# US 5,344,810 A · Herbicidal compositions and methods of combating weeds > Agents: this data is available as JSON from the patentgrep API and MCP server — see https://patentgrep.com/llms.txt - Number: US 5,344,810 A - Document ID: US5344810A - Status: Granted - Kind: A - Application number: 08/031,016 - Filed: 1993-03-11 - Granted: 1994-09-06 - Earliest claimed: 1990-08-01 - Assignees: Idemitsu Kosan Co., Ltd. - Inventors: Toshihiro Hirata; Izumi Kobayashi; Nobuyuki Kikkawa; Tetsuo Takematsu - Web page: https://patentgrep.com/patent/US5344810A ## CPC - A01N 43/68: with two or three nitrogen atoms directly attached to ring carbon atoms - A01N: PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF (preservation of food or foodstuff A23); BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES (preparations for medical, dental or toiletry purposes which kill or prevent the growth or proliferation of unwanted organisms A61K); PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS ## Abstract Herbicidal compositions comprising as active ingredients a triazine derivative represented by general formula [I]: ##STR1## and compound represented by general formula [II]: ##STR2## By synergistic effects of active ingredients, the herbicidal compositions show a high herbicidal effect at low dosage and have such a wide range of herbicidal spectrum that the compositions exhibit their high herbicidal effect not only against broad-leaved weeds but also against Gramineae weeds, etc. The compositions have flexibility of treatment to exhibit effectiveness as compared to known herbicides for field crops and crops are free from injury. ## Claims ### Claim 1 A herbicidal composition for combatting weeds selected from the group consisting of Abution theophrasti, ipomea Pureurea, Galium aparine L. and Viola arvensis comprising as active ingredients a herbicidally effective amount of a triazine compound represented by general formula (I): ##STR24## wherein A represents ##STR25## wherein Z.sup.1 represents oxygen atom or sulfur atom, or ##STR26## wherein X.sup.2 represents methyl group or fluorine atom and n represents 0 or an integer of 1 or 2; R.sup.1 represents hydrogen atom or methyl group; and X.sup.1 represents fluorine atom or chlorine atom and a herbicidally effective amount of a compound represented by general formula (II): ##STR27## wherein Z.sup.2 represents a nitrogen atom or CH, R.sup.2 represents a fluorine atom, a chlorine atom, methyl group, methoxy group or amino group, R.sup.3 represents a hydrogen atom, methyl group, NH.sub.4, an alkali metal or NH(CH.sub.3).sub.2, m represents an integer of 1 to 4 and l represents 0 or 1. ### Claim 2 (depends on 1) The herbicidal composition as claimed in claim 1, wherein the triazine compound to the compound of formula (II) is in a weight ratio of 10:1 to 1:100; the triazine compound is 2-amino-4-(.alpha.-fluoro, .alpha.-methylethyl)-6-(2-(3,',5'-dimethylphenoxy)-1-methylethylamino)-s-t riazine and the compound of formula (II) is 3,6-dichloro-2-methoxybenzoic acid. ### Claim 3 (depends on 1) The herbicidal composition as claimed in claim 1, wherein the triazine compound represented by general formula (I) is a triazine compound selected from the group consisting of 2-amino-4-[1-(benzofuran-2'-yl )ethylamino ]-6-(.alpha.-fluoro, .alpha.-methylethyl )-s-triazine, 2'-yl )ethylamino ]-6-( .alpha.-fluoroethyl )-s-triazine, 2-amino-4-[1-( benzothiophen-2'-yl )ethylamino ]-6-( .alpha.-fluoro, .alpha.-methylethyl)-s-triazine, 2-amino-4-( .alpha.-fluoro, .alpha.-methylethyl)-6-[2-(3,5'-dimethylphenoxy)-1-methylethylamino] -s-triazine, 2-amino-4-( .alpha.-fluoro, .alpha.- methylethyl)-6-[2-(3,40 ,5')-1-methylethylamino ]-s-triazine and 2-amino-4( (.alpha.-fluoro, .alpha.-methylethyl )-6-[2-( 3', 5'-dimethylphenoxy )-1methylethylamino ]-s-triazine and 2-amino-4(.alpha.-fluoro, .alpha.-methylethyl-6-[2-(3,40 ,5'-dimethlphenoxy)-1-methylethylamino]-S-triazine. ### Claim 4 (depends on 3) The herbicidal composition as claimed in claim 3, wherein the triazine compound to the compound of formula (II) is in a weight ratio of 10:1 to 1:100 and wherein the compound represented by formula (II) is a compound selected from the group consisting of 2,3,6-trichlorobenzoic acid; 3,6-dichloro-2methoxybenzoic acid; 3-amino-2,5-dichlorobenzoic acid; 2,3,5-trichloro-6-methoxybenzoic acid; 4-amino-3,5,6-trichloro-2-pyridinecarboxylic acid; 3,6-dichloro-2-pyridinecarboxylic acid; (3,5,6-trichloro-2-pyridinyl)-oxyacetic acid and (4-amino-3,5-dichloro-6-fluoro-2-pyridinyl)oxyacetic acid. ### Claim 5 (depends on 1) The herbicidal composition as claimed in claim 1, wherein the compound represented by general formula (II) is a compound selected from the group consisting of 2,3,6-trichlorobenzoic acid; 3,6-dichloro-2-methoxybenzoic acid; 3-amino-2,5-dichlorobenzoic acid; 2,3,5-trichloro-6--methoxybenzoic acid; 4-amino-3,5,6-trichloro-2-pyridinecarboxylic acid; 3,6-dichloro-2-pyridinecarboxylic acid; (3,5,6-trichloro-2-pyridinyl)-oxyacetic acid and (4-amino-3,5-dichloro-6-fluoro-2-pyridinyl)oxyacetic acid. ### Claim 6 (depends on 1) The herbicidal composition as claimed in claim 1, wherein the triazine compound of said formula (I) to the compound of said formula (II) is in a weight ratio of 10:1 to 1:100. ### Claim 7 (depends on 1) The herbicidal composition as claimed in claim 1, wherein the triazine compound to the compound of formula (II) is in a weight ratio of 10:1 to 1:100; the triazine compound is 2-amino-4- ( 1-( benzofuran-2'-yl)ethylamino )-6-(.alpha.-fluoro, .alpha.-methylethyl)-s-triazine and the compound of formula (II) is 3,6-dichloro-2-methoxybenzoic acid. ### Claim 8 (depends on 1) The herbicidal composition as claimed in claim 1, wherein the triazine compound to the compound of formula (II) is in a weight ratio of 10:1 to 1:100; the triazine compound is 2-amino-4-(1- ( benzofuran-2'-yl ) ethylamino ) -6- ( .alpha.-fluoroethyl)-s-triazine and the compound of formula (II) is 3,6-dichloro-2-pyridinecarboxylic acid. ### Claim 9 (depends on 1) The herbicidal composition as claimed in claim 1, wherein the triazine compound to the compound of formula (II) is in a weight ratio of 10:1 to 1:100; the triazine compound is 2-amino-4-( 1-(benzothiophen-2'-yl)ethylamino) -6-(.alpha.-fluoro, .alpha.-methylethyl)-s-triazine and the compound of formula ( II ) is ( 4-amino-3,5-dichloro-6-fluoro-2-pyridinyl ) oxyacetic acid. ### Claim 10 (depends on 1) The herbicidal composition as claimed in claim 1, wherein the triazine compound to the compound of formula ( II ) is in a weight ratio of 10: 1 to 1: 100; the triazine compound is 2-amino-4- (d-fluoro, .alpha.-methylethyl-6- (2-3',5'-dimethylphenoxy)-1-methylethylamino)-s-triazine and the compound of formula ( II ) is 3,6-dichloro-2-methoxybenzoic acid. ### Claim 11 (depends on 1) The herbicidal composition as claimed in claim 1, wherein the triazine compound to the compound of formula (II) is in a weight ratio of 10: 1 to 1: 100; the triazine compound is 2 -amino-4- (.alpha.-fluoro , .chi.-methylethyl ) -6- (2- (3 '-fluorophenoxy 1-methylethylamino ) -s -triazine and the compound of formula ( II ) is 3,6-dichloro-2-pyridinecarboxylic acid. ### Claim 12 (depends on 1) The herbicidal composition as claimed in claim 1, wherein the triazine compound to the compound of formula (II) is in a weight ratio of 10: 1 to 1: 100; the triazine compound is 2-amino-4- (.alpha.-chloro , .chi.-methylethyl ) -6- (2- (3 ', 5 '-dimethylphenoxy)-1-methylethylamino)-s-triazine and the compound of formula ( II ) is ( 4-amino-3,5-dichloro-6-fluoro-2-pyridinyl ) -oxyacetic acid. ### Claim 13 (depends on 1) The herbicidal composition as claimed in claim 1, wherein the triazine compound to the compound of formula (II) is in a weight ratio of 10:1 to 1:100; the triazine compound is 2-amino-4- ( .alpha.-fluoro, .alpha.-methylethyl ) -6- ( 2- (3',5'-dimethylphenoxy) -1-methylethyethylamino)-s-triazine and the compound of formula (II) is 3,6-dichloro-2-pyridinecarboxylic acid. ### Claim 14 (depends on 1) The herbicidal composition as claimed in claim 1, wherein the triazine compound to the compound of formula (II) is in a weight ratio of 10:1 to 1:100; the triazine compound is 2-amino-4-(.chi.-fluoro, .alpha.-methylethyl)-6-( 2-( 3', 5'-dimethylphenoxy -1-methylethylamino ) -s-triazine and the compound of formula ( II ) is ( 4-amino-3,5-dichloro-6-fluoro-2-pyridinyl ) -oxyacetic acid. ### Claim 15 (depends on 1) The herbicidal composition as claimed in claim 1, wherein the triazine compound of formula (I) is 2-amino-4-(.alpha.-fluoro, .alpha.-methylethyl)-6-(2-(3,40 5,40 -dimethylphenoxy)-1-methylethylamino)-s-triazine and the compound of formula (II) is a compound selected from the group consisting of 2,3,6-trichlorobenzoic acid; 3,6-dichloro--2-methoxybenzoic acid; 3-amino-2,5-dichlorobenzoic acid; 2,3,5-trichloro-6-methoxybenzoic acid; 4-amino-3,5,6-trichloro-2-pyridinecarboxylic acid; 3,6-dichloro-2-pyridinecarboxylic acid; (3,5,6-trichloro-2-pyridinyl)-oxyacetic acid and (4-amino-3,5-dichloro-6-fluoro2-pyridinyl)oxyacetic acid. ### Claim 16 (depends on 1) A method of combatting weeds selected from the group consisting of Abutilon theophrasti, Ipomea Purpurea, Galium aparine L, and Viola arvensis, comprising applying to said weeds or to a locus thereof an effective herbicidal amount of the composition according to claim 1. ### Claim 17 (depends on 16) The method as claimed in claim 16, wherein the triazine compound represented by formula (I) is a triazine derivative selected from the group consisting of 2-amino-4-(1-(benzofuran 2'-yl)ethylamino)-6-(.alpha.-fluoro, .alpha.-methylethyl)-s-triazine, 2-amino-4-(1(benzofuran-2'-yl) ethylamino)-6-(.alpha.-fluoroethyl)-s-triazine, 2-amino-4-(1-(benzothiophen-2'-yl)ethylamino)-6-(.alpha.-fluoro,.alpha.-me thylethyl)-s-triazine, 2-amino-4-.alpha.-fluoro,60-methylethyl)-6-(2-( 3', 5'-dimethylphenoxy)-1-methylethylamino)-s-triazine, 2-amino 4-(.alpha.-fluoro, .alpha.-methylethyl)-6-(2-(3'fluorophenoxy)-1 methylethylamino)-s-triazine, 2-amino-4-(.alpha.-chloro, .alpha.-methylethyl) 6-(2-(3',5'-dimethylphenoxy)-1-methylethylamino)-s-triazine and 2-amino-4-(.alpha.-fluoro, .alpha.-methylethyl)-6-(2-(3',5'-dimethylphenoxy) -1-methylethylamino)-s-triazine; and the compound represented by formula (II) is a compound selected from the group consisting of 2,3,6-trichlorobenzoic acid; 3,6-dichloro-2-methoxybenzoic acid; 3-amino-2,5-dichlorobenzoic acid; 2,3,5-trichloro-6methoxybenzoic acid; 4-amino-3,5,6-trichloro-2-pyridinecarboxylic acid; 3,6-dichloro-2-pyridinecarboxylic acid; (3,5,6-trichloro-2pyridinyl)-oxyacetic acid and (4-amino-3,5-acid. ### Claim 18 (depends on 17) The method as claimed in claim 17, wherein the triazine compound to the compound of formula (II) is in a weight ratio of 10:1 to 1:100; and the compound represented by formula (II) is a compound selected from the group consisting of 2,3,6-trichlorobenzoic acid; 3,6-dichloro-2-methoxybenzoic acid; 3-amino-2,5-dichlorobenzoic acid; 2,3,5-trichloro-6-methoxybenzoic acid; 4-amino-3,5,6-trichloro-2-pyridinecarboxylic acid; 3,6-dichloro-2-pyridinecarboxylic acid; (3,5,6-trichloro-2-pyridinyl)-oxyacetic acid and (4-amino-3,5-dichloro-6-fluoro-2pyridinyl)oxyacetic acid. ### Claim 19 (depends on 16) The method as claimed in claim 16, wherein the triazine compound is 2-amino-4-(.alpha.-4-fluoro, .alpha.-methylethyl)-6-(2-(3',5'-dimethylphenoxy)-1-methylethylamino-s-tri azine; the compound of formula (II) is 3,6-dichloro-2-methoxybenzoic acid and the triazine compound to the compound of formula II is in a weight ratio of 10:1 to 1:100. ### Claim 20 (depends on 16) The method as claimed in claim 16, wherein the triazine compound of said formula (I) to the compound of said formula (II) is in a weight ratio of 10:1 to 1:100. ### Claim 21 (depends on 16) The method as claimed in claim 16, wherein the compound of said formula (II) is distributed in an amount of from 10 to 20 g/10a. ### Claim 22 (depends on 16) The method as claimed in claim 16 wherein the triazine compound is 2-amino-4-( 1-(benzofuran-2'-yl) ethylamino ) -6-(.alpha.-fluoro, .alpha.-methylethyl ) -s-triazine; the compound of formula (II) is 3,6-dichloro-2-methoxybenzoic acid. ### Claim 23 (depends on 16) The method as claimed in claim 16, wherein the triazine compound is 2-amino-4-(1-(benzofuran-2'-yl) ethylamino ) -6- (.alpha.-fluoroethyl) -s-triazine; the compound of formula (II) is 3,6-dichloro-2-pyridinecarboxylic acid. ### Claim 24 (depends on 16) The method as claimed in claim 16, wherein the triazine compound is 2-amino-4- ( 1-(benzothiophen-2 '-yl) ethylamino ) -6- ( .alpha.-fluoro, .alpha.-methylethyl ) -s-triazine; the compound of formula (II) is (4-amino-3,5-dichloro-6-fluoro2-pyridinyl) -oxyacetic acid. ### Claim 25 (depends on 16) The method as claimed in claim 16, wherein the triazine compound is 2-amino-4- ( .alpha.-fluoro, .alpha.-methylethyl-6- (2 3',5'-dimethylphenoxy )-1-methylethylamino)-s-triazine; the compound of formula ( II ) is 3,6-dichloro-2-methoxybenzoic acid. ### Claim 26 (depends on 16) The method as claimed in claim 16, wherein the triazine compound is 2-amino-4- (.alpha.(-fluoro, .alpha.-methylethyl) -6-2-(3'-fluorophenoxy)-1-methylethylamino)-s-triazine; the compound of formula (II) is 3,6-dichloro-2-pyridinecarboxylic acid. ### Claim 27 (depends on 16) The method as claimed in claim 16, wherein the triazine compound is 2-amino-4-( .alpha.-chloro, .alpha.-methylethyl)-6 2- (3', 5'-dimethylphenoxy ) -1-methylethylamino ) -s-triazine; the compound of formula (II) is (4-amino-3,5-dichloro-6-fluoro-2-pyridinyl)-oxyacetic acid. ### Claim 28 (depends on 16) The method as claimed in claim 16, wherein the triazine compound is 2-amino-4- (.alpha.-fluoro, .alpha.-methylethyl ) -6-(2- (3 ', 5 '-dimethylphenoxy ) -1-methylethylamino )-s-triazine; the compound of formula (II) is 3,6-dichloro-2-pyridinecarboxylic acid. ### Claim 29 (depends on 16) The method as claimed in claim 16, wherein the triazine compound is 2-amino-4-(.alpha.-fluoro, .alpha.-methylethyl ) -6-(2- (3', 5'-dimethylphenoxy)- b 1-methylethylamino )-s-triazine: the compound of formula (II) is (4-amino-3,5-dichloro-6fluoro-2-pyridinyl ) -oxyacetic acid. ### Claim 30 (depends on 16) The method as claimed in claim 16, wherein the triazine compound of formula (I) is 2-amino-4-(.alpha.-fluoro, .alpha.-methylethyl)-6(2-(3',5'-dimethylphenoxy) -1-methylethylamino)-s-triazine and the compound of formula (II) is a compound selected from the group consisting of 2,3,6-trichlorobenzoic acid; 3,6-dichloro-2-methoxybenzoic acid; 3-amino-2,5-dichlorobenzoic acid; 2,3,5-trichloro-6-1-methoxybenzoic acid; 4-amino-3,5,6-trichloro-2-pyridinecarboxylic acid; 3,6-dichloro2-pyridinecarboxylic acid; (3,5,6-trichloro-2-pyridinyl)-oxyacetic acid and (4-amino-3,5-dichloro-6-fluoro2-pyridinyl)oxyacetic acid.