydrous sodium sulfate. On distilling off the solvent under reduced pressure, 21.5 g of the title compound was obtained as a yellow liquid.Purification by centrifugal chromatography over silica gel gavethite crystals showing m.p. 42 - 44"C. The chemical shift of nuclear magnetic resonance spectrum as measured (in deuterochloroform) was found to be as follows:
To a 300 ml flask charged with 100 ml of tetrahydrofuran and 2.6 g of sodium hydride was dropwise added with stirring a solution of 14.3 g of glycolic acid pentamethyleneamide in 30 ml of tetrahydrofuran. The resulting mixture was stirred with heating until evolution of hydrogen gas ceased, followed by cooling. To the mixture thus treated was dropwise added with water-cooling a solution of 15.8 g of N-methyl-Nethylaminosulfonyl chloride in 30 ml of tetrhydrofuran, followed by stirring for 30 minutes.
After completion of the reaction, benzene was added to the reaction mixture and an organic layer formed was collected by separation. After having been washed with water, the organic layer was dried over anhydrous sodium sulfate. On distilling off the solvent under reduced pressure, 23.0 g of the title compound was obtained as a pale brown liquid. Purification by centrifugal chromatography over silica gel gave a pale yellow liquid showing n025 1.4859.The chemical shift of nuclear magnetic resonance spectrum as measured (in deuterochloroform) was found to be as follows:
To a 300 ml flask charged with 100 ml I ml oftetrahydrofuran and 2.6 g of sodium hydride was dropwise added with stirring a solution of 14.3 g of glycolic acid pentamethyleneamide in 30 ml of tetrahydrofuran. The resulting mixture was heated until evolution of hydrogen gas ceased to form completely alcolate of glycolic acid pentamethyleneamide, followed by cooling. To the mixture thus treated was dropwise added with water-cooling a solution of 20.0 g of 1-tetramethyleneiminosulfonyl chloride in 30 ml of tetrahydrofuran, followed by stirring for 30 minutes.
After completion of the reaction, benzene and water were added to the reaction mixture and an organic layer formed was collected by separation. After having been washed with water, the organic layer was dried over anhydrous sodium sulfate. On distilling off the solvent under reduced pressure, 25.9 g of the title compound was obtained a brownish yellow liquid.This compound crystallized in a little while, and recrystallization from a cyclohexane-acetone solvent mixture gave white crystals, m.p. 59 - 61"C. The chemical shift of nuclear magnetic resonance spectrum as measured (in deuterochloroform) was found to be as follows,
Example 5
To a 300 ml flask charged with 100 ml of tetrahydrofuran and 2.6. g of sodium hydride was dropwise added with stirring a solution of 17.1 g of lactic acid hexamethyleneamide in 30 ml of tetrahydrofuran. The resulting mixture was heated until evolution of hydrogen gas ceased, followed by cooling. To the mixture thus treated was dropwise added with water-cooling a solution of 14.4 g of dimethylaminosulfonyl chloride in 30 ml of tetrahydrofuran. Thereafter, the resulting mixture was refluxed with stirring for 1 hour.
After completion of the reaction, the reaction mixture was cooled and charged with benzene and water, and an organic layer formed was collected by separation. The organic layer was then washed with water and dried over anhydrous sodium sulfate. On distilling off the solvent under reduced pressure, 24.5 g of the title compound was obtained as a brown liquid. Purification by centrifugal chromatography over silica gel gave a pale yellow liquid, n025 = 1.4843.The chemical shift of nuclear magnetic resonance spectrum as measured (in deuterochloroform) was found to be as follows:
Example 6
A300 ml flask was charged with 27.8 g of O-(isopropylaminosulfonyl)-glycolic acid hexamethyleneamide, 12.6 of dimethyl sulfate, 13.8 g of anhydrous potassium carbonate and 150 ml of methyl ethyl ketone, and the contents of the flask were refluxed with stirring for 2 hours, followed by cooling. To the resulting mixture were added benzene and water, and an organic layer formed was collected by separation. After having been washed with water, the organic layer was dried over anyhdrous sodium sulfate, and the solvent was distilled off under reduced pressure to obtain 26.9 g of the title compound as a pale yellow liquid.Purification by centrifugal chromatography over silica gel gave a colorless liquid, 25 = 1.4899. The chemical shift of nuclear magnetic resonance spectrum as measured (in deuterochloroform) was found to be as follows
a : 2.80 ppm b : 1.20ppm c : 4.25 ppm d : 4.69 ppm e : 3.47 ppm Example 7
A 300 ml flask was charged with 26.4 g of O-(ethylaminosulfonyl)-glycolic acid 4methylphentamethyleneamide, 15.4 g of diethyl sulfate, 13.8 g of anhydrous potassium carbonate and 100 ml of acetone, and the contents of the flask were refluxed with stirring for 3 hours, followed by cooling. To the resulting mixture were added benzene and water, and an organic layer formed was collected by separation.After having been washed with water, the organic layer was dried over an hydros sodium sulfate, and the solvent was distilled off under reduced pressure to obtain 26.6 g of the title compound as a pale brown liquid. Purification by centrifugal chromatography over silica gel gave a pale yellow liquid, nor2)5 = 1.4813.The chemical shift of nuclear magnetic resonance spectrum as measured (in deuterochloroform) was found to be as follows:
a : 1.23ppm b : 3.37ppm c : 4.68ppm d 0.95 ppm Example 8
A 300 ml flask was charged with 28.0 g of O-(2-methoxyethylaminosulfonyl)-glycolic acid hexamethyleneamide, 12.6 g of dimethyl sulfate, 13.8 g of anhydrous potassium carbonate and 150 ml of methyl ethyl ketone, and the contents of the flask were refluxed with stirring for 1 hour, followed by cooling. To the mixture thus treated were added benzene and water, and an organic layer formed was collected by separation. After having been washed with water, the organic layer was dried over anhydrous sodium sulfate, and the solvent was distilled off under reduced pressure to botain 27.0 g of the title compound as a pale yellow liquid.Purification by centrifugal chromatograph over silica gel gave a colourless liquid, n025 = 1.5007. The chemical shift of nuclear magnetic resonance spectrum as measured (in deuterochloroform) was found to be as follows:
a 3.05 ppm b : 3.36ppm c 3.55 ppm d : 3.52 ppm e 4.75ppm f : 3,50 ppm Example 9
A 500 ml flask was charged with 23.6 g of O-(aminosulfonyl)-glycolic acid 2-methylpentamethyleneamide, 25.2 g of dimethyl sulfate, 27.6 g of anhydrous potassium carbonate and 200 ml of acetone, and the contents of the flask were refluxed with stirring for 4 hours.
After having been cooled, the resultant mixture was charged with benzene and water, and an organic layer formed was collected by sepration, followed by water-washing. The organic layer thus collected was dried over anhydrous sodium sulfate, and the solvent was distilled off under reduced pressure to obtain 23.2 g of the title compound as a pale brown liquid. Purification by centrifugal chromatography over silica gel gave a colourless liquid, nD5 = 1.4898.The chemical shift of nuclear magnetic resonance spectrum as measured (in deuterochloroform) was found to be as follows:
a : 2.95 ppm b : 4.75 ppm c : 1.23ppm Shown below in Table 1 are representative of the compounds of the general formula (I) which have been prepared according to the procedure similar to those as described in the foregoing preparative examples, and a reference number assigned to each compound in Table 1 will be referred as well to the following test examples and working examples.
d R1 S?2 R3 A2 T7 yl 01 z t z ti r. nr rl!) iYr~-i'!drX2.
C113 Cm!3 li 1171 ,p. sst-43nC I I) " " 7' ' nC2117 " " " 1.&num;47149 flCf 1113 " 1.a777 C2"5 21's 1 1.4850 no3117 iiC3117 " riC1ll9 1C4119 w rn.p. 27-29 C " C1130 C113 t 5 n 1.'1721 Dx 1.11'-J?7 tO CuilZ '1 n25 1.1931 fl 1 Cl15 Cll3 " ~l n.p. (IT-s40C 12 p S " clay tI?r)5 1.4 7t91.4719 I " " C"'15 " " 1.47i'2 Cp!l5 11 1.l'1l9 II, " nCjR7 " " " i.s7r,6 37 IC II icy"7 rz, " mp. 7-50 C 17 " aC,,llq " n25 I t.4852 C " " " " 1.1|921s IlCIC-ClI- " - " .4119)' 3 ;0 " ECRptil2- " " " 1.4901 " p,C!12CI12- " " " l.h7U7 t:lE3 ,c- ( if 2- | " " .5012 " " | " " " 1.4932 C;'"', C?!l'). Cpil5 " " 1.4797 C; liS " " 1.4715 C3 7 nCjil7 II " " 1.41317 IC 11 " iC3117 " " ' 1.41133 37 . p " C115'iC112C112- " " " 1.523.4 5 7 nC 3117 " " 1.41122 IC3!l7 " 1.111131 11 IC 11 " ' " " 1.4795 37 S2 iiC11l!9 nC',ll9 " '1 " 1.4788 3 nC!13 nC!13 " " " 1.759 Table 1 (Continued)
::rl Cll2Cl!Cll2- C112=CIICH2~ 11 11,f) n?g35 1.,19or 35 C2lfsOclt2cl{2- C2l!50C112C!l2- " " " 1.4791 Cm 30 3 " 1.4to75 5i C21150 C2!!5 " " 1 1.41133 9 CIIII9O C,,119 " ' ', 1."901 198 Dl " " n.p. 49-61 C " .. n2D5 1.50711 '!!- " 1 1.5104 a? (fi- " " " 1.501 013 /|3 ; " " " 1.5081 C 3 C!!31 " 1.,19A8 '15 CC!!2)11 " " 1.5120 f razz " 1.40112 cl,3 "7 7 t 1; " " " 1. 5003 a cm! 3 C113 " 1 1 S 7 a7 n " Cllj " " 1.41v13 C21i5 II H " " 1.119011 5 " " 0113 " til " 1.411(12 " ;;' " nC3!!7 11 " 1.111330 IC " it3"7 " " 1.111199 nC,,!!9 " " " t.4I't/7 IC,,!! " " 'sU75 6 Cli3 ,,cC4!l9 11 -!3 n%5 1.41)92 57 " " X " 1.4927 11 " nC51111 " " 1.4859 9 '' " 061113 " 1.1111511 ra c'A2-c)lC,I%- " " " 1.4073 61 | " CI12-C-C1l e | 1.50to5 c"3 62 " CII2-CII-CII- " " " 1.50?2 & 13 th3 " C112'CII-CB2C112- " " 1.5053 (DI!- 1.5071 1 -' 01012012 " " " 1.5(151 I v C1130 H2CI " " " 1.41174 r. C2'15 C?!15 " " " t.4lyv8 " " no31!7 " " " 1.411711 í 9 iC3II7 " 1.111177 37 ;0 nC', 119 1.111140 1 " IC11!!9 " " 1.1111110 " r,ncC4!19 9 8 n 1.4711 71 " tC',!!9 " " 1.4907 711 " Cl!1,. (10!'?- " " f " 1.51(15 " ' 4% " " 6 " ClC)12CIIjC}f2 " " " 1.4(107 77 " cii30et2clt2- " 1.111141 ".11 nc3Il7 nC3!!7 3 7 t 1.41143 79 iC I! " " 1.411111 37 110 " nC11!!9 " " 1.4BO4 Table 1 (Continued)
P1 It3117 iCjll7 II n2I > 5 111111 " 2 nC II9 " " " 1.41107 It3 nCII9 " " 1.47117 t2 Cll25CllC}l2- C112.CIIC112- " " 1.5011 '.3 1, 50 02115 ' r s 1.41190 zzi7 t ', " 1.5rio nn " " . " 1.5122 119 ()1 e " 1.51(10 911 " " " 1.50,13 l!3 91 1. " 1.11999 C"3 1.5005 "(3 C113 Cm13 ' " 1.41195 cil3 C2115 11 " " 1.4H3? 5 " it3!!7 " " " 1.41114 02115 C2115 " " 1.41ì45 "7 nC52l7 3 " 1.4819 9n nC4 119 nC4!!9 " ' 1.4705 "J ' 1130 CI13 " 1.4820 1I3 Dl- " .. " 1.5017 (('1 (7N~ " " 1.5or15 " i Q13 C113 ! " 1.4793 ('3 " C2!!5 " e. " 1.11792 P25 1t54 f 1I3 iC.5H7 II l) 1.4795 1(D5 t H5 C2115 " " 1.4820 ". BCj"7 5 7 nO3!!7 " " 47i)9 C.'? IlC ssIIg no4!!9 " 1.4771 I' C;lI50 02115 C2H5 (I ' 1.41163 ; This " Clq " 1.49117 - a- t5092 111 CH3 c3 v} iI3 t.4647 02115 " C2ll5 " " " 1.41135 113 " nC3117 " 1l 1l 1.4793 1111 iC31I7 " " 1.bye2 15 " nC4!!9 " " " 1.4796 ^^' " ClI3Cil-CllCli2 " 1.4903 117 C2115 Cd15 " 1.41113 1111 CH3 " CR 1.4706 4" nC31I7 II " " 1.1,1105 17u IC3!!7 " " 1.41114 ".1 "C3117 neo 11 " " " 1.4,194 37 37 . ;' ' iC3Ii7 " ' ' 1.41101 1.3 IC5II7 " " " " 1.4H00 fl st r C 119 nC4II9 " " 1.4733 t. 5 t H2CllC1l2- C112.CIIC112- ' " " 1.4925 t;* rli3o C1I3 " n I 1.41131 '7 021150 02115 " " " 1.41192 1 11 l Dl " 1.49115 1, ! S8~ " &commat; " 1 5066 Table 1 (0onng
n25 130 0113 Cl!3 11 p n7D5 1.41379 02115 i?i " C.?C{5 " 1.4u'( ^72 " " " 1.41123 133 nC3117 nC3117 " " " 1.4791 tR nO4!!9 1104119 " 1.81795 0113 i5 CH3 C113 CllQ " 1.4B92 cull) < 9 " C2115 " " " 1.41152 137 C2115 " cil5 " 1.4M1 sn 53 3 " -$'7 " 1.41105 \611J 02115 " " " 1.4901 4(1 02115 " " " 1.41152 41 nCjlS "C3117 " " " 1.41102 "; ncf 9 llC43l9 " " " 1.41100 C!! ; S C115 C113 " -ll3( " 1.4811 C2115 " " " 1.4.187 ^h) C2XIS " " " " 1'.r, cm13 (:113 " -H3C112)7 " 1.4itSo 02115 C;,115 " 1 .4!!Pl ".1! Çl Cl13 C113 " -z; it 1.4795 3 3 1 C; 1{5 C,?2l5 " 1 .ws70a 1 it 0113 0113 II " 1.41155 .)1 02115 C2115 " " " 1.41129 15 013 1! Clt3 l! tS 1.51)1),' C4,.1 C;?tt9 C2155 " 1.4(13'? Il Cl13 ' rice " 1.4990 Jg t 5 C?l5 0211,,- " 1.49411 , 0113 1'!', C!! C1{3 " II 1 " 1.411211 cl,3 02115 ' C2il5 " 5 1.4W3 3 5 0113 0113 " y 'lI-Cl 3 " 1.4Uit c,Pg ' cub15 " " " 1.111100 In case where the present compound is used as an active ingredient of herbicide, it may be used as it is or after being dissolved in a suitable solvent.However, it is preferably to use the present compound, as is the case with ordinary herbicides, after formulating into granule, wettable powder or emulsion by the use of various carriers or adjuvants. Furthermore, it is possible to aim at enlarged applications of the present compound by using it in admixture with known herbicides, insecticides, fungicides or plant growth regulatants.
The present invention is illustrated below with reference to some examples, but it should be construed that the scope of the invention is not limited only thereto. In the examples, "part or parts" are by weight.
Example 10 (granule) To a thorough mixture comprising 3 parts of compound No. 39, 15 parts of bentonite, 2 part of sodium dodecylbenzenesulfonate and 80 parts of clay was added 20 parts of water. The resultinssmixture was kneaded with mixing by means of a kneader, formed into pellets through a pelletizer and then dried by means of a fluidized drier to obtain a herbicide containing 3% of the active ingredient.
Example 11 (granule) To a thorough mixture comprising 10 parts of compound No. 53, 15 parts of bentonite, 2 parts of sodium dodecylbenzenesulfonate and 73 parts of clay was added 20 parts of water, and the resulting mixture was kneaded with stirring by means of a kneader, formed into pellets through a pelletizer and then dried by means of a fluidized drier to obtain a herbicide containing 10% of the active agent.
Example 12 (emulsion) Athorough mixture comprising 30 parts of compound No. 11,55 parts ofxylol and 15 parts of Solpol (a trade name of an emulsifier produced and sold by Toho Kagaku Kogyo K.K.) was suitably treated to form an emulsion for herbicide containing 30% of the active ingredient.
Example 13 (wettable powder) A homogeneous mixture comprising 20 parts of compound No. 117, 3 parts of calcium lignosulfonate, 2 parts of polyoxyethylenenonylphenyl ether and 75 parts of white carbon was pulverized to obtain a wettable powder for herbicide containing 20% of the active ingredient.
In order to demonstrate activity of herbicides according to the present invention, some typical test examples are given hereinafter.
Test Example 1 Pre-emergence herbicidal activity of the present compounds on paddy field weeds and phtotoxic test thereof on transplanted paddy rice plants A 1/5000 are Wagner's pot was filled with paddy field soil (alluvial soil), and on the surface layer portion of the soil were sowed 50 grains each of barnyard grass, bulrush, water plantain, monochoria, false pimpernel and toothcup, respectively. One day after seeding, the pot was filled with water to keep the submerging depth of 2 cm. Three days after seedling, three stubs of paddy rice seedlings at 4 leaf stage were transpalted at a rate of two seedling per pot. One day after transplantation, an emulsion prepared according to Example 12 and diluted with water was dropwise applied to the pot at a rate of 10 ml (corresponding to 100 g per 10 ares in terms of amount of the active ingredient) per pot.The test was carried out by repeating the same test two times per area, and 30 days after the treatment with the chemical the herbicidal effect and degree of hytotoxicity to paddy rice were examined based on the following scale of rating. The results obtained are as shown in Table 2.
Herbicidal effect (Degree of phytotoxicity) 5 : Perfect control of weeds (Withering) 4 : Large in herbicidal effect (Large in phytotoxicity) 3 : Medium " (Medium ") 2 : Small " (Small 1 : Slight " (Slight I') 0 . None " (None TABLE 2 Degree of Compound Degree of herbicidal effect phytotoxicity No.Barnyard Bulrush Water Monochoria False Tooth to paddy rice grass plantain pimpernel cup plant 1 5 5 5 5 5 5 0 2 5 5 5 5 5 5 1 3 5 5 5 5 5 5 0 4 5 5 4 5 5 5 0 5 5 5 5 5 5 5 1 6 5 5 5 5 5 5 0 7 4 5 4 5 5 5 0 8 5 5 5 5 5 5 0 9 5 5 5 5 5 5 0 10 5 5 5 5 5 5 0 11 5 5 5 5 5 5 50 12 4 5 4 4 5 5 0 13 4 4 4 4 5 5 b 14 5 5 5 5 5 5 0 15 5 5 5 5 5 5 0 16 5 5 5 5 5 5 0 17 5 5 5 5 5 5 0 18 5 5 5 5 5 5 0 19 5 5 5 5 5 5 0 20 5 5 5 5 5 5 1 21 4 5 4 4 5 5 0 TABLE 2 (cont...) 22 4 4 3 4 5 5 0 23 5 5 5 5 5 5 0 24 5 5 5 5 5 5 1 25 3 4 3 3 5 5 0 26 5 5 5 5 5 5 0 27 5 5 5 5 5 5 0 28 4 5 4 4 5 5 0 29 5 5 5 5 5 5 0 30 5 5 5 5 5 5 0 31 5 5 5 5 5 5 0 32 5 5 5 4 5 5 0 33 4 4 3 3 5 5 0 34 5 5 5 5 5 5 0 35 4 4 4 3 5 4 0 36 5 5 5 5 5 5 0 37 5 5 5 5 5 5 1 38 4 4 4 4 5 4 0 39 5 5 5 5 5 5 0 40 5 5 5 5 5 5 0 41 4 5 4 4 5 5 0 42 5 5 5 5 5 5 0 43 5 5 5 5 5 5 0 44 5 5 5 5 5 5 0 45 4 4 4 4 5 4 0 46 4 4 3 3 4 3 0 47 4 4 4 3 4 4 0 48 5 5 5 5 5 5 0 49 3 4 3 4 4 4 0 50 5 5 5 5 5 5 1 51 3 4 4 4 5 4 0 52 5 5 5 5 5 5 0 53 5 5 5 5 5 5 0 54 4 5 4 5 5 4 0 55 5 5 5 5 5 5 0 56 5 5 5 5 5 5 0 57 5 5 5 5 5 5 0 58 4 5 4 5 5 5 0 59 4 4 4 4 5 4 0 60 5 5 5 5 5 5 1 61 4 5 4 4 5 4 0 62 4 4 4 4 5 4 0 63 5 5 5 5 5 5 0 64 5 5 5 5 5 5 0 65 5 5 5 5 5 5 1 66 4 5 4 5 5 4 0 67 5 5 5 5 5 5 1 68 5 5 5 5 5 5 0 69 5 5 5 5 5 5 1 70 5 5 4 4 5 5 0 71 5 5 5 5 5 5 '0 72 5 5 5 5 5 5 0 73 5 5 4 5 5 5 1 74 5 5 5 5 5 5 1 75 5 5 4 5 5 4 0 76 4 4 3 5 5 4 0 77 5 5 5 5 5 5 0 78 5 5 5 5 5 5 0 79 5 5 5 5 5 5 0 TABLE 2 (cont...) 80 4 5 4 5 5 4 0 81 5 5 5 5 5 5 1 82 4 4 4 4 4 4 0 83 5 5 5 5 5 4 1 84 5 5 5 5 5 5 0 85 5 5 5 5 5 5 1 86 5 5 5 5 5 5 0 87 5 5 5 5 5 5 0 88 5 5 5 5 5 5 0 89 4 4 4 3 4 4 0 90 5 5 4 5 4 5 0 91 4 5 4 5 4 5 0 92 5 5 5 5 5 5 0 93 5 5 5 5 5 5 0 94 5 5 5 5 5 5 1 95 5 5 5 5 5 5 1 96 5 5 5 5 5 5 1 97 5 5 5 5 5 5 0 98 4 5 5 5 5 5 0 99 5 5 5 5 5 5 1 100 5 5 5 5 5 5 0 101 5 5 5 5 5 5 0 102 5 5 5 5 5 5 1 103 5 5 5 5 5 5 1 104 5 5 5 5 5 5 1 105 5 5 5 5 5 5 1 106 5 5 5 5 5 5 0 107 4 5 4 5 5 5 0 108 5 5 5 5 5 5 1 109 5 5 5 5 5 5 1 110 5 5 5 4 5 4 0 111 5 5 5 5 5 5 0 112 5 5 5 5 5 5 0 113 5 5 5 5 5 5 0 114 5 5 5 5 5 5 1 115 5 5 4 4 5 4 0 116 4 4 4 4 5 4 0 117 4 4 3 4 4 3 0 118 5 5 5 5 5 5 0 119 5 5 5 5 5 5 0 120 5 5 5 5 5 5 0 121 5 5 5 5 5 5 0 122 5 5 5 5 5 5 0 123 5 5 5 5 5 5 0 124 4 5 4 5 5 4 0 125 5 5 5 5 5 5 1 126 5 5 5 5 5 5 0 127 5 5 5 5 5 5 1 128 5 5 5 5 5 5 0 129 5 5 5 5 5 5 X 0 130 5 5 5 5 5 5 0 131 5 5 5 5 5 5 1 132 5 5 5 5 5 5 1 133 5 5 5 5 5 5 0 134 4 4 4 4 5 4 0 135 5 5 5 5 5 5 1 136 5 5 5 5 5 5 1 137 5 5 5 5 5 5 1 TABLE 2 (cont...) 138 5 5 5 5 5 5 0 139 5 5 5 5 5 5 1 140 5 5 5 5 5 5 1 141 5 5 4 5 5 4 0 142 4 4 4 4 5 4 0 143 5 5 5 5 5 5 0 144 4 5 5 5 5 5 0 145 4 5 4 5 5 5 0 146 4 4 4 4 4 4 0 147 5 4 4 4 5 4 0 148 4 4 4 4 5 4 0 149 5 4 3 4 5 3 0 150 4 4 3 4 4 3 0 151 4 4 4 4 4 4 0 152 4 5 4 4 5 4 0 153 4 4 4 4 5 4 0 154 4 4 3 4 4 3 0 155 4 4 4 4 5 4 0 156 4 4 4 4 5 4 0 157 4 4 3 4 4 4 0 158 5 5 4 5 5 4 0 159 5 5 4 4 5 4 0 Comparative chemical 3 3 1 4 4 2 3 " 2 0 0 0 0 1 0 0 " 3 5 5 4 4 4 4 3 " 4 1 1 0 0 0 0 0 Untreated area 0 0 0 0 0 0 0 In the above table, comparative chemicals 1,2,3 and 4 are emulsions prepared according to example 12 and respectively containing O-(methylaminosulfonyl)-glycolic acid hexamethyleneamide (a compound disclosed in Japanese Pre-Exam. Publn. No.20331/1974, O-(aminosulfonyl)-glycolic acid hexamethyleneamide (a compound disclosed in Japanese Pre-Exam. No. 20331/1974), 2-chlorn-2',6'-diethyl-N- (butoxymethyl)acetanilide, and S-ethylhexahydro-1 H-azepin-1 -carbothioate, and these compounds were used in the same treatment procedure and concentration as in the case of the present compounds.
Test Example 2 Growth stage herbidical effect on paddy field weeds and phytotoxic test to paddy rice plant A 1/5000 are Wagner's pot was filled with paddy field soil (alluvial soil), and on the surface layer portion of the soil were uniformly sowed 50 grains each of barnyard grass, bulrush, water plantain and monochoria, respectively. One day after seeding, the pot was filled with water to keep the submerging depth of 2 cm.
Three days after seeding, three stubs paddy rice seedling at 2.5 leaf stage were transplanted at a rate of two seedlings per stub per pot. An emulsion prepared according to Example 12 and diluted with water was dropwise applied to the pot at a rate of 10 ml (corresponding to 150 g per 10 ares in terms of amount of the active ingredient) per pot, the application of said emulsion having been made 15 days after transplantation, i.e. the growth stage of weeds (barnyard grass at 2.5 leaf stage, bulrush at 2.5 leaf stage, water plantain at 2-3 leaf state, and monochoria at 2 leaf stage). The test was carried out by repeating the same test two times per area, and 30 days after the treatment with the chemical the results were examined based on the same scale of rating as in Test Example 1. The results obtained are as shown in Table 3.
TABLE 3 Degree of Compound Degree of herbicidal effect phytotoxicity No. Barnyard Bulrush Monochoria Water to paddy rice grass plantain plant 1 5 5 5 5 0 2 5 5 5 5 0 5 5 5 5 5 1 8 5 5 5 5 1 9 5 5 4 5 0 11 5 5 5 5 0 14 5 5 5 5 0 16 5 5 5 5 0 18 4 5 4 5 0 19 4 5 4 4 0 20 5 5 5 5 1 21 4 5 3 4 0 22 4 4 4 4 0 23 5 5 5 5 0 24 5 5 5 5 1 25 4 4 3 4 0 27 5 5 5 5 0 28 3 5 3 4 0 29 5 5 5 5 0 31 5 5 5 5 0 33 4 4 3 4 0 34 4 5 3 5 0 35 4 4 3 4 0 36 5 5 5 5 1 37 5 5 5 5 0 38 4 5 4 4 0 39 5 5 5 5 0 41 4 4 4 5 0 45 4 5 3 4 0 46 4 4 3 4 0 48 5 5 5 5 0 49 3 4 3 4 0 53 5 5 5 5 0 55 5 5 5 5 0 57 5 5 5 5 1 60 4 4 4 5 0 61 4 4 3 4 0 62 3 4 3 4 0 63 5 5 5 5 0 64 5 5 5 5 0 67 5 5 5 5 1 72 5 5 4 5 0 76 4 4 3 4 0 77 4 4 4 4 0 79 5 5 5 5 0 85 5 5 5 5 0 86 5 5 5 5 0 87 5 5 5 5 0 88 5 5 5 5 0 92 4 5 4 5 b 93 5 5 5 5 0 95 5 5 5 5 1 96 5 5 5 5 1 102 5 5 5 5 0 103 5 5 5 5 1 105 5 5 5 5 1 111 5 5 5 5 1 112 5 5 5 5 0 TABLE 3 (cont...) 114 5 5 5 5 0 117 5 5 5 5 1 121 5 5 4 5 0 122 5 5 4 5 0 123 4 5 4 5 0 124 5 4 4 4 0 126 4 4 3 4 0 127 5 5 5 5 0 128 5 5 5 5 0 129 5 5 4 5 0 130 5 5 5 5 0 137 5 5 4 5 0 139 4 5 4 5 0 145 4 4 3 4 0 146 4 4 4 4 0 149 5 4 4 5 0 151 4 4 3 4 0 152 4 4 4 4 0 159 4 5 4 4 0 Comparative chemicall 3 3 2 4 2 2 0 0 0 0 0 " 3 1 3 0 1 1 4 4 4 3 0 0 0 Untreated area 0 0 0 0 0 In the above table, comparative chemicals 1-4 were the same in Test Example 1 and used in the same treatment procedure and concentration as employed in Test Example 1.
Test Example 3 Pre-emergence herbicidal effect on farmland weeds and phytotoxic test to crops The test for herbicidal effect on weeds was conducted in the following manner. That is, a 1/5000 are unglazed porcelain pot was filled with farmland soil (alluvial soil), and the surface soil of a 1 cm depth was homogeneously mixed with 30, 100, 50, 50 and 30 rains of crab-grass, chickweed, common purslane, lambsquater and Echinochloa oryzicola, respectively, followed by softly pressing the surface layer downward. Two days after seeding, an emulsion prepared according to Example 12 and diluted with water was sprayed over the soil surface of the pot at a rate of 100 1. of the treating chemical liquid (corresponding to 50 g per 10 ares in terms of amount of the active ingredient).The test was carried out by repeating the same test two times per area, and 30 days after the treatment with the chemical the herbicidal effect obtained was examined based on the same scale of rating as in Example 1.
The phytotoxic test on crops was conducted in the following manner. That is, a 1/10000 are unglazed porcelain pot was filled with farmland soil (alluvial soil), and seeds of crops (5 grains of soybean, 10 grains of radish, 10 grains of wheat, 10 grains of beet and 5 grains of corn) were individually sowed in separate pots, followed by softly pressing the soil surface downward. One day after seeding, an emulsion prepared according to Example 12 and diluted with water was sprayed over the soil surface at a rate of 100 1.
(corresponding to 50 g of amount of the chemical interms of the active ingredient) per 10 ares. The test was carried out by repeating the same test two times per area, and 30 days after the treatment with the chemical the phytotoxicity to the crops was examined based on the same scale of rating as in Example 1. The results obtained are as shown in Table 4.
TABLE 4 Degree of herbicidal effect Degree of phytotoxicity Compound on farmland weeds to crops No.
Crab- Chickweed Common Lambsquater Amaranth SoybeanRadish Wheat Beet Corn grass purslane 1 5 5 4 5 4 0 1 0 0 0 2 5 5 5 5 4 0 1 0 1 0 5 5 5 4 5 5 0 2 0 1 0 8 5 5 5 4 4 0 1 0 0 0 9 5 5 5 4 5 0 0 0 0 0 11 5 5 5 5 5 0 0 0 0 0 14 5 5 4 5 5 0 1 0 1 0 16 5 5 5 5 5 0 1 0 0 0 18 4 5 4 5 4 0 1 0 0 0 19 4 4 4 4 3 0 0 0 0 0 20 5 4 4 5 4 0 2 0 1 0 21 3 4 4 4 3 0 0 0 0 0 22 4 4 4 4 4 0 0 0 0 0 23 5 5 4 5 4 0 0 0 0 0 24 5 5 5 5 5 0 2 1 1 0 25 3 4 4 3 3 0 0 0 0 0 27 5 5 4 4 4 0 1 0 0 0 28 4 4 4 3 3 0 0 0 0 0 29 5 4 4 5 4 0 0 0 0 0 31 5 5 5 5 5 0 1 1 1 0 33 4 4 3 4 3 0 0 0 0 0 34 5 5 4 5 5 0 1 1 1 0 35 4 4 3 4 3 0 0 0 0 0 36 5 5 5 5 5 0 1 0 0 0 37 5 5 5 5 4 0 1 0 0 0 38 4 4 4 4 3 0 0 0 0 0 TABLE4(cont...) 39 5 5 5 5 5 0 0 0 0 0 41 4 5 5 5 4 0 0 0 0 0 45 4 4 3 4 3 0 0 0 0 0 46 4 4 3 4 4 0 0 0 0 0 48 5 5 5 5 5 0 0 0 0 0 49 3 4 4 4 3 0 0 0 0 0 53 5 5 5 5 5 0 1 0 0 0 55 5 5 4 5 5 0 1 0 0 0 57 5 4 4 4 4 0 1 1 1 0 60 4 5 5 5 4 0 1 0 0 0 61 4 4 4 4 3 0 0 0 0 0 62 4 4 4 4 3 0 0 0 0 0 63 5 4 4 5 4 0 0 0 0 0 64 5 5 4 5 3 0 0 0 0 0 67 5 5 5 5 5 0 1 0 1 1 72 5 5 4 5 4 0 1 0 0 0 76 4 5 4 4 3 0 1 0 0 0 77 4 4 4 4 3 0 0 0 0 0 79 5 5 4 4 4 0 0 0 0 0 85 5 5 5 5 5 0 1 0 0 0 86 5 5 5 5 4 0 1 0 0 0 87 5 5 5 5 5 0 0 0 0 0 88 5 5 5 5 5 0 0 0 0 0 92 5 5 4 5 4 0 1 0 0 0 93 5 5 5 5 5 0 1 0 1 1 TABLE4(Cont...) 95 5 5 5 5 5 0 1 1 1 0 96 5 5 5 5 5 0 1 0 1 1 102 5 5 5 5 5 0 1 0 1 0 103 5 5 5 5 5 0 1 0 0 0 105 5 5 5 5 5 0 1 0 0 0 111 5 5 5 5 5 0 2 0 1 1 112 5 5 5 5 5 0 1 0 1 0 114 5 5 5 5 5 0 1 0 1 0 117 5 5 5 5 5 0 2 0 1 0 121 5 5 5 5 5 0 1 0 1 0 122 5 5 5 5 5 0 1 0 0 0 123 5 5 5 5 5 0 0 0 0 0 124 4 5 4 5 4 0 0 0 0 0 126 5 5 5 5 5 0 1 0 1 0 127 5 5 5 5 5 0 1 0 0 0 128 5 5 5 5 5 0 0 0 0 0 129 5 5 5 5 4 0 0 0 0 0 130 5 5 5 5 5 0 0 0 0 0 137 5 5 5 5 5 0 0 0 0 0 139 5 5 5 5 4 0 0 0 0 0 145 4 5 4 5 4 0 0 0 0 0 146 4 5 4 4 4 0 0 0 0 0 149 5 5 4 5 4 0 0 0 0 0 151 4 5 4 4 3 0 0 0 0 0 152 5 4 4 4 4 0 0 0 0 0 159 5 4 5 4 4 0 0 0 0 0 Comparative chemica1 4 3 3 3 2 1 2 1 2 1 " 2 1 1 0 1 0 1 2 0 0 0 " 3 5 4 4 5 5 4 5 3 5 1 " 4 5 4 4 5 5 2 1 2 3 3 Untreated area 0 0 0 0 0 0 0 0 0 0 " In the above table, comparative chemicals 1 and 2 were the same as the comparative chemicals 1 and 2 used in Test Example 1, and comparative chemical 3 represents a commercially available wettable powder containing 2-chloro-4,6-bis(ethylamino)-S-triazine, and comparative chemical 4 a commercially available emulsion containing atata-trifluoro-2,6-dinitro-N,N-dipropyl-para-toluidine. The treatment procedure and concentration adopted for these comparative chemicals were the same as in the case of the present compounds.
Test Example 4 Growth stage herbicidal effect on farmland weeds and phytotoxic test to crops The test for herbicidal effect on weeds was conducted in the following manner. That is, a 1/5000 are unglazed porcelain pot was filled with farmland soil (alluvial soil), and 100, 50, 50 and 30 grains of seeds of crab-grass, chichweed, common purslane, lambsquater and amaranth, respectively, were sowed and the soil surface was softly pressed downward.An emulsion prepared according to Example 12 and diluted with water was sprayed over stem and leaf portions of the weeds at a rate of 100 1. of the treating chemical liquid (corresponding to 200 g per 10 ares in terms of amount of the active ingredient) per pot at the time when the weeds germinated and grown to reach 4 leaf stage in crab-grass, 3 leaf stage in chickweed, 2 leaf stage in common purslane, 1.5 leaf stage in pigweed and 2.5 leaf stage amaranth. The test was carried out by repeating the same test two times per area, and 20 days after the treatment with the chemical the herbicidal effect was examined based on the same scale of rating as in Test Example 1.
The phytotoxic test to the crops was conducted in the following manner. That is, a 1/10000 are unglazed porcelain pot was filled with farmland soil (alluvial soil), and 5, 10, 10, 10 and 5 grains of seeds of soybean, radish, wheat, beet and corn, respectively, were sowed in separate pots, and the surface layer of the soil was softly pressed downward. An emulsion prepared according to Example 12 and diluted with water was sprayed over stem and leaf portions of the crops at a rate of 100 1. of the treating chemical liquid (corresponding to 200 g per 10 ares in terms of amount of the active ingredient) per pot at the time when crops germinated and grown to 2 to 3 leaf stage.The test was carried out by repeating the same test two times per area, and 20 days after the treatment with the chemical the phytotoxicity to the crops was examined based on the same scale of rating as in Test Example 1. The results obtained are as shown in Table 5.
TABLE 5 Degree of herbicidal effect Degree of phytotoxicity Compound on farmland weeds to crops No.
Crab- Chickweed Common grass purslane Lambsquater Amaranth Soybean Radish Wheat Beet Corn 1 5 5 4 5 4 0 2 0 1 0 2 5 5 5 5 4 0 1 0 1 0 5 5 5 4 5 5 0 2 0 1 1 8 5 5 5 5 4 0 1 0 1 0 9 5 5 4 5 4 0 1 0 0 1 11 5 5 5 5 5 0 1 0 0 0 14 5 5 5 5 5 0 1 0 0 0 16 5 5 5 5 5 0 0 0 0 0 18 4 4 3 4 3 0 1 0 1 0 19 4 3 3 4 3 1 1 0 1 0 20 5 5 5 5 5 1 2 1 1 1 21 4 3 3 3 3 0 0 0 0 0 22 4 3 3 4 3 0 1 0 0 0 23 5 5 5 5 4 0 1 0 1 0 24 5 5 5 5 5 1 2 0 1 1 25 3 4 3 4 3 0 0 0 0 0 27 5 5 4 5 4 0 1 0 1 1 28 4 4 3 3 3 0 0 0 0 0 29 5 4 4 4 3 0 0 0 0 0 31 5 5 4 4 4 0 1 0 0 0 33 4 4 3 5 3 0 1 0 0 1 34 4 4 4 4 3 0 1 1 0 0 35 4 3 3 4 3 0 0 0 0 0 36 5 5 5 5 5 0 1 0 1 1 37 5 5 5 5 4 0 1 0 1 1 38 4 4 3 4 3 0 0 0 0 0 TABLE5(Cont...) 39 5 5 5 5 5 0 1 0 0 0 41 4 4 3 4 3 0 0 0 0 0 45 4 4 3 4 4 0 0 0 0 0 46 4 4 3 3 3 0 0 0 0 0 48 5 5 5 5 5 0 1 0 1 0 49 3 3 2 4 2 0 0 0 0 0 53 5 5 5 5 5 0 1 1 1 1 55 5 5 5 5 5 0 2 1 1 1 57 5 5 5 5 4 1 2 1 1 1 60 4 4 3 4 4 0 0 0 0 0 61 4 3 3 3 3 0 0 0 0 0 62 3 4 3 4 3 0 0 0 0 0 63 5 5 4 4 4 0 1 0 0 0 64 5 5 4 5 4 0 1 0 1 0 67 5 5 5 5 5 1 2 1 1 0 72 4 5 4 4 3 0 1 0 1 0 76 4 4 3 4 3 0 0 0 0 0 77 4 3 3 3 3 0 0 0 0 0 79 4 5 4 4 3 0 0 0 0 0 85 5 5 5 5 5 0 1 0 0 1 86 5 5 4 5 4 0 1 0 0 0 87 5 5 5 5 5 0 1 0 1 1 88 5 5 4 5 4 0 1 0 0 0 92 4 4 3 4 4 0 0 0 0 0 93 5 5 5 5 5 1 2 1 1 1 95 5 5 5 5 4 0 2 0 1 1 96 5 5 5 5 5 1 2 1 1 1 102 5 5 5 5 5 0 2 1 1 1 103 5 5 5 5 5 0 1 1 1 1 105 5 5 5 5 5 0 2 1 1 0 TABLE5(Cont...) 111 5 5 5 5 5 1 2 1 1 1 112 5 5 5 5 5 0 2 0 1 1 114 5 5 5 5 5 0 1 1 1 1 117 5 5 5 5 5 0 2 1 1 0 121 4 5 4 4 4 0 1 0 0 0 122 4 4 4 5 3 0 0 0 0 0 123 4 5 4 5 4 0 1 0 1 0 124 4 4 3 4 3 0 0 0 0 0 126 5 5 5 5 5 0 1 0 1 0 127 5 5 5 5 4 0 1 0 0 1 128 5 5 5 5 5 0 2 0 1 0 129 5 5 4 5 4 0 1 0 0 0 130 5 5 5 5 5 0 1 0 0 0 137 5 5 4 4 4 0 1 0 0 1 139 5 5 4 4 3 0 0 0 0 0 145 4 4 4 4 3 0 0 0 0 0 146 4 4 3 3 3 0 0 0 0 0 149 5 5 4 5 4 0 1 0 1 0 151 4 4 3 3 3 0 0 0 0 0 152 4 5 4 4 3 0 0 0 0 0 159 4 4 4 4 3 0 0 0 0 0 Comparative chemica1 3 3 2 3 1 1 3 1 2 2 " 2 0 0 0 0 0 0 1 0 0 0 " 3 5 5 5 5 4 5 5 4 5 4 " 4 0 4 5 5 4 4 3 0 0 4 Untreated area 0 0 0 0 0 0 0 0 0 0 In the above table, comparative chemicals 1 and 2 were the same as the comparative chemicals 1 and 2 used in Test Example 1, comparative chemical 3 was a commercially available emulsion containing 1,1 '-dimethyl-4,4'-bipyiridium dichloride, and comparative chemical 4 was a commercially available wettable powder containing 3-isopropyl-2,1,3-benzothiadiazinone-(4)-2,2-dioxide. The treatment procedure and concentration adopted for these comparative chemicals were the same as in the case of the present compounds.

Claims (1)

1. An O-sulfamoylglycolic acid amide derivative represented by the general formula
wherein R1 and R2, which may be the same or different, each represent a substituted or unbsubsituted alkyl, alkenyl, alkynyl, cycloalkyl or alkoxy group which may be substituted with a halogen atom, an alkoxy or alkylthio group, or R1 and R2 may form in cooperation with each other a heterocyclic ring which may be substituted with a lower alkyl group, F3 represents a hydrogen atom or a lower alkyl group, and represents a monocyclic or bicyclic ring which may be substituted with a
lower alkyl group.
2. An O-sulfamoylglycolic'acid amide derivative according to claim 1 in which R1 and R2 have 1 to 6 carbon atoms.
3. An O-sulfamoylglycolic acid amide derivative according to claim 1 in which at least one of R1, R2 and F3 is a radical specifically identified herein.
4. An O-sulfamoylglycolic acid amide derivative according to claim 1 specifically identified herein.
5. A herbicidal composition comprising as its active ingredient an O-sulfamoylglycolic acid amide derivative as claimed in any one of claims 1 to 4 together with a diluent or carrier.
6. A composition according to claim 5 substantially as hereinbefore described.
7. A method of controlling weeds which comprises applying to the weeds or to an area likely to be infested with weeds a composition as claimed in claim 5 or 6.
New claims or amendments to claims filed on 31 March 1980 Superseded claim 1 New or amended claims:
1. An O-sulfamoylglycolic acid amide derivative represented by the general formula
wherein R1 and R2, which may be the same or different, each represent a saturated or unsaturated alkyl, cycloalkyl or alkoxy group which may be substituted with a halogen atom, an alkoxy or alkylthio group, or R1 and R@ may form in cooperation with each other a heterocyclic ring which may be substituted with a lower alkvl group, R3 represents a hydrogen atom or a lower alkyl group, and
represents a monocyclic or Bicyclic nng which may oe @ substituted win a lower ainyi yluulJ.
GB7944535A 1978-12-28 1979-12-28 O-sulfamoylglycolic acid amide derivatives Expired GB2038334B (en)

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Application Number Priority Date Filing Date Title
JP16579778A JPS5592366A (en) 1978-12-28 1978-12-28 O-sulfamoylglycolic acid amide derivative

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Publication Number Publication Date
GB2038334A true GB2038334A (en) 1980-07-23
GB2038334B GB2038334B (en) 1983-05-05

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Application Number Title Priority Date Filing Date
GB7944535A Expired GB2038334B (en) 1978-12-28 1979-12-28 O-sulfamoylglycolic acid amide derivatives

Country Status (8)

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JP (1) JPS5592366A (en)
BR (1) BR7908645A (en)
DE (1) DE2952483C2 (en)
ES (1) ES487249A0 (en)
FR (1) FR2445317A1 (en)
GB (1) GB2038334B (en)
IT (1) IT1126799B (en)
NL (1) NL7909358A (en)

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2003097589A1 (en) * 2002-05-16 2003-11-27 Basf Aktiengesellschaft Method for the production of sulphamic acid halogenides
CN113764728A (en) * 2020-06-01 2021-12-07 比亚迪股份有限公司 Electrolyte and lithium metal battery

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPS62223494A (en) * 1986-03-21 1987-10-01 Uingu:Kk Cold air fan

Family Cites Families (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
GB1081471A (en) * 1963-09-13 1967-08-31 Stauffer Chemical Co Glycol amide derivatives and use thereof in controlling weed growth
BE794013A (en) * 1972-01-13 1973-07-12 Basf Ag O- (AMINOSULFONYL) -GLYCOLIC ACID ANILIDES SUBSTITUTES
DE2219923C3 (en) * 1972-04-22 1979-07-05 Basf Ag, 6700 Ludwigshafen Substituted O- [aminosulfonyl] glycolic acid amides
DE2310757A1 (en) * 1973-03-03 1974-09-12 Basf Ag SUBSTITUTED O- (AMINOSULFONYL) GLYCOLIC ANILIDES
DE2351608A1 (en) * 1973-10-15 1975-04-24 Basf Ag SUBSTITUTED O- (DIALKYLAMINOSULFONYL) -GLYCOLIC ANILIDES
DE2417764A1 (en) * 1974-04-11 1975-10-30 Basf Ag O-AMINOSULFONYL GLYCOLIC ANILIDES

Cited By (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2003097589A1 (en) * 2002-05-16 2003-11-27 Basf Aktiengesellschaft Method for the production of sulphamic acid halogenides
US7232926B2 (en) 2002-05-16 2007-06-19 Basf Aktiengesellschaft Method for the production of sulphamic acid halogenides
CN113764728A (en) * 2020-06-01 2021-12-07 比亚迪股份有限公司 Electrolyte and lithium metal battery
CN113764728B (en) * 2020-06-01 2023-11-14 比亚迪股份有限公司 Electrolyte and lithium metal battery

Also Published As

Publication number Publication date
FR2445317A1 (en) 1980-07-25
IT7969504A0 (en) 1979-12-28
ES8107183A1 (en) 1980-12-01
GB2038334B (en) 1983-05-05
ES487249A0 (en) 1980-12-01
IT1126799B (en) 1986-05-21
BR7908645A (en) 1980-09-23
NL7909358A (en) 1980-07-01
FR2445317B1 (en) 1983-06-10
JPS5592366A (en) 1980-07-12
DE2952483C2 (en) 1983-06-23
DE2952483A1 (en) 1980-07-31
JPS611020B2 (en) 1986-01-13

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