Safening mixtures of sulfonylurea and acetanilide herbicides

• US 5,256,630 A
• Filed: 12/29/1989
• Issued: 10/26/1993
• Est. Priority Date: 08/13/1987
• Status: Expired due to Fees

• Current Assignee: Monsanto Technology LLC (Bayer AG)
• Original Assignee: Monsanto Company (Bayer AG)
• Inventors: Bussler, Brett H.
• Primary Examiner(s): Raymond, Richard L.
• Assistant Examiner(s): Burn, Brian M.
• Application Number:
  US07/459,228
• Time in Patent Office: 1,397 Days
• Field of Search: 71/DIG. 1, 71/118, 71/92, 71/88, 504/130, 504/134, 504/139, 504/149, 504/131, 504/132, 504/133, 504/136, 504/137, 504/138, 504/148, 504/141, 504/140
• US Class Current: 504/134
• 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 25/32 Ingredients for reducing the noxious effect of the active substances to organisms other than pests, e.g. toxicity reducing compositions, self-destructing compositions
• CPC Class Codes: A01N 37/22 the nitrogen atom being directly attached to an aromatic ring system, e.g. anilides
• CPC Class Codes: A01N 37/26 containing the group; Thio analogues thereof
• CPC Class Codes: A01N 43/56 1,2-Diazoles; Hydrogenated 1,2-diazoles
• CPC Class Codes: A01N 43/76 1,3-Oxazoles; Hydrogenated 1,3-oxazoles
• CPC Class Codes: A01N 47/36 containing the group >N—CO—N< directly attached to at least one heterocyclic ring; Thio analogues thereof
• CPC Class Codes: C07D 205/12 condensed with carbocyclic rings or ring systems
• CPC Class Codes: C07D 209/96 Spiro-condensed ring systems
• CPC Class Codes: C07D 413/04 directly linked by a ring-member-to-ring-member bond
• CPC Class Codes: C07D 417/04 directly linked by a ring-member-to-ring-member bond
• CPC Class Codes: C07D 495/10 Spiro-condensed systems

Abstract

The disclosure herein relates to safening crops from injury by herbicidal mixtures of sulfonylurea and acetanilide herbicides by means of 5-heterocyclyl-substituted dichloroacetamide antidotes.

Claims

1. Herbicidal composition comprising

(a) a herbicidally-effective amount of a sulfonylurea of the formula ##STR4## wherein R₁ and R₂ are independently phenyl, a heterocyclic radical containing up to 10 ring members of which 4 may be O, S or N atoms or said phenyl and heterocyclic radical optionally substituted with halogen, C_1-4 alkyl, haloalkyl, alkoxy, carboxyl or carboalkoxy radicals;

(b) a herbicidally-effective amount of an acetanilide of the formula ##STR5## R₃ is hydrogen, C_1-8 alkyl, haloalkyl, alkoxy or alkoxyalkyl, alkenyl, haloalkenyl, alkynyl or haloalkynyl or acylamidoalkyl, having up to 6 carbon atoms, C_5-10 heterocyclyl or heterocyclylmethyl having O, S and/or N atoms and which may be substituted with halogen, C_1-4 alkyl, carbonylalkyl or carbonylalkoxyalkyl, nitro, amino or cyano groups;

R₄ is hydrogen, halogen, nitro, amino, C_1-6 alkyl, haloalkyl, alkoxy or alkoxyalkyl; and

n is 0-5 and

(c) an antidotally-effective amount of a compound of the formula ##STR6## and agriculturally-acceptable salts thereof wherein R₅ is halomethyl;

R₆ and R₇ are H, C_1-4 alkyl, haloalkyl, alkoxy or phenyl;

R_8-10 are H or C_1-4 alkyl;

R₁₁ is a saturated or unsaturated heterocyclic radical containing up to 10 ring atoms of which 3 may be O, S or N atoms, optionally substituted with halogen, C_1-4 alkyl, haloalkyl, alkoxy or alkoxyalkyl or with oxygen on a ring N atom or R₁₁ may be a bicyclic hydrocarbon radical containing up to 10 carbon atoms; and

R₁₀ and R₁₁ may be combined to form a spiroheterocyclic ring as defined for R₁₁.

2. Composition according to claim 1 wherein said sulfonylurea is selected from the group consisting of:

Benzenesulfonamide, 2-chloro-N-[[(4-methoxy-6-methyl-1,3,5-triazin-2-yl)amino]carbonyl];

Benzoic acid, 2-[[[[(4-chloro-6-methoxy-2-pyrimidinyl)amino]carbonyl]amino]sulfonyl]ethyl ester;

2-Thiophenecarboxylic acid, 3-[[[[(4,6-dimethoxy-1,3,5-triazin-2-yl)amino]carbonyl]amino]sulfonyl]-, methyl ester;

Benzoic acid, 2-[[[[(4,6-dimethyl-2-pyrimidinyl)amino]carbonyl]amino]sulfonyl]methyl ester;

Benzenesulfonamide, 2-(2-chloroethoxy)-N-[[(4-methoxy-6-methyl-1,3,5-triazin-2-yl) amino]carbonyl]; and

Benzoic acid, 2-[[[[(4-methoxy-6-methyl-1,3,5-triazin-2-yl)amino]carbonyl]amino]sulfonyl]methyl ester;

3. Composition according to claim 2 wherein in said compound of Formula II, R₃ is a C_1-8 alkoxyalkyl or N-containing heterocyclylmethyl radical and R₄ is a C_1-4 alkyl radical.

4. Composition according to claim 3 wherein in said compound of Formula III, R₅ is chloromethyl and R₆ and R₇ are C_1-4 alkyl or haloalkyl.

5. Composition according to claim 4 wherein said acetanilide is selected from the group consisting of

acetochlor,

alachlor,

butachlor,

metazachlor,

metolachlor and

pretilachlor.

6. Composition according to claim 5 wherein said antidotal compound is selected from the group consisting of

Oxazolidine, 3-(dichloroacetyl)-2,2-dimethyl-5-(2-furanyl)-,

Oxazolidine, 3-(dichloroacetyl)-2,2-dimethyl-5-(2-thienyl)-,

Pyridine, 3-[3-(dichloroacetyl)-2,2-dimethyl-5-oxazolidinyl]-.

7. Composition according to any one of claims 2-5 or 6 wherein said sulfonylurea is DPX-M6316 or chlorimuron ethyl, said acetanilide is acetochlor or alachlor and said antidotal compound is oxazolidine, 3-(dichloroacetyl)-2,2-dimethyl-5-(2-furanyl)-.

8. Composition according to claim 7 comprising DPX-M6316, acetochlor and oxazolidine, 3-(dichloroacetyl)-2,2-dimethyl-5-(2-furanyl).

9. Composition according to claim 7 comprising chlorimuron ethyl, acetochlor and oxazolidine, 3-(dichloroacetyl)-2,2-dimethyl-5-(2-furanyl).

10. Method for reducing phytotoxicity to crop plants due to mixtures of sulfonylurea herbicides having the formula ##STR7## wherein R₁ and R₂ are independently phenyl, a heterocyclic radical containing up to 10 ring members of which 4 may be O, S or N atoms or said phenyl and heterocyclic radical optionally substituted with halogen, C_1-4 alkyl, haloalkyl, alkoxy, carboxyl or carboalkoxy radicals;

and acetanilide herbicides having the formula ##STR8## wherein R₃ is hydrogen, C_1-8 alkyl, haloalkyl, alkoxy or alkoxyalkyl, alkenyl, haloalkenyl, alkynyl or haloalkynyl or acylamidoalkyl, having up to 6 carbon atoms, C_5-10 heterocyclyl or heterocyclylmethyl having O, S and/or N atoms and which may be substituted with halogen, C_1-4 alkyl, carbonylalkyl or carbonylalkoxyalkyl, nitro, amino or cyano groups;

R₄ is hydrogen, halogen, nitro, amino, C_1-6 alkyl, haloalkyl, alkoxy or alkoxyalkyl; and

n is 0-5

which comprises applying to the locus of the crop plant an antidotally-effective amount of a compound of the formula ##STR9## and agriculturally-acceptable salts thereof wherein R₅ is halomethyl;

R₆ and R₇ are H, C_1-4 alkyl, haloalkyl, alkoxy or phenyl;

R_8-10 are H or C_1-4 alkyl;

R₁₁ is a saturated or unsaturated heterocyclic radical containing up to 10 ring atoms of which 3 may be O, S or N atoms, optionally substituted with halogen, C_1-4 alkyl, haloalkyl, alkoxy or alkoxyalkyl or with oxygen on a ring N atom or R₁₁ may be a bicyclic hydrocarbon radical containing up to 10 carbon atoms; and

R₁₀ and R₁₁ may be combined to form a spiroheterocyclic ring as defined for R₁₁.

11. Method according to claim 10 wherein said sulfonylurea is selected from the group consisting of

Benzenesulfonamide, 2-chloro-N-[[(4-methoxy-6-methyl-1,3,5-triazin-2-yl)amino]carbonyl];

Benzoic acid, 2-[[[[(4-chloro-6-methoxy-2-pyrimidinyl)amino]carbonyl]amino]sulfonyl]ethyl ester;

2-Thiophenecarboxylic acid, 3-[[[[(4,6-dimethoxy-1,3,5-triazin-2-yl)amino]carbonyl]amino]sulfonyl]-, methyl ester;

Benzoic acid, 2-[[[[(4,6-dimethyl-2-pyrimidinyl)amino]carbonyl]amino]sulfonyl]methyl ester;

Benzenesulfonamide, 2-(2-chloroethoxy)-N-[[(4-methoxy-6-methyl-1,3,5-triazin-2-yl) amino]carbonyl]; and

Benzoic acid, 2-[[[[(4-methoxy-6-methyl-1,3,5-triazin-2-yl)amino]carbonyl]amino]sulfonyl]methyl ester;

12. Method according to claim 11 wherein in said acetanilide of Formula II, R₃ is a C_1-8 s alkoxyalkyl or N-containing heterocyclylmethyl radical and R₄ is a C_1-4 alkyl radical.

13. Method according to claim 12 wherein in said compound of Formula III, R₅ is chloromethyl and R₆ and R₇ are C_1-4 alkyl or haloalkyl.

14. Method according to claim 13 wherein said acetanilide is selected from the group consisting of

acetochlor,

alachlor,

butachlor,

metazachlor,

metolachlor and

pretilachlor.

15. Method according to claim 14 wherein said antidotal compound is selected from the group consisting of

Oxazolidine, 3-(dichloroacetyl)-2,2-dimethyl-5-(2-furanyl)-,

Oxazolidine, 3-(dichloroacetyl)-2,2-dimethyl-5-(2-thienyl)-,

Pyridine, 3-[3-(dichloroacetyl)-2,2-dimethyl-5-oxazolidinyl]-.

16. Method according to any one of claims 11-14 or 15 wherein said sulfonylurea is DPX-M6316 or chlorimuron ethyl, said acetanilide is acetochlor or alachlor and said antidotal compound is oxazolidine, 3-(dichloroacetyl)-2,2-dimethyl-5-(2-furanyl)-.

17. Method according to claim 16 wherein said mixture comprises DPX-M6316 and acetochlor and oxazolidine, 3-(dichloroacetyl)-2,2-dimethyl-5-(2-furanyl)-.

18. Method according to claim 16 wherein said mixture comprises chlorimuron and acetochlor and said antidotal compound is oxazolidine, 3-(dichloroacetyl)-2,2-dimethyl-5-(2-furanyl)-.

19. Method according to any one of claims 11-17 or 18 wherein said crop plant is corn.