IP Library Granted Patent US 6,852,674
Granted Patent B2
US 6,852,674 · App. 10/146,538 · Granted Feb 8, 2005

Herbicidal mixture comprising a benzoyl derivative, a fertilizer containing nitrogen and an adjuvant

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Quick Facts
Patent No.
US 6,852,674
App. No.
10/146,538
Granted
Feb 8, 2005
Kind
B2
Abstract

A method of controlling the growth of weeds at a locus which comprises applying to said locus a herbicidally effective amount of: (a) a benzoyl derivative of formula (I):  wherein R 1 , R 2 , R 3 , R 4 , R 5 and w are as defined in the description; (b) a fertilizer containing nitrogen; and (c) one or more adjuvants; and to their compositions thereof.

Claims (64)

1. A method of controlling the growth of weeds at a locus which comprises applying to said locus a herbicidally effective amount of:

(a) a benzoyl derivative of formula (I):

 wherein:

R 1 is a formula (II):

or R 1 is —CH 2 O(haloalkyl), —CH 2 O(alkyl)CH 2 O(cycloalkyl), —CH 2 OCH 2 (cycloalkyl), —CH 2 O(CH 2 ) 2 O(CH 2 ) 2 Oalkyl, —CH 2 S(haloalkyl), —CH 2 OCH 2 R 8 or —OCH 2 (cycloalkyl);

R 2 and R 3 independently of one another are hydrogen, halogen, cyano, nitro, —S(O) n alkyl, —S(O) n haloalkyl, alkyl, haloalkyl, alkoxy or haloalkoxy;

R 4 is hydrogen, —SO 2 alkyl, —COphenyl or —SO 2 phenyl (the phenyl groups of which are optionally substituted by alkyl, haloalkyl, alkoxy, haloalkoxy, halogen, cyano or nitro);

R 5 is hydrogen or alkyl;

R 6 is cyano, CONH 2 , NHSO 2 alkyl, NHSO 2 haloalkyl, OR 9 , CO 2 alkyl, —S(O) n alkyl or —S(O) n haloalkyl;

R 7 is hydrogen or alkyl;

R 8 is a 2-tetrahydrofuranyl, 3-tetrahydrofuranyl or 2-tetrahydropyranyl ring;

R 9 is hydrogen, alkyl, haloalkyl, alkenyl, haloalkenyl, alkynyl, cycloalkyl, cycloalkylalkyl or cycloalkenyl;

w is 1 or 2; and

n is 0, 1 or 2;

or an agriculturally acceptable salt or metal complex thereof;

(b) a fertilizer containing nitrogen; and

(c) one or more adjuvants.

2. A method according to claim 1 in which the benzoyl derivative is of formula (Ia):

wherein:

R 1 is a formula (II):

or R 1 is —CH 2 O-(halo-C 1 -C 4 -alkyl), —CH 2 O—(C 1 -C 4 -alkyl), —CH 2 O(CH 2 ) 2 O—(CH 2 ) 2 O C 1 -C 4 -alkyl, —CH 2 OCH 2 OCH 2 R 8 or —OCH 2 —(C 3 -C 6 -cycloalkyl);

R 2 is methyl, —S(O) n methyl, —S(O) n ethyl or halogen;

R 3 is trifluoromethyl, —S(O) n methyl, —S(O) n ethyl or halogen;

R 5 and R 5a are each hydrogen, methyl or ethyl;

R 6 is cyano or OR 9 ;

R 7 is hydrogen or C 1 -C 4 -alkyl;

R 8 is a 2-tetrahydrofuranyl or 3-tetrahydrofuranyl ring; and

R 9 is C 1 -C 4 -alkyl.

3. A method according to claim 1 in which the benzoyl derivative is of formula (Ia) wherein:

R 1 is a formula (II):

or R 1 is —CH 2 O-(halo-C 1 -C 4 -alkyl), —CH 2 O—(C 1 -C 4 -alkyl), —CH 2 O(CH 2 ) 2 O(CH 2 ) 2 Omethyl, —CH 2 OCH 2 R 8 or —OCH 2 (cyclopropyl);

R 2 is halogen or methyl;

R 3 is —S(O) n methyl or —S(O) n ethyl;

R 5 and R 5a are each hydrogen or methyl;

R 6 is cyano or OR 9 ;

R 7 is hydrogen or methyl;

R 8 is a 2-tetrahydrofuranyl ring; and

R 9 is methyl or ethyl.

4. A method according to claim 1 in which the benzoyl derivative is:

2-[2-chloro-3-(5-cyanomethylisoxazolin-3-yl)-4-ethylsulfonylbenzoyl]cyclohexane-1,3-dione;

2-[2-chloro-3-(2,2,2-trifluoroethoxymethyl)-4-methylsulfonylbenzoyl]cyclohexane-1,3-dione;

2-{2-chloro-4-methylsulfonyl-3-[tetrahydrofuran-2-yl]methoxymethyl]benzoyl}cyclohexane-1,3-dione;

2-[2-chloro-3-(5-ethoxymethylisoxazolin-3-yl)-4-ethylsulfonylbenzoyl]cyclohexane-1,3-dione;

2-[2-chloro-3-(2,2-difluoroethoxymethyl)-4-ethylsulfonylbenzoyl]cyclohexane-1,3-dione;

2-[2-chloro-3-(methoxyethoxyethoxymethyl)-4-methylsulfonylbenzoyl]cyclohexane-1,3-dione;

2-[2-chloro-3-(5-methoxymethyl-5-methylisoxazolin-3-yl)-4-methylsulfonylbenzoyl]-cyclohexane-1,3-dione;

2-[2-chloro-4-ethylsulfonyl-3-(5-methoxymethyl-5-methylisoxazolin-3-yl)benzoyl]-cyclohexane-1,3-dione;

2-[2-chloro-3-(5-ethoxymethyl-5-methylisoxazolin-3-yl)-4-methylsulfonylbenzoyl]-cyclohexane-1,3-dione;

2-[2-chloro-4-ethylsulfonyl-3-(5-methoxymethylisoxazolin-3-yl)benzoyl]cyclohexane-1,3-dione;

2-[2-chloro-3-cyclopropylmethoxy-4-methylsulfonylbenzoyl]-5,5-dimethylcyclo-hexane-1,3-dione;

2-[2-chloro-3-cyclopropylmethoxy-4-methylsulfonylbenzoyl]cyclohexane-1,3-dione; and

2-[2-chloro-3-(1,1,2,2,2-pentafluoroethoxymethyl)-4-methylsulfonylbenzoyl]cyclo-hexane-1,3-dione.

5. A method according to claim 1 in which the adjuvant is a surfactant or organic liquid.

6. A method according to claim 5 in which the adjuvant is a surfactant selected from polyoxyethylene sobitan monolaurates; alkylaryl-polyoxyethylenes; paraffin based petroleum oil; polyoxyethylated polyol fatty acids and polyol fatty esters; crop oil concentrate; and silicone based additives.

7. A method according to claim 1 in which the fertilizer is a nitrogen solution.

8. A method according to claim 7 in which the fertilizer is urea ammonium nitrate (UAN) wherein the % N is from 28% to 33%; ammonium sulfate, urea or mixtures thereof.

9. A composition comprising:

(a) a herbicidally effective amount of a benzoyl derivative of formula (I) as defined in claim 1 or an agriculturally acceptable salt or metal complex thereof;

(b) a fertilizer containing nitrogen

(c) one or more adjuvants.

10. A product comprising:

(a) a herbicidally effective amount of a benzoyl derivative of formula (I) as defined in claim 1 or an agriculturally acceptable salt or metal complex thereof;

(b) a fertilizer containing nitrogen

(c) one or more adjuvants as a combined preparation for separate, simultaneous or sequential use in the control of weeds at a locus.

Assignments (4)
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Feb 6, 2015
From: BAYER CROPSCIENCE AG
To: BAYER INTELLECTUAL PROPERTY GMBH
Reel/Frame 034914/0354 →
CHANGE OF NAME Recorded Nov 12, 2008
From: BAYER CROPSCIENCE GMBH
To: BAYER CROPSCIENCE AG
Reel/Frame 021838/0869 →
CHANGE OF NAME Recorded Nov 12, 2008
From: AVENTIS CROPSCIENCE GMBH
To: BAYER CROPSCIENCE GMBH
Reel/Frame 021924/0762 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Sep 3, 2002
From: BICKERS, UDO; HACKER, ERWIN; SIXL, FRANK; AULER, THOMAS
To: AVENTIS CROPSCIENCE GMBH
Reel/Frame 013261/0140 →