Triazine derivative and a herbicide comprising the same as an effective ingredient

Description

FIELD OF TECHNOLOGY
The present invention relates to novel triazine derivatives and a herbicide containing the derivatives as an effective ingredient.
1. Background Technology
A variety of herbicides have been hitherto developed and contributed to the productivity and labor-saving in agriculture. However, 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 weeds. It is also desired to develop a high-activity herbicide in order to overcome the problem of environmental pollution by conventional herbicides. In order to overcome to the problem of the ununiform germination of weeds over a long period of time, furthermore, 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 pregermination stage to the growing period of weeds.
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 phytotoxicity to paddy rice and arrived at a discovery that a herbicide containing a triazine compound as an effective ingredient is effective (official publication of Japanese Patent Toku-sai-hyo 88/02368, official publication of Japanese Patent Kokai 63-146876, official publication of Japanese Patent Kokai 63-51379 and official publication of Japanese Patent Kokai 63-264465). This triazine-based herbicide is highly active against troublesome weeds in paddy rice field at low dosage without phytotoxicity to paddy rice plant. This herbicide also shows excellent herbicidal activity against troublesome weeds by foliage application in upland field without phytotoxicity to Gramineous crops.
Nevertheless, this herbicide shows somewhat limited performance by preemergence treatment to the soil in upland fields.
2. Disclosure Of The Invention
The present invention provides:
(1) a triazine derivative represented by the general formula ##STR5## in the formula, A denotes ##STR6## (in which Y.sup.1 denotes a hydrogen atom or a methyl group and Z denotes an oxygen atom or a sulfur atom), ##STR7## (in which Y.sup.2 and Y.sup.3, which can be of the same kind or different kinds, each denote a methyl group or a methoxy group) or ##STR8## (in which Y.sup.4 denotes a methyl group, trifluoromethyl group, methoxy group or fluorine atom and n denotes an integer of 0 to 2), X.sup.1 denotes a halogen atom and R.sup.1 denotes hydrogen, a methyl group or an ethyl group , and
(2) a herbicide containing, as an effective ingredient, a triazine derivative represented by the general formula ##STR9## in the formula, A denotes ##STR10## in which Y.sup.1 denotes a hydrogen atom or a methyl group and Z denotes an oxygen atom or a sulfur atom), ##STR11## (in which Y.sup.2 and Y.sup.3, which can be of the same kind or different kinds, each denote a methyl group or a methoxy group) or ##STR12## (in which Y.sup.4 denotes a methyl group, trifluoromethyl group, methoxy group or fluorine atom and n denotes an integer of 0 to 2), X.sup.1 denotes a halogen atom and R.sup.1 denotes hydrogen, a methyl group or an ethyl group.
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 fields. As a result, a discovery has been reached that those having a specific haloalkyl group are effective leading to completion of the present invention.
The triazine derivative of the present invention is a novel compound and can be effectively utilized as a herbicide. When used as a herbicide for upland fields, 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 crops. In particular, a remarkably high effect is obtained by the soil treatment or treatment to foliage in non-paddy fields of crops belonging to Gramineous crops. As compared with existing herbicides for paddy rice, in addition, the herbicide of the present invention has a high chemical effect against hardly eliminable weeds still with little phytotoxicity.
BEST MODE TO PRACTICE THE INVENTION
The present invention provides a triazine derivative represented by the general formula ##STR13## in the formula, A denotes ##STR14## (in which Y.sup.1 denotes a hydrogen atoms or a methyl group and Z denotes an oxygen atom or a sulfur atom), Y.sup.3 ##STR15## (in which Y.sup.2 and Y.sup.3, which can be of the same kind or of different kinds, each denote a methyl group or a methoxy group) or ##STR16## (in which Y.sup.4 denotes a methyl group, trifluoromethyl group, methoxy group or fluorine atom and n denotes an integer of 0 to 2), X.sup.1 denotes a halogen atom and R.sup.1 denotes hydrogen, a methyl group or an ethyl group and also provides a herbicide containing the triazine derivative represented by the above given general formula [I].
The triazine derivative of the present invention represented by the above given general formula [I] can be prepared by various different methods. The method of preparation with the highest efficiency among them is the method to react an alkyl amine salt represented by the general formula ##STR17## in the formula, A is the same as given above and X.sup.3 denotes a halogen atom and cyanoguanidine expressed by the formula ##STR18## to prepare an alkyl biguanide salt represented by the general formula ##STR19## in the formula, A and X.sup.3 are each the same as given above] and then to react the alkyl biguanide salt with an alkyl ester represented by the general formula ##STR20## in the formula, R.sup.1 and X.sup.1 are each the same as given above and R.sup.2 denotes an alkyl group having 1 to 4 carbon atoms . In this manner, the alkyl amine salt represented by the general formula [II] and cyanoguanidine are reacted to give the alkyl biguanide salt represented by the general formula [III] which is reacted with the alkyl ester represented by the general formula [IV] to give the desired triazine derivative represented by the general formula [I] in high efficiency.
In conducting the reaction between the alkyl amine salt represented by the above given general formula [II] and cyanoguanidine here, these two compounds can be used in an approximately equimolar proportion and usable solvents include cyclic hydrocarbons such as benzene, Decalin, alkyl naphthalenes and the like and chlorinated hydrocarbons such as carbon tetrachloride, ethylene dichloride, chlorobenzene, dichlorobenzene, trichlorobenzene and the like. And, the reaction temperature is not particularly limitative and sufficient proceeding can be obtained in the range from low to high temperatures or, in particular, from 80.degree. to 200.degree. C.
The salt of an alkyl biguanide derivative represented by the general formula [III] is obtained by this reaction and, in the method of the present invention, this is reacted with the alkyl ester of the general formula [IV] ##STR21## to prepare the desired triazine derivative represented by the general formula [I]. This reaction usually proceeds in high efficiency at about 10.degree. to 100.degree. C. in the presence of a catalyst such as a base and the like in a solvent such as alcohols, e.g., methanol, ethanol, isopropanol and the like, various kinds of ketones, aliphatic hydrocarbons, various kinds of ethers, various kinds of cyclic hydrocarbons, chlorinated hydrocarbons and the like.
The triazine derivatives of the general formula [I] obtained by the above described method are novel compounds.
And, 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 synthesis. The compound of the present invention can be used as a herbicide either in the form of the racemic modification or in the form of the isolated optical isomer. Furthermore, the compound of the present invention also can be used as a herbicide in the form of a salt of an inorganic acid or organic acid.
Furthermore, the triazine derivative represented by the general formula [I] inhibits germination and growth of weeds and has high selectivity so that it is satisfactory as a herbicide. In addition, it is useful not only for the soil treatment 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 treatment. The triazine derivative of the present invention exhibits no phytotoxicity to the crops belonging to Gramineous crops such as corn, grain sorghum, wheat, barley, 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 L., Ipomoea purpurea, Abutilon theophrasti, Galium sparium var. echinospermon, Stellaria media, Veronica persica, Polygonum persicaria, Viola arvensis, Brassica juncea, Amaranthus patulus, Common blackjack and the like and strongly harmful weeds belonging to the family of Graminea such as Digitaria sanguinalis, Alopecurus myosuroides and the like.
Furthermore, this triazine derivative not only exhibits a prominent herbicidal effect against broadleaf weeds such as Rotala indica (Willd) Koehne var. uligirosa (Miq.) Koehne, Lindernia pyxidaria L., Monochoria vaginalis Presl var. plantaginea and the like, weeds belonging to the family of Cyperaceae such as Cyperus difformis L. and the like and weeds belonging to the family of Gramineae such as Echinochloa crus-galli P. Beauv. var. formosensis Ohwi and the like but also exhibits a prominent herbicidal effect against perennial weeds such as Scirpus juncoides Roxb. ssp. Hotarui Ohwi T. Koyama, Cyperus serotinus Rottb., Sagittaria pygmaea Miq. and the like, which are currently deemed to be hardly eliminable, without causing chemical damages against paddy rice.
In the next place, the herbicide of the present invention contains the above described compound or, namely, the triazine derivative represented by the general formula [I] as the effective ingredient and these compounds can be used as being prepared in the preparation form such as a water-dispersible powder, emulsion, dust, granules, flowable agent, solution and the like by mixing with a liquid carrier such as solvents and the like or a solid carrier such as mineral fine powders and the like. In the preparation of the form, it is optional according to need to add an emulsifying agent, dispersion aid, spreading agent, suspending agent, penetrating agent, stabilizer and other adjuvants.
When the herbicide of the present invention is used in the form of a water-dispersible powder, usually, a composition to be used is prepared by compounding from 10 to 55% by weight of the above described triazine derivative of the present invention as the effective ingredient, from 40 to 88% by weight of a solid carried and from 2 to 5% by weight of a surface active agent. Further, when it is used in the form of an emulsion or a flowable agent, it can be usually prepared by compounding from 5 to 50% by weight of the triazine derivative of the present invention as the effective ingredient, from 35 to 90% by weight of a solvent and a surface active agent and from to 15% by weight of other adjuvants.
When it is used in the form of a dust, on the other hand, it can be prepared usually by compounding from 1 to 15% by weight of the triazine derivative of the present invention as the effective ingredient and from 85 to 99% by weight of a solid carrier. When it is used in the form of granules, furthermore, they can be prepared usually by compounding from 0.1 to 15% by weight of the triazine derivative of the present invention as the effective ingredient, from 80 to 97.9% by weight of a solid carrier and from 2 to 5% by weight of a surface active agent. The solid carrier used here is a fine mineral powder and such a fine mineral powder includes diatomaceous earth, oxides such as hydrated lime and the like, phosphates such as apatite and the like, sulfates such as gypsum and the like, silicates such as talc, pyrophyllite, clay, kaolin, bentonite, acid clay, white carbon, quartz powder, silica stone powder and the like, and so on.
And, the liquid carrier includes organic solvents such as paraffinic or naphthenic hydrocarbons, e.g., kerosine, mineral oil, spindle oil and the like, aromatic hydrocarbons, e.g., benzene, toluene, xylene and the like, chlorinated hydrocarbons, e.g., 2-chlorotoluene, trichloromethane, trichloroethylene and the like, alcohols, e.g., cyclohexanol, amyl alcohol, ethylene glycol and the like, alcohol ethers, e.g., ethylene glycol monomethyl ether, ethylene glycol monoethyl ether and the like, ketones, e.g., isophorone, cyclohexanone, cyclohexenyl cyclohexanone and the like, ethers, e.g., Butyl Cellosolve, dimethyl ether, methyl ethyl ether and the like, esters, e.g., isopropyl acetate, benzyl acetate, methyl phthalate and the like, amides e.g., dimethyl formamide and the like, nitriles, e.g., acetonitrile, propionitrile and the like, and sulfoxides, e.g., dimethyl sulfoxide and the like as well as mixtures thereof, water and the like.
Further, as the surface active agent, any one can be used among the anionic type ones (alkylbenzene sulfonates, alkyl sulfonates, lauric acid amide sulfonate and the like), nonionic type ones (polyoxyethylene octyl ether, polyethylene glycol laurate, sorbitan alkyl esters and the like), cationic type ones (dimethyl lauryl benzyl ammonium chloride, lauryl amine, stearyl trimethyl ammonium chloride and the like) and amphoteric type ones (amino acids, betaine and the like).
Further, 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 alginate, carboxymethyl cellulose, carboxy vinyl polymer, gum arabic, hydroxypropyl methyl cellulose and the like.
The above described triazine derivative of the present invention as a novel compound represented by the general formula [I] exhibits an excellent effect as a high-selectivity herbicide not causing any phytotoxicity for the crops in nonpaddy fields such as corn, grain sorghum, wheat, barley, oat and the like by the soil treatment or foliage treatment either before germination or after germination of weeds. And, 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 high-selecte herbicide not causing any phytotoxicity also for paddy rice.
The herbicide of the present invention is administered in a dose of approximately from 0.1 to 1000 g or, preferably, from 1 to 100 g per 10 ares as the effective ingredient. When it is applied on foliage of plants, it is administered as being diluted to about 1 to 10000 ppm or, preferably, to 10 to 1000 ppm.
Incidentally, it is optional to use the triazine derivative represented by the general formula [I] in combination with other herbicidal constituents as the effective ingredient of the herbicide of the present invention. Such an auxiliary herbicidal constituent can be a herbicide hitherto on the market including various ones exemplified, for example, by the phenoxy-type herbicides, diphenyl ether-type herbicides, triazine-type herbicides, urea-type herbicides, carbamate-type herbicides, thiol carbamate-type herbicides, acid anilide-type herbicides, pyrazole-type herbicides, phosphoric acid-type herbicides, sulfonyl urea-type herbicides, nitrile-type herbicides, dinitroaniline-type herbicides, imidazolinone-type herbicides, oxadiazone and the like.
Furthermore, the herbicide of the present invention can be used as mixture with insecticides, germicides, growth-controlling agents of plants, fertilizers and the like according to need.

EXAMPLES
In the following, the present invention is described in further detail by way of examples.
PREPARATION EXAMPLE 1
Sodium methoxide was produced by gradually adding 0.92 g (40 m moles) of sodium to 20 ml of dried methanol and 2-(3',5'-dimethylphenoxy) isopropyl biguanide hydrochloride (20 m moles) (described in the official publication of Japanese Patent Kokai No. 63-264465) as the starting material I was added thereto and agitated for 30 minutes at room temperature. In the next place, 4.80 ml (40 m moles) of ethyl ester of .alpha.-fluoro-.alpha.-methyl propionic acid as the starting material II were added dropwise and agitated for 10 hours at room temperature. After completion of the reaction, the content material was poured into 100 ml of water and subjected to three times of extraction with 50 ml of ethyl acetate. This ethyl acetate layer was dried with anhydrous sodium sulfate followed by removal of the ethyl acetate by distillation under reduced pressure. The residue was purified by the silica gel column chromatography (developing solvent: hexane/ethyl acetate=4/1) followed by recrystallization from hexane-ethyl ether to give white 2-amino-4-[2-(3',5'-dimethylphenoxy) isopropylamino]-6 -fluoroisopropyl-s-triazine (compound I). The produced amount, % yield, results of analysis, structural formula and others thereof are shown in Tables 1 to 3.
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 (described in the official publication of Japanese Patent Toku-Sai-Hyo No. 88/02368, official publication of Japanese Patent Kokai No. 63-51379 and official publication of Japanese Patent Kokai No. 63-264465) indicated in Table 1 in place of the 2-(3',5'-dimethylphenoxy) 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 .alpha.-fluoro-.alpha.-methyl propionic acid as the starting material II. The produced amounts, % yields, results of analysis, structural formulas and others of these compounds are shown in Tables 1 to 3.
TABLE 1__________________________________________________________________________ Results of Analysis (%)Preparation Melting ElementaryExample No. Starting Materials Yield Yield Point Analysis (%)(Compound No.) I II (g) (%) (.degree.C.) C H N__________________________________________________________________________Preparation 2-(3',5'-dimethyl- .alpha.-fluoro, .alpha.-methyl 2.53 38 102.4- 53.9 7.3 21.0Example 1 phenoxy)-1-methyl- propionic acid 104.9 (61.2) (7.3) (21.0)(Compound ethyl biganide ethyl esterNo. 1)Preparation 2-(3',5'-dimethyl- .alpha.-fluoro-propionic 0.83 13 Color- 60.0 7.1 22.3Example 2 phenoxy)-1-methyl- acid n-butyl less, (60.2) (6.9) (21.9)(Compound ethyl biganide ester resinousNo. 2)Preparation 2-(3',5'-dimethyl- .alpha.-chloro- 1.61 24 Color- 56.2 6.7 21.2Example 3 phenoxy)-1-methyl- propionic acid less, (57.2) (6.6) (20.9)(Compound ethyl biganide methyl ester resinousNo. 3)Preparation 2-(2',5'-dimethyl- .alpha.-fluoro, .alpha.-methyl 2.80 42 134.5- 60.9 7.1 21.2Example 4 phenoxy)-1-methyl- propionic acid 136.0 (61.2) (7.3) (21.0)(Compound ethyl biganide ethyl esterNo. 4)Preparation 2-(2',3'-dimethyl- .alpha.-fluoro, .alpha. -methyl 2.27 34 Color- 63.0 7.4 21.1Example 5 phenoxy)-1-methyl- propionic acid less, (61.2) (7.3) (21.0)(Compound ethyl biganide ethyl ester resinousNo. 5)Preparation 2-(2',5'-dimethyl- .alpha.-chloro, .alpha.-methyl 1.06 15 Color- 59.0 6.7 20.4Example 6 phenoxy)-1-methyl- propionic acid less, (58.4) (6.9) (20.0)(Compound ethyl biganide ethyl ester resinousNo. 6)Preparation 2-(2',3'-dimethyl- .alpha.-chloro, .alpha.-methyl 0.82 12 Color- 58.0 7.2 19.6Example 7 phenoxy)-1-methyl- propionic acid less, (58.4) (6.9) (20.0)(Compound ethyl biganide ethyl ester resinousNo. 7)Preparation 2-(2',3'-dimethyl- .alpha.-fluoro-propionic 0.48 8 Color- 60.0 6.9 22.3Example 8 phenoxy)-1-methyl- acid n-butyl ester less, (60.2) (6.9) (21.9)(Compound ethyl biganide resinousNo. 8)Preparation 2-(3',5'-dimethyl- .alpha.-chloro, .alpha.-methyl 2.01 29 Color- 57.9 7.0 20.2Example 9 phenoxy)-1-methyl- propionic acid less, (58.4) (6.9) (20.0)(Compound ethyl biganide ethyl ester resinousNo. 9)Preparation 2-(3',5'-dimethyl- .alpha.-bromo, .alpha.-methyl 1.85 24 Color- 52.2 6.0 17.5Example 10 phenoxy)-1-methyl- propionic acid less, (51.8) (6.1) (17.8)(Compound ethyl biganide ethyl ester resinousNo. 10)Preparation 2-(3'-trifluoro- .alpha.-fluoro, .alpha.-methyl 2.09 28 Color- 51.9 5.0 18.4Example 11 methylphenoxy)-1- propionic acid less, (51.5) (5.1) (18.8)(Compound methyl-ethyl ethyl ester resinousNo. 11) biganidePreparation 2-(3'-methyl .alpha.-fluoro, .alpha.-methyl 1.32 21 95.3- 60.0 6.8 22.2Example 12 phenoxy)-1-methyl propionic acid 97.0 (60.2) (6.9) (21.9)(Compound ethyl biganide ethyl esterNo. 12)Preparation 2-(3'-methyl .alpha.-fluoro-propionic 0.45 7 Color- 59.2 6.9 22.5Example 13 phenoxy)-1-methyl acid n-butyl ester less, (59.0) (6.6) (22.9)(Compound ethyl biganide resinousNo. 13)Preparation 2-(3'-trifluoro- .alpha.-fluoro-propionic 1.09 15 Color- 50.5 4.5 19.9Example 14 methylphenoxy)-1- acid n-butyl ester less, (50.1) (4.8) (19.5)(Compound methyl-ethyl resinousNo. 14) biganidePreparation 2-(3'-methyl .alpha.-chloro, .alpha.-methyl 1.11 16 Color- 57.0 6.9 20.5Example 15 phenoxy)-1-methyl propionic acid less, (57.2) (6.6) (20.9)(Compound ethyl biganide ethyl ester resinousNo. 15)Preparation 2-phenoxy .alpha.-chloro, .alpha.-methyl 1.04 16 Color- 56.4 6.1 22.0Example 16 1-methyl-ethyl propionic acid less, (56.0) (6.3) (21.8)(Compound biganide ethyl ester resinousNo. 16)Preparation 2-phenoxy .alpha.-fluoro, .alpha.-methyl 1.64 27 Color- 58.7 6.8 23.1Example 17 1-methyl-ethyl propionic acid less, (59.0) (6.6) (22.9)(Compound biganide ethyl ester resinousNo. 17)Preparation 2-phenoxy .alpha.-fluoro-propionic 0.58 9.6 Color- 58.1 6.0 24.2Example 18 1-methyl-ethyl acid n-butyl ester less, (57.7) (6.1) (24.0)(Compound biganide resinousNo. 18)Preparation 2-(3'-methoxy- .alpha.-fluoro, .alpha.-methyl 1.42 21 Color- 56.9 6.8 20.7Example 19 phenoxy)-1-methyl propionic acid less, (57.3) (6.6) (20.9)(Compound ethyl biganide ethyl ester resinousNo. 19)Preparation 2-(3',4'-dimethyl- .alpha.-fluoro, .alpha.-methyl 0.61 9.2 Color- 60.8 6.9 21.3Example 20 phenoxy)-1-methyl propionic acid less, (61.2) (7.3) (21.0)(Compound ethyl biganide ethyl ester resinousNo. 20)Preparation 2-(3'-fluoro- .alpha.-fluoro, .alpha.-methyl 3.88 60 Color- 55.9 5.6 22.0Example 21 phenoxy)-1-methyl propionic acid less, (55.7) (5.9) (21.7)(Compound ethyl biganide ethyl ester resinousNo. 21)Preparation 2-(2'-fluoro- .alpha.-fluoro, .alpha.-methyl 0.19 3 Color- 56.0 6.2 21.5Example 22 phenoxy)-1-methyl propionic acid less, (55.7) (5.9) (21.7)(Compound ethyl biganide ethyl ester resinousNo. 22)Preparation 2-(4' -fluoro- .alpha.-fluoro, .alpha.-methyl 0.84 13 Color- 55.2 5.8 21.6Example 23 phenoxy)-1-methyl- propionic acid less, (55.7) (5.9) (21.7)(Compound ethyl biganide ethyl ester resinousNo. 23)Preparation 1-(benzofuran- .alpha.-fluoro, .alpha.-methyl 4.74 75 161.5- 60.7 5.9 22.5Example 24 2'-yl)ethyl propionic acid 162.4 (60.9) (5.8) (22.2)(Compound biganide ethyl esterNo. 24)Preparation 1-(benzofuran- .alpha.-chloro, .alpha.-methyl 5.64 85 138.8- 57.5 5.2 20.8Example 25 2'-yl)ethyl propionic acid 139.7 (57.9) (5.5) (21.1)(Compound biganide methyl esterNo. 25)Preparation 1-(benzofuran- .alpha.-bromo, .alpha.-methyl 5.56 74 149.8- 51.3 4.6 18.3Example 26 2'-yl)ethyl propionic acid 150.7 (51.1) (4.8) (18.6)(Compound biganide ethyl esterNo. 26)Preparation 1-(benzofuran- .alpha.-fluoro-propionic 2.84 47 139.0- 59.6 5.1 23.5Example 27 2'-yl)ethyl acid ethyl ester 140.2 (59.8) (5.4) (23.2)(Compound biganideNo. 27)Preparation 1-(benzofuran- .alpha.-chloro-propionic 5.02 79 145.3- 56.5 5.3 22.3Example 28 2'-yl)ethyl acid methyl ester 147.4 (56.7) (5.1) (22.0)(Compound biganideNo. 28)Preparation 1-(benzofuran- .alpha.-fluoro, .alpha.-methyl 3.20 48 153.9- 62.2 6.4 21.1Example 29 2'-yl)ethyl butyric acid 155.2 (62.0) (6.1) (21.3)(Compound biganide ethyl esterNo. 29)Preparation 1-(benzothiophen- .alpha.-fluoro, .alpha.-methyl 4.76 72 134.2- 58.2 5.3 20.9Example 30 2'-yl)ethyl propionic acid 136.0 (58.0) (5.5) (21.1)(Compound biganide ethyl esterNo. 30)Preparation 1-(benzothiophen- .alpha.-chloro, .alpha.-methyl 4.86 70 Color- 55.0 5.4 20.3Example 31 2'-yl)ethyl propionic acid less, (55.2) (5.2) (20.1)(Compound biganide methyl ester resinousNo. 31)Preparation 1-(benzothiophen- .alpha.-fluoro-propionic 2.28 36 Color- 57.0 4.9 22.5Example 32 2'-yl)ethyl acid ethyl ester less, (56.8) (5.1) (22.1)(Compound biganide resinousNo. 32)Preparation 1-(6'-methyl- .alpha.-fluoro, .alpha.-methyl 5.54 84 168.5- 62.4 6.0 21.1Example 33 benzofuran-2'-yl) propionic acid 169.3 (62.0) (6.1) (21.3)(Compound ethyl biganide ethyl esterNo. 33) hydrochloridePreparation 1-(6'-methyl- .alpha.-fluoro-propionic 3.28 52 Color- 61.2 5.6 22.0Example 34 benzofuran-2'-yl) acid ethyl ester less, (60.9) (5.8) (22.2)(Compound ethyl biganide resinousNo. 34) hydrochloridePreparation 1-(6'-methyl- .alpha.-chloro, .alpha.-methyl 5.18 75 Color- 58.7 5.8 20.4Example 35 benzofuran-2'-yl) propionic acid less, (59.0) (5.8) (20.3)(Compound ethyl biganide methyl ester resinousNo. 35) hydrochloridePreparation 2-(3'-methoxy, 4'- .alpha.-fluoro, .alpha.-methyl 2.17 34 115.1- 58.7 6.7 21.6Example 36 methylphenyl)-1- propionic acid 116.8 (60.2) (6.9) (21.9)(Compound methyl-ethyl ethyl esterNo. 36) biganide hydrochloridePreparation 2-(3'-methoxy, 4'- .alpha.-fluoro-propionic 1.34 22 Color- 57.3 6.5 22.8Example 37 methylphenyl)-1- acid n-butyl ester less, (59.0) (6.6) (22.9)(Compound methyl-ethyl resinousNo. 37) biganide hydrochloridePreparation 2-(3'-methoxy, 4'- .alpha.-chloro, .alpha.-methyl 2.42 36 Color- 57.4 6.7 20.6Example 38 methylphenyl)-1- propionic acid less, (57.2) (6.6) (20.9)(Compound methyl-ethyl ethyl ester resinousNo. 38) biganide hydrochloridePreparation 2-(3'-methyl, 4'- .alpha.-fluoro, .alpha.-methyl 1.98 31 Color- 60.3 6.8 22.2Example 39 methylphenyl)-1- propionic acid less, (60.2) (6.9) (21.9)(Compound methyl-ethyl ethyl ester resinousNo. 39) biganide hydrochloridePreparation 2-(3'-methyl, 4'- .alpha.-fluoro-propionic 1.22 20 Color- 59.1 6.9 22.7Example 40 methylphenyl)-1- acid n-butyl ester less, (59.0) (6.6) (22.9)(Compound methyl-ethyl resinousNo. 40) biganide hydrochloridePreparation 2-(3'-methyl, 4'- .alpha.-chloro, .alpha.-methyl 2.22 33 Color- 57.0 6.8 21.0Example 41 methylphenyl)-1- propionic acid less, (57.2) (6.6) (20.9)(Compound methyl-ethyl ethyl ester resinousNo. 41) biganide hydrochloride__________________________________________________________________________ *The value in the brackets shows the theoretical value.
TABLE 2__________________________________________________________________________ Molecular weight of triazineNo. Structural formula of triazine derivative derivative Triazine derivative__________________________________________________________________________Prepara- tion Example 1 ##STR22## C.sub.17 H.sub.24 N.sub.5 OF 333.4 2-amino-4-(.alpha.-fluoro, .alpha.-methyl ethyl)-6-[2-( 3',5'-dimethyl- phenoxy)-1-m ethyl-ethylamino]- s-triazin ePrepara- tion Example 2 ##STR23## C.sub.16 H.sub.22 N.sub.5 OF 319.4 2-amino-4-(.alpha.-fluoroeth yl)-6- [2-(3',5'-dimethylphe noxy)- 1-methyl-ethylamino]- s-triazinePrepara- tion Example 3 ##STR24## C.sub.16 H.sub.22 N.sub.5 OCl 2-amino-4-(.alpha.-chloroeth yl)-6- [2-(3',5'-dimethylphe noxy)-1- methyl-ethylamino]- s-triazinePrepara- tion Example 4 ##STR25## C.sub.17 H.sub.24 N.sub.5 OF 333.4 2-amino-4-(.alpha.-fluoro, .alpha.-methyl ethyl)-6-[2-( 2',3'-dimethyl- phenoxy)-1-m ethyl-ethylamino]- s-triazin ePrepara- tion Example 5 ##STR26## C.sub.17 H.sub.24 N.sub.5 OF 333.4 2-amino-4-(.alpha.-fluoro, .alpha.-methyl ethyl)-6-[2-( 2',5'-dimethyl- phenoxy)-1-m ethyl-ethylamino]- s-triazin ePrepara- tion Example 6 ##STR27## C.sub.17 H.sub.24 N.sub.5 OCl 2-amino-4-(.alpha.-chloro, .alpha.-methyl ethyl)-6-[2-( 2',5'-dimethyl phenoxy)-1-me thyl-ethylamino]- s-triazinePrepara- tion Example 7 ##STR28## C.sub.17 H.sub.24 N.sub.5 OCl 2-amino-4-(.alpha.-chloro, .alpha.-methyl ethyl)-6-[2-( 2',3'-dimethyl- phenoxy)-1-m ethyl-ethylamino]- s-triazin ePrepara- tion Example 8 ##STR29## C.sub.16 H.sub.22 N.sub.5 OF 319.4 2-amino-4-(.alpha.-fluoroeth yl)-6- [2-(2',3'-dimethylphe noxy)- 1-methyl-ethylamino]- s-triazinePrepara- tion Example 9 ##STR30## C.sub.17 H.sub.24 N.sub.5 OCl 2-amino-4-(.alpha.-chloro, .alpha.-methyl ethyl)-6-[2-( 3',5'-dimethyl- phenoxy)-1-m ethyl-ethylamino]- s-triazin ePrepara- tion Example 10 ##STR31## C.sub.17 H.sub.24 N.sub.5 OBr 2-amino-4-(.alpha.-bromo, .alpha.-methyl ethyl)-6-[2-( 3',5'-dimethyl- phenoxy)-1-m ethyl-ethylamino]- s-triazin ePrepara- tion Example 11 ##STR32## C.sub.16 H.sub.19 N.sub.5 OF.sub.4 373.4 2-amino-4-(.alpha.-fluoro, .alpha.-methyl ethyl)-6-[2-( 2',3'-trifluoro- methylpheno xy)-1-methyl-ethyl- amino]-s-triazinePrepara- tion Example 12 ##STR33## C.sub.16 H.sub.22 N.sub.5 OF 319.4 2-amino-4-(.alpha.-fluoro, .alpha.-methyl ethyl)-6-[2-( 3'-methylphenoxy)-1- methyl-ethylamino]-s-triazin ePrepara- tion Example 13 ##STR34## C.sub.15 H.sub.20 N.sub.5 OF 305.4 2-amino-4-(.alpha.-fluoroeth yl)-6- [2-(3'-methylphenoxy) -1- methyl-ethylamino]-s-tri azinePrepara- tion Example 14 ##STR35## C.sub.15 H.sub.17 N.sub.5 OF.sub.4 359.3 2-amino-4-(.alpha.-fluoroeth yl)-6- [2-(3'-trifluoromethy lphenoxy)- 1-methyl-ethylami no]-s-triazinePrepara- tion Example 15 ##STR36## C.sub.16 H.sub.22 N.sub.5 Cl 335.8 2-amino-4-(.alpha.-chloro, .alpha.-methyl ethyl)-6-[2-( 3'-methylphenoxy)- 1-methyl- ethylamino]-s-triazinePrepara- tion Example 16 ##STR37## C.sub.15 H.sub.20 N.sub.5 OCl 2-amino-4-(.alpha.-chloro, .alpha.-methyl ethyl)-6-(2-p henoxy-1-methyl- ethylamino) -s-triazinePrepara- tion Example 17 ##STR38## C.sub.15 H.sub.20 N.sub.5 OF 321.8 2-amino-4-(.alpha.-fluoro, .alpha.-methyl ethyl)-6-(2-p henoxy-1-methyl- ethylamino) -s-triazinePrepara- tion Example 18 ##STR39## C.sub.14 H.sub.18 N.sub.5 OF 291.3 2-amino-4-(.alpha.-fluoroeth yl)-6- (2-phenoxy-1-methyl-e thylamino)- s-triazinePrepara- tion Example 19 ##STR40## C.sub.16 H.sub.22 N.sub.5 O.sub.2 F 335.4 2-amino-4-(.alpha.-fluoro, .alpha.-methyl ethyl)-6-[2-( 3'-methoxyphenoxy)- 1-methyl-ethylamino]-s-triaz inePrepara- tion Example 20 ##STR41## C.sub.17 H.sub.24 N.sub.5 OF 333.4 2-amino-4-(.alpha.-fluoro, .alpha.-methyl ethyl)-6-[2-( 3',4'-dimethyl- phenoxy)-1-m ethyl-ethylamino]- s-triazin ePrepara- tion Example 21 ##STR42## C.sub.15 H.sub.19 N.sub.5 OF.sub.2 323.3 2-amino-4-(.alpha.-fluoro, .alpha.-methyl ethyl)-6-[2-( 3'-flurorphenoxy)- 1-methyl- ethylamino]-s-triazinePrepara- tion Example 22 ##STR43## C.sub.15 H.sub.19 N.sub.5 OF.sub.2 323.3 2-amino-4-(.alpha.-fluoro, .alpha.-methyl ethyl)-6-[2-( 2'-fluorophenoxy)- 1-methyl- ethylamino]-s-triazinePrepara- tion Example 23 ##STR44## C.sub.15 H.sub.19 N.sub.5 OF.sub.2 323.3 2-amino-4-(.alpha.-fluoro, .alpha.-methyl ethyl)-6-[2-( 4'-fluorophenoxy)- 1-methyl- ethylamino]-s-triazinePrepara- tion Example 24 ##STR45## C.sub.16 H.sub.18 N.sub.5 OF.sub.2 315.4 2-amino-4-[1-(benzofuran-2'- yl)ethylamino]-6-(.alpha.-f luoro, .alpha.- methyl ethyl)-s-triazinePrepara- tion Example 25 ##STR46## C.sub.16 H.sub.18 N.sub.5 OCl 2-amino-4-[1-(benzofuran-2'- yl)ethylamino]-6-(.alpha.-c hloro, .alpha.- methyl ethyl)-s-triazinePrepara- tion Example 26 ##STR47## C.sub.16 H.sub.18 N.sub.5 OBr 2-amino-4-[1-(benzofuran-2'- yl)ethylamino]-6-(.alpha.-b romo, .alpha.- methyl ethyl)-s-triazinePrepara- tion Example 27 ##STR48## C.sub.15 H.sub.16 N.sub.5 OF 301.3 2-amino-4-[1-(benzofuran-2'- yl)ethylamino]-6-(.alpha.-f luoroethyl)- s-triazinePrepara- tion Example 28 ##STR49## C.sub.15 H.sub.16 N.sub.5 OCl 2-amino-4-[1-(benzofuran-2'- yl)ethylamino]-6-(.alpha.-c hloroethyl)- s-triazinePrepara- tion Example 29 ##STR50## C.sub.17 H.sub.20 N.sub.5 OF 329.4 2-amino-4-[1-(benzofuran-2-' - yl)ethylamino]-6-(.alpha.- fluoro, .alpha.- methyl propyl)-s-triazinePrepara- tion Example 30 ##STR51## C.sub.16 H.sub.18 N.sub.5 SF 331.4 2-amino-4-[1-(benzothiophen- 2'-yl)ethylamino]-6-(.alpha .-fluoro, .alpha.-methyl ethyl)-s-triazinePrepara- tion Example 31 ##STR52## C.sub.16 H.sub.18 N.sub.5 SCl 2-amino-4-[1-(benzothiophen- 2'- yl)ethylamino]-6-(.alpha .-chloro, .alpha.- methyl ethyl)-s-triazinePrepara- tion Example 32 ##STR53## C.sub.15 H.sub.16 N.sub.5 SF 317.4 2-amino-4-[1-(benzothiophen- 2'- yl)ethylamino]-6-(.alpha .-fluoroethyl)- s-triazinePrepara- tion Example 33 ##STR54## C.sub.17 H.sub.20 N.sub.5 2-amino-4-[1-(6'-methylbenzo - furan-2'-yl)ethylamino]-6- (.alpha.-fluoro, .alpha.-methyl ethyl)-s- triazinePrepara- tion Example 34 ##STR55## C.sub.16 H.sub.18 N.sub.5 OF 315.4 2-amino-4-[1-(6'-methylbenzo furan- 2'-yl)ethylamino]-6-( .alpha.-fluoro- ethyl)-s-tri azinePrepara- tion Example 35 ##STR56## C.sub.17 H.sub.20 N.sub.5 OCl 2-amino-4-[1-6'-methylbenzof uran- 2'-yl)ethylamino]-6-(. alpha.-chloro, .alpha.-methy l ethyl)-s-triazinePrepara- tion Example 36 ##STR57## C.sub.16 H.sub.22 N.sub.5 OF 319.4 2-amino-4-[.alpha.-fluoro, .alpha.-methyl ethyl)-6-[2-( 3'-methoxy, 4'- methylphenyl)-1-methyl- thylamino]-s-triazinePrepara- tion Example 37 ##STR58## C.sub.15 H.sub.20 N.sub.5 OF 305.4 2-amino-4-(.alpha.-fluoroeth yl)-6- [2-(3'-methoxy, 4'-methylphenyl)- 1-methyl-e thylamino]-s-triazinePrepara- tion Example 38 ##STR59## C.sub.16 H.sub.22 N.sub.5 OCl 2-amino-4-(.alpha.-chloro, .alpha.-methyl)- 6-[2-(3'-me thoxy, 4'-methylphenyl)- 1-methyl-ethylamino]-s-triaz inePrepara- tion Example 39 ##STR60## C.sub.16 H.sub.22 N.sub.5 OF 319.4 2-amino-4-(.alpha.-fluoro, .alpha.-methyl ethyl)-6-[2-( 3'-methyl, 4'- methoxyphenyl)-1-methyl- ethylamino]-s-triazinePrepara- tion Example 40 ##STR61## C.sub.15 H.sub.20 N.sub.5 OF 305.4 2-amino-4-(.alpha.-fluoroeth yl)-6- [2-(3'-methyl, 4'-methoxyphenyl)- 1-methyl- ethylamino]-s-triazinePrepara- tion Example 41 ##STR62## C.sub.16 H.sub.22 N.sub.5 OCl 2-amino-4-(.alpha.-fluoro, .alpha.-methylethyl)- 6-[ 2-(3'-methyl, 4'-methoxyphenyl)- 1-methyl- ethylamino]-s-triazine__________________________________________________________________________
TABLE 3__________________________________________________________________________Preparation Compound Infrared absorption*.sup.1Example No. prepared spectrum (cm.sup.-1) Proton nuclear magnetic resonance spectrum*.sup.2 (ppm)__________________________________________________________________________ 1 Compound 1 3470, 3350, 3280 1.35(3H, d), 1.65(6H, d), 2.28(6H, s), 3.91.about.3.99(2H, m), 1660, 1620, 1560 4.25.about.4.70(1H, brs), 5.44.about.5.80(3H, brs), 6.55.about.6.60(3H, m) solvent: deuterated chloroform 2 Compound 2 3500, 3440, 3200 1.33(3H, d), 1.60(3H, q), 2.26(6H, s), 3.90.about.4.03(2H, m), 1660, 1620, 1560 4.30.about.4.63(1H, brs), 4.80.about.5.14(1H, m), 5.38.about.5.77(3H, m), 6.52.about.6.60(3H, m) solvent: deuterated chloroform 3 Compound 3 3500, 3420, 3330 1.32(3H, d), 1.70(3H, d), 2.23(6H, s), 3.80.about.4.18(2H, m), 1660, 1620, 1560 4.32.about.4.80(3H, m), 6.50.about.6.60(4H, brs), solvent: deuterated acetone 4 Compound 4 3510, 3350, 3200 1.38(3H, d), 1.55(3H, d), 2.10(3H, s), 2.23(3H, s), 3.80.about. 1660, 1620, 1560 4.21(2H, m), 4.30.about.4.78(2H, brs), 6.18.about.7.42(6H, brs) solvent: deuterated acetone 5 Compound 5 3470, 3350, 3250 1.37(3H, d), 1.63(6H, d), 2.17(3H, s), 2.30(3H, s), 3.96.about. 1658, 1586, 1540 4.00(2H, m), 4.32.about.4.78(1H, brs), 5.26.about.5.73(3H, brs), 6.62.about.7.35(3H, m) solvent: deuterated chloroform 6 Compound 6 3530, 3360, 3250 1.40(3H, d), 1.88(6H, s), 2.19(3H, s), 2.31(3H, s), 3.96.about. 1650, 1580, 1575 4.03(2H, m), 4.32.about.4.80(1H, brs), 5.32.about.5.92(3H, brs), 6.54.about.7.22(3H, m) solvent: deuterated chloroform 7 Compound 7 3500, 3350, 3200 1.39(3H, d), 1.88(6H, s), 2.16(3H, s), 2.27(3H, s), 3.91.about. 1650, 1590, 1560 4.01(2H, m), 4.28.about.4.82(1H, brs), 5.28.about.5.88(3H, brs), 6.64.about.7.29(3H, m) solvent: deuterated chlorofrom 8 Compound 8 3530, 3360, 3220 1.38(3H, d), 1.62(3H, q), 2.14(3H, s), 2.28(3H, s), 3.95.about. 1660, 1580, 1560 4.00(2H, m), 4.32.about.4.75(1H, brs), 4.87.about.5.57(4H, brs), 6.64.about.7.20(3H, m) solvent: deuterated chloroform 9 Compound 9 3460, 3350, 3200 1.35(3H, d), 1.89(6H, s), 2.30(6H, s), 3.88.about.4.05(2H, m), 1660, 1620, 1550 4.24.about.4.72(1H, brs), 5.16.about.5.77(3H, brs), 6.42.about.6.79(3H, m) solvent: deuterated chloroform10 Compound 10 3500, 3360, 3200 1.37(3H, d), 2.08(6H, s), 2.29(6H, s), 3.84.about.4.07(2H, m), 1640, 1600, 1560 4.26.about. 4.77(1H, brs), 5.08.about.5.77(3H, brs), 6.44.about.6.75(3H, m) solvent: deuterated chloroform11 Compound 11 3530, 3360, 3200 1.37(3H, d), 1.63(6H, d), 3.93.about.4.09(2H, m), 4.27.about.4.72 1600, 1580, 1560 (1H, brs), 5.52.about.6.60(3H, brs), 7.02.about.7.48(4H, m) solvent: deuterated chloroform12 Compound 12 3440, 3330 1.36(3H, d), 1.64(6H, d), 2.32(3H, s), 3.94.about.4.01(2H, m), 1650, 1610, 1570 4.29.about.4.65(1H, brs), 5.28.about.5.90(3H, brs), 6.74.about.7.17(4H, m) solvent: deuterated chloroform13 Compound 13 3500, 3340, 3190 1.36(3H, d), 1.62(3H, q), 2.32(3H, s), 3.94.about.4.00(2H, m), 1640, 1620, 1564 4.19.about.4.70(1H, brs), 4.96(1H, q), 5.17.about.5.99(3H, brs), 6.68.about.7.24(4H, m) solvent: deuterated chloroform14 Compound 14 3500, 3350, 3200 1.36(3H, d), 1.62(3H, q), 3.98.about.4.08(2H, m), 4.29.about.4.70 1640, 1600, 1560 (1H, brs), 4.97(1H, q), 5.39.about.6.50(3H, brs) solvent: deuterated chloroform15 Compound 15 3500, 3350, 3230 1.35(3H, d), 1.88(6H, s), 2.32(3H, s), 3.94.about.4.01(2H, m), 1655, 1600, 1575 4.23.about.4.77(1H, brs), 5.09.about.5.99(3H, brs), 6.68.about.7.16(4H,m) solvent: deuterated chloroform16 Compound 16 3500, 3360, 3220 1.33(3H, d), 1.89(6H, s), 3.97.about.4.04(2H, m), 4.26.about. 4.76 1655, 1600, 1460 (1H, brs), 4.96.about.5.73(3H, brs), 6.87.about.7.38(5H, m) solvent: deuterated chloroform17 Compound 17 3500, 3380, 3180 1.34(3H, d), 1.63(6H, d), 3.93.about.4.01(2H, m), 4.18.about.4.70 1650, 1600, 1560 (1H, brs), 5.61.about.5.58(3H, brs), 6.84.about.7.36(5H, m) solvent: deuterated chloroform18 Compound 18 3510, 3350, 3200 1.34(3H, d), 1.60(3H, q), 3.88.about.4.00(2H, m), 4.25.about.4.73 1660, 1610, 1560 (1H, brs), 4.95(1H, q), 5.38.about.6.62(3H, brs), 6.83.about.7.36 (5H, m) solvent: deuterated chloroform19 Compound 19 3470, 3380, 3220 1.36(3H, d), 1.64(6H, d), 3.79(3H, s), 3.91.about.4.04(2H, m), 1650, 1610, 1575 4.28.about.4.65(1H, brs), 5.32.about.5.92(3H, brs), 6.48.about.7.17(4H, m) solvent: deuterated chloroform20 Compound 20 3440, 3330, 3200 1.33(3H, d), 1.62(6H, d), 2.17(3H, s), 2.21(3H, s), 3.89.about. 1650, 1595, 1560 3.96(2H, m), 4.20.about.4.67(1H, brs), 5.48.about.6.48(3H, brs), 6.57.about.7.12(3H, m) solvent: deuterated chloroform21 Compound 20 3440, 3330, 3240 1.35(3H, d), 1.64(6H, d), 3.93.about.4.03(2H, m), 4.26.about.4.67 1640, 1585, 1560 (1H, brs), 5.22.about.5.92(3H, brs), 6.59.about.7.37(4H, m) solvent: deuterated chloroform22 Compound 22 3500, 3320, 3240 1.39(3H, d), 1.64(6H, d), 4.01.about.4.10(2H, m), 4.29.about.4.72 1650, 1600, 1570 (1H, brs), 5.07.about.5.74(3H, brs), 6.99.about.7.02(4H, m) solvent: deuterated chloroform23 Compound 23 3520, 3350, 3220 1.36(3H, d), 1.64(6H, d), 3.91.about.3.99(2H, m), 4.23.about.4.74 1660, 1600, 1560 (1H, brs), 5.13.about.5.68(3H, brs), 6.86.about.6.98(4H, m) solvent: deuterated chloroform24 Compound 24 3500, 3310, 3220 1.56(6H, d), 1.65(3H, d), 5.30.about.5.71(1H, m), 6.20.about.6.59 1660, 1600, 1540 (2H, brs), 6.69(1H, s), 7.12.about.7.64(4H, m) solvent: deuterated acetone25 Compound 25 3490, 3340, 3270 1.62(3H, d), 1.89(6H, s), 5.25.about.5.78(1H, m), 6.57(1H, s), 1640, 1610, 1560 7.11.about.7.56(4H, m) solvent: deuterated acetone26 Compound 26 3490, 3350 1.63(3H, d), 2.07(6H, s), 5.24.about.5.77(1H, m), 6.57(1H, s), 1650, 1580, 1560 7.16.about.7.58(4H, m) solvent: deuterated acetone27 Compound 27 3490, 3320, 3190 1.60(3H, d, d), 1.61(3H, d), 4.90.about.5.42(1H, q, q), 5.40.about.6.08 1650, 1600, 1540 (1H, brs), 6.69(1H, s), 7.11.about.7.56(4H, m) solvent: deuterated acetone28 Compound 28 3490, 3320, 3220 1.57(3H, d), 1.72(3H, d), 4.69(1H, q), 5.24.about.5.73(1H, m), 1660, 1600, 1560 6.69(1H, s), 7.08.about.7.68(4H, m) solvent: deuterated acetone29 Compound 29 3460, 3320, 3180 1.20(3H, t), 1.57(3H, d), 1.65(3H, d), 1.88(1H, q), 5.16.about. 1650, 1590, 1540 6.00(4H, brs), 6.57(1H, s), 7.10.about.7.56(4H, m) solvent: deuterated acetone30 Compound 30 3540, 3290, 3150 1.61(6H, d), 1.62(3H, d), 5.31.about.6.42(4H, brs), 7.08.about.7.83 1660, 1620, 1560 (5H, m) solvent: deuterated chloroform31 Compound 31 3520, 3430, 3360 1.57(3H, d), 1.87(6H, s), 5.26.about.6.33(4H, brs), 6.99.about.7.76 1650, 1570 (5H, m) solvent: deuterated chloroform32 Compound 32 3500, 3430, 3330 1.53(3H, d,d), 1.62(3H, d), 4.69.about.5.88(3H, brs), 6.20.about.7.19 1650, 1570 (3H, brs), 7.21.about.7.96(5H, m) solvent: deuterated acetone33 Compound 33 3510, 3430, 3350 1.58(6H, d), 1.62(3H, d), 2.41(3H, s), 5.22.about.5.67(1H, m), 1660, 1570 6.28.about.6.92(3H, brs), 6.61(1H, s), 6.92.about.7.49(3H, m) solvent: deuterated acetone34 Compound 34 3490, 3430, 3330 1.60(3H, d,d), 1.62(3H, d), 2.42(3H, s), 4.72.about.5.85(5H, brs), 1650, 1570 6.51(1H, s), 6.90.about.7.49(3H, m) solvent: deuterated chloroform35 Compound 35 3500, 3430, 3350 1.62(3H, d), 1.89(6H, s), 2.43(3H, s), 5.08.about.5.69(4H, brs), 1640, 1560 6.52(1H, s), 6.90.about.7.49(3H, m) solvent: deuterated chloroform36 Compound 36 3510, 3350, 3210 1.52(3H, d), 1.55(6H, d), 2.12(3H, s), 3.80(3H, s), 5.04.about. 1660, 1600, 1570 5.40(2H, m), 6.48(1H, brs), 6.78.about.7.20(3H, m) solvent: deuterated acetone37 Compound 37 3480, 3400, 3370 1.50(3H, d), 1.58(3H, d, d), 2.16(3H, s), 3.78(3H, s), 5.33.about. 1670, 1620, 1560 6.34(4H, m), 6.78.about.7.10(3H, m) solvent: deuterated chloroform38 Compound 38 3510, 3440, 3350 1.52(3H, d), 1.89(6H, s), 3.82(3H, s), 4.95.about.5.67(4H, brs), 1650, 1570 6.76.about.7.30(3H, m) solvent: deuterated chloroform39 Compound 39 3510, 3400, 3320 1.42(3H, d), 1.60(6H, d), 2.19(3H, s), 3.79(3H, s), 4.88.about. 1640, 1560 5.29(1H, m), 5.61.about.7.20(3H, m) solvent: deuterated chloroform40 Compound 40 3500, 3420, 3330 1.47(3H, d), 1.56(3H, d, d), 2.19(3H, s), 3.79(3H, s), 4.72.about. 1650, 1570 6.57(5H, brs), 6.64.about.7.28(3H, m) solvent: deuterated chloroform41 Compound 41 3510, 3420, 3350 1.51(3H, d), 1.88(6H, s), 2.20(3H, s), 3.81(3H, s), 4.85.about. 1650, 1630, 1570 5.58(4H, brs), 6.69.about.7.29(3H, m solvent: deuterated chloroform__________________________________________________________________________ *.sup.1 KBr tablet method *.sup.2 Internal standard: tetramethyl silane
In the following, the actual method for form preparation is described by way of formulation examples. In the formulation examples given below, "parts" refers to % by weight.
Formulation Example 1: Water-dispersible powder
______________________________________Compound of Preparation Example 1 20 partsDiatomaceous earth 62 partsWhite carbon 15 partsSodium alkylbenzene sulfonate 2 partsSodium lignin sulfonate 1 part______________________________________
The above were blended and uniformly mixed and pulverized to give 100 parts of a water-dispersible powder.
Formulation Example 2: Emulsion
______________________________________Compound of Preparation Example 2 40 partsXylene 20 partsDimethyl formamide 20 partsSolpol 2806B (surface active agent, 20 partsmanufactured by Toho ChemicalIndustry)______________________________________
The above were uniformly dissolved and mixed to give 100 parts of an emulsion.
Formulation Example 3: Dust
______________________________________Compound of Preparation Example 3 2 partsDiatomaceous earth 20 partsTalc 78 parts______________________________________
The above were blended and uniformly mixed and pulverized to give 100 parts of a dust.
Formulation Example 4: Granules
______________________________________Compound of Preparation Example 4 1 partBentonite 30 partsTalc 66 partsSodium lignin sulfonate 3 parts______________________________________
The above were blended, uniformly mixed and pulverized and thoroughly kneaded with addition of water followed by granulation and drying to give 100 parts of granules.
Formulation Example 5: Flowable agent
______________________________________Compound of Preparation Example 5 25 partsMethyl cellulose 0.3 partColloidal silica 1.5 partsSodium lignin sulfonate 1 partPolyoxyethylene nonylphenyl ether 2 partsWater 70.2 parts______________________________________
The above were thoroughly mixed and dispersed and the slurry-like mixture was subjected to wet-process pulverization to give 100 parts of a stable flowable agent.
Formulation Example 6: Water-dispersible Powder
A carrier for water-dispersible powder was obtained by uniformly pulverizing and mixing 97 parts of clay (commercial product name: Zieglite, manufactured by Zieglite Kogyo) as a carrier, 1.5 parts of an alkylaryl sulfonic acid salt (commercial product name: Neopelex, manufactured by Kao Atlas Co.) as a surface active agent and 1.5 parts of a non-ionic type and anionic type surface active agent (commercial product name: Solpol 800A, manufactured by Toho Chemical Industry Co.).
A water-dispersible powder was obtained by uniformly pulverizing and mixing 90 parts of this carrier for water-dispersible powder and 10 parts of the triazine derivative obtained in the above described Preparation Examples 1 to 5.
EXAMPLES 1 TO 41 UPLAND FIELD SOIL TREATMENT TEST
Wagner pots of 1/2000 were filled with a soil of non-paddy field and seeds of Digitaria sanguinalis, Alopecurus myosuroides, Abutilon theophrasti, Veronica persica, Viola arvensis, Polygonum persicaria, Amaranthus patulus, Galium sparium var. echinospermon, wheat, barley, corn and grain sorghum were uniformly sowed in the surface layer.
Prior to the germination of the wheat, barley, corn, grain sorghum and weeds thereafter, 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 sprinkling.
Table 4 shows the results of the investigations of the herbicidal effects and phytotoxicity to the wheat, barley, corn and grain sorghum after 30 days from the treatment with the herbicide solution. The dose was 25 to 100 g/10 ares calculated as the amount of the effective ingredient. The phytotoxicity to the wheat, barley, corn and grain sorghum and the herbicidal effects are expressed as shown below by measuring the respective air-dried weights.
______________________________________ Phytotoxicity to wheat, barley, corn & grain sorgham (relativeExtent of phytotoxicity to untreated zone)______________________________________0 100%1 61 to 99%2 21 to 60%3 11 to 20%4 1 to 10%5 0%______________________________________ Herbicidal effectsDegree of herbi- (relative to un-cidal effects treated zone)______________________________________0 100%1 61 to 99%2 21 to 60%3 11 to 20%4 1 to 10%5 0%______________________________________
COMPARATIVE EXAMPLES 1 TO 6
The same procedure as in Example 1 was undertaken excepting the use of the triazine derivatives A to C (described in the official publication of Japanese Patent Kokai No. 63-264465), D (described in the official publication of Japanese Patent Kokai No..63-51379), E (described in the official publication of Japanese Patent Kokai No. 63-146876) or F (described in the official publication of Japanese Patent Toku-Sai-Hyo No. 88/02368) expressed by the formulas given below in place of the triazine derivative prepared in Preparation Example 1, in Example 1. The results are shown in Table 4. ##STR63##
TABLE 4__________________________________________________________________________ Herbicidal effect Alope- Galium Amount curus Poly- sparium Phytotoxicity Com- of herb- myo- Digitaria Abutilon Ver- gonum Viola Amar- var. Grain pound icide sur- san- theo- onica persi- arven- anthus echino- Bar- sorNo. used (g/10a) oides guinalis phrasti persica caria sis patulus spermon Wheat ley Corn ghum__________________________________________________________________________Ex- Com- 100 5 5 5 5 5 5 5 5 0 0 0 0ample pound of 50 5 5 5 5 5 5 5 5 0 0 0 01 Prepara- 25 5 5 5 5 5 5 5 5 0 0 0 0 tion Ex- ample 1Ex- Com- 100 5 5 5 5 5 5 5 5 0 0 0 0ample pound of 50 5 5 5 5 5 5 5 5 0 0 0 02 Prepara- 25 5 5 5 5 5 5 5 5 0 0 0 0 tion Ex- ample 2Ex- Com- 100 5 5 5 5 5 5 5 5 0 0 0 0ample pound of 50 5 5 5 5 5 5 5 5 0 0 0 03 Prepara- 25 5 5 5 5 5 5 5 5 0 0 0 0 tion Ex- ample 3Ex- Com- 100 5 5 5 5 5 5 5 5 0 0 0 0ample pound of 50 5 5 5 5 5 5 5 5 0 0 0 04 Prepara- 25 5 5 5 5 5 5 5 5 0 0 0 0 tion Ex- ample 4Ex- Com- 100 5 5 5 5 5 5 5 5 0 0 0 0ample pound of 50 5 5 5 5 5 5 5 5 0 0 0 05 Prepara- 25 5 5 5 5 5 5 5 5 0 0 0 0 tion Ex- ample 5Ex- Com- 100 5 5 5 5 5 5 5 5 0 0 0 0ample pound of 50 5 5 5 5 5 5 5 5 0 0 0 06 Prepara- 25 5 5 5 5 5 5 5 5 0 0 0 0 tion Ex- ample 6Ex- Com- 100 5 5 5 5 5 5 5 5 0 0 0 0ample pound of 50 5 5 5 5 5 5 5 5 0 0 0 07 Prepara- 25 5 5 5 5 5 5 5 5 0 0 0 0 tion Ex- ample 7Ex- Com- 100 5 5 5 5 5 5 5 5 0 0 0 0ample pound of 50 5 5 5 5 5 5 5 5 0 0 0 08 Prepara- 25 5 5 5 5 5 5 5 5 0 0 0 0 tion Ex- ample 8Ex- Com- 100 5 5 5 5 5 5 5 5 0 0 0 0ample pound of 50 5 5 5 5 5 5 5 5 0 0 0 09 Prepara- 25 5 5 5 5 5 5 5 5 0 0 0 0 tion Ex- ample 9Ex- Com- 100 5 5 5 5 5 5 5 5 0 0 0 0ample pound of 50 5 5 5 5 5 5 5 5 0 0 0 010 Prepara- 25 5 5 5 5 5 5 5 5 0 0 0 0 tion Ex- ample 10Ex- Com- 100 5 5 5 5 5 5 5 5 0 0 0 0ample pound of 50 5 5 5 5 5 5 5 5 0 0 0 011 Prepara- 25 5 5 5 5 5 5 5 5 0 0 0 0 tion Ex- ample 11Ex- Com- 100 5 5 5 5 5 5 5 5 0 0 0 0ample pound of 50 5 5 5 5 5 5 5 5 0 0 0 012 Prepara- 25 5 5 5 5 5 5 5 5 0 0 0 0 tion Ex- ample 12Ex- Com- 100 5 5 5 5 5 5 5 5 0 0 0 0ample pound of 50 5 5 5 5 5 5 5 5 0 0 0 013 Prepara- 25 5 5 5 5 5 5 5 5 0 0 0 0 tion Ex- ample 13Ex- Com- 100 5 5 5 5 5 5 5 5 0 0 0 0ample pound of 50 5 5 5 5 5 5 5 5 0 0 0 014 Prepara- 25 5 5 5 5 5 5 5 5 0 0 0 0 tion Ex- ample 14Ex- Com- 100 5 5 5 5 5 5 5 5 0 0 0 0ample pound of 50 5 5 5 5 5 5 5 5 0 0 0 015 Prepara- 25 5 5 5 5 5 5 5 5 0 0 0 0 tion Ex- ample 15Ex- Com- 100 5 5 5 5 5 5 5 5 0 0 0 0ample pound of 50 5 5 5 5 5 5 5 5 0 0 0 016 Prepara- 25 5 5 5 5 5 5 5 5 0 0 0 0 tion Ex- ample 16Ex- Com- 100 5 5 5 5 5 5 5 5 0 0 0 0ample pound of 50 5 5 5 5 5 5 5 5 0 0 0 017 Prepara- 25 5 5 5 5 5 5 5 5 0 0 0 0 tion Ex- ample 17Ex- Com- 100 5 5 5 5 5 5 5 5 0 0 0 0ample pound of 50 5 5 5 5 5 5 5 5 0 0 0 018 Prepara- 25 5 5 5 5 5 5 5 5 0 0 0 0 tion Ex- ample 18Ex- Com- 100 5 5 5 5 5 5 5 5 0 0 0 0ample pound of 50 5 5 5 5 5 5 5 5 0 0 0 019 Prepara- 25 5 5 5 5 5 5 5 5 0 0 0 0 tion Ex- ample 19Ex- Com- 100 5 5 5 5 5 5 5 5 0 0 0 0ample pound of 50 5 5 5 5 5 5 5 5 0 0 0 020 Prepara- 25 5 5 5 5 5 5 5 5 0 0 0 0 tion Ex- ample 20Ex- Com- 100 5 5 5 5 5 5 5 5 0 0 0 0ample pound of 50 5 5 5 5 5 5 5 5 0 0 0 021 Prepara- 25 5 5 5 5 5 5 5 5 0 0 0 0 tion Ex- ample 21Ex- Com- 100 5 5 5 5 5 5 5 5 0 0 0 0ample pound of 50 5 5 5 5 5 5 5 5 0 0 0 022 Prepara- 25 5 5 5 5 5 5 5 5 0 0 0 0 tion Ex- ample 22Ex- Com- 100 5 5 5 5 5 5 5 5 0 0 0 0ample pound of 50 5 5 5 5 5 5 5 5 0 0 0 023 Prepara- 25 5 5 5 5 5 5 5 5 0 0 0 0 tion Ex- ample 23Ex- Com- 100 5 5 5 5 5 5 5 5 0 0 0 0ample pound of 50 5 5 5 5 5 5 5 5 0 0 0 024 Prepara- 25 5 5 5 5 5 5 5 5 0 0 0 0 tion Ex- ample 24Ex- Com- 100 5 5 5 5 5 5 5 5 0 0 0 0ample pound of 50 5 5 5 5 5 5 5 5 0 0 0 025 Prepara- 25 5 5 5 5 5 5 5 5 0 0 0 0 tion Ex- ample 25Ex- Com- 100 5 5 5 5 5 5 5 5 0 0 0 0ample pound of 50 5 5 5 5 5 5 5 5 0 0 0 026 Prepara- 25 5 5 5 5 5 5 5 5 0 0 0 0 tion Ex- ample 26Ex- Com- 100 5 5 5 5 5 5 5 5 0 0 0 0ample pound of 50 5 5 5 5 5 5 5 5 0 0 0 027 Prepara- 25 5 5 5 5 5 5 5 5 0 0 0 0 tion Ex- ample 27Ex- Com- 100 5 5 5 5 5 5 5 5 0 0 0 0ample pound of 50 5 5 5 5 5 5 5 5 0 0 0 028 Prepara- 25 5 5 5 5 5 5 5 5 0 0 0 0 tion Ex- ample 28Ex- Com- 100 5 5 5 5 5 5 5 5 0 0 0 0ample pound of 50 5 5 5 5 5 5 5 5 0 0 0 029 Prepara- 25 5 5 5 5 5 5 5 5 0 0 0 0 tion Ex- ample 29Ex- Com- 100 5 5 5 5 5 5 5 5 0 0 0 0ample pound of 50 5 5 5 5 5 5 5 5 0 0 0 030 Prepara- 25 5 5 5 5 5 5 5 5 0 0 0 0 tion Ex- ample 30Ex- Com- 100 5 5 5 5 5 5 5 5 0 0 0 0ample pound of 50 5 5 5 5 5 5 5 5 0 0 0 031 Prepara- 25 5 5 5 5 5 5 5 5 0 0 0 0 tion Ex- ample 31Ex- Com- 100 5 5 5 5 5 5 5 5 0 0 0 0ample pound of 50 5 5 5 5 5 5 5 5 0 0 0 032 Prepara- 25 5 5 5 5 5 5 5 5 0 0 0 0 tion Ex- ample 32Ex- Com- 100 5 5 5 5 5 5 5 5 0 0 0 0ample pound of 50 5 5 5 5 5 5 5 5 0 0 0 033 Prepara- 25 5 5 5 5 5 5 5 5 0 0 0 0 tion Ex- ample 33Ex- Com- 100 5 5 5 5 5 5 5 5 0 0 0 0ample pound of 50 5 5 5 5 5 5 5 5 0 0 0 034 Prepara- 25 5 5 5 5 5 5 5 5 0 0 0 0 tion Ex- ample 34Ex- Com- 100 5 5 5 5 5 5 5 5 0 0 0 0ample pound of 50 5 5 5 5 5 5 5 5 0 0 0 035 Prepara- 25 5 5 5 5 5 5 5 5 0 0 0 0 tion Ex- ample 35Ex- Com- 100 5 5 5 5 5 5 5 5 0 0 0 0ample pound of 50 5 5 5 5 5 5 5 5 0 0 0 036 Prepara- 25 5 5 5 5 5 5 5 5 0 0 0 0 tion Ex- ample 36Ex- Com- 100 5 5 5 5 5 5 5 5 0 0 0 0ample pound of 50 5 5 5 5 5 5 5 5 0 0 0 037 Prepara- 25 5 5 5 5 5 5 5 5 0 0 0 0 tion Ex- ample 37Ex- Com- 100 5 5 5 5 5 5 5 5 0 0 0 0ample pound of 50 5 5 5 5 5 5 5 5 0 0 0 038 Prepara- 25 5 5 5 5 5 5 5 5 0 0 0 0 tion Ex- ample 38Ex- Com- 100 5 5 5 5 5 5 5 5 0 0 0 0ample pound of 50 5 5 5 5 5 5 5 5 0 0 0 039 Prepara- 25 5 5 5 5 5 5 5 5 0 0 0 0 tion Ex- ample 39Ex- Com- 100 5 5 5 5 5 5 5 5 0 0 0 0ample pound of 50 5 5 5 5 5 5 5 5 0 0 0 040 Prepara- 25 5 5 5 5 5 5 5 5 0 0 0 0 tion Ex- ample 40Ex- Com- 100 5 5 5 5 5 5 5 5 0 0 0 0ample pound of 50 5 5 5 5 5 5 5 5 0 0 0 041 Prepara- 25 5 5 5 5 5 5 5 5 0 0 0 0 tion Ex- ample 41Com- Triazine 100 4 5 4 5 5 4 5 4 0 0 0 0para- deriva- 50 3 3 4 4 3 3 3 2 0 0 0 0tive tive A 25 1 1 2 3 2 2 1 1 0 0 0 0Ex-ampleCom- Triazine 100 3 3 4 4 3 3 4 2 0 0 0 0para- deriva- 50 1 1 3 3 2 2 3 0 0 0 0 0tive tive B 25 0 0 1 1 1 0 1 0 0 0 0 0Ex-ample2Com- Triazine 100 5 5 4 5 5 5 5 3 0 0 0 0para- deriva- 50 3 3 4 4 4 4 3 1 0 0 0 0tive tive C 25 2 2 3 3 2 2 2 1 0 0 0 0Ex-ample3Com- Triazine 100 5 5 4 5 5 4 5 4 0 0 0 0para- deriva- 50 3 3 4 4 4 4 4 3 0 0 0 0tive tive D 25 3 2 3 3 3 3 3 1 0 0 0 0Ex-ample4Com- Triazine 100 3 4 4 3 3 4 4 2 0 0 0 0para- deriva- 50 1 2 3 3 3 2 2 0 0 0 0 0tive tive E 25 0 0 1 0 0 0 0 0 0 0 0 0Ex-ample5Com- Triazine 100 3 5 4 5 4 4 5 4 0 0 0 0para- deriva- 50 2 3 3 4 3 4 3 3 0 0 0 0tive tive F 25 0 1 2 2 1 2 0 1 0 0 0 0Ex-ample6__________________________________________________________________________
EXAMPLES 42 TO 82 FOLIAGE TREATMENT TEST
Seeds of weeds including Abutilon theophrasti, Common blackjack, Amaranthus patulus, Cassia obtusifolia, Ipomoea purpurea, Galium sparium var. echinospermon, Veronica persica and seeds of crops including corn, grain sorghum, wheat, barley and oat were sowed on to the Wagner pots of 1/2000 filled with soil of upland field and, after covering up with soil, were grown in a greenhouse and, when the weeds were in their mono- to bi-foliate period and the crops were in their tri-foliate period, 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 corresponding to 100 liters/10 ares. Thereafter, 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 treatment. The results are shown in Table 5.
TABLE 5______________________________________[Criteria of estimation]Degree of herbicidal Herbicidal effectseffects (% killed weeds)______________________________________0 less than 5% (almost no effects)1 5 to 20%2 20 to 40%3 40 to 70%4 70 to 80%5 90% or more (almost complete withering)______________________________________
The % killed weeds given above was obtained from the following equation by determining the overground raw grass weight in the phytotoxicity treated zone and the overground raw grass weight in the untreated zone. ##EQU1##
COMPARATIVE EXAMPLES 7 TO 12
The same procedure as in Example 6 was undertaken excepting the use of the triazine derivative A, B, C, D, E or F shown in Comparative Examples 1 to 6 in place of the triazine derivative prepared in Preparation Example 1, in Example 42. The results are shown in Table 5.
TABLE 5 Herbicidal effect Galium Amount of Phytotoxicity Cassia sparium Compound herbicide Grain Abutilon Common Amaranthus obtusifolia Ipomoea var. Veronica No. used (g/10a) Corn sorghum Wheat Barley Oats theophrasti blackjack patulus L. purpurea echinospermon persica Example Compound 400 0 0 0 0 0 5 5 5 5 5 5 5 42 of 200 0 0 0 0 0 5 5 5 5 5 5 5 Prepara- 100 0 0 0 0 0 5 5 5 5 5 5 5 tion 50 0 0 0 0 0 5 5 5 5 5 5 5 Example 25 0 0 0 0 0 5 5 5 5 5 5 5 1 12.5 0 0 0 0 0 5 5 5 5 5 5 5 Example Compound 400 0 0 0 0 0 5 5 5 5 5 5 5 43 of 200 0 0 0 0 0 5 5 5 5 5 5 5 Prepara- 100 0 0 0 0 0 5 5 5 5 5 5 5 tion 50 0 0 0 0 0 5 5 5 5 5 5 5 Example 25 0 0 0 0 0 5 5 5 5 5 5 5 2 12.5 0 0 0 0 0 5 5 5 5 5 5 5 Example Compound 400 0 0 0 0 0 5 5 5 5 5 5 5 44 of 200 0 0 0 0 0 5 5 5 5 5 5 5 Prepara- 100 0 0 0 0 0 5 5 5 5 5 5 5 tion 50 0 0 0 0 0 5 5 5 5 5 5 5 Example 25 0 0 0 0 0 5 5 5 5 5 5 5 3 12.5 0 0 0 0 0 5 5 5 5 5 5 5 Example Compound 400 0 0 0 0 0 5 5 5 5 5 5 5 45 of 200 0 0 0 0 0 5 5 5 5 5 5 5 Prepara- 100 0 0 0 0 0 5 5 5 5 5 5 5 tion 50 0 0 0 0 0 5 5 5 5 5 5 5 Example 25 0 0 0 0 0 5 5 5 5 5 5 5 4 12.5 0 0 0 0 0 5 5 5 5 5 5 5 Example Compound 400 0 0 0 0 0 5 5 5 5 5 5 5 46 of 200 0 0 0 0 0 5 5 5 5 5 5 5 Prepara- 100 0 0 0 0 0 5 5 5 5 5 5 5 tion 50 0 0 0 0 0 5 5 5 5 5 5 5 Example 25 0 0 0 0 0 5 5 5 5 5 5 5 5 12.5 0 0 0 0 0 5 5 5 5 5 5 5 Example Compound 400 0 0 0 0 0 5 5 5 5 5 5 5 47 of 200 0 0 0 0 0 5 5 5 5 5 5 5 Prepara- 100 0 0 0 0 0 5 5 5 5 5 5 5 tion 50 0 0 0 0 0 5 5 5 5 5 5 5 Example 25 0 0 0 0 0 5 5 5 5 5 5 5 6 12.5 0 0 0 0 0 5 5 5 5 5 5 5 Example Compound 400 0 0 0 0 0 5 5 5 5 5 5 5 48 of 200 0 0 0 0 0 5 5 5 5 5 5 5 Prepara- 100 0 0 0 0 0 5 5 5 5 5 5 5 tion 50 0 0 0 0 0 5 5 5 5 5 5 5 Example 25 0 0 0 0 0 5 5 5 5 5 5 5 7 12.5 0 0 0 0 0 5 5 5 5 5 5 5 Example Compound 400 0 0 0 0 0 5 5 5 5 5 5 5 49 of 200 0 0 0 0 0 5 5 5 5 5 5 5 Prepara- 100 0 0 0 0 0 5 5 5 5 5 5 5 tion 50 0 0 0 0 0 5 5 5 5 5 5 5 Example 25 0 0 0 0 0 5 5 5 5 5 5 5 8 12.5 0 0 0 0 0 5 5 5 5 5 5 5 Example Compound 400 0 0 0 0 0 5 5 5 5 5 5 5 50 of 200 0 0 0 0 0 5 5 5 5 5 5 5 Prepara- 100 0 0 0 0 0 5 5 5 5 5 5 5 tion 50 0 0 0 0 0 5 5 5 5 5 5 5 Example 25 0 0 0 0 0 5 5 5 5 5 5 5 9 12.5 0 0 0 0 0 5 5 5 5 5 5 5 Example Compound 400 0 0 0 0 0 5 5 5 5 5 5 5 51 of 200 0 0 0 0 0 5 5 5 5 5 5 5 Prepara- 100 0 0 0 0 0 5 5 5 5 5 5 5 tion 50 0 0 0 0 0 5 5 5 5 5 5 5 Example 25 0 0 0 0 0 5 5 5 5 5 5 5 10 12.5 0 0 0 0 0 5 5 5 5 5 5 5 Example Compound 400 0 0 0 0 0 5 5 5 5 5 5 5 52 of 200 0 0 0 0 0 5 5 5 5 5 5 5 Prepara- 100 0 0 0 0 0 5 5 5 5 5 5 5 tion 50 0 0 0 0 0 5 5 5 5 5 5 5 Example 25 0 0 0 0 0 5 5 5 5 5 5 5 11 12.5 0 0 0 0 0 5 5 5 5 5 5 5 Example Compound 400 0 0 0 0 0 5 5 5 5 5 5 5 53 of 200 0 0 0 0 0 5 5 5 5 5 5 5 Prepara- 100 0 0 0 0 0 5 5 5 5 5 5 5 tion 50 0 0 0 0 0 5 5 5 5 5 5 5 Example 25 0 0 0 0 0 5 5 5 5 5 5 5 12 12.5 0 0 0 0 0 5 5 5 5 5 5 5 Example Compound 400 0 0 0 0 0 5 5 5 5 5 5 5 54 of 200 0 0 0 0 0 5 5 5 5 5 5 5 Prepara- 100 0 0 0 0 0 5 5 5 5 5 5 5 tion 50 0 0 0 0 0 5 5 5 5 5 5 5 Example 25 0 0 0 0 0 5 5 5 5 5 5 5 13 12.5 0 0 0 0 0 5 5 5 5 5 5 5 Example Compound 400 0 0 0 0 0 5 5 5 5 5 5 5 55 of 200 0 0 0 0 0 5 5 5 5 5 5 5 Prepara- 100 0 0 0 0 0 5 5 5 5 5 5 5 tion 50 0 0 0 0 0 5 5 5 5 5 5 5 Example 25 0 0 0 0 0 5 5 5 5 5 5 5 14 12.5 0 0 0 0 0 5 5 5 5 5 5 5 Example Compound 400 0 0 0 0 0 5 5 5 5 5 5 5 56 of 200 0 0 0 0 0 5 5 5 5 5 5 5 Prepara- 100 0 0 0 0 0 5 5 5 5 5 5 5 tion 50 0 0 0 0 0 5 5 5 5 5 5 5 Example 25 0 0 0 0 0 5 5 5 5 5 5 5 15 12.5 0 0 0 0 0 5 5 5 5 5 5 5 Example Compound 400 0 0 0 0 0 5 5 5 5 5 5 5 57 of 200 0 0 0 0 0 5 5 5 5 5 5 5 Prepara- 100 0 0 0 0 0 5 5 5 5 5 5 5 tion 50 0 0 0 0 0 5 5 5 5 5 5 5 Example 25 0 0 0 0 0 5 5 5 5 5 5 5 16 12.5 0 0 0 0 0 5 5 5 5 5 5 5 Example Compound 400 0 0 0 0 0 5 5 5 5 5 5 5 58 of 200 0 0 0 0 0 5 5 5 5 5 5 5 Prepara- 100 0 0 0 0 0 5 5 5 5 5 5 5 tion 50 0 0 0 0 0 5 5 5 5 5 5 5 Example 25 0 0 0 0 0 5 5 5 5 5 5 5 17 12.5 0 0 0 0 0 5 5 5 5 5 5 5 Example Compound 400 0 0 0 0 0 5 5 5 5 5 5 5 59 of 200 0 0 0 0 0 5 5 5 5 5 5 5 Prepara- 100 0 0 0 0 0 5 5 5 5 5 5 5 tion 50 0 0 0 0 0 5 5 5 5 5 5 5 Example 25 0 0 0 0 0 5 5 5 5 5 5 5 18 12.5 0 0 0 0 0 5 5 5 5 5 5 5 Example Compound 400 0 0 0 0 0 5 5 5 5 5 5 5 60 of 200 0 0 0 0 0 5 5 5 5 5 5 5 Prepara- 100 0 0 0 0 0 5 5 5 5 5 5 5 tion 50 0 0 0 0 0 5 5 5 5 5 5 5 Example 25 0 0 0 0 0 5 5 5 5 5 5 5 19 12.5 0 0 0 0 0 5 5 5 5 5 5 5 Example Compound 400 0 0 0 0 0 5 5 5 5 5 5 5 61 of 200 0 0 0 0 0 5 5 5 5 5 5 5 Prepara- 100 0 0 0 0 0 5 5 5 5 5 5 5 tion 50 0 0 0 0 0 5 5 5 5 5 5 5 Example 25 0 0 0 0 0 5 5 5 5 5 5 5 20 12.5 0 0 0 0 0 5 5 5 5 5 5 5 Example Compound 400 0 0 0 0 0 5 5 5 5 5 5 5 62 of 200 0 0 0 0 0 5 5 5 5 5 5 5 Prepara- 100 0 0 0 0 0 5 5 5 5 5 5 5 tion 50 0 0 0 0 0 5 5 5 5 5 5 5 Example 25 0 0 0 0 0 5 5 5 5 5 5 5 21 12.5 0 0 0 0 0 5 5 5 5 5 5 5 Example Compound 400 0 0 0 0 0 5 5 5 5 5 5 5 63 of 200 0 0 0 0 0 5 5 5 5 5 5 5 Prepara- 100 0 0 0 0 0 5 5 5 5 5 5 5 tion 50 0 0 0 0 0 5 5 5 5 5 5 5 Example 25 0 0 0 0 0 5 5 5 5 5 5 5 22 12.5 0 0 0 0 0 5 5 5 5 5 5 5 Example Compound 400 0 0 0 0 0 5 5 5 5 5 5 5 64 of 200 0 0 0 0 0 5 5 5 5 5 5 5 Prepara- 100 0 0 0 0 0 5 5 5 5 5 5 5 tion 50 0 0 0 0 0 5 5 5 5 5 5 5 Example 25 0 0 0 0 0 5 5 5 5 5 5 5 23 12.5 0 0 0 0 0 5 5 5 5 5 5 5 Example Compound 400 0 0 0 0 0 5 5 5 5 5 5 5 65 of 200 0 0 0 0 0 5 5 5 5 5 5 5 Prepara- 100 0 0 0 0 0 5 5 5 5 5 5 5 tion 50 0 0 0 0 0 5 5 5 5 5 5 5 Example 25 0 0 0 0 0 5 5 5 5 5 5 5 24 12.5 0 0 0 0 0 5 5 5 5 5 5 5 Example Compound 400 0 0 0 0 0 5 5 5 5 5 5 5 66 of 200 0 0 0 0 0 5 5 5 5 5 5 5 Prepara- 100 0 0 0 0 0 5 5 5 5 5 5 5 tion 50 0 0 0 0 0 5 5 5 5 5 5 5 Example 25 0 0 0 0 0 5 5 5 5 5 5 5 25 12.5 0 0 0 0 0 5 5 5 5 5 5 5 Example Compound 400 0 0 0 0 0 5 5 5 5 5 5 5 67 of 200 0 0 0 0 0 5 5 5 5 5 5 5 Prepara- 100 0 0 0 0 0 5 5 5 5 5 5 5 tion 50 0 0 0 0 0 5 5 5 5 5 5 5 Example 25 0 0 0 0 0 5 5 5 5 5 5 5 26 12.5 0 0 0 0 0 5 5 5 5 5 5 5 Example Compound 400 0 0 0 0 0 5 5 5 5 5 5 5 68 of 200 0 0 0 0 0 5 5 5 5 5 5 5 Prepara- 100 0 0 0 0 0 5 5 5 5 5 5 5 tion 50 0 0 0 0 0 5 5 5 5 5 5 5 Example 25 0 0 0 0 0 5 5 5 5 5 5 5 27 12.5 0 0 0 0 0 5 5 5 5 5 5 5 Example Compound 400 0 0 0 0 0 5 5 5 5 5 5 5 69 of 200 0 0 0 0 0 5 5 5 5 5 5 5 Prepara- 100 0 0 0 0 0 5 5 5 5 5 5 5 tion 50 0 0 0 0 0 5 5 5 5 5 5 5 Example 25 0 0 0 0 0 5 5 5 5 5 5 5 28 12.5 0 0 0 0 0 5 5 5 5 5 5 5 Example Compound 400 0 0 0 0 0 5 5 5 5 5 5 5 70 of 200 0 0 0 0 0 5 5 5 5 5 5 5 Prepara- 100 0 0 0 0 0 5 5 5 5 5 5 5 tion 50 0 0 0 0 0 5 5 5 5 5 5 5 Example 25 0 0 0 0 0 5 5 5 5 5 5 5 29 12.5 0 0 0 0 0 5 5 5 5 5 5 5 Example Compound 400 0 0 0 0 0 5 5 5 5 5 5 5 71 of 200 0 0 0 0 0 5 5 5 5 5 5 5 Prepara- 100 0 0 0 0 0 5 5 5 5 5 5 5 tion 50 0 0 0 0 0 5 5 5 5 5 5 5 Example 25 0 0 0 0 0 5 5 5 5 5 5 5 30 12.5 0 0 0 0 0 5 5 5 5 5 5 5 Example Compound 400 0 0 0 0 0 5 5 5 5 5 5 5 72 of 200 0 0 0 0 0 5 5 5 5 5 5 5 Prepara- 100 0 0 0 0 0 5 5 5 5 5 5 5 tion 50 0 0 0 0 0 5 5 5 5 5 5 5 Example 25 0 0 0 0 0 5 5 5 5 5 5 5 31 12.5 0 0 0 0 0 5 5 5 5 5 5 5 Example Compound 400 0 0 0 0 0 5 5 5 5 5 5 5 73 of 200 0 0 0 0 0 5 5 5 5 5 5 5 Prepara- 100 0 0 0 0 0 5 5 5 5 5 5 5 tion 50 0 0 0 0 0 5 5 5 5 5 5 5 Example 25 0 0 0 0 0 5 5 5 5 5 5 5 32 12.5 0 0 0 0 0 5 5 5 5 5 5 5 Example Compound 400 0 0 0 0 0 5 5 5 5 5 5 5 74 of 200 0 0 0 0 0 5 5 5 5 5 5 5 Prepara- 100 0 0 0 0 0 5 5 5 5 5 5 5 tion 50 0 0 0 0 0 5 5 5 5 5 5 5 Example 25 0 0 0 0 0 5 5 5 5 5 5 5 33 12.5 0 0 0 0 0 5 5 5 5 5 5 5 Example Compound 400 0 0 0 0 0 5 5 5 5 5 5 5 75 of 200 0 0 0 0 0 5 5 5 5 5 5 5 Prepara- 100 0 0 0 0 0 5 5 5 5 5 5 5 tion 50 0 0 0 0 0 5 5 5 5 5 5 5 Example 25 0 0 0 0 0 5 5 5 5 5 5 5 34 12.5 0 0 0 0 0 5 5 5 5 5 5 5 Example Compound 400 0 0 0 0 0 5 5 5 5 5 5 5 76 of 200 0 0 0 0 0 5 5 5 5 5 5 5 Prepara- 100 0 0 0 0 0 5 5 5 5 5 5 5 tion 50 0 0 0 0 0 5 5 5 5 5 5 5 Example 25 0 0 0 0 0 5 5 5 5 5 5 5 35 12.5 0 0 0 0 0 5 5 5 5 5 5 5 Example Compound 400 0 0 0 0 0 5 5 5 5 5 5 5 77 of 200 0 0 0 0 0 5 5 5 5 5 5 5 Prepara- 100 0 0 0 0 0 5 5 5 5 5 5 5 tion 50 0 0 0 0 0 5 5 5 5 5 5 5 Example 25 0 0 0 0 0 5 5 5 5 5 5 5 36 12.5 0 0 0 0 0 5 5 5 5 5 5 5 Example Compound 400 0 0 0 0 0 5 5 5 5 5 5 5 78 of 200 0 0 0 0 0 5 5 5 5 5 5 5 Prepara- 100 0 0 0 0 0 5 5 5 5 5 5 5 tion 50 0 0 0 0 0 5 5 5 5 5 5 5 Example 25 0 0 0 0 0 5 5 5 5 5 5 5 37 12.5 0 0 0 0 0 5 5 5 5 5 5 5 Example Compound 400 0 0 0 0 0 5 5 5 5 5 5 5 79 of 200 0 0 0 0 0 5 5 5 5 5 5 5 Prepara- 100 0 0 0 0 0 5 5 5 5 5 5 5 tion 50 0 0 0 0 0 5 5 5 5 5 5 5 Example 25 0 0 0 0 0 5 5 5 5 5 5 5 38 12.5 0 0 0 0 0 5 5 5 5 5 5 5 Example Compound 400 0 0 0 0 0 5 5 5 5 5 5 5 80 of 200 0 0 0 0 0 5 5 5 5 5 5 5 Prepara- 100 0 0 0 0 0 5 5 5 5 5 5 5 tion 50 0 0 0 0 0 5 5 5 5 5 5 5 Example 25 0 0 0 0 0 5 5 5 5 5 5 5 39 12.5 0 0 0 0 0 5 5 5 5 5 5 5 Example Compound 400 0 0 0 0 0 5 5 5 5 5 5 5 81 of 200 0 0 0 0 0 5 5 5 5 5 5 5 Prepara- 100 0 0 0 0 0 5 5 5 5 5 5 5 tion 50 0 0 0 0 0 5 5 5 5 5 5 5 Example 25 0 0 0 0 0 5 5 5 5 5 5 5 40 12.5 0 0 0 0 0 5 5 5 5 5 5 5 Example Compound 400 0 0 0 0 0 5 5 5 5 5 5 5 82 of 200 0 0 0 0 0 5 5 5 5 5 5 5 Prepara- 100 0 0 0 0 0 5 5 5 5 5 5 5 tion 50 0 0 0 0 0 5 5 5 5 5 5 5 Example 25 0 0 0 0 0 5 5 5 5 5 5 5 41 12.5 0 0 0 0 0 5 5 5 5 5 5 5 Compara- Triazine 400 0 0 0 0 0 5 5 5 5 5 5 5 tive deriva- 200 0 0 0 0 0 5 5 5 5 5 5 5 Example tive B 100 0 0 0 0 0 5 5 5 5 5 5 5 7 50 0 0 0 0 0 5 3 4 3 3 3 4 25 0 0 0 0 0 3 3 4 3 3 2 3 12.5 0 0 0 0 0 1 2 2 2 2 1 2 Compara- Triazine 400 0 0 0 0 0 5 5 5 5 5 5 5 tive deriva- 200 0 0 0 0 0 5 5 5 5 5 5 5 Example tive C 100 0 0 0 0 0 5 5 5 5 5 5 5 8 50 0 0 0 0 0 3 3 4 4 3 3 4 25 0 0 0 0 0 3 3 4 2 3 2 3 12.5 0 0 0 0 0 2 2 2 1 2 1 2 Compara- Triazine 400 0 0 0 0 0 5 5 5 5 5 5 5 tive deriva- 200 0 0 0 0 0 5 5 5 5 5 5 5 Example tive D 100 0 0 0 0 0 5 5 5 5 5 5 5 9 50 0 0 0 0 0 5 5 5 5 4 5 5 25 0 0 0 0 0 4 4 4 4 3 4 4 12.5 0 0 0 0 0 2 2 2 2 3 3 3 Compara- Triazine 400 0 0 0 0 0 5 5 5 5 5 5 5 tive deriva- 200 0 0 0 0 0 5 5 5 5 5 5 5 Example tive E 100 0 0 0 0 0 5 5 5 5 5 4 5 10 50 0 0 0 0 0 4 4 5 5 5 4 3 25 0 0 0 0 0 4 4 4 3 4 3 2 12.5 0 0 0 0 0 3 3 4 2 3 2 1 Compara- Triazine 400 0 0 0 0 0 5 5 5 5 5 5 5 tive deriva- 200 0 0 0 0 0 5 5 5 5 5 5 5 Example tive F 100 0 0 0 0 0 5 5 5 4 5 5 5 11 50 0 0 0 0 0 3 5 5 3 5 3 4 25 0 0 0 0 0 3 5 5 2 5 2 3 12.5 0 0 0 0 0 1 4 5 2 3 1 2 Compara- Triazine 400 0 0 0 0 0 5 5 5 5 5 5 5 tive deriva- 200 0 0 0 0 0 5 5 5 5 5 5 5 Example tive G 100 0 0 0 0 0 5 5 5 5 5 5 5 12 50 0 0 0 0 0 4 5 5 4 5 5 5 25 0 0 0 0 0 3 5 5 3 5 4 4 12.5 0 0 0 0 0 1 4 5 2 3 3 3
EXAMPLES 83 TO 123: PADDY SOIL TREATMENT TEST
Porcelain pots of 1/15500 are were filled with a paddy field soil and seeds of Echinochola crus-galli P. Beauv.var formosenis Ohwi, Cyperus difformis L., broad-leaved weeds (Rotala indica (Willd) Koehne var. uligirosa (Miq.) Koehne and Monochoria vaginalis Presl var. plantaginea) and Scirpus juncoides Roxb. ssp. Hotarui Ohwi T. Koyama were uniformly sowed to the surface layer and further tubers of Cyperus serotinus Rottb. and Sagittaria pygmaea Miq. were transplanted followed by transplantation of paddy rice in the bifoliate period.
Before germination of the weeds, thereafter, 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 water.
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 solution. Incidentally, dose is given by the amount of the effective ingredient per 10 ares. And, the phytotoxicity to paddy rice and the herbicidal effects are expressed as shown below by determining the respective air-dried weights.
______________________________________ Phytotoxicity to paddy riceExtent of phytotoxicity (relative to untreated zone)______________________________________0 100%1 95 to 99%2 90 to 94%3 80 to 89%4 60 to 79%5 50 to 59%______________________________________Degree of herbi- Herbicidal effects (relativecidal effects to untreated zone)______________________________________0 100%1 61 to 99%2 21 to 60%3 11 to 20%4 1 to 10%5 0%______________________________________
COMPARATIVE EXAMPLES 13 TO 18
The same procedure as in Example 11 was undertaken excepting the use of the triazine derivative A, B, C, D, E or F shown in Comparative Examples 1 to 6 in place of the triazine derivative prepared in Preparation Example 1, in Example 83. The results are shown in Table 6.
TABLE 6__________________________________________________________________________ Amount Herbicidal effect of Echinochola crus-galli Cyperus Scirpus juncoides Cyperus Sagittaria Paddy Compound herbicide P. Beauv. var. serotinus Roxb. ssp. Hotarui difformis Broadleaf pygmaea riceNo. used (g/10a) formosensis Ohwi Rottb. Ohwi T. Koyama L. weeds Miq. plants__________________________________________________________________________Example Compound 100 5 5 5 5 5 5 083 of 50 5 5 5 5 5 5 0 Preparation 25 5 5 5 5 5 5 0 Example 1 12.5 5 5 5 5 5 5 0Example Compound 100 5 5 5 5 5 5 084 of 50 5 5 5 5 5 5 0 Preparation 25 5 5 5 5 5 5 0 Example 2 12.5 5 5 5 5 5 5 0Example Compound 100 5 5 5 5 5 5 085 of 50 5 5 5 5 5 5 0 Preparation 25 5 5 5 5 5 5 0 Example 3 12.5 5 5 5 5 5 5 0Example Compound 100 5 5 5 5 5 5 086 of 50 5 5 5 5 5 5 0 Preparation 25 5 5 5 5 5 5 0 Example 4 12.5 5 5 5 5 5 5 0Example Compound 100 5 5 5 5 5 5 087 of 50 5 5 5 5 5 5 0 Preparation 25 5 5 5 5 5 5 0 Example 5 12.5 5 5 5 5 5 5 0Example Compound 100 5 5 5 5 5 5 088 of 50 5 5 5 5 5 5 0 Preparation 25 5 5 5 5 5 5 0 Example 6 12.5 5 5 5 5 5 5 0Example Compound 100 5 5 5 5 5 5 089 of 50 5 5 5 5 5 5 0 Preparation 25 5 5 5 5 5 5 0 Example 7 12.5 5 5 5 5 5 5 0Example Compound 100 5 5 5 5 5 5 090 of 50 5 5 5 5 5 5 0 Preparation 25 5 5 5 5 5 5 0 Example 8 12.5 5 5 5 5 5 5 0Example Compound 100 5 5 5 5 5 5 091 of 50 5 5 5 5 5 5 0 Preparation 25 5 5 5 5 5 5 0 Example 9 12.5 5 5 5 5 5 5 0Example Compound 100 5 5 5 5 5 5 092 of 50 5 5 5 5 5 5 0 Preparation 25 5 5 5 5 5 5 0 Example 10 12.5 5 5 5 5 5 5 0Example Compound 100 5 5 5 5 5 5 093 of 50 5 5 5 5 5 5 0 Preparation 25 5 5 5 5 5 5 0 Example 11 12.5 5 5 5 5 5 5 0Example Compound 100 5 5 5 5 5 5 094 of 50 5 5 5 5 5 5 0 Preparation 25 5 5 5 5 5 5 0 Example 12 12.5 5 5 5 5 5 5 0Example Compound 100 5 5 5 5 5 5 095 of 50 5 5 5 5 5 5 0 Preparation 25 5 5 5 5 5 5 0 Example 13 12.5 5 5 5 5 5 5 0Example Compound 100 5 5 5 5 5 5 096 of 50 5 5 5 5 5 5 0 Preparation 25 5 5 5 5 5 5 0 Example 14 12.5 5 5 5 5 5 5 0Example Compound 100 5 5 5 5 5 5 097 of 50 5 5 5 5 5 5 0 Preparation 25 5 5 5 5 5 5 0 Example 15 12.5 5 5 5 5 5 5 0Example Compound 100 5 5 5 5 5 5 098 of 50 5 5 5 5 5 5 0 Preparation 25 5 5 5 5 5 5 0 Example 16 12.5 5 5 5 5 5 5 0Example Compound 100 5 5 5 5 5 5 099 of 50 5 5 5 5 5 5 0 Preparation 25 5 5 5 5 5 5 0 Example 17 12.5 5 5 5 5 5 5 0Example Compound 100 5 5 5 5 5 5 0100 of 50 5 5 5 5 5 5 0 Preparation 25 5 5 5 5 5 5 0 Example 18 12.5 5 5 5 5 5 5 0Example Compound 100 5 5 5 5 5 5 0101 of 50 5 5 5 5 5 5 0 Preparation 25 5 5 5 5 5 5 0 Example 19 12.5 5 5 5 5 5 5 0Example Compound 100 5 5 5 5 5 5 0102 of 50 5 5 5 5 5 5 0 Preparation 25 5 5 5 5 5 5 0 Example 20 12.5 5 5 5 5 5 5 0Example Compound 100 5 5 5 5 5 5 0103 of 50 5 5 5 5 5 5 0 Preparation 25 5 5 5 5 5 5 0 Example 21 12.5 5 5 5 5 5 5 0Example Compound 100 5 5 5 5 5 5 0104 of 50 5 5 5 5 5 5 0 Preparation 25 5 5 5 5 5 5 0 Example 22 12.5 5 5 5 5 5 5 0Example Compound 100 5 5 5 5 5 5 0105 of 50 5 5 5 5 5 5 0 Preparation 25 5 5 5 5 5 5 0 Example 23 12.5 5 5 5 5 5 5 0Example Compound 100 5 5 5 5 5 5 0106 of 50 5 5 5 5 5 5 0 Preparation 25 5 5 5 5 5 5 0 Example 24 12.5 5 5 5 5 5 5 0Example Compound 100 5 5 5 5 5 5 0107 of 50 5 5 5 5 5 5 0 Preparation 25 5 5 5 5 5 5 0 Example 25 12.5 5 5 5 5 5 5 0Example Compound 100 5 5 5 5 5 5 0108 of 50 5 5 5 5 5 5 0 Preparation 25 5 5 5 5 5 5 0 Example 26 12.5 5 5 5 5 5 5 0Example Compound 100 5 5 5 5 5 5 0109 of 50 5 5 5 5 5 5 0 Preparation 25 5 5 5 5 5 5 0 Example 27 12.5 5 5 5 5 5 5 0Example Compound 100 5 5 5 5 5 5 0110 of 50 5 5 5 5 5 5 0 Preparation 25 5 5 5 5 5 5 0 Example 28 12.5 5 5 5 5 5 5 0Example Compound 100 5 5 5 5 5 5 0111 of 50 5 5 5 5 5 5 0 Preparation 25 5 5 5 5 5 5 0 Example 29 12.5 5 5 5 5 5 5 0Example Compound 100 5 5 5 5 5 5 0112 of 50 5 5 5 5 5 5 0 Preparation 25 5 5 5 5 5 5 0 Example 30 12.5 5 5 5 5 5 5 0Example Compound 100 5 5 5 5 5 5 0113 of 50 5 5 5 5 5 5 0 Preparation 25 5 5 5 5 5 5 0 Example 31 12.5 5 5 5 5 5 5 0Example Compound 100 5 5 5 5 5 5 0114 of 50 5 5 5 5 5 5 0 Preparation 25 5 5 5 5 5 5 0 Example 32 12.5 5 5 5 5 5 5 0Example Compound 100 5 5 5 5 5 5 0115 of 50 5 5 5 5 5 5 0 Preparation 25 5 5 5 5 5 5 0 Example 33 12.5 5 5 5 5 5 5 0Example Compound 100 5 5 5 5 5 5 0116 of 50 5 5 5 5 5 5 0 Preparation 25 5 5 5 5 5 5 0 Example 34 12.5 5 5 5 5 5 5 0Example Compound 100 5 5 5 5 5 5 0117 of 50 5 5 5 5 5 5 0 Preparation 25 5 5 5 5 5 5 0 Example 35 12.5 5 5 5 5 5 5 0Example Compound 100 5 5 5 5 5 5 0118 of 50 5 5 5 5 5 5 0 Preparation 25 5 5 5 5 5 5 0 Example 36 12.5 5 5 5 5 5 5 0Example Compound 100 5 5 5 5 5 5 0119 of 50 5 5 5 5 5 5 0 Preparation 25 5 5 5 5 5 5 0 Example 37 12.5 5 5 5 5 5 5 0Example Compound 100 5 5 5 5 5 5 0120 of 50 5 5 5 5 5 5 0 Preparation 25 5 5 5 5 5 5 0 Example 38 12.5 5 5 5 5 5 5 0Example Compound 100 5 5 5 5 5 5 0121 of 50 5 5 5 5 5 5 0 Preparation 25 5 5 5 5 5 5 0 Example 39 12.5 5 5 5 5 5 5 0Example Compound 100 5 5 5 5 5 5 0122 of 50 5 5 5 5 5 5 0 Preparation 25 5 5 5 5 5 5 0 Example 40 12.5 5 5 5 5 5 5 0Example Compound 100 5 5 5 5 5 5 0123 of 50 5 5 5 5 5 5 0 Preparation 25 5 5 5 5 5 5 0 Example 41 12.5 5 5 5 5 5 5 0Compara- Triazine 100 5 5 5 5 5 5 0tive derivative 50 5 5 4 5 4 5 0Example A 25 5 4 3 5 4 3 013 12.5 5 4 2 5 4 2 0Compara- Triazine 100 5 4 5 5 5 5 0tive derivative 50 5 4 5 5 4 5 0Example B 25 5 3 4 5 4 3 014 12.5 5 3 2 5 4 2 0Compara- Triazine 100 5 5 5 5 5 5 0tive derivative 50 5 5 5 5 5 5 0Example C 25 5 5 3 5 5 3 015 12.5 5 3 2 5 5 3 0Compara- Triazine 100 5 5 5 5 5 5 0tive derivative 50 5 5 5 5 5 5 0Example D 25 5 5 5 5 5 5 016 12.5 5 5 3 5 5 3 0Compara- Triazine 100 5 5 5 5 5 5 0tive derivative 50 5 5 5 5 5 5 0Example E 25 5 5 5 5 5 5 017 12.5 5 4 3 5 5 3 0Compara- Triazine 100 5 5 5 5 5 5 0tive derivative 50 5 5 5 5 5 5 0Example F 25 5 5 5 5 5 5 018 12.5 5 3 4 5 5 3 0__________________________________________________________________________
Utilizability in industry
The triazine derivative of the present invention is a novel compound and can be efficiently utilized as a herbicide. The herbicide of the present invention with the said triazine derivative as the effective ingredient exhibits, as compared with conventional herticides for upland field, excellent herbicidal effects against weeds including troublesome weeds without causing phytotoxicity to upland crops and, in particular, 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 crops. Further, the herbicides of the present invention exhibit higher effectiveness against troublesome weeds still with less phytotoxicity than hitherto known herbicides for paddy rice.

Claims

1. A triazine compound of the formula ##STR64## wherein A is ##STR65## in which Y.sup.2 and Y.sup.3 are the same or different and each is a methyl group or a methoxy group or ##STR66## in which Y.sup.4 is a methyl group, a trifluoromethyl group, a methoxy group or a fluorine atom and n is an integer of 0 to 2,
X.sup.1 is a halogen atom and
R.sup.1 is hydrogen, a methyl group or an ethyl group.
2. The triazine compound of claim 1, wherein A is said ##STR67##
3. The triazine compound of claim 2, wherein Y.sup.4 is a methyl group.
4. The triazine compound of claim 1, wherein A is said ##STR68##
5. The triazine compound of claim 1, wherein the compound is selected from the group consisting of
2-amino-4-(.alpha.-fluoro, .alpha.-methyl ethyl)-6-[2-(3',5'-dimethylphenoxy)-1-methyl-ethylamino]-s-triazine,
2-amino-4-(.alpha.-fluoroethyl)-6-[2-(3',5'-dimethylphenoxy)-1-methyl-ethylamino]-s-triazine,
2-amino-4-(.alpha.-chloroethyl)-6-[2-(3',5'-dimethylphenoxy)-1-methyl-ethylamino]-s-triazine,
2-amino-4-(.alpha.-fluoro, .alpha.-methyl ethyl)-6-[2-(2',3'-dimethylphenoxy)-1-methyl-ethylamino]-s-triazine,
2-amino-4-(.alpha.-fluoro, .alpha.-methyl ethyl)-6-[2-(2',5'-dimethylphenoxy)-1-methyl-ethylamino]-s-triazine,
2-amino-4-(.alpha.-fluoro, .alpha.-methyl ethyl)-6-[2-(2',5'-dimethylphenoxy)-1-methyl-ethylamino]-s-triazine,
2-amino-4-(.alpha.-fluoro, .alpha.-methyl ethyl)-6-[2-(2',3'-dimethylphenoxy)-1-methyl-ethylamino]-s-triazine,
2-amino-4-(.alpha.-fluoroethyl)-6-[2-(2',3'-dimethylphenoxy)-1-methyl-ethylamino]-s-triazine,
2-amino-4-(.alpha.-chloro, .alpha.-methyl ethyl)-6-[2-(3',5'-dimethylphenoxy)-1-methyl-ethylamino]-s-triazine,
2-amino-4-(.alpha.-bromo, .alpha.-methyl ethyl)-6-[2-(3',5'-dimethylphenoxy)-1-methyl-ethylamino]-s-triazine,
2-amino-4-(.alpha.-fluoro, .alpha.-methyl ethyl)-6-[2-(3'-trifluoromethylphenoxy)-1-methyl-ethylamino]-s-triazine,
2-amino-4-(.alpha.-fluoro, .alpha.-methyl ethyl)-6-[2-(3'-methylphenoxy)-1-methyl-ethylamino]-s-triazine,
2-amino-4-(.alpha.-fluoroethyl)-6-[2-(3'-methylphenoxy)-1-methyl-ethylamino]-s-triazine,
2-amino-4-(.alpha.-fluoroethyl)-6-[2-(3'-trifluoromethylphenoxy)-1-methyl-ethylamino]-s-triazine,
2-amino-4-(.alpha.-chloro, .alpha.-methyl ethyl)-6-[2-(3'-methylphenoxy)-1-methyl-ethylamino]-s-triazine,
2-amino-4-(.alpha.-chloro, .alpha.-methyl ethyl)-6-[2-phenoxy-1-methyl-ethylamino]-s-triazine,
2-amino-4-(.alpha.-fluoro, .alpha.-methyl ethyl)-6-(2-phenoxy-1-methylethylamino]-s-triazine,
2-amino-4-(.alpha.-fluoroethyl)-6-(2-phenoxy-1-methyl-ethylamino]-s-triazine,
2-amino-4-(.alpha.-fluoro, .alpha.-methyl ethyl)-6-[2-(3'-methoxyphenoxy)-1-methyl-ethylamino]-s-triazine,
2-amino-4-(.alpha.-fluoro, .alpha.-methyl ethyl)-6-[2-(3',4'-dimethylphenoxy)-1-methyl-ethylamino]-s-triazine,
2-amino-4-(.alpha.-fluoro, .alpha.-methyl ethyl)-6-[2-(3'-fluorophenoxy)-1-methyl-ethylamino]-s-triazine,
2-amino-4-(.alpha.-fluoro, .alpha.-methyl ethyl)-6-[2-(2'-fluorophenoxy)-1-methyl-ethylamino]-s-triazine,
2-amino-4-(.alpha.-fluoro, .alpha.-methyl ethyl)-6-[2-(4'-fluorophenoxy)-1-methyl-ethylamino]-s-triazine,
2-amino-4-(.alpha.-fluoro, .alpha.-methyl ethyl)-6-[2-(3'-methoxy, 4'-methylphenyl)-1-methyl-ethylamino]-s-triazine,
2-amino-4-(.alpha.-fluoroethyl)-6-[2-(3'-methoxy, 4'-methylphenyl)-1-methyl-ethylamino]-s-triazine,
2-amino-4-(.alpha.-chloro, .alpha.-methyl)-6-[2-(3'-methoxy, 4-methylphenyl)-1-methyl-ethylamino]-s-triazine,
2-amino-4-(.alpha.-fluoro, .alpha.-methyl ethyl)-6-[2-(3'-methyl, 4'-methoxyphenyl)-1-methyl-ethylamino]-s-triazine,
2-amino-4-(.alpha.-fluoroethyl)-6-[2-(3'-methyl, 4'-methoxyphenyl)-1-methyl-ethylamino]-s-triazine, and
2-amino-4-(.alpha.-fluoro, .alpha.-methylethyl)-6-[2-(3'-methyl, 4'-methoxyphenyl)-1-methyl-ethylamino]-s-triazine.
6. A herbicidal composition comprising an effective herbicidal amount of a triazine compound of claim 1 in admixture with a carrier.
7. A herbicidal composition according to claim 6, wherein the triazine compound is selected from the group consisting of
2-amino-4-(.alpha.-fluoro, .alpha.-methyl ethyl)-6-[2-(3',5'-dimethylphenoxy)-1-methyl-ethylamino]-s-triazine,
2-amino-4-(.alpha.-fluoroethyl)-6-[2-(3',5'-dimethylphenoxy)-1-methyl-ethylamino]-s-triazine,
2-amino-4-(.alpha.-chloroethyl)-6-[2-(3',5'-dimethylphenoxy)-1-methyl-ethylamino]-s-triazine,
2-amino-4-(.alpha.-fluoro, .alpha.-methyl ethyl)-6-[2-(2',3'-dimethylphenoxy)-1-methyl-ethylamino]-s-triazine,
2-amino-4-(.alpha.-fluoro, .alpha.-methyl ethyl)-6-[2-(2',5'-dimethylphenoxy)-1-methyl-ethylamino]-s-triazine,
2-amino-4-(.alpha.-chloro, .alpha.-methyl ethyl)-6-[2-(2',5'-dimethylphenoxy)-1-methyl-ethylamino]-s-triazine,
2-amino-4-(.alpha.-chloro, .alpha.-methyl ethyl)-6-[2-(2',3'-dimethylphenoxy)-1-methyl-ethylamino]-s-triazine,
2-amino-4-(.alpha.-fluoroethyl)-6-[2-(2',3'-dimethylphenoxy)-1-methyl-ethylamino]-s-triazine,
2-amino-4-(.alpha.-chloro, .alpha.-methyl ethyl)-6-[2-(3',5'-dimethylphenoxy)-1-methyl-ethylamino]-s-triazine,
2-amino-4-(.alpha.-bromo, .alpha.-methyl ethyl)-6-[2-(3',5'-dimethylphenoxy)-1-methyl-ethylamino]-s-triazine,
2-amino-4-(.alpha.-fluoro, .alpha.-methyl ethyl)-6-[2-(3'-trifluoromethylphenoxy)-1-methyl-ethylamino]-s-triazine,
2-amino-4-(.alpha.-fluoro, .alpha.-methyl ethyl)-6-[2-(3'-methylphenoxy)-1-methyl-ethylamino]-s-triazine,
2-amino-4-(.alpha.-fluoroethyl)-6-[2-(3'-methylphenoxy)-1-methyl-ethylamino]-s-triazine,
2-amino-4-(.alpha.-fluoroethyl)-6-[2-(3'-trifluoromethylphenoxy)-1-methyl-ethylamino]-s-triazine,
2-amino-4-(.alpha.-chloro, .alpha.-methyl ethyl)-6-[2-(3'-methylphenoxy)-1-methyl-ethylamino]-s-triazine,
2-amino-4-(.alpha.-chloro, .alpha.-methyl ethyl)-6-[2-phenoxy-1-methyl-ethylamino]-s-triazine,
2-amino-4-(.alpha.-fluoro, .alpha.-methyl ethyl)-6-[2-phenoxy-1-methyl-ethylamino]-s-triazine,
2-amino-4-(.alpha.-fluoroethyl)-6-[2-phenoxy-1-methyl-ethylamino]-s-triazine,
2-amino-4-(.alpha.-fluoro, .alpha.-methyl ethyl)-6-[2-(3'-methoxyphenoxy-1-methyl-ethylamino]-s-triazine,
2-amino-4-(.alpha.-fluoro, .alpha.-methyl ethyl)-6-(2-(3',4'-dimethylphenoxy-1-methyl-ethylamino]-s-triazine,
2-amino-4-(.alpha.-fluoro, .alpha.-methyl ethyl)-6-[2-(3'-fluorophenoxy)-1-methyl-ethylamino]-s-triazine,
2-amino-4-(.alpha.-fluoro, .alpha.-methyl ethyl)-6-[2-(2'-fluorophenoxy)-1-methyl-ethylamino]-s-triazine,
2-amino-4-(.alpha.-fluoro, .alpha.-methyl ethyl)-6-[2-(4'-fluorophenoxy)-1-methyl-ethylamino]-s-triazine,
2-amino-4-[.alpha.-fluoro, .alpha.-methyl ethyl)-6-[2-(3'-methoxy, 4'-methylphenyl)-1-methyl-ethylamino]-s-triazine,
2-amino-4-(.alpha.-fluoroethyl)-6-[2-(3'-methoxy, 4'-methylphenyl)-1-methyl-ethylamino]-s-triazine,
2-amino-4-(.alpha.-chloro, .alpha.-methyl)-6-[2-(3'-methoxy, 4'-methylphenyl)-1-methyl-ethylamino]-s-triazine,
2-amino-4-(.alpha.-fluoro, .alpha.-methyl ethyl)-6-[2-(3'-methyl, 4'-methoxyphenyl)-1-methyl-ethylamino]-s-triazine,
2-amino-4-(.alpha.-fluoroethyl)-6-[2-(3'-methyl, 4'-methoxyphenyl)-1-methyl-ethylamino]-s-triazine, and
2-amino-4-(.alpha.-fluoro, .alpha.-methylethyl)-6-[2-(3'-methyl, 4'-methoxyphenyl)-1-methyl-ethylamino]-s-triazine.
8. A method of combatting weeds comprising applying to weeds or to a locus thereof an effective herbicidal amount of a triazine compound of claim 1.
9. The method of combatting weeds according to claim 8, wherein the triazine compound is selected from the group consisting of
2-amino-4-(.alpha.-fluoro, .alpha.-methyl ethyl)-6-[2-(3',5'-dimethylphenoxy)-1-methyl-ethylamino]-s-triazine,
2-amino-4-(.alpha.-fluoroethyl)-6-[2-(3',5'-dimethylphenoxy)-1-methyl-ethylamino]-s-triazine,
2-amino-4-(.alpha.-chloroethyl)-6-[2-(3',5'-dimethylphenoxy)-1-methyl-ethylamino]-s-triazine,
2-amino-4-(.alpha.-fluoro, .alpha.-methyl ethyl)-6-[2-(2',3'-dimethylphenoxy)-1-methyl-ethylamino]-s-triazine,
2-amino-4-(.alpha.-fluoro, .alpha.-methyl ethyl)-6-[2-(2',5'-dimethylphenoxy)-1-methyl-ethylamino]-s-triazine,
2-amino-4-(.alpha.-chloro, .alpha.-methyl ethyl)-6-[2-(2',5'-dimethylphenoxy)-1-methyl-ethylamino]-s-triazine,
2-amino-4-(.alpha.-chloro, .alpha.-methyl ethyl)-6-[2-(2',3'-dimethylphenoxy)-1-methyl-ethylamino]-s-triazine,
2-amino-4-(.alpha.-fluoroethyl)-6-[2-(2',3'-dimethylphenoxy)-1-methyl-ethylamino]-s-triazine,
2-amino-4-(.alpha.-chloro, .alpha.-methyl ethyl)-6-[2-(3',5'-dimethylphenoxy)-1-methyl-ethylamino]-s-triazine,
2-amino-4-(.alpha.-bromo, .alpha.-methyl ethyl)-6-[2-(3',5'-dimethylphenoxy)-1-methyl-ethylamino]-s-triazine,
2-amino-4-(.alpha.-fluoro, .alpha.-methyl ethyl)-6-[2-(3'-trifluoromethylphenoxy)-1-methyl-ethylamino]-s-triazine,
2-amino-4-(.alpha.-fluoro, .alpha.-methyl ethyl)-6-[2-(3'-methylphenoxy)-1-methyl-ethylamino]-s-triazine,
2-amino-4-(.alpha.-fluoroethyl)-6-[2-(3'-methylphenoxy)-1-methyl-ethylamino]-s-triazine,
2-amino-4-(.alpha.-fluoroethyl)-6-[2-(3'-trifluoromethylphenoxy)-1-methyl-ethylamino]-s-triazine,
2-amino-4-(.alpha.-chloro, .alpha.-methyl ethyl)-6-[2-(3'-methylphenoxy)-1-methyl-ethylamino]-s-triazine,
2-amino-4-(.alpha.-chloro, .alpha.-methyl ethyl)-6-(2-phenoxy)-1-methyl-ethylamino]-s-triazine,
2-amino-4-(.alpha.-fluoro, .alpha.-methyl ethyl)-6-(2-phenoxy)-1-methyl-ethylamino]-s-triazine,
2-amino-4-(.alpha.-fluoroethyl)-6-(2-phenoxy-1-methyl-ethylamino]-s-triazine,
2-amino-4-(.alpha.-fluoro, .alpha.-methyl ethyl)-6-[2-(3'-methoxyphenoxy)-1-methyl-ethylamino]-s-triazine,
2-amino-4-(.alpha.-fluoro, .alpha.-methyl ethyl)-6-[2-(3',4'-dimethylphenoxy)-1-methyl-ethylamino]-s-triazine,
2-amino-4-(.alpha.-fluoro, .alpha.-methyl ethyl)-6-[2-(3'-fluorophenoxy)-1-methyl-ethylamino]-s-triazine,
2-amino-4-(.alpha.-fluoro, .alpha.-methyl ethyl)-6-[2-(2'-fluorophenoxy)-1-methyl-ethylamino]-s-triazine,
2-amino-4-(.alpha.-fluoro, .alpha.-methyl ethyl)-6-[2-(4'-fluorophenoxy)-1-methyl-ethylamino]-s-triazine,
2-amino-4-(.alpha.-fluoro, .alpha.-methyl ethyl)-6-[2-(3'-methoxy, 4'-methylphenyl)-1-methyl-ethylamino]-s-triazine,
2-amino-4-(.alpha.-fluoroethyl)-6-[2-(3'-methoxy, 4'-methylphenyl)-1-methyl-ethylamino]-s-triazine,
2-amino-4-(.alpha.-chloro, .alpha.-methyl)-6-[2-(3'-methoxy, 4'-methylphenyl)-1-methyl-ethylamino]-s-triazine,
2-amino-4-(.alpha.-fluoro, .alpha.-methyl ethyl)-6-[2-(3'-methyl, 4'-methoxyphenyl)-1-methyl-ethylamino]-s-triazine,
2-amino-4-(.alpha.-fluoroethyl)-6-[2-(3'-methyl, 4'-methoxyphenyl)-1-methyl-ethylamino]-s-triazine, and
2-amino-4-(.alpha.-fluoro, .alpha.-methylethyl)-6-[2-(3'-methyl, 4'-methoxyphenyl)-1-methyl-ethylamino]-s-triazine.
10. The triazine compound of claim 3, wherein X.sup.1 is a fluorine atom or a chlorine atom, R.sup.1 is hydrogen or a methyl group and n is 2.
11. The method of combatting weeds according to claim 8, wherein the triazine compound is of the formula ##STR69## Y.sup.4 is a methyl group, R.sup.1 is a hydrogen or a methyl group and
n is 2.
12. The method of combatting weeds according to claim 11, wherein said triazine compound is applied to a soil surface in an amount of 1 g/10 ares to 100 g/10 ares.
13. The triazine compound of claim 10, wherein the compound is selected from the group consisting of
2-amino-4-(.alpha.-fluoro, .alpha.-methyl ethyl)-6-[2-(3',5'-dimethylphenoxy)-1-methyl-ethylamino]-s-triazine,
2-amino-4-(.alpha.-fluoroethyl)-6-[2-(3',5'-dimethylphenoxy)-1-methyl-ethylamino]-s-triazine and
2-amino-4-(.alpha.-chloroethyl)-6-[2-(3',5'-dimethylphenoxy)-1-methyl-ethylamino]-s-triazine.
14. The method of combatting weeds according to claim 8, wherein said triazine compound is applied to a soil surface in an amount of 1 g/10 ares to 100 g/10 ares.
15. The method of combatting weeds according to claim 8, wherein the weeds are selected from the group consisting of Alopercurus myosuroides, Digitaria sanguinalis, Abutilon theophrasti, Veronica persica, Polygonum persicaria, Viola arvensis, Amaranthus patulus and Galium sparium var. echinospermon.
16. The method of combatting weeds according to claim 9, wherein said triazine compound is applied to a soil surface in an amount of 1 g/10 ares to 100 g/10 ares and the weeds are selected from the group consisting of Alopercurus myosuroides, Digitaria sanguinalis, Abutilon theophrasti, Veronica persica, Polygonum persicaria, Viola arvensis, Amaranthus patulus and Galium sparium var. echinospermon.
17. The method of combatting weeds according to claim 16, wherein the triazine compound is selected from the group consisting of
2-amino-4-(.alpha.-fluoro, .alpha.-methyl ethyl)-6-[2-(3',5'-dimethylphenoxy)-1-methyl-ethylamino]-s-triazine,
2-amino-4-(.alpha.-fluoroethyl)-6-[2-(3',5'-dimethylphenoxy)-1-methyl-ethylamino]-s-triazine and
2-amino-4-(.alpha.-chloroethyl)-6-[2-(3',5'-dimethylphenoxy)-1-methyl-ethylamino]-s-triazine.
18. The triazine compound of claim 1, wherein X.sup.1 is a fluorine atom or a chlorine atom, R.sup.1 is hydrogen or a methyl group.
19. The triazine compound of claim 18, wherein the compound is selected from the group consisting of
2-amino-4-(.alpha.-fluoro, .alpha.-methyl ethyl)-6-[2-(3'-methoxy, 4'-methylphenyl)-1-methyl-ethylamino]-s-triazine and
2-amino-4-(.alpha.-fluoroethyl)-6-[2-(3'-methoxy, 4'-methylphenyl)-1-methyl-ethylamino]-s-triazine.
20. The method of combatting weeds according to claim 16, wherein the triazine compound is selected from the group consisting of
2-amino-4-(.alpha.-fluoro, .alpha.-methyl ethyl)-6-[2-(3'-methoxy, 4'-methylphenyl)-1-methyl-ethylamino]-s-triazine and
2-amino-4-(.alpha.-fluoroethyl)-6-[2-(3'-methoxy, 4'-methylphenyl)-1-methyl-ethylamino]-s-triazine.

Priority Claims (2)

Number	Date	Country	Kind
1-38178	Feb 1989	JPX
1-154465	Jun 1989	JPX

PCT Information

Filing Document	Filing Date	Country	Kind	102e Date	371c Date
PCT/JP90/00194	2/19/1990			10/5/1990	10/5/1990

Publishing Document	Publishing Date	Country	Kind
WO90/09378	8/23/1990

US Referenced Citations (2)

Number	Name	Date	Kind
4844731	Takematsu et al.	Jul 1989
4932998	Takematsu et al.	Jun 1990

Foreign Referenced Citations (5)

Number	Date	Country
63-51379	Mar 1988	JPX
63-146876	Jun 1988	JPX
63-238071	Oct 1988	JPX
63-264465	Nov 1988	JPX
WO8802368	Apr 1988	WOX

Non-Patent Literature Citations (1)

Entry
Chemical Abstracts, vol. 112, 1990, Takematsu et al., p. 772, abstract No. 178993v, Columbus, Ohio, US; of JP-A-01 246 279 (Oct. 1989).

Triazine derivative and a herbicide comprising the same as an effective ingredient

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