IL94727A - Triazine derivative and a herbicidal composition comprising the same as an effective ingredient - Google Patents

Description

A TRIAZINE DERIVATIVE AND A HERBICIDAL COMPOSITION COMPRISING THE SAME AS AN EFFECTIVE INGREDIENT S C The present invention relates to a novel triazine vative represented by the general formula R 1 C C X In and h deno J which denotes a methyl trifluoro ethyl methoxy group or fluorine atom and n denotes an integer of 0 ro denotes a halogen atom and R denotes a methyl group or an ethyl as well as a herbicide taining the triazine derivative represented by the general formula as an effective Field of Technology The present invention relates to novel triazine derivatives and a herbicidal composition containing the derivatives as an effective Background technology A variety of herbicides have been hitherto developed and contributed to the productivity and in certain kinds of herbicides have been used over so long years that population of troublesome weeds withstanding them are increasing so that appearance is desired of a herbicids having a broad herbicidal spectrum and effectiveness also against these troublesome It is also desired to develop a herbicide in order to overcome the problem of environmental pollution by conventional In order to overcome to the problem of the ununiform germination of weeds over a long period of appearance is also awaited of a herbicide exhibiting excellent persistent effectiveness and having a versatility of treatment to exhibit effectiveness even by treatment over a wide range of period from the stage to the growing period of 1 The inventors have continued investigations to develop a herbicide capable of exhibiting an excellent herbicidal effect against various kinds of annual and perennial weeds without causing phototoxicity to paddy rice and arrived at a discovery that a herbicide containing a triazine compound as an effective ingredient is effective tion of Japanese Patent official publication of Japanese Patent Kokai official publication of Japanese Patent Kokai and official publication of Japanese Patent Kokai This herbicide is highly active against troublesome weeds in paddy rice field at low dosage without phytotoxicity to paddy rice This herbicide also show excellent herbicidal activity against troublesome weeds by foliage application in upland field without phytotoxicity to Gramineous this herbicide shows somewhat limited performance by preemergence treatment to the soil in upland fields Disclosure of the invention The present invention a triazine derivative represented by the general formula 2 in the A denotes which 2 and which can be of the same kind or different ach denote a methyl group or a methoxy or which denotes a methyl methoxy group or fluorine atom and n denotes an integer of 0 to denotes a halogen atom and denotes a methyl group or an ethyl and a herbicide as an effective a triazine derivative represented by the general formula the for which Y and which can be of the same kind or different each 3 denote a methyl group or a methoxy 2 which denotes a methyl trifluoromethyl methoxy group or fluorine atom and n denotes an integer of 0 to 1 denotes a halogen atom and denotes a methyl group or an ethyl The inventors have continued investigations to search a compound free from phytotoxicity to the crops of the family of Gramineae in upland fields capable of exhibiting a high herbicidal effect against troublesome weeds both in the treatment to soil and in the treatment to foliage with an excellent effect of soil treatment in paddy As a a discovery has been reached that those having a specific haloalkyl group are effective leading to completion of the present The triazine derivative of the present invention is a novel compound and can be effectively utilized as a When used as a herbicide for upland the herbicide of the present invention containing the triazine derivative as an effective ingredient can be used over a long term for appropriate chemical treatment as compared with existing herbicides for upland fields and exhibits a high activity against troublesome weeds both in the soil treatment before germination and in the course of germination of the weeds and in the foliage treatment during the growth period of the weeds still without phytotoxicity to In a remarkably high effect is obtained by the soil 4 treatment or treatment to foliage in fields of crops belonging to Gramineous As compared existing herbicides for paddy in the herbicide of the present invention has a high chemical effect against hardly eliminable weeds still with little Best mode to practice the invention The present invention provides a triazine derivative represented by the general formula the form n which and which can be of the same kind or of differnet kinds each denote a or a or which denotes a methyl tri luoromethyl methoxy group or fluorine atom and n denotes an integer of 0 to denotes a halogen atom and R1 denotes a methyl group or an ethyl and also provides a herbicide containing the triazine derivative represented by 5 the above given general formula The triazine derivative of the present invention sented by the above given general formula can be prepared by various different The method of preparation with the highest efficiency among them is the method to react an alkyl amine salt represented by the general formula CH3 A CH the A is the same as given above and X3 denotes a halogen and cyanoguanidine expressed by the formula NH N H2N C NH CN to prepare an alkyl biguanide salt represented by the general formula CH3 NH NH II II A CH NHCNHCNH 2 the A and X3 are each the same as given and then to react the alkyl biguanide salt with an alkyl ester represented by the general formula CH3 C COOR2 the R1 and x 1 are each the same as given above and R2 denotes an alkyl group having 1 to 4 carbon In this the alkyl amine salt represented by the general formula and cyanoguanidine are reacted to give the alkyl biguanide represented by the general formula which 6 is reacted with the alkyl ester represented by the general formula to give the desired triazine derivative sented by the general formula in high In conducting the reaction between the alkyl amine salt represented by the above given general formula and guanidine these two compounds can be used in an ximately equimolar proportion and usable solvents include cyclic hydrocarbons such as alkyl naphthalenes and the like and chlorinated hydrocarbons such as carbon ethylene chlorobenzene trichlorobenzene and the the reaction temperature is not particularly limitative and sufficient proceeding can be obtained in the range from low to high temperatures in from 80 to The salt of an alkyl biguanide derivative represented by the general formula is obtained by this reaction in the method of the present this is reacted with CH3 the alkyl ester of the general formula C COOR2 to x 1 prepare the desired triazine derivative represented by the general formula This reaction usually proceeds in high efficiency at about 10 to in the presence of a catalyst such as a base and the like in a solvent such as isopropanol and the various kinds of aliphatic various kinds of 7 various kinds of cyclic chlorinated hydrocarbons and the The triazine derivatives of the general formula tained by the above described method are each a novel the compound of the present invention has optical isomers and is obtained usually as a racemic modification while it is possible to obtain the respective antipodes by a known method such as asymmetric The compound of the sent invention can be used as a herbicide either in the form of the racemic modification or in the form of the isolated optical the compound of the present vention also can be used as a herbicide in the form of a salt of an inorganic acid or organic the triazine derivative represented by the general formula inhibited germination and growth of weeds and has high selectivity so that it is satisfactory as a In it is useful not only for the soil ment before the germination of weeds as a matter of course but also for the foliage treatment to the growing weeds to have a versatility of the chemical The triazine derivative of the present invention exhibits no phytotoxicity to the crops belonging to Gramineous crops such as grain oat and the like as the important crops in upland fields and exhibits a prominent herbicidal effect against strongly troublesome broadleaf weeds such as Cassia obtusifolia Ipomoea Abutilon 8 Galium sparium Stellaria Veronica Polygonum Viola Brassica Amaranthus Common blackjack and the like and strongly harmful weeds belonging to the family of such as Digitaria Alopecurus myosuroides and the this triazine derivative not only exhibits a prominent herbicidal effect against broadleaf weeds such as Rotala indica Koehne uligirosa Lindernia pyxidaria Monochorea vaginalis plantaginea and the weeds belonging to the family of Cyperaceae such as Cyperus and the and weeds belonging to the family of Gramineae such as Echinochloa formosensis Ohwi and the but also exhibits a prominent herbicidal effect against perennial weeds such as Scirpus juncoides Hotarui Ohwi Cyperus serotinus Sagittaria pygmaea and the which are currently deemed to be hardly without causing chemical damages against paddy In the next the herbicide of the present invention contains the above described compound the triazine derivative represented by the general formula as the tive ingredient and these compounds can be used as being pared in the preparation form such as solution and the like by mixing with a liquid carrier such as solvents and 9 the like or a solid carrier such as mineral fine powders and the In the preparation of the it is optional according to need to add an emulsifying dispersion spreading suspending penetrating stabilizer and other When the herbicide of the present invention is used in the form of a a composition to be used is prepared by compounding from 10 to by weight of the above described triazine derivative of the present invention as the effective from 40 to by weight of a solid carried and from 2 to by weight of a surface active when it is used in the form of an sion or a flowable it can be usually prepared by ing from 5 to by weight of the triazine derivative of the present invention as the effective from 35 to by weight of a solvent and a surface active agent and from 5 to by weight of other When it is used in the form of a on the other it can be prepared usually by compounding from 1 to by weight of the triazine derivative of the present invention as the effective ingredient and from 85 to by weight of a solid When it is used in the form of they can be prepared usually by compounding from to by weight of the triazine derivative of the present invention the effective from 80 to by 10 weight of a solid carrier and from 2 to by weight of a surface active The solid carrier used here is a fine mineral powder and such a fine mineral powder includes diatomaceous oxides such as hydrated lime and the phosphates such as apatite and the sulfates such as gypsum and the silicates such as acid white quartz silica stone powder and the and so the liquid carrier includes organic solvents such as paraffinic or naphthenic mineral spindle oil and the aromatic xylene and the chlorinated chloroethylene and the cyclohexanol amyl ethylene glycol and the alcohol ethylene glycol monomethyl ethylene glycol ether and the cyclohexenyl cyclohexanone and the Butyl dimethyl methyl ethyl ether and the isopropyl benzyl methyl phthalate and the amides dimethyl formamide and the nitrile and the dimethyl sulfoxide and the like as well as mixtures water and the as the surface active any one can be used among the anionic type ones alkyl 11 lauric acid amide sulfonate and the nonionic type ones octyl polyethylene glycol sorbitan alkyl esters and the cationic type ones lauryl benzyl ammonium lauryl stearyl trimethyl ammonium chloride and the and teric type ones betaine and the it is optional with an object to improve the nature of the preparation form and to enhance the herbicidal effect that the compound of the present invention is used in combination with a polymeric compound or adjuvant such as sodium carboxymethyl carboxy vinyl gum hydroxypropyl methyl cellulose and the The above described triazine derivative of the present invention as a novel compound represented by the general formula exhibits an excellent effect as a herbicide not causing any phytotoxicity for the crops in paddy fields such as grain oat and the like by the soil treatment or foliage treatment either before germination or after germination of the herbicidal effect is high not only against annual weeds as a matter of course but also against perennial weeds and it is very useful as a herbicide not causing any phytotoxicity also for paddy The herbicide of the present invention is administered in a dose of approximately from to 1000 g 12 from 1 to 100 g per 10 ares as the effective When it is applied on foliage of it is administered as being diluted to about 1 to 10000 ppm to 10 to 1000 it is optional to use the triazine tive represented by the general formula in combination with other herbicidal constituents as the effective ingredient of the herbicide of the present Such an auxiliary herbicidal constituent can be a herbicide hitherto on the market including various ones for by the diphenyl type thiol acid type phosphoric type sulfonyl type oxadiazone and the the herbicide of the present invention can be used as mixture with trolling agents of fertilizers and the like according to In the the present invention is described in further detail by way of Preparation Example 1 Sodium methoxide was produced by gradually adding g 13 of sodium to 20 ml of dried methanol and isopropyl biguanide hydrochloride m in the official publication of Japanese Patent Kokai as the starting material I was added thereto and agitated for 30 minutes at room In the next ml of ethyl ester of propionic acid as the starting material II were added dropwise and agitated for 10 hours at room After tion of the the content material was poured into 100 ml of water and subjected to three times of extraction with 50 ml of ethyl This ethyl acetate layer was dried with anhydrous sodium sulfate followed by removal of the ethyl acetate by distillation under reduced The residue was purified by the silica gel column chromatography ing acetate followed by lization from ether to give white 5 triazine The produced results of structural formula and others thereof are shown in Tables 1 to Preparation Examples 2 to 41 Compounds 2 to 41 were obtained by conducting the same procedure as in Preparation Example 1 excepting the use of 20 m moles of the alkyl biguanide hydrochloride in the official publication of Japanese Patent official publication of Japanese Patent Kokai 14 and official publication of Japanese Patent Kokai indicated in Table 1 in place of the isopropyl biguanide hydrochloride as the starting material I in Preparation Example 1 and the use of 20 m moles of the ester indicated in Table 1 in place of the ethyl ester of propionic acid as the ing material The produced results of structural formulas and others of these compounds are shown in Tables 1 to 15 Table 1 16 Table 1 Starting Materials Results of Analysis Preparation Yield Yield Example Melting Elementary I Π Point C H N Preparation Example 8 8 ethyl biganide acid ester resinous Preparation Example 9 phenox propionic acid 29 ethyl biganide ethyl ester resinous Preparation Example 10 propionic acid 24 ethyl ester resinous Preparation Example 11 propionic acid 28 ethyl ester resinous biganide Preparation Example 12 21 ethyl biganide Preparation Example 13 7 acid ester resinous Preparation Example 14 15 resinous biganide Table 1 18 Table 1 19 Table 1 20 Table 1 The value in the brackets shows the theoretical Table 2 Table 2 Table 2 Table 2 Table 2 Table 2 Table 2 Table 2 Table 2 Table 2 Table 2 Table 3 Preparation Compound Infrared absorption Proton nuclear magnetic reso Example prepared spectrum 3280 1 1 1560 solvent 3200 2 Compound 2 1560 solvent 3330 3 Compound 3 1560 3200 4 Compound 1560 sol 3250 5 Compound 5 1540 solven 0 3250 6 Compound 6 1575 solve 3200 7 Compound 1 1560 solve Table 3 Preparation Compound Infrared absorption Proton nuclear magnetic reso Example prepared spectrum 3220 8 Compound 8 1560 solven 3200 9 Compound 9 1550 solven 3200 10 Compound ID 1560 solven 3200 11 Com ound 11 1560 solven 3330 12 Compound 12 1570 solven 3190 13 Compound 1564 solven 3200 14 Compound 14 1560 solven Table 3 Preparation Compound Infrared absorption Example prepared spectrum Proton nuclear magnetic reso 3230 is Compound 15 1575 solvent 3220 Compound 16 16 1460 3180 17 Compound 17 1560 solvent Compound 3200 18 18 1560 solvent 3220 19 Compound 1575 solvent Compound 3200 20 b 20 1560 solvent 3240 21 Compound 20 1560 solvent Table 3 Preparation Infrared absorption Proton nuclear magnetic reso Example prepared spectrum Compound 3240 22 22 1570 solven 3220 23 Compound 23 1560 solven Compound 3220 24 24 1540 Compound 3270 25 25 1560 solve Compound 3350 26 26 1560 solve 3190 27 Compound 3320 27 1540 Compound 3220 28 28 1560 Table 3 Preparation Compound Infrared absorption Proton nuclear magnetic reson Example prepared spectrum Compound 3180 29 29 1540 3150 Compound 30 30 1560 Compound 3360 31 31 1570 Compound 3330 32 32 1570 soi Compound 3350 d 33 33 s 1570 sol 3330 34 Compound 34 1570 3350 Compound 35 35 1560 Table 3 KBr tablet Internal tetramethyl silane In the the actual method for form preparation is described by way of formulation In the formulation examples given refers to by Formulation Example powder Compound of Preparation Example 1 20 parts Diatomaceous earth 62 parts White carbon 15 parts Sodium alkylbenzene sulfonate 2 parts Sodium lignin sulfonate 1 part The above were blended and uniformly mixed and pulverized to give parts of a Formulation Example Emulsion Compound of Preparation Example 2 40 parts Xylene 20 parts Dimethyl formamide 20 parts Solpol 2806B active tured by Toho Chemical 20 parts The above were uniformly dissolved and mixed to give 100 parts of an Formulation Example Dust Compound of Preparation Example 3 2 parts Diatomaceous earth 20 parts Talc 78 parts The above were blended and uniformly mixed and pulverized to give 100 parts of a Formulation Example Granules Compound of Preparation Example 4 1 part Bentonite 30 parts 41 Talc 66 parts Sodium lignin sulfonate 3 parts The above were uniformly mixed and pulverized and thoroughly kneaded with addition of water followed by granu lation and drying to give parts of Formulation Example Flowable agent Compound of Preparation Example 5 25 parts Methyl cellulose part Colloidal silica parts Sodium lignin sulfonate 1 part Polyoxyethylene nonylphenyl ether 2 parts Water parts The above were thoroughly mixed and dispersed and the mixture was subjected to pulverization to give 100 parts of a stable flowable Formulation Example powder A carrier for powder was obtained by uniformly pulverizing and mixing 97 parts of clay product manufactured by Zieglite as a parts of an alkylaryl sulfonic acid salt mercial product manufactured by Kao Atlas as a surface active agent and parts of a type and anionic type surface active agent product Solpol manufactured by Toho Chemical Industry A powder was obtained by uniformly verizing mixing 90 parts of this carrier for ble powder and 10 parts of the triazine derivative obtained in the above described Preparation 42 Examples 1 to 41 Upland field soil treatment test Wagner pots of were filled with a soil of paddy field and seeds of Digitaria Alopecurus Abutilon Veronica Viola Polygonum Galium sparium echinospermon corn and grain sorghum were uniformly sowed in the surface Prior to the germination of the grain sorghum and weeds the soil surface was uniformly treated with a specified volume of a diluted solution of the herbicide obtained in the above described Formulation Example 6 and the pots were kept standing in a greenhouse with periodical water Table 4 shows the results of the investigations of the herbicidal effects and phytotoxicity to the corn and grain sorghum after 30 days from the treatment with the herbicide The dose was 25 to 100 ares calculated as the amount of the effective The phytotoxicity to the corn and grain sorghum and the herbicidal effects are expressed as shown below by measuring the respective Phytotoxicity to Extent of phytotoxicity corn grain sorgham to untreated 0 100 1 61 to 99 2 21 to 60 3 11 to 20 4 1 to 10 5 0 43 Degree of Herbicidal effects cidal effects to treated 0 00 to 99 2 21 to 60 3 to 20 4 1 to 10 5 0 Comparative Examples 1 to The same procedure as in Example 1 was undertaken ing the use of the triazine derivatives A to C in the official publication of Japanese Patent Kokai D in the official publication of Japanese Patent Kokai E in the official publication of Japanese Patent Kokai or F in the official publication of Japanese Patent expressed by the formulas given below in place of the triazine prepared in Preparation in Example The results are shown in Table 44 Triazine derivative A Triazine derivative Triazine derivative Triazine derivative Triazine derivative E Triazine derivative F 45 4 Herbicidal effect Compound Amount of herbicide Alopecurus on Veronica Polygonum Viola Amaranthus Galium sanguinal is theophrasti peraica persicaria arvensis patuius Wheat Barley Corn Grain sorghum 0 0 0 Example Compound of 1 Preparation 0 0 0 0 0 0 0 0 0 Example Compound of 2 Preparation 0 0 0 0 2 o o a o 100 Example Compound of 3 Preparation 50 Example 3 25 5 5 5 5 5 5 5 0 0 0 0 Compound of 4 Preparation 50 5 5 5 5 5 5 5 5 0 0 0 0 Example 4 25 5 5 5 5 5 5 5 5 0 0 0 0 100 5 5 5 5 5 5 5 5 0 0 0 Example Compound of 5 Preparation 50 5 5 5 5 5 5 5 5 0 0 5 25 5 5 5 5 5 5 5 5 0 0 0 100 5 5 5 5 5 5 5 5 0 0 0 0 Example Compound of 6 Preparation 50 5 5 5 5 5 5 5 5 0 0 0 0 6 25 5 5 5 5 5 5 5 5 0 0 0 0 100 5 5 5 5 5 5 5 5 0 0 0 Example Compound of 7 Preparation 50 5 5 5 5 5 5 5 5 0 0 0 0 Example 7 25 5 5 5 5 5 5 5 5 0 0 0 0 46 4 effect Compound Amount of used Veronica Polygonum Viola Amaranthus Galium ersicaria patuius Corn Grain sorghum Compound of 50 0 8 25 Compound of 9 Preparation 9 0 0 0 0 Example Compound of 10 Preparation 0 0 Example 10 0 0 0 0 Compound of Preparation 0 0 Example 11 25 0 100 0 0 Coirpound of 50 0 0 Example 12 25 0 0 100 5 5 5 5 5 5 0 0 0 Conpound of 13 Preparation 50 5 5 5 5 5 5 0 0 0 13 25 5 5 5 5 5 5 0 0 0 0 0 Example Compound of 14 Preparation 0 0 Example 14 0 0 47 4 Compound Amount used nerbicide Alopecurus Abutilon Veronica Polygonum Viola Gal myosuroides is theophrasti patulus Wheat Barley Corn Grain sorghum 100 0 0 Compound of Preparation 50 0 0 Example 15 25 ΰ 0 0 0 Coitpound of 16 Preparation 0 0 0 Example 0 0 0 100 0 le Compound of Preparation 50 0 Example 17 25 0 0 0 Exampl Compound of 18 0 0 Example 18 0 0 1Π0 Compound of 19 Preparation 50 19 25 0 0 Example Compound of 20 Preparation 0 0 20 0 0 0 0 0 Example Compound of 21 Preparation 0 0 0 Example 21 0 0 48 4 Herbicidal effect Phytotoxici tv ompound Amount of herbicide Abut i Ion Veronica Polygonum Viola Galium theophrasti persica persic ria patulus spar Wheat Barley Corn Grain sorghum 5 0 0 0 Compound of 22 Preparation 5 0 0 0 0 Example 22 5 0 Π 0 0 0 0 Example Compound of 23 Preparation 50 0 0 0 0 0 Compound of 24 Preparati n 0 0 24 0 0 100 0 0 Exampl Compound of 25 Preparation 0 0 25 25 0 0 0 0 Compound of 28 0 0 Exampl 28 0 0 49 Table i Herbicidai effect Compound Amount of herbicide Alopecurus Veronica Polygonum Viola myosuroides sanguinal theophrasti patulus sparium Wheat Corn Grain 5 5 0 0 0 Compound of Preparation 50 5 5 0 0 0 0 29 5 5 0 0 0 0 100 0 0 0 Compound of 0 0 0 30 0 0 0 0 0 0 Compound of 31 Preparation 0 0 0 31 o n o Compound of 32 Preparation Example 32 0 0 0 0 0 Compound of 33 Preparation 0 0 0 Example 33 0 0 0 0 0 0 Example Compound of 34 Preparation 0 0 0 Example 34 0 0 0 Compound of 35 Preparation 35 50 4 Herbicidal effect Compound Amount of used herbicide Alopecurus Oigitaria Abutilon Veronica Polygonum Viola Galium myosuroides sanguinal theophrasti persica persicaria patulus sparium Wheat Corn Grain sorghum 0 0 D 0 Compound of 36 Preparation 0 0 36 0 D 0 0 0 Compound of 37 Preparation 50 0 0 37 25 0 0 0 Compound of 50 0 38 25 0 0 Compound of 39 Preparation 0 39 0 100 5 5 5 5 5 5 0 0 0 0 Compound of 40 Preparation 50 5 5 5 5 5 5 5 5 0 0 0 0 4Π 25 5 5 5 5 5 5 5 5 0 0 0 0 100 5 5 5 5 5 5 5 5 0 0 0 0 Compound of 41 Preparation 50 5 5 5 5 5 5 5 5 0 0 0 0 Example 41 25 5 5 5 5 5 0 0 0 0 51 i effect ty Compound Amount of used herbicide i Ion Veronica Polygonum Viola Galium myosuroides sanguinal persicaria patulus sparium Barley Corn drain sorghum echinospermon 100 4 0 0 0 tive Tri 50 2 0 0 0 0 Example 1 A 25 1 0 0 0 0 100 0 0 0 tive Triazine 50 0 0 0 Example derivative 2 B 25 0 0 0 100 5 5 4 5 0 0 tive Triazine 50 3 3 4 4 0 0 Example 3 C 25 2 2 3 3 0 0 100 5 5 4 5 5 4 5 4 0 0 0 0 tive Triazine 50 3 3 4 4 4 3 0 0 0 0 Example 4 3 2 3 3 3 3 3 1 0 0 0 0 100 4 4 3 3 4 4 2 0 0 0 0 50 1 2 3 3 3 2 2 0 0 0 0 0 E 25 0 n 1 0 0 0 0 0 0 0 0 100 3 5 4 5 4 4 5 4 0 0 0 0 Triazine 50 2 3 3 4 3 4 3 0 0 0 0 derivative F 25 0 1 2 2 0 1 0 0 0 0 52 Examples 42 to 82 Foliage treatment test Seeds of weeds including Abutilon Common Amaranthus Cassia Ipomoea Galium sparium Veronica persica and seeds of crops including grain barley and oat were sowed on to the Wagner pots of filled with soil of upland field after covering up with were grown in a greenhouse when the weeds were in their to period and the crops were in their an aqueous suspension of a specified amount of the herbicide prepared in the above described Formulation Example 6 was uniformly sprinkled by spraying to the parts of stems and leaves in a liquid volume ing to 100 they were grown in a greenhouse and the phytotoxicity on the crops and the herbicidal effects were estimated according to the following criteria on the 20th day of the The results are shown in Table of Degree of herbicidal Herbicidal effects effects killed less than 5 no 1 5 to 20 2 20 to 40 3 40 to 70 4 70 to 80 5 90 or more complete 53 lowing equation by determining the overground raw grass weight in the phytotoxicity treated zone and the overground raw grass weight in the untreated overground raw weight in treated killed overground raw grass weight untreated zone Degree of phytotoxicity 0 no phytotoxicity to crops 1 almost no phytotoxicity to crops 2 little but noticeable phytotoxicity to crops 3 noticeable phytotoxicity to crops 4 remarkably strong phytotoxicity to crops 5 almost complete withering of crops Comparative Examples 7 to 12 The same procedure as in Example 41 was undertaken ing the use of the triazine derivative A E or F shown in Comparative Examples 1 to 6 in place of the triazine vative prepared in Preparation Example in Example The results are shown in Table 54 Table 5 Herbicidai effect Compound of used Corn Grain Wheat Barley Oats Common Amaranthus Cassia lpomoea Galium Veronica sorghum blackjack patulus obtusifolia purpurea sparium 400 0 0 0 0 0 5 5 5 5 5 5 5 Compound 200 0 0 0 0 0 5 5 5 5 5 5 5 Example 100 0 0 0 0 0 5 5 5 5 5 5 5 42 Example 50 0 0 0 0 0 5 5 5 5 5 5 5 25 0 0 0 0 0 5 5 5 5 5 5 5 0 0 0 0 0 5 5 5 5 5 5 5 400 0 0 0 0 0 5 5 5 5 5 5 5 Compound 200 0 0 0 0 5 5 5 5 5 5 5 Example 100 0 0 0 0 0 5 5 5 5 5 5 5 43 tion Example 50 0 0 0 0 5 5 5 5 5 5 5 25 0 0 0 0 0 5 5 5 5 5 5 5 0 0 0 0 5 5 5 5 5 5 5 400 0 0 0 0 5 5 5 5 5 5 5 Compound 200 0 0 0 0 0 5 5 5 5 5 5 5 Example 100 0 0 0 0 0 5 5 5 5 5 5 44 tion Example 50 0 0 0 0 0 5 5 5 5 5 5 5 25 0 0 0 5 5 5 5 5 5 5 0 0 0 0 0 5 5 5 5 5 5 5 400 0 0 0 0 0 5 5 5 5 5 5 5 Compound 200 0 0 0 0 0 5 5 5 5 5 5 5 of Example 100 0 0 0 0 0 5 5 5 5 5 5 5 45 Example 50 0 0 0 0 0 5 5 5 5 5 5 5 4 25 0 0 0 0 0 5 5 5 5 5 5 5 0 0 0 0 0 5 5 5 5 5 5 5 55 5 Herbicidal effect Compound Amount used herbicide Corn Grain Barley Oats Common ran thus Gal Veronica obtusi fol purpurea persica echinospermon 400 0 0 0 0 0 5 5 5 5 5 5 5 Compound 0 0 0 0 0 5 5 5 5 5 5 5 Example 0 0 0 0 0 5 5 5 5 5 5 5 46 Example 50 0 0 0 0 0 5 5 5 5 5 5 5 5 25 0 0 0 0 0 5 5 5 5 5 5 5 0 0 0 0 0 5 5 5 5 5 5 5 400 0 0 0 0 0 5 5 5 5 5 5 5 Compound 0 0 0 0 0 5 5 5 5 5 5 5 Example 100 0 0 0 0 0 5 5 5 5 5 5 5 47 tion Example 50 0 0 0 0 0 5 5 5 5 5 5 5 6 25 0 0 0 0 0 5 5 5 5 5 5 5 0 0 0 0 5 5 5 5 5 5 5 400 0 0 0 0 0 5 5 5 5 5 5 5 Compound 200 0 0 0 0 0 5 5 5 5 5 5 5 Example 0 0 0 0 0 5 5 5 5 5 5 5 48 tion 50 0 0 0 0 0 5 5 5 5 5 5 5 25 0 0 0 0 0 5 5 5 5 5 5 5 0 0 0 0 0 5 5 5 5 5 5 5 400 0 0 0 0 0 5 5 5 5 5 5 5 Compound 200 0 0 0 0 5 5 5 5 5 5 5 of 100 0 0 0 0 0 5 5 5 5 5 5 5 49 tion 50 0 0 0 0 0 5 5 5 5 5 5 5 25 0 0 0 0 0 5 5 5 5 5 5 5 0 0 0 0 5 5 5 5 5 5 56 Table 5 Phytotoxici ty effect Compound Amount of herbicide Corn Grain Wheat Barley Oats i on Common Amaranthus Cassia Galium Veronica sorghum theophrasti blackjack patulus obtusi folia purpurea sparium persica echinospermon 400 0 0 0 0 0 5 5 5 5 5 5 5 Compound 200 0 0 0 0 0 5 5 5 5 5 5 5 of 100 0 0 0 0 0 5 5 5 5 5 5 5 50 tion 50 0 0 0 0 0 5 5 5 5 5 5 5 9 25 0 0 0 0 0 5 5 5 5 5 5 0 0 0 0 5 5 5 5 5 400 0 0 0 0 0 5 5 5 5 5 5 5 Compound 0 0 0 0 5 5 5 5 5 5 5 ion 0 0 0 0 0 5 5 5 5 5 5 51 50 0 0 0 0 0 5 5 5 5 5 5 1IJ 25 0 0 0 0 5 5 5 5 5 5 5 0 0 0 0 5 5 5 5 5 5 400 0 0 0 n a 5 5 5 5 5 5 5 Compound 200 0 0 0 5 5 5 5 5 5 100 0 0 0 0 0 5 5 5 5 5 5 5 52 ti n Exam 50 0 0 0 0 c 5 5 5 5 5 5 5 11 25 0 0 0 Π 5 5 5 5 5 5 5 0 0 0 0 0 5 5 5 5 5 5 400 0 0 0 0 5 5 5 5 5 5 0 0 a 0 0 5 5 5 5 5 5 5 57 Table 5 ty Herbicidai effect Compound of used herbicide Corn Grain Wheat Oats i ion Common A aranthus Cassia Galium Veronica sorghum blackjack purpurea sparium persica 400 0 n 0 0 0 5 5 5 5 5 5 5 Ex 400 0 η 0 0 5 5 5 5 5 5 5 Compound 200 0 0 0 0 0 5 5 5 5 5 5 5 f 100 0 0 0 0 0 5 5 5 5 5 5 5 55 tion Example 50 0 0 0 0 5 5 5 5 5 5 5 14 25 0 0 0 0 0 5 5 5 5 5 0 0 0 a 5 5 5 5 5 5 5 400 0 0 0 0 0 5 5 5 5 5 5 Compound 200 0 0 0 0 a 5 5 5 5 5 5 of n 0 0 0 0 5 5 5 5 5 5 5 56 Example 50 0 0 0 0 0 5 5 5 5 5 5 5 15 0 0 0 0 a 5 5 5 5 5 5 5 0 0 0 a 0 5 5 5 5 5 5 5 0 0 0 0 0 5 5 5 5 5 5 5 Compound 200 0 0 0 a 5 5 5 5 5 5 Example 100 0 0 0 0 o 5 5 5 5 5 5 5 57 50 0 0 0 0 5 5 5 5 5 5 5 25 0 0 0 0 a 5 5 5 5 0 0 0 0 0 5 5 5 5 5 58 5 Phototoxicity effect of used herbicide Corn Grain Wheat Barley Oats Abut Ion Common Cassia Ipomoea Veronica sorghum b ckjack patulus obtusifol ia purpurea sparium persica echinospermon 400 0 ΰ 0 0 0 5 5 5 5 5 5 5 Compound 2D0 0 0 0 0 0 5 5 5 5 5 5 5 Example 100 0 0 0 0 0 5 5 5 5 5 5 5 i n Example 50 0 0 0 0 0 5 5 5 5 5 5 5 25 0 0 0 0 5 5 5 5 5 5 5 0 0 0 0 0 5 5 5 5 5 5 5 400 0 0 0 0 0 5 5 5 5 5 5 5 Compound 200 0 0 0 0 5 5 5 5 5 5 5 of Example 100 0 0 0 0 0 5 5 5 5 5 5 5 59 tion Example 50 0 0 0 0 0 5 5 5 5 5 5 5 25 0 0 0 0 0 5 5 5 5 5 5 5 0 0 0 0 0 5 5 5 5 5 5 5 400 0 0 0 0 0 5 5 5 5 5 5 5 Compound 200 0 0 0 0 0 5 5 5 5 5 5 b Example 0 0 5 5 5 5 5 5 5 60 tion Example 50 0 0 0 0 5 5 5 5 5 5 5 19 25 0 0 0 0 0 5 5 5 5 5 5 5 0 0 0 0 5 5 5 5 5 5 5 400 0 0 0 0 0 5 5 5 5 5 5 5 Compound 200 0 0 0 0 5 5 5 5 5 5 5 f Example 0 0 0 5 5 5 5 5 5 61 tion Example 50 0 0 0 0 0 5 5 5 5 5 5 5 20 25 0 0 0 0 0 5 5 5 5 5 5 5 0 0 0 0 0 5 5 5 5 5 5 5 59 Table 5 Herbicidal effect Compound Amount of used herbicide Corn Barley Oats Abutilon Common flmaranthus Cassia Ipomoea Galium Veronica sorghum theophrasti blackjack patulus obtusi folia purpurea sparium persica echinospermon 4110 0 0 0 0 0 5 5 5 5 5 5 5 Ex 0 0 0 0 5 5 5 5 5 5 5 400 0 0 0 0 5 5 5 5 5 5 5 Compound 200 0 0 0 0 0 5 5 5 5 5 5 5 of Example 0 0 0 0 5 5 5 5 5 5 5 63 tion 50 0 0 0 5 5 5 5 5 5 5 22 25 0 0 0 0 5 5 5 5 5 5 5 0 0 0 0 5 5 5 5 5 5 5 400 0 0 0 0 0 5 5 5 5 5 5 5 Compound 200 0 0 0 0 0 5 5 5 5 5 5 5 of Example 100 0 0 0 0 0 5 5 5 5 5 5 5 64 tion Example 50 0 0 0 0 0 5 5 5 5 5 5 5 23 25 0 0 0 0 0 5 5 5 5 5 5 5 0 0 0 0 0 5 5 5 5 5 5 5 400 0 0 0 0 0 5 5 5 5 5 5 5 Ex 0 0 0 0 0 5 5 5 5 5 5 5 60 5 ty Herbicidal effect C npound used herbi ide Corn Wheat Oats Abuti Coitmon ran thus Cassia Ipomoea Veronica sorghum theophraeti obtusi fol ia purpurea spar persica echinospermon 400 0 0 0 0 0 5 5 5 5 5 5 Conpound 200 0 0 0 0 0 5 5 5 5 5 5 100 0 0 0 0 0 5 5 5 5 5 5 5 66 tion e 50 0 0 0 0 0 5 5 5 5 5 5 5 25 0 0 0 0 5 5 5 5 5 5 0 0 0 n 5 5 5 5 5 5 5 400 0 0 0 0 0 5 5 5 5 5 5 Conpound 200 0 0 0 0 0 5 5 5 5 5 5 of 100 0 0 0 0 0 5 5 5 5 5 5 5 tion Example 50 0 0 0 0 0 5 5 5 5 5 5 5 25 0 0 0 0 5 5 5 5 5 5 5 Π 0 0 0 5 5 5 5 5 5 5 400 0 0 n 0 0 5 5 5 5 5 5 Compound 200 0 0 0 0 0 5 5 5 5 5 5 5 Example Prepara 100 0 0 0 0 0 5 5 5 5 5 5 5 68 tion Exam 50 0 0 0 0 0 5 5 5 5 5 5 5 27 25 0 0 0 0 0 5 5 5 5 5 5 5 0 0 0 0 0 5 5 5 5 5 5 5 400 0 0 0 0 0 5 5 5 5 5 5 5 Compound 200 0 0 0 0 0 5 5 5 5 5 5 Exanple 100 0 0 0 0 5 5 5 5 5 5 5 69 tion 50 0 0 0 0 5 5 5 5 5 5 5 28 25 0 0 0 0 0 5 5 5 5 5 5 5 0 0 0 0 5 5 5 5 5 5 5 61 Table 5 effect Compound Amount of used herbicide Corn 6rain Wheat Barley Oats Abutilon Common Amaranthus Cassia lpomoea Galium Veronica sorghum theophrasti blackjack patulus purpurea spariu persica 400 0 0 0 0 0 5 5 5 5 5 5 5 Compound 200 0 0 0 0 5 5 5 5 5 5 5 of Example 100 0 0 0 0 0 5 5 5 5 5 5 5 tion Example 50 0 0 0 0 0 5 5 5 5 5 5 5 29 25 0 0 0 0 5 5 5 5 5 5 0 0 0 0 0 5 5 5 5 5 5 400 n 0 0 0 0 5 5 5 5 5 5 5 Compound 200 0 0 0 0 0 5 5 5 5 5 5 of Example 100 0 0 0 0 0 5 5 5 5 5 5 5 ti n Exampl 50 0 0 0 0 0 5 5 5 5 5 5 5 30 25 0 0 0 5 5 5 5 5 5 5 0 0 0 0 0 5 5 5 5 5 5 5 400 0 0 0 0 0 5 5 5 5 5 5 5 Compound 200 0 0 0 0 0 5 5 5 5 5 5 5 100 0 0 0 0 0 5 5 5 5 5 5 5 72 Exau 50 0 0 0 u 5 5 5 5 5 5 5 31 25 0 0 0 0 0 5 5 5 5 5 5 5 0 0 0 0 0 5 5 5 5 5 5 5 400 0 0 0 0 0 5 5 5 5 5 5 5 Compound 200 0 0 0 0 0 5 5 5 5 5 5 5 100 0 0 0 0 n 5 5 5 5 5 5 5 73 50 0 0 0 0 0 5 5 5 5 5 5 5 25 0 0 0 0 0 5 5 5 5 5 5 5 0 0 0 0 0 5 5 5 5 5 5 5 62 Table 5 Phytoto Herbicidal effect Amount of used herbicide Corn Grain Wheat Barley Oats Common Amaranthus Cassia Ipomoea Galium Veronica sorghum theophrasti blackjack patulus obtueifolia purpurea echinoepermon n 0 0 0 0 u 5 5 5 5 5 5 5 Compound 0 0 0 0 5 5 5 5 5 5 5 of Example 100 0 0 0 0 0 5 5 5 5 5 5 5 74 tion 50 0 0 0 0 0 5 5 5 5 5 5 5 25 0 0 0 0 0 5 5 5 5 5 5 5 0 0 0 0 0 5 5 5 5 5 5 5 400 0 0 0 0 5 5 5 5 5 5 Compound 200 0 0 0 0 0 5 5 5 5 5 5 5 of Example 100 0 0 0 0 0 5 5 5 5 5 5 5 75 tion Exam 50 11 0 0 0 0 5 5 5 5 5 5 5 25 0 0 0 0 0 5 5 5 5 5 5 5 0 0 0 0 5 5 5 5 5 5 5 400 0 0 0 0 0 5 5 5 5 5 5 5 Compound 200 0 0 0 0 0 5 5 5 5 5 5 5 Example 100 0 0 0 0 0 5 5 5 5 5 5 5 76 50 0 0 0 0 0 5 5 5 5 5 5 5 35 25 0 0 0 0 0 5 5 5 5 5 5 5 0 0 0 0 0 5 5 5 5 5 5 5 400 0 0 0 0 0 5 5 5 5 5 5 5 Compound 200 0 0 0 0 0 5 5 5 5 5 5 5 Example 100 0 0 0 0 0 5 5 5 5 5 5 5 77 tion Example 50 0 Π 0 0 0 5 5 5 5 5 5 5 25 0 0 0 0 0 5 5 5 5 5 5 5 0 0 0 0 0 5 5 5 5 5 5 5 63 Table 5 Phytotoxicity Herbicidai effect Compound used herbicide Corn Grain Wheat Barley Oats 1 on Common Cassia Ipomoea Galium Veronica sorghum theophrasti blackjack obtusifolia purpurea sparium persica eehinoepermon 400 0 0 0 0 0 5 5 5 5 5 5 5 Compound 200 0 0 0 5 5 5 5 5 5 5 of 100 0 0 0 0 0 5 5 5 5 5 5 5 78 tion 50 0 0 0 0 5 5 5 5 5 5 5 37 25 0 0 0 0 5 5 5 5 5 5 0 0 a 0 0 5 5 5 5 5 5 5 400 0 0 0 0 0 5 5 5 5 5 5 5 Compound 200 0 0 0 0 5 5 5 5 5 5 5 of Example 100 0 0 0 0 0 5 5 5 5 5 5 5 79 tion 50 0 0 0 0 0 5 5 5 5 5 5 25 0 0 0 0 0 5 5 5 5 5 5 5 0 0 0 0 0 5 5 5 5 5 5 5 400 0 0 0 0 0 5 5 5 5 5 5 5 Compound 200 0 0 0 0 n 5 5 5 5 5 5 5 of Example 100 0 0 0 0 0 5 5 5 5 5 5 5 80 tion 50 0 0 0 0 5 5 5 5 5 5 39 25 0 0 0 0 0 5 5 5 5 5 0 0 0 0 0 5 5 5 5 5 5 5 400 0 0 0 0 0 5 5 5 5 5 5 5 Compound 200 0 0 0 0 0 5 5 5 5 5 5 5 Example 100 0 0 0 0 0 5 5 5 5 5 5 5 81 tion 50 0 0 0 0 5 5 5 5 5 5 25 0 0 0 0 0 5 5 5 5 5 5 5 0 0 0 0 n 5 5 5 5 5 5 5 64 Table 5 Herbicidal effect οτ used Corn Grain Whe Barley Oats Ion Common Aroaranthus Ipomoea Gal Veronica sorghum theophrasti obtusifol purpurea sparium echinospermon 400 0 0 0 5 5 5 5 5 5 Compound 200 fi 0 0 0 0 5 5 5 5 of Example 100 0 0 0 5 5 5 5 5 5 82 tion 50 0 0 0 0 0 5 5 5 5 5 5 5 41 25 0 0 0 0 0 5 5 5 5 5 5 0 0 0 0 0 5 5 5 5 5 5 5 400 0 0 0 0 0 5 5 5 5 5 5 200 0 0 0 0 0 5 5 5 5 5 5 5 tive 100 0 0 0 0 0 5 5 5 5 5 5 5 Example deri 1 tive B 50 0 0 0 0 3 4 3 3 4 0 0 0 0 3 3 4 3 2 3 0 0 0 0 0 1 2 2 2 2 1 2 400 0 0 0 0 0 5 5 5 5 5 5 5 200 0 0 0 0 0 5 5 5 5 5 5 5 tive 100 0 0 0 0 0 5 5 5 5 5 5 5 Example 8 tive C 50 0 0 0 0 0 3 4 4 3 3 4 25 0 0 0 0 0 3 3 4 3 2 3 0 0 0 0 0 2 2 1 2 1 2 400 5 5 5 25 3 3 65 Table 5 Herbicidal effect Compound used Corn Grain Wheat Barley Oats Abut Ion Aroaranthus Ipomoea Gal Veronica sorghum theophrasti blackjack obtusi fol purpurea sparium persica echinospermon 400 0 0 0 0 5 5 5 5 5 5 5 200 0 0 0 0 0 5 5 5 5 5 5 5 Triazine 100 11 0 0 0 0 5 5 5 5 5 4 5 E 50 0 0 0 0 n 4 4 5 5 5 4 3 25 0 0 0 0 0 4 4 4 3 4 3 2 0 0 0 0 o 3 3 4 2 3 2 1 400 0 0 0 0 5 5 5 5 5 5 5 200 0 0 0 0 0 5 5 5 5 5 5 5 Triazine 100 0 0 0 0 0 5 5 5 4 5 5 5 11 tive 50 0 0 0 0 0 3 5 5 3 5 3 4 25 0 0 0 0 3 5 5 2 5 2 3 0 0 0 0 0 1 4 5 2 3 1 2 400 0 11 0 0 0 5 5 5 5 5 5 5 200 0 0 0 0 5 5 5 5 5 5 5 100 0 0 0 0 0 5 5 5 5 5 5 5 12 tive f 50 0 0 n 0 0 4 5 5 4 5 5 5 25 0 0 0 0 0 3 5 5 3 5 4 4 0 0 0 0 0 1 4 5 2 3 3 3 66 Examples 83 to 123 Paddy soil treatment test Porcelain pots of are were filled with a paddy field soil and seeds of Echinochola var formosensis Ohwi Cyperus weeds indica Koehne uligirosa Koehne and Monochorea vaginalis Presl and Scirpus juncoides Hotarui Ohwi Koyama were uniformly sowed to the surface layer and further tubers of Cyperus serotinus and Sagittaria pygmaea were transplanted followed by transplantation of paddy rice in the bifoliate Before germination of the a specified volume of a diluted solution of the herbicide obtained in the above described Formulation Example 6 was uniformly dropped to the water surface to effect treatment followed by standing of the pots in a greenhouse with periodical sprinkling of Table 6 shows the results in the investigations of the herbicidal effects and phytotoxicity to the rice crop after 20 days from the treatment with the herbicide the dose is given by the amount of the effective ingredient per 10 the phytotoxicity to paddy rice and the herbicidal effects are expressed as shown below by determining the respective Phytotoxicity to paddy rice Extent of phytotoxicity to untreated 0 100 1 95 to 99 2 90 to 94 3 80 to 89 4 60 to 79 Herbicidal effects to untreated 0 100 1 61 to 99 2 21 to 60 3 11 to 20 4 1 to 10 5 0 Comparative Examples 13 to The same procedure as in Example 83 was undertaken ing the use of the triazine derivative E or F shown in Comparative Examples 1 to 6 in place of the triazine vative prepared in Preparation Example 1 in Example The results are shown in Table 68 Amount Herbicidal effect Compound Paddy used herbicide Echinochola Cyperus Scirpus Cyperus Sagi ttaria rice llotarui di f weeds formoeensis Koyama 5 5 5 5 5 5 0 Compound Exairple 50 5 5 5 5 5 5 0 83 Preparation 1 25 5 5 5 5 5 5 0 5 5 5 5 5 5 0 100 5 5 5 5 5 0 Compound Example of 50 5 5 5 5 5 5 0 84 2 25 5 5 5 5 5 5 0 5 5 5 5 5 5 0 100 5 5 5 5 5 5 0 Compound 50 5 5 5 5 5 5 0 85 Preparation Exam 3 25 5 5 5 5 5 5 0 5 5 5 5 5 5 0 100 5 5 5 5 5 5 0 Compound Exairple 50 5 5 5 5 5 5 0 86 Preparation 4 25 5 5 5 5 5 5 0 5 5 5 5 5 5 0 100 5 5 5 5 5 5 0 50 5 5 5 5 5 5 0 87 Preparation 5 25 5 5 5 5 5 5 0 5 5 5 5 5 5 0 100 5 5 5 5 5 5 0 Compound 50 5 5 5 5 5 5 0 88 Preparation 6 25 5 5 5 5 5 5 0 5 5 5 5 5 5 0 69 6 Amount Herbicidal effect Compound Paddy used herbicide Echinochola i Cyperus Scirpus juncoides Cyperus Broadleaf Sagittaria rice serotinus Hotarui weeds pygmaea plants Koyama Compound of 5Π 89 Preparation Example 7 25 5 5 5 5 5 5 0 5 5 5 5 5 5 0 Compound of 5U 5 5 5 5 5 5 0 90 Preparation Example 8 25 5 5 5 5 5 0 5 5 5 5 5 5 0 5 5 5 5 5 5 0 Compound 50 5 5 5 5 5 5 0 91 Preparation 9 25 5 5 5 5 5 5 0 5 5 5 5 5 5 0 100 5 5 5 5 5 5 0 Compound 50 5 5 5 5 5 5 0 92 Preparation Example 25 5 5 5 5 5 5 0 5 5 5 5 5 5 0 100 5 5 5 5 5 5 0 Compound f 50 5 5 5 5 5 0 93 Preparation Example 11 25 5 5 5 5 5 5 0 5 5 5 5 5 5 0 100 5 5 5 5 5 5 0 Compound Example of 50 5 5 5 5 5 5 0 94 Preparation Example 12 25 5 5 5 5 5 5 0 5 5 5 5 5 5 0 70 6 Herbicidal effect Compound of Paddy used herbicide Echinochola i Scirpus Cyperus rice serotinus difformis weeds plants formosensis Koyama Mi DO Compound of 50 95 Preparation 13 100 5 5 5 5 5 5 0 Compound Example of 50 5 5 5 5 5 5 0 96 Preparation Example 14 5 5 5 5 5 5 0 5 5 5 5 5 5 0 100 5 5 5 5 5 5 0 Compound Example of 50 5 5 5 5 5 5 0 97 Preparation Example 15 25 5 5 5 5 5 5 0 5 5 5 5 5 5 0 5 5 5 5 5 5 0 Compound Example of 50 5 5 5 5 5 5 0 98 Preparation Example 16 25 5 5 5 5 5 5 0 5 5 5 5 5 5 0 100 Compound Example of 50 99 Preparation 17 25 100 Compound of 50 Preparation Example 18 25 71 6 Amount effect Conp und of Paddy used herbicide Fchi i Cyperus juncoides Cyperus Brcadleaf Sagittaria rice serotinus Hotarui difformis weeds pygmaea plants formosensis Ohwi Ohwi Koyama 100 Compound of 50 Preparation Example 25 5 5 5 5 5 5 0 Compound Example of 50 5 5 5 5 5 5 0 102 Preparation Example 25 5 5 5 5 5 5 0 5 5 5 5 5 5 0 100 5 5 5 5 5 5 0 Compound Example of 50 5 5 5 5 5 5 0 103 Preparation Example 21 25 5 5 5 5 5 5 0 5 5 5 5 5 5 0 5 5 5 5 5 5 0 Compound Example o1 50 5 5 5 5 5 5 0 104 Preparation Example 22 25 5 5 5 5 5 5 0 5 5 5 5 5 5 0 100 Compound ample of 50 105 Preparation 23 25 100 5 5 5 5 5 5 0 Compound Example of 50 5 5 5 5 5 5 0 106 Preparation Example 24 25 5 5 5 5 5 5 0 5 5 5 5 5 5 0 72 Table 6 Amount Hfrbicidal Compound of Paddy used herbicide juncoides Broadleaf Sagittaria rice serotinus Hotarui difformis weeds pygmaea plants Mi Compound Example of 511 Preparation 25 25 Compound of 50 108 Preparation 26 100 Compound Example of 50 109 Preparati n 27 25 100 Compound of 50 Preparation Example 28 25 100 5 5 5 5 5 5 0 Compound Example of 50 5 5 5 5 5 5 0 Preparation Example 29 25 5 5 5 5 5 5 0 5 5 5 5 5 5 0 100 5 5 5 5 5 5 0 Compound Example of 50 5 5 5 5 5 5 0 112 Preparation Example 30 25 5 5 5 5 5 5 0 5 5 5 5 5 5 0 73 6 Amount Herbicidal effect Compound of Paddy herbicide gal i Cyperus juncoidee Cyperus Eroadleaf Sagittaria rice serotinus Hotarui weeds pygmaea plants formosensis 5 5 5 5 5 5 0 Example of 50 5 5 5 5 5 5 0 Preparation Example 31 25 5 5 5 5 5 5 0 5 5 5 5 5 5 0 100 5 5 5 5 5 0 Compound Example of 50 5 5 5 5 5 5 Preparation Example 32 5 5 5 5 5 5 5 5 5 5 5 5 0 5 5 5 5 5 5 0 Compound Example of 50 5 5 5 5 5 5 0 115 Preparation Example 33 25 5 5 5 5 5 5 0 5 5 5 5 5 5 0 100 5 5 5 5 5 5 Q Compound Example of 50 5 5 5 5 5 5 0 116 Preparation Example 34 25 5 5 5 5 5 5 0 5 5 5 5 5 5 0 100 Compound 50 Preparation 35 25 100 5 5 5 5 5 5 0 Compound Example of 50 5 5 5 5 5 5 0 118 Preparation Example 36 25 5 5 5 5 5 5 0 5 5 5 5 5 5 0 74 Table 6 Herbicidal etfect Compound of Paddy used herbicide I i Cyperus juncoides Cyperus Broadleaf Sagittaria rice serotinus Hotarui difformis weeds pygmaea plants formosensis 100 5 5 5 5 5 5 0 Compound Example of 50 5 5 5 5 5 0 119 Preparation Example 37 25 5 5 5 5 5 5 ϋ 5 5 5 5 5 5 0 100 5 5 5 5 5 5 0 Compound Example of 50 5 5 5 5 5 5 0 120 Preparation Example 38 25 5 5 5 5 5 5 0 5 5 5 5 5 5 0 100 5 5 5 5 5 5 0 Compound Example of 50 5 5 5 5 5 5 0 121 Preparation Example 39 25 5 5 5 5 5 5 0 5 5 5 5 5 5 0 100 5 5 5 5 5 5 0 Compound Example of 50 5 5 5 5 5 5 0 122 Preparation Example 40 25 5 5 5 5 5 5 0 5 5 5 5 5 5 0 Compound Example of 50 123 Preparation Example 41 25 100 5 5 5 5 5 5 0 Co Triazine 50 5 5 4 5 4 5 0 tive derivative Example Λ 25 5 4 3 5 4 3 0 13 5 4 2 5 4 2 0 75 6 Herbicidal effect Compound of used herbicide Echinochola i Scirpus juncoides Cyperus Broadleaf serotinus Hotarui difformis weeds pygmaea fnrmosensis Ohwi Ohwi Koyama 5 4 5 5 ft 5 0 Triazine 50 5 4 4 5 0 tive Example B 25 5 3 4 5 4 3 0 5 3 5 4 2 0 100 5 5 5 5 5 5 0 50 5 5 5 5 5 5 0 tive derivative Example C 25 5 5 3 5 5 3 0 5 3 2 5 5 3 0 100 5 5 5 5 5 5 0 Triazine 5 5 5 5 5 5 0 tive derivative Example D 5 5 5 5 5 5 0 5 5 3 5 5 3 0 100 5 5 5 5 5 5 0 Triazine 50 5 5 5 5 5 5 0 tive derivative Example E 25 5 5 5 5 5 5 0 17 5 4 3 5 5 3 0 100 5 5 5 5 5 5 0 Triazine 50 5 5 5 5 5 5 0 t i ve der i vat i ve Example F 25 5 5 5 5 5 5 0 18 5 3 4 5 5 3 0 76 Utilizability in industry The triazine derivative of the present invention is a novel compound and can be efficiently utilized as a The herbicide of the present invention with the said triazine derivative as the effective ingredient as compared with conventional herbicides for upland excellent herbicidal effects against weeds including troublesome weeds without causing phytotoxicity to upland crops in a remarkably high effect can be obtained by the treatment to the soil before preemergence or by the treatment to foliage in the fields of crops belonging to Gramineous the herbicides of the present invention exhibit higher effectiveness against troublesome weeds still with less phytotoxicity than hitherto known herbicides for paddy 77 a 4 B C 07 D 4C A 01 N H C 07 D 4 C 7 SB Λ 3TS 1 λ ft ft δ X l ft X ft 1 ft X ft 3 6 l 4 1 ΐ ffl l 2S ft X ft 1 ft X ft 1 X5 li η 1 2t ΐ 7 ϊ ft ft 1 4 7 ft ft i 4 7 2S t y 4 g Jo x Φ ft A φ ft ft l 4 ro y ί ft δ ft ft 1 ft i y NH II A Φ X3 R li iiij E s ft 7 ft A COX A Φ ft ft NH NH 1 ΐ Λ 3 6 7 δ X3 ft ft 2 5 X li X tt fi E i iai ft 7 at ft ft Φ Si 25 ft tt K A C ί A Φ ft l ift Φ Sij E l 4 7 Φ fc R ft ft i 4 ro 7 t t i 4 7 ft l ft 1 4 6 7 ί E i y i 4 ft 1 7 H 1 X 1 4 ft 1 ί D δ 4 4 X to ft ft ft 1 4 7 to Φ r t δ li ft A R li Si E PI C ft x ft ι ro 7 ft 4 7 4 7 1 y ϊ δ li ft X ft 1 A l 4 X R5 li PI a ft x ft δ 7 t i t A ft Φ i PI ft X ft 1 4 c t ft ft 1 4 7 a y li ft X ft 4 y 7 ft A li ft X ft 1 4 7 to a li ft ft 1 4 y a 7 to ft X ft 4 7 NH a δ li ft X ft 1 4 7 R3 li li X n ft X ft 1 4 a r A Φ v x3 PI ft X ft 1 4 ft X ft 3 6 C 7 T i X3 y A Φ X X ft 1 4 PJ tt R3 7 l n a 7 4 ί fc 3 n 2 4 7 7 7 7 7 7 7 a 7 ffi ft ft y r ft 2 r T ϊ s y 7 ίΐ 2 7 5 4 7 6 4 i ft If 2 3816419 f PI g n 4 4 ft It ft M Λ i 7 ft 1 4 7 ΐ l Silt 1 4 7 4 1 4 7 i X ft 1 4 7 ft 7 ft 3 4 D li lli ft 5 ro l 4 7 1 7 n ί 4 7 ft η η ft X J 4 Ms A Λ fi S5 R li i E C NH NH II II fc l i A I 7 3 It fc X E δ l 4 It S t I ί I 7 to Α Φ li E PI COX C Φ R4 X E t a n to SI ft A J ft A A Φ li mi E li Φ li E y a 4 Ύ a n l f S Jo t K i I C C 7 a s a τ 4 J ft δ 7 I 97 K X 7 7 7 β 7 x fc ft i Φ ε t PI I A ί I I I n i sec a ft X ft ft i y 7 1 S ft S3 A I a j ft X ί ft 4 7 a l 4 ft ft 1 4 7 δ C 4 1 4 7 S V a i 7 D Y a 7 A S y 7 6 y 7 β 2 5 7 s Y y 7 y 2 7 4 TO y 7 a ro 7 6 Y y D s Y y y y 2 7 4 A 4 l 4 7 i Y a 7 6 7 7 7 y 7 a As y 7 y 2 7 4 Y a 7 i 6 a Y 9 Y 7 D s Y y 7 y 2 7 S 4 a 7 4 3 4 7 6 7 s Y y 7 6 7 7 2 7 4 Y 4 A J 7 2 7 5 4 A a y 7 6 y 3 A A y D D s y 7 2 7 4 y C a y 2 7 4 Y 7 6 Y y s y 6 7 T 2 7 4 s 2 7 4 Y a y 7 6 D s y 7 2 7 y 4 7 ί 2 7 7 4 A C a Y y 7 6 y 7 s y 7 a Y T y 2 7 4 C 4 2 7 4 a 7 6 a a A 7 6 s y 7 y 2 7 5 Y 7 ί n s 7 2 4 Y 4 a Ϊ 4 C 3 y y 7 6 a a y A 7 s y 7 2 7 4 Y e 2 4 a i 7 A 7 6 β Y 7 4 s Y y 7 y 2 7 y 4 6 4 a 7 y A 7 4 6 a a β β Y s y 7 y 2 7 7 4 C 7 ί 6 4 7 ϊ y y 2 7 7 Af Y 4 A y 2 7 A 7 4 A 7 6 7 A A 6 s 7 2 7 A 7 4 7 6 α β β 7 A y 7 6 y 7 to 7 s y y 7 2 y 4 S 4 3 4 A to A y a 6 y to 7 i 6 a β β S y ί 4 to it to y 7 2 4 y 4 ΐ 4 A a 7 β J 7 6 β a 7 y 2 a to s 7 y 2 A to 4 7 7 6 A y 4 7 5 6 B A y to 7 s 7 4 y 2 to 4 7 6 A y to a y 7 y y 7 y 2 to y ΐ 4 4 A A 7 6 A A to y to 7 y to a 7 7 y 2 to 7 i s y 7 2 A 4 a to to 7 J 6 β 4 A to a A s 7 2 B 7 7 y 2 λ it ϊ 4 A t 4 7 7 6 to to a A 7 2 i 4 to 7 y y y 2 A 4 7 v y 4 6 i5 7 i to 4 y a A to y 7 4 7 7 i 6 y y 7 y 2 9 4 4 J ί i V 4 A y 7 2 4 7 7 a 7 s y 7 y to to s y y E I y y 7 4 7 7 6 s X 7 2 4 n v 4 i A y A to ifttt b ft y 7 7 s 7 y 7 7 y 6 ίίι y y i7 7 1 s y 7 y 2 S S C 6 I ft y 7 y 7 y β n 1 y 7 y i 4 7 SB I φ co ft 1 Π f 3 A X li 22 C r tj CO y ft b A ft y A cox r A r A n a X r r s y 7 S y ii co ft co 4 y Π 3 Φ co K Si ft ft 82 I A r y ft co β K R a y 7 y ft co ft if CO y A T y co 7 y s ft s co A li E PI n 4 y r S n 4 ff n K n 150 200 A co to A A li E PI A PI y 7 y ft ί ft A 4 4 tR1 X E PI S s n y co 7 ro K i n fit m A XI A 1 y 7 y ft 4 y c n n y X ira ft E y K T tt ft ft D A i ft S 2 4 2 7 s l τ i ro 7 4 n ft 4 y 7 y li ft v s 4 a S2 A y 7 y ffl τ C ft CO A 9 y 9 y z ft ft a ffl fc t D y IB I 1 i i Ι z 7 y a 7 4 ft s a y 4 y 200 A t s n 4 I I v i i I 7 y y y y χ a 9 y t loo X ft I A K 80 K it ff i li A I 4 A Ι y I I ί y y y 5 y y ft 1 I fc ft 5 y δ Ι 7 7 5 9 I x n 7 7 t I 4 It χ I i 7 a X ft in a r a a a 7 t ft K x y y y ft l 5 li V 7 t 7 ft to t ft n if 7 7 T ft C I A I I c I if I δ Y y r y n s n y 7 ft ft S 23 to y S ft ft 100 it if tt ft JR A I s y ft If I I ί 4 i δ fi 7 e 5 y W I I I 1 a t tf a ft y y 7 ft I i Ύ r v a ffl a y 7 ft ft ft 80 xf m 4 n ftfi ft i τ Z tt to n ft i i i y 7 y tt 7 y 55S 9 fc t ffl A ft 60 ft y y 5 6 ra y y Λ y ft fi ft y y ft r v 7 S y v s a r ί Hi tt K C S δ I ift ft 7 S A li t i t y t X ft i f I n 3 a As is 7 ί f 50 is 7 9 7 T 50 is 9 150 ΐ ft 1i ft 5 T i i 3 4 a As y ί 7 It 18 1 K 3 4 n ft y ffl fc 1 a ft a 7 a 1 3S Ά 1 fc 10 ί i 2 5 ι o y in y χ ί x τ 3 2 x 10 i y 4 ί r ft ft 2 7 χ ι 5 T 3 C 10 y T 2 M 6 12 a T 3 4 S K i a ft A x ffi 5 a fc y PI 6 4 l 3S 2 K 2 T 4 21 i 7 6 3 4 a y ί 7 2 K t a a 7 tr x 5 y t y S ί κ 2 2 X 3 3 s 21 22 Ώ 4 I i 29 4 7 6 3 C 10 i ΐ s y y C 205 ffl Ι ft g 10 T ft fc n l ί j 5 Il i t 7 s ft 30 T fi r 2 f 4 i i 1 t fc 6 C J D y 7 s y 7 lo K t y ft S 8 2 Λ SE T S i t fc ft 4 S i ft Si f f 4 7 f 7 ft fc 6 ft f 7 s y y ft t 7 fc s fc ffl 4 fe i 4 K 5 7 6 C 3 4 y 7 s 7 v C ft a 2 6 3 s 7 y C ft t JSC fc W tt K i n 5 W 39 2i 37 4 i 4 St I 4 C 30 y 7 G i ft ffl I a 3 7 4 K 5 K lO i ϊ 4 i V 7 t sa Ιβ y 2 4 7 S 6 4 ft 9 y 7 y ft y X it ft 4 C Λ S 7 2 4 7 8 y 4 7 7 ft ft 4 4 X 4 a 1 41 v a a a i Τ fi i 107 fc fc fc τ fc e ft I S 0 100 1 95 2 90 94 3 80 89 4 80 79 5 50 69 7 a K t c 0 100 1 99 tt ί i 2 21 60 s m a fc 3 11 20 4 1 10 5 0 it 1 7 ffl fc Ά ML 1 fc 7 ft A 6 n 2 7 β a s 7 y y y K i fc y 7 fc i tt ft l tt D ΐ fc n 2 7 4 7 it 2 y 1 S a a fc y 7 3816419 S fc t ft IE B fc n 2 i 6 7 49 8261 ffl fc w 1 tt ro tt tt fc A s K s 3 1 a i a fc y 7 ft y K T IE C B n 2 7 6 NHCHi a a 7 s y 6 6 6 6 6 insufficientOCRQuality

Claims (2)

94727/2 C L A I M

1. Λ Lriazine derivative represented by the general formula In the formula Y2 and Y3, which can be of the same kind or erent k nds, each denotes a methyl group or a methoxy group) or , (·γ 4 , η · ζτλ o C H (in which Y4 denotes a methyl group, trifluoromethyl group, methoxy group or fluorine atom and n denotes an integer of 0 to 2), X 1 denotes a halogen" atom and R1 denotes hydrogen, a methyl group or an ethyl group]. herbicidal composition

2. Λ horbioido containing, as an effective ingredient, a triazine derivative represented by the general formula [in the form (in whicn Y2 and Y3, which can be of the same kind or different kinds) - 70 - 94727/2 each denotes a methyl group or a methoxy group) or (in which denotes a methyl group, trifluoromethyl group, methoxy group or fluorine atom and n denotes an integer of 0 to 2), X1 denotes a halogen atom, and R denotes hydrogen, a methyl group or an ethyl group]. - 79 -