Herbicidal compositions and methods of combating weeds

• US 5,344,810 A
• Filed: 03/11/1993
• Issued: 09/06/1994
• Est. Priority Date: 08/01/1990
• Status: Expired due to Fees

• Current Assignee: Idemitsu Kosan Company Limited
• Original Assignee: Idemitsu Kosan Company Limited
• Inventors: Kikkawa, Nobuyuki, Kobayashi, Izumi, Hirata, Toshihiro, Takematsu, Tetsuo
• Primary Examiner(s): Raymond, Richard L.
• Assistant Examiner(s): CLARDY, S
• Application Number:
  US08/031,016
• Time in Patent Office: 544 Days
• Field of Search: 504/135
• US Class Current: 504/135
• CPC Class Codes: A01N 2300/00 Combinations or mixtures of active ingredients covered by classes A01N27/00 - A01N65/48 with other active or formulation relevant ingredients, e.g. specific carrier materials or surfactants, covered by classes A01N25/00 - A01N65/48
• CPC Class Codes: A01N 37/10 Aromatic or araliphatic carboxylic acids, or thio analogues thereof; Derivatives thereof
• CPC Class Codes: A01N 37/40 having at least one carboxylic group or a thio analogue, or a derivative thereof, and one oxygen or sulfur atom attached to the same aromatic ring system
• CPC Class Codes: A01N 37/44 containing at least one carboxylic group or a thio analogue, or a derivative thereof, and a nitrogen atom attached to the same carbon skeleton by a single or double bond, this nitrogen atom not being a member of a derivative or of a thio analogue of a carboxylic group, e.g. amino-carboxylic acids
• CPC Class Codes: A01N 39/04 Aryloxy-acetic acids; Derivatives thereof
• CPC Class Codes: A01N 43/40 six-membered rings
• CPC Class Codes: A01N 43/68 with two or three nitrogen atoms directly attached to ring carbon atoms

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

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 Z¹ represents oxygen atom or sulfur atom, or ##STR26## wherein X² represents methyl group or fluorine atom and n represents 0 or an integer of 1 or 2;

R¹ represents hydrogen atom or methyl group; and

X¹ represents fluorine atom or chlorine atom and a herbicidally effective amount of a compound represented by general formula (II);

##STR27## wherein Z² represents a nitrogen atom or CH, R² represents a fluorine atom, a chlorine atom, methyl group, methoxy group or amino group, R³ represents a hydrogen atom, methyl group, NH₄, an alkali metal or NH(CH₃)₂, m represents an integer of 1 to 4 and l represents 0 or 1.

2. 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-(α

-fluoro, α

-methylethyl)-6-(2-(3,'"'"',5'"'"'-dimethylphenoxy)-1-methylethylamino)-s-triazine and the compound of formula (II) is 3,6-dichloro-2-methoxybenzoic acid.

3. 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-(α

-fluoro, α

-methylethyl )-s-triazine, 2'"'"'-yl )ethylamino ]-6-( α

-fluoroethyl )-s-triazine, 2-amino-4-[1-( benzothiophen-2'"'"'-yl )ethylamino ]-6-( α

-fluoro, α

-methylethyl)-s-triazine, 2-amino-4-( α

-fluoro, α

-methylethyl)-6-[2-(3,5'"'"'-dimethylphenoxy)-1-methylethylamino] -s-triazine, 2-amino-4-( α

-fluoro, α

- methylethyl)-6-[2-(3,40 ,5'"'"')-1-methylethylamino ]-s-triazine and 2-amino-4( (α

-fluoro, α

-methylethyl )-6-[2-( 3'"'"', 5'"'"'-dimethylphenoxy )-1methylethylamino ]-s-triazine and 2-amino-4(α

-fluoro, α

-methylethyl-6-[2-(3,40 ,5'"'"'-dimethlphenoxy)-1-methylethylamino]-S-triazine.

4. 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.

5. 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.

6. 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.

7. 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-(α

-fluoro, α

-methylethyl)-s-triazine and the compound of formula (II) is 3,6-dichloro-2-methoxybenzoic acid.

8. 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- ( α

-fluoroethyl)-s-triazine and the compound of formula (II) is 3,6-dichloro-2-pyridinecarboxylic acid.

9. 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-(α

-fluoro, α

-methylethyl)-s-triazine and the compound of formula ( II ) is ( 4-amino-3,5-dichloro-6-fluoro-2-pyridinyl ) oxyacetic acid.

10. 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, α

-methylethyl-6- (2-3'"'"',5'"'"'-dimethylphenoxy)-1-methylethylamino)-s-triazine and the compound of formula ( II ) is 3,6-dichloro-2-methoxybenzoic acid.

11. 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- (α

-fluoro , χ

-methylethyl ) -6- (2- (3 '"'"'-fluorophenoxy 1-methylethylamino ) -s -triazine and the compound of formula ( II ) is 3,6-dichloro-2-pyridinecarboxylic acid.

12. 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- (α

-chloro , χ

-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.

13. 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- ( α

-fluoro, α

-methylethyl ) -6- ( 2- (3'"'"',5'"'"'-dimethylphenoxy) -1-methylethyethylamino)-s-triazine and the compound of formula (II) is 3,6-dichloro-2-pyridinecarboxylic acid.

14. 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-(χ

-fluoro, α

-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.

15. The herbicidal composition as claimed in claim 1, wherein the triazine compound of formula (I) is 2-amino-4-(α

-fluoro, α

-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.

16. 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.

17. 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-(α

-fluoro, α

-methylethyl)-s-triazine, 2-amino-4-(1(benzofuran-2'"'"'-yl) ethylamino)-6-(α

-fluoroethyl)-s-triazine, 2-amino-4-(1-(benzothiophen-2'"'"'-yl)ethylamino)-6-(α

-fluoro,α

-methylethyl)-s-triazine, 2-amino-4-α

-fluoro,60-methylethyl)-6-(2-( 3'"'"', 5'"'"'-dimethylphenoxy)-1-methylethylamino)-s-triazine, 2-amino 4-(α

-fluoro, α

-methylethyl)-6-(2-(3'"'"'fluorophenoxy)-1 methylethylamino)-s-triazine, 2-amino-4-(α

-chloro, α

-methylethyl) 6-(2-(3'"'"',5'"'"'-dimethylphenoxy)-1-methylethylamino)-s-triazine and 2-amino-4-(α

-fluoro, α

-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.

18. 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.

19. The method as claimed in claim 16, wherein the triazine compound is 2-amino-4-(α

-4-fluoro, α

-methylethyl)-6-(2-(3'"'"',5'"'"'-dimethylphenoxy)-1-methylethylamino-s-triazine;

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.

20. 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.

21. 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.

22. The method as claimed in claim 16 wherein the triazine compound is 2-amino-4-( 1-(benzofuran-2'"'"'-yl) ethylamino ) -6-(α

-fluoro, α

-methylethyl ) -s-triazine;

the compound of formula (II) is 3,6-dichloro-2-methoxybenzoic acid.

23. The method as claimed in claim 16, wherein the triazine compound is 2-amino-4-(1-(benzofuran-2'"'"'-yl) ethylamino ) -6- (α

-fluoroethyl) -s-triazine;

the compound of formula (II) is 3,6-dichloro-2-pyridinecarboxylic acid.

24. The method as claimed in claim 16, wherein the triazine compound is 2-amino-4- ( 1-(benzothiophen-2 '"'"'-yl) ethylamino ) -6- ( α

-fluoro, α

-methylethyl ) -s-triazine;

the compound of formula (II) is (4-amino-3,5-dichloro-6-fluoro2-pyridinyl) -oxyacetic acid.

25. The method as claimed in claim 16, wherein the triazine compound is 2-amino-4- ( α

-fluoro, α

-methylethyl-6- (2 3'"'"',5'"'"'-dimethylphenoxy )-1-methylethylamino)-s-triazine;

the compound of formula ( II ) is 3,6-dichloro-2-methoxybenzoic acid.

26. The method as claimed in claim 16, wherein the triazine compound is 2-amino-4- (α

(-fluoro, α

-methylethyl) -6-2-(3'"'"'-fluorophenoxy)-1-methylethylamino)-s-triazine;

the compound of formula (II) is 3,6-dichloro-2-pyridinecarboxylic acid.

27. The method as claimed in claim 16, wherein the triazine compound is 2-amino-4-( α

-chloro, α

-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.

28. The method as claimed in claim 16, wherein the triazine compound is 2-amino-4- (α

-fluoro, α

-methylethyl ) -6-(2- (3 '"'"', 5 '"'"'-dimethylphenoxy ) -1-methylethylamino )-s-triazine;

the compound of formula (II) is 3,6-dichloro-2-pyridinecarboxylic acid.

29. The method as claimed in claim 16, wherein the triazine compound is 2-amino-4-(α

-fluoro, α

-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.

30. The method as claimed in claim 16, wherein the triazine compound of formula (I) is 2-amino-4-(α

-fluoro, α

-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.