IP Library Granted Patent US 8,629,084
Granted Patent B2
US 8,629,084 · App. 11/663,029 · Granted Jan 14, 2014

Iodine-phenyl-substituted cyclic cetoenols

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Quick Facts
Patent No.
US 8,629,084
App. No.
11/663,029
Granted
Jan 14, 2014
Kind
B2
Abstract

The invention relates to novel iodophenyl-substituted cyclic ketenols of the formula (I) in which CKE, J, X and Y are as defined above, to a plurality of processes and intermediates for their preparation and to their use as pesticides and/or herbicides, and also to selective herbicidal compositions comprising firstly iodophenyl-substituted cyclic ketonols of the formula (I) and secondly at least one crop plant compatibility-improving compound.

Claims (742)

1. A compound of the formulae (I-1-a), (I-1-b) or (I-1-c):

Wherein

A, B, D, J, X and Y have the meanings given in the table:

Com-

pound

J

X

Y

D

A

B

I-1-a-1 

2-I

H

H

H

—(CH 2 ) 2 —CHOCH 3 —(CH 2 ) 2 —

I-1-a-2 

4-I

2-C 2 H 5

6-CH 3

H

—(CH 2 ) 2 —CHOCH 3 —(CH 2 ) 2 —

I-1-a-3 

2-I

4-CH 3

6-CH 3

H

—(CH 2 ) 2 —CHCH 3 —(CH 2 ) 2 —

I-1-a-5 

2-I

5-CH 3

H

H

—(CH 2 ) 2 —CHOCH 3 —(CH 2 ) 2 —

I-1-a-6 

2-I

5-CH 3

H

H

—(CH 2 ) 2 —O—(CH 2 ) 2 —

I-1-a-7 

2-I

4-Cl

6-C 2 H 5

H

—(CH 2 ) 2 —O—(CH 2 ) 2 —

I-1-a-8 

2-I

4-Cl

6-C 2 H 5

H

—(CH 2 ) 2 —CHOCH 3 —(CH 2 ) 2 —

I-1-a-10

3-I

6-CH 3

H

H

—(CH 2 ) 2 —CHOCH 3 —(CH 2 ) 2 —

I-1-a-11

4-I

2-C 2 H 5

6-CH 3

H

—(CH 2 ) 2 —O—(CH 2 ) 2 —

I-1-a-12

4-I

2-C 2 H 5

6-CH 3

H

CH 3

CH 3

I-1-a-13

4-I

2-C 2 H 5

6-CH 3

H

CH 3

I-1-a-14

4-I

2-C 2 H 5

6-CH 3

H

n-C 3 H 7

CH 3

I-1-a-15

4-I

2-C 2 H 5

6-CH 3

H

I-1-a-16

4-I

2-C 2 H 5

6-CH 3

H

—(CH 2 ) 5 —

I-1-a-17

4-I

2-C 2 H 5

6-CH 3

H

—(CH 2 ) 2 —CHCH 3 —(CH 2 ) 2 —

I-1-a-18

4-I

2-CH 3

6-CH 3

H

—(CH 2 ) 2 —CHOCH 3 —(CH 2 ) 2 —

I-1-a-19

4-I

2-CH 3

6-CH 3

H

—(CH 2 ) 2 —O—(CH 2 ) 2 —

I-1-a-20

4-I

2-C 2 H 5

6-Cl

H

—(CH 2 ) 2 —O—(CH 2 ) 2 —

I-1-a-21

4-I

2-CH 3

6-CH 3

H

—CH 2 —CHOC 4 H 9 —(CH 2 ) 3 —

I-1-a-23

4-I

2-C 2 H 5

6-CH 3

H

—CH 2 —CHOC 4 H 9 —(CH 2 ) 3 —

I-1-a-24

4-I

2-C 2 H 5

6-Cl

H

—(CH 2 ) 2 —CHOCH 3 —(CH 2 ) 2 —

I-1-a-26

4-I

2-C 2 H 5

6-CH 3

H

i-C 3 H 7

CH 3

I-1-a-27

4-I

2-C 2 H 5

6-CH 3

H

i-C 4 H 9

CH 3

wherein

A, B, D, R 1 , J, X and Y have the meanings given in the table:

Com-

pound

J

X

Y

D

I-1-b-1 

2-I

5-CH 3

H

H

I-1-b-2 

2-I

5-CH 3

H

H

I-1-b-3 

2-I

4-Cl

6-C 2 H 5

H

I-1-b-4 

2-I

4-Cl

6-C 2 H 5

H

I-1-b-5 

4-I

2-C 2 H 5

6-CH 3

H

I-1-b-6 

4-I

2-C 2 H 5

6-CH 3

H

I-1-b-7 

4-I

2-CH 3

6-CH 3

H

I-1-b-8 

4-I

2-CH 3

6-CH 3

H

I-1-b-9 

4-I

2-CH 3

6-CH 3

H

I-1-b-10

4-I

2-CH 3

6-CH 3

H

I-1-b-11

4-I

2-C 2 H 5

6-CH 3

H

I-1-b-12

4-I

2-C 2 H 5

6-Cl

H

I-1-b-13

4-I

2-C 2 H 5

6-CH 3

H

I-1-b-14

4-I

2-C 2 H 5

6-CH 3

H

I-1-b-15

4-I

2-C 2 H 5

6-CH 3

H

I-1-b-16

4-I

2-C 2 H 5

6-CH 3

H

I-1-b-17

4-I

2-C 2 H 5

6-CH 3

H

I-1-b-18

4-I

2-C 2 H 5

6-CH 3

H

I-1-b-19

4-I

2-C 2 H 5

6-CH 3

H

I-1-b-20

4-I

2-C 2 H 5

6-CH 3

H

I-1-b-21

4-I

2-C 2 H 5

6-CH 3

H

I-1-b-22

4-I

2-C 2 H 5

6-CH 3

H

Com-

pound

A

B

R 1

I-1-b-1 

—(CH 2 ) 2 —CHOCH 3 —(CH 2 ) 2 —

I-1-b-2 

—(CH 2 ) 2 —CHOCH 3 —(CH 2 ) 2 —

i-C 3 H 7

I-1-b-3 

—(CH 2 ) 2 —CHOCH 3 —(CH 2 ) 2 —

H 3 C—O—CH 2 —

I-1-b-4 

—(CH 2 ) 2 —O—(CH 2 ) 2 —

H 3 C—O—CH 2 —

I-1-b-5 

—(CH 2 ) 2 —O—(CH 2 ) 2 —

i-C 3 H 7

I-1-b-6 

C 3 H 7

CH 3

i-C 3 H 7

I-1-b-7 

—CH 2 —CH—OC 4 H 9 —(CH 2 ) 3 —

H 3 C—O—CH 2 —

I-1-b-8 

—CH 2 —CHOC 4 H 9 —(CH 2 ) 3 —

I-1-b-9 

—CH 2 —CHOC 4 H 9 —(CH 2 ) 3 —

Cl—CH 2 —

I-1-b-10

—CH 2 —CHOC 4 H 9 —(CH 2 ) 3 —

I-1-b-11

—(CH 2 ) 2 —O—(CH 2 ) 2 —

H 3 C—O—CH 2 —

I-1-b-12

—(CH 2 ) 2 —O—(CH 2 ) 2 —

H 3 C—O—CH 2 —

I-1-b-13

—CH 2 —CHOC 4 H 9 —(CH 2 ) 3 —

i-C 3 H 7

I-1-b-14

i-C 3 H 7

CH 3

i-C 3 H 7

I-1-b-15

—CH 2 —CHOC 4 H 9 —(CH 2 ) 3 —

H 3 C—O—CH 2 —

I-1-b-16

—(CH 2 ) 5 —

H 3 C—O—CH 2 —

I-1-b-17

—(CH 2 ) 5 —

i-C 3 H 7

I-1-b-18

CH 3

CH 3

i-C 3 H 7

I-1-b-19

—(CH 2 ) 5 —

t-C 4 H 9

I-1-b-20

i-C 3 H 7

CH 3

H 3 C—O—CH 2 —

I-1-b-21

CH 3

CH 3

H 3 C—O—CH 2 —

I-1-b-22

i-C 3 H 7

CH 3

i-C 3 H 7

wherein

A, B, D, M R 2 , J, X and Y have the meanings given in the table:

Compound

J

X

Y

D

A

B

I-1-c-1 

4-I

2-CH 3

6-C 2 H 5

H

—(CH 2 ) 2 —CHOCH 3 —(CH 2 ) 2 —

I-1-c-2 

2-I

5-CH 3

H

H

—(CH 2 ) 2 —CHOCH 3 —(CH 2 ) 2 —

I-1-c-4 

2-I

5-CH 3

H

H

—(CH 2 ) 2 —CHOCH 3 —(CH 2 ) 2 —

I-1-c-5 

2-I

4-Cl

6-C 2 H 5

H

—(CH 2 ) 2 —O—(CH 2 ) 2 —

I-1-c-6 

2-I

4-Cl

6-C 2 H 5

H

—(CH 2 ) 2 —CHOCH 3 —(CH 2 ) 2 —

I-1-c-7 

3-I

6-CH 3

H

H

—(CH 2 ) 2 —CHOCH 3 —(CH 2 ) 2 —

I-1-c-8 

4-I

2-CH 3

6-CH 3

H

—(CH 2 ) 2 —CHOCH 3 —(CH 2 ) 2 —

I-1-c-10

4-I

2-C 2 H 5

6-CH 3

H

n-C 3 H 7

CH 3

I-1-c-11

4-I

2-C 2 H 5

6-CH 3

H

CH 3

I-1-c-12

4-I

2-C 2 H 5

6-CH 3

H

—(CH 2 ) 2 —O—(CH 2 ) 2 —

I-1-c-13

4-I

2-C 2 H 5

6-Cl

H

—(CH 2 ) 2 —O—(CH 2 ) 2 —

I-1-c-14

4-I

2-CH 3

6-CH 3

H

—CH 2 —CHOC 4 H 9 —(CH 2 ) 3 —

I-1-c-15

4-I

2-CH 3

6-CH 3

H

—CH 2 —CHOC 4 H 9 —(CH 2 ) 3 —

I-1-c-16

4-I

2-CH 3

6-CH 3

H

—CH 2 —CHOC 4 H 9 —(CH 2 ) 3 —

I-1-c-17

4-I

2-C 2 H 5

6-CH 3

H

—(CH 2 ) 5 —

I-1-c-18

4-I

2-C 2 H 5

6-CH 3

H

CH 3

CH 3

I-1-c-19

4-I

2-C 2 H 5

6-CH 3

H

i-C 4 H 9

CH 3

I-1-c-20

4-I

2-CH 3

6-CH 3

H

—(CH 2 ) 2 —O—(CH 2 ) 2 —

Compound

M

R 2

I-1-c-1 

O

C 2 H 5

I-1-c-2 

O

C 6 H 5 —CH 2 —

I-1-c-4 

O

C 2 H 5

I-1-c-5 

O

C 2 H 5

I-1-c-6 

O

C 2 H 5

I-1-c-7 

O

C 2 H 5

I-1-c-8 

O

C 2 H 5

I-1-c-10

O

C 2 H 5

I-1-c-11

O

C 2 H 5

I-1-c-12

O

C 2 H 5

I-1-c-13

O

C 2 H 5

I-1-c-14

O

C 6 H 5 —CH 2 —

I-1-c-15

O

CH 2 ═CH—CH 2 —

I-1-c-16

O

C 2 H 5

I-1-c-17

O

C 2 H 5

I-1-c-18

O

C 2 H 5

I-1-c-19

O

C 2 H 5

I-1-c-20

O

C 2 H 5 .

2. The compound of claim 1 , wherein the compound is I-1-a-3, I-1-a-8, I-1-a-12, I-1-a-13, I-1-a-18, I-1-a-19, I-1-a-20, I-1-b-3, I-1-b-16, I-1-c-12, or I-1-c-17.

3. A compound of the formula (I-1-c-3):

4. A pesticide composition and/or herbicide composition comprising

at least one compound of claim 1 and; an extender and/or a surfactant.

5. A method for controlling an animal pest and/or unwanted vegetation, comprising

contacting one or more compounds of claim 1 with the pest, the unwanted vegetation, and/or their habitats.

6. A process for preparing a pesticide composition or a herbicide composition, comprising

mixing one or more compounds of claim 1 with an extender and/or a surfactant.

7. A composition comprising,

(a′) at least one compound of claim 1 ,

and

(b′) at least one crop plant compatibility-improving compound;

wherein the crop plant compatibility-improving compound is at least one of:

4-dichloroacetyl-1-oxa-4-azaspiro[4.5]decane (AD-67, MON-4660),

1-dichloroacetylhexahydro-3,3,8a-trimethylpyrrolo[1,2-a]pyrimidin-6(2H)-one (dicyclonon, BAS-145138),

4-dichloroacetyl-3,4-dihydro-3-methyl-2H-1,4-benzoxazine (benoxacor),

1-methylhexyl 5-chloroquinoline-8-oxyacetate (cloquintocet-mexyl)

3-(2-chlorobenzyl)-1-(1-methyl-1-phenylethyl)urea (cumyluron),

α-(cyanomethoximino)phenylacetonitrile (cyometrinil),

2,4-dichlorophenoxyacetic acid (2,4-D),

4-(2,4-dichlorophenoxy)butyric acid (2,4-DB),

1-(1-methyl-1-phenylethyl)-3-(4-methylphenyl)urea (daimuron, dymron),

3,6-dichloro-2-methoxybenzoic acid (dicamba),

S-1-methyl-1-phenylethyl piperidine-1-thiocarboxylate (dimepiperate),

2,2-dichloro-N-(2-oxo-2-(2-propenylamino)ethyl)-N-(2-propenyl)acetamide (DKA-24),

2,2-dichloro-N,N-di-2-propenylacetamide (dichlormid),

4,6-dichloro-2-phenylpyrimidine (fenclorim),

ethyl 1-(2,4-dichlorophenyl)-5-trichloromethyl-1H-1,2,4-triazole-3-carboxylate (fenchlorazole-ethyl),

phenylmethyl 2-chloro-4-trifluoromethylthiazole-5-carboxylate (flurazole),

4-chloro-N-(1,3-dioxolan-2-ylmethoxy)-α-trifluoroacetophenone oxime (fluxofenim),

3-dichloroacetyl-5-(2-furanyl)-2,2-dimethyloxazolidine (furilazole, MON-13900),

ethyl 4,5-dihydro-5,5-diphenyl-3-isoxazolecarboxylate (isoxadifen-ethyl),

1-(ethoxycarbonyl)ethyl 3,6-dichloro-2-methoxybenzoate (lactidichlor),

(4-chloro-o-tolyloxy)acetic acid (MCPA),

2-(4-chloro-o-tolyloxy)propionic acid (mecoprop),

diethyl 1-(2,4-dichorophenyl)-4,5-dihydro-5-methyl-1H-pyrazole-3,5-dicarboxylate (mefenpyr-diethyl)

2-dichloromethyl-2-methyl-1,3-dioxolane (MG-191),

2-propenyl-1-oxa-4-azaspiro[4.5]decane-4-carbodithioate (MG-838),

1,8-naphthalic anhydride,

α-(1,3-dioxolan-2-ylmethoximino)phenylacetonitrile (oxabetrinil),

2,2-dichloro-N-(1,3-dioxolan-2-ylmethyl)-N-(2-propenyl)acetamide (PPG-1292),

3-dichloroacetyl-2,2-dimethyloxazolidine (R-28725),

3-dichloroacetyl-2,2,5-trimethyloxazolidine (R-29148),

4-(4-chloro-o-tolyl)butyric acid,

4-(4-chlorophenoxy)butyric acid,

diphenylmethoxyacetic acid,

methyl diphenylmethoxyacetate,

ethyl diphenylmethoxyacetate,

methyl 1-(2-chlorophenyl)-5-phenyl-1H-pyrazole-3-carboxylate,

ethyl 1-(2,4-dichlorophenyl)-5-methyl-1H-pyrazole-3-carboxylate,

ethyl 1-(2,4-dichlorophenyl)-5-isopropyl-1H-pyrazole-3-carboxylate,

ethyl 1-(2,4-dichlorophenyl)-5-(1,1-dimethylethyl)-1H-pyrazole-3-carboxy late,

ethyl 1-(2,4-dichlorophenyl)-5-phenyl-1H-pyrazole-3-carboxylate,

ethyl 5-(2,4-dichlorobenzyl)-2-isoxazoline-3-carboxylate,

ethyl 5-phenyl-2-isoxazoline-3-carboxylate,

ethyl 5-(4-fluorophenyl)-5-phenyl-2-isoxazoline-3-carboxylate,

1,3-dimethylbut-1-yl 5-chloroquinoline-8-oxyacetate,

4-allyloxybutyl 5-chloroquinoline-8-oxyacetate,

1-allyloxyprop-2-yl5-chloroquinoline-8-oxyacetate,

methyl 5-chloroquinoxaline-8-oxyacetate,

ethyl 5-chloroquinoline-8-oxyacetate,

allyl 5-chloroquinoxaline-8-oxyacetate,

2-oxoprop-1-yl5-chloroquinoline-8-oxyacetate,

diethyl 5-chloroquinoline-8-oxymalonate,

diallyl 5-chloroquinoxaline-8-oxymalonate,

diethyl 5-chloroquinoline-8-oxymalonate,

4-carboxychroman-4-ylacetic acid (AC-304415),

4-chlorophenoxyacetic acid,

3,3′-dimethyl-4-methoxybenzophenone,

1-bromo-4-chloromethylsulfonylbenzene,

1-[4-(N-2-methoxybenzoylsulfamoyl)phenyl]-3-methylurea (also known as N-(2-methoxybenzoyl)-4-[(methylaminocarbonyl)amino]benzenesulfonamide),

1-[4-(N-2-methoxybenzoylsulfamoyl)phenyl]-3,3-dimethylurea,

1-[4-(N-4,5-dimethylbenzoylsulfamoyl)phenyl]-3-methylurea,

1-[4-(N-naphthylsulfamoyl)phenyl]-3,3-dimethylurea,

N-(2-methoxy-5-methylbenzoyl)-4-(cyclopropylaminocarbonyl)benzenesulfonamide,

and/or one of the following compounds

of the general formula (IIa)

the general formula (IIb)

and/or of the general formula (IIc)

wherein

m is 0, 1, 2, 3, 4 or 5,

A 1 represents one of the divalent heterocyclic groupings shown below:

n is 0, 1, 2, 3, 4 or 5,

A 2 represents optionally C 1 -C 4 -alkyl- and/or C 1 -C 4 -alkoxy-carbonyl- and/or C 1 -C 4 -alkenyloxy-carbonyl-substituted alkanediyl having 1 or 2 carbon atoms,

R 14 represents hydroxyl, mercapto, amino, C 1 -C 6 -alkoxy, C 1 -C 6 -alkylthio, C 1 -C 6 -alkylamino or di(C 1 -C 4 -alkyl)-amino,

R 15 represents hydroxyl, mercapto, amino, C 1 -C 7 -alkoxy, C 1 -C 6 -alkenyloxy, C 1 -C 6 -alkenyloxy-C 1 -C 6 -alkoxy, C 1 -C 6 -alkylthio, C 1 -C 6 -alkylamino or di(C 1 -C 4 -alkyl)-amino,

R 16 represents in each case an optionally fluoro, chloro or bromo-substituted C 1 -C 4 -alkyl,

R 17 represents hydrogen, in each case an optionally fluoro, chloro or bromo-substituted C 1 -C 6 -alkyl, C 2 -C 6 -alkenyl or C 2 -C 6 -alkynyl, C 1 -C 4 -alkoxy-C 1 -C 4 -alkyl, dioxolanyl-C 1 -C 4 -alkyl, furyl, furyl-C 1 -C 4 -alkyl, thienyl, thiazolyl, piperidinyl, or an optionally fluoro, chloro or bromo- or C 1 -C 4 -alkyl-substituted phenyl,

R 18 represents hydrogen, in each case an fluoro, chloro or bromo-substituted C 1 -C 6 -alkyl, C 2 -C 6 -alkenyl or C 2 -C 6 -alkynyl, C 1 -C 4 -alkoxy-C 1 -C 4 -alkyl, dioxolanyl-C 1 -C 4 -alkyl, furyl, furyl-C 1 -C 4 -alkyl, thienyl, thiazolyl, piperidinyl, or an optionally fluoro, chloro or bromo- or C 1 -C 4 -alkyl-substituted phenyl,

R 17 and R 18 also together represent C 3 -C 6 -alkanediyl or C 2 -C 5 -oxaalkanediyl, each of which may be optionally substituted by C 1 -C 4 -alkyl, phenyl, furyl, a fused benzene ring or by two substituents which, together with the C atom to which they are attached, form a 5- or 6-membered carbocycle,

R 19 represents hydrogen, cyano, halogen, or represents in each case an optionally fluoro, chloro or bromo-substituted C 1 -C 4 -alkyl, C 3 -C 6 -cycloalkyl or phenyl,

R 20 represents hydrogen, in each case an optionally hydroxyl-, cyano-, halogen- or C 1 -C 4 -alkoxy-substituted C 3 -C 6 -cycloalkyl or tri-(C 1 -C 4 -alkyl)-silyl,

R 21 represents hydrogen, cyano, halogen, or represents in each case an optionally fluoro, chloro or bromo-substituted C 1 -C 4 -alkyl, C 3 -C 6 -cycloalkyl or phenyl,

X 1 represents nitro, cyano, halogen, C 1 -C 4 -alkyl, C 1 -C 4 -haloalkyl, C 1 -C 4 -alkoxy or C 1 -C 4 -haloalkoxy,

X 2 represents hydrogen, cyano, nitro, halogen, C 1 -C 4 -alkyl, C 1 -C 4 -haloalkyl, C 1 -C 4 -alkoxy or C 1 -C 4 -haloalkoxy,

X 3 represents hydrogen, cyano, nitro, halogen, C 1 -C 4 -alkyl, C 1 -C 4 -haloalkyl, C 1 -C 4 -alkoxy or C 1 -C 4 -haloalkoxy,

and/or the following compounds

of the general formula (IId)

or of the general formula (IIe)

wherein

t is 0, 1, 2, 3, 4 or 5,

v is 0, 1, 2, 3, 4 or 5,

R 22 represents hydrogen or C 1 -C 4 -alkyl,

R 23 represents hydrogen or C 1 -C 4 -alkyl,

R 24 represents hydrogen, in each case optionally cyano-, halogen- or C 1 -C 4 -alkoxy-substituted C 1 -C 6 -alkyl, C 1 -C 6 -alkoxy, C 1 -C 6 -alkylthio, C 1 -C 6 -alkylamino or di(C 1 -C 4 -alkyl)-amino, or in each case optionally cyano-, halogen- or C 1 -C 4 -alkyl-substituted C 3 -C 6 -cycloalkyl, C 3 -C 6 -cycloalkyloxy, C 3 -C 6 -cycloalkylthio or C 3 -C 6 -cycloalkylamino,

R 25 represents hydrogen, optionally cyano-, hydroxyl-, halogen- or C 1 -C 4 -alkoxy-substituted C 1 -C 6 -alkyl, in each case optionally cyano- or halogen-substituted C 3 -C 6 -alkenyl or C 3 -C 6 -alkynyl, or optionally cyano-, halogen- or C 1 -C 4 -alkyl-substituted C 3 -C 6 -cycloalkyl,

R 26 represents hydrogen, optionally cyano-, hydroxyl-, halogen- or C 1 -C 4 -alkoxy-substituted C 1 -C 6 -alkyl, in each case optionally cyano- or halogen-substituted C 3 -C 6 -alkenyl or C 3 -C 6 -alkynyl, optionally cyano-, halogen- or C 1 -C 4 -alkyl-substituted C 3 -C 6 -cycloalkyl, or optionally nitro-, cyano-, halogen-, C 1 -C 4 -alkyl-, C 1 -C 4 -haloalkyl-, C 1 -C 4 -alkoxy- or C 1 -C 4 -haloalkoxy-substituted phenyl, or together with R 25 represents in each case optionally C 1 -C 4 -alkyl-substituted C 2 -C 6 -alkanediyl or C 2 -C 5 -oxaalkanediyl,

X 4 represents nitro, cyano, carboxyl, carbamoyl, formyl, sulfamoyl, hydroxyl, amino, halogen, C 1 -C 4 -alkyl, C 1 -C 4 -haloalkyl, C 1 -C 4 -alkoxy or C 1 -C 4 -haloalkoxy, and

X 5 represents nitro, cyano, carboxyl, carbamoyl, formyl, sulfamoyl, hydroxyl, amino, halogen, C 1 -C 4 -alkyl, C 1 -C 4 -haloalkyl, C 1 -C 4 -alkoxy or C 1 -C 4 -haloalkoxy.

8. The composition as claimed in claim 7 , wherein the crop plant compatibility-improving compound comprises at least one of

cloquintocet-mexyl,

fenchlorazole-ethyl,

isoxadifen-ethyl,

mefenpyr-diethyl,

furilazole,

fenclorim,

cumyluron,

dymron,

compound IIe-5, or

compound IIe-11;

wherein the compounds IIe-5 or IIe-11 have the following formulae:

9. The composition of claim 7 , wherein the crop plant compatibility-improving compound is mefenpyr-diethyl.

10. A method for controlling unwanted vegetation, comprising contacting the composition of claim 7 with the vegetation or its habitat.

11. A method for controlling unwanted vegetation, comprising contacting a compound of claim 1 and a crop plant compatibility-improving compound, separately in close temporal succession, or as a mixture, with the unwanted vegetation or its habitat;

wherein the crop plant-compatibility-improving compound is at least one of:

4-dichloroacetyl-1-oxa-4-azaspiro[4.5]decane (AD-67, MON-4660),

1-dichloroacetylhexahydro-3,3,8a-trimethylpyrrolo[1,2-a]pyrimidin-6(2H)-one (dicyclonon, BAS-145138),

4-dichloroacetyl-3,4-dihydro-3-methyl-2H-1,4-benzoxazine (benoxacor),

1-methylhexyl 5-chloroquinoline-8-oxyacetate (cloquintocet-mexyl),

3-(2-chlorobenzyl)-1-(1-methyl-1-phenylethyl)urea (cumyluron),

α-(cyanomethoximino)phenylacetonitrile (cyometrinil),

2,4-dichlorophenoxyacetic acid (2,4-D),

4-(2,4-dichlorophenoxy)butyric acid (2,4-DB),

1-(1-methyl-1-phenylethyl)-3-(4-methylphenyl)urea (daimuron, dymron),

3,6-dichloro-2-methoxybenzoic acid (dicamba),

S-1-methyl-1-phenylethyl piperidine-1-thiocarboxylate (dimepiperate),

2,2-dichloro-N-(2-oxo-2-(2-propenylamino)ethyl)-N-(2-propenyl)acetamide (DKA-24),

2,2-dichloro-N,N-di-2-propenylacetamide (dichlormid),

4,6-dichloro-2-phenylpyrimidine (fenclorim),

ethyl 1-(2,4-dichlorophenyl)-5-trichloromethyl-1H-1,2,4-triazole-3-carboxylate (fenchlorazole-ethyl),

phenylmethyl 2-chloro-4-trifluoromethylthiazole-5-carboxylate (flurazole),

4-chloro-N-(1,3-dioxolan-2-ylmethoxy)-α-trifluoroacetophenone oxime (fluxofenim),

3-dichloroacetyl-5-(2-furanyl)-2,2-dimethyloxazolidine (furilazole, MON-13900),

ethyl 4,5-dihydro-5,5-diphenyl-3-isoxazolecarboxy late (isoxadifen-ethyl),

1-(ethoxycarbonyl)ethyl 3,6-dichloro-2-methoxybenzoate (lactidichlor),

(4-chloro-o-tolyloxy)acetic acid (MCPA),

2-(4-chloro-o-tolyloxy)propionic acid (mecoprop),

diethyl 1-(2,4-dichorophenyl)-4,5-dihydro-5-methyl-1H-pyrazole-3,5-dicarboxylate (mefenpyr-diethyl),

2-dichloromethyl-2-methyl-1,3-dioxolane (MG-191),

2-propenyl-1-oxa-4-azaspiro[4.5]decane-4-carbodithioate (MG-838),

1,8-naphthalic anhydride,

α-(1,3-dioxolan-2-ylmethoximino)phenylacetonitrile (oxabetrinil),

2,2-dichloro-N-(1,3-dioxolan-2-ylmethyl)-N-(2-propenyl)acetamide (PPG-1292),

3-dichloroacetyl-2,2-dimethyloxazolidine (R-28725),

3-dichloroacetyl-2,2,5-trimethyloxazolidine (R-29148),

4-(4-chloro-o-tolyl)butyric acid,

4-(4-chlorophenoxy)butyric acid,

diphenylmethoxyacetic acid,

methyl diphenylmethoxyacetate,

ethyl diphenylmethoxyacetate,

methyl 1-(2-chlorophenyl)-5-phenyl-1H-pyrazole-3-carboxylate,

ethyl 1-(2,4-dichlorophenyl)-5-methyl-1H-pyrazole-3-carboxylate,

ethyl 1-(2,4-dichlorophenyl)-5-isopropyl-1H-pyrazole-3-carboxylate,

ethyl 1-(2,4-dichlorophenyl)-5-(1,1-dimethylethyl)-1H-pyrazole-3-carboxylate,

ethyl 1-(2,4-dichlorophenyl)-5-phenyl-1H-pyrazole-3-carboxylate,

ethyl 5-(2,4-dichlorobenzyl)-2-isoxazoline-3-carboxylate,

ethyl 5-phenyl-2-isoxazoline-3-carboxylate,

ethyl 5-(4-fluorophenyl)-5-phenyl-2-isoxazoline-3-carboxylate,

1,3-dimethylbut-1-yl 5-chloroquinoline-8-oxyacetate,

4-allyloxybutyl 5-chloroquinoline-8-oxyacetate,

1-allyloxyprop-2-yl5-chloroquinoline-8-oxyacetate,

methyl 5-chloroquinoxaline-8-oxyacetate,

ethyl 5-chloroquinoline-8-oxyacetate,

allyl 5-chloroquinoxaline-8-oxyacetate,

2-oxoprop-1-yl 5-chloroquinoline-8-oxyacetate,

diethyl 5-chloroquinoline-8-oxymalonate,

diallyl 5-chloroquinoxaline-8-oxymalonate,

diethyl 5-chloroquinoline-8-oxymalonate,

4-carboxychroman-4-ylacetic acid (AC-304415),

4-chlorophenoxyacetic acid,

3,3′-dimethyl-4-methoxybenzophenone,

1-bromo-4-chloromethylsulfonylbenzene,

1-[4-(N-2-methoxybenzoylsulfamoyl)phenyl]-3-methylurea (also known as N-(2-methoxybenzoyl)-4-[(methylaminocarbonyl)amino]benzenesulfonamide),

1-[4-(N-2-methoxybenzoylsulfamoyl)phenyl]-3,3-dimethylurea,

1-[4-(N-4,5-dimethylbenzoylsulfamoyl)phenyl]-3-methylurea,

1-[4-(N-naphthylsulfamoyl)phenyl]-3,3-dimethylurea,

N-(2-methoxy-5-methylbenzoyl)-4-(cyclopropylaminocarbonyl)benzenesulfonamide,

and/or one of the following compounds

of the general formula (IIa)

the general formula (IIb)

and/or of the general formula (IIc)

wherein

m iso, 1, 2, 3, 4 or 5,

A 1 represents one of the divalent heterocyclic groupings shown below:

n is 0, 1, 2, 3, 4 or 5,

A 2 represents optionally C 1 -C 4 -alkyl- and/or C 1 -C 4 -alkoxy-carbonyl- and/or C 1 -C 4 -alkenyloxy-carbonyl-substituted alkanediyl having 1 or 2 carbon atoms,

R 14 represents hydroxyl, mercapto, amino, C 1 -C 6 -alkoxy, C 1 -C 6 -alkylthio, C 1 -C 6 -alkylamino or di(C 1 -C 4 -alkyl)-amino,

R 15 represents hydroxyl, mercapto, amino, C 1 -C 7 -alkoxy, C 1 -C 6 -alkenyloxy, C 1 -C 6 -alkenyloxy-C 1 -C 6 -alkoxy, C 1 -C 6 -alkylthio, C 1 -C 6 -alkylamino or di(C 1 -C 4 -alkyl)-amino,

R 16 represents in each case an optionally fluoro, chloro or bromo-substituted C 1 -C 4 -alkyl,

R 17 represents hydrogen, in each case an optionally fluoro, chloro or bromo-substituted C 1 -C 6 -alkyl, C 2 -C 6 -alkenyl or C 2 -C 6 -alkynyl, C 1 -C 4 -alkoxy-C 1 -C 4 -alkyl, dioxolanyl-C 1 -C 4 -alkyl, furyl, furyl-C 1 -C 4 -alkyl, thienyl, thiazolyl, piperidinyl, or an optionally fluoro, chloro or bromo- or C 1 -C 4 -alkyl-substituted phenyl,

R 18 represents hydrogen, in each case an optionally fluoro, chloro or bromo-substituted C 1 -C 6 -alkyl, C 2 -C 6 -alkenyl or C 2 -C 6 -alkynyl, C 1 -C 4 -alkoxy-C 1 -C 4 -alkyl, dioxolanyl-C 1 -C 4 -alkyl, furyl, furyl-C 1 -C 4 -alkyl, thienyl, thiazolyl, piperidinyl, or an optionally fluoro, chloro or bromo- or C 1 -C 4 -alkyl-substituted phenyl,

R 17 and R 18 also together represent C 3 -C 6 -alkanediyl or C 2 -C 5 -oxaalkanediyl, each of which may be optionally substituted by C 1 -C 4 -alkyl, phenyl, furyl, a fused benzene ring or by two substituents which, together with the C atom to which they are attached, form a 5- or 6-membered carbocycle,

R 19 represents hydrogen, cyano, halogen, or represents in each case an optionally fluoro, chloro or bromo-substituted C 1 -C 4 -alkyl, C 3 -C 6 -cycloalkyl or phenyl,

R 20 represents hydrogen, in each case an optionally hydroxyl-, cyano-, halogen- or C 1 -C 4 -alkoxy-substituted C 1 -C 6 -alkyl, C 3 -C 6 -cycloalkyl or tri-(C 1 -C 4 -alkyl)-silyl,

R 21 represents hydrogen, cyano, halogen, or represents in each case an optionally fluoro, chloro or bromo-substituted C 1 -C 4 -alkyl, C 3 -C 6 -cycloalkyl or phenyl,

X 1 represents nitro, cyano, halogen, C 1 -C 4 -alkyl, C 1 -C 4 -haloalkyl, C 1 -C 4 -alkoxy or C 1 -C 4 -haloalkoxy,

X 2 represents hydrogen, cyano, nitro, halogen, C 1 -C 4 -alkyl, C 1 -C 4 -haloalkyl, C1-C 4 -alkoxy or C 1 -C 4 -haloalkoxy,

X 3 represents hydrogen, cyano, nitro, halogen, C 1 -C 4 -alkyl, C 1 -C 4 -haloalkyl, C 1 -C 4 -alkoxy or C 1 -C 4 -haloalkoxy,

and/or the following compounds,

of the general formula (IId)

or of the general formula (IIe)

wherein

t is 0, 1, 2, 3, 4 or 5,

v is 0, 1, 2, 3, 4 or 5,

R 22 represents hydrogen or C 1 -C 4 -alkyl,

R 23 represents hydrogen or C 1 -C 4 -alkyl,

R 24 represents hydrogen, in each case optionally cyano-, halogen- or C 1 -C 4 -alkoxy-substituted C 1 -C 6 -alkyl, C 1 -C 6 -alkoxy, C 1 -C 6 -alkylthio, C 1 -C 6 -alkylamino or di(C 1 -C 4 -alkyl)-amino, or in each case optionally cyano-, halogen- or C 1 -C 4 -alkyl-substituted C 3 -C 6 -cycloalkyl, C 3 -C 6 -cycloalkyloxy, C 3 -C 6 -cycloalkylthio or C 3 -C 6 -cycloalkylamino,

R 25 represents hydrogen, optionally cyano-, hydroxyl-, halogen- or C 1 -C 4 -alkoxy-substituted C 1 -C 6 -alkyl, in each case optionally cyano- or halogen-substituted C 3 -C 6 -alkenyl or C 3 -C 6 -alkynyl, or optionally cyano-, halogen- or C 1 -C 4 -alkyl-substituted C 3 -C 6 -cycloalkyl,

R 26 represents hydrogen, optionally cyano-, hydroxyl-, halogen- or C 1 -C 4 -alkoxy-substituted C 1 -C 6 -alkyl, in each case optionally cyano- or halogen-substituted C 3 -C 6 -alkenyl or C 3 -C 6 -alkynyl, optionally cyano-, halogen- or C 1 -C 4 -alkyl-substituted C 3 -C 6 -cycloalkyl, or optionally nitro-, cyano-, halogen-, C 1 -C 4 -alkyl-, C 1 -C 4 -haloalkyl-, C 1 -C 4 -alkoxy- or C 1 -C 4 -haloalkoxy-substituted phenyl, or together with R 25 represents in each case optionally C 1 -C 4 -alkyl-substituted C 2 -C 6 -alkanediyl or C 2 -C 5 -oxaalkanediyl,

X 4 represents nitro, cyano, carboxyl, carbamoyl, formyl, sulfamoyl, hydroxyl, amino, halogen, C 1 -C 4 -alkyl, C 1 -C 4 -haloalkyl, C 1 -C 4 -alkoxy or C 1 -C 4 -haloalkoxy, and

X 5 represents nitro, cyano, carboxyl, carbamoyl, formyl, sulfamoyl, hydroxyl, amino, halogen, C 1 -C 4 -alkyl, C 1 -C 4 -haloalkyl, C 1 -C 4 -alkoxy or C 1 -C 4 -haloalkoxy.

Assignments (2)
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Feb 20, 2015
From: BAYER CROPSCIENCE AG
To: BAYER INTELLECTUAL PROPERTY GMBH
Reel/Frame 034991/0036 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded May 18, 2009
From: FISCHER, REINER; BRETSCHNEIDER, THOMAS; ILG, KERSTIN; LEHR, STEFAN; FEUCHT, DIETER; MALSAM, OLGA; RECKMANN, UDO; BOJACK, GUIDO; ARNOLD, CHRISTIAN; AULER, THOMAS; HILLS, MARTIN JEFFREY; KEHNE, HEINZ; HEMPEL, WALTRAUD; SANWALD, ERICH
To: BAYER CROPSCIENCE AG
Reel/Frame 022696/0525 →