AU611191B2

AU611191B2 - Herbicidal sulfonamides

Info

Publication number: AU611191B2
Application number: AU21334/88A
Authority: AU
Inventors: Morris Padgett Rorer
Original assignee: EI Du Pont de Nemours and Co
Current assignee: EIDP Inc
Priority date: 1987-07-27
Filing date: 1988-07-25
Publication date: 1991-06-06
Anticipated expiration: 2008-07-25
Also published as: AU2133488A

Description

aT--in 1 AU-Al-21334/88 WORLD INTELLECTUAL PROPERTY ORGANIZATION International Bureau

PCT

INTERNATIONAL APPLICATION PUBLISHED UNDER THE PATENT COOPERATION TREATY (PCT) (51) International Patent Classification 4 C07D 239/46, 239/52, 239/42 C07D 251/16, 251/46, 251/52 C07D 401/12, 409/12, 403/12 A01N 47/36 (11) International Publication Number: WO 89/ 00991 t nIinatio u Pu ati ate:9 February 1989 (09.02.89) (21) International Application Number: PCT/U,,3S/02459 (22) International Filing Date: (31) Priority Application Number: (32) Priority Date: (33) Priority Country: (71) Applicant: E.I. DU PONT COMPANY [US/US]; 1007 ton, DE 19898 (US).

25 July 1988 (25.(7.88) 078,191 27 July 1987 (27.07.87)

US

DE NEMOURS AND Market Street, Wilming- (81) Designated States: AT (European patent), AU, BE (European patent), CH (European patent), DE (European patent), FR (European patent), GB (European patent), IT (European patent), JP, LU (European patent), NL (European patent), SE (European patent).

Published With international search report.

A.q.jP. 20 APR 1989

AUSTRALIAN

-1 MAR 1989 PATENT OFFICE (72) Inventor: RORER, Morris, Padgett 64 Lower Valley Lane, Newark, DE 19711 (US).

(74) Agent: COSTELLO, James, E.I, du Pont de Nemours and Company, Legal Department, 1007 Market Street, Wilmington, DE 19898 (US).

(54) Title: HERBICIDAL SULFONAMIDES

W

JSO

2 NHCNA I

R

(57) Abstract Heibicidal sulfonamides having general formula wherein J, W, R and A are more particularly described herein, Scompounds and agricultural compositions containing them being useful as preem-rgent or posternergent herbicides )th, or as plant growth regulants, including the manner of their use.

I- r L Ll.iL _C1 i i c- -L iY 1 WO 89/00991 -PCT/US88/02459 1

TITLE

HERBICIDAL SULFONAMIDES CROSS-REFERENCE TO RELATED APPLICATION This is a continuation-in-part of the application bearing United States Serial No. 078,191 filed on July 27, 1987.

BACKGROUND OF THE INVENTION The following publications disclose herbicidal sulfonylureas related to the sulfonamides of this invention in that substantially all disclosed compounds contain the characteristic sulfonylurea moiety. There are sufficient distinctions, however, to render these representative publications more useful as a backdrop against which to appreciate the instant invention rather than as suggestive of it.

U.S. 4,370,480 EP-A-79,772 U.S. 4,435,206 EP-A-87,780 U.S. 4,481,029 EP-A-95,925 U.S. 4,549,898 EP-A-126,711 U.S. 4,618,363 EP-A-203,825 U.S. 4,638,004 EP-A-245,058 U.S. 4,659,366 SA 85/2603 SA 83/3850.

SUMMARY OF THE INVENTION This invention pertains to compounds of Formula I, including their agriculturally suitable salts, herbicidal compositions containing said compounds and use thereof as preemergent herbicides, WO 89/00991 PCT/US88/02459 2 postemergent herbicides and/or plant growth regulants. For the sake of brevity, the compounds will be described and claimed with respect to Formula I, it being understood that all salts are included as well. The compounds are:

W

JSO

2

NHCNA

R

wherein J is selected from I LO 5- S S-2 6 J J J3.

1 CH2 1 R 2 4 R2 ,1 (0) JL-4 J- ,Tf WO 89/00991 WO 8900991PCT/US88/02459 (0)n Q N"'O pL~ Q2 R2

N

3 R-u and R3 E is a single bond or -H-

Q

1 is -C(Tl)-N-O-Alk; WO 89/00991 pCT/US88/02459 4 TI is selected from CN, F, Cl, Br, SCN, N~p C 1 to C 2 alkoxy, C 1 to C 2 thioalkyl, NH(C 1 to C 2 alkyl), N(C 1 to C 2 alkyl) 2

N(OCH

3

)CH

3 and 1j~H2)3 or 4; Alk is selected from C 1 to C 3 alkyl, optionally gubstituted with CN, OCH 3

SCH

3 or halogen; 110 and CH 2

CH-CH

2

W

2 is -C(T, 2

T

2 is selected from H; C 1 to C 3 alkyl optionally substituted with CN, OCH 3 r SCH 3 or halogen; cyclopropyl; F; Cl; Br; CN; SCN; N3; C 1 to C 2 alkoxy- C 1 to C 2 thioalkyl; NH(C 1 to C 2 alkyl); N(C 1 to C 2 alkyl) 2

N(OCH

3

)CH

3 and d(H2)3 or 4; Ri is selected from H, C 1 to C 3 alkyl, C1 to C 3 haloalkyl, halogen, CN, nitro, C1 to C 3 alkoxy, C 1 to C 3 haloalkoxy, C 1 to C 3 alkylthio, CI to C 3 alkylsulfinyl, C 1 to C 3 alkylsulfonyl, SCF 2 H, NH 2

NHCH

3

N(CH

3 2 or CI to C 2 alkyl substituted with one C 1 to C 2 alkoxy, C 1 to C 2 halalkoxy, SI, SCH 3 CN o

OH;

R4 is selected from H, F, Cl, Br, C 1 to C 2 alkyl, C 1 to C 2 haloalkyl or C 1 to C 2 alkoxy;

R

3 is selected from H, C 1 to C 3 alkyl, CI to C 2 haloalkyl, C 3 to C 4 alkenyl, C 3 to C 4 alkynyl,

CH

2 CN, phenyl and phenyl substituted by F, Cl, CH3 Or OCH 3 n is 0 or 1; R is H or CH, 3 W is Q or S,; L WO 89/00991 CUS8029 PCT/US88/02459 A is selected from x N1

A--Z

.N/x2

OCH

3 and

A

WO 89/00991 PCT/US88/02459 6 X is selected from H, C 1 to C, 4 alkyl, C 1 to C 4 alkoxy, C 1 to C 4 haloalkoxye

C

1 to C 4 haloalkyl, C 1 to C 4 haloalkyithio,

C

1 to C 4 alkylthio, halogen, C 2 to C 5 alkoxyalkyl, C 2 to C 5 alkoxyalkoxy, amino, C 1 to C 3 alkylarilno, di(C 1 to C 3 alkyl)amino or C 3 to

C

5 cycloalkyl; Y is selected from C 1 to C 4 alkyl, C 1 to C 4 alkoxy, C 1 to C 4 haloal~oxy, C 1 to C 4 haloalkylthilo,

C

1 to C 4 aikylthic, C 2 to C alkoxyalkyl, C 2 to C 5 alkoxy-alkoxy, amino, C 1 to C 3 alkylamino, di(C 1 to C 3 alkyl)amino, C~ 3 to C 4 alkenyloxy, C 3 to C 4 alkynyloxy, C 2 to

C

5 -Ikylthioalkyl, C 1 to C 4 haloalkyl, C 2 to

C

4 alkynyl, azido, cyano, C 2 to C alkylsulfinylalkyl,

C

2 to C alkylsulfonylalkyl, 120 0L L CH 3

CI-

2 1H R b CH 2 ~e C I

CR'

'L R /rn R a2 'c RP 2 L2 and N(QCH 3 )CHi 3 m is 2 or 3; Land L2 are independently 0 or SI,

R

8 is HI or C 1 to C 3 alkyl; Rb and Rc are independently C 1 to C 3 akl Z is Cl- or N; ZIis CH or N;*

Y

1 l is 0 or CH- 2 X! is C" 3 QCl1 0C 2

H

5 Or QCF 2

H-;

XZ i Cf 3 2

U

5 or CII 2

CF

3 Yis QCH 3 0C 2 1i 5

SCH

3

SC

2 11 5 C11 3 or CEI 2 "31; WO 89/0099 1 PCT/US88/02459 7

X

3 is CH 3 or OC Y3is H or CM 3

X

4 is C11 3

OCH-

3 0C 2

H

5

CH

2 0CH 3 or Cl; and

Y

4 is CM 3

OCH

3 0C 2

H

5 or Cl; provided that i) when X is Cl, F, Br or I, then Z is CH and Y is OCH 3 0C 2

H

5

N(OC-

3

)CH

3

NHCH

3

N(CH

3 2 or OCF 2

H;

ii) when X or Y is C 1 haloalkoxy, then Z is

CHI

iii) X 4 and Y 4 are not simultaneously Cl; iv) when W is S, then R is H, A is A-i and Y is CM 3 0CM 3 0C 2

H

5

CH-

2

OCH

3

C

2

H

5

CF

3

SCM

3

OCH

2

CH-CH

2

OCHM

2 CE=CH, OCH 2

CH

2 CH1

CH(OCH

3 2 or l,3-dioxolan-2-yl; v) when the total number of oarbons of X and Y is greater than four, the number of carbon atoms of Q (or Q ais less than or equal to four; Vi) when J is J-6, J-7, 3-8 or J-9, and A is A-7, then Zis CH,; and vii) when J is 3-6, 3-7, J-8 or JP-9, and A is A-1, and X and Y ara haloolkoxy or haloalkylthiQI then T2 Is Cl, Br, CN, SCN, N 3

C

1 to C 2

C

1 to C 2 thioalkyl, NH(Cl to C 2 alkyl), N(C 1 to C 2 alkyl) 2 1 N(OCH3)CH 3 Or tH23or 4, In the above definitions, the term, Ialkyl"!, used either alone or in compound wora- such as 9 lalkylthiot or "haloalkyl," denotes straight chain or branched alkyl, such as methyl, ethyl, n-propyl, I'sopropyl or the different butyl and pentyl isomers.

j I.

11-Z /2 WO 89/00991 PCT/US88/02459 Alkoxy denotes methoxy, etho~ry, n-propyloxy, isopropyloxy and the different butyl isomers.

Alkeny. denotes straight chain or branched alkenes, such as 1-propenyl, 2-propenyl, 3-propenyl and the different butenyl and pentenyl, isomers.

Alk ynyl denotes straight chain or branched alkynes, such as ethynyl, 1-propynyl, 2-propynyl and the different butynyl and pentynyl isomers.

Alkylsulfonyl denotes methylrulfonyl, ethylsulfonyl and the different propylsulfonyl isomers.

Preferred Compounds A are compounds of Formula I wherein: E is a single bond; and W is 0.

Preferr~ed Compounds B are compounds of FormulaI whereini E is C14 2 or J is J-6; and W is5 0.

Preferred Compounds C are compounds A wherein,, RI is selected from H, F, Cl, Br, CH 2 CN, CH 3

OCH

3

SCH-

3 or OCF 2

H;

R

2 is selected from H, F C1, Br or CH 3

R~

3 is selected from H, C: to C 3 alkyl, phenyl, CH 2

CF

3 arid CH 2

'ZH=CH

7 X is selected from C 1 to C 2 alkylt C 1 to C 2 alkoxy, Cl, F, Br, I, OCF 2 H, CH 2 F, CF 3

QCH

2

CH

2 F, OCH 2

CHF

2

OCH

2

CF

3 I CH 2 Cl and

CH

2 Br; Y is selected from H, C 1 to C2 alkyl, Cl to Calkoxy, CH OCH 3

CH

2 0CCH NC 3 1

N(OCH

3

)CH

3 N1(CH 3 2

CF

3 SOCl 3 O1 2 0H=CH 2

OH

2 C-=CH, O0H 2

CH

2 00H 3

C

2 aikyl), N(Cl to C 2 aikyi) 2

N(OCR'

3

)CH

3 and N(CH 2 3 or 4; /3 I W7~ '4 PCT/US8Sf 02459 WO 89/00991 CH SCH 3 CRa 1~ b I ~R a2 c

H

R a 2 ICH 3 CR 4 OCF 2 H, OCF 2Br, SF2H cyciopropyl, CECH or C:ECCH 3 and Rb and Rc are C 1 to C 2 alkyl.

Preferred Compounds D are compounds C wherein: A is A-1; n is 0; X is selected from CH 3

OCH

3

OCH

2

CH

3 Cl or OCF Hi and Y is selected from CH 3

OCH

3

C

2

H

5

CH

2

OCH

3

NHCH

3 t CH(0"H 3 2 and cyclopropyl.

Preferred Compounds E are compounds D wherein: R is H; Ti is uelected from CN, C1 and C 1 to C 2 aikoXy; and

T

2 is selected from H, Ci to C 3 alkyl, cyclopropyl, Ci, CN and Ci to C 2 alkoxy.

Other preferred compounds are Compounds E wherein: J is J-i to J-5 and J-7 to J-13.

Y

Y 0- WO 89/00991 PCT/US88/02459 Specifically pret;.rred compounds are: 2-[[[[(4-cnlorcN-6-metlicxx-2-pyrimidinyl amino] carbonyl] amino sulfony j-N-methoxybenzenecarboxinaldoyl chloride, Compound 28, 2-[(cyano)(methoxyimixio)methyl methoc-y--6-methylr-2-py'rimidinyl) amino] c:13onyllbenzenesul(donamide, Compound 2, and N-methoxy-2-[[ [(4-methoxy-6-methyl-, triazin-2-yl)minolcarbonyaminolsulfonyl]benzenecarboximidoyl chloride, Compound 29.

DETAILS OF CTHE INVENTION Compounds of Formula I are prepared by the methods shown belowt in Equations 1, 2, 3 and 4, wherein J, W, A and R are as previously defined.

nehod of choice for thie individual compounds of Formula I will be readily apparent to those skillet in the art.

Equation 1 illustrates the reaction ot skilfonamides II with the phenol ester of tho appropriate carbamic acid or thiocarbamic aoid of Formula III in the presence of a tertiarlr amine base such as 1,8-diazabicytlo[5.40]undec-7-ene (DBU).

Similar coupling methoCis are described in EPA -0,804, Equation 1 J-S0 2

NH

2 PhQCNR-A bT-H3 7 ,L Rb

L

1

CH

3

CH

2 OH, CR a H2 a a 2 R WO 89/00991 PCT/US88/02459 11 The reaction of Equation 1 is best carried out at about to 25°C is an inert solvent such as dioxane or acetonitrile for 1 to 24 hours, optionally under an inert atmosphere and in the presence of an equimolar quantity of DBU. The desired products of Formula I can be conveniently isolated by acidifying the reaction solution with aqueous hydrochloric acid or acetic acid and filtration. Alternatively, the aqueous layer can be extracted with a solvent such as methylene chloride. Drying and evaporating the solvent affords the desired product.

The phenylcarbamate and phenylthiocarbamate intermediates of Formula III can be prepared by methods, or obvious modifications thereof, described in South African Patent Application 82/5671 and South African Patent App.lication 82/5045.

Equation 2 illustrates the reaction of sulfonylisocyanates and sulfonylisothiocyanates of Formula IV with the appropriate heterocyclic amines of Formula V.

EquatiLon 2

J-SO

2 NCW HNR-A I IV V The reaction of Equation 2 is best carried out in an inert solvent such as methylene chloride, tetrahydrofuran, toluene or acetonitrile at a temperature between about 0° and 80 0 C. A catalytic amount of 1,4-diazabicyclo[2.-1.2]octane (DABCO) can be used to accelerate the reaction. In cases where the products are insoluble in the reaction solvent, they can be isolated by simple filtration. Soluble -i st ~L i A-i, and X and Y are haloalkoxy or haloalkylthio, then T 2 is F, Cl, Br, CN, SCN, N 3

C

1 to C 2 alkoxy,

C

1 to C 2 thioalkyl,

NH(C

1 to C 2 alkyl),

N(C

1 to C 2 alkyl) 2

N(OCH

3

)CH

3 or N(CH) 3 or 3 or 4 WO 89/00991 PCT/US88/02459 12 products can be isolated by evaporation of the solvent and trituration of the residue with solvents such as 1-chlorobutane, diethyl ether or ethyl acetate, and filtration.

Sulfonyl isocyanates IV can be prepared directly from the corresponding sulfonamides II according to the procedures described in Ulrich et al., Newer Methods of Preparative Organic Chemistry, Vol. VI, page 223 to 241, Academic Press, New York and London, W. Foerst Ed. By this two-step procedure, sulfonamides are converted to isolatable n-butylsulfonylureas which are reacted further with phosgene and a tertiary amine catalyst to form sulfonyl isocyanates. The analogous one-step procedure can be employed by using the method described in U.S. Patent 4,238,621. Alternatively,' sulfonamides can be reacted with thionyl chloride to form intermediate N-sulfinylsulfonamides, which upon exposure to phosgene in the presence of a catalytic amount of pyridine, provide sulfcyl isocyanates. For additional details, see Ulrich et al., J. Orq. Chem., 3A, pages 3200 to 3202 (1969).

Sulfonyl isothiocyanates (iv, w=s) are prepared from the corresponding sulfonamides by reaction with carbon disulfide and potassium hydroxide followed by treatment of the resulting dipotassium salt with phosgene. Such a procedure is described in Arch. Pharm,, 299, 174 (1966).

Equation 3 illustrates the reaction of a sulfonyl carbamate or thiocarbamate of Formula VI with an appropriate heterocyclic amine V.

IC w :Ii WO 89/00991 PCT/US88/02459 Eguation 3

J-SO

2

NHCOC

6

H

5 HNR-A YI V The reaction of Equation 3 is carried out at about 200 to 100 0 C in an inert solvent such as p-dioxane for 0.5 to 24 hours. Additional details concerning the general coupling reaction to prepare sulfonylureas can be found in EPA 44,807. The product is isolated by evaporation of the reaction solvent and purified by trituration of the residue with solvents such as 1-chlorobutane or ethyl ether, and filtration, or by chromatography procedures on silica gel.

Phenylcarbamates and phenylthiocarbamates of Formula VI are prepared by methods described, or obvious modifications thereof, in U.S. Patent 4,443,243, EPA 44,808 or South African Patent Application 82/5042.

Equation 4 illustrates the reaction of sulfonamides of Formula Ia with appropriate salts or amines to form corresponding sulfonamides of Formula Ib.

NOAlk NOAlk

C-CI

R

p M-Ta RC-Tc or H-Tb

P

(57) Abstract Herbicidal sulfonamides having general formula wherein J, W, R and A are more particularly described herein, compounds and agricultural compositions containing them being useful as preem-rgent or postemergent herbicides )th, or as plant growth regulants, including the manner of their use.

WO 89/00991 PCT/US88/02459 14 wherein

O

P is SO 2

NHCNR-A;

A, Alk, R and R 1 are as previously defined; M is Na or K Ta is CN, SCN, N 3

C

1 to C 3 alkoxy, C to C 2 thioalkyl, or F; Tb is NH(C 1 to C 2 alkyl),

N(C

1 to C 2 alkyl) 2

N(OCH

3

)CH

3 or H 2 3 or 4; and Tc is Ta or Tb.

The reaction of Equation 4 is effected by reacting Ia with at least one molar equivalent of salt M-Ta (at least two molar equivalents when Ta is an alkoxide or mercaptide) in an inert solvent such as acetone, methyl ethyl ketone, tetrahydrofuran, dioxane, methanol, dimethylformamide (DMF), dimethylsulfone or dimethylsulfoxide. The reaction is carried out at about 200 to 140 0 C for 1 to 24 hours, and optionally in the presence of a phase transfer catalyst such as a crown ether. Products Ib (Tc is Ta) are isolated by addition of water, acidification if Ta is alkoxide or mercaptide, and filtration.

Alternatively, the aqueous suspension is extracted with a solvent such as methylene chloride, dried and the solvent evaporated to yield crude Ib. Product Ib b can be purified further by trituration with a solvent such as 1-chlorobutane, ethyl acetate or diethyl ether, and filtration, or by chromatography procedures on silica gel. Similarly, products Ib (Tc is Tb) can be prepared by reacting la with amines, H-Tb,

I

WO 89/0 191 PCT/US88/02459 preferably an excess of about 2 to 20 mole equivalents, in an inert solvent such as tetrahydrofuran, p-dioxane, methanol, methylene chloride or DMF. The reactions are carried out at about 0 C to 100 0 C for 1 to 24 hours. Work-up is as described above.

In anlogous manner, other compounds of Formula I can be prepared using procedures described in Equation 4, from appropriate corresponding compounds of Formula I, wherein J is J 2 to J 13 and Q 1 or Q 2 is C(Cl)=NOAlk.

As illustrated in Equation 5, the intermediate sulfonamides of Formula II are conveniently prepared by amination of the corresponding sulfonyl chlorides with anhydrous ammonia or aqueous ammonium hydroxide by general methods known in the art, Crossley et al., J. Am. Chem. Soc., eQ, pages 2223 to 2224 (1938); Pailer, Monatsh, 92, pages 677 to 683 (1961); and U.S.

Patent 4,511,392.

EQuation it

NH

J-SO

2 Cl or NH 4 0H J-SO 2

NH

2 VII II As illustrated in Equation 6, sulfonamides of Formula II can also be prepared by deprotection of t-butylsulfonamides of Formula VIII.

L_

WO 89/00991 PCT/US88/02459 16 Equation 6 TFA, PPA

J-SO

2

NH-C(CH

3 3 or p-TSA J-SO 2

NH

2 VIII. II The reaction of Equation 6 is conveniently carried out in excess trifluoroacetic acid (TFA) according to the procedure of Catt et al., J. Ora. Qhem 31, pages 566 to 568 (1974), or with polyphosphoric acid (PPA) according to procedures of Lomardino, J. Orq. Chem., 36, pages 1843 to 1845 (1971). Alternatively, i-butylsulfonamide VIII can be treated with a catalytic amount of p-toluene sulfonic acid (p.-TSA) in a solvent such as toluene or xylenes at reflux temperatures for 1 to 24 hours to yield II: Intermediate sulfonyl chlorides of SFormula VIIa are preferably prepared by oxidative-chlorination of an appropriate thioether of Formula IX, as shown below in Equation 7.

Equation 7 Cl2, H 2 0 2

J-SR

4

CH

3 CO2H or CH 3

CH

2 COZH J-SO 2 Cl IX vila wherein J is as previously defined, E is a single bond, and R 4 is C 2 to C 3 alkyl or benzyl.

Li I 1111 1 WO 89/00991 PCT/US88/02459 17 The reaction of Equation 7 is carried out by contacting a suspension of thioether IX in a solvent such as acetic or propionic acid in the presence of at least 2.5 equivalents of water and 3.0 equivalents of chlorine at about -200 to 30°C for 0.2 to 5 hours.

The reaction mixture is poured into ice-water and the product is isolated by filtration or extraction with a solvent such as methylene chloride. The extraction product is optionally washed with aqueous sodium bicarbonate until neutral or slightly basic to litmus, then dried, and the solvent is evaporated to yield a product sufficiently pure to be carried directly on to the next step.

Alternatively, reaction of thioether IX, wherein R 4 is benzyl or hydrogen, with a hypoch'orite solution, NaOC1, can provide sulfonyl chloride VIIa. For additional details, see analogous reactions in South African Patent Application No. 84/8845 and 84/8844. Mercaptans or thioethers can also be transformed to sulfonyl fluorides by reaction with chlorine and potassium hydrogen difluoride, which on further reaction with ammonia or ammonium hydroxide can provide sulfonamides; see, Brown et al., J.

Chem. Soc. Perkins Trans I, pages 522 to 527 (1972).

Sulfonyl chlorides, VIIa, can also be prepared by diazotization reactions, as illustrated in Equation 8.

Equation 8 1)alkylnitrite

J-NH

3 +Cl" 2) SO 2 CuC12 J-SO 2

C

1 X Vila N .L .J VL 1

I

WO 89/00991 PCT/US88/02459 18 The amine hydrochloride salt is diazotized with an alkylnitrite in an organic solvent, such as acetonitrile or acetone, and the resulting diazonium salt is reacted with sulfur dioxide and cupric chloride to yield Vila. Doyle, J. Org. Chem., 42, pages 2426 to 2431 (1977) and ibid, pages 2431 to 2436, describe conditions for analogous reactions.

Alternatively, sulfonyl chlorides Vila can be prepared by aqueous diazotization; for additional details, see EPA 83,975 and 85,476. Aromatic amines of Formual X can be prepared from the corresponding nitro compounds by various known reduction procedures, e.g., Preparative Organic Chemistry, 4 Ed., pages 557 to 563, John Wiley and Sons, New York and London, Hilgctag et al., Eds., and EPA 207,894.

Sulfonyl chlorides of Formula VIIb can be prepared from compounds of Formula XI as shown in Equation 9 and described in U.S, Patent 4,420,325.

Equation 9 1) rxl

J-CH

3 2) thioursa J-CH 2

SO

2 Cl 3) C1 2

H

2 0

VI

whetein J is as previously defined and [X3 is a suitable halogenating agent, such as N-bromosuccinimide.

Thioethers of Formula IX are important intermediates for preparing compounds of this invention and can be prepared by a variety of general WO 89/00991 WO 8900991PCT/US88/02459 1.9 methods known in the art. Several such procedures are described below in Equations 10 through Equation 10 illustrates the preparation of thioethers of Formula IXa, containing an alpha-chlorooxime moiety, from carboxylic acids of Formula XII. Subsequent reaction of IXa with appropriate salts, 14-Ta, or aminee, H-Tb, provides thioethers of Formula IXb.

E Tu at i.

CO

2

H

R T a l'R4 14-Ta b) IXa or H-Tb 1) S~d,,NOAlk 2) Hj 2 NOAlk lBr Rr~ 1IXa KOAIk R C-Tc SR 4 wherein Rlj R 4 o Alk, M4, Ta, Tb and Tc are as previously defined; and [XI is as defined below., in Equation i~a, carboxylic acids X11 are converted to acid chloride64 which in turn are converted to isolatable N-alkoxyamides by known subsequent reaction of the amides with suitable halogenating agents, [XI, provides compounds of '7ormula IXa. Suitable halogenating agents include phosphorous, pentachloride or phosphorous pentabrornide WO 89/0099 1 PCT/US88/02459 in an inert solvent such as benzene or chloroform at about 50 to 40 0 C for 1 to 24 hours; or phosgene, preferably, or thionyl chloride and a catalytic amount of DMF in an inert solvent such as methylene chloride, benzene or chlorobenzene at about 100 to 1300C for to 24 hours; or more preferably equimoJ,ar amounts of triphenylphosphine and carbon tetrachloride (or carbon tetrabromide) in an inert solvent such as acetonitrile at about 0 0 C to 80 0 C for 1 to 24 hours. Compounds of Formula IXa are isolated by evaporation of reaction media under vacuum and can be purified by optionally treatment with water followed by chromatography procedures on silica gel.

The reactions of EZquation l0b are carried ou~t by the geneval procedures described in Equation 4.

Equation 11 illustrates tt~e preparation of thioethers of Formula IXc, containing an alpha-cyanooxime moiety, from corresponding aldehydes of Formula XITI.

F'quation 11 0 1) NaBH 4

C

2 fl 5 0y'o 25CC; NQAlk H 2) SOM 2 t C 0 J HS AT; CC I ~acetone, AT;

S

4) alkylnitrite, fOCHV, n 4 CH OHt IQO; xU 5) M-Alk, base

IXQ

wherein Ri, R 4 1 M and Alk are as previously defined.

I

I U.

~4 '4 WO 89/00991 PCT/US88102459 The reactions 1) to 4) of Equation 11 are carried out by gbneraJlly known methods, to provide uncapped oximes of P'ormula IXc, wherein Alk is H.

Subsequent reaction of the uncapped oximes by generally known methods with a suitable base and reagents, M-Alk, in an inert solvent provides capped oximes IXc. Suitable bases and solvents include potassium t.eA.-butoxide in DMF or sodium methoxide in methanol. Reactions 4) and 5) of Equation 11 are further illustrated in Example 7.

In an ai,:logous manner to reactions described 41n Equations 10 and 11, othqr thioethers of Formula IX can be prepared, wherein J is J 2 to J 13 by carrying out reactions on appropriate corresponding carboxylic acids or aldehydes, Equation 1,2 i llustrates the preparation of aldooximes and ketoQximes of Formula IXd, Eution__Ja)

F

1) LDA 2) ClCTd, (CH 3 2 NCTd'1 or CO 2 H 3 0+ -Te NQA 1,k b) X V 1)

XSR

4 2) lI 2 N-A-lk' R2~ SR 4 WO 89/00991 PCT/US88/02459 22 wiierein:

R

2

R

4 and are as p~reviously defined; Tis C 1 to C 3 alk'l. optionally substituted with OCH 3 or SCH 3 Or cyclopropyl; Td' is Td or CF 3

CF

2

CF

3

CF

2

CF

2

CF

3 or H; Teis Td' or CO 2 H; and Te' is Td'- In Rquation 12a, 2-fluoropyridine XIV is metallated with lithium diisopropyl amide (LDA) accordiiig to the procedure of Gungor, et al,, k-~ganmnt. e, 2i-U, pages -39 to 150 (1981), followed by treatment with an acid chloride or a N, N-d ire thyl ami de (or carbon dioxide and H 3 0) by known methods to yie1u' gorresponding ketones or aldehydes (or carboxylic acids). In Equat~ion l2b, reaction of halopyridine XV with an appropriate rnercaptide in a solvent such as DMF yieldls the corresponding thizoethers, which on reaction with an alkoxyamine by known methods yields compounds of Forrnia IXd, U.S. Patent 4,456,469 discloses analogous halopyridine-inercaptide reactions.

Also, by known methods, aldo or keto-thioethers in Equation 12b can be reacted with hydroxylamine followed by a suitable base and an alkylating reagent, M-AlR, to provide capped oximes Ixd. Suitable bases and solvents are described in Equation 11, For details on the reaction of trifluoromethyl ketones with hydroxylamino see, for example, Rosenfeld, U..Pate nt 3,74f&j6. and R. L~.

StIvador et al., J. -Med. Chem.. J5, pages 646 to 650 (1972), WO 89/00991 PCT/US88/02459 23 Oximes of Formula IXd, wherein Te' is CH 2

".S

can be prepared in a two-step procedure from an appropriate 2-benzyl thio-3-pyridyl-ca rboxyl ate ester using generally known methods. Thus, reaction of the ester with a suitable base such as sodium hydride and acetonitrile in an inert solvent such as tetrahydrofuran can provide the corresponding 3-ketoacetonitrile, which on subsequent reaction with an appropriate alkoxyamine, or more preferably, its hydrochloride salt, in an inert soltvent such as methanol or DMF can provide IXd (Tel is CH- 2

CN).

Pyridyl alkyl ketones %desiribed in Equations 12a and 12b can also be prepared by reaction of appropriate pyridyl acid chlorides with alkyl Grignard reagents. For details see, for example, Japanese Patent Application 60-253e531.

Marsais, et al,, J.Orcunet.Chem., 216, pages 139 to 147 (1981) describes the preparation of 3,4 and 2,3-disubstibuted, pyridines by reacting 3-chloropyridine with, respectively, lithiumn dialk31.amides in tetrahydrofuran or butyl lithium in diethyl ether. By reacting such lithium intermediates with reagents described in Equation 12a followed by Equation 12b, the corresponding 3,4- and 2,3- Isomors of IXd can be obtained.

For further details pertaining to the synthesis of pyridines, see Beritmaier, et al., Tetrahedron, j,5907 (1970);, Blank, et, al., JMed.Chem., .1,pages 1065 to 1071 (1974); Mallet, et al., TetLrah~Qn 41t, 3433 (1985); and Delarge, et al1. Annales Phr.Ea" U, 369 (1978); and R. L.

Salvador et al.t Z-etrahtdron 272, pages 1221 to 1226 (1971). The N-oxcidation of pyridine sulfonamides of Formula wh~erein J is 0-6 to J-9, is carried out according to known methods for the oxidation of pyr~idine compounds.

WO 89/00991 PCT/US88/02459 24 Equations 13 and 14 illustrate the preparation of thiophene carboxylic acids of Formula IXe and IXf. The acids can be used as intermediates for preparing compounds analogous to those described in Equation 10. Also, reduction of the acids or their esters can provide methyl alcohols for analogous reactions described in Equation 11.

1

I

Equation 13 R rB 1 S r S 'Br 1) BuLi 2) CO 2

H

3 0 3) 2BuLi 4) (R 4

S)

2 R SR 1 4 S COH 2 CO 2 R 142 1) 2BuLi 2)

(R

4

S)

2 R-CO H S SR 4

H-LT

2 ^S/SRq In Equations 13 and 14, metal-halogen exchange or metallation with carbon dioxide or a disulfide by known methods provides carboxylic acids IXe and IXf. Starting with 3,4- dibromo-thiophene, and carrying out the reactions of Equation 13, can provide the 3,4- substituted isomer of acid IXe.

Further details pertaining to the preparation and

;I

LLLII~Li~L i _j _i r_ 1 1 I WO 89/00991 PCT/US88/02459 functional group manipulation of thiophenes are found in U.S. Patent 4,481,029 and Knight, et al., J.Chem.Soc.Perkin Trans I, pages 791 to 794, (1983).

Equation 15 illustrates the preparation of some pyrazolethioethers of Formula IXg, which can undergo further reactions analogous to those described in Equations 10, 11 and 12.

Equation R L R -Tf 2- C-Tf 2 N KSR 4 N Cl "N SR 4 I DMF or CH OH,

R

3 3

R

about 25 0 C to 80 0

C

XVI IXa wherein Tf is H, C 1 to C 3 alkyl, optionally substituted with OCH 3

SCH

3 or halogen; cyclopropyl, OH or OCH 3 and R 2

R

3 and R 4 are as previously defined.

The compounds of Formula XVI in are known or can be prepared by known methods; see, for example, Kviko et al., Zhurnal Org. Khimi, pages 1685 to 1692 (1969); Koshelev et al., I~bid, pages 1750 to 1754 (1972); and Japanese Patent Application 57-228261.

The butylsulfonamides of Formulas XIX, XXI and XXIII are useful intermediates for preparing compounds of this invention and they can be prepared by known methods or simple modifications thereof.

Several such methods are illustrated in Equations 16, 1n 17 and 18.

PCT/US88/0245 9 WO 89/00991 Equation 16 a)Q

LH

3

XVII

b) XVIII 1) BuLi 3) H Nc (cH 3 4) Br 2 1) 2BuLi Dr SO N.HC (CH 2 3 3 CH 3

XVIII

2) same as Eq. 12a, or CO 2 'H 3 0 -C-Tf so1IN S 2 NHC (CH :d)

C

3

XIX

wherein Tf is as previously defined.

Preparation of intermediates such as bromide XVIII can be found in EPA 95,925. Exposure of bromide XVIII to BuL; followed by treatment an appropriate acid chloride, DMF or carbon dioxide yields XIX.

a) XVII 1) CiSo, H 2) SOC1 2 3) H 2 NC(CH 3 3 1) BuLi 2) samea Eq. 16b so 2 NHC (CH 3 3 CH 3 X ,s ~2 NHC (CH 3 3 C-Tf CH 3 6O b) XX WO 89/00991 PCT/US88/02459 27 In Equation 17, the isomeric 5-keto-4-sulfonamide is prepared as outlined, while in Equation 18, the isomeric 4-keto-3-sulfonamide XXIII is prepared as outlined.

Equation 18 a) H2 Br (CH 3 3CNHSO Br 1) NaNO 2 SO2, CuC1 2) H -XXII 2) H 2 NC(CH 3 3

O

CCHH 3

CH

3 Bu(CH3) 3CNHSO C-Tf 1) BuLi b) XXI1 2) same as Eq. 16b XXIII

CH

3 3 Intermediate compounds of Formula XIX, XXI and XXIII in Equations 16, 17 and 18 can undergo further reactions analogous to those described in, Equations 10, 11 and 12, For further details pertaining to the synthesis of pyrazoles see, for example, EPA 87,780; South African Patent Application 833,350, EPA 95,925; and Jacobs, "Heterocycloc Compounds", Elderfield ed., Vol. 5, pages 45 to 161, Wiley, New York, 1957.

Chemical compatibility of the wide variety of reactions, reactants and reaction conditions described throughout this disclosure with respect to J, R 1 to

R

3

Q

1 and Q 2 must be evaluated and judicious choices made; one skilled in the art, having this disclosure before him, will be able to readily make such WO 89/00991 PCT/US88/02459 28 evaluations and choices without undue difficulty. In addition, incompatibility can readily be avoided in certain instances by suitable selection of a protecting group as will be obvious to one skilled in the art. For a compilation of references describing the wide variety of such protecting groups available, see Greene et al., "Protective Groups in Organic Synthesis", John Wiley and Sons, Inc., New York, 1981.

The heterocyclic amines of Formula V in Equation 2 above can be prepared by methods known in the literature, or simple modifications thereof, by those skilled in the art. For instance, EPA 84,224 and Braker et al., J. Chem. Soc., 69, 3072 (1947), describe methods for preparing aminopyridines and triazines substituted by acetal groups such as dialkoxymethyl or 1.,3-dioxolan-2-yl, among other groups. Also, South African Patent Application Nos. 82/5045 and 82/5671 describe methods for preparing aminopyrimidines and triazines substituted by haloalkyl or haloalkylthio groups such as OCH 2

CH

2

F,

OCH

2

CF

3

SCF

2 H, and OCF 2 H. South African Patent Application 83/7434 describes methods for the synthesis of cyclopropylpyrimidines and triazines substituted by such groups as alkyl, haloalkyl, alkoxy, haloalkoxy, alkylamino, dialkylamino or alkoxyalkyl.

The 5,6-dihydrofuro[2,3-d]pyrimidine-2amines, the cyclopenta[d]pyrimidines-2-amines A is A-2) and the 6,7-dihydro-5H-pyrano[2,3-d]pyrimidin-2amines A is A-3) can be prepared as described in EPA 15,683. The furo[2,3-d]pyrimidin-2-amines A is A-4) are described in EPA 46,677. Compounds of Formula V, where A is A-7, are described in EPA 125,864.

L WO 89/00991 PCT/US88/02459 29 Compounds of Formula V, where A is A-5, are described in EPA 73,562. Compounds of Formula V where A is A-6, are described in EPA 94,260.

In addition, general methods for preparing aminopyrimidines and triazihes have been reviewed in the following publications: "The Chemistry of Heterocyclic Compounds", a series published by Interscience Publ., New York and London; "Pyrimidines", Vol. 16 of the same series by Brown; "a-Triazines and Derivatives", Vol. 13 of the same series by Smolin et al.; U.S. Patent 3,154,547; and Huffman et al., J. Org. Chem., 28, pages 1812 to 1816 (1963), which describes the synthesis of triazines.

Agriculturally suitable salts of compounds of Formula I are also useful herbicides and can be prepared in a number of ways known to the art. For example, metal salts can be made by contacting compounds of Formula I with a solution of an alkali or alkaline earth metal salt having a sufficiently basic anion hydroxide, alkoxide, or carbonate).

Quaternary amine salts can be made by similar techniques.

Salts of compounds of Formula I can also be prepared by exchange of one cation for another.

Cationic exchange can be effected by direct contact of an aqueous solution of a salt of a compound of Formula I alkali or quaternary amine salt) with a solution containing the cation to be exchanged, This method is most effective when the desired salt containing the exchanged cation is insoluble in water and can be separated by filtration.

Exchange can also be effected by passing an aqueous solution of a salt of a compound of Formula I an alkali metal or quaternary amine salt) m ~Y I -i i WO 89/00991 PCT/US88/02459 through a column packed with a cation exchange resin containing the cation to be exchanged for that of the original salt and the desired product is eluted from the column. This method is particularly useful when the desired salt is water-soluble, a potassium, sodium or calcium salt.

Acid addition salts, useful in this invention, can be obtained by reacting a compound of Formula I with a suitable acid, e.g., p-toluenesulfonic acid, trichloroacetic acid or the like.

The preparation of the compounds of this invention is further illustrated by the following specific examples, Unless otherwise indicated, temperatures are in deg:e.es Celsius, EXAMPLE 1 N-Methoxv-2-r(phenylmethyl)thiolbenzamide A suspension of 100 g of 2-[(phenylmethyl)thio]benzoic acid and 97.6 g of thionyl chloride in 800 ml of benzene was refluxed for about three hours then evaporated to dryness under vacuum. The residue was triturated with hexane to yield 101,2 g of 2-[(phenylmethyl)thio]benzoyl chloride, m.p. 1130 to 116 0

C.

To a suspension of 80.2 g of potassium carbonate in 500 ml of water and 200 ml of methylene chloride, cooled at less than 5 0 C with external cooling, was added, portionwise, 48.2 of methoxylamine hydrochloride followed, after about 10 minutes, by the dropwise addition of 101 g of the above acid chloride dissolved in 700 ml of methylene chloride. After the suspension was stirred at 0 C for one hour, then two hours without external cooling, the organic layer was WO 89/00991 PCT/US88/02459 31 separated, dried (MgSO 4 and evaporated to dryness under vacuum. The residue was recrystallized from 1-chlorobutane to yield 79 g of the subject compound, m.p. 1000 to 105 0

C.

EXAMPLE 2, N-Methoxy-2-[ (phenylmethyl)thio]benzene carboximidovl chloride To a suspension of 79 g of the product of Example 1 in 1500 ml of benzene under a N 2 atmosphere, cooled at 20° to 300C with external cooling, was added, portionwise, 60.2 g of phosphorous pentachloride. After stirring at 25 0 C for about 24 hours, the suspension was warmed at 40 0 C for about four hours, then cooled to 25°C and filtered, the filtrate was evaporated at less than 40°C under vacuum, and residue was chromatographed on silica gel with methylene chloride as eluant to yield 47 g of the subject compound as a crude yellow oil.

NMR(CDC1 3 ppm 4.15 3H, OCH 3 4.6 2H, CH 2 7.4 9H, Ar).

EXAMPLE 3 2-(Chlorosulfonyl)-N-methoxybenzenecarboximidoyl chloride To a solution of 10 g of the product of Example 2 and 1.9 g of water in 125 ml of glacial acetic acid, cooled at about 130C with external cooling, was added, dropwise, 8.6 ml of chlorine.

After stirring at 100 to 15°C for one hour, the suspension was poured into excess ice-water, and the L ilr _I i: 1 WO 89/0099 1 PGT/U588/02459 32 mixture was extracted with 1-chiorobutane. The extraction was washed with water, twice with saturated aqueous sodium bicarbonate, then again with water, then dried (MgSQ 4 and evaporated' at less than 40 0

C

under vacuum to yield the subject compound as a crude oil.

EXAMPLE 4 2-(Aminosulf onyl) -N-methoxybenzenechloride To a solution of the oil prepared in Examplie- 3 in 100 ml of tetrahydrofuran, cooled at 0 C with external cooling, was added dropwise 1.7 ml of ammonia. After stirring at -30 0 C for about minutes, the suspension was purged with N 2 to remove excess ammonia, then evaporated at less than 300C under vacuum. After adding ice-water to the residuef the suspension was extracted with methylene chloride, dried (MgSO 4 and evaporated under vacuum, The residue was triturated with hexane to yield 2.5 9 of the subject compound as a crude solid, m~p. 1,550 to 158-C, NMR(CDCl 3

DMSO):

PPM 3H, OCH 3 6.6 (bs, 2H, NH- 2 7.8 (in, 4H, Ar).

2- [r(4-Methoxy-6-methyl-2---rimidinyl) aminocarbonyl] aminosu 1 .ronyl3-N-riethc,-xybenzenecarboximidoyl chlorid.. -i suspension of 0.4 g of the product of Examplt and 0.46 g of phenyl (4-methoxy-6methylp-rrimidin-2-vi)carbamate in 10 ml of dry .7,cetonitrile was added 0.25 g of, DBUJ. The suspension was stirred for about two hours at room WO 89/00991 PCT/US88/02459 33 temperature, then diluted with excess water and filtered. The filtrate was acidified with concentrated hydrochloric acid to yield a precipitate. After filtration, the residue was washed with excess water and suction-dried to yield 0.35 g of the subject compound, m.p. 1780 to 179 0

C;

IR(Nujol): 1700 cm- 1 NMR (CDC1 3 PPM 2.4 3H, CH 3 3.9 3H, OCH3) 3,95 3, NOCH3) 6.3 1H, py-) 7,3 1H, NH) 1H, Ar) 7.7 2H, Ar) 8.4 1W Ar) 13.2 (bs, 11, NH), EXAMPLE 6 N-Methoxy-2-tl [(4-methoxy-6-methyl- 1,3,5-triazin-2-yl)amino]carbonyl amino]sulfonyll .benzenecarboximidoyl chloride By the procedure of Example 5, 0,4 q of the 20 product of Example 4 was reacted with 0.46 9 of phenyl (4-methoxy-6-methyl-1,3,5-triazin-2-y1)carbamate and 0,25 g of DBU. The resulting suspension was acidified, without prior filtration, with concentrated hydrochloric acid and filtered, The residue was washed with excess water and suction-dried to yield 0.45 y of the subject compound, m,p 1826 to l844, IR (Nujol): 1700 cm-I (C=O) Li ~I 1 WO 89/00991 PCT/US88/02459 34 NMR (CDCl 3 ppm 2.6 3H, CH 3 3.95 3H, NOCH3) 4.1 3H, OCH 7.4 (bs, 1H, NH) 7.5 1H, Ar) 7.7 2H, Ar) 8.4 IH, Ar) 12.4 (bs, 1H, NH).

EXAMPLE 7 Alpha-(Methoyimino)-2-[(phenylmethyl)thio1lbenzenezcetonitrile- A suspension of 41 g of 2-[(phenylmethyl)thio]benzeneacetonitrile and 9,4 9 of sodium methoxide in 350 ml of methanol, under a N 2 atmosphere, was stirred at 25 0 C for one hour, then refluxed one hour and cooled to 100C. Then, n-butyl nitrite (17.7 g) was added dropwise and the suspension was stirred at about 2500 for 16 hours, then evaporated under vacuum, Excess water was added to the residue and the emulsion was washed with methylene chloride to yield a 3-phase water-oil-methylene chloride mixture. The oil layert was separated and acidified in water with concentrated hydrochloric acid. The suspension was extracted with methylene chloride, dried (M0SO 4 and evaporated under vacuum to yield 26.9 g of crude A1hpk-(hydroxyimino)-2- (phenyinmethyl)thio benzeneacetonitrile as an oil.

To 15 g of the above oil in 125 ml of DMF, under N 2 was add1ed 6,6 of potassium Lte-bttoxide 1 After stirring io7r one hour, the suspension uas heated at 50 0 C for one hourt, then 7.1 9 of dimethy'. sulfate was added dropwise at 40 0 C, The suspension was iA IMd WO 89/0099 1 PCT/US88/02459 stirred at 250C overnight, diluted with excess water, extracted with diithyl ether, and the extracts dried (MgSO 4 and evopc~rated under vacuum, the residue was chromaitographed on silica gel with methylene chloride to yield 13 g of the subject compound as an oil.

NMR (CDCl 3 ppm 4.0-4.2 (in, 5H, OCH 3

CH

2 7.4 (mn, 9H, Ar).

EXAMPLE 8 2-rCvano(rn-ethoxvimino)methvllbcnzenesulfonamide By the procedure of Example 3, 11 g of the product of Example 7 was reacted with, 2,2 g of water and 9.9 ml of chlorine in 1,25 ml of glacial acetic acid, After work-up, 2-[cyano(methoxyimino)mehyl1benzenesulfonyl chloride was obtained as a crude oil, By tht procedure of Example 4, all of the above oil wac reacted with 1.7 ml of ammonia in 100 ml of tet-rahydrofuran. Following work-up, the residue was trit,.rated with hexane and recrystallized from 1-chlorobutane to yield 2 g of the subject compound; in.p. $26 to NMR (CDC1 3 PPM 4.3 3H, OCH 3 5.4 (bs, 2H1, NI{ 2 7.7 (in 3H, At) 8.2, 21IH Ar), 2-[(Cyano) (methoxyimino)inethylj-IN-f(4,6-dimetoxyri nz ~i 2 Y fiino I ca rbonyl I boqzenes u If~o;2ami de By the procedu~re of Example 51 0.4 9j of the product of Examnple 8 was reacted with 0,51 g of (1972).

WO 89/00991 PCT/US88/02459 36 pilenyl (4,o-dimethoxy-l,3,5-triazin-2-yl)carbanate and 0.28 g of DBU in 10 ml of dry acetonitrile to yield 0.6 g of the subject compound; m.p. 1910 to 194 0

C.

IR (Nujol) 1710 crtF 1

(C=O)

NMR (CDCl 3 PPM 4.1 (s 6H, OCfl 3 4.2 3H, VIOCH 3 7.4 (bs, 1H, NH) 7.6 (mn, 1H, Ar) 7.8 (mn, 2H, Ar) (mn, lH, Ar) 12.3 (bst 1H, NH).

Usin7 th- techniques described in Equations 1 through 18 and Examples 5, 6 and or simple modifications thereof, the following compounds in Taibles I. through 9 can be made.

WO 89/00991 PCTr/US8/O2459 37 General Formulas for Tables I to 9 GTeneral Formula 1 General Formula 2 General Formula 3 General Formula 4 3so 2 HCN4-

N

p'S0 2

HC

R

N-

PCT/US88/02459 WO 89/00991 38 General Formulas for Tables 1 to 9 (continued) General Formula General Formula, 6 0 OCH3 3502 1HCNCH 2

NQ

X3 General Formula 7 General Formula 8 CN X 0 22 3 SO 2

NHEN-\

General Formula 9 WO 89/00991 PCT/kIS88/0-2459 TABLEr 1 General Formula1 11 E R RL T L Auk x~ J-1 H J-1 H J-1 H lo J-

H

J-1 H J-1 H J-1 H

H

J-1 H J-1 H J-1 H J-1 H 3-1 H J-i, H 3-1 H 3-1 H J-1 H J- H J-1

H

3-1 H J-i H J-1 H j- H H Cl CH 3 0CH H Cl CH 3 CH3 H l H3 3l H Cl CH H H c CH3 OH3 H Cl CH 3 C H Ci, CH BrH H Cl CH 3 H3 H Cl CH OCH3 H c CH3 3 H Cl CH 3 OCH 2C H l H3 CF3 H Cl 13 CH OCFH H Cl CH 3 CH 2c H Cl CH1 CH 2B H l li3 3 H Ci CH CH1 H Cl CH 3 CH 2C OCH 3 OCH 3 CH 3 OCH 3 OCH 3 CH 3

H

CH:E

2 OCH 3 oc2 3 CH 2OCH3 CH2 OH3 OCH 3 OCH 3 OCE 3 OCH 3 OCH 3 OCH 3 OCH 3 OCH 3 OCE 3 OCH 3 I 1- WO 89/00991 PCT/U588/02459 TABLE 1 (Cont'd) I E a 2 d E R LZR 12Z Alk -XL J-1

H

J-1 H J-1 H J-1 H J-1 H J-1 H J-1 H J-1

H

J-1 CH 2 H J-1 CU H J-1 H J-1

H

J-1

H

j-

H

J-1

H

J-1

H

J-1 H J-2 U J-1 H J-1

H

J-1

H

J-1 H H Cl H Cl H Cl H Cl H Ci H Cl H Ci H Cl H Ci H CN H Cl H Cl H Ci H Ci H Ci H Cl H Cl H Ci H Cl H i H Cl H Cl H Cl CH3 OC2CH

CF

CH OCH CHF2 CU3 OCH CF3 CH3 Cl CH OC2H5 CH 3 OCR3 CH 3 OCF 2 CH3 25 CH

OCH,

33 CU OCR 3 3 2 2CH CU Cl C 2 H5 Br C 2 N CH 3 C25

OCRI

C 2 H 5 CF 2 CUH5 OCH 3 C2 H5 CH3 CUH CUrl 2 H5 cu 3 C2 H5 OR3

OCR

3

CU

3

CH

3 OC 3 25g

NWCU

3 2 3 Cla 2SCH 3

CH

3 OCF H 2

OCH

3

OCH

3

OCU

3

OCH

3

CU

3

OCH

3

H

CH OC2

H

2

OCRH

3

CH(OCHU

OCH

25C9 oc2 3 CH OCR 3 C2 OR3 I I e WO3 89/00991 PCT/US88/02459 41 TABLE (L±Cotidl 12 12 2 LZ E LR. ILL A _BLL 5J-1 H H e1 C2H5 J-1 -H H Cl

CH

2H5 -1 H Cl C2H J-1 H H 01 O2H J-1 H H cl c 2 H J-1 H H cl O2H5 J-1 H H

OH

25g J-1 H H 01

OH

25S J-1 H H Cl O2H5 J-1 H H CI C2H5 J- J1 H H cl c 2 H J-1 H H C) 021H5 J-1 H H C

CH

J--1 H H CI C H 255;1 H H l C25 3-1 H H Cl C2H5 -1 H H Cl

C

2

H

5 J-1 H H c 1 n-C 3 H J-1 i H c 3 n-C 3 H J-1 H H Cl n3H7 0-i H H 0I n-CH7 J-1 H H Cl n-O3H7 337 0CH 3 0C 2

H

OCHCF3

OF

3 CH F 2 CH Cl CH Br

F

I

OCH OH F 22MZ OCH CH OF OCH 2HF2 OH2 2F 0011 CF OCH3 OC2 H 25 Cl

OCH

CH

3 CH3 Br

CH

OCH 3 OCH 3 OCH3

OCH

3

OCH

3

OCH

3

OCH

3

OCH

3

OCH

3

OCH

3 CH0

NHCH

3 CH SCH3 CH 3 OCF

H

2 OCH 3

OCH

3 CH3 OCH3 OCH3 WO 89/00991 PCT/US88/02459 42 TABLE I (Cont'd) 11 -E 1 2 12/T

J-

J-1 J-1 J-1 10J1 J-1 J-1 J-1

J.-I

J-1 J- 1

J-

Jl-1 J-1 J-1 j- J-,1 J-1 J-1 J-1 J-1

H

Alk n-C 3H7 n-C 3H7 n-C 3H n-C 3H7 n-C 3H7 n-C 3H7 n-C 3H7 n-C 3H7 n-C 3H7 n-C 3H7 n-C 3H7 n-C 3H7 n-C 3H7 n-C 3H7 CM 3 OCH 3 OCH 3 OCF 2H OCH 3 CH 3

CHM

3 OCH 3 OCH

H

0CM CF3 CF 3 CH2 CH 2Cl CH 2Br 2

I

0CM CM CF3 0CH CHF2 0CM CF3 Cl OC2 OH3 CH 2OCH

H

2 OCH 3 2 2C 3 OCH 0C 2C 3

OCM

CH 3 0CM 3

H

0C 3 1-.1 '-4tUOL=L11dLY dliurne sait) WO 89/0099 1 PCT/US88/02459 43 TARLE 1 (Cont'd) I FR R1 R2 1I/2 j-1 J-1 J-1 J-1 J-1 151

H

Alk n-C 3H7 n-C 3H7 n-C 3H7 CH (CH 3 2 CH(CH 3 2 CH (CH 3 2 CH (CH 3 2 CH(CH 3 2 CH (CH32 CH (CH CH

(CHR)

CH (CH 3 2

CRH(%CH

3 2

CH(CR"

3 2 CH (CH32 CHR(CH32 CHR(CH 2 CH (CH 3 2 OCR 3 OCF 2H OCH 3 CR 3 CR 3 ci Br CH 3 OCH 3 OCR 3 GCF 2 H OCH 3 CR 3 CR 3 OCR 3 OCR 3 OC 2H5 OCH CF3 CF 3 CH2F CR Cl CR Br CH2 S 3 CR 3 OCF 2H OCR 3 OCR 3 CR 3 OCR 3 OCR 3

H

CR OC OCR 3 CH(OCH 3 )2 OC CR

OCR

2C 3 2C 3 OCH 3 OCR 3 OCR 3 WO 89/00991 WO 8900991PCT/US88/02459 TABLE 1 (Cont'd) l fL R 12n J-1 H H J-1 H H J-1 H H J-1 H H J-1 H H J-1 H H J-1 H H J-1 H H J-1 H H J-1 H H J-1 H H J-1 H H J-1 H H j-1 H H J-1 I H J-1 H H J-1 H H J-1 H H J-1 H H J- H H J-1 H H MILT Alk Cl CH (CH 3) Cl CH (CH 3)2 cl C (CH3 )2 Cl CH (CH 3) C 1 CH H3 )2 Cl CH (CH 3 2 Cl CH (CH 3 2 Cl CH (CH 3 2 c 1 CH(CH8) Cl

CH(

3 Cl CH(C 32 Cl

CH(

3 Cl

CH(

3

I

CN CH 3 CN CH 3 CN CH 3 CN CH 3 CN CH 3 CN CH 3 CN CH 3 CN CH 3 F

OCH

3 I OCH 3 OHCH 2F DCH 3 OC H2 CF3OH3 DCH2 CHF CH3 OH22F3 CH3 DCI 2H5 NCHF 3 QF2 2 C 3 CH CF CI 3 3 Cl DCII 25 NCH 3 CH CI SCI OC2 3 OCF 2H OC3 2C 3 HOH3) CII 3CH 2O 3 WO 89/00991 T/S8029 PCT/US88/02459 TABLE 1 (Coflt'd) 11 F, R 12R 12a'U J1-1

H

J-1 H cl-1 H J-1 H cl-1 H cl-1 H J-1 H J-i1 H cl-1 H cl-1 H cl-i H cl-i

H

Jl-i1 H cl-i1 H cl-1 H j-1 H cl-i1 H Jl-.I H cl-i~ 3i 1 H Jl-1 H cl-1 H Jl-1 H H CN CH 3 H CN CH 3 H CN CH 3 H CN CH 3 H CN CH 3 H CN CH 3 H CN CH 3 H CN

CH

H CN CH 3 H CN CH 3 H CN CH 3 H CN CH3 H CN CH 3 H CN CH 3 H CN CH 3 H CN

CH

3 H CN CH 3 H OCH 3CH3 H OCH3 CH3 H OCH

CHM

H OCH 3CH 0CM CH O 3 c2 3 3C 5

OC

OCH 2 F3 OCH3 253 C 3 CH F OCH 3 F 0CM 3 O2 C OCH 3 OC H 2 CF OCH 3 FC 2 0F2 CHM 3 I OCH 2C

H

3 OCH CH F CH 2S 3 0CMCH CF 0CH 223 3 C 2H3 C 3 ci OCH3

~I

WO 89/00991 PCT/US88/02459 IAUE 1 (ContId) j E R j-1 H J-1 H J-1 H J-1 H 1 -0 1 H J-1 H J- H J-1 H J-1 H J-1 H 3-1 H J-1 H J-1 H J-1 H 3-1 H j-1

H

J-1 H J-1 H J-1 H 30-1 H J-1 H J-1 H J-1 H 12 12 KLR L1 Z A U H OCR CH3 H OCH3 CH3 H OCR

CR

H OCH3 CH3 H OCR

CR

H OCH3 CH3 H OCR

CR

H OCH3 CH3 H OCH3

CR

H OCH3 CH3 H OCH3 CR 3 H OCH3 CH3 H OCR CH3 OCH3 CH3 H OCR CH3 H 063 C3 H OCR 3 CH 3 H OCH 3 cli H OCH3

CR

H OCR3

CR

H

OCR

3 CR H OCRj CH3 H OCH3

CH

H OCH 3CH3 Br

OCH

3 CH3

H

OCH H OCR3 CH OC H ol3 CH2 c2 OCF 2H

OCH

3 OCR1 CH(OCH 3 2 :33 CH3 CH 2 CH 2 OCH OCH3 C2HCH3 CH CR OC 2 2 3 Oct CF OC

R

CF3 OCH 3 CHR2 FCH3 CH32B O25 OCH

OCR

OCH 2CHF

OCR

OH2c 2F3 C 3 OCH OCHF 2

CH

3 CH2CF 3

CR

3 CRl QC 2 3 J i WO 89/00991 PC/US88/02459 47 TABLE 1 (Cont'd 1 2 1F, 2 LLR..

IIRL

j-1 J-1 J-1 J-1 J-1 J-1 J-1 J-1 L1J J-1 J-1 J.1 I-1 J-1 Ji LIi J-1 j-1

H

H:

H

OCH

3

OCH

3

OCH

3

OCH

3 N (CH 3 )2

N(CH

3 2

N(CH

3 )2

N(CH

3 2 N (CH 3)2

N(CH

3 2 N(CH 3 2 N(CH 3 2 N (CH 3 2

N(CH

3 2

N(CH

3 2 N (CH 3 2 N(CH 3 2

N(CH

3 2 N (CH 3 )2

-K-

oc 2 O25g

OCH

3 OCF H 2 C1

CH

3

CH

3 Cl Br

CH

3 0CM 3 OCR 3 OCF H 2 CH 3

QCH

3 CH 3 OCH OC 3

CF

3 CH2

NHCH

3 CH SC3 2 C3

CH

3 OCF H 2

OCH

3

CH

3 4CM 3 OCH3

H

CH

2

OC

2

H

CH(OCM

3 2 QC 2 H

CH

2

OCR

3 2cl 3

OCH

3 OC-I J-1 H H (CH 3 2 CH 3 CM Cl

OCM

3 WO 89/00991 WO 89/099 1PCT/US88/02459 48 TABLE I (Cont'd) 'a 1 E 2 iR Za J1 J-1 J"1 3-1 J-1 J.-1 J-1 J-1 j.1 J-1 -1

H

N (CH 3 )2 N (CH 3 2 N (CH 3 2 N (C32

(C

3 ~2 N (CH 3 2 N (CH32

N(CH

3 2 N (C;H 3 2 N(C H 2 32 Cli

CN

Cli

CN

Cli CH 3 CH 3 CH 3 CH 3 CH 3 Cli 3 CH 3 CH 3 CH3 C H3 C H 2.5

C

2

H

n-C 3 7 n-C 3

H

7 CH (CH 3 2 CH (CH3 CH (CH 3) CH 2Br

F

I

OCH 2CH 2F OCH 2CH

CF

OCH 2Cl-Fz OCH 2CF3 Cl 00 2 H 5 Cl

QCH

3 clI Cfl

CH

3 Ci.

O3

CH

OCH 3 OCH 3 OCH 3 OCH 3

OCH

3 2 NHCH 3 ca 3 QCF 2H OCR 3 ca 3 0CH 3 OcR. CH3 CH 3 WO 89/00991 PCT/US88/92459 49 TABLE 1 (Contd) Ii F R 1 2 1 J2 L I J-1 H H CN CH(CH 3 2 OCH3 J-1 H H 0Ch C H 4 OCH 30CM 3 J- H OH3 c2 H5 CH3 3 J-1 H H OCH 3 C 2H 5 CH 3CH 3 J- H O H3 C2 5 3lOC J-1 H H OCRM UC H 7 CH 3 C J1 -H OH3 25 H7 Q 3 O 3 1 H 0CR nC H CH CH J-1 H H OR3 25C3 l C J-1 -H H 0CM l(C O)CHi OCH 3 J-1 H Hi OCH 3 z~C( 3 )2 CM OCM 3 J7-1 H 11 001213 C M 011H3 OC 3 25J-1 -H H 0C 3 2 -5CM C C H 013 J-i H H c 0C5 CH 3

CM

3 OCM 3 JT- H HHc 11 001 CM(C1R 3 5 2 0113 0CM 3 J-1 H H 0CM 3

CM(CMH)

2 CH 3 CMi J1 U H 0CM5 CH(CM 3 C I 0013 1 H 0,C 2H5 43 R7 OR3OC J-1 H H C 2 H 5 nC 3 H7 Ctl 3

OC

3 WO 89/00991 PCT/US88/02459 'TABLE I (Cont'd) 11 RLeL MIL ji-1 J-1 J-1 J-1 101 J.-1 3.-1 -1 151 J-1 J-1

J-

J-1 j-1.j J-1 J-1 3-i-

H

OCH 3 OC 2H5 OC 7.H5 OC 2H5 OC 2H SCM 3 SCH 3 SCM 3 SCM 3 S CN 13r NHCH 3 NHC 2H N~ (Cli 3

)C

2 H N(c n-C 3H7 D-C 3H7 CH(CH 3 2 CH (C!4 3 2 CH (CH 3 2 CH (CH 3)2 CH32 CH 3 CH 3 CH 3 CM 3 CH 3 CH 3 CH 3 CM 3 CH 3 CM 3

CHM

3 CH 3 CH 3 CM 3 Cl CH 3 CM I

CF

CH 3

CH-.

C I CH 3 C.4 OCH 3 0CM 3 OCH 3 OCM 3 CH 3 0C14 3 OCH 3 OCH 3 CM 3 OCR 3 I)CH 3 CH 3 0CM 0CH 3 CH 3

OCR

OR3 OCp OCR 3 OH3 3.iH H N (QCA 3 rif 3 ,M 3 I FI WO 89/00991 PCT/US88/02459 ThBLE 1 (Cont'd).

J-1 H

H

J-1 H

H

J-1 H

H

3-1 H H 3-1 H H J-7 H H (n=o) J-7 H H (n=O) J-7 H H (no) J-7 H H (n=o) J-7 H H (n=O) J-7 H H (n=O) 3-7 H H (nzo) J-7 H H (n=o) J-7 H H (n=O) 0-7 H H (nroO) 0-7 H H (n=O) J-7 H H (n=O) J-7 H H (nO) J-7 H (n=O) 1 2 N(OCH )CH CH 3 3 3

N(OCH

3

)CH

3

CH

3 N(OCH 3)CH 3CH3 N(CH 23 CH 3

N(CH

2 )4 CH3 H

CH

3 H

CH

3 H

CH

3 H CH3 H C 2 H H C HF H 2H5 2:5 H OH~ H 25 H n-C 3

H

7 CH (Cli 3) CH

CHC

3 1CH7

CHI

C C 2 C

CH;(CH

3 2

CA

3

CH

3

CH

3 CH 3 Cl

OCH

3

OCH

3

OCH

3 CH3

OH

3 Cl

CH

3

CH

3 Cl

OCH

3

OCH

3

OCH

3 QCHa

OCH

3

OCH

3

-X-

OCH

3

CH

3

OCH

3

OCH

3

OCH

3

CM

3

OCH

3

OCH

3

OCH

3

OH

3

OCH

OCH 3

QCH

3 OCH 3 OCH 3 c WO 89/00991 WO 8900991PCT/US88/02459 11 B HRLe.

J-7 H H (n=O) J-7 H H (xi=O) J-7 H H (n=O) J-7 H H (n=O) J-7 H H (n=o) J-7 H H (n=O) J-7 H H (n=O) J-7 H H (n=O) J-7 H H (n0O) J-7 1 H (n=O) J-7 H H (n=O) J-7 H H (n~o) J-7 H H (n=O) J-7 H H (n~o) J-7 H H (n=o) J-7 H H (n~o) J-7 H H (n=o) J-7 H H (n=O) cycylopropyl CM 3 cycylopropyl OH 3 cycylopropy. CM 3 3 Cl

CHM

3 Cl CM 3 Cl CH 3 ON OH 3 CN OH 3 ON OH 3 ON

CH

0CH 3 CH 0CM 3 CM1 0CH 3 CH N(OH 3)2 OH3 N(CH 3)2

CHM

OH 3 CM 3 Cl

OCH

CHM

3 Cl 0CM 3 OH 3

CHM

3 Cl 0CM 3 OH 3 OH 3 Cl 00H 3 0IA 3 y7L OCH 3 0CM 3 CH 3 0CH 3 0CM 3 0CM 3 CH 3 0CM 3 OCH 3 0CM 3 OIH. 3 0CM 3 OCM 3 00H 3 CM 3 0CM 3 0CM 3 0CM 3 ji H H C3 O 2H2 FOH3 WO 89/00991 PCT/US88/02459 TABLE 1 (Cont'd) .I ~E 12LR 5J7 H H (n=O) J-7 H H (n=o) J-7 H H (n=1) J-7 H H (n=1) J-2 H H J-2 H H J2 H H J2 H H, J-2 H H J-2 H H J-2 H H j.-2 H H J-2 H H J-2 H H ~j-2 H H J-2 H J-2 H H J-2 H H -2H H J-2 1-1 j-3 H H J-3 H H 1I/2 N (CM 3 2 N (CM )2 Cl 0CM 3 O 3 OH3 OCH 3 0CM H Cl Cl Cl

CN

C

3 OCH 3 N (C C 3 )2 N (CH 3)2 N (CH 3)2 Cl Cl CM 3 CH 3 CM 3 CM 3 CM 3 ClM 3 CM 3 CH 3 CM 3 CH 3

CHM

3 CM 3 CM 3

CHM

3 CM 3 CM 3 CM 3

CHM

3

CHM

3 CM 3

CM

Cl CM 3

OC

CM 3 CM 3 Cl CM 3 CM 3 Cl

CHM

3 CM 3 CM 3 CH 3 CM 3 0CM 3 0CM 3 0CM 3 U--L II 12 5 3 WO 89/00991 PCT/US88/02459 54 TABLE 1 (Cont'd) Al F, R R12 1/2 Alk y J-3 H H Cl CHR CR CH3 J- H H CN

CH

3 OCH3 OCR J-3 H H CN CH 3

CH

3 OCR3 J-3 H H CM CR CR CR -3 H H CM

CH

3 Cl OCR 3 J-3 H H OCR 3 CR OCH OCH3 J-3 H H OCR 3 CH3 CR OCH3 J-3 H H OCR 3 CR CR Cli J-3 H OCR3 CR3 Cl OCR J-3 H H N(7.13)2 CHR OCH OCR -3 H H N(CH3)2 CR CR3 OCH J-3 H H N(CH)2

CH

3

CH

3

CR

3 J-3 H H M(CR )2 CR3 Cl OCR 3 J-4 H 1. C CH 3 OCH 3 OCH 3 J-4 H H CN CH 3 OH3 C OCR3 J-4 H H OCH3 CH3 OCH 3 OC3 5-4 H HN 3 )C2 R 3 OCR 3 OCH 3 H H CR CR OCR OCR 3 3 3 H H C Ci CHR

OCR

H H Cl Cl CHR CH 3 3 3 H H Cl C3 CR CH J-5 H H CM CR OCR3 OCR 35333 H H Cl n-C3H7 Br OCH 3 WO 89/00991 PCT/US88/02459 J-5 J-5 J-6 (n=0) J-6 (nl) 3-8 (n~0o J-8 (n=l) J-9 (n=O) j-10 R=CH 3

(R

3

=CH

3 (R3 CH J-11

(R

3 CH 3 J-11

(H

3

=CH

3 7-l1, R3 CH3 J-12

(R

3

=CH

3 J-12 3

=CH

3 1 2

H

1 2 IL2

CN

0CM 3

N(CH

3

H

C1

CN

Cl

CN

H

Cl

CN

TABLE 1 (Cont'd) Alk

CH

3

CH

3

CH

3

CH

3 )2 CH 3

CH

3

CH

3

CH

3

IH

3

CH

3

CH

3

CH

3

CM

3

CH

3

CH

3

CH

3 CH3

CH,

CH3

CH

3 OCH3

CH

3

CCH

3

OCH

3 0CH 3

OCH

3 OCH 3 0CH 3 OCH 3 OCH 3 OCH 3

OCH

3

OCH

3 OCH 3 y

OCH

3

CH

3

OCH

3 OCH 3

OCH

3 OCH 3 OCH 3

OCH

3

OCH

3

OCH

3 OCH 3 OCH3 OCH 3 OCH 3 OCH 3 OCH 3 OCH 3 i .r 1- J-1 H H Cl n-CH

OCH

3H7 25g

NHCH

3 PCT/US88/02459 WO 89/00991 I B R R/R2 J-12 H H (R =CH3 J-13 H H

(R

3

CH

3 J-13 H H

(R

3

=CH

3 J-13 H H

(R

3

=CH

3 0-12 H CH3 (R3 =C

H

3-11 H H (R =CH(CH 3) H H

(R

3 =n-C 3

H

7 J-12 H

CH

3

(R

3 =C H) J-11 H H

(R

3

=CH

2

CF

3 J-12 H H

(R

3

=CH

2 CH=CH 2) 1-1 H H J- H H J-1 H H 3-1 H H -1 H H 3-1 H H J-1 H H 3-1 H

H

TABLE 1 (Cont'd) 12I Alk H

CH

3 cl

CHH

3 CN (H3 H

CH

3 H

CH

3 H

CH

3 cyclopropy1

CH

3 H

CH

3 CH3

CH

3 H CH 3 cl

CH

3 Cl CH 3 Cl

CH

3 CN

CH

3 Cl CH 3 Cl

CH

3 Cl

CH

3 Cl

CH

3

OCH

3

OCH

3

OCH

3 OCH j

OCH

3

OCH

3

OCH

3

OCH

3

OCH

3

OCH

3

NH

2 11-C 3H7

NHCH

3 0CH 3

OCX

3

OCH

3 OCH 3

OCH

3

-II.

OCH

3

OCH

3

OCH

3

OCH

3

OCH

3

OCH

3

OCH

3

OCH

3 OCH 3 OCH 3 0CH 3 OCH 3

SCH

3

SCF

2

H

QCH 2c:-:cti OCH CH=CH2 2 2H H H Cl CR(CH 3) 2 CH 2Br OCH 3 WO 89/00991 PCT/US88/02459 57 TABLE I. (Cont'd) ii B R 1 2 12a j-1 J-7 (n=O) J-1 i J-1 J-1 J-i J-1 J-1 J-1 J-1 J-1 j-1 J-4' 0-1 J-1 J -1 3-i J-1 J-1, J-7 (n=o)

H

Akk CH 3 CH 3 CH 3 CH 3 CH 3 CH 3 CH 3

CHR

3 CH 3 CH 3

CHR

3 CH 3 CH 3

CHR

3 CH 3 OCH 3 OCH 3 OCH 3 OCH 3 OCR 3 -CH3 OCH 3 OCH 3 OCH 3 OCH 3 OCH

I

N (CH 3 2 cyclopropyl NH 2 CF 3 OCR CR OCR CH 2SCH3

CHO

COCH 3 CH(SCH 3 )0C 2 H C(CH 3 )(SCR 3 2 C(Sc2 H5)2 1,3-dioxolan-2-yl H H Cl CH 4 H H Cl CHI OCH3 -eh -1 oivathiola n-2 -yi OQC 3 1# 3-oxathian-2-.yi OCR 3 2-methyl-1,.3- OCR 4-methyi-1,3dioxolari-2-yJ.

OCR 2-4-dci3mthl'1i,3- OCRI3 N(OCH 3 )(CH 3 OH3 3 ECc OCR 3 cR2H OCR OCFl Br OCR

OCR

H

U

CH 3 .3 CR 3

CHR

3 H 6-F H, CR 3

I

J-1 H H CN

CH

3 CH3 CH OCH3 I wo 89/00991 PCT/US88/02459 58 TABLE 1 (Contid) 1 2 d B R RJ.B J-1 H 5-F J-1 H 6-Cl J-2 H 4-Cl J-7 H 6-Br (n=O) J- H 5-Br J-3 H 4-CH 3 J-12 H 3-CH 3

(R

3

=CH

3 J-1 H S-CH CN I-1 H 5-OCH 3 -1 H 5-SCH 3 2 -12 H 3-CH3

(R

3

=CH

3 J-12 H 3 -Ci l3 (R 3CH J-12 H 3 C1-I R 3 CH 3 lI- H 5-OCF H J-7 CH H H (z~0) L-1 C3 H C H3 H J-1 CH H J-1 CH 3 H J-2 CH n 3 CH- C 3

H

12 Cl Cl Cl

H

Cl

C'

H

Cl Cl

CL

H

Alk

CH

3

CH

3

CH

3

CH

3

CH

3

C

3

CH

3

CH

3

CH

3

CH

3

CH

3 yY OC 3 OCR 3 OCR3 OCR3 OCH

CM

OCR3 OCR3 OCH3 OCH3 OCR 3 OCR 3 OCR3 OCR3 OCH3 OCM3 OCR3 OCR3 OCH3

OCR

CH3

OCH

H

CH

3 H CH 3 Cl

OCH

3 OCH3

OCH

OC3 OCM 3 OCR3

OCR

3 CH, OCH 3 OCI3 OC3.

C4 OCt!

OC!

3 OC{ 3 OR3 OR3 fI

I

J-1 H H OCH 3CH 3Cl OCH 3 WO 89100991 PCT/US88/02459 J-7 CH 3H (n =0) J-1i H 6-Cl J-1 H 6-Cl J-1 H 6-Cl J-l H 6-Cl J-7 H H (n=O) J-7 H H (n=O) J-7 Hi H (n=O) 3-7 H H (n=o) J7 H H (n=O) j H H J- H H (n=o) 3-7 H H (n=O) J-7 H H (n~o) J-7 H H 0-7 H H (n=O) J-7 It~ H (n=0O) J-7 Hi H (n=O) 0-7 H H (n=Q) a-7 H H (n=O) J-7 H H (n=O) J-7 H J-7 H H 3 5 (n=O) 12a

H

CN

CF3 CF 3 CF 3 CF 3 CF 3 CF 3 CF 3 CF 3 CF 3 CF 3 c 3 CF 3 Cr 3 CF 3 CF 3 CF 3 CF 3 Alk CH 3 CH 3 CH 3 CH 3 CH 3 CH 3 CH 3 CH 3 CH 3 CH 2CH3 CH 2CH3 n- 37 C H H n-C H4 n-C H7 OCH 3 OCH 3 CH 3 CH 3 Cl OCH 3 CH 3

CHU

3 Cl CH 3 Cl 0CH 3 CH 3 CH 3 Cl OCH 3 OCX 3 CH 3 OCH 3 OCH 3 CH 3 OCH 3

OCHI

CH

.CH3 OCX 3 OCX 3 CH 3 CH 3 OR3 OC14 3 CH(CH 3 2

OCX

3 CH(CH 3)2

CHU

CH(CH 3 2

CHU

3 CH(CH 3) ZCl CHU CN

OCX

CH2CN,

CH

J-1 H H OCR CH3 Cl OCR2H

K

WO 89/00991 PCT/US88/02459 7ABLE 1 (continued) I E R1Z/ 5L-7 H H (n=0) J-7 1 H (n=o) 0-7 H H (n=o) J-7 H H (n=o) 3-7 H H (no) J-7 H H (n=o) 3-7 CH3 H (nt0) J-7 CH H (n=0) J-7 CH 3

H

(no) J-7 CH H (n=o) 3-7 H H (nso) 3-7 H H (ns0) j-7 H H (n=o) J-7 H H (n=O) 3-7 H H (n=0) 3-12 H H

(R

3

=CH

3 3-7 H H 3-7 11 H (r10) 3-7 H H 3-7 H H (n-0) (nuo) 3-7 H

H:

4-7 H

H

(ntio) T-1 Til

CF

3

CF

3

CF

3 .3

CF

3

CF

3

CF

3

CF

3 CH CR 2 CR

OCR

CR2 O 3 C14 OCfl C:1'2 OC-1 Cl2 SH3 CH 3 r

"F

F

CH

3 H 3 CH CN CH CN 2 CH

OCR

CH2 3 CH OCH3 CH2

OCH

CR

C

CH 3 CH 3

CH

3

CH

3

CR

3

CH

3

CH

3

CR

3 SCH 3

CH

3 CH 3

CH

3 CH 3

CH

3 CR4 3

CR

3

K

CH

3 Cl

OCR

3

CH

3 CH3

OCR

3

CHR

3

CH

3

OC

3

C,

OCR

3 OCH 3

CH

3 Ca OC14 3

CR

3

CHR

3 CH 3

CH

3 cll 3 x.-

CH

3

OCH

3

OCR

3 OCR 3

CH

3

OCR

3 OCH 3

OCR

3

CH

3

OCR

3

OCR

3 CH 3

OCH

3 OCR 3 OCR4 3

OC

3

OCH

3 CH 3

OCR

3

OCR

3

CR

3 WO 89/00991 PCT/US88/02459 61 TABLE 1 (continued) 5J-7 H H CH 3CHM 3 Cl 0CM 3 (n=O) J-7 H H CH, CMH OCH OCH 2 5 3 3 3- H C1 H CH 0CH J-7Q HC 2 5 3 3 J-7 H H CM 3CM2H CHM CHM (mn0 3253 J-7 H H CHM 2 H5 clOH3 (n=0) J-7 H CH- nC H 0CH 0CM j 3 3 J-7 Hl 14 CM 3 n-CMH CH 3 C J- H3nC3 H7 CH3 CH3 (n~Q) J-7 H H CH n-CMH C 0CMi (n.Q) J-7 H H CM CM(CM 3 2 0CM 0CH -7 H H CHM 3 CH(CH 3 2 CH 3 0CM J-7 H H CM3C(C CHM 3 CMi 3

C(M)

J-7 H H CHM CHM(,' )2 Cl 0CM 323 J-7 H C~i 3 c 2CF 0 CH 0CM aI H F 0H3 CMi 3 0CM 3-1 H H F CM 3 CH 3 0CH 3 9~ H F Cl 3 cM 3

C

3 CH 3 J-1. H H F CM 3Cl 0cMi J.1 q H CN CH 2CN 0CH 0CM 111111.25 "I1-4 jj 1.6 06SL9I' M ZXMAnsa bdou uIj! ajog o Z~kXMAfIISNd0NWlhrIH0~gn.' ,Ld 01 .25 111111.4____ WO 89/00991 PCT/US88/02459 J-3.

J-7 J-7 (n~o) J-7 (n=0) J-7 (n=O) 3-7 (n=O)j J-7 (n~o) J-7 (n=o) J-7 (n=o) J-7 (n=o) 3-7 (rs=0) J-7 (n=O) E R

H

-H

H

-H

H3 CH3 -CH 3

-H

H

-H

H'E

H

CN CH 2OCH 3 C3 CK2CH2

CH

1 CM CH 20CH3 CH 3 CM 2(CH 2)2 CN CH 2 (CH 2 2 0OCH 3 CH 3 CM H C CH 123 3 CH 3 CM CH 3 CM C 2 C NC H 3 CH 2CN CH3 CH2 N CH3 0CM 3 0CH 3 00H 3 0CM 3 OH 3 Cl OH 3 cl x 00H 3 CCHfi 3 0CH 3 00113 0CM 3 00113 0CM 3 0CH 3

CHM

3 00113 o0i* 3 CH 3 OCH 3 WO 89/00991 PCT/US88/02459 TIABLE2 General Formula 2 31 1 12RRLZ IT J-1 J-1 J-1 J-*1 J-1 a-1a-1 -i J-i a-1 0-1 1 a-i a-1 a-1 d -1 a-1 J-1 a-1 J-i a-i J-i J-1

H

CH2 H CH 3 CH 3 CH 3 CH 3 CH 3 CH3 c2 H5 C 2H5 c2 C n-C 3 CH37 CH37 CH(C3 OCH 3 OCH

H

OCH 3 CH 3 OCH 3 OCH 3 OCH 3 CH 3 OCH 3 OC 2H5 OCH 3 OCH 3 CH 3 OCH 3 OCH

H

OCH 3 OCH 3 OCH 3 OCH 3 OCH 3 OCH 3 NHCH 3 N(OCH 3)(CH4 N(CH 3 2 OCH 3 OC-1 3

NHCH.

N(OCH 3 (CH 3

N(CH,)

OCH 3 OCH 3 NHCH 3 N(OCH 3)' 1 CH3 N(CH3)2 OCH 3 OCH 3 NHCH 3 N(OCH 3 (CH 3 N(CH3)2 CH 3 OCH 3 OCH 3 WO 89/00991 PCT/US88/02459 64 TABLE 2 (Cont'd) B R 12 1 2 J-1 '1 J-1 J-i J-i J-1 J-1 J-1

J-

J-i J-i

"L

J-1 0-i J-1 L-i J-1 J-1 LI-i L-i L-i L-i

H

CH2 H

CH

3

CH

3 L421k

CH

3

CH

3

CH

3

CH

3

CH

3 CzH 2H5 25s

CH

25m CzH n-CH 3H7 n-C H7 n-C H7 n-C H7 n-C H 4 CH(CH cli(CY, 3 2 CH(CH 3 CH(CH 3

CH(CH

CH

3

CH

3

CH

3

CH

3

CH

3 OCH3

OCH

3

OCH

3

CH

3

OCH

3 oc 2H

OCH

3 OCH 3 CH 3

OCH

3 OCH3

CH

3 OCH 3

CH

3

OCH

3 OC H

OCH

3 OCH 3 OCH 3

OCH

3

NHCH

3

N(OCH

3 (CH 3

N(CH

3 )2

OCR

3

OCH

3

NHCH

3 N(0CH 3 (C 3

N(CH

3 2

OCR

3

OCH

3

NHCH

3 N(OCH (CH 3 N(CH3)2

OCH

3

OCH

3

NHCH

3 N(OC 3)(CH N(CH3

CR

3

OCH

3

CH

3 WO 89/ 00991 PCrr/US88/02459 _TABLE 2 (Cont'd) 11 F R RJR 2JILTI j-1 J-1 J-1 J-1 151 J-1 151 3-1 3 -1 3-1 J-1 J-1 0-i 3-i LI-1 J-1

H

CH CH3

CHR

3 N (CH 3 )2 N (CH32 N (CHR )2 N (CH 3)2 N (CH3)2 N (CHR N (CH 3 )2 N (CH32 N (CH32 N (CH 2 N (CH 3 2 N (CH 3)2 N (CH 3)2 LAk CH 3 CH 3 CR 3 CR 3 CH 3 C~mH n-C 3H7 C437 CH(C3 CH(C3 CH 3

OCH

3 oc2 H5 OCH 3 OCR 3 CR 3 OCH 3 OCR 3 OCH 3 CR 3 OCR 3 OCR4 3 OCH 3 CH 3 OCH 3 OCH

H

OCR 3 OCR 3

OCH

3 OCH 3 OCR 3 OCH 3 NHCH 3 N(OCH 3)(CH3 N(CH 3)2 OCR 3 OCR 3 NRCH 3

N(OCH

3

)(CH

3 N(CR OCR 3 OCR 3 N(OCH 3)(CH

N(CR

OCR 3 OCR 3 NHCH 3 N(OCH 3

(CR

3 N(CH 3) CH 3 OCR 3

CHR

3 WO 89/0099 1 F'CT/US88/02459 11 R 12R 1L2 -1 J-1 J-1.

J-1 J-1 J-1 151 -1 J-1 J-.1 20J-1 J-1 J-1 J-1 1 J-1 J -1 J-1

H

H H CH 3 0 CH 3 OCR 3 OCR 3 OCH 3 OCR 3 OCH 3 OCR 3 OCH 3 OCH 3 OCH 3 OCR 3 OCH 3 OCR 3 OCH 3 OCR 3 OCH 3 OCR 3 OCH 3 OCH 3 OCH 3 OCH 3 OCH 3 OCH 3

AUT

CH3 CH 3 CR 3 CH 3 CR 3 C 2H c2 CR2H c2 H5 CR2H n-C 3H7 C37 CH37 CH(C3 CR 3 OCH 3 OCH 3 OCR 3 CR 3 OCR 3 OCR 3 OCR 3 OCH

H

OCH 3 CR 3 OCR 3 OCR 3 OCR4 3 OCR 3 OCR 3 OCR 3 OCR 3 NHCH 3 N(OCR 3 )(CR 3 N(CR )2 OCR 3 OCR 3 NHCR 3 N(OCR )(CR 3 3CH3 OCR 3 OCR 3 N(OC 3 (CR 3 N(CH 3 2 OCR 3 3 3H N(CR 3 2 CH 3 OCR 3 CH 3 WO 89/00991 -CCT)! 1S88102459 67 TABLE 2 (Cont'd) 12 1 X1Z R/R 'ja. Alk -XL.

H1 H 2 HCR CHU OCH CH3 25 o C 3 OH3 O3 J-1 H H OC H C H OCH OCH 2 5 2 5 3 3 H- U H OC CU OCH CH 2 5 2 5 3 3 J-1 F H Br CHU CH 3 ocRi J- C H3 cli3 OH3 J-1 -H H SCN CH 3 CH 3 CH 3 -1H SC 3CH3 O3 C3 J-1 H H SC2H 5CU 3 OClR CHU J- H3 CH3 O 3 CH3 J-1 H U HC 2H CH OCH 3 CR j' H l C C2H5 Q3oii3 C 3 J-.1 U H S(CU CU OCH 3 CU3 25 -1H H N CH2 3H3 CH3 O H3 J-1- H U N(CH 24 CHU C OCH C3 3 3 3 3 N-7HCHH CUi OCR CH3 J-7 U U 25C1 3 OH3 l 3 J-7 U H H(C CHC 3 C OC2H 5 NCH 3 U- U H (CH CH 3 OCH5 CH H U =U 2 3

CUC

WO 89/00991 WO 8900991PCT/US88/02459 TABLE 2 (Cont!dl J1 E 1 R2 J-7 H H (n~o) J-7 H H (n~o) J-7 H H (n=0) J.-7 H H (n~o) J-2 H H J-2 H H J-2 H H j.-2 H H J-2 H H J-2 H H J-2 H H J-2 H H 0.-3 H H 0-3 H H 0-3 H H J-3 H H 0- H H J-3 H H J-3 14H H J-4 H H j-4 H H 2 5 -1 n-C 3

H

7 'CH 3 CM(CH )2

CHM

3 cyclopropyl CH 3 Cl Cl

CN

OCH 3 OH32 N (CH 3)2 Cl Cl

CM

0CH, N (CH )2 N (CH 3 2 Cl C I 0CH 3 OCH 3 0CM 3 0ClM 3 0CH 3 0CH 3 0 CMT 3 0CM 3 0CM 3 0CM 3 0CH 3 0CM 3 0CH 3 OCR 3 CM 3 CH 3

CHM

3 CH 3 0CM 3 OCH 1 CM 3

CHM

3 0CM 3 CH 3 QCM 3 CM 3 0CM 3 0CM 3 CM 3

CHM

3 0CM 3 CM 3 CH3

CHM

3 0CM 3 WO 89/00991 PCT/,JS88/02459 69 TABLE 2 (Gont'd) j IR ELL2 ILL Alk J-4 H H CN CH 3 0GB 3 0GB 3 J-4 H H CN CH 3 OCH 3 GB J4 H H OH3NH3 O 3 CH3 3-4 H H OCH 3 HB OCH GBOH 1 J H H H3 2C 3 Q H 3 C H 3 -5 H H 0GB GB 3 OCH 3 0GRB 3 3 3 H B NH) CHB OCH 3 CH3 2 J- H 14 OH32C 3 OH3 O3 H H N (CHI)2 CH 3 0GB 3

CHB

3 J-7 H B CH GB CHI GBOH 23 3 3 J-7 H B B N GH C 3 0GB 3

C

J-7 B H GN GB 3 0GB 3 0GB 333 3-8 H B HG GB 0GB GBI 3nO 3 33 H B CHG GB OCH 3 CH 3 (n~l) Ir Y I I--ii PCT/US88/02459 WO 89100991 1 2 l Z R R JP j-9 H H (n=o) H H

(H

3

=CH

3 H H R3 C J-11 H H R 3=CH 3) (-12 H 3-C J-12 3 3-CH 3 R =CH 3 J-12 H H

(R

3

=CH

3 J-12 H H

(U

3

CU

3 J-13 H H

(R

3

CH

3 J-12 14 H

(R

3

=C

6

H

5 J-12 H 3 -CU 3 3-11 R H

(R

3

=CH(CU

3 2 H H (R3 =-C 3

H

7 4-11 H H

(R

3

=CH

2

CF

3 3-12 U H

(R

3 =CH 2

CHC)

J-7 U 6-F (n=o) 12z

T/T

H

Cl

CN

Hk

H

Cl

C).

H

cydl cycl

CH

3

H

TABLE 2 (Cont'd) Alk OH 0 H3 CH3

C

CH3

C

CH3

C

CU

C

CH3

Q

CH

3 C CH 3 CH 3 c CH3

C

CH

C

OH~

C

p Copyl R C CH3 c CH3 C CH

C

OH

CH

H

3

H

3

H

3

'OH

3

H

3

)CH

3 CH 3 HC3 H 3 H 33 )CH3 CH3 11 3 :H 3 CH 3

OCH

3

OCH

3

OCH

3

OCH

3 OCU 3

OH

3

OCH

3

OCH

3

CH

3 CH 3

OCH

3 00H 3

I

WO 89/00991 PGT/US88/02459 71 TABLE 2 (Cont t d) I F H ILL T/T Alk _XL 5-1- H 5-F Cl CHCH 3 OCH 3 J-1 H 6-Cl Cl CH 3 OCH CH3 .3-2 H 4-Cl Cl CH 3 0CM 3 0CM J3-7 H 6-Br H CHM 0CM1 0CM (n=Q) J3-1 H 5-Br Cl CHM CH 3 0CM 1 H 3 c H 3 C 3 C R 3 J3-1 H 4-CU Cl CM 3 C 0 CM 3 15J1 H 5O3 CCH3 CH3OC3 .3-1 H 5.-C C3 Cl CH 3 CH 0 CM J1 H 5OF2 H cCH3 CH3 OR3 15-1 H 5-CM Cl CHU CH 3 0CM 3 -1 H 5-SMCl C M CH 30 CMi 3- -C Nc 3 o 32 5 N C 3 .31 -1 H H-C UCl CHM C CHI 0 CM 23 3 .3-1 H 6- Cl C 4 CM OC FCH 0C 3 J-1 H H Cl CH3 3C i 3 O 1 1 H 6-C CM CHM 3 0CM 3 2CH2C CM 3 .3-1 H 6-C CM U CHi 0C OCR 303 25 3 .3-1 U H CN CH C 2a OCCM CM J3-1 H HI Cl CM OCRCE 0CH .3-1 H H Cl CRM OCRCF 0CM WO 89/0099 1 P CT/US 88/02459 72 E 'R 1L.E.

j-1 3-1 J-1 J-1 J-1i J- 1 J-1 J-1 J-1 J-1 J-1 J-1 J-1 -1 J-1 Ji -7 30(4=0) jI-7 J-7

H

Cl Cl Cl Cl Cl C1N Cl Cl

CN

Cl Cl Cl Cl CF 3 Alk CM 3 CH 3 CH 3 CH 3 CH 3 CH 3 CH 3

CHM

3 CH 3 CH 3 CH 3 CM 3 CH 3

CHM

3 C8

CHM

3 CH 3 OCH 2CHF2 OCH 3

OCM

CH 2F oc2 CF 3 OCH

F

CM 3 CM 3 0CM 3 CH 3

OCH

CI,:

,2 0CM 2 CF 3 CM 3

CECH

2C 3 2 32

QCC

3 CH

C

3 2C

CM

3 2 H2

C

OCH 3 25 3 NC 3 0CMCH

CM

H H

H

H H H H CF 3

CF

CF 3 CF3 c2 H5 OH3 H3 WO 89/00991 WO 8900991PCT/US88/02459 I E 'R'12R J-7 H H (n=0) J-7 H H (n=O) J-7 H H (n=0) 3-7 H H (n=0) J-7 H H (n=0) 0-7 Hl H (n=O) J-7 H H (n=0) J-7 H Hi (n=O) 2 3 -7

H

(n=Q) 3-7 H H (n=Q) J-7 H H (n=0) J-7 H U (n~o) 0-7 H H (n-0) J-7 H I- I (n;0) J-7 0 H J-11t H U

(R

3 =CH 3) 3-1 R 1H TABLE 2 (Contid) 1 2L Alk

X

CF 3 C 21 CH3 C3 325 7 C 3 CF 3 n-C 3H 7 CH3 CF3 372 N C 3 CF nC C CH3 CF3 37i 23N O CF 3 CHU CN OCH 3C CF3 CH2 OH Q 3 CF 3 CH2 CH CH3 3H 2 C C 3 CFlzOC CHC1 3 OcHi 3 2H 2 5ci F CH C3 CH CF CH3 C 3 C 33 CH3 2H 3 c2 CU 3C- CH 3 Oc CF CH2 SH3 CH3 OH3 OCH 3 OCH 3

OCHI

OCH 3

NHCU

3 N (CH 3 2

OC-I

3 OC14 3

OCH

OCU

3

OC-I

OCU

3

N(CH

CHU

3 ocli 3 OCH 3 WO 89/00991 PCT/US88/024.5-9

TABL~~

31 Fa J.-7 (n=o) J-J11- R 3= CH 3 12LR CH CN CH 3 CIH 3C CH3 C2 SH3 CH3

OCH

3 WO 89/00991 PCT/US88/02459 J E R R 1/R 2 T 1/T 2 Alk X, Y J-1 H H Cl CH 3 CH J-1H clCH3 1J-1 H H Cl CH 3 OCFH 0 J- H H N H3 CH3 J H H Cl Cil OCH 3 0 -1 HOC 3 CH3 253 J- H H Cl CH 3 CH 0 J-3 H H Cl C H 3 CH 3 0 J-12 H 3-H 3 CN H CH C3 0 J.-7 H H CH CHI 3 CH J-7 H HF H CH 3 CH J-1 P 5-00 H Cl CH C H, 0 J-1 H 6 Cl CN H CH 0 J-12 H I 3-.CH ClH CH 3 CH 0 3 =CH 3 )3 J.-1 CH HI H1 H CII CI 0 253 3 -1 CH 6 C HCN CH3 CH WIO 89100991 PCT/US88/02459 TABLE 3 3 E R R I/R2 J-7 H H J-7 H H (n=O) 1 3 -7 H H (n=O) 10J-7 H- H (n=O) T /T 2 Alk X ii F CH 3 CH3 F

C.H

3 CH3 CF CH 3 CH3 CH 3 CH 2CN OCH3 CH 1 CH 2OCH 3oc.H -mm WO 89/0(1991 PCT/US88/02459 a E a-i J-2 J-3- J-12 Ji-7 (n=o) J-7 (n=O) J-1 J-1 J-12 R 3

CH

3 J-1

CH-I

2 J-1 a-1 J-7 (n~o) J-7 (n=O) R R 1/R2 H H H H H H H 14" H h, H H H H H H Ti H H 3-CU 3 era rmuaA T 1/T 2 Alk Cl CH 3 Cl CH 3 Ci CH 3 cl

CHR

3 CN

CH

CN CH 3 OCH 3 CH3 Cl Cl-I 3 Ci CH 3 Cl CH 3

L

CHR

3 OCH 3 OC OCF 2H

CHR

3 OCH 3 CH 3

CHR

3 O-H3

CH

H H OCR 3 H 6-F H 5 -OCR R 6-Cl H 3 -CiT 3 H H CR H H H H H H H CR 3 CR 3 C

R

CH 3 CR 3 CR 3

OCYR

3

OCR

OCR 3 CR 3 CR CNq WO 89/00991 pCT/U ;388/02459 TAB LE T I/T 2 Alk 3 E R R I/R2 J-1 J-1 J-1 J-1 J-2 J-3 J-12

(R

3 CH 3 J-7 (n=0) J-7 (n=0) J-1 J-12 (R 3=CH 3-i CM 2 J-1 ji-1 3-1.

J-7 (n=O} J-7 (n~o) J-7 (n=0) H H H H H H H H H H H H H H- H H 17 H HI 3-CM 3 CH 3 OC OCF 2H CH 3 CH 3 OCH 3

CHM

3 H H OCH 3

CHM

H 6-F 5-0CM 3 63-CM 3 CH 3 0CM 3 OC" 3 CH 3 0CM 3 0CM 3 OCH 3 0CH 3 OCR 3

CN

Cal

F

H H H H OH3 CH3 CV1I CN 0CM

CM

WO 89/00991 WO 8900991PCT/US88/02459 J R R 1/R2 J-1 J-1 J-1 J-1 J-1 J-1 J-1

J-'

J-1 J-1 (n=0) J-1

CHR

2 J-2 J.-3- (3=CH 3) J-12( R 3 CH 3 1 c-7 (n=o) J-7 3 (n=O) General Formula 6 T 1/T 2 Alk X Cl CR

CR

cCH3 CH3 Cl CHR CH3 cCH3 CH3 Cl CR

CR

cCH3 CH3 Cl CR 3 C cl CH3 C2F3 Cl CR CH3 OC H3 CH3 H H3 CH3 OCR 3 SCH

R

CR 3

OCR

OCR 3 OCR 3 OCR 3 OCR 3 OCR 3 OCR 3 OCR 3 OCR 3 OCR 3

R

H

R

3 -CU 3 CR 3 CR 3 CH 3 CR 3 CR 3 H H Cl CR 3 C3 OH3 3 6-Cl 6-F CR 3 CR 3 CR 3 CR 3 OCR 3 OCRi 3 OCR 3 OCR 3 H H J-7 (n=0) H H CR CN CR

OCR

WO 89(0099 1 PCT/US88/02459 TABLE 7 General Formula 7 0 E R R 1/R 2 T 1/T 2 Alk X3 -1 H H Cl CH 3 CHR 0-1 H H Cl CH 3 OCR J-1 H H CN CH CH3 100o -1 H H CN CR 3 OCR 3 0-1 H H OCR CR OCR 3 J-2 H H Cl CH 3 CH3 J-3 H H Cl CR CR J-4 H H Cl CR 3 OCR 3 H F1 H CR CR J-7 H H H CR OCR (n=0) J-12 H H H CR OCR R 3 =CH 3 )3 J-7 H 6-F 14 CR OCR (n=0) 0-1 H 6-Cl CN CR OCR 250-12 H 3-CR H CR CR 25(R 3

=CHR

3 0-1 H 5-OCR 3 Cl CR CR 0-1 CR H H CN CR CR 0-1 CH 3 H Cl CR CH 0-7 H H CR CR CR 3 (n=0) J-7 H H CF 3 CR CHR 3 (11=0) k7- H H CR CHR2CN CR 3 WO 89/00991 WO 8900991PCT/US88/02459 General Formula 8 J E R R1/R 2 T I/T 2 Alk X4 Y4 Zl J-1 J-1 J-1 J-1 J-1 J-1 J-1 J-1 J-1 J-1 J-1 j-1~ J-1

CH'

2 J-1 J-2 Ji-3 J-4 j-7 (n0o) J-12

R

3 CH 3 CH 3 CH 3 CH 3 CH 3 CH 3 CH 3 CH 3 CH 3 CH 3 CH 3 CH 3 CH 3 CH 3 CH 3 CH13 CH 3 CH 3 CH 3 CH 3 CH 3 CH CHN O3 CH3C CH 3 CHl3 N O3 O3 C 3l C 3 C OCH 3 Cl CNI 3c2H5 C 3 C 0CH 2 OH3CH ClN OH3 CH3 C OCl' 3 CH N C OH3 CH3 C OCH 3 CH 3 CH 25 3 C 3 C CHOCH Cl' NC OCH 3 CH N C H H H' Cl' 3 H 6-F H CH 3 J-7 (n=o) WO 89/00991 PCT/US88/02459 J E J-12 R 3=CH 3 0-1 J-1 J-7 (n=O) J-7 (n~o) J-7 (n=Q) J-7 (n=O) R 1/R2 3 -CH3 S-OCH 3 6-Cl

H

TABLE 8 (Cont'd) V~ /T

H

Alk

CHE

3 CH 3 CH 3 CH 3 CH 3 CH 3 CH CN CH 3 -4

OC

H 3 OCH 3 OCH 3 OCH 3 OCH 3 OCH 3 OCH 3 OCH 3 Y4 CH 3

CHE

3

CHE

3 CH 3 CH 3 CH 3

CHE

3 CH 3 WO 81400991 WO 8~OO991PCT/US88/02459 TABLE 9 J E R R I/R 2 T 1/T 2 Alk J-1 J-1 J-1 J-1 J-1 J-2

J-

J -4 J-1 J-1 J-7 (n~o) J -7 (n±o) H H Cl H H Cl H H Cl H H CN CH H Cl CH 2 H H CN H H Cl H H Cl H H Cl H 5-OCX Cl H 6-Cl CN H H

CHX

3 H H CF3 CH

I

CH 3 CH 3 CH 3

CHU

3

CH

CHU

3 CH 3

CHU

3 CH 3 CH 3 w X4 Y4 !I S OCH OCX CX s H3 OH3 N S C OCH N S O3 OH3 C S OCH 3 OCX N C s CH3 OH3 C s OCX OCX CX s CH3 OH3 C S OCX OCX CH s CH3 OH3 C S OCX OCX CH S OCX OCX CX S OCX OCX, CH (n=O) WO 89/00991 PCT/US88/02459 84 Formulations Useful formulations of the compounds of Formula I can be prepared in conventional ways. They include dusts, granules, pellets, solutions, suspensions, emulsions, wettable powders., emulsifiable concentrates and the like. Many of these may be applied directly. Sprayable formulations can be extended in suitable media and used as spray volumes of from a few liters to several hundred liters per hectare. High strength compositions are primarily used as intermediates for further formulation. The formulations, broadly, contain about 0.1% to 99% by weight of active ingredient(s) and at least one of these carriers: about 0.1% to 20% surfactant(s) and about 1% to 99.9% solid or liquid inert diluent(s). More specifically, they will contain these ingredients in the following approximate proportions: Weiaht Percent* Active Inqredient Diluent(s) Surfactant(s) Wettable Powders 20-90 0-74 1-10 Oil Suspensions, 3-50 40-95 0-15 Emulsions, Solutions, (including Emulsifiable concentrates) Aqueous Suspension 10-50 40-64 1-20 Dusts 1-25 70-99 Granules and Pellets 0.1-95 5-99.9 0-15 High Strength 90-99 0-10 0-2 Compositions Active ingredient plus at least one of a Surfactant or a Diluent equals 100 weight percent.

B

WO 89/00991 PCT/US88/02459 Lower or higher levels of active ingredient can, of course, be present depending on the intended use and the physical properties of the compound. Higher ratios of surfactant to active ingredient are sometimes desirable, and are achieved by incorporation into the formulation or by tank mixing.

Typical solid diluents are described in Watkins, et al., "Handbook of Insecticide Dust Diluents and Carriers", 2nd Ed., Dorland Books, Caldwell, New Jersey, but other solids, either mined or manufactured, may be used. The more absorptive diluents are preferred for wettable powders and the denser ones for dusts. Typical liquid diluents and solvents are described in Marsden, "Solvents Guide", 2nd Ed., Interscience, New York, 1950, Solubility under 0.1% is preferred for suspension concentrates; solution concentrates are preferably stable against phase separation at 0°C. "McCutcheon's Detergents and Emulsifiers Annual", MC Publishing Corp., Ridgewood, New Jersey, as well as Sisely and Wood, Encyclopedia of Surface Active Agents", Chemical Publishing Co., Inc., New York, 1964, list surfactants and recommended uses. All formulations can contain minor amounts of additives to reduce foaming, caking, corrosion, microbiological growth, etc, The methods of making such compositions are well known. Solutions are prepared by simply mixing the ingredients. Fine solid compositions are made by blending and, usually, grinding as in a hammer or fluid energy mill. Suspensions are prepared by wet milling (see, for example, Littler, U.S. Patent 3,060,084). Granules and pellets may be made by spraying the active material upon preformed granular carriers or by agglomeration techniques, S4 J. E. Browning, "Agglomeration", Chemicgrl;tineerng, December 4, 1967, pages 147ff. and "Perry's Chemical Engineer's Handbook", 5th Ed., McGraw-Hill, New York, 1963, pages 8-57ff.

~3b (n=0) WO 89/00991 PCT/US88/02459 86 For further information regarding the art of formulation, see for example: H. M. Loux, U.S. Patent 3,235,361, February 15, 1966, Col. 6, line 16 through Col. 7, line 119 and Examples 10 through 41; R. W. Luckenbaugh, U.S. Patent 3,309,192, March 14, 1967, Col. 5, line 43 through Col. 7, line 62 and Examples 8, 12, 15, 39, 41, 52, 53, 58, 132, 138 to 140, 162 to 164, 166, 167 and 169 to 182; H. Gysin and E. Knusli, U.S. Patent 2,891,855, June 23, 1959, Col. 3, line 66 through Col, 5, line 17 and Examples 1 to 4; G. C. Klingman, "Weed Control as a Science", John Wiley and Sons, Inc., New York, 1961, pages 81 to 96; and ci. D. Fryer and S, A. Evans, "Weed Control Handbook", 5th Ed., Blackwell Scientific Publications, Oxfor~d, 1968, pages 101 to 103.

In the following examples, all parts are by weight unless bherwise indicated, Example Kigb Stizexigth Concentrate 2 -[t[(4-ch~oro--methoxy,2-pyrimidinyl).

arninoJcarbonylj aminoj sulfonyli -NmethoxybenzenecarbQximidQyl chloride 99% trimethylnonyl polyethylene glycol ether 1% The surfactant is sprayed upon the active ingredient in a blender and the mixture sifted through a US.S. No. 40 sieve (0,42 mm openings) prior to packaging, The concentrate may be formulated further for practical use.

WO 89/00991 PCT/US88/02459 87 Wettable Powder 2-t(cyano) (methoxyimino)rnethyl].-N- [[(4-me-thoxy-6-methyl-2-pyrimidinyl)amino) carbonyll benzenesulfonanide dodecyiphenol polyethylene glycol ether 2% sodium ligninsulfonate 4% sodium silicoalurninate 6% rnontmorillonite (calcined) 23% The ingredients aro, thoroughly blended. The liqu~id surfactan~t is added by spraying upon the grlid ingredients in the blender. After grinding in a hammer mill to produce particles essentially all below 100 microns, the material is reblended and sifted through a U,S.S. No. 50 sieve (0,3 mm opening) and packaged.

AqueQugs Suspension N-methoxy-2-( [(II(4-methoxy-6-.methyl- 1,3, 5-triazin-2-yl' nminojcarbonyllarr no) ISul fonyl Ibenzeneca rboximi doyl chloride

O%

polyacrylic acid thickener 03 dodecylphenol polyethylene glycol ether 0.45% disodium phosphate monosodium phosphiate Polyvinyl alc2ohol water $6.7% WO 89/00991 PCT/US88/02459 88 The ingredients are blended and ground together in a sand mill to produce particles essentially all under 5 microns in size.

Example 13 Oil Suspension 2-[I[[(4-chloro-6-methoxy-2-pyrimidinyl)amino)carbonyl]amino]sulfonyl]-- methoxybenzenecarboximidoyl chloride blend of polyalcohol carboxylic esters and oil soluble petroleum sulfonates 6% xylene 59% The ingredient,- are combined and ground together in a sand mill to produce particles essentially all below 3 microns. The product can be used directly, extended with oils, or emulsified in water.

Example IA oil susnn. iQn 2-C(cyano)(methoxyimino)methyl]-N- C (4-methoxy-6-methyl-2 -pyrimidinyl)aminolcanonylJbezenesulonanide polyoxyethylene sorbitol hexaoleate highly aliphatic hydrocarbon oil k The ingredients are ground together in a sand mill until the solid particles have been reduced to under about 5 microns, The resulting thick suspension may be applied directly, but preferably after being extended with oils or emulsified in water, 1 WO 89/00991 PCT/US88/02459 89 Example Agueous SuspensioQn N-methoxy-.2-' r[(4-methoxy-6-methyl- 1, 3, 5-t ri azin-2-y:l),amino carbonyl]I aminolsulfonyl]bcrnzenecarboximidoyl chloride 25.0% hydrated attapulgite crude calcium ligninsulfonate 20.0% sodium dihydrogen phosphate water 61.5% The ingredients are ground together in a ball or roller mill until the solid particles have been reduced to diameters under 10 microns, ExiimPle 16 Wettable Powder 2-V !([(4-chloro-6-rnethoxy-2-pyrimidinyl)aminojca&bonyl] aminojsulfonyl]-Nmethoxybenzenecarboximidoyl chloride dioctyl sodium sulfosuccinate sodium ligninsulfonate 3 low viscosity methyl cellulose 115% 54% The ingredients are thoroughly blended, passed through an air mill, to produce an average particle size under 15 microns, reblended, and sifted throught a U,S. No. 50 sieve (0.3 mm opening) before pack.egin All1 compounds of the invention may be formulated in the same manner.

WO 89/00991 PCT/LJS88/02459 Examnle 17 Granule wettable powder of Example 16 gypsum 69% potassium sulfate 16% The ingredients are blended in a rotating mixer and water sprayed on to accomplish granulation. When most of the material has reached the desired range of 1.0 to 0.42 cm No, 18 to 40 sieves), the granules are removed, dried, and screened. Oversized material is crushed to produce additional material in the desired range. These granules contain active ingredient.

Exatajmle 18 WettablQ Powder 2-[(cyano) (methoxyimino)methylj-N- [[(4-mef-hoxy-6-methyl-2-pyriridinyl)aripnolcarbonyllbenzenesulfonamide sodium alkylnaphthalenesulfonate 2% low viscosity methyl cellulose 2% diatomnaceous earth 46% The ingredients are blended, ooarsely hammwr-rnillecl and then air milled t produce particles of active essentially all below 10 microns in diameter. The product is Veblended before packaging, Examole 19 Extruded Pellet N-methoxy-2-( F((4-methoxy-6-methyl- 301,3, 5-triazin-2-yl) amino) carbonyl] aminrosulfonylbenzenecarboximidoyl chloride J-7 H H CH 3 CH2CN OCH 3

I

WO 89/00991 PCT/US8S/02459 91 anhydrous sodium sulfate crude calcium ligninsulfonate sodium alkylnaphthalenesulfonate 1% calcium/magnesium bentonite 59% The ingredients are blended, hammer-milled and then moistened with about 12% water. The mixture is extruded as cylinders about 3 mm diameter which are cut to produce pellets about 3 mm long. These may be used directly after drying, or the dried pellets may be crushed to pass a U.S.S. No. 20 sieve (0.4 mm openings). The granules held on a U.S.S. No, 40 sieve (0.42 mm openings) may be packaged for use and the fines recycled.

Example Wettable Powder [[[(4-chloro-6-methoxy-2-pyrimidinyl)amino]carbonyllamino]sulfonyll-Nmethoxybenzenecarboximidoyl chloride sodium alkylnaphthalenesulfonate 2% sodium ligninsulfonate 2% synthetic amorphous silica 3% kaolinite 13% The ingredients are blended and then ground in a hammer-mill to produce particles with an average particle size less than 25 microns in diameter. The material is reblended and sifted through a U..S.S No. 50 sieve (0.3 mm opening) before being packaged.

J-7 H H CH, CH2CN OCH CH 2 3 3 WO 89/00991 PCT/US88/024i9 92 Example 21 High Strength Concentrate (cyano) (methoxyimino)methyl]-N- [[(4-methoxy-6-methyl-2-pyrimidinyl)amino]carbonyl]benzenesulfonamide 98.5% silica aerogel synthetic amorphous fine silica The ingredients are blended and ground in a hammer-mill to produce a high strength concentrate essentially all passing a U.S.S. No. 50 sieve (0.3 mm opening). This material may then be formuated in a variety of ways.

Utility Test results indicate that the compounds of the present invention are highly active preemergent or postemergent herbicides or plant growth regulants.

Many of them have utility for broad-spectrum preand/or postemergence weed control in areas where complete control of all vegetation is desired, .uch as around storage tanks, industrial storage areas, parking lots, drive-in theaters, around billboards, highway and railroad structures. Some of the compounds have utility for selective weed control in crops such as rice, wheat, barley, corn, sorghum, soybeans and cotton. Alternatively, the subject compounds are useful to modify plant growth.

The rates of application for the compounds of the invention are determined by a number of factors, including their use as plant growth modifiers or as herbicides, the crop species involved, the types of weeds to be controlled, weather and climate, u-l (n=0) H H CH CN CH 3 2 3

OCH

3 psi WO 89/00991 PCT/US88/02459 formulations selected, mode of application, amount of foliage present, etc. In general terms, the subject compounds should be applied at levels of around 0.001 to 20 kg/ha, the lower rates being suggested for use on lighter soils and/or those having a low organic matter content, for plant growth modification or for situations where only short-term persistence is required, such as a herbicide for fallow land.

The compounds of the invention may be used in combination with any other commercial herbicide, representative examples of which are those of the sulfonylurea, triazine, triazole, uracil, urea, amide, diphenyl ether, carbamate, imidazolinone, cineole and bipyridylium types. A partial listing follows: WO 89/00991 WO 89/099 1PCT/US88/02459 Common Name acetochior acifluorfen acrolein alachlor ametryn am it role

AMS

lam atrazine barban benefin bensulfuron methyl bensulide bentazon benzofluor Chemical Name 2-chloro-N- (ethoxymethyl) (2-eth 'l-6methylphenyl) acetarnide 5- r2-chloro-4-(trifluoromethyl)phenoxyj- 2-nitrobenzoic acid 2-propenal 2-chloro-N-(2,6-diethylphenyl)-N-(methoxymethyl) ace tamide N-ethyl-N' C -methylethyl )-6.-(methylthio)- 1,3, 5-triazine-2 ,4-diamine 111-1, 2,4-triazol-3-amine ammnonium sulfanmate methyl [(4-aminophenyl)sulfonyljcarbamate 6-chloro-N-ethyl-N' -(l-methylethyl)-1,3,5triazine-2, 4-diamine 4-chloro-2-butynyl 3-chlorocarbamate N-butyl-N-ethyl-2, 6-dinitro-4-( trifluoromethyl )benzenami ne 2-[f t[4,6-dimethoxy-2-pyrimidinyl)amino]carbonftj amino) sulfonyl )methyljbenzoic acid, methyl ester O,Q-bis(2.-methylethyl) S-42-f (phenylsulfonyl)amino~lethyl] phosphorodithioate 3-(l-methylethyl)-(lH)-2,l,3-benzothiadiazin-4(31i)-one, 2,2-dioxide N-[4-(ethylthio)-2-(trifluoromethyl)phenyl jmethanesulfonamide N-benzoyl-N- 4-dichlorophenyl )-DLalanine methyl 5-(2,4-dichJlorophenoxy)-2.

ni trobenzoate 5-bromo-6-methylN3-.( -methylpropyl) 2, 4(1H, 3H)pyrimidinedione benz oylp rop bifenox WO 89/00991 WO 89/099 1PCT/US88/02459 Common Name bromoxyni].

butachior buthidazole butralin butylate c acodyli c acid

CDAA

CDEC

chioramben chlorbromuron chl2or im iron ethyl chia roxuron chlorpropham cbiorsulfuron chlozrtoluron cinmethylJin clethodim Chemical Name 3, 5-dibromo-4-hydroxybenzonitrile N-(butoxymethyl)--2-chloro-N-12, 6-diethylphenyl )acetaxnide 3-[5-(l,l-dimethylethyl) -1,3,4-thiadiazol-2-yl )-4-hydroxy-l-methyl-2iidazolidinone 1, 1-dimethylethyl 1-methylpropyl) 6-dinitrobenzenamiine S-ethyl bis(2-methylpropyl)carbamothioate dimethyl arsinic oxide 2-chloro-N~,N-di1-2-propenylacetanide 2-chloroallyl diethyldithiocarbamate 3-amino-2,5-dichlorobenzoic acid 3-(4-bromo-3-chlorophenyl )-l-methoxy-lmethylurea 2-ft t (4-cbloro-6-methoxy-2 -pyrimidinyl) axinojcarbonyl Iamino] sulfonyl Jbenzoic acid, ethyl ester N' -[4-(4-chlorophenoxy)phenyl)-NNdimethylurea )1-methylethyl ?-chlorophenylcarbamate 2-chloro-N- 4-mqthoxy-6 -methyl-1, 3, triazin-2-yl) amino) carbonyl. benzenesulfonamide N' -(3-chloro-4-methylphenyl) -N,Ndimethylurea exo-l-methyl-4-(N-methylethyl) -2-f(2methylphenyl )methoxy) -7 -oxabicyclo- [2.2,1jheptane (E.E)-()-2-[l-[f(3-chloro-2-propenyl)oxy~imino~propylj -5-t2-(ethylthio) propyl I-3-hydroxy-2-cyqlohexen-l-one WO 89/00991 WO 8900991PCT/US88/02459 Common Name Chemical -Name clomazone cloproxydim cl1opyr ali d

CMA

cyanazine cycloate cycluron cyperquat cyprazine cyprazole cypromid dalapop dazomet

DCPA

desmediphan desmetryn diallate dichlobenil 2- [(2-chiorophenyl )rethyl]-4l,4-dimethyl- 3-isoxazolidinone (E,E)-2-[l-[[(3-chloro-2-propenyl)oxy)imino]butyl]-5-[2-(ethylthio)propyl]- 3 -hydroxy-2 -cyclohexen-l-one 3, 6-dichloro-2-pyridinecarboxylic acid calcium salt of MAA 2-f [4-chloro-6-(ethylamino)-l,3,5-triazin-2-yl 1amino) -2-niethyipropanenitrile S-ethyl cycqlohexylethylcarbamothioate 3 -cyclooctyl-I -dimethylurea 1-methyl-4-phenylpyridinium 2-chloro-4-( cyclopropylanino) isopropylamino) triazine thiadiazol-2-ylJ cyclopropanecarboxami de 3' ,4 -dichlorocyclopropanecarboxanilide 2,2-dichloropropanoic acid tetrahydro-3,5-dimethyX.-2H-1,3,5-thiadiazine-2-thione dimethyl 2, 3,5, 6-tetrachloro-l, 4-benzenedicarboxylate ethyl t(phenylamino)carbonyl]oxyjphenyl ]carbamate 2-(isopropyJlarino)-4-(methylamino) -6- (methylthio) -g-triazine 3-dichloro-2-propenyl)his(lmethylethyl )carbamothioate 3, 6-dichloro-.2-rethoxybenzoic acid 2, 6-dichlorobenzonitrile WO 89/00991 PCT/US88/02459 Cgpmmon NaMe di chlorprop Chemical Name di chlo fop diethatyl difenzoguat dinitranine dinoseb di phenamid dipropetryn diquat diuron

DNOC

DPX-M5,116

DSMA

endothall

EPTC

ethalfluralin 2,4-dichlorophenoxy)propanoic acid 4-dichliorophenoxy)phenoxyJpropanoic acid N- (chioroacetyl) 6-diethyiphenyl) glycine 1, 2-dirnethyi.-3,

N

3

.N

3 -diethyl-2, 4-dinitro-6-(trifluoromethyl) 3-benzenediamine 2-(l-methylpropyl) 6-dinitrophenol N,N-dimethyl -ca-phenylbenzeneacetamdde 1,3, 5--riazine-2, 4-diamine 6,7-dihydrodipyrido(l,2-a;2',l'-c]pyrazinedium ion 3,4-dichlorophenyl)-N,N-dimethylurea 2-rnethyl-4, 6-dinitrophenol 3-1 E (4-methoxy-6-metbyl-1,3,5-triazinaminojoarbonyijaminol sulfonyll- 2-thiophenecarboxylic acid,, methyl ester disodium salt of MAA 7-oxabi.cyclo(2. 2.llheptane-2, 3-dicarboxylic acid S-ethyl dipropylcarbarnothioate N-ethyl-u I2-methyl2-propeuiyl)-2,6dinitro-4 (trifluromethyl)benzenamine WO 89/00991 WO 8900991PC-r/US88/02459 ethofumesate Chemical Name Express@ fenac (±)-2-ethoxy-2, 3-dihydro-3, 3-dimethylmethanesulfonate 4-methoxy-6-methyl-l, 3, 2 -yl) -N-methylaino) carbonyl] amino) sulfonyl]benzoic acid, methyl ester 2,3,6-trichJlorobenzeneacetic acid (6-chloro-2-benzoxazolyl)oxy)phenoxy)propanoic acid N,N-cdimethyl-NI-phenylurea Salt of fenuron and TCA fenoxaprop fenuron fenuron TCA flaxnprop fluazifop f luazi fop-P flu chl oral ix fluometuron fliioroch2.oridone fluorodifen O~uoroglycofen flurido-,ie fomesafen N-benzoyl-N- (3-chloro-4--fluorophenyl) DL-al anifle (.±)-2-.14-t[5-(trifluoromethyl) -2--pyridinyl]oxy)phenoxylpropanoic acid (R)-2-.4-((5-(trifluoromethyl)-2-pyridinyl]oxyjphenoxyjpropanoic acid 2-chloroethiyl)-2, 6-dinitro--N-propyltrifluoromethyl)benzenanine N,N-dimethyl-N' -[3-(trifluoromethyl)phenyl 11urea 3-chloro-4-(chloromiiethyl)-I-3.I(trifluoromethyl )pienyl J-2-pyrrolidinone ~-nitrophenyl ca,mctc-trifluoro-2-nitrop-tolyl ether oarboxymethyl 5-f2-chloro-4-(trifluoromethyl )phenoxy) -2-nitrobenizoate l.-methyl--3-phenyl--f3-( trifluoromethyl) phenyl J-4 (lH) -pyridinone 5- (2-chloro-4-( trifluoromethyl)phenoxy] N-(methylsulfonyl -2-nitrobenzamide carriers or by agglomeration techniques. Se~ J. E. Browning, "Agglomeration" Chemic1 j__nqineerina, December 4, 1967, pages 147ff. and "Perry's Chemical Engineer's Handbook", 5th Ed., McGraw-Hill, New York, 1963, pages 8-57ff.

WO 89/0099 1 Common Name fos amine glyphosate haloxyfop hexaflurate hexazinone imazaniethabenz PCT/US88/02459 99 Chemical Name imazapyr imazaquin ethyl hydrogen (aminocarbonyl)phosphate N-(phosphonomethyl) )glycine [3-chloro-5.-(trifluoromethyl)-2pyridinyl~oxy)phenoxy]propanoic acid potassium hexafluoroarsenate 3-vyclohexyl-6-(dimethylamino) -1-methyl- 6-(4-isopropyl-4-methyl-5-oxo-2imidazolin-2-yl)-ff-to'1uic acid, methyl ester and 6-(4-isopropyl- 4-rnethyl-5-oxo-2-imidazolin-2-yl) p-.toJluic acid, methyl ester~ 5-dihydro-4-methyl-4--(1-methylethyl) -5-oxo-lH--imidazcl"2_yI] -3pyridinecarboxylic mcid 5-dihydro-4-methyl-4-(l-methylethyl) -5-oxo-1H-imidazol 2-yl 3-3quinolinecarboxylic acid 5-diJhydro-4--methyl-4-( l-methylethyl-.3-pyridinecarboxylic acid 4-hydroxy-3, cupropylberzqnamine N- (4-t opropylphenyl 14N N ',dime thyl ure a N' l-d1imethyJlethyl) -3-isoxazolyl)j- N,N-dimethylurea i~oxazoly1 j-2, 6-dimethoXybenzamide 3[(dimet~hylamino)carbonyljamino)phenyJ.-(1, 1-dimethylethyl)carbamate imazethapyr ixynil isopropalin isoproturon is. Kaben karbutijlate 2 1, WO 89/00991 WO 8900991PCT/US88/02459 100 Common Name Chemical Name lactofen lenacil 3.inuron (.±)-2-ethoxy-l-methyl-2-oxoethyI 5-122chloro-4-( trifluoromethyJ.)phenoxy]- 2-nitrobenzoate 3-cyc3.ohexcyl-6, 7-dihydro-lH-cyclopentapyrimidine-2..4(3H, N '-(3,4-dichioroplieny))-N-inethoxy-Nme thylure a methylarsonic acid

MAMA

MCPA

monoammoniwii salt of MAA

MCPB

mecoprop inefluidide (4-ch3oro-2-methylphenoxy)acetio acid 4-.(4-chloro-.2-methylphenoxy-) butanoic acid (.±)-'Z-(4-chlozro-2-nethylphenoxy) proparloic acid N-[2,.4-dimethyl-.51 Iitriflaoromethyl)ev3.fonyl )am~nojphenyl.iaqetanid N-(2-mnethyl-2-propenyl)-2Z 6-cinitro-Npropyl-4-( trifluoromethyl )benzeziamide 1, 3-dimethyl-3-(-benohiazolyl)uirea methalprop aliri methabenzthlazuron me tham methazole methyarbamoditthloic ac~id methaxtiron 2-(3,4-dichlorophenyl)-4-methyl-1#2,4oXadiazo~idIne-3, -divine N' -(3-chloro-4-methoxyphenyl diinethyluren 2 -chloro-N- (2 2-ethyl -O-methylphenyl) metolachlor WO 89/00991 WO 8900991PCT/U588/02459 Common Nameq metribuzin methyl molinate monolinuron monuron

TCA

MSMA

napropamide naptalan neburon nitralini 2 5 nitrofen nitrotluorfen Chemical Name thio)-1, 2,4-triazin--5(4H)-one azin-.2-yl) amino]carbonyl]aminojsulfonyljbenzoic acid, methyl ester 1, 2-dihyclro-3 ,6-pyridazinedione S-ethyl hexahydro-IHI-azepine-l-carbothioate 3-.(p-chloropheny -l-methoxy-]-methylurea

N

t -(4-chlorophenyl) -N,N-dimethyJlurea Salt of monuron and TCA monosodium salt of MMA NN-dje thyl-2,-(1-n-aphthalenylpxy) propanaudlcl 2-f -naphthalenyl amino) cArbony2Jbenzoic acid l-butyl-3-( 3 ,4-dichlorophenyl) -1-methylurea dipropylaolline 2, 4-dichloro-1-( 4-zitrophenioxy)bernzene fluoromethyl.) benzene N, NImethyl.-N' -(octahydro-4,7 -meiI~ano- 32 4nden-.5-yl)urea 3ac.,- 4ca,5o~e7c( 7aa-i.somer 4-dhloro -5-(methylamlno) itluoromethyl) phenyl) -3 2f) -gyridzinone 4- (dipropylamino) -3 benzenesultonamide horfJlurazon oryzalin

L~.

WO 89/00991 PCT/US88/02459 102 _Qbh mical Name oxadiazon oxyfluorfen Varaquat pebulate pendimethe'.iin perfluidone phenme diphai pil1or am PPG-1O13 3-.f2, 4-dichloro-5-( 1-rethylethoxy) 1, 3, 4-oxadiazol-2 (3H) -one 2--chlor---( 3-ethoxy-4-nitrophenoy)-4- (trifluoromethyl.)benzene 1..1'-dirnethyl--4,4 '-dipyridiniun ion P-propyl butylethylcarbamothioate 1-ethylpropyl dimetiyl-2, 6dinitrobenzenamIine sulfonyl )pheT4' jmethanesulfonamide 3- (methoxycarbonyl) amino )phenyl (3rnetbylphenyl) cazrbaniate 4 -amino-3,5,6-trichloro-2-pyr'4dinecarboxylilc acqid phenoxy) -2-nltroagatophenone oximp-0-acettc, acid, me~thyl ester 2-,((4-qhloro-6-(cyclopropy1lniino)-1 triazine-2-yl I amino]3 -2-rnethylprpanenitrile N- (cyclopropylmethyl) din ro-Npoy- (trifjuoromethy!)benzenamine 6-methoxyN,N-bi(I-mettkqlethyl)-t,3,$tri3zin-2,4la in am2, ie in 3,o -dichloro--(1, dethy-2o~propynyi )bonzamiide phenylaoetide N4 4 -a Ohio rophienyl p ropananide 1# S 5triazine42,4-diamnd pz'ocyaz, ne profluzralin prometon prornetryn pronamide propachlor 3 pzropatkil WO 89/0099 1 PTU8/2 PCT/US88/02459 103 Corrpmgn Name Chemical Name pr ophan 1-methylethy. phenylcarbaiate prosulfalin prynachior guizalofop ethyl secbumeton sethoxydim (4-(dipropylamino)-3, phenyl Jsulfonyl]J-S, S-dime thylsuif iiirnine 2-chloro-N- 1-methyl-2-propynyl ace tanilido 5-amino-4,,chloro-2-phenyl-3 (2Hl) pyridazinone -chloro-'i-quinoxalinyl) oxylphenoxylpropaxioic acid, ethyl ester N-ethyl-6-methoxy-N' 1-methylpropyl)- 1, 3, 5-triazine-2,4-dianine thio)propyl 1-3-hydroxy-2-cyclohexen- 1-one N-(2-meithylcydlohexyl) -N I -phenylurea 2, 4-diamine 6-dime thyl -2 -pyritmid-inyl) amino) carbony) amino I sulfonyl 1benzoic acid, methyl ester txrichloroacet~ic acid N-(5-(1,1-dimelthylethy2)-1,3,4-thiadiazol-2-yl ]-NN -dimethylurea 5-chloro-3- (1 l-dilmethylethyl) -6inethyl-2, 4(LH,3fU-pyrimidinedione dimethyle thy! -6-rnethyjlpheny.I aceta'nide s iduron s imazine s('4 Iomettiron methyl

TCA

tebuthiuron terbacil terbuchlor r-- WO $9/00991 PC-Y/U588/02459 104 Commn N~tei terbuthylazine terbuto.

terbutryn thi ame t~xron methyl thiobencarb triallate Chem ig Name~ 2-CtUr.t-butyl amino) -4-chlor'3-6-(ethylamino) triazine b amate 1,1-dime thylethyl )N-ethyl-6- (rethylthio)-1,3, 2,4-dianiine- (4-methoxy-6-methyl-1,3, triazin-2 -yl) amino) carbonyl amino] sulf onyJ. I-Z-thiophenecarboxylic acid, methy! ester S-t4A-chJlorophenyl)methylj diethylcarbamo thto ate S-(2,3,3-trichloro-2-propeny1) bis(lmethylothyl.) carbamothioate 5, 6-tri chlor--2-py'ridinyl) oxy~acetic arid 2-(3,5.,dichlorophenyl)2-(2, 2,2trichioroethyl )oxirane fluoromethyl )benzenamine 1-(p-ch~orophenyl 3-trimethylpseudourea (2t 4-dichlorophenoxy) acetic sicitd 4 -(2,4-dichlorophenoxy)butanoic acid S-.propyl dip ropyl carbamothioate 2-chloro-N- 3-dimethyiphenyl (1-methylethyl)acetamide triclopyr tridiphano trimeturon 2, 4-DB ye rnol ate xylachlor The herbicidWal properties of the subject comnpounds were discovered in a number of greenhouse tests.

The test procedures and results follow.

WO 89/00991 PCT/US88/02459 105 COMPOUND TABLES

NOR

CMPD

2 3 4 5 6 7 8 9 10 12 12 13 14 15 16 17 18 19 20 21 22 23 24

E

CH

3

CH

3

CH

3

CH

3

CH

3

CHJ

CH

3

CH

2

CH

3 CH2CH3 CH2CH- CH2CH3 CH2CH3 CH(CH3)2 CH (CH3) 2 CH(CH3) 2 CH (CH3 CH(CH3)2 CH(CH3)2 CH3 CH3 CH3 CH3 CH3 ac,' 3

CR

3

CH

3 Cl

OCR

3

OCH

3 0C 2

R

5

OCH

3

CR

3

CH

3

CH

3 OCH3 OCH3 3

CH

3

CH

OCH3 OCH3

CR

3 OCH3 OCH3 OCH3 OCH3

CR

3 OCH3

CH

3

OCR

3 NHCH3 OCH3 OCH3

CH

3

OCR

3

C

3 OCH3 OCH3

OCR

3

CR

3 O'CH3

OCR

3 OCH3

OCH

3 OCH3

OCR

3 CH 3

OCH

3

QC

3 203 to 210 190 to 192 201 to 203 dec.

195 to 200 189 to 191 191 to 194 180 to 2186 203 to 207 182 to 186 191 to 196 165 to 170 188 to 192 1V8 to 182 .'90 to 193 490 to 192 1.72 to 176 155 to 160 176 to 180 178 to 183 197 to 200 153 to 160 175 to 183 182 to 184 dec.

183 to 187 WO 89/00991 WO 8900991PCTfUS88/02459 COMPOUND TABLE3 (continued)

NOR

to -Cl 0 SO 2

NCON,(

26 27 28 29 31 32 33 34 36

CH

3

CH

3

CH

3

CH

3

CH

3

CR

3

CH

2

CH

3

C

2 3

CH

2

CR

3

CR

2

CH

3

CH

2

CR

3 OCI4 3

CR

3

CR

3 Cl

CR

3

OCR

3

OCH

3

CR

3

CR

3 Cl

CH

3

OCH

3

OCH

3

C

3

CR

3

OCH

3

OCR

3

OCR

3 OCR4 3

C

3

CR

3

OCR

3 OCH 3 200 179 180 222 184 188 167 170 163 163 18Z 120 d~ec.

NOCH

,C

37 38 C cI-Ik 3 OCR1 3

CH

3 OCH 3 rnMp L 17 5 to 17 8 165 to 170

I

p- WO 89/00991 WO 8900991PCT/US88/02459 COMPOUND TABLES (continued) CMPD R 39 41 42 43 44 46 47 48 49 so 51 52 53 54 56 57 58 59 Cl Cl Cl

OCH

3

CN

UN

H

CH

3 Cl

CH

3 OCH 3 OCH 3

CM

3

CH

3 CH3

C

3

CH

3 CH 3 CH3

C

3

OCH

3 0CM 3

CH

3 Cl

CM

3 0CH 3

CM

3 0CH 3

OCH

3

CM

3

OCH

3

OCM."

0CM 3 0CM 3

OCH

3

C

3 0CH 3 0CM 3 0CM 3 OC3

C

3

GM

3 0CH 3 0C4 3 0CM 3 140 160 138 165 182 158 184 170 143 160 175 169 175 158 159 168 167 177 170 166 164 167 dec.

dec.

dec dec.

dec.

dec

A,

D-iDromo-b -me thyl-3 -me thylp ropyl)- 2,4(1X, 3H)pyrimidinedione WO 89/0099 1 PCT/US88/02459 COIMPOUND TABLES (continued)

NOCH

3 it CMPD R 0c 61 62 63 64 66 67 68 69 71 72 uCH 3

CH

3

CH

3 Cl

C.'

O3

OCH

3

CH

3

CH

3

CH

3

CH

3

OCH

3

OCH

3

CH

3

OCH

3

OCX

3

OCX

3

OCH

3

OCX

3

CE

3

OCH

3 OCH 3

OCX

3 184 196 187 175 166 180 169 202 180 180 168 192 200 190 179 170 185 175 204 184 193 172 186 73 74

OCH

3

CH

3

OCX

3

OCX

3 206 to 208 204 to 206 oxy) iminolpropyl].5-(2-(ethylthio)propyl]1- 3 -hydroxy-2-cyclohexen..1one WO 89/00991 PCT/LJS88/02459 109 COMPOUND TABLES (continued) -CMPD X 76 77 78

CM

3 Cl

CM

3 0CM 3

CH

3 0CM 3 0CH 3 0CH 3

NOCII

3 179 to 182 197 to 201 190 to 194 198 to 201 179 to 181 dec.

148 to 163 dec.

145 to 160 dec.

140 to 151 dec.

140 to 150 dec.

156 to 164 dec.

CM4D x 79 81 82 83 84 0CM 3

CH

3

CM

3 Cl

CM

3 0CM 3 0CM 3 0CM 3

CM

3 0CM 3 0CM 3 0CH 3 dichlobeni.

3,6-dichloro-2--methoxybenzoic acid 2, 6-dichJlorobenzonitrile WO 89/00991 PCT/US88/02459

NOCH

3 O 0 2

NHCONH-

CMPD X m P. (C)

OCH

3

CH

3

CH

3 Cl

CH

3

OCH

3

OCH

3

OCH

3

CH

3

OCH

3

OCH

3 oCH- 3 179 176 194 167 157 1.73 182 179 197 170 160 177 WO 89/00991 PCT/US88/02459 111 TestA Seeds of crabgrass (Digitaria spp.), barnyardgrass (Echinochloa crus-galli), giant foxtail (Setaria faberi), wild oats (Avena fatua), cheatgrass (Bromus secalinus) or downy brome (JBromus tectorum), velvetleaf (Abutilon theophrasti), morningglory (Ipomoea spp.), cocklebur (Xanthium pensylvanicum), sorghum, corn, soybean, sugarbeet, cotton, rice, heat, barley and purple nutsedge (Cyperus rotundus) tubers were planted and treated preemergence with the test chemicals dissolved in a non-phytotoxic solvent. At the same time, these crop and weed species were treated with a soil/foliage application. At the time of treatment, the plants ranged in height from 2 to 18 cm. Treated plants and controls were maintained in a greenhouse for sixteen days, after which all species were compared to controls and visually rated for response to treatment. The ratings, summarized in Table A, are based on a numerical scale extending from 0 no injury, to 10 complete kill. The accompanying descriptive symbols have-the following meanings: C chlorosis/necrosis B burn D defoliation E emergence inhibition SG growth ret-rdation H formative effect U unusual pigmentation X axillary stimulation S a albinism 6Y a abscised buds or flowers.

F'

WO 89/00991 PCT/US88/02459 TABLE A CMPD 1 CMPD 2

RATE=KG/HA

POSTEMERGENCE

COTTON

MORNINGGLORY

COCKLEBUR

NUT SEDGE CRAB GRAS S BARNYARDGRAS S WILD OATS

WHEAT

CORN

SOYBEANS

RICE

SORGHUM

CHEATGRASS

SUGARBEETS

VELVETLEAF

GIANT FOXTAIL

BARLEY

0.05 9C loc 9C 9C 0 6G 7G 9G 9C 9C 6G 9G 3.0C 2C, 7G 8G 0.01 0.05 9C loc 9C 9C 0 9C 2G 6G 2C, 9G 9C 5C, 9G 5G 7G 9C 9C 3G 6G 9c loG 9C 3G 5C, 9G 5C, 13G 5U, 9G 9C 5C, 9G 4C, 9G 4C, 9G loc loG 5C, 9G 4C, 913 0.01 5C, 9G boC boC 3C, 8G 0 3C, 9H 6G 7G 3C, 9G 9C 3C, 7G 4C, 9G 5C, 9G 9C 5C, 9G 7G 2C, 7G TABLE A CMPD I CMPD 2

RATE=KG/HA

PREEMERGENCE

COTTON

MORN ING GLORY

COCKLEBUR

NUT SEDGE

CRABGRASS

BARNYARDGRASS

WILD OATS

WHEAT

CORN

SOYBEANS

R ICE

SORGHUM

CHEATGRASS

SUGARBEETS

VELVETLEAF

GIANT FOXTAIL

BARLEY

0,*05 9G 913 2C, 7G 9G 2G 8H3 2C, 6G 80 2C, 9H3 3C, 913 90 3C, 8H.

3C, 80 90 90G 8G 0.01 2G 2C, 4G 2C, 7G 3G 0 6G 3G 5G 2C, 6G 413 6G 0 5G 9G 70 0 60 0.*05 0.01 3C, 8G 3C, 8G 3C, 413 9G 5G 9}i 3C, 5G 3C, 8G 3C, 813 3C 713 913 3C, 9H3

BG

3C, 9G 4c, 9G 9H 80 0 0 0 313 2C, 3G 3C, 6H3 3C, 6H3 713 313 3G 2C, karbutijlate 3-[[(dimethylamino)carbonylamino].

phenyl- 1-dimethylethyl) carbamnate W89091113 TBEA PCT/US88/02459 CMPD 3 CMPD 4 RATE.=KG/HA 0.05 0.01 0.05 0.01

POSTEMERGENCE

COTTON 9C 5C,9G 9C 4C,9H MORNINGGLORY 10C 2C,7G 10C boC COCKLEBUR loc boC loc loc NUTSEDGE 9C 9C 9C 5C,9G CRABGRASS 6G 5G 3G 0 BARNYARDGRASS 9C 5C,9H 3C,9H 6H WILD OATS 4C,9G 4C,9G 6G 0 WHEAT 5C,9G 9G 5G 0 CORN 8U,9C 4U,9G 8H 3H,4G SOYBEANS 9C 9C 5C,9G RICE 6C,9G 6C,9G 3C,8G SORGHUM 9C 6C,9G 8H 2C,8G CHEATGRASS 9C 5C,9G 9G SUGARBEETS 9C 5C,9G 10C 9C VELVETLEAF lOC loc 9G GIANT FOXTAIL 4C,9G 5G 5G 0 BARLEY 5C,9G 9G 6G 2G TABLE A CMPD 3 CMPD 4 RATE=KG/HA 0,05 0.05 0.01

PREEMERGENCE

COTTON 9G 5H1 3CVJG 7G MORNINGGLORY 9G 9G 9G 9G COCKLEBUR 9G 3C,5H 3Co611 3C,8G NUTSEDGE 10E 5G lot E CRABGRASS 5G-2G 0 BAflNYARDGRASS 9H1 2C 3C,7H- 0 WILD OATS 2Co8G 3C,7G 2C,3G 0 WHEAT 3C, 9H 2C,8G 2G 2G CORN 9G 4C,8G 3C,7H 2C,2G SOYBEANS 9H 3C,7H 3C 1 4G 0 RICE 10E 9 H 9G 7G SORGHUM 10E 9H1 3C,9G 2C,7G CHEATGRASS 91H 7G 7 G 0 SUGA!RBEETS 9G BG 3Co9G 3C,9G VELVETLEAF 9G 811 9G 8H1 GIANT FOXTAIL 9 H 3G 7 G 0 BARLEY 9G 9G 3Co7G 2G WO 89/00991 WO 8900991PCT/US88/02459 TABLE A CMPD 5

RATE=KG/HA

POSTEMERGENCE

COTTON

MORNINGGLORY

COCKLEBUR.

NUTSEDGE

CRABGRASS

BARNYARDGRASS

WILD OATS

WHEAT

CORN

SOYBEANS

RI CE

SORGHUM

CHEATGRASS

SUGARBEETS

VELVETLEAF

GIANT FOXTAIL 13ARLEY 0.05 9C loc 4C, 9G 0 0 0 0 3C, 9G SC, 9G 0 20 0 lOC 0 0.01 4C, 9G 5C, 9G lOC 8G 0 0 0 0 3H 5C, 9G 0 0 0 boC 5C, 9H4 0 0 CMFD 6 0.05 5C, 9G 5C, 9G 5C, 9G 2C, 2G 0 0 0 0 3C f 8H4 5C, 9G 0 2G 0 9C 0 2C, 5G 0.01 5C,9G 5C, 9G 3H, 6G 0 0 0 0 0 0 sc, 9G 0 0

Q

9C SC, 9H- 0 0 TABLE A CMPO 5 CMPD 6 RATE-4(G/HA

PREEMERGENCE

COTTON

MORNXINGGLORY

COCKLEBUR

NUTSEDGE

CRABGRASS

BARN'YARDG~RASS

WILD QATS

WHEAT

CORN

SOYBEANS

RICE

SORGHUM

CHZATGRASS

SUGARBEETS

VELVETLEAF

GIANT FOXTAIL

BARLEY

0.05 0101 Q 10$ 0.01 81-H 9Q 8 H 3 G 0 0 0 7 G 4C, 8H 3C, 5G 5C, 9G

BG

2G 4G 8G 0 0 0 0 0 2.0 3c, $G 0 0 0 6G 0 0 3C, 7G 9G 5G 0 0 0 0 0 3C, 6G 3C, 7H4 0 2G 0 5C, 9G 2C, SG 0 0 2G 3CO G 2G 0 0 0 0 0 2G 3C, 31 0 0 0 2G 0 0 oryzalin 4-(dipropylanino) benzenesulfonamide WO 89/00991 PCT/US88/02459 115 TABLE A CMPD 7 CMPD 8 RATE-KG/HA 0.05 0101 0.05 0101

POSTEMERGENCE

COTTON 4C,9G 4C,9G 5C,9G 9C MORNINGGLORY 9C 5C,9G 10C 2C,6G COCKLEBUR 5C,9G 111 loc lOC NUTSEDGE 3C,9G 3C,5G 5C,9G 4C,9G CRABGRASS 2G 0 0 0 BARNYARDGRASS 3Ce8H4 3G 9C 3C..91 WILD OATS 2G 0 4G 2G WHEAT 0 0 2G 0 CORN I4Cg.G 3C,8G 3C,6H 2C,4G SOYBEANS 3C,8G 4C,9G 9C 4C,9G RICE 3Ct7G 6G 4C,9G SORGHUM 70 2C,2G 4C,8H 3C,7G SUG0ARBEETS oc lOG lc 1c VELVETLEAF 5C,9G 4C,8H- 1c 9C GIANT FOXTAIL 3G 0 3C,7G BARLE~Y 2C,20 0 3C,6G 3G DOWNY DROME 0 0 3C,8G 2C,3G TABLE A CMPD 7CMPD 8 201 RATE PKG/HA 0. 0.01 0105 0.01

PREEMERGENCE

COTTON 50 3G 70 0 MOROINGGLORY 90 1C 2C,5H- 7G COCKLEBUR 3G 3C,8H- NUTSEDGE 0 00 IOE CRABGORASS 2C,4G 0 2C,3G 0 HARNYARDGRASS 3C,7G 0 3C 1 4G 0 WILD OATS 3G 20 2Co5G WHEAT 0 0 3G 0 CORN 9G 3CI60 3C,9H 2C,2G SOYBEANS 3CI9F1 7H 8 3C,7H- RICE 80 5G 8G ZC14G SORGHUM 3C,8H 30 8H1 2Co2G SUGARBEETS 5C,9G 90 VELVETLEAF 2Cj80 3H- 8H1 3C,5t1 GIANT FOXTAIL Q 0 MC40 0 BARLEY 2C, 23 IC: 0 0 DOWNY BROM-E 3G 2(1 9H1 propazine N- 4 -dichlo rophenyl. )propanamicle 6-chloro-N,N'-bis (I-me thylethyl) 11 3, 5-triazine-2 ,4-diamine I

I

S.-

WO 89/00991 PCT/US88/ 02459 TABLE A CMPD 9 CMPD RATE =KG/HA

POSTEMERGENCE

COTTON

MORNINGGLORY

COCKLEBUR

NUTSEDGE

CRABGRASS

BARNYARDGRASS

WILD OATS

WHEAT

CORN

SOYBEANS

RICE

SORGHUM

SUGARBEETS

VELVETLEtNF GIANT FOXTAIL

BARLEY

DOWNY I3ROME 0.05 5C, 9G loc loc 5C, 90 0 4C, 9H 2C, 30 2G 3C, 8H 10(2 3C2, 9G 3C2, 9G 9(2 9C 3C2, 7G 2Q, 5G 4C2, 8G 0.01 0.05 6G loc 9C 4C, 9G 0 3C, 7G 0 0 3C2, 6G 3(2, 8H 70 3C2, 8H 3(2, 7G 5C, 9G 0 2C, 203 3C2,40 4C, 9G 3C, 60 9C 4C, 90 3G 2C2,2G 3C, 5G 3(2, 5G 3C, 7G 4C2,9G 70 3C, 7G 4C, 9G 32, 7G 2G 3C, 5G 3C2, 7G .01 2G 1(2, 1H 4C, 9G 2(2, 0 0 0

Q

4 C, 9 2C, 4G 9C 3C, 7G 0 2C2,4G 2C2,4G TABLE A

RATE-KG/HA

PREEMERGENCE

COTTON

MORNINOLIORY

COCKLEBUR

NQTS EDGE

CRABGRASS

$ARNYARDORASS

WILD OATS W14EAT

CORN

SOYBEANS

RICE

$ORGHUM

SUGARBEETS

VELVETLEAF

GIANT FOXTAIL

BARLEY

DOWN~Y BROME CMPD 9 0.0$ 10E 3C2,3G 3C, 7H, 2C, 5G 4 G 3C, 9G 3(2, 814{

OH,

3(2, 9!j 80 8Hl 4G 3C, 7G 3C, 8G 010), 70 3C2,3H 3C,7H 0 0 2G 3 0 0 3C, $G 3 C 70 50r 3(2,5G 8 G 3C, 60 20G 30 $0 CMPD O0.05 0101 20 7G 811 3G 30 6G 40C 3Co 90 91-H 7 H 91H 90G 70G 20G 3c, 8(G 60 0 0 0 3G1 2C2, $0 WO 89j6'%ll 0 0, 'A WO 89~O99IPCT/US88/02459

RATE=KG/HA

POSTEMERGENCE

COTTON

MORNINGGLORY

COCKLEBUR

NUTSEDGE

CRABGRASS

BARNYARDGRAS S WILD OATS

WHEAT

CORN

iC SOYBEANS R ICE

SORGHUM

SUGARBEETS

VELVETLEAF

GIANT FOXTAIL

BARLEY

DOWNY BROME 117 CMPD 11 0.05 9 H oC 9 C 1c 3 G 2C,~ 5G 0 0 3C, 1G 4G 2C, 5G 3C, 7G 1c oc 2G 0 3C, 7G CMPD 12 TABLE A 0.01 3C, 8G 9C 9C SC, 9G 0 2H 0 0 2G3

IH

1C 2C, 4Q 3C, 8G 5C, 9 H 0

G

0 0.05 oC loG oc 3C, 7G 0 0 0 0 3C, 6G 9C 0 2G oC 9C 0 0 0.01 5C, 9G lC oC 4G

C

0 0 0

C

4C,. 9G 0 2G loC! 5C, 9G

C

0

C

TABLE A RATErnKG/HA

PREEMERCENCE

COTTON

MORN INGGLOP.Y

COCKLEBUR

NUTSEDGE

CRABGRASS

BARNYARDGRASS

WILD OATS

WHEAT

CORN

SOYBE? NS

RICE

SORGHUM

SUGARBEETS

VELVETSJEAF

GIANT FOXTAIL

BARLEY

DOWNY BROME CMPD 11 0.05 3G 5G 3C, 4H 10E 0

C

2G

C

2C, 5G

C

7G 7G 9G 5H 2G 0 30 CMPD 12 0.01 3GQ 4G 3C 5H

C

2C, 5G 0 0

C

0

C

4 G

C

8 G 3C, SH 2G 0 2G 0,05 0.01 4C, 9Q 9G 8H- 0

C

0 0 3C, 7G 9H 0 7G 5(111 9G 7H

C

0 0 6G 3C, 0 iC 0 0 i:,3G 3C, 8G 5C, 3C,

IC

3 G.

WO 89/00991 PCT/US88/ 02459 118 TABLE A CMPD 13 CMPD 14 RATE=KIA 0.05 0.01 0.05 0.01

POSTEMERGENCE

COTTON 5C,9G 4C,9G 7G 7G MORNINGGLORY boc boC 3C,8G 5C,9G COCKLEBUR loc 5C,9G 4-,9G 4C,9H N'UTSEDGE 9C 0 3C,9G 4C,9G CRABGRASS 0 0 0 0 BARNYARDGRASS 0 0 3C,8H WILD OATS 0 0 4G 0 WHEAT 0 0 2G 0 CORN 2Cf3G 0 4G 3G SOYBEAN~S 5C,9G 4C,9G 3C,9-. qC,9G RICE iC 0 4G 2G SORGHUM 0 2G 30 0 CWHEATGRASS 8G 0 S'UGARBEETS loc 9C 3C,7H 4G V;SLVETLEAF 9C 3C,8G 4C,9G 2C,8G GIANT FOXTAIL 0 0 3C,7G 0 BARLEY 2G 0 3G 0 DOWNY BROME 0 0 TABLE A CMPD 13 CMED 14 RATE=KG/HA 0.05 0101 0.05 0.01

PREEMERGENCE

COTTON 7H- 2C,5G 0 0 MORNINGGLORY 90 2C,3G 0 0 COCKLEBUR 7H 3C,30 2H- 0 NUTSEDGE 7G 0 0 0 CRABGR~ASS 0 0 0 0 BARNYARDGRASS 0 0 0 0 WILD OATS 0 0 30 0 WHEAT 0 0 0 0 CORN 2C,4G 0 0 0 SOYBEANS 4C,8G 3C,8H 0 0 RICE Q 0 4G 0 SORGHUM 0 0 0 0 CHEATGRASS 0 0 SUGARBEETS 5C,9G 5C,9G 30 0 VELVtUTLiEAF 80 2C,3G 0 0 GIANT VOXTAIL 0 0 0 0 BARLEY 0 0 0 0 DOV'Y B ROME 0 0 24 CH3 4 C 3 cl OCH 3

OCH

3 N 183 to IU31 WO 89/00991 PCT/US88/02459 TABLE A CMPD 16 RATE=KG /HA

POSTEMERGENCE

COTTON

MORNINGGLORY

COCKLEBUR

NUTSEDGE

CRABGRASS

BARNYARDGRAS S WILD OATS

WHEAT

CORN

SOYBEANS

RICE

SORGHUM

(HEATGRASS

SUGAR BEETS

VELVETLEAF

GIANT FOXTAIL

BARLEY

CMPD 15 0.05 91H 10C 5C, 9G 8G 0 7G 6G 3G 3C, 7G 5C, 9G 5G 3C, 4G 5G 3C, 5G 4C, 9G 3G 5G CMPD 15 0.01 0.05 7G 5C, 9H 4C, 9H 3G 2G 3H 2G 0 2G 3C, 6H 4G 2G 5G 5G 2H 2G 0 7G 3C, 8H 3C, 9H 0 0 2C, 5G 7G 2G 3C, 3G 3C, 5G 3C, 5G 3G 0 2G 5 G 4 G 0.01 5 G 2C, 3C, 6H 0 0 0 0 0 iC 2 C, 3 li 0 0 0 0 0 0 TkABLE A CMPD 16 RATE=KG /HA PRY, EMERGENCE

COTTON

MORNTINGGLORY

COCKLEBUR

NUTSEDGE

CRABGRASY'

BARNYARDGRASS

WILD OATS

WHEAT

CORN

SOYBEANS

RICE

SORG HUMJ

CHEATGRASS

SUGARBEETS

VELVETLEAF

GIANT FOXTAIL

BARLEY

0.05 0 8H 7H 0 0 2G 5G 4G 3C, 7G 3C, 7H 6G 2C, 5G 7G 4H 0 2G 0.01 0 0 2C, 3H 8G 0 0 2G 2G 2C, 3G 2G 2G 2G 3G 4G 0 0 0 0.05 2G 1H 1H 0 0 0 6G 5G 3C, 7G 0 3G 0 5G 7G 0 0 0.01 0 0 0 0 0 0 0 0 0 0 0 0 0 2G 0 0 0 38 Cl CH 3 OCH 3 CH 165 to 170 WO 89/06991 PGT/US88/02459 120 TABLE A CI4PD 17 CMPD 18 RATE=KG/HA 0.05 0.01 0.05 0.01

POSTEMERCENCE

COTTON 6G 4G 4C,8G 3C,7H- MORNINGGLORY 3C,8H 2H 9C 3C,9H COCKLEBUR 4C,9H 3C,8H 9C 3C,9H NUTSEDGE 2G 0 0 0 CRABGRASS 0 0 0 0 BARNYARDGRASS 4G 5G 0 0 WILD OATS 0 0 0 0 WHEAT 0 0 0 0 CORN 0 0 2H 0 SOYBEANS 2G 1H 3C,8H 3C,6H RICE 2C,3G 0 0 0 SORGHUM 0 0 0 0 CH-EATGRASS 0 0 0 0 SUGARBEETS 4G 0 5C,9G 4C,8G VELVETLEAF 7G 0 4C,9H 8G GIANT FOXTAIL 0 0 0 0 BARLEY 0 0 0 0 TABLE A CMPD 17 CMPD 18 RATE=KG/HA 0.05 0,05 0.01

PREEMERGXENCE

COTTON 2G 0 3G 0 MORNINGGLORY 0 0 7G 0 =(AJZLLEBUR 2G 0 8Ff 0 NUTSEDGE 0 0 0 0 CR~ABGRASS 0 0 0 0 BARNYARDGRASS 0 0 0 0 WILD OATS 0 0 0 0 WHEAT 0 0 0 0 CORN 2C,5G 0 0 SOYBEANS 0 0 3(,,7G 0 RICE 2G 0 0 0 SORG-tHM 0 0 0 0 CHEATGRASS 0 0 0 0 SUGARBEETS 5G 0 8G 0 VELVETLEAF 0 0 3G 0 GIANT FOXTAIL 0 0 0 0 BARLEY 0 ri0 0 WO 89/00991 PCT/US88/02459 121 TABLE A CMPD 19 CMPD RATE=KG/HA 0.05 0.01 0.05 0.01

POSTEMERGENCE

COTTON 3C,8G 3G 9C 5C,9G MORNINGGLORY 4C,9G 4CS,8H 10C loc COCKLEBUR 5C,9G 3C,9H 10C 9C NUTSEDGE 0 0 9C 0 CRABGRASS 0 0 5G 0 BARNYARDGRASS 0 0 9C 3C,9G WILD OATS 0 0 5G 0 WHEAT 0 0 8G 2G CORN 0 0 4U,9G 3C,8G SOYBEANS 3C,8G 3C,5H 9C 9C RICE 0 0 3C,8G SORGHUM 0 3G 9C 3C,9G CHEATGRASS 0 0 5C,9G 2C,7G SUGARBEETS 4C,9G 3C,8H 10C loc VELVETLEAF 3C,8H 3C,7H 10C 8G GIANT FOXTAIL 0 0 3C,6G 2G BARLEY 0 0 3CI.EG 3G TABLE A CMPD 19 CMPD RATE=KG/HA 0.05 0.01 0.05 0.01

PREEMERGENCE

COTTON 2G 0 3G 0 MORNINGGLORY 3C,4H 2G 9G 2G COCKLEBUR 2C,2H 0 3C,8H NUTSEDGE 0 0 9G 8G CRABGRASS 0 0 3G 0 BARNYARDGRASS 0 0 0 0 WILD OATS 0 0 3G 0 WHEAT 0 0 3C,5G 0 CORN 0 0 3C,9G SOYBEANS 3C,3H 2C,2H 3C.4H 0 RICE 0 0 3C,8G 0 SORGHUM 0 0 3C.9G, 2G CHEATGRASS 0 0 7G 0 SUGARBEETS 7G 5H 9G 7G VELVETLEAF 2C,2H 0 5C,9G 3H GIANT FOXTAIL 0 0 2G 0 BARLEY 0 0 3C,7G 2C 73 OCH3 OCH3 73 0H 3

CH

3 CH 206 to 208 74 CH 3 0GB 3 CH 204 to 206 WO 89/0099 1 PCT/LJSP,8/02459 122 TABLE A CMPD 21 CMPD 12 RATE=KG/HA 0.05 0.01 0.05 0.01

POSTEMERGENCE

COTTON 10C 3C,6G 9C

MORNINGGI

1 ORY 10C 3C,7H 10C 3C,8G COCK"FEBUR lbc>. 3C,8H 10C 2C,9G NUTSEDGE 5C,9G 9G 8G 0 CRABGRASS 4G 0 0 2G BARNYARDGRASS 5C,9G 2C,8H 1C,5H 2G WILD OATS 2C,7G 5G 3G 0 WHEAT 9G 3G 0 0 CORN 3C,9G 2C,7H 2C,7H 2G SOYBEANS 9C. 9c 6C,9G 2C,6G RICE 8G '5G2G 2G SORGHUM 5C,9G 9G 9G 2C,8H CHEATGRASS 4C,9G 9G 6G 6G SUGARBEETS 5C,9G 10C 9C 3C,7G VELVETLEAF 10C 9G 9C 2C,7G GIANT FOXTAIL 8G 4G 2G 0 BARLEY 9 C S 4G 0 TABLE A CMPD 21 CMPD 22 RATE=KG/HA 0.05 0.02. 0.05 0.01

PREEMERGENCE

COTTON iC 0 6G 0 MORNINGGLORY 5G 5G 9G 4G COCKLEBUR 3C,7H 3C,7H 8G 6G NUTSFDGE 10E 3G 10E 0 CRABGR~ASS 2G 0 0 BARNYARDGRASS 4G 0 0 0 WILD OATS 2C,5G 0 0 0 WHEAT 3C,9G 0 0 0 CORN 9G 2C,8G 2Q~ 0 SOYBEANS 9H 1C,4G 0 0 RICE 5C,8H 2G 3G 0 SORGHUM 9H 2C,7H 2C,8G 0 CHEATGRASS 9G 2G 6G Q SUGARBEETS 9G 9G 3Cf9G 0 VELVETLEAF 3G 0 8G 0 GIANT FOXTAIL 7G 6G 5G 4G BARLEY 9G 4G 1C,5G 0 WO 89/0099 1 PCT/US88/02459 123 TABLE A CMPD 23 CMPD 24 RATE=KG/HA 0.05 0.01 0.05 0.01 P0 STEMERG ENCE COTTON 4C,9G 4C,9G 5C,9G 0 MORNINGOLJORY 5C,59H 3C,7G 5C,9H 3C,4G COCKLEBUR 3C,9H 2C,4G 2C,7G 1C,3G NUTSEDGE 3G 3G 0 0 CRABGRASS 0 2G 0 0 BARNYARDGRASS 94C,8H- 3C,9H 3C,7H WILD OATS 8, 2C,3G 2C,6G 2G WHEAT 5G 3G 2G, 0 CORN 3C,8G 3C,7H 2C,8G 3C,4G SOYBEAN$ 6C,9G 4C,9G 4C,9G 3C,8G RICE 4G 2G 2G 0 SORGHUM 6C,9G 3C,8G 3C,9G 8G CH-EATGRASS 5C,9G BG 3C,9G BG SUGARBEETS 5C,9G 3C,6G 9C 5C,9G VELVETLEAF 3C,8G GIANT FOXTAIL 6G 3G 6G 0 BARLEY 0 0 2G 0 TABLE A CMPD 23 CMPD z4 20 RATE.=KG/HA 0.05 0.01 0.05 0.01

PREEMERGENCE

COTTON 8G 0 2G 0 MORNINGGLORY 9G 2C,6G 2C,4G COCKLEBUR 9Q G 2C,6G NUTSEDGE BG 0 5G 2G CRABGRASS 4G 2G 3G- BARNYARDORASS 4IG 0 0 0 WILD OATS 0 0 0 0 WHEAT I"G 0 0 0 CORN 4C,7H 0 iC 0 SOYBEANS 4C, 811 0 2C,2G 0 RICE 5C,88 0 2C,4G 0 SORGHUM 4C,8H 3C,.7H 4C,9G CHEATGRASS 4G 0 0 0 SUGARBEETS 5C,9G 3C,8G 4C,9G 4G VELVETLEAF 2C 1 .4G 0 2C,3C 2G GIANT FOXTAIL 3C,8H 2G 7G 3G BARLEY 2C,4G 2G 4G 0 WO 89/0099 1 PCT/US88/02459 124 TABLE A CMPD 25 CMPD 26 RATE=KG/HA 0.05 0.05 0.Oi

POSTEMERGENCE

COTTON loc 9C 3C,.7G MORNINGGLORY loG loc 4C,8G COCKLEBUR 9C OC5C,9G NUTSEDGE 9C 2C,9G CRABGRASS 2G 6G 2G BARNYARDGRASS 5C,9H 9C 4C,9H WILD OATS 9G 4C,9G 8G WHEAT 9G 4C,9G 9G CORN 9G 6U,9G 2C,8G SOYBEANS 9C 5C,9G 5C,9G RICE 9C 9C 3C,8G SORGHUM 2C,7H 4C,9G 2C,9G CHEATGRASS 6C,9G 9C 4C,9G SUGARBEETS loc loc 9C VELVETLEAF lOG loc 5C,9G GIANT FOXTAIL 4C,8G 5C,9G 3C,8G BAR~LEY 3G3 3C,9G 3C,9G TABLE A CMPD 25 CMPD 26 RATE=KG/HA 0.05 0.05 0.01 11PREEMERGENCE 20 COTTON 9G 9H 2C,7G MORNINGGLORY 9G 9H 8G COCKLEBUR 7G 9H 3C,7H NUTSEDGE 5G 9G CRABGRASS 5G 4G 0 BARNYARDGRAS3) 8H 9H 98 WILD OATS 3G 3C,8G 3C,8G WHEAT 6G 8G CORN 8H2C,9G 3C,7H SOYBEANS 91. 4C,8H- 3 C,414 RICE 3C, 9G SORGHUM 9G 2C, 9r. 3'C,9G CHEATGRASS 4 3C,9G 8G Sr.GARBEETS 8G 9G 9G VELVETLEAF 9G 9G 3C,818 GIANT FOXTAIL 8G 98 88 BARLEY 9G 8G ZC18G WO 89/00991 PCT/US88/0O.459 125 TABLE A CMPD 27 CMPD 28 RATE-KG/HA 0.05 0.01 0.05 0.01

POSTEMERGENCE

COTTON 4C,9G 6G 9C 2C,7G MORNINGGLORY 9C 3C,7G 10C 9C COCKLEBUR lOC 4C,9G 10C 9C NUTSEDGE 5C,9G 4C,9G 9C 9C CRABGRASS 7G 4G 2G 0 BARNYARDGRASS 9C 4C,9H 3C,8H WIL4D OATS 6C,9G 2C,9G 6G 0 WHEAT 5C,9G 3C,9G 5G 0 CORN 7U1,9C 3C,9G 3C,8H SOYBEANS 9c 9C 4C,8H 21H RICE 9C 5C,9G 3C,8G 2G SORGHUM 4C,9G 4C,9G 4Ct9G 3C,7G CHEATGRASS 9C 5C,9G 5C,9G 8G SUGARBEETS 9C 3,oc 9C loc VELVETLEAF 9C BG 9C 7G OIANT FOXTAIL 5C,9G 3Ce8G 4IG 0 BARLEY 5C,9G 2C,9G 3C,7G 2G TABLE A CMPD 27 CMPh) 28 20 RATE=KG/HA 0,05 0,01 0.03 0101

PREEMERGENCE

COTTON 9G 7G 5G 7G MORNINGGLORY 9G 5G 9i 8 G QQ)CKLJ1-UR 9 H 7 G 9 H 8H NUTSEDGE 109 9 G 9 G 4G CRABGRASS 5G 0 0 0 8ARNYARDGRASS 9 H 8H 7H- 0 WILD OATS 2C,8G 3C,5G 4G 0 WHEAT 3C,9H- 7G 5G 0 CORN 2C 1 9G 2C,9G 3C,7G 2G SOYBEANS 9 8H 0 0 RICE 9HA 9H 8H 3G SORGHUM 9H, 10H1 3C,8H 0 CH-EATGRASS 9H 8H1 7H 2G UGARbEETS 9G 7G 9C 7G VELVETlj:4AF 9 G 81-I 4C,9G 8G GIANT jVOXTAIL 9H1 3,(1 2G 0 BAR~LEY 9 G 8l 2C,6G 0 WO 89/00991 WO 8900991PCT/US88/02459

RATE=KG/HA

POSTEMERGENCE

COTTON

MORN INGGLORY

COCKLEBUR

NUTSEDGE

CRAB GRAS S BARNYARDGRAS S WILD OATS

WHEAT

CORN

SOYBEANS

RICE

SORGHUM

CHEATGRASS

SUGARBEETS

VELVETLEAF

GIANT FOXTAIL

BARLEY

126 CMPD 29 0.05 9C 5C, 9G loc 2C, 6G 6G 0 0 0 5U, 9H 5C, 9G 2C, 2G 4C, 9G 6G 9C 5G 0 TABLE A CMPD 0.01 5C, 9G 5C, 9G 9C 3G 0 0 0 0 6H 4C, 9G 0 4G 0 9C 0 0 0.05 9C 9C loc 9C 0 2H 0 0 3C, 8H 5C, 9G 0 2G 0 100 100 0 0 0.01 5C, 9G 9C 5C, 9G 4C, 7G 0 0 0 0 0 SC, 9G 0 0 0 9C 4C, 9G 0 0 TABLE A

RATE=KG/HA

PREEMERGENCE

COTTON

MORN INGGLORY

COCKLEBUR

NUTSEDJE

CRABGRASS

WILD OATS

WHEAT

CORN

SOYBEANS

RICE

SORGHUMJ~

CHEATGRASS

SUGARBEET$

VELVETLEAF

GIANT FOXTAIL

BARLEY

CMPD 29 0.05 9G 9 G 9H 10E 0 2G 0 0 8 G 91-H 20C, 8G 3G 4C, 90 sc, 9G 0 30 CMPD 0.01 0.05 5G 9G 7H- 0 0 0 0 0 0 0 7H- 0 0 3C, 8G 9G 3C, 7H- 0 0 0 0 0 30, SH 9H 0 2C 0.01 503 0 0 0 3C 0 37G 0 WO 89/00991 PCT/US88/02459 127 TABLE A CMPD 31 CMPD 32 RATE=KG/HA 0.05 0.01 0.05 0.01.

POSTEMERGENCE

COTTON 9C 9G 3C,9G 3C,9G MORNINGGLORY oc 3C,8G 10C loc COCKLEBUR loc 4C,9G 9C 4C,9G NUTSEDGE 9C 9C 9C CRABGRASS 5G 0 20 BARNYARDGRASS 4C,9H 3C,5G 4C,9H 8H WILD OATS 0 0 3C,7G 2C,3G WHEAT 2G 0 7G 3G CORN 3C,BG 3G 3C,9H 3C,8G SOYBEANS 4C,9G 3C,8G 3C,9G 3C,611 RICE 3C,9G 70 3C,9G 8G SORGHUM 3C,9G 3C,7G 9G 3C,90 CHEATGRASS 4C,9G 7G 3C,9G SUGARBEETS loc 2C,8G 9C 3C,8G VELVETLEAF loc 5C 1 9G 10C 5C,9G GIANT FOXTAIL 3C,6G 0 3C,7G 2G BARLEY 2Q,20 0 9G 7G TABLE A CMPD 31 CMPD 32 RATE=KG/I]A 0.05 0101 0.05 0.01 20 COTTON 20 iC 80 7G MORNINGGLORY 2C,311 0 8H1 3C,50 COCKLEBUR 8H 2C,3H 9H1 3C,711 NUTSEDGE 10E 0 iQE 0 CRABGRASS 0 0 2C,5G 0 BARNYARDORASS 3H1 0 9H1 WILD OATS 0 0 3C,BG 3G WHEAT 0 0 8H- 3G CORN 40 0 9H1 2Q SOYBEANS 3C,711 2Co3G 3C,7H 3C,GG3 RICE 3C, 8H- 6G 9118 SORGHUItM 9H. 2,50 3Qo90 3Ct90 CHEATGRASS 70, 3G 9H 7G SUGAR8EET8 311 8G 8G 3 VELjVETLEAF' 3G 0 711i 0 GIANT FOXTAIL 0 0 2C,4G 0 BAR~LEY 50 0 90 PCTfUS88/02459 WO 89/00991 RATE =KG /EA

POSTEMERGENCE

COTTON

MORN INGGLORY

COCKLEBUR

NUTSEDGE

CRABGRASS

BARNYARDGRASS

WILD OATS

WHEAT

CORN

SOYBEANS

RICE

SORGHUM

CHEATGRASS

SUGARBEETS

VELVETLEAF

GIANT FOXTAIL

BARLEY

128 CMPD 33 0.05 3C, 9G loc 9C 9C 3Ct 7G 9H 3C, 7G 9G 3C, 9Hi 3C, 9G 5Q, 903 2C, 9G 5C, 9G ioc 5Q, 9G 3C, 6-G 2C, 9G3 CMPJ 33 0.01 0.05 2C, 9G 4C, 9G 3C, 9H 9c 0 7H 2C 4G 3C, 7G 8H 8G 3C 1

SG

8(3 3C; 8G 8G 2G3 8G TABLE A CMPD 34 4C, 9G 9C loc 3C, 7G 3C, 8H- 0 2G 211 7G 2C, OG 3C, 190 9C 3Ct7G 0 0.01 2C, 9G 3C, 8G 4C, 9G 3C, 8(3 0 2C, 3G 0 0 0 0 2C, 4G 2 G 0 3C, 8G3 3C, 8G

'C

0 TABLjE A 20 RATE KG /HA

PREEMERGENCE

COTTON

MORN INGGLJORY

COCKLEBUR

NUTSEDGE

,CRABc3RASS WILD OATS WH4EAT

CORN

SOYDEANS

RICE

SORGHUM

CHEANTaRASS SU(ARB4ETS V4LVETLEAV GIANT VOXTAIL 8ARLEY 7G3 2C, 2Q 8G3 2C, 4G 7G 2C, 8H 9 H 91-H 3c, 9H- 0 4(G 9 G 0.01 0 4 G 3C, iC18 3C, 673 7(3 0 2(3

SG

CMPE) 34 00 8H- 2(3 0 3a 00 0 0 0 0 0 43H 1IH WO 89/0099 1 PCT/US88/02459 129 TABLE A CMPD 35 CMPD 36 RATE=KG/HA 0.05 0.01 0.05 0.01

POSTEMERGENCE

COTTON 5C,9G 4C,9G 5C,9G 4C,9G MORNIiNGGLORY 100 90 SC,9G 5C,9G COCKLEBUR 100 9C oC 9C NtJTSEDGE -0 0 CRABGRASS 0 0 0 0 BARNYAiRDGRASS 0 0 0 0 WILD OATS 0 0 0 0 WHEAT 0 0 0 0 CORN 4G 0 2G 0 SOYBEANS 4C,9G 5C,9G 5C,9G 4C,9G RICE 0 0 0 0 SORGHUM, 2G 0 2G 0 CHEATGRASS 0 0 0 0 SUGARBEETS 9C 4C, 9G loc VELVETLEAF 100 9C 9C GIANT FOXTAIIJ 2G 0 0 0 B3ARLEY 0 0 0 0 TABLE A CMPD 35 CMP) 36 20 RATE=YG/HA 0.05 0.01 0.05 0101 COTTON 2C,9G 3G 9G 3G MORNINGGLOP" 90 3H 9G 3G COCKLEBUR 9H 30 1 .5G 9H 3C,6H NUTS EDGE J.0E 0 40 0 CRABGRASS 0 0 2G 0 BARNYAROGRASS 0 0 2G 0 WILD OATS 0 0 0 0 WHEAT 0 0 0 0 CORN 2 C 5 3 3C,5G 20,3G 2C,2G SOYBEANS 8H 3050 3C, 8H 3C,7G RICE 0 a 20 0 SORGHUM 5G 4 G 20,20 2G CHEATGRASS 0 0 0 0 StGARBEETS 3C,90 4C,9G 5C,90 3C,BG VELVETLEAF s0,90 0 3C, 7H GIANT FOXTAIL 0 0 0 0 BARLEY 10 4G 0 0 PCT,'US88/ 02459 WO 89/00991 130 CMPD 37 XABLE A CMPD 38

RATE=KG/HA

POSTEMERGENCE

COTTON

MOININGGLORY

COCKLEBUR

NUTSEDGE

CRABGRASS

BARNYARDGRAS S WILD OATS

WHEAT

CORN

SOYBEANS

RICE

SORGHUM

CHEATGRASS

SUGARBEETS

VELV ETLEAF GIANT FOXTAIL

BARLEY

0.*05 5C, FiG lOC loc 2C, 9G 4G 9C 5C, 9G 6C, 9G 4U, 9G 9C 5C, 9 G 5C, 9G 6C, 9G 9C loc 9C 3C, 9G 0101 0.05 9C lee loc 4C, 9G 2G 5C, 9G 2C, 8G3 5 C,9 G 4iU, 9G 9C 9C 6C, 9G 3C, 9G 5 C ,9G 3.OC 4C, 9G 2C, 9G 9C 9C 9C 2C, 9G 3G 5C, 9G 3C, 7G Be 3C, 9H 5C, 9G 7G 4C, 8G 4C, 9G 5C, 9G oc 3C, 9G 2C, 5G 0.01 5C, 9G lee 3C, 8G 2C, 9G 0 4C, 8H' 3G 3C, 6H 4C, 9G 3C, 7G 3C, 9G 4C, 9H 9c 4C, 8G 3G TABLE A

RATE-KG/HA

COTTON

MORN INGGLORY

COCKLEBUR

NUTSEDG E

CRABGRASS

BARNYAP OGRAS S WILD OAT S

WHEAT

CORN

SOYBEANS

RICE

SORGHUM,

CHEATGRAS S

SUGARBEETS

VELVETLEAF

GIANT FOXTAIL

BARLEY

CMPD 37 1. 05 9G 9G 8H 10E 4G 9H 3C, 8G 4IC, 9H 9H- 3C, 7H 10H 4C, 9G 4IC, 9H 5C, 9G 5C, 9G 81-iH 9G 0.01 0105 8G 4G 10E 0 2G 3G 3C, 6G 6G 2C, 50 3C, 7G 9H 2C, BG 3G 4C, BG 4IC, 9G 3C, 7G 8G CMPD 38 4G 4G 20 3G 0 0 2G 2C, 2G 2G 3G 3G 7G 2H1 0 3G 0 Q 0 0 0 0 0 0

Q

0

Q

0 0 0 0 0 -q WO 89/00991 PTU8/25 PCT/US88/02459

RATE=KG/HA

POSTEMERGENCE

COTTON

MORNINGGLO<Y

COCKLEBUR

NUTSEDGE

CRABGRASS

BARNYARDGRASS

WILD OATS

WHEAT

CORN

SOYBEANS

RICE

SORGHUM

CHEATGRASS

SUGARBEETS

VELVETLEAF

GIANT FOXTAIL

BARLEY

131 CMPD 39 0.05 9C 1.0", 90 2C, 9G 3C, 7G 9C IC, 9G 50C, 9 G 30, 7G 5C., 9G 9C 5C, 9G 60, 9G 9C loc 9C 3C, 9G TAFLE A CMPD 0.01 0.05 5C, 4C, 9G 4C, 9G 9G 5G 5C, 9G 9G 8G 2G 5C, 9G 40, 9G 4C, 9G 9G 4C, 9H 90 4C, 9G 7G 9C loc 40, 9G 90 2C, 9G 9G 30, 8H 5C, 9G 50, 9G 5C, 9G 5C, 9G 90 100 40, 9G 30, 8G 0.01 50, 9G 9G 0 50, 9G 3C, 7G 8G 30, 7H 20, 7G 20, 7G 40C, 9 G' 30, PG 40, 8H 7G 4 C, TABLE A CMPD 39 CMPD 20 RATE =KG/HA

PREEMERGENCE

COTTON

MORN INGGLORY

COCKLEBURP

NUTS EDGE

CRABGRASS

B ARNYAROG RAS S WILD OATS

WHEAT

CORN

SOYBEANS

RI1CE

SORGHUM

CHEATGRASS

SUGARBEETS

VELVETLEAF

GIANT FOXTAIL

BARLEY

0.05 9 G 9 G 9 H 9 G 6 G 9 H 4C, 8H 30", 9 H 2C, 6G 9H 98 30, 9H 8H 40, 9G 40, 8H 30, 8H 9H 0.01 0.05 -7 G 8H 30, 5H 10E 2G 3C, 5G 30, 4G 7G 5G 98 108 40, 98 5G 7G 30, 7H 3C,7G 3C,811 40, 9G 9G 88 10E 6G 98 30, 6G 88 3C, 8G 88 9H 30, 9H 30, 8H 5C, 9G 40, 88 3C, 6G 8G 0.01 9G 30, 6P~ 9G 3G 3G 2C, 2G 8G 30, 7G 9H 30, 98 4G 3G 3G 30, 7G -4 WO 89/00991 PCT/US88/0245 9 1 32 TABLE A CMPD 41 CMPD 42 RATE-KG/HA 0.05 0.01 0.05 0.01

POSTEMERGENCE

COTTON 4C,9G 3C,5G 4C,9G 3C,8H MORNINGGLORY 5C,9G 3C, 9G 10C 4C,9G COCKLEBUR 4C,9G 2C,7G 4C,9G 3C,7G NUTSEDGE 5G 4G 3C,8G 0 CRABGRASS 4G 2G 3C,7G BARNYARDGRASS 5C,9G 5C,9G 4C,9G 4C,9G WILD OATS 4C,9G 2C,8G 4C,9G 3C,8G WHEAT 3C,7G 8G 5C,9G 5C,9G CORN 4C,9G 3C,9G 5C,9G 4C,9G SOYBEANS 5C,9G 3C,8H 9C 3C,8G RICE 5C,9G 4C 1 .9G 5C,9G 4C,9G SORGHUM 5C,9G 4C,8H 4C,9CG 4C,9G CHEATGRASS 5C,9G 3C,9G 4C,9G 3C,9G SUGARBEETS 9 C 3C,7G 9C 5C,9G VELVETLEAF 3C,7H 2G 4C,8H 4G GIANT FOXTAIL 5C,9G 4C,9G 9C 4C,9G BARLEY 8G 7G 4C,9G 8G TABLE A CMPD 41 CMPV 42 RATE-KG/HA 0.05 0.01 0.05 0.01

IEEMERGEN'CE

COTTON 6G 2G 3C,7G 2G MORNINGGLORY 9G 0 9G 2C COCKLEBUR 2%3 0 2C,7G 2G NUTSEDGE 0 0 5G 0 CRABGRASS 2G 0 5G 0 BARNYARDGRASS 2C,7G 0 4C,8H 4G WILD OATS 3C,7G 2C,2G 3C,7H 2C,2G WHEAT 2C,9G 6G 9H CORN 9G 3C,7C 9H 4C,6G SOYBEANS 9H 2C,2H 3C,7H 2C RICE 10E 6G 10H 9H SORGHUM 4C,9H 3C,8H 3C,9Fi 3C,3G CHEATGRASS 4G 0 3C,6G 6G SEJGARBEETS 7G 2H1 3C,9G 4G VELVETLEAF 2G 0 3G I H GIANT FOXTAIL 3C,7G 5G 4C,8H 3G BARLEY 9H 3C,BG 9H 2C,4G WO 89/00991 WO 8900991PCT/US88/02459 133 CI4PD 43 TABLE A CMPD 44 RATE=KG /HA

POSTEMERGENCE

COTTON

MORN INGGLORY

COCKLEBUR

NUTSEDGE

CRABGRASS

BARNYARDGRASS

WILD OATS

WHEAT

CORN

SOYBEANS

R ICE

SORGHUM

CHEATGRASS

SUGARBEETS

VELVETLEAF

GIANT FOXTAIL

BARLEY

0.05 5C, 9G 9C loc 9C 9C 4C, 9G 9C 9C 6C, 9G 6C, 9G 9C 6C, 9G 9C loc 9C 5C, 9G 0.01 5C, 9G loc 4C, 8H 4C, 9G 5G 9C 2C, 9G 9C 4C, 9G 6C, 9G 6C, 9G 4C, 9G 4C, 9G 9C 10C 5C, 9G 3C, 9G 0.05 4C, 9G loc loc 4C, 9G 2C, 6G 5C, 9G 3C, 9G 9G 4C, 9H 6C, 9G 9C 4C, 9G 5C, 9G 9C 10 C 9C 3C, 9G 0.01 4C, 9G 9C 4C, 9G 9G 2G 3C, 9G 3C, 7 G 3C, 61] 3C, 8G 9C 4C, 9H 4C, 8G 9C 5C, 91] 5C, 9G 3C, 7G TABLE A CMPD 43

RATE=KG/HA

PREEMERGENCE

COTTON

MORN INGGLORY

COCKLEBUR

NUTSEDGE

CRABGRASS

BARNYARDGRASS

WILD OATS

WHEAT

CORN

SOYBEANS

RICE

SORGHUM

CHEATGRASS

SUGARBEETS

VELVETLEAF

GIANT FOXTAIL

BARLEY

0 .0Q5 0.01 9G 9H 9H 10E 7G 9H] 4C, BG 9H] 1, H 9H 10 E 9H] 10E 9G 4C, 9G 3C, 8G 3C, 9G 9G 9H 8HF 10E 3G 9H] 3C17G 8H 9H 9H] 10H] 4C, 91] 9H 9G 4C, 9G 3C, 8G 9G CMPD 44 0.05 5G 9G 2C, 71] 10E 2G 4C, 7H- 3C, 6G 9H] 4C, 9G 9H 10H 5C, 9H 9H] 3C, 9G 4C, 81] 3C, 81] 9G 0.01 2G 3C, 6H] 0 0 4H 2C, 3G 7H] 3C, 7G 4C, 7H] 3C, 6H- 3C, 81] 8H 9G 3C, 61] 51] 81] WO 89/00991 PCr/UJS88/02459 134 TABLE A CMPD 45 CMPD 46 RATE-KG/HA 0.05 0.05 0.01

POSTEMERGENCE

COTTON 3C,9G 9G 9C 9G MORNINGGLORY 9C 5C,9G 6C,9G 5C,9G COCKLEBUR 9C 4C,9G 10C 3C,9G NUTSEDGE 9G 9G 9G 3C,9G CRABGRASS 3G 2G 4G 3G BARNYARDGRASS 4C,9G 4C,8H 9C 9H WILD OATS 3C,7G 7G 3C,9G 6G if WHEAT 9G 8G 9G 6G C]ORN 2G 0 2C,3G 0 SOYBEANS 2C,6G 2C,3H 2C,6G 4H RICE 9C 90 9C 4C,9G SORGHUM 4C,9G 4C,8H 4C,9G 3C,9G CHEATGRASS 5C,9G 3C,8G 5C,9G 3C,9G SUGARBEETS 90 4C,8H 6C,9G 9C VELVETLEAF 5C,9H 4C,BH 2C,7G 4C,8H GIANT FOXTAIL 9C 3C,7G, 5C,9G 3C,8G BARLEY 9G 3C,6G 9G 4G TABLE A CMPD 45 CMPD 46 RATE-KG/HA 0.05 0.01 0.05 0.01.

PREEMERGENCE

COTTON 2C 0 50 2G MORNINGGLORY 3C,8H 3G 9G 8H COCKLEBUR 8H 2C,2H 9H- 8H NUTSEDGE boE 9G 9G CRABGRASS 2G 0 0 0 BARNYARDGRASS 3Cj7H 2H- 4C,8H 2H- WILD OATS 2C,3G 0 2C,150 2G WHEAT 5G 0 8H 3G CORN 3C,7G 0 40C, G 4G SOYBEANS 2C,5G 0 4C,8H- RICE 4C,8H 0 91-1 9H SORGHUM 30,9H- 3Cj3G 50,9- 30,8- CHEATGRASS 8H 0 3C,6G 6G SUGARBEETS 9G 8G 9G 8G VELVETLEAF 4C,7H 20,4H 4C,7H GIANT FOXTAIL 5H 6H 7H 7H- BARLEY 3C,8H- 0 9G 8H- WO 89/00991 WOc-i s9009 PTUO s/ 07-4 =9 135 CMPC) 47 TABLE A CMPD 48

RATE=KG/HA

POSTEMERGENCE

COTTON

MORN INGGLORY

COCKLEBUR

NUTSEDGE

CRABGRASS

BARNYARDGRAS S WILD OATS

WHEAT

CORN

SOYBEANS

RICE

SORGHUM

CHEATGRASS

SUGARBEETS

VELVETLEAF

GIANT FOXTAIL

BARLEY

0.05 0.01 0.05 0.01 6G 4C, SH 3C, 5H 4G 2G 3C, 4H 2C, 6G 4C, 9G 3C, 9G 0 3C, 9G 3C, 7H 4C2, 9G 3(2, 6H 0 2C, 6G 9G 0 2C, 2G 0 0 0 0 3G 0 0 3C, 9G 0 6G 3H 0 2G 0 6G 4C, 8H 2C, 3H 2C, 4G 3C2, 6H 2C, 6G 9G 3C, 9G 1(2 4C2, 9G 3C,7G 9G 3C2, 6H 2(2 3C, 8G 9G 0 0 iC 0 2G 0 2G 8G 2C, 4G 0 3C, 9G 2G 7G 3H 0 0 0 TABLE A CMPD 47 CMPD 48

RATE=KG/HA

PREEMERGENCE

COTTON

MORNINGGLORY

COCKLEBUR~

NUTSEDGE

CRABGRASS

BARNYAROGRASS

WILD OATS

WHEAT

CORN

SOYBEANS

RICE

SORGHUM

CHEATGRASS

SUGARBEETS

VELVETLEAF

GIANT FOXTAIL

BARLEY

0.05 0 4G 2G 0 4G 0 0 0 3C, 6G 0 2C, 5G 2C, 3G 0 2G 5G 4G 0 0.01 0 0 0 0 0 0 0 0 0 0 0 0 0 2G 2H 0 0 0,05 0.01 0 4G 0 2G 0 0 0 2C, 6G 0 4G 0 0 0 2G 3C, 7H 0 0 0 0 0 0 0.

0 0 1(2,2G 0 2G 0 0 0 0 3G 0 6L WO 89/00991 PCTF/US88/02459 136 TABLE A CMPD 49 CMPD RATE=KG/HA 0.05 0.01 0.05 0.01

POSTEMERGENCE

COTTON 9C lbC loc 3C,9G3 MORNINGGLORY loc loc 9C 9C COCKLEBUR loc loG 3C,7H 2C,4H NUTSEDGE -4C,9G 7G CRABGRASS 5G -0 2G BARNYARDGRASS 9C 5C,9G 3C,7H WILD OATS 9G 5G 40 2G WHEAT 9G 5G 7G 7G CORN 5C,9G 4C,9G 4C,8H 11-,3G SOYBEANS 9C 9C 3C,8H RICE 5C,9G 5C.9G 3C,6G 2C,3G SORGHUM 4C,9G, 4C,9G 3C,7G 4G CHEATGRASS 9C 5C,9G 3C,7G SUGARBEETS 9C 9C 9C 3C,8H VELVETLEAF ).oc lOC 9C 3C,7G GIANT FOXTAIL 9C 4C,9G 3C,7G 2C,SG BARLEY 2C,7G 0 0 0 TABLE A CMPD 49 CMPD RATE=KG/HA 0.05 0.01 0105 0.01

PREEMERGENCE

COTTON 5C,9G 7G 0 0 MORNINGGLORY 9G 8G 4G 0 COCKLEBUR 91-H 1c,1H 0 0 NUTSEDGE 1OB 1OE 0 0 CRABGRASS 5G 0 0 0 RZ P NYARDGRkSS 9H 0 0 0 WILD OATS 3C,6G 2G 0 0 WH-EAT 7G 0 0 0 CORN 4C,9G 3C,7G 3G 0 SOYBEANS 9H 3C,7G 0 0 RICE 9H 6 G 2G 0 SORGHUM 3C,9G 2C,5G 3G 0 CHEATGRASS 4C,BG 0 0 0 SUGARBEETS 5C,9G 7G 3G 0 VELVETLEAF 4C,9G 211 iC 0 GIANT FOXTAIL 4C,9H 30 2G 0 BARLEY 2C,8G 3C,7G 0 0 WO 89/00991 PCT/US88/02459 137 TABLE A CMPD 5 1 CMPD 52 RATE=KG/HiA 0.05 0.01 Q0. 05 0.01

POSTEMEPASENCE

COTTON 5C,9G 3C ,9,G 4C,9G 4C,9G MORNINGGLORY 9C 4C,9G 10C 5C,9G COCKLEBUR 5C,9G 4C,9G 9C 4C,9G NUTSEDGE 9G 2C,9G 4C,9G CRABGRASS 2C,2G 0 2C,2G 0 BARNYARDGRASS 4C,9G 3C,8H 5C,9G 4C,9G WILD OATS 9G 8G 2C,7G 2G WHEAT 9G 2C,9G 8G 3G CORN 2C,9H 6 4C,9H 3C,8G SOYBEANS 5C,9G 4C,9G 5C,9G 3C,7H RICE 5C,9G 3C-,6G 5C,9G 2C,3G SORGHUM' 4C,9G 4 BG 5C,9G 4C,9G CHEATG1RASS 5C,9G 8G 5C,9G 7 G SUGARBEETS 9C 4C,9G 9C 9C VELVETLEAF 9C 3C,8H 10C 9C GIANT FOXTAIL 4C,9G 3C,,9G 3C,7G 6 G BARLEY 8 G 6G 6G 3 G TABLE A CMPD 51 CMPD 52 RATE=KG/HA 0.05 0.01 0.05 0.01

PREEMERGENCE

COTTON 9G 3C,5G 3C,7G 3C,4G MORNINGGLORY 9 G 2H 9C 3C,3G COCKLEBUR 7H 2C 9H 0 NUTSEDGE 10E 3C,5G 10E 3G CRABGRASS 2C 0 0 0 BARNYARDGRASS 3C,8G 0 3C,~8H 3G WILD OATS 3C,7G 3C,4G 2C,3G 0 WHEAT 3C,8H 7G 5 G 0 CORN 3C,9H 3C,8G 4C,9H 2G SOYBEANS 9H 4C,8G 4C,8H 3C,6G RICE 9 H 3C,4G 4C,9G 2C,7G SORGHUM 3C,9H 3C,7G 5C,9G 4C,8G CHEATGRASS 9G 8G 3C,8H 6G SUGARBEETS 3C,9G 3C,6H 4C,9G 3C,7G VELVETLEAF 3C,5H. 2C,3G 2C,2H GIANT FOXTAIL 3Co7G 2C,SG 3C,BH 2G BARLEY 9G 2G 4C,8G 2C,3G WO 89/00991 PCT/US88/02459 138 TABLE A CMPD 53 CMPD 54 RATE=KG/HA 0.05 0.01 0.05 0.01.

POSTEMERGENCE

COTTON 3C,4G 2C,3G 3C, 71j 3C MORNINGGLORY 4C,9G 1C,,2G 2C,2H 1C,1.H COCKLEBUR 2C,3G 1H 2C,3G 0 NUTSEDGE 5G 0 4G 0 CRABGRASS 2G 0 3G 0 BARNYARDGRASS 3C,6H 2C,3H 3C,7H 0 WILD OATS 3Q 0 3G 0 lo WHEAT 9C6G 9C 6G CORN 3C,7G 20 3C,7H SOYBEANS 2C,4G 0 3C,5H 2H RICE 5G 0 2C,5G 0 SORGHUM 3C,5G 0 3C,7G 2G CHEATGRASS 9G 5G 4C,9G 3G SUGARBEETS 4C,9G iC 3C,7H 1Hl VELVETLEAF 0 10 0 GIANT FOXTAIL 2C,6G 0 3C,7G 2G PAr-,RLEY 6G 30 3C,8G TABLE A CMPD 53 CMP'D 54 RATE=KG/HA 0.05 0.01 0,05 0101

PREEMERGENCE

COTTON 2C,2H 0 0 0 MORNINGGLORY 2C,2H 0 0 0 COCKLEBUR 1Hl 0 0 0 NUTSEDGE 0 0 0 0 CRABGRASS 0 0 0 0 BARNYARDGRASS 0 0 0 0 WILD OATS 0 0 0 0 WHEAT 0 0 0 0 CORN 30 0 2G 0 SOYBEANS 0 0 0 0 RICE 30 0 0 0 SORGHUM 2C,2G 0 2G 0 CHEATGRASS 0 0 0 0 SUGARBEETS 3H 2G ZG 0 VELVETLEAF 0 0 0 0 GIANT FOXTAIL 0 0 0 0 BARLEY 0 0 0 0 WO 89/00991 WO 8900991PCT/1iS88/02459 TABLE A CMPD 55 CMPD 56 0.02. 0.05 0.01 RATE=KG/HA P0 STFMERGENCE

COTTON

MQRN INGGLORY

COCKLEBUR

N UT SED GE

CRABGRASS

BARNYARDGRASS

WILD OATS

WHEAT

CORN

SOYBEANS

RI~CE

SORGHUM

CHEATGRASS

SUGARBEETS

VELVETLEAF

GIANT FOXTAIL

BARLEY

0.05 5C, 9G loc loc ).oc 4C, 9G 9C 3C, 8G 8G 5C, 9G 9C 9C 90 9C loc loc 4C, 9G 5G 5C, 9G 2C, 7G 9t 9C 3G 9C 3G 0 3C, 9H SC, 9G 3C, 8G 3C, 80 2C, 8G lOC 9C 3C, 70 0 100o 9 C 100 6C, 9G 4G 9H 9G 8G SC, 9G 9C 9C 3C, 8H SC, 9G 9C 9C 3C, 8G 5G 9C 2C, 4G 5C, 9G 3C, 8G 2G 3C, 9H 3C, 6G 3G 3C, 91-4 SC, 9G 2C, 3C, 7G 7G 9C 3C, 7G 0 TABLE A

RATE-KG/HA

PREEMERGENCE

COTTON

MORNINGGLORY

COCKLEBUR

NUTSEDGE

CRABGRASS

BARNYA1RDGRAS S WILD OATS

WHEAT

CORN

SOY88ANS P ICE

SORGHUM

CHEATGRASS

SUGARBEETS

VELVETLEAF

GIANT FOXTAIL

BARLEY

CMPD 55 0.05 80 9G 30, 7H 10E

SG

2C, 8H.

3C, 60 5G SCo 90 3C, 8H 9H 90 80 9G 4C, 9G 9H 6G CMPD 56 0101 30 0 0 0 a 4G 20 0 3C, 70 2C, 3H 8H 60 30 5H 30 0 0.05 2G 10, IH 2C 9G 3G 30, 6H 3C,S5G 60 40, 9H 2C, 4H 9 H, 2C, 70 70 4C, 9G 3C, 5H1 70G ZO,1 60 0. 01 0 0 0 9G 0 2G 1C 0 iC 1C 2G 0 B3G 0 0 WO 89/00991 C140 CPD5 PCT/US88/02459 TABLE A RATE=KG/HA 0.05 0.01 0.05 0.01

POSTEMERGENCS

COTTON 3C,9H 3C,7H 4C,8G 6G MORNINGGLORY 2C,2G 0 ocC 3C,7H COCKLEBUR 9C 1C,3H 7'-,7H 4H NUTSEDGE 4C,9G 3G 5C,9G 3C,7G CRABGR~ASS 3G 3G 2G 0 BARNYARDGRASS 3C,7H 3C,4H 3C,8H 2H WILD OATS 9G 5G 0 0 WHEAT 8G 4G 0 0 CORN 3C,8H 3G 3C,7H SOYBEANS 5C,9G 4C,9G 3C,7H 4H RICE 9C 3C,8G 2C,7G 2G SORGHUM 4C,9G 3C,9H 4C,9G 3C,8H CHEATGRASS 6C,9G 4C,9G 4G 0 SUGARBEETS 9C 5C,9G 9C 5C,9G VELVETLEAF 9C 3C,8H 3C,9G 'LC,2H GIANT FOXTAIL 2C,3G 2G 2C,6G 0 BARLEY 0 0 0 0 TABLE A CMPD 57 CMPD 58 RATE-KG/HA 0,05 0.01 0,05 0.01 PfEEMERGENCE COTTON 5G 2G 8G 3G MORNINGGLORY 0 3G 2C,6G 0 COCKLEBUR iC 0 0 0 NUTSEDGE 9G B G 0 CRABGRASS 0 0 0 0 IARNYARDORASS 3G 0 7G 0 WILD OATS 2C,7G 0 0 0 WHEAT 5G 0 0 0 CORN 3G 0 2C,3G 0 SOYBEANS 0 0 XC 0 RICE 6G 0 5G Q SORGHUM 4G 0 3C,7G 0 CHEATORASS 2C,6G c 0 0 SUGARBEETS 9G 2G 9G 7G VELVETLrLAF 3C,5H 0 2C,3G 0 GIANT FOXTAIL 3G 0 2G 0 BARLEY 2G 0 2G 0 :4- WO 89/00991 PCT/US88/02459 141 TABLEA CMPD 59 CMPL) RATE=KG/HA 0.05 0.01 iOQ 0.01

POSTEMERGENCE

COTTON 2C,3G 0 5G 0 MORNINGGLORY 3C,8G 1H 3C,8H 1C,lH COCKLEBUR 3C,8H 2G 3C,8H 2H NUTSEDt3E 0 0 3G 4 G CRABGRASS 0 0 2G 0 BARNYARDGRASS 3C,8H 2H 4C,8H 2C,4H WILD OATS 9G 5G BG 0 WHEAT 4G 0 5G 0 CORN 3C,9H 3C,6H 5C,9G 4G SOYBEANS 4C,9H 4H 3C,8G 4H RICE 9C 5C,9G 5C,9G 5C,9G SORGHUM 4C,9H 3C,6G 3C,9G 3C,7H CHEATGRASS 2C,7G 6G 4G 4G SUGARBEETS 9C 3C,5G 5C,9H 2C,6G VELVETLEAF 2C,5G 0 2C,7G 2G GIANT FOvTAIL 0 .0 3G 0 5 B,?RLEY 0 0 0 0 TABLrE A CMPD 59 CMPD RATE=.KG/HA 0.05 0.01 0.05 0.01

PREEMERGENCB

COTTON 0 0 0 0 MORNINGGLORY 0 0 0 0 COCKLEBUR 0 0 0 0 NUTSEDGE 10E 0 0 0 CRABGRASS 0 0 0 0 $ARNYARDGRASS 0 0 0 WILD OATS 0 0 0 0 WHIEAT 0 0 0 0 CORN iC 0 2C,2G 0 SOYBEANS 0 0 1C 0 RICE 3C,6G 0 5G 0 SORGHUM 3 G 0 2C,5G; 0 CHEATGRASS 0 0 0 0 SUGARBEETS 7 G 2 G 2H 0 VELVETLEAF 0 0 0 0 GIANT FOXTAIL 0 0 0 0 BARLEY 0 0 0 0 WO 89/00991 PCT/US88/02459 1 42 TABLE A llvpx) 61 CMPD 62 RATE=KG/HA 0.01 0.05 0.01

POSTEMERGENCE

COTTON 1C 1C oC 9C MORNINGGLORY 9C 1C iC 1C COCKLEBUR oC 1c 1C 1c NUTSEDGE oC oC oC CRABGRASS 4C,8G 2C,,rG 5C,9G 3G BARNYARDGRASS 9H 4C,6,4 9C 5C,9H WILD OATS 0 0 6G 2G WHEAT 0 0 6G 2G CORN 3C,6G 3G 5C,9G 3C,9H SOYBEANS 4C,9G 5C,9G 9C 5C,9G RICE 3C,7G 3G 4C,9G 3C,7G SORGHUM 3C,8G 6G 4C,,9G 4C,9G CHEATGRASS 3C,7G 5G 9C 8G SUGARBEETS 1c loc oC oC VE1LNETLEAF loc oC lC oC GIANT FOXTAIL 3Cf 6G 2G 5c,9G BARLEY 2C,4G 0 8G 7G TABLE A CMPD 61 CI4PQ 6 2 RATE=KG/HA 0.05 0,01 0105 Co1

PREEMERGENCE

COTTON 9G 6G 9G BG MORNINGGLORY 9G5G 9G 6G COCKLEBUR 7H- 2C,2G 9H 3C,6H- NUTSEDGE 1CE 8G 10E 3G CRABGRASS 3C,7G 0 3C,8G 3C,6G BAPNYARDGRASS 8314 1C 7H17H WILD OATS 2G C 3C,7G 2C,3G WHEAT 2G 0 8, SG CORNI 6G 0 3lk 1 3C,7G SOYBEANS 4C,9H 5G C9v 3C,8H RICE 8H C 8cG IC, 7G SORGHUM 8G 0 3C 1 9H 3CIS(.

CHEATGRASS 4C,9G 2r, 5C,8G aG SUGARBEETS 90 8G 5C,9G 4C,9G VELVJ1iTL.EAF 4C,8G' 3G 4C~~9G 7G GIAN'P FOXTAIL 3G 0 3C,80 6G BARLEY 3C,7G C 3C,9G 3C, 7G, WO 89/00991 PTU8/25 PC-T/US88/02459 TABLE A CMPD 63 CMPD 64

RATE=KG/HA

P0 STEME.x0ENCE

COTTON

MORN INGGLORY

COCKLEBUR

NUTSEDGE

CRABGRASS

BARNYARDGRASS

WILD OATS

WHEAT

CORN

SOYBEAN S RI CE SORG HUM

CHEATGRASS

SUGARBEETS

VELVETLEAF

GIANlT FOXTAIL B APLt Y 0.05 oC oC

)AJC

9 C 4C, 8G 9C 3C, 80 8G oC 9C 5C, 90 9C 9C oC 1C 5C, 90 9G 0.01 oC 9C oC 9C 5C, 90 9C 5G 5G 9G 5C, 9G 4C, 90 9C 5C, 90 lOC oc 4C, 80 8G 0.05 oc 1C oC 1C 2G 3C, 8G 0 0 0 4C, 90 30 3C, 7G 5G 9C 9C 5G 2G 0.01 5C, 9G

]IC

oC oC 0 4G 0 0 0 2C, 0 0 oC 3C, 0 0 TABLE A CMPD 63 CMPD 64 20 RATE=

KG/HA

PREEMERGENCE

COTTON

MO~N I NGGLORY

COCKLEBUR

NUT$ EDGE

CRABGRASS

BARNYARDORASS

WILD OATS

WHEAT

CORN

SOYBEANS

RICE

SORGHUM

CHEATGRASS

S!IARBEETS

VELVETLEAF

GIANT FOXTAIL

BARLEY

0.05 0.01 0.05 9G 9G 9 H 10E 803 9 H 3C, 7G 8H 90 91I 80 10R 9H- 90 9G 5G 9G 90 9G 9CE 310E 91H 3 G 3C, 9G 3C, 8H 2C, 6G 3C79H 90G 9 1"? 90 3C, 8C; 9G 90 3C, 5H- 10E 2C, 5G 2C, 5G 0 0 3C, 7G 3C, 5G 2C, 50 3C, 70 0 5C, 90 80 0 60 0.01, 9G 0 2G

C

0 0

Q

0 9G 0

Q

I

WO 89/00991 PCT/US88/02459 TABLE A CMPD 65 CMPD 66

RATE=KG/HA

POSTEMERGENCE

COTTON

MORN INGGLORY

COCKLEBUR

NUTSFDGE

CRABGRASS

BARNYARDGRAS S WILD OATS

WHEAT

CORN

SOYBEANS

RICE

SORGHUM

CHEATGRASS

SUGAR BEETS

VELVETLEAF

GIANT FOXTAIL

BARLEY

0.05 loc lOC loc 5C, 9G 4C, 8G 3C, 6G 0 2G 3C, 7H 9C 0 4C, 9G 0 loc lOC 3G 5G 0.01 0.05 5C, 9G 9C 9C 0 0 0 0 0 3G 5C, 9G 0 2G 0 loc 9C 0 0 lOC 9C 100 5C, 8G 0 5C, 9G 3G 0 2C, 7G 9C 0 0 Jl0C 9C 0 2G 0.01 5C, 9G 1 OC loc 3(3 '0 3C, 0 0 TABLE A 20 RATE=KG/HA

PREEMERGENCE

COTTON

MORN.INGGLORY

COCKLEBUR

NUTSEDGE

CRABGRASS

BARNYARDGRAS S WILD OAT$

WHEAT

CORN

SOYBEANS

RICE

SORGHUM

CHIEATGRAS S SUGAR

BEETS

VELVETLEAF

GIANT FOXTAIL

BARLEY

CMPD 65 0.05 9G 9G 9H 10E 3C, 8G

SG

0 0 3C, 7G 9G 0

BG

0 90 SC, 90 3C, SG 2G CMPD 66 0.01 9G 9G 81H 30 3G 0 0 0 3C, 6G 4IC, 80 0 S63 0 SC, 90 5G 0 0 0.05 9G 9G 9H 3G 2G 5G 0 0 3C, 7G 9H 0

SG

0 SC, 9G 4C, 8G 3G 0. Ul 8G 9G 7H 0 0 0 0 0 3C,7G 3C, 7H 0 3C, 4G 0 SC, 9G 0 0 WO 89/00991 PCT/US88/02459 145 TABLE A CMPD 67 CMPD 68 RATE=KG/H'A 0.05 0.01 0.05 0.01

POSTEMERGENCE

COTTON 5C,9G 2C,8G 5C,9G 3C,80 MORNINGGLORY 5C,9H 3G 3C-,7G 3C,3H COCKLEBUR 10Q 9C bC 5C,9G NUTSEDGE 6C,9G 9C 9C 9C CRABGRASS 0 0 0 0 BARN ';ARDGRASS 3H 2G 0 0 WILD )A-TS 0 0 0 0 WHEAT 0 0 0 0 0 CN 0 0 4G 3G SOYBEANS 5C,96 5C,9G 4C,9G 3C,8G RICE 0 0 0 0 SORGHUM 0 0 3C,6G 2G CHEATGRASS 3G 0 0 0 SUGARBEETS 9C loc 9C 3C,7G VELVETLEAF 5C, 9G 3C,7G 9C 3C,8G IS GIANT FOXTAIL 0 0 3G 0 BARLEY 2G 0 3G 0 TABLE A CMPD 67 CMPD 68 RATE=KG/1iA 0,05 0,01 0.05

PREEMERGENCE

COTTON 2G 0 2G MORNINGGLORY 0 0 2G COCKLEBUR 3C,5H 2C 3C,$H NUTSEDGE 10E 0 0 CRABGRASS 0 0 BARNYARDGRASS 0 0 30 0 WILD OATS 0 0 0 0 WHEAT 0 0 0 0 CORN 0 0 3C,6G 0 SOYBEANS 3C,5H 2C 1 2H 3C,3H 1H RICE 0 0 5G 0 SORGHUM 0 0 3C,66 0 CHEATGRASS 0 0 3G 0 SUGARBEETS 8G 5G 5G 4G VELVETLEAF 4H 0 4H 0 GIANT FOXTAIL 0 0 0 0 BARLEY 0 0 2G 0 m 1 PCT/US88/02459 WO 89/00991 TABLE A

RATE-KG/HA

POSTEMERGENCE

COTTON

MORN INGGLORY

COCKLEBUR

NUTSEDGE

CR.ABGRHAS S

BARNYARDGRASS

WILD OATS

WHEAT

CORN

SOYBEANS

RICE

SORGHUM

CHEATGRASS

SUGARBEETS

VELVETLEAF

GIANT FOXTAIL

BARLEY

CMPD 69 0.05 5C, 9G iC boC 3C, 8G 4G 0 0 0 3G 4C, 9G 2G 461 0 4C, 9G 3C, 9G 0 0 CMPD 0.01 3C, 8G 0 5C, 9G 5C, 9G 0 0 0 0 0 2C, BG 2G 2G 0 3C, 6G 2C, 50 0 0 0.05 0.01 7G boc 9C 5C, 9G 0 0 0 0 0 2C, 3H 0 0 0 3C, 8G 4C, 8G 0 0 3C, 7G 3C, 7G 4C, 8G 0 0 0 0 0 0 0 0 0 7G 0 0 TABLE A CMPD 6R~ CMPD 110 RATEmKCYHA

PREEMERGENCE

COTTON

MORNINGGLCRY

COCKLEBUR

NUTSEDGE

CRABGRASS

BARNYARDGRAS S WILD OATS

WHEAT

CORN

SOYBEANS

RICE

SORGHUM

CHEATGRASS

SUGARBEETS

VELVETLEAF

GIANT FOXTAIL

BARLEY

0.05 3G 0 3C, 5G 0 0 0 0 0 2G 3C, 4H 4G 7G 0 3H 0 0 2G 0.01 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0,05 0.01 WO 89/00991 RATE =KG/HA

POSTEMERGENCE

COTTON

MORN INGGLORY

COCKLEBUR

NUTSEDGE

CRABGRASS

BARNYARDGRASS

WILD OATS

WHEAT

CORN

SOYBEAN S

RICE

SORGHUM

CHEATGRASS

SUGARBEETS

VELVETLEAF

GIANT FOXTAIL

BARLEY

PCT/US88/02459 TABLE A CMPD 71 0.05 4C, 9G 5C, 9G loc 4C, 8G 0 0 0 0 2G 4C, 9G 0 0 0 5C, 9G 5C, 9G 0 0 CMPD 72 0.01 6G 3C, 7G 9C 0 0 0 0 0 0 4C, 9G 0 0 0 5C, 9G 3C, 5G 0 0 0.05 4C, 9G 4C, 9G 9C 9C 0 0 0 0 0 5C, 9G 0 0 0 9C 3C, 8G 0 0 0.01 4C, BG 2C, 6G 0 0 0 0 0 0 9G 0 0 0 4C, 8G 7G 0 0 TABLE A CMPD 71 CMPD 72 20 RATE=KG/HA

COTTON

MORN INGGLORY

COCKLEBUR

NUTSEDGE

CRABGRASS

BARNYARDGRASS

WILD OATS

WHEAT

CORN

SOYBEANS

RI CE

SORGHUM

CHEATGRASS

SUGARBEETS

VELVETLEAF

GIANT FOXTAIL

BARLEY

0.05 6G 3G 3C, 5G 0 0 2G 0 0 2G 0 0 0.01 0 .0 5 0 0 3H 0 0 0 0 0 0 3C, 3H 0 0 0 4C, 9G 0 0 0 0 6G 2C 0 0 0 0 0 0 3C, 7H 0 0 0 3C, 8G 0 0 0 0.01 0 2G 0 0 0 0 0 0 0 3C,3H 0 0 0 3C, 0 0 0 WO 8'fIO991 PCT/US88/02459 148 TABLE A CMPD 73 CMPD 74 RATE=KG/HA 0.05 0.01 0.05 0.01

POSTEMERGENCE

COTTON 9C 3C,7H 3C,7G MORNINGGLORY 5C,9G 7G 4C,9H 2C,3H COCKLEBUR 9C 2loc bC 3C,9G NUTSEDGE 4C,9G 3C,8G 3C,6G 0 CRABGRASS 3G 0 0 0 BARNYARDGRASS 3H 0 0 0 WILD OATS 0 0 0 0 WHEAT 0 0 2G 0 CORN 4C,9G 7H 3C,8H 3G SOYBEANS 4C,9G 3C,8H- 4C,9H RICE 4G 0 0 0 SORGHUM 4G 0 3C,3G 0 CHEATGRASS 3C,6G 3Q,60 3C,6G 0 SUGARBEETS loc 3C,7H 3C,90 3C,7G VELVETLEAF 9C 3C,7G 3C,7G 0 GIANT FOXTAIL 2C,4G 0 0 0 BARLEY 0 0 0 0 4 WO 89/00991 PCT/US38/02459 TABLE A CMPD 73 CMPD 74

RATE=KG/HA

PREEMERGENCE

COTTON

MORN INGGLORY

COCKLEBUR

NUTSEDGE

CRABGRASS

BARNYARDGRASS.

WILD OATS

WHEAT

CORN

SOYBEANS

RICE

SORGHUM

CHEATGRAS

S

SUGARBEETS

VELVETLEAF

GIANT FOXTAIL

BARLEY

0.05 0 3H 5H 5G 0 2H 2G 2G 2C, 7G 3C, 6H 6G 3G 7G 9G 7H 0 2G 0.01 0 0 0 0 -0 0 0 0 0 0 0 0 0 3H 0 0

Q

0.05 0.01 0 0 1H 0~ 0 0 0 0 0

'C

0 2C 0 7G 1H 0 0 1 I I WO 89/00991 PCT/US88/ 02459 150 TABLE A CMPD 77 CMPD 78 RATE=KG/HA 0.05 0.01 0.05 0.01

POSTEMERGENCE

COTTON 2G 0 7G 0 MORNINGGLORY 3H 0 2C,3H 0 COCKLEBUR 3C,8H 0 4C,8H 0 NUTSEDGE 0 '0 0 0 CRABGRASS 0 0 0 0 BARNYARDGRASS 0 0 0 0 WILDCOATS 0 0 0 0 WHEAT 0 0 0 0 CORN 0 0 0 0 SOYBEANS 1H 0 3H 0 RICE 3G 0 4G 0 SORGHUM 0 0 2C 0 CHEATGRASS 0 0 0 0 SUGARBEETS 5H 0 3C,7H 2G VELVETLEAF 0 0 0 0 GIANT FOXTAIL 0 0 0 0 BARLEY 0 0 0 0 TABLE A C'"MPD 77 CMPD 78 RATE=KG/HA 0.05 0.01 0.05 0.01 20 COTTON 0 0 0 0 MORNINGGLORY 0 0 0 COCKLEBUR -0 0 0 NUTSEDGE 0 0 0 0 CRABGRASS 0 0 0 0 BARNYARDGRASS 1 0 0 WILD OATS el10 0 0 WHEAT 0 0 0 0 CORN 0 q, 0 0 SOYBEANS 0 0 0 0 RICE 0 0 0 0 SORGHUM 0 0 0 0 CHEATGRASS 0 0 0 0 SUGARBEETS 2H 0 5G 0 VELVETLEAF 0 0 0 0 GIANT FOXTAIL 0 0 0 0 Bl\Rl.,EY 0 0 0 0 1 WO 89/00991 PCT/US88/02459 TABLE A CMPD CMPD 79

RATE=KG/HA

POSTEMERGENCE

COTTON

MORNINGGLORY

COCKLEBUR

NUTS EDGE

CRABGRASS

BARNYARDGRASS

WILD OATS

WHEAT

CORN

SOYBEANS

RICE

SORGHUM

CHEATGRASS

SUGAR BEETS

VELVETLEAF

GIANT FOXTAIL

BARLEY

0.05 0.01 0.05 loc loc loG 5C, 9G 9C 3C, 9G 5C, 9G 9C 9C 9C loG 6C, 9G 9C 9C loc 9C 9C 1 oc loc 5C, 9G 3C, 7G 9C 9G 5C, 9G 4U, 9G 9C 9C 4C, 9G 5C, 9G 9C loc 9C 5C, 9G 9C loc 9C 9C 3C, 8G 9C 3C, 8G 3C, 9G 3C, 7G 5C, 9G 9C 3C, 9G loc loc 9C 9C 2C, 9G 0.01 9C 5C, 9G 5C, 9G 8G iC 3C, 9H 3C, 8G 9G 5C, 9H 3C, 8G 4C, 9G 2C, 9G 5C, 9G 4C, 8H 4C, 8G 7G TABLE A CMPD 79 RATE= KG/HA

COTTON

MORN INGGLORY

COCKLEBUR

NUTSEDGE

CRABGRASS

BARNYARDGRAS S WILD OATS

WHEAT

CORN

SOYBEANS

RICE

SORGHUM

CHEATCRASS

SUGARBEETS

VELVETLEAF

GIANT FOXTAIL

BARLEY

0 .05 9C lOC qH 10E 3C, 7G 9H 4C, 8G 10H 10H 9H ],0E 5C, 9G 9H 9G 4C, 9G 9H- 9H 0.01 3C, 9G 9H 8H 10E 3C, 8G 3C, 7G 3C, 7G 2C, 8G 2C, 9G 9H 9G 3C, 9G 8G 4C, 9G 4C, 9G 3C, 8G 9G CMPD 0.05 3C, 8H 5C, 9G 9H 9G 8H 3C, 7G 3C, 7G 2C, 9G 3C, 7H 9H 10H 5C,9G 3C, 8G 5C, 9G 3C, 9H 3C, 7G 3C, 9G 0.01 8G 2C, 2C, 2H 0 0 3C, 7G 2C, 2G 6G 3G 3C, 6H 4G 3Q, 7H 7G 7G iC 3G 2C, SG WO 89/00991 WO 8900991PCT/US88/02459 152 CMPD 8 1 TABLE A CMPD 82

RATE=KG/HA

POSTEMERGENCE

COTTON

MORN INGGLORY

COCKLEBUR

NUTSEDGE

CRABGRASS

BARNYARDGRASS

WILD OATS

WHEAT

CORN

SOYBEANS

RICE

SORG HUM

CHEATGRASS

SUGARBEETS

VELVETLEAF

GIANT FOXTAIL

BARLEY

0.05 5C, 9G 10 C 5C, 9H 6C, 9G 3C, 7G 9C 6C, 9G 9G 0 9C 9C 5C, 9G 4C, 9G 9c 9C 5C, 9G 8G 0.01 5C, 9G boc 4C, 9G 2C, 9G 3C, 6G 4C, 9H 2C, 8G 9G 0 5C, 9G 5C, 9G 9G 3C, 7G 4C, 9G 4C, 9H 3C, 8G 6G 0.05 SC, 9G loc loc loc 5C, 8G 9C 4C, 9G 9G 0 4C, 8~H 9C 9C 5C, 9G lOC 4C, 9G 9C 3C, 9G 0.01 5C, 9G loc 9C 5C, 9G 3C, 7G 4C, 9G 6G 9G 0 2C, 7H 5C, 9G 5C, 9G 8G 4C, 9H 2C, 8G 9G 8G TABLE A

RATE=KG/HA

PREEMERGENCE

COTTON

MORN INGGLORY

COCKLEBUR

NUTSEDGE

CRABGRASS

BARNYARDGRASS

ILD OATS

WHEAT

CORN

SOYBEANS

RICE

SORGHUM

CHEATGRASS

SUGARBEETS

VELVETLEAF

GIANT FOXTAIL

BARLEY

CMPD 81 0.05 9G 9H 9 H 10E 9H 3C, 8H- 4C, 7G 2 C, 9 H 2C, 3G 10E 5C, 9G 9H 4C, 9G 5C, 9G 9H 4C, 8G CMPD 82 0.01 0.05 3C, 7H 3 C, 4 H 3C, 7H 9G 5G

'C

3C, 5G 6G 0 4C, 7H 3C, 7G 3C, 8G 3C, 8H 3C, 7H 3C, 7H 2C, 3G 2G 9G

PG

9H 10E 8H 9H 3C, 5G 8G 3G 4C, 8h-1 10E 4C, 9G 9H 9G 4C, 9H 3C, 8G 2C, 9G 0. 02 9G 2C, 8,H 8H- 9G 0 2C, 3G 1C 0 0 3C, 6H 9H 4C, 9G 8G 8G 3C, 5H1 2C, Ip-, WO 89/00991 PCT/US88/02459 153 CMPD 83 TABLE A CMPD 84

RATE=KG/HA

POSTEMERGENCE

COTTON

S MORNINGGLORY

COCKLEBUR

NUTSEDGE

CRABGRASS

BARNYARDGRAS S WILD OATS

WHEAT

CORN

SOYBEANS

RICE

SORGHUM

CHEATGRASS

SUGARBEETS

VELVETLEAF

GIANT FOXTAIL

BARLEY

0.05 0.01 3C, 9H loc 5C, 9G 2G 4C, 8H SC, 9G 3C, 9G 2C, 9G 4U, 9G SC, 9G 9C 9c 6C, 9G 9C 3C, 7H 5C, 9G 4C, 9G 8H 3C, 8H 3C, BI 0 3G 4C, 9G 3C, 7G 2C, 9G 3U, 9G 3C, 8H SC, 9G 4C, 9G 7G 3C, 7H- 3C, 411 3C, 8G 8G 0.05 4C, 9G 4C, 9G 4C, 9G 2C, 5G SC, 9G 9C 5C, 9G 2C, 9G 9C SC, 9H 9C 9C 9C boc 3C, 7H 6C, 9G 5C, 9G 0.01 2C, 3H 5C, 9G 3C, 7H 4G 2C, 3G 4C, 9G 3C, 7G 9G 4U, 9G 4C, 8G 9C 4C, 9G 9c SC, 9G 2H 3C,8BG 8G TABLE A CMPD 83

RATE=KG/H-A

2QPREEMERGE

NCE

COTTON

MORN INOGLORY

COCKLEBUR

NUTSEDGE

CRABGRASS

BARNYARDGRAS S WILD QATS

WHEAT

CORN

SOYBEANS

RICE

SO1MG UM

CI-EATGRASS

SUGARBEETS,

VELVETLEAF

GIANT FOXTAIL

BARLEY

0.05 0101 3G 3C, 31i 0 3C, 7H- 7G 7G 3C, 9G 4C, 8K I0E 3C, 9G 8G 2Ct 4H ic 2C, 7G 4C, 8H 0 0 0c 0 0 0 0 0C S 2C, 5G 6G 3C, 8a 0 0 0 2G CMPD 84 0.05 2C, 3G 2C, 6H 2 C, 2 H 0 3G 3C, $G 3C, 4G 7G 2C190 3C, 7 10H 4C, 9G 8G 2C, 4G 0

G

2C, 9G 0.01 0 4G 0 0

Q

0 0 0 2G 3C, 9G 0 4G 0 0 3G WO 89/00991 PCT/US88/02459 154 TestB Postemerence Three round pans (25 cm diameter by 12.5 cm deep) were filled with Sassafras sandy loam soil.

One pan was planted with nutsedge (Cyperus-rotundus) tubers, crabgrass (Dpjitaria sanguinalis), icklepod I.Ca faol~~rolia),I jimsonweed (Datura straiun~ velvetleaf (Abutilon th liPrasti), lambsquarters (ChenoPodium album), rice z saiva), and teaweed spinosa). The second pot was planted with green foxtail (5e.Lar viridis), cocklebur (Xanthium Persylvanicum), morningglory (Ipomoea hederacea), !otton (G.osyipum hirsutuW, johnsongrass (Sortugm ha-lepns), barn'-ardgrass (Echinohloa gcrus-aalli), corn (Zea mys), soybean (glcine mx), and giant foxtail (Setari-a faberi), The third pot was planted with wheat (Triticum aestivuir), barley (Hordeun vulgarl)t wild buckwheat (.q1yigonum convolvuls), cheatgrass (Bromus secalinus) or downy brome (Bromus tecitir), sugarbeet (Beta vgularia), wild oat (Avena comon chickweed (Stellrip- medi) or field violet (Viola arvenis) blackgrass (A~gpg.giar114 voysulrida) id rape (B ras xnapus) The plants were grown for approximately fourteen days, then sprayed postemergence with the chemicals dissolved in a nonphytotoxic solvent, PreeMergence Three round pans (25 cm diameter by 12,5 cm deep) were filled with Sassafras sandy loam soilk One pan was planted with nutsedge tubers, crabgrass, sicklepod, jimsonweed, velvetleaf, lambsquarters rice, and teaweed, The second pot was planted with green foxtail, cocklebur morningglory, cotton, johnsongrass, barnyardgrass, corn, soybean, and giant S-n- -'II~I~II WO 89/00991 1PCT/US88/02459 foxtail. The third pot was planted with wheat, barley, wild buckwheat, cheatgrass or downy brome, sugarbeet, wild oat, chickweed or field violet, blackgrass, and rape. The three pans were sprayed preemergence with the chemicals dissolved in a non-phytotoxic solvent.

Treated plants and controls were maintained in the greenhouse for approximately 24 days, then all rated plants were compared to controls and visually rated for plant response.

Response ratings are based on a scale of 0 to 100 where 0 no effect, and 100 complete control.

A dash response means no test.

Response ratings sre contained in Table B.

WO 89/00991 PCT/US88/02459 156 TABLE B CMPD 1 RATE-G/HA 62 16 4 1

POSTEMERGENCE

GIANT FOXTAIL 30 0 0 0 VELVETLEAF 100 100 100 SUGARBEETS 0 100 100 100 CRABGRASS 30 0 0 0 TEAWEED 90 70 50 JIMSONWEED 100 100 70 RICE 60 50 30 0 COCKLEBUR 100 100 80 COTTON 100 100 80 3 BARNYARDGRASS 70 60 50 WILD OATS 0 0 0 0 MORNINGGLORY 100 100 100 WHEAT 30 0 0 0 SICKLEPOD 100 100 100 JOHNSONGRASS 70Q 60 50 NUTSEDGE 100 100 100 CORN 70 so 30 0 WILD BUCKWHEAT 100 100 80 BLAQKGRASS 90 80 7O RAPE 100 100 100 100 BARLEY 50 30 0 0 GREEN FOXTAIL 50 30 0 0 CHEATGRASS 60 50 3 0 0 LAMBSQUARTER 30 0 70 CHICPWEED 100 90 80 WO 89/00991 PCT/US88/02459

I

TABLE B CMPD 1 RATE =G/HA

PREEMERGENCE

GIANT FOXTAIL

VELVETLEA'

SUGARBEETS

CRABGRASS

TEAWFRED

J IMSONWEED

RICE

COCKLE BUR COTTONc

SOYBEANS

BARNYARDGRASS

WILD OATS

M~ORNINGGLORY

WHEAT

ISICXLEPOD

JOHNSONGRASS

NUTSEDGE

CORN

WILD BUCK~WHEAT

BLACKGRAS

RAPE

BARLEY

GREEN FOXTAIL

CHEATGRASS

LAMB SQUARTER

CHICKWEED

250 70 100 100 60 90 90 100 90 90 90 1,00 90 90 80 100 80 3,00 60 100 100 1,00 70 9cI.

90 100 100 62 50 f1 0 100 30 80 80 80 80 60 70 9 9 60 80 50 70 00 30 90 90 50 60 90 95 16 30 80 100 0 70 50 70 30 0 60 30 70 30 3 0 30 70 0 80 70 80 30 30 70 80 90 4 0 100 0 0 0 0 0 0 0

Q

0 s0 WO 89/00991 PCT/US88/02459 158 TABLE B CMPD 2 RATE-G/HA 62 16 4 1

POSTEMERGENCE

VELVETLEAF 100 100 100 SUGARBEETS 100 90 CRABGRASS 30 20 0 0 TEAWEED 90 70 30 JIMSONWEED 100 100 90 RICE 90 50 40 COCKLEBUR 100 100 70 COTTUN 100 90 60 SOYBEANS 100 100 100 BARNYARDGRASS 100 100 WILD OATS 80 70 4020 MORNINGGLORY 100 100 70 WHEAT 90 70 40 SICKLEPOD 100 100 JOHNSONGRASS 100 80 40 NUTSEDGE 100 100 60 CORN 90 80 WILD BUCKWHEAT 100 100 40 BLACKGRASS 90) 90 70 RAPE 100 100 BARLEY 80 70 50 GREEN FOXTAIL 80 70 4Q CHEATGRASS 90 70 50 LAMBSQUARTER 100 90 50 CHICKWEED 100 90 40 0 WO 89/6099191ABE PCT/US88/02459 CMPD 2 RATE=G/HA 62 16 4 1

?REEMERGENCE

GIANT FOXTAIL 100 90 40 VELVETLEAF 100 90 70 SUGARBEETS 100 100 90 CRABGRASS 70 40 0 0 TEAWEED 9u70 30 JIMSONWEED 100 80 4 0 RICE 100 90 80 COCKLEBUR 80 70 50 COTCON 100 70 50 SOYBEANS 90 80 60 BARNYARQGRASS 100 100 90 WILD OATS 80 50 30 0 MORNING(3LORY 100 80 WHEAT 90 60 30 0 SICKL2POD 80 40 JOHNSONGRASS 100 100 80 NUT58EDGE 100 40 CORN 100 50 40 WILD BUCKWHEAT 100 100 80 BLACKGRASS 100 90 40 RAPE 100 1%0 70 BARLEY 70 70 40 GREEN FOXTAIL 100 80 40 CHEATGRASS 100 90 70 LANBSQUARTER 100 100 100 CHICKWEED 100 90 80 ~*1A WO 89/00991 PCT/US88/02459 160 TABLE B CMPD 3 RATE=G/HA 62 16 4 1

POSTEMERGENCE

VELVETLEAF 100 100 80 SUGARBEETS 100 100 80 CRABGRASS 50 40O 20 0 TEAWEED 90 70 50 JIMSONWEED 100 90 80 RICE 90 80 80 COCKLEBUR 100 100 100 COTTON 100 90 80 SOYBEANS 100 100 100 100 BARNYARDGRA SS 100 100 90 WILD OATS 100 100 70 MORNINGGLORY 100 90 70 WHEAT 100 100 80 SICKLEPOD 100 100 JOHNSONGRASS 100 100 80 NUTSEDGE 100 100 70 CORN 10 0 100 90 WILD BUCKWHEAT 100 100 70 BLACKGRASS 100 90 80 RAPE 100 100 100 BARLEY 90 80 70 GREEN FOXTAIL 70 70 40 CHEATGRASS 90 90 70 LAMBSQUARTER 100 90 70 CHICKWEED 100 80D 50 WO 89/00991 PCT/US88/02459 161 TABLE B CMPD 3 RATE=G/HA 62 16 4 1

PREEMERGENCE

GIANT FOXTAIL 100 90 70 VELVETLEAF 100 100 90 SUGARBEETS 100 100 100 CRABGRASS 80 70 40 TEAWEED 90 80 40 JIMSONWEED 100 100 80 RICE 100 100 90 COCKLEBUR 90 80 80 SCOTTON 100 90 80 SOYBEANS 90 80 70 BARNYARDGRASS 100 100 90 WILD OATS 90 80 70 MORNINGGLORY 100 70 50 WHEAT 90 80 70 SICKLEPOD 90 80 50 0 JOHNSONGRASS 100 100 90 NUTSEDGE 100 100 80 CORN 100 100 70 WILD BUCKWHEAT 100 100 80 BLACKGRASS 100 90 90 RAPE 100 100 100 100 BARLEY 90 80 70 GREEN FOXTAIL 100 80 60 0 SCHEATGRASS 100 90 80 LAMBSQUARTER 100 100 100 CHICKWEED 90 90 80 WO 89/00991 PCT/US88/02459 162 TABLE B CMPD 4 RATE=G/HA 62 16 4 1

POSTEMERGENCE

VELVETLEAF 100 100 60 SUGARBEETS 100 100 CRABGRASS 20 0 0 0 TEAWEED 80 40 20 0 JIMSONWEED 100 100 80 RICE 50 40 20 COCKLEBUR 100 100 100 COTTON 90 80 50 0 SOYBEANS 100 50 20 0 BARNYARDGRASS 70 30 0 0 WILD OATS 30 0 0 0 MORNINGGLORY 100 100 80 WHEAT 50 20 1a 0 SICKLEPOD 90 90 40 0 JOHNSONGRASS 70 60 20 NUTSEDGE 100 100 70 CORN 50 40 20 0 WILD BUCKWHEAT 100 100 BLACKGRASS 70 40 RAPE 100 100 100 100 BARLEY 50 40 20 0 GREEN FOXTAIL 40 20 10 0 CHEATGRASS 80 50 20 0 LAMESQUARTER 100 100 CHICKWEED 90 1 WO 89/00991 PCT/US88/02459 163 TABLE B CMPD 4 RATE=G/HA 250 62 16 4

PREEMERGENCE

GIANT FOXTAIL 90 80 60 VELVETLEAF 100 100 80 SUGARBEETS 100 100 90 CRABGRASS 70 60 40 0 TEAWEED 90 90 70 JIMSONWEED 100 100 80 RICE 100 100 100 COCKLEBUR 90 90 80 S COTTON 100 90 60 SOYBEANS 80 70 50 BARNYARDGRASS 100 100 70 WILD OATS 70 70 20 0 MORNINGGLORY 100 100 90 WHEAT 50 30 20 SICKLEPOD 100 100 80 JOHNSONGRASS 100 90 70 NUTSEDGE 100 100 90 CORN 100 60 40 WILD BUCKWHEAT 100 100 90 BLACKGRASS 100 90 80 RAPE 100 100 100 BARLEY 80 70 40 GREEN FOXTAIL 90 80 50 CHEATGRASS 90 70 LAMBSQUARTER 100 100 100 CHICKWEED 90 80 L i Ir.ii-, 1. r it i_ L_~ WO 89/0099 1 PCT/US88/02459 164 TABLE B CMPD RATE=G/HA 62 16 4 V*

POSTEMERGENCE

VELVETLEAF 100 100 60 0 SUGARBEETS 100 100 80 CRABGRASS 20 0 0 0 TEAWEED 90 60 20 JIMSONWEED 100 100 80 RICE 10 0 0 0 COCKLEBUR 100 100 100 COTTON 90 80 80 SOYBEANS 100 100 100 BARNYARDGRASS 0 0 0 0 WILD OATS 0 0 0 Q MORNINGGLORY 100 100 60 WHEAT 30 30 20 SICKLEPOD 100 90 20 JOHNSONGRASS 20 0 0 0 NUTSEDGE 100 100 40 CORN 30 20 0 0 WILD BUCKWHEAT 90 90 60 BLACKGRASS 40 20 20 0 RAPE 100 100 90 BARLEY 10 0 0 0 GREEN FOXTAIL 10 0 0 0 CHEATGRASS 0 0 0 0 LAMBSQUARTER 100 100 100 CHICKWEED 90 80 70 WO 89/00991 PCT/US88/02459 165 TABLE B CMPD RATE=G/HA 250 62 16 4

PREEMERGENCE

GIANT FOXTAIL 90 40 10 0 VELVETLEAF 100 100 80 SUGARBEETS 100 lop 100 100 CRABGRASS 80 40 20 0 TEAWEED 90 80 50 JIMSONWEED 100 70 RICE 90 40 40 0 COCKLEBUR 90 80 70 COTTON 100 90 60 SOYBEANS 90 90 80 BARNYARDGRASS 100 70 40 WILD OATS 40 10 0 0 MORNINGGLORY 100 100 90 WHEAT 10 0 0 0 SICKLEPOD 100 90 90 JOHNSONGRASS 90 80 50 NUTSEDGE 1010 90 CORN 90 50 50 WILD BUCKWHEAT 100 100 BLACKGRASS 90 80 50 RAPE 100 100 100 BARLEY 40 30 10 0 GREEN FOXTAIL 90 40 20 0 CHEATGRASS 60 40 20 LAMBSQUARTER 100 100 100 CHICKWEED 100 90 80 WO 89/00991 PCT/US88/02459 166 TABLE B CMPD 6 RATE=G/HA 250 62 16 4

POSTEMERGENCE

VELVETLEAF 100 100 90 SUGARBEETS 100 100 100 CRABGRASS 10 .0 0 0 TEAWEED 90 60 40 JIMSONWEED 90 90 60 RICE 10 0 0 0 COCKLEBUR 100 100 80 COTTON 90 80 80 SOYBEANS 100 100 100 100 BARNYARDGRASS 40 20 0 0 WILD OATS 10 0 0 0 MORNINGGLORY 100 100 90 WHEAT 10 0 0 0 SICKLEPOD 100 90 80 JOHNSONGRASS 0 0 0 0 NUTSEDGE 100 100 40 CORN 50 WILD BUCKWHEAT 100 100 60 BLACKGRASS 50 30 20 0 RAPE 100 3,00 BARLEY 0 0 0 0 GREEN EOXTAIL 0 0 0 0 CHEATG,"ASS 30 0 0 0 LAMBSQUARTER 100 100 100 100 CHICKWEED 100 90 WO 89/00991 WO89/00991P CT/US 88/0245 9 167 TABLE B CMPD 6 RATE=G/HA 250 62 16 4

PREEMERGENCE

GIANT FOXTAIL 60 20 10 0 VELVETLEAF 100 100 60 SUGARBEETS 100 10D 100 CRABGRASS 50 30 0 0 TEAWEED 80 70 60 JIMSONWEED 90 80 40 RICE 60 40 20 0 COCKLEBUR 90 70 50 COTTON 100 100 70 SOYBEANS 90 80 70 BARNYARDGRASS 100 90 40 WILD OATS 10 0 0 0 MORNINGGLORY 100 90 90 WHEAT 10 0 0 0 SICKLEPOD 100 80 50 JOHNSONGRASS 50 50 30 NUTSEDGE 90 90 40 CORN 100 40 30 WILD BUCKWHEAT 100 100 100 BLACKGRASS 80 70 30 0 RAPE 100 100 90 BARLEY 20 0 0 0 GREEN FOXTAIL 60 20 0 0 CHEATGRASS 50 30 10 0 LAMBSQUARTER, 100 100 100 CHICKWEED 100 100 90 WO 89/00991 PCT/US88/02459 168 TABLE B CMPD 7 RATE=GtfHA 250i 62 16 4

POSTEMERGENCE

GIANT FOXTAIL 50 30 20 0 VELVETLEAF 100 100 90 SUGARBEETS 100 100 100 100 CRABGRASS 30 20 0 0 TEAWEED 90 90 80 JIMSONWEED 100 100 90 RICE 100 100 50 COCKLEBUR 90 40 20 0 COTTON 90 80 80 SOYBEANS 100 100 100 BARNYARDGRASS 90 70 50 WI1D OATS 50 40 30 MORNINGGLORY 100 100 90 WHEAT 0 0 0 0 SICKLEPOD 100 .100 100 JQHNSONGRASS, 60 40 30 0 NUTSEDGE 0 0 0 0 CORN 90 80 80 WILD BUCKWHEAT 100 100 100 100 BLACKGRASS 70 50 30 RAPE 90 90 50 BARlLEY 10 0 0 0 GREEN FOXTAIL 80 so 20 0 LAMBSQUARTER 100 100 100 9 CHICKWEED 100 90 80 DOWNYI BR~OME 60 40 20 0 WO 89/00991 PCT/US88/02459 169 TABLE B CMPD 7 RATE=G/HA 250 62 16

PREEMERGENCE

GIANT FOXTAIL 70 40 VELVETLEAF 100 90 SUGARBEETS 100 100 100 CRABGRASS 80 70 TEAWEED 100 90 JIMSONWEED 100 50 RICE 100 90 COCKLEBUR 80 30 0 COTTON 100 90 SOYBEANS 100 100 BARNYAROGRASS 100 80 WILD OATS 70 40 MORNINGGLORY 100 100 100 WHEAT 10 0 0 SICKLEP'OD 100 70 tOHNSONGRASS 50 50 CORN 100 100 WIELD BUCKWHEAT 100 100 100 BLACKGRASS 70 50 RAPE 90 90 BARLEY 30 20 GREEN FOXTAIL 90 80 LAMSSQUARTER 100 100 CHICKWEED 90 80 DOWNY BROME 90 60 WVO 89/00991 PGT/US88/02459 170 TABLE B QM PD 8 RATE=G/HA 250 62 16 4

POSTPEMERGENCE

GIANT EQ,'TAIT, 90 40 VR rE U3A F 100 100 100 100 SUjC.:'lRY3ETb 100 100 100 100 CR~ABGRASS 70 40 40 T1EAWEED 100 100 90 JIMSONWEED 100 1.00 90 RICE 50 40 30 COCKLEBUR 100 100 100 100 COTTON 100 100 100 SOYBEI NS 100 100 100 BARNYARDGRASS 100 100 100 WILD OATS 70 5k) 30 0 MORNINGGLORY 1.00 100 90 WHEAT 50 30 0 0 SICKLEPOD 100 100 90 JOH-NSONGRASS 90 80 40 Q NUTSEDGE 100 100 100 100 CORN 50 40 30 WILD BUCKWHEAT 100 100 100 aLACKGRA8S 90 70 50 RAPE 100 100 100 100 BARLEY 30 0 0 0 03REEN FOXTAIL 100 80 50 14iiMISQUARTER 100 100 90 CHIQKWEED 100 100 80 DOWNY 11ROME 90 70 60 WO 89/00991 PCT/US88/02459 ii TABLE B CMPD 8 RATE-G/HA 250 62 16 4

PREEMERGENCE

GIANT FOXTAIL 90 80 70 VELVETLEAF 90 70 50 SUGARBEETS 100 100 90 CRABGRASS 70 50 30 0 TEAWEED 90 70 50 JIMSONWEED 70 60 50 RICE 100 90 70 COCKLZBUR 90 70 50 COTTON 70 50 30 0 SOYBEANIS 90 80 60 BAR.PNYARDGRASS 90 80 50 WILD OATS 50 40 30 0 MORNINGGLORY 90 80 60 WHEAT 50 30 20 0 SICKt 3 EPOD 100 100 70 JOHNSONGRASS 70 50 30 0 NUTSEDGE 100 100 100, CORlN 90 60 0 0 WILD BUCKWHEAT 100 100 90 BLACKGRASS 80 70 60 RAPE 100 100 100 BARLEY 50 30 'IQ GREEN FOXTAIL 90 70 50 LAMBSQUARTER 100 90 80 CHICKWEED 100 100 90 DOWNY BROME 90 70 5630 WO 89100991 PCT/US88/02459 172 TABLE 8 CMPD 9 RATE=G/HA 250 62 16 4

POSTEMERGENCE

GIANT FOXTAIL 70 50 40 VELVETLEAF 100 100 100 SUGARBEETS 100 10,0 90 CRABGRASS 50 50 40 0 TEAWEED 100 100 90 JIMSONWEED 100 100 90 G0 RICE 90 80 40 0 COCKLEBUR 100 100 100 COTTON 100 100 90 SOYBEANS 100 100 90 BARNYARDGRASS 100 100 70 5 0 WILD OATS 70 50 30Q 0 MORNINGGLORY 100 100 100 WHEAT 60 30 0 0 SICKLEPOD 90 90 50 JOHNSONGRASS 90 80 60 NUTSEDGE 100 100 100 CORN 100 100 70 WILD BUCKWHEAT 100 100 100 100 BLACKGRASS 90 80 70 R~APE 100 100 100 100 BARLEY 60 30 0 0 GREEN FOXTAIL 100 100 70 LAMBSQUA1RTER 100 100 90 CHICKWEED 100 100 90 DOWNY BROME 100 70 50 WO 89/00991 PCT/US88/02459 173 TABLE B CMPD 9 RATE=G/HA 250 62 16 4

PREEMERGENCE

GIANT FOXTAIL 90 80 70 VELVETLEAF 90 70 50 SUGARBEETS 100 100 90 CRABGRASS 60 30 0 0 TEAWEED 90 80 50 JIMSONWEED F/0 80 70 RICE 100 90 60 COCKLEBUR 90 80 70 COTTON 80 40 0 0 SOYBEANS 90 80 50 BARNYARDGRASS 10.9 70 50 WILD OATS 70 50 30' 0 MORNINGGLORY 90 80 70 WHEAT 70 50 30 0 SICKLEPOD 90 7u50 JOHNSON'GRASS 90 70 50 NUTSEDGE 100 90 70 CORN 100 90 50 0 WILD 9UCKWHEAT 100 100 95 BLACKGRASS 1 C z 90 60 RAPE 100 100 95 BARLEY 60 40 20 0 GREEN FOXTAIL 100 90 60 LAMBSQUARTER 100 90 80 CHICKWEED 100 90 70 DOW~NY bXOME 100 90 60 WO 89/00991 14TBEB PCT/US88/02459 CMPD 11 RATE=G/HA 250 62 16 4

POSTEMERGENCE

GIANT FOXTAIL 70 40 40 VELVETLEA~F 100 100 100 SUGARBEETS 100 100 80 CRABGRASS 30 20 0 0 TEAWEED 100 80 80 JIMSONWEED 100 100 90 RICE 50 20 0 0 COCKLEBUR 100 100 100 100 COTTON 70 60 50 SOYBEANS 70 40 20 0 BARNYARDGRASS 100 70 20 WILD OATS 50 30 0 0 MORNINGGLORY 100 100 100 WHEAT 0 0 0 0 SICKLEPOD 70 60 30 0 JOHNSONGRASS 50 40 30 0 NUTSEDGE 100 100 100 CORN 50 30 10 0 WILD BUCKWHEAT 100 100 100 100 BLACKGRASS 60 30 0 0 RAPE 100 100 100 100 BARLEY 0 0 0 0 GREEN FOXTAIL 90 40 g0 LAMBSQUARTER 100 90 40 CHICKWEED 90 60 30 0 DOWNY BROME 70 50 30 0

I

WO 89/00991 TBEB PCT/US88/02459 175 CMPD 11 RATE=G/HA 250 62 16

PREEMERGENCE

GIANT FOXTAIL 80 70 VELVETLEAF 90 70 SUGARBEETS 100 100 100 CRABGRASS 30 0 0 TEAWEED 90 70 JIMSONWEED 90 70 RICE 100 90 COCKLEBUR 90 80 COTTON 70 30 0 SOYBEANS 30 0 0 BARNYARDGRASS 80 50 WILD OATS 40 0 0 MORNIN~GGLORY 90 80 WHEAT 0 0 0 SICKLEPOD 50 30 0 JOHNSONGRASS 50 30 0 NUTSEDGE 100 90 CORN 30 0 0 WILD BUCKWHEAT 100 100 100 BLACI(GRASS 90 60 RAPE 100 100 100 BARLEY 0 0 0 GREEN FOXTAIL 80 50 LAMBSQUARTER. 100 90 CHICKWEED 90 80 DOWNY BROME 70 50 WO 89/00991 PCT/US88/02459 TABLE B 176 CMPD 12 RATE=G/HA 62 16 4 1

POSTEMERGENCE

GIANT FOXTAIL 0 0 0 0 VELVETLEAF 100 100 90 SUGARBEETS 100 100 100 CRABGRASS 40 20 0 0 TEAWEED 90 60 40 JIMSONWEED 100 100 90 RICE 10 0 0 0 COCKLEBUR 100 100 100 100 COTTON 100 90 70 SOYBEANS 100 100 100 BARNYARDGRASS 0 0 0 0 WILD OATS 30 20 0 0 MORNINGGLORY 100 90 70 WHEAT 20 0 0 0 SICKLEPOD 100 80 40 JOHNSONGRASS 0 0 0 0 NUTSEDGE 100 50 30 0 CORN 40 20 0 0 WILD BUCKWHEAT 100 100 100 BLACKGRASS 50 40 20 0 RAPE 100 100 100 BARLEY 0 0 0 0 GREEN FOXTAIL 20 0 0 0 LAMBSQUARTER 100 60 40 CHICKWEED 100 100 90 DOWNY BROME 0 0 0 0 L WO 89/0099-1 PCT/US88/02459 177 TABLE B CMPD 12 RATE=G/HA 250 62 16

PREEMERGENCE

GIANT FOXTAIL 50 20 0 VELVETLEAF 100 90 SUGARBEETS 100 100 100 CRABGRASS 50 30 TEAWEED 100 s0 JIMSONWEED 100 90 RICE 80 50 COCKLEBUR 100 100 COTTON 100 90 SOYBEANS 100 100 BARNYARDGRASS 40 30 0 WILD OATS 30 0 0 MORNINGGLORY 100 100 100 WHEAT 0 0 0 SICKLEPOD 100 90 JOHNSONGRASS 40 20 0 NUTSEDGE 50 30 0 CORN 100 40 WILD BUCKWHEAT 100 100 100 BLACKGRASS 60 40 0 RAPE 100 100 100 BARLEY 20 0 0 GREEN FOXTAIL 70 50 LAIBSQUARTER, 100 100 CHICKWEED 90 85 DOWNY BROME 50 30 0 WO 89/00991 PCT/US88/02459 178 TABLE B CMPD 13 RATE=G/HA 250 62 16 4

POSTEMERGENCE

GIANT FOXTAIL 0 0 0 0 VELVETLEAF 100 100 100 SUGARBEETS 100 100 100 CRABGRASS 0 0 0 0 TEAWEED 100 80 60 JIMSONWEED 100 100 90 RICE 10 0 0 0 COCKLEBUR 100 100 100 COTTON 90 90 80 SOYBEANS 100 100 100 100 BARNYARDGRASS 30 10 0 0 WILD OATS 20 0 0 0 MORNINGGLORY 100 100 100 WHEAT 10 0 0 0 SICKLEPOD 100 100 90 JOHNSONGRASS 0 0 0 0 NUTSEDGE 100 40 20 0 CORN 40 20 0 0 WILD BUCKWHEAT 100 100 90 BLACKGRASS 20 0 0 0 RAPE 100 100 100 100 BARLEY 0 0 0 0 GREEN FOXTAIL 20 0 0 0 LAMBSQUARTER 100 100 80 S CHICKWEED 100 100 90 DOWNY BROME 40 20 0 0 w WO 89/00991 PCT/US88/02459 179 TABLE B CMPD 13 RATE=G/HA 250 62 16

PREEMERGENCE

GIANT FOXTAIL 50 20 0 VELVETLEAF 100 9.0 SUGARBEETS 100 100 100 CRABGRASS 50 20 0 TEAWEED 100 90 JIMSONWEED lCD 90 RICE 70 40 k KLEE3UR 100 90 CuiLTON 100 80 SOYBEANS 100 100 BARNYARDGRASS 40 20 0 WILD OATS Z40 20 0 MORNINGGLORY 100 100 WHEAT 0 0 0 SICKLEPOD 100 70 JOHNSONGRASS 40 20 0 NUTBEDGE 100 50 CORN 100 70 WILD BUCKWHEAT 100 100cl 100 BLACKGRASS 30 20 0 RAPE 100 100 100 BARLEY 0 0 0 GREEN FOXTAIL 50 30 0 LAMBSQUARTER 100 100 CHICKWEED 90 90 DOWNY BROME 60 30 0 WO 89/00991 WO 8900991PCT/US88/02459 TABLE B CMPD

RATE=G/HA

POSTEMERGENCE

VELVETLEAF

SUGARBEETS

CRABGRASS

TEAWEED

JIMSONWEED

RICE

COCKLEBUR

COTTON

SOYBEANS

BARNYARDGRAS S WILD OATS MORN INGGLORY

WHEAT

S ICKLEPOD JOHN SONG RAS S

NUTSEDGE

CORN

WILD BUCKWHEAT

BLACIKGRASS

RAPE

BARLEY

GREEN FOXTAIL CHEATGIRAS S

LAMBSQUARTER

CHICKWEED

62 .16 100 100 10 80 100 40 100 100 90 10 100 40 100 100 100 100 100 80 100 60 30 80 90 100 100 100 0 60 80 40 100 50 100 50 0 100 40 90 60 50 90 80 70 100 60 10 70 70 100 100 0 100 100 0 100 0 WO 89/00991 PCT/US88/02459 181 TABLE

B

CMPD RATE=G/HA 250 62 16 4

PREEMERGENCE

GIANT FOXTAIL 80 40 20 VELVETLEAF 100 100 70 SUGARBEETS 100 100 80 CRABGRASS 50 30 0 0 TEAWEED 90 80 40 0 JIMSONWEED 90 90 80 RICE 90 70 60 COCKLEBUR 90 80 70 COTTON 70 60 50 SOYBEANS 80 70 20 BARNYARDGRASS 100 100 50 WILD OATS 20 0 0 0 MORNINGGLORY 100 90 90 WHEAT 70 40 10 0 SICKLEPOD 100 90 JOHNSONGRASS 100 90 80 NUTSEDGE 90 70 60 CORN 80 70 10o WILD BUCKWHEAT 100 100 80 BLACKGRASS 90 90 40 RAPE 100 100 90 BARLEY 50 30 30 GREEN FOXTAIL 80 40 30 C0ICHEATGRASS 90 80 70 LAMBSQUARTER 100 100 100 CHICKWEED 100 100 90 WO 89/0099 1 PCT/US88/02459 182 TABLE B CMPD 23 RATE=G/HA 62 16 4 1

POSTEMERGENCE

VELVETLEAF 90 40 30 SUGARBEETS 100 90 70 CRABGRASS 20 0 0 0 TEAWEED 10 0 0 JIMSONWEED 90 70 30 0 RlCE 40 10 10 0 COCKLEBUR 90 80 50 COTTON 30 20 0 0 SOYBEANS 100 90 50 BARNYARDGRASS 90 80 40 0 WILD CATS 70 60 30 0 MORNINGGLORY 100 70 40 0 WHEAT 50 30 30 0 SICKLEPOD 30 JOHNSONGRASS 100 40 3,0 NUTSEDGE 30 30 20 0 CORN 100 70 30 0 WILD BUCKWHEAT 80 60 00 8LACKGRASS 70 30 30 0 RAPE 100 90 70 BARLE~Y 40 30 20 GREEN FOXTAIL 20 0 0 0 CHEATGRASS 80 40 0 0 LAt4BSQUARTER 100 100 4 CHICKWEED 70 60 0 WO 89/00991 WO 8900991PCT/US88/02459 TABLE B CMPD 23 RATE =G/HA

PREEMERGENCE

GIANT FOXTAIL

VELVETLEAF

SUGAR BEETS CRAB GRA SS

TEAWEED

JIMSON WEED

RICE

COCKLI~EBUR

COTTON

SOYBEANS

BARNYARDGRAS S WILD OATS

MORNINQGLORY

WHEAT

SICKLEPOD

JQH-NSNGRASS

NVT$EDQE

CORN

WILD BUCKWHEAT

ELACKGRASS

RAPE

BARLjEY GREEN FOXTAIL CfEATGRA4,S

LAMESQUARTER

CHICKMWED

250 100o 100 3,00 90 100 80 90 100 60 70 100 80 50 iQ 100 70 100 100 90 62 100 J100 100 100 100 100 WO 89/0099 1 PCT/US88/02459 TABLE B 184 CMPD RATE=G/HA 62 16 4 1

POSTEMERGENCE

GIANT FOXTAIL 30 0 0 0 VELVETLEAF 100 90 60 SUGARBEETS 100 100 100 CRABGRASS 30 0 0 0 TEAWEED 70 50 30 0 JIMSONWEED 100 90 70 so RICE 80 60 30 0 COCKLEBUR 87050 3 COTTON 100 80 60 SOYBEANS 100 100 90 BARNYARDGRASS. 70 50 30 0 WILD OATS 50 30 0 0 MORNINGGLQRY 100 100 90 WHEAT 40 20 0 0 SICKLEPOD 100 100 100 tOHNSONGRASS 70 50 30 0 NUTSEDGE 100 100 50 CORN 70 60 50 WILD BUCKWHEAT 90 70 50 BLACKGRASS 90 80 70 RAPE 100 100 100 100 BARLEY 50 30 0 0 GREEN FOXTAIL 50 30 0 0 CHEATGRASS 90 70 5Q LAMBSQUARTER 90 80 70 CHICKWEED 100 90 70 $0 WO 89/004991 PCTIUS88/02459 185 TABLE B CMPD RATE=G/HA 62 16 4 1

PREEMERGENCE

GIANT FOXTAIL 100 60 30 0 VELVETLEAF 100 60 30 0 SUGARBEETS 100 100 90 CRAkBGRASS 60 30 0 0 TEAWEED 60 30 0 0 JIMSONWE- M 80 60 50 60 0 0 COCKLEBUI, 60 50 40 COTTON 0 0 0 0 SOYBEANS 60 0 0 0 BARNYARDGRASS 60 30 0 0 WILD OATS 60 30 0 0 MORNINGGLORY 90 70 50 WHEAT 40 0 0 0 SICKLEPOD 100 90 30 0 JOHNSONGRASS 70 50 30 0 NUT$EDJE 90 50 30 0 0ON0 Q0 0 WILD BT;JCK'qHEAT 90 70 50 BLACKGRI 90 70 50 RAPE 100 90 70 BARLEY 60 30 0 0 GREEN FOXTAIL 70 50 310 0 CHEATGRASS 70 30 0 0 LAMBSQUARTER 100 100 100 100 CHICKWEED 100 90 70 WO 89/ 00991 PCT/US88/02459 186 TABLE B CMPD 26 RATE=G/HA 62 16 41

POSTEMERGENCE

VELVTETLEAF 100 100 50 SUGARBEETS 100 90 80 CRA8BC-RAS3S 70 3 0 20 TEAWEED 70 50 40 JIMSONWEED 100 90 80 RICE 90 80 70 COCKLEBUR 100 100 70 COTTON 100 90 40 SOYBEANS 100 100 100 BARNYARDGRASS 100 90 80 WILD OATS 80 70 40 MOR1NINGGLORY 100 100 80 WHEAT 90 70 30 SIC)KLEPOD 3,00 100 80 JQH1NSONGRASS 90 80 50 NUTSEDGE 100 100 70 CORN 100 co90 WILD BUCKWHEAT 100 50 BLACKGRASS 90 80 70 RAPE 100 100 90 BARLEY 80 70 50 GREEN FOXTAIL 90 80 30 0 CHEATGRASS 90 80 70 LAMBSQUARTER 90 80 60 CHICKWEED 90 50 -0 WO 89/00991 PCT/US88/02459 187 TABLE B CMPD 26 RATE=G/HA 62 16 4 1

PREEMERGENCE

GIANT FOXTAIL 100 9n. 60 VELVETLEAF 100 80 0 SUGARBEETS 100 90 90 CRABGRASS 90 50 50 0 TEAWEED 100 70 30 0 JIMSONWEED 100 90 80 140 RICE 100 90 80 COCKLEBUR 90 80 50 COTTON 90 50 30 0 SOYBEANS 80 60 20 BARNYARDGRASS 11,0 100 90 WILD OATS 80 70 50 2(l MQRNINGGLORY 100 90 50 WHEAT 80 50 JOHNSONGRASS 100 100 80 NUTSEDGE 90 40 30 CORN 100 50 30 WILD BUCKWHEAT 100 90 70 MACKGRASS o'0 90 80 R~APE 100 100 100 BARLEY 70 50 30 GREEN FOXTAIL 100 90 50 CHEATGRASS 100 90 80 LAMBSQUARTVR 100 100 90 CHICKWEED 100 90 80 WO 89/0099 1 PCT/US88/02459I CMPD 27 RATE=G/HA 62 16 4 1

POSTEMERGENCE

VELVETLEAF 100 90 70 SUGARBEETS 100 100 CRABGRASS 60 60 20 0 TEAWEED, 90 70 70 JIMSONWEED 100 100 40 0 RICE 100 100 70 COCKLEBUR 100 100 70 COTTON 100 90 50 SOYBEANS 100 100 100 BARNYARDGRASS 100 100 90 WILD OATS 80 70 60 MORNINGGLORY 90 80 70 WHEAT 80 70 70 SICKLEPOD 100 100 JOHNSONGRASS 100 100 80 NUTSEDGE 100 100 90 CORN 100 100o 60 WILD BUCKWHEAT 90 70 BLACKGRASS 100 90 80 RAPE 100 100 90 BARLEY 90 60 60 GREEN FOXTAIL 90 80 40 0 CHEATGRASS 90 90 90 LAMBSQUARTER, 80 70 40 0 CHICKWEED 100 90 20 WO 89/00991 PCT/US88/02459 189 TABLE

B

189 CMPD 27 RATE=G/HA 62 16 4 1

PREEMERGENCE

GIANT FOXTAIL 100 80 70 VELVETLEAF 90 90 80 SUGARBEETS 100 90 90 CRABGRASS 80 40 20 0 TEAWEED 90 80 50 JIMSONWEED 90 80 70 RICE 100 100 90 COCKLEBUR 90 80 70 S COTTON 90 70 50 SOYBEANS 80 60 50 BARNYARDGRASS 100 90 70 WILD OATS PO 70 60 MORNINGGLORY 80 70 WHEAT 100 80 60 SICKLEPOD 100 80 40 JOHNSONGRASS 100 90 80 NUTSEDGE 100 80 70 CORN 100 100 70 WILD BUCKWHEAT 100 80 70 BLACKGRASS 100 100 70 RAPE 100 100 80 BARLEY 80 70 40 GREEN FOXTAIL 100 80 60 CHEATGRASS 100 90 90 LAMBSQUARTER 100 100 90 CHICKWEED 90 90 80

'K

WO 89/00991 PCT/US88/01459 TABLE B CMPD 2 8

RATE=G/HA

POSTEMERGENCE

VELVETLEAF

kl UGARBEETS CRAB GRAS S TEA WEED J1ISONWEED R I CE C0CKLEt3UR

COTTON

SOYBEANS

BARNYARDGRAS S WILD OATS MORN INGGLORY

WHEAT

SICKLEPOD

JOHNSONGRASS

NUTSEDGE

CORN

WILD BUCKWHEAT BLACKGRAS S

RAPE

BARLEY

GREEN FOXTAIL

CHEATGRASS

LAMB SQUARTER

CHICKWEED

62 16 100 100 20 60 100 80 100 80 80 70 100 40 100 60 100 50 100 70 100 1, 0 40 90 70 40 100 100 100 0 0 0

_I

WO 89/0991 PCT/US88/02459 TABLE B CMPD 28

RATE=G/HA

PREEMERGENCE

GIANT FOXTAIL

VELVETLFAF

SUGARBEETS

CRABGRASS

TEAWEED

JIMSONWEED

RICE

COCKLEBUR

COTTON

SOYBEANS

BARNYARDGRASS

WILD OATS

MORNINGGLORY

WHEAT

SICKLEPOD

JOHNSONGRASS

NUTSEDGE

CORN

WILD BUCKWHEAT

BLACKGRASS

RAPE

BARLEY

GREEN FOXTAIL

CHEATGRASS

SLAMBSQUARTER

CHICKWEED

250 40 100 100 60 80 100 100 90 90 70 100 30 100 40 90 90 100 90 100 100 40 50 90 100 90 62 100 100

I

j_ WO 89/00991 PCT/US88/02459 TABLE B 192 CMPD 29 RATE~q/HA 62 16 4 1

POSTEMERGENCE

VELVETLEAF 100 100 SUGARBEETS 100 90 CRABGRASS 40 20 0 0 TEAV'.ED 90 80 20 JIMSONWEED 100 100 90 RICE 10 0 0 0 COCKLEBUR 100 100 9040 COTTON 90 90 70 SOYBEANS 100 100 100 BARNYARDGRASS 50 10 0 0 WILD OATS 40 0 0 0 MORNINGGLQRY 100 100 80 WHEAT 10 10 10 0 SICKLEPOD 100 100 100 JOHNSONGRASS 10 0 0 0 NUTSEDGE 100 20 CORN 90 50 10 0 WILD BUCKWHEAT 100 0 BLACKGRASS 90 80 70 RAPE 100 100 2,00 BARLEY 20 10 0 0 GREEN FOXTAIL 40 0 0 CHEATGRASS 30 0 D 0 LAMBSQUARTER. 100 100 s CHICKWEED 100 100 so0 WO 89/00991 PCT/US88/02459 TABLE B 193 CMPD 29 RATE=G/HA 250 62 16 4

PREEMERGENCE

GIANT FOXTAIL 80 70 20 0 VELVETLEAF 100 100 90 SUGARBEETS 100 10.0 100 CRABGRASS 70 60 30 TEAWEED 100 80 70 JIMSONWEED 100 90 80 R~ICE 90 40 10 0 COCKLEBUR 90 90 80 COTTON 100 100 90 SOYBEANS 100 100 80 BARNYARDGRASS 90 70 WILD OATS 20 0 0 0 MQRNINGGLORY 100 100 100 WHEAT 0 0 0 0 SICKLEPOD 100 100 90 JOHNSONGRASS 80 70 0 NOUTSEDUE 100 90 40 CORN 100 50 20 WILD BUCKWHEAT 100 100 9Q BLACKGRASS 90 80 70 RAPE 100 100 100 BARLEY 50 20 0 0 GREEN FOXTAIL 80 60 0 0 CHEATGRASS 80 50 30 LAMBSQUARTER 100 100 100 CHICKWEED 100 90 80 WO 89/00991 WO 8900991PCTF/US88/02459 TABLE B CMPD

RATE=G/HA

POSTEMERGENCE

VELVETLEAF

SUGARBEETS

CRABGRAS S

TEAWEED

J IMSONWEED

RICE

COCKLEBUR

COTTON

SOYBEAkNS

BARNYARDGRASS

WILD OATS~ MORN INGGLORY

WHEAT

SICKLEPOD

JOHNSONGRASS

NUTSEDGE

CORN

WILD BUCKWHEAT

BLACKGRASS

RAPE

BARLEY

GREEN FOXTAIL,

CHEATGRASS

LAMB SQUARTER

CHICKWEED

62 100 100 0 80 100 0 100 90 100 30 30 100 20 100 a1 100 40 100 30 100 20 0 20 100 100 16 100 100 0 60 80 0 100 80 100 10 90 20 100 0 40 30 100 10 0 0 90 1010 4 0 0 100 0 8U 0 0 0 0

I

WO 89/0099 1 PCT/US88/02459 195 TABLE

B

CMPD RATE=G/HA 250 62 16 4

PREEMERGENCE

GIANT FOXTAIL 40 20 0 0 VELVETLEAF 100 100 90 SUGARBEETS 100 1010 100 CRABGRASS 70 20 0 0 TEAWEED 90 80 70 JIMSONWEED 100 90 80 RICE 50 10 0 0 COCKLEBUR 90 80 70 COTTON 100 100 80 SOYBEANS 90 80 70 BARNYARDGRASS 100 80 50 0 WILD OATS 30 Q 0 0 MORNINGGLORY 100 100 100 100 WHEAT 1.0 0 0 0 SICKLEPOD 100 90 JOHNSONGRASS 70 40 0 0 NUTSEDGE 90 50 CORN 90 20 WILD BUCKWHEAT 100 100 90 BLACKGRASS 70 40 30 0 RAPE 100 100 100 BARLEY 20 0 0 0 GREEN FOXTAIL 40 10 0 0 CHEATGRASS 40 10 10 0 LAMBSQUARTER 100 100 50 CHICKWEED 100 90 WO 89/00991 fPCT/US88/02459 196 TABLE B CMPD 31 RATE=G/HA 250 62 16 4

POSTBMERGENCE

GIANT FOXTAIL 50 40 30 0 VELVETLEAF 10Q 100 70 SUGARBEETS 100 100 1.00 CRABGRASS 0 0 0 0 TEAWEED 70 50 30 0 JIMSONWEED 100 90 80 RICE 50 40 30 0 COCKLEBUR 100 90 80 COTTON 70 50 40 8OYBEANS 100 90 80 BARNYARDGRASS 80 7Q 50 WILD OATS 60 30 0 0 MORNINGGL.QRY 100 80 60 WHEAT 50 30 0 0 SICKLEPOD 90 7/0 60 JOHNSONGRASS 70 50 30 0 NtJTSEDGE 90 70 50 CORN 0 0 0Q WILD BUCKWHEAT 100 100 1100 BLACKGRASS 100 90 70 s0 RAPE 100 100 100 100 BARLEY 40 30 20 0 G~REEN FOXTAIL 50 40 30 0 LAMBSQUARTER 100 100 70 CHICKWEED 100 100 70 DOWNY OROME 70- 30 0 0 WO 89/0099 1 PCT/US88/ 02459 197 TABLE

B

CMPD 31 RATE=G/HA 250 62 16 4

PREEMERGENCE

GIANT FOXTAIL 70 50 30 0 VELVETLEAF 90 80 70 s0 SUGAIRBEETS 90 80 70 CRABGR~ASS '50 30 0 0 TEAWEE 50 30 0 0 JIMSCINWFED 9v 80 70 RICE 100 8 c 60 0 COCKLEBUR 90 80 70 COTTON 50 30 0 0 SOYBEANS 70 30 0 0 BARNYARDGRASS 100 50 30 0 WILD O1kj*S 70 50 30 0 MORNINGGLORY 90 80 70 WHEAT 30 0 0 0 SICKLEPOD 80 50 0 0 JOH-NSONGRASS 70 50 30 0 NUTSEDGE 100 90 70 CORN 70 50 20 0 WILD BUCKWH-EAT 90 80 70 13LACKGRASS 90 80 70 R Al E 100 100 90 *ARLEY 60 30 0 0 GREENi FOXTAIL 80 60 30 0 LAD4BSQUAFTER 100 90 80 CHICKWEED 90 80 70 DOWNY BROME 50 30 0 0 11 1 I.8 _L_11 0 6

L

9 9,tCZ ,-zxMAln$ibdouuPi jr)4,,J"J'f i ZAXMAnLSIOdONW'.)IrIHQ I3:J1.IV 'Id t 068L991SL t z~xMhnsi b d u wj 5p, pci ZZkXMnistrtdONWI~frIHaS4 3Elti 'd OL Id 01 l//ll 1.1 lll 1.25 1 1. 6 iiill~ IIIII~ l~~i p-I- r- 2 ii WO 89/00991

RATE=G/HA

POSTEMERGENCE

GIANT FOXTAIL

VELVETLEAF

SUGARBEETS

CRABGRASS

TEAWEED

JIMSONWEED

RICE

COCKLEBUR

COTTON

SOYBEANS

BARtNYARDGRASS WILD OATS

MORNINGGLORY

WHEAT

SICKLEPOD

JOHNSONGRASS

NUTSEDGE

CORN

WILD BUCKWHEAT

BLACKGRASS

RAPE

BARLEY

GREEN FOXTAIL

LAMBSQUARTER

CHICKWEED

DOWNY BROME PCT/US88/02459 TABLE B CMPD 32 250 70 100 100 60 100 100 90 100 100 10 90 90 100 90 100 100 100 90 100 100 100 60 90 300 I100 100 62 50 100 100 50 90 100 80 100 100 90 80 60 100 70 100 100 90 80 1.00 100 100 50 70 90 100 100 16 30 100 90 40 80 90 70 90 80 80 70 30 90 50 90 90 80 70 90 100 100 40 50 70 100 95 4 0 0 100 0 100 WO 89/00991 PCT/LJS88/02459 199 TABLE B CMPD 32 RATE=G/HA 250 62 16 4

PFI]EMERGENCE

GIANT FOXTAIL 90 60 30 0 VELVETLEAF 90 80 70 SUGARBEETS 3.00 109' 100 CRABGRASS s0 50 30 0 TEAWEED 90 80 70 JIMSONWEED 100 100 90 RICE 100 100 90 COCKLEBUR 90 80 70 COTTON 90 80 60 SOYBEANS 90 70 50 0 BARNYARDGRASS 100 95 90 WILD OATS 90 8G 70 s0 MORNINGGLORY 100 90 80 WHEAT 90 70 50 SICKLEPOD 100 100 80 3'J JOHNSONGRASS 100 85 F~ NUTSEDGE 100 100 80 CORN 100 100 90 WILD BUCKWHEAT 100 90 80 BLACKGRASS 100 95 90 RAPE 100 100 100 'to0 BARLEY 90 170 60 GREEN FOXTA1L 90 60 30 0 LAMBSQUARTER 100 100 90 CHICKWEED 100 95 90 DOWNY BROME 100 100 100 WO 89/00991 PCT/US88/02459 TABLE B 200 CMPD 34 RATE=G/HA 250 62 16 4

POSTEMERGENCE

GIANT FOXTAIL snv 30 0 0 VELVETLEAF 100 100 90 SUGARBEETS 100 90 70 CRABGRASS 50 30 0 0 TEAWEED 80 70 50 JIMSONWEED 100 100 80 RICE 70 50 30 0 COCKLEBUR i00 100 90 COTTON 90 70 50 SOYBEANS 30 0 0 0 BARNYARDGRASS 80 50 30 0 WILD OATS 30 0, 0 0 MORNIrJGGLORY 100 100 90 WHEAT 0 0 0 0 SICKLEPOD 100 100 100 JOHNSONGRASS 70 50 30 0 NUTSEDGE 100 90 60 CORN 30 0 0 0 WILD BUCKWHEAT 100 100 100 BLACKGRASS 70 50 30 0 RAPE 100 100 100 100 BARLEY 50 30 0 0 GREEN FOXTAIL 50 30 0 C) LAMBSQUARTER 100 70 0 3 CHICKWEED L80 50 30 0 DOWNY B4ROME 100 80 70 ;CPL-I-DII~D~~-- i WO 89/00991 PCT/US88/02459 201 TABLE B CMPD 34 RATE=G/HA 250 62 16 4

PREEMERGENCE

GIANT FOXTAIL 30 0 0 0 VELVETLEAF 90 80 70 SUGARBEETS 100 100 90 CRABGRASS 40 20 0 0 TEAWEED 95 90 70 0 JIMSONWEED 100 90 80 RICE 100 90 60 COCKLEBUR 90 80 60 S COTTON 70 50 30 0 SOYBEANS 0 0 0 0 BARNYARDGRASS 50 30 0 0 WILD OATS 60 30 0 0 MORNINGGLORY 90 80 50 WHEAT 30 0 0 0 SICKLEPOD 70 50 30 0 JOHNSONGRASS 70 60 50 NUTSEDGE 100 90 70 0 CORN 80 30 0 0 WILD BUCKWHEAT 80 70 60 BLACKGRASS 90 70 50 RAPE 100 100 100 BARLEY 60 30 0 0 GREEN FOXTAIL 30 0 0 0 LAMBSQUARTER 100 90 80 CHICKWEED 90 70 50 DOWNY BROME 90 80 70 WO 89/00991 PCT/US88/02459 TABLE B CMPD RATE=G/HA 250 62 16 4

POSTEMERGENCE

GIANT FOXTAIL 30 0 0 0 VELVETLEAF 100 toO 100 SUGARBEETS 100 100 100 100 CRABGRASS 0 0 0 0 TEAWEED 100 90 80 JIMSONWEED 100 100 100 RICE 30 0 0 0 COCKLEBUR 100 100 100 100 COTTON 100 90 80 SOYBEANS 100 100 100 BARNYARDGRASS 60 0 0 0 WILD OATS 30 0 0 0 MORNINGGLORY 100 100 95 WHEAT 0 0 0 0 SICKLEPOD 100 100 JOHNSQNGRASS 70 50 0 0 NUTSEDGE 60 30 0 0 CORN 60 30 0 0 WILD BUCKWHEAT 100 100 100 100 BLACYGRASS 100 90 70 RAPE 100 100 100 100 BARLEY 0 0 0 0 GREEN FOXTAIL 50 30 0 0 LAMBSQUARTER 100 100 90 CHICKWEED 100 100 100 100 DOWNY BROME 70 300 0 WO 89/00991 PCT/US88/02459 TABLE B 203 CMPD RATE=G/HA 2 E,0 62 16

PREEMERGENCE

GIANT FOXTAIL 51) 30 0 VELVETLEAF 100 100 SUGARBEETS :l 0 0 100 100 CRABGRASS 50 30 0 TEAWEED 90 80 JIMSONWEED 100 100 RICE 50 30 0 COCKLEBUR 95 90 COTTON 100 70 SOYBEANS 100 90 BARNYARDGRASS, 50 30 0 WILD OATS 0 0 0 MORNINGGLORY 100 100 WHEAT 0 0 0 SICKLEPOD 90 80 JOHNSONGRASS 50 30 0 NUTSEDGE 70 60 CORN 100 90 WILD BUCKWHEAT 100 100 BLACKGRASS 80 70 RAPE 100 100 100 BARLEY 30 0 0 GREEN FOXTAIL 50 30 0 LAMBSQUARTER 100 100 CHICKWEED 100 100 100 DOWNY BROME 70 50 WO 89/00991 PCT/US88/02459 204 TABLE

B

CMPD 36 RATE=G/HA 250 62 1,6 4

POSTEMERGENCE

GIANT FOXTAIL 30 20 "o 0 VELVETLEAF 100 ",00 95 SUGARBEETS 100 l10D 10(0 CRABGRASS 50 20 (o 0 TEAWEED 100 80 8D JIMSONWEED 100 100 9(0 RICE 30 10 (D 0 COCKLEBUR 100 100 10.0 100 COTTON 90 90 8(o SOYBEANS 100 100 9"D 919 BARNYARDGRASS 70 40 2(0 0 WILD OATS 30 20 M0 0 MORNINGGLORY 100 100 10(0u WHEAT 10 0 0 0 SICKLEPOD 10 0 100 100 JOHNSONGRASS 20 0 0 0 NUTSEDGE 100 90 6-D CORN 60 20 (0 0 WILD BUCKWHEAT 200 100 10@0 BLACK(GRASS 40 30 2(0 0 RAPE 100 100 10(0 100 BARLEY 20 0 fl0 GREEN FOXTAILj 40 10 (D Ci LAMBSQUARTER 9to 70 7(0 CHICKWEED. 100 100 10(0 100 DOWNY BROME 40 20 (D 0 WO 89/00991 PCT/US88/02459 205 TABLE B CMPD 36 RATE=G/HA 250 62 16 4 PlREM17ERGENCE GIANT FOXTAIL 40 40 30 VELVETLEAF 100 90 40 SUGARBEETS 100 100 90 CRABGRASS 40 20 20 0 TEAWEED 100 100 50 JIM4SONWEED 90 80 30 RICE 60 40 0 0 COCKLEBUR 100 100 70 COTTON 100 100 30 SOYBEANS 100 100 20 0 BARNYARDGRASS 30 20 20 0 WILD OATS 20 0 0 0 MORNINGGLORY 1,00 100 80 WHEAT 0 0 0 0 SICKLEPOD 100 100 60 JOHNSONGRASS 40 30 20 0 NUTSEDGE 90 20 0 0 CORN 50 50 30 WILD BUCKWHEAT 100 100 100 BLACKGRASS 70 40 40 RAPE 100 100 100 BARLEY 20 0 0 0 GREEN FOXTA\IL 40 30 0 0 LAMBSQUARTER 95 90 80 CHICKWEED 100 90 70 DOWNY BROME 60 30 20 WO 89/00991 PC17US88/02459 206 TABLE B CMPD 37 RATE=G/HA 62 16 4 1.

POSTEMERGENCE

GIANT FOXTAIL 90 70 60 VELVETLEAF 100 100 90 SUGARBEETS 100 100 100 CRABGRASS 70 70 20) 0 TEAWEED 100 60 50 0 JIMSONWEED 100 90 80 RICE 100 100 COCKLEBUR 100 100 70 COTTON iCo 90 80Q SOYBEANS 100 100 90 B ARN YA RD GR A SS 100 100 100 WILD OATS 100 100 70 MORNINGGLORY 100 100 100 WHEAT 100 100 90 SICKLEPOD 100 .050 LOHNSONGRASS 100 100 90 PUTSEDGE 100 90 0 0 CORN 100 100 90 0 WILD BUCKWHEAT 100 100 90 BLACKGRAS S 100 100 70 RAPE 100 100 100 BARLEY 100 70 40 0 GREEN FOXTAIL 100 90 80 LAMBSQUARTER 100 100 90 CHICKWEED 100 100 80 DOWNY BROME 100 90 80

I

WO 89/00991 WO 8900991PCT/US88/02459 207 TABLE B CMPD 27

RATE=G/HA

PREEMERGENCE

GIANT FOXTAIL

VELVETLEAF

SUGARBEETS

CRABGRASS

TEAWEED

J IMSONWEED

RICE

COCKLEBUR

COTTON

SOYBEANS

BARNYARDGRASS

WILD OATS MORNINGGLOR';t

WHEAT

SICKLEPOD

JOHN SONGRAS S

NUTSEDGE

CORN

WILD BUCKWHEAT

BLACKGRASS

RAPE

BARLEY

GREEN FOXTAIL LAMB SQUARTER

CHICKWEED

DOWNY BROME 62 100 100 100 90 100 100 100 100 100 90 100 80 100 90 90 90 100 100 100 80 100 90 100 100 100 100 16 90 90 100 70 90 100 100 90 100 90 100 80 80 90 80 90 1oQ 100 70 100 90 10o 100 100 90 4 40 30 90 0 50 50 70 80 80 0 40 0 30 20 80 50 90 20 100 50 100 20 50 80 50 40 1 0 0 0 0 0 0 0 0 100 0 0 WO 89/00991 PCT/US88/024 59 208 TABLE B CMPD 38 RATE=G/HA 62 16 4 1

POSTEMERGENCE

GIANT FOXTAIL 60 50 30 0 VELVETLEAF 100 9,60 SUGARBEETS 90 b70 CRABGRASS 0 0 0 0 TEAWEED 80 70 50 2 JIMSONWEED 100 90 80 RICE 60 40 20 0 COCKLEBUR 80 30 0 0 COTTON 90 70 30 SOYBEANS 90 80 70 BARV'TARDGRASS 70 50 50 WILD OATS 80 70 40 0 MORNINGGLORY 90 7Q 70 WHEAT 90 90 70 SICKLEPOD 0 0 0 0 JOHNSONGRASS 60 50 40 NuTSEDQE 50 50 40 0 CORN 90 40 20 0 WILD BUCKWHEAT 70 50 30 BLACKGRASS, 90 80 70 RAPE 90 80 80 BARLEY 50 40 30 0 GREEN FOXTAIL 40 20 0 0 LAMESQUARTER 100 70 70 CHICKWEED 80 60 50 DOWNY BROME 80 60 50 0 WO 89/00991 PCT/US88/02459 209 TABLE B CMPD 36 RATE=G/HA 250 62 16 4

PREEMERGENCE

GIANT FOXTAIL 0 0 0 0 VELVETLEAF 40 30 0 0 SUGARBEETS 50 30 20 0 CRABGRASS 0 0 0 0 TFAWEED 40 40 0 0 JIMS0NWEED 50 0 0 0 RICE 30 20 0 0 COCKLEBUR 50 50 0 0 COTTON 0 0 0 0 SOY13EANS 0 0 0 0 BARNYARDGRASS 30 20 0 0 WILD OATS 50 30 30 0 MORNINGGLORY 50 0 0 0 WHEAT 30 0 0 0 SICKLEPOD 50 50 0 0 JOHNSONGRASS 30 0 0 0 NU-rSEDGE 0 0 0 CORN 0 0 0 0 WILD BUCKWHEAT 90 50 BLACKGRASS 30 20 20 0 RAPE 40 3 G 30 0 BARLEY 0 0 0 0 GREEN FOXTAIL 40 20 0 LAMBSQUARTER 50 0 0 0 CHICKWEED 2100 30 0 0 DOWNY B.ROME 40 20 0 0 WO 89/0099 1 PCT/US88/02459 210 TABLE B %CMPD 3 9 RATE=G/HA 16 4 1

POSTEMERGENCE

GIANT FOXTAIL 95 50 20 0 VELVETLEAF 100 80 60 SUGARBEETS 100 100 90 CRABGRASS 50 20 0 0 TEAWEED 90 90 50 0 JIMSONWEED 100 90 70 RICE 100 70 40 COCKLEBUR 90 70 30 COTTON 90 70 30 0 SOYBEANS 200 90 80 BARNYARDGRASS 100 100 60 WILD OATS 90 90 50 MORNINGGLORY 100 90 7G WHEAT 90 90 80 SICKLEPOD 80 50 $0 0 JOHNSONGRASS 100 70 60 NUTSEDGE 100 100 100 CORN 40 20 0 0 WILD BUCKWHEAT 100 80 50 SLAC1KGRASS 100 100 70Q RAPE 100 100 100 BARLJ-,Y 90 70 30 2 0 GREEN FOXTAIL 100 70 40 0 LAMBSQUARTER 100 50 50 0 CHICKWEED 100 100 60 DOWNY BROME 90 80 00 WO 89/00991 PCT/US88/02459 211 TABLE B CMPD 39 RATE=G/HA 62 16 4 1

PREEMERGENCE

GIANT FOXTAIL 100 30 30 0 VELVETLJEAF 90 80 50 SUGARBEETS 100 80 50 0 CRABGRASS 70 30 30 0 *TEAWEED 60 40 0 0 JIMISONWEED 60 50 30 RICE 80 40 40 0 COCKLEBUR 80 30 30 0 COTTON 100 100 30 0 SOYBEANS 100 90 30 0 BARNYARDGRASS 100 100 0- WILD OATS 70 20 Q 0 MORNINGGLORY 100 0 0 0 WHEAT 70 20 0 0 SICKLEPOD 80 0 0 0 JOH-NSONGRASS 90 70 20 0 NUTSEDGE 100 100 50 CORN 40 20 0 0 WTLD BUCKWHEAT 100 100 100 BLACKGRASS 'I0 30 0 0 RAPE 100 040 50 0 BARLEY 90 30 30 0 GREEN FOXTAIL 100 80 40 LAMBSQUARTER 90 50 30 0 CHICKWEED 70 0 0 0 DOWNY BROME 100 40 Q 0 WO 89/00991 PCT/US88/02459 212 TABLE B CMPD RATE=G/HA 62 16 4 1

POSTEMERGENCE

GIANT FOXTAIL 100 40 20 0 VELVETLEAF 100 90 40 0 SUGARBEETS 100 90 80 CRABGRASS 40 20 0 0 TEAWEED 80 50 20 0 JIMSONWEED 100 100 80 RICE 90 80 30 0 COCKLEBUR 100 50 20 0 COTTON 90 50 20 0 SOYBEANS 80 80 20 BARNYARDGRASS 100 90 70 WILD OATS 90 70 30 0 MORNINGGLORY 100 100 50 0 WHEAT 90 90 50 SICKLEPOD 80 40 0 0 JOHNSONGRASS 100 s0 "T0 1 NtJTSEDGE 100 80 20 0 CORN 80 30 0 0 WILD BUCKWHEAT 100 100 50 BLACKGRASS 100 90 50 RAPE 100 100 100 BARLEY 80 50 40 GREEN FOXTAIL 90 70 20 0 LAMBSQUARTER 100 100 701% CHICKWEED 100 70 20 0 DOWNY BROME 90 70 30 0 WO 39/oO991 PCT/US88/02459 213 TABLE B CMPD RATE=G/HA 62 16 4 1

PREEMERGENCF,

GIANT FOXTAIL, 60 60 0 0 VELVETLEAF 100 50 40 0 *SUGARBEETS, 100 100 50 5 C CRABGRASS 100 7'0 60 TEAWEED 80 70 30 JIMSONWEED 90 30 0 0 RICE 100 100 30 COCMI L!BUR 90 80 4 0 0 COTTO3N 100 80 50 0 SPBEANS 90 60 0 0 BARNYARDGRASS 100 100 30 WILD OATS 90 60 30 0 MORNINGGLORY 100 70 70 0 WHEAT .50 30 0 0 SICKLEPOD 80 80 70 JOHNSONGRASS, 90 90 50 NUTSEDGE 90 70 CORN 40 30 0 0 WILD BUCKWHEAT 100 100 100 100 BLACKGRASS 90 50 0 0 RAPE 100 i00 70 BARLEY 70 50 0 0 GRlEEN FOXTAIL 1/0 90 LAMBSQUARTER 100 90 CHICKWEED 70 70 0 v DOWNY EROME 90 80 40 4 WO 89/00991 PCT/US 3/02459 214 TABLE B CMPD 41 RATE=G/HA 250 62 16 4

POSTEMERGENCE

GIANT FOXTAIL 100 80 50 VELVETLEAF 90 60 40 0 SUGARBEETS 100 100 80 CRABGRASS 70 60 40 TEAWEED 50 20 0 0 JIMSONWEED 90 r,0 80 RICE 100 100 90 COCKLEBUR 80 50 20 0 COTTON 60 50 0 SOYBEANS 100 90 80 BARNYARDGRASS 100 100 90 WILD OATS 100 100 90 MORNINGGLORY 110 100 50 0 WHEAT 100 3100 90 SICKLEPOD 80 30 0 0 JOHNSONGRASS 100 1.00 80 NUTSEDGE 40 0 0 0 CORN 100 100 80 WILD BUCKWHE4NT 100 40 30 0 BLACKGRASS 100 100 90 RAPE 100 90 90 BARLEY 90 60 60 2 REGREEN FOXTAIL 100 90 50 LAMBS9Q.JARTER 90 80 40 0 CHICKWEED 100 80 70 DOWNY BROME 100 100 90 4 WO 89/00991 PCT/U S88/02459 215 TABLE B CMPD 41 RATE=G/A'A 250 62 16 4

PREEMERGENCE

GIANT FOXTAIL 100 100 90 VELVETLEAF 100 40 40 SUGARBEETS 100 90 0 0 CRABGRASS 100 70 0 0 TEAWEED 80 50 30 0 J IMSONWEED 100 80 30 0 RICE 100 100 60 COCKLEBUR 90 70 40 0 COTTON 100 90 30 0 SOYBEANS 100 100 20 BARNYARDGRASS 100 100 50 0 WILD OATS 80 80 0 0 MORNINGGLORY 100 90 20 0 WHEAT 100 20 0 0 SICKLEPOD 90 80 30 JOHNSONGRASS 100 90 70 NUTSEDGE 20 0 0 0 CORN 100 90 40 0 WILD BUCKWHEAT 100 100 100 100 BLACKGRASS 100 70 50 RAPE 100 60 30 BARLEY 100 80 0 0 GREEN FOXTAIL 100 100 90 LAI4BSQUARTER 80 70 70 CHICKWEED 90 90 0 0 DOWNY BROME 100 100 90 WO 89/00991 PCT/US88/02459 216 TABLE B CMPD 42 RATE=G/HA 250 62 16 4

POSTEMERGENCE

GIANT FOXTAIL 100 50 40 0 VELVETLEAF 70 40 20 0 SUGARBEETS 100 100 100 CRABGRASS 90 20 20 0 TEAWEED 30 20 0 0 JIMSONWEED 100 90 80 RICE 100 100 90 COCKLEBUR 80 20 0 0 COTTON 80 30 30 0 SOYBEANS 100 70 60 0 BARNYARDGRASS 100 100 80 WILD OATS 100 100 100 MORNINGGLORY 90 90 80 WHEAT 100 100 90 SICKLEPOD 80 30 0 0 JOHNSONGRASS 100 100 70 NUTSEDGE 90 50 50 CORN 100 100 60 WILD BUCKWHEAT 100 90 50 0 BLACKGRASS 100 100 80 RAPE 100 100 90 BARLEY 100 100 80 GREEN FOXTAIL 100 50 40 0 LAMBSQUARTER 100 80 50 CHICKWEED 100 90 70 DOWNY BROME 100 100 90 WO 89/00991 WO 8900991PCT/US88/02459 TABLE B CMPD 42

RATE=G/HA

PREEMERGENCE

GIANT FOXTAIL

VELVETLEAF

SUGARBEETS

CRABGRASS

TEAWEED

J IMSON WEED

RICE

COCKLEBUR

COTTON

SOYBEANS

BARNYARDGRAS S WILD OATS

MORNINGGLORY

WHEAT

SI CKLEPOD

JOH-NSONGRASS

NUTS EDGE

CORN

WILD BUCKWHEAT

BLACKGRASS

RAPE

BARLEY

GREEN

FOXTAIL

LAMBSQUARTER,

CHICKWEED

DOWNY BROME 250 100 70 100 100 50 100 100 90 80 100 100 90 100 100 100 100 100 100 100 90 80 90 100 100 100 62 90 50 100 90 50 90 100 90 80 70 100 80 100 100 80 90 50 40 100 90 80 90 100 70 70 100 16 0 100 40 50 30 30 100 70 70 50 90 70 0 80 0 0 0 100 0 WO 89/00991 PCT/US88/02459 218 TABLE B CMPD 43 RATE=G/HA 62 16 4 1

POSTEMERGENCE

GIANT FOXTAIL 100 Th'o 60 VELVETLEAF 100 100 90 SUGARBEETS 100 100 100 100 CRABGRASS 90 40 20 0 TEAWEED 100 80 70 JIMSONWEED 100 90 80 RICE 100 100 90 COCKLEBUR 100 Be~ 300 COTTON 100 90 80 SOYBEANS 100 100 80 BARNYARDGRASS 100 100 100 WILD OATS 100 100 100 MORNINGGLORZY 100 100 80 WHEAT 100 100 90 SICKLEPOD 1o0 80 50 0 JOHNSONGRASS 100 100 80 NUTSEDGE 90 90 40 0 CORN 100 100 80 WILD BUCKWHEAT 100 100 100 BLACKGRASS 100 lop 90 RAPE 100 100 100 BARLEY 10Q 100 9 Q GREEN FOXTAIL 100 100 7 0 LAMESQUARTER, 100 100 70 CHICKWEED 100~ 100 90 DOWNY BROME 100 100 8 u WO 89'00991 PCT/US88/02459 219 TABLE B CMPD 43 RATE=G/HA 62 16 4 1

PREEMERGENCE

GIANT FOXTAIL 100 100 70 VELVETLEAF 100 100 90 SUGARBEETS 100 100 100 CRABGRASS 90 90 80 TEAWEED 100 100 80 JIMSONWEED 100 90 80 0 RICE 100 100 100 COCKLEBUR 100 100 70 0 COTTON 100 100 100 SOYBEANS 100 100 60 BARNYARDGRASS 100 100 80 WILD OATS 90 80 60 MORNINGGLORY 100 100 50 0 WHEAT 100 90 80 SICKLEPOD 100 100 90 JOHNSONGRASS 90 90 70 NUTSEDGE 100 100 80 CORN 100 100 0 0 WILD BUCKWHEAT 100 100 100 100 BLACKGRASS 90 80 70 RAPE 100 100 100 BARLEY 100 90 70 0 GREEN FOXTAIL 100 100 100 S LAMBSQUARTER 100 100 90 0 CHICKWEED 100 90 DOWNY BROME 100 100 90 _1 n r -I i WO 89/00991 PCT/U588/02459 220 TABLE

B

CMPD 49 RATE=G/HA 62 16 4 1

POSTEMERGENCE

GIANT FOXTAIL 100 100 50 VELVETLEAF 100 100 60 0 SUGARBEETS 100 100 100 CRABGRASS 100 50 40 0 TEAWEED 100 90 40 JIMSONWEED 100 100 90 RICE 90 70 20 0 COCKLEBUR 100 80 70 COTTON 100 90 90 SOYBEANS 100 90 70 BARNYARDGRASS 100 100 60 WILD OATS 80 70 50 MORNINGGLORY 100 100 90 WHEAT 50 50 40 SICKLEPOD 100 60 50 0 JOHNSONGRASS 100 90 80 NUTSEDGE 0 0 0 0 CORN 100 80 30 WILD BUCKWHEAT 100 100 90 BLACKGRASS 70 70 60 RAPE 100 100 100 BARLEY 80 7u 60 Z GREEN FOXTAIL 100 100 60 r LAMESQUARTER 100 90 90 CHICKWEED 100 90 80 DOWNY BROME 0 70 60 WO 89/0099 1 PCT/US88/02459 221 TABLE B CMPD 49 RATE=G/HA 62 16 4 1

PREEMERGFN'CE

GIANT FOXTAIL 90 80 80 VELVETLEAF 90 8 ct 50 SUGARBEETS 90 80 60 CRABGRASS 100 100 90 TEAWEE;D 100 90 70 JIMSONWEED 90 60 40 RICE 100 90 60 COCKLEBUR 90 s0 70 COTTON 70 40 SOYBEANS 90 40 10 0 BARNYARDGRASS 100 90 40 WILD OATS 60 40 40 MQRNINGCORY 100 90 40 WHE~AT 70 20 0 0 SICKLEPOD 100 90 40 JOHNSONGRASS 100 90 40 0 NUTSEDGE 90 80 30 CQORN 70 60 20 0 WILD BUCKWHEAT 100 90 80 BLACKGRASS 90 70 40 0 RAPE 100 90 20 0 BARLEY 80 30 20 Q GREEN FOXTAIL 100 90 70 LAMBSQUARTER 100 100 100 CHICKWEED 100 100 90 DOWNY BROME 90 40 20 0 WO 89/00991 PCT/US88/02459 222 TABLE B CMPD 52 RATE=G/HA 62 16 4 1

POSTEMERGENCE

GIANT FOXTAIL 50 30 0 0 VEJVETLEAF 100 70 40 SUGARBEETS 10Q 100 100 CRABGRASS 0 0 0 0 *TEAWEED 80 40 30 JIMSONWEED 100 100 90 RICE 0 0 0 0 COCKLEBUR 80 60 50 COTTON 100 70 30 0 SOYBEANS 100 90 50 0 BARN~YARDGRASS 90 80 70 WILD OATS 70 50 30 0 MORNINGGLORY 90 70 60 0 WH~EAT 70 50 30 0 SICKLEPOD 30 0 0 0 JOHNSONGRA4SS 90 80 70 NUTSEDGE 50 30 0 0 CORN 20 10 0 0 WILD BUCKWHEAT 100 90 80 BLACKGRASS 100 100 80 RAPE 100 100 90 BARLEY 50 30 0 0 GREEN FOXTAIL 0 0 0 0 LAMBSQUARTER 100 100 70 CHICKWEED 100 90 70 DOWNY BROME 70 50 30 0 WO 89/00991 PCT/US88/024159 223 TABLE B CMPD 52 RATE=G/HA 250 62 3,6 4

PREEMERGENCE

GIANT FOXTAIL 90 70 50 VELVETLEAF 70 50 30 0 SUGARBEETS 95 90 80 CRABGRASS 95 90 85 TEAWEED 90 70 50 0 JIMSONWEED 90 70 50 RICE 100 90 60 COCKLEBU}R 70 50 30 0 COTTON 70 50 20 0 SOYBEANS 60 30 0 0 BARNYARDGRASS 100 100 80 WILD OATS 40 30 0 Q MORNINQGLORY 80 50 30 WHEAT 80 30 0 0 SICKLEPOD 90 70 50 JOJNSONGRASS 90 80 70 NUISEDGE 100 100 50 CORN 100 80 30 0 WILD BUCKWHEAT 100 95 90 BLACFGRASS 100 90 80 RAPE 10Q 100 90 BARLEY 80 70 50 GREEN FOX2TAI1J 100 90 80 LAMBSQUARTER 100 100 90 CHI!CKWEED 100 90 60 DOWNY BROME 90 80 50 WO 89/00991 PCT/US88/02459 224 TABLE

B

CmPP 58 RATE=G/IIA 250 62 16 4

POSTEMERGENCE

GIANT FOXTAIL 72 30 0 0 VELVETLE AF 100 100 100 SUGARBEETS 100 100 100 100 CRABGRASS 40 30 0 0 TEAWEED 90 70 60 JIMSONWEED 100 1.00 70 RICE 70 60 50 COCKLEBUR 100 100 80 COTTON 80 70 50 SOYBEANS 100 100 100 100 BARNYARDUCRASS 90 70 60 WILD OATS 70 6Q 50 MORNINGGLORY 100 90 60 WHEAT 50 30 0 0 SICKLEPOD 100 100 100 JOHNSONGRASS 90 60 30 0 NUTSEDGE 100 100 100 CORN 100 80 70 WILD BUCKWHEAT 100 100 100 100 BLACKGRASS 100 100 80 RAPE 100 100 100 100o BAR~LEY 60 30 0 0 GREEN FOXTAIL 80 50 30 0 CHE4'kTGRASS 100 100 70 LAMB SQUAPTER 90 70 50 110 CHICKWEED 100 100 70 LWO 89/00991 PCT/US88/02459 225 TABLE B CMPD RATE=G/HA Ku 62 16 4

PIREEMERGENCE

GIANT FOXTAIL 100 l00 70 VELVETLEAF 100 90 60 SUGARBEETS 100 100 100 100 CRABGRASS 7Q 50 30 0 TEAWEED 90 80 70 JIMSONWEED 95 90 60 R ICE 100 100 70 COCKLEBUR 90 80 30 0 COTTON 90 80 70 SOYBEANS 100 90 60 0 BARNYARDGRASS 100 100 80 WIL.D OATS 90 70 50 MORNINGCLORY 100 90 60 WH-EAT 70 50 30 0 SICKLEPOD 90 8,0 50 310 JOHNSONGFRASS 90 80 7030 NUTSEDGE 100 2190 70 CORN 100 90 30 0 WILD BUCKWH-EAT 90 00 70 BLACKGRAS6 90 80 70 RAPE 100 100 60 BARLEY 50 30 0 0 GREEN FOXTAIL 100 90 60 CH-EATGRASS 100 70 60 LAMBSQUARTER 100 100 100 CHICKWEED 100 90 s0 WO 89/00991 PCT/1JS88/02459 226 TABLE B CMPD 56 RATE=b/HA 250 62 16 4

POSTEMERGENCE

GIANT FOXTAIL 0 0 0 0 VELVETLEAF 100 100 80 SUGARBEETS 100 100 100 100 CRABGRASS 0 0 0 0 TEAWEED 70 50 30 0 JIMSONWEED 100 100 90 RICE 50 30 0 0 COCKLEBUR 100 100 100 COTTON 70 60 50 0 SOYBEANS 100 100 90 BARNYARDGRASS 0 0 0 0 WILD OATS 0 0 0 0 MORNINGGLORY 100 100 100 WHEAT 0 0 0 0 SICKLEPOD "too 90 80 JOHNSONGRASS 0 0 0 0 NUTSEDGE 100 100 1007( CORN 0 0 0 0 WILD BUCKWHEAT 100 100 100 BLACKGRASS 50 30 0 0 RAPE 100 100 100 100 BARLEY 30 0 0 0 GREEN FOXTAIL 0 0 0 0 CHEATGRASS 30 0 0 0 LAMBSQUARTER 90 80 70 CHICKWEED 100 80 V) wo 89io"199 i WO a~~?99tPCT/US88/02459 227 TABLE B CMPD 56 RATE=G/HA 250 62 16 4

PREEMERGENCE

GIANT FOXTAIL 0 .0 0 0 VELVETLEAF 9v 70 50 SUGARBEETS J100 100 100 100 CRABGRASS 0 0 0 0 TEAWEED 80 60 50 JIMSONWEED 60 50 40 RICE C 0 30 0 0 COCKLEBUR 90 60 30 0 COTTON 70 50 30 0 SOYBEANS 100 90 30 0 BARNYAR',GRASS 30 0 0 0 WILD ,TS 30 0 0 0 MORMINGGLORY 90 80 70 WHEAT 0 0 0 0 SICJLEPOD 100 7 0 50 JOH-NSONGRASS 60 0 0 0 NUTSEDGE 100 100 0 0 CORN 0 0 0 0 WILD BUCKWHEAT 100 90 80 BLACKGRASS 70 50 30 0 RAPE 100 100 80 BARLEY 0 0 0 0 GREEN FOXTAIL 0 0 0 0 CHEATGRASS 30 0 Q0 LAMBSQUARTER 100 100 90 CHICKWEED 90 80 70 1_ WO 89/00991 PCT/US88/02459 228 TABLE B CMPD 61 RATE=G/HA 62 16 4 1

POSTEMERGENCE

GIANT FOXTAIL 100 50 30 VELVETLEAF 100 100 100 SUGARBEETS 100 100 100 100 CRABGRASS 50 30 0 0 TEAWEED 100 90 50 JIMSONWEED 100 100 90 RICE 80 50 40 COCKLEBUR 100 100 80 COTTON 100 100 90 SOYBEANS 100 100 100 100 BARNYARDGRASS 100 40 20 0 WILD OATS 50 20 0 0 MORNINGGLORY 100 100 90 WHEAT 40 20 10 0 SICKLEPOD 100 100 100 JOHNSONGRASS 100 40 NUTSEDGE 100 100 100 100 CORN 90 80 70 WILD BUCKWHEAT 100 100 100 100 BLACKGRASS 90 90 50 RAPE 100 100 100 100 BARLEY 50 30 10 0 GREEN FOXTAIL 50 40 30 LAMBSQUARTER 100 90 90 CHICKWEED 100 100 100 DOWNY BROME 100 80 50 WO 89/00991 PCT/US88/02459 TABLE B CMPD 61

RATE=G/HA

PREEMERGENCE

GIANT FOXTAIL

VELVETLEAF

SUGARBEETS

CRABGRASS

TEAWEED

JIMSONWEED

RICE

COCKLEBUR

COTTON

SOYBEANS

BARNYARDGRASS

WILD OATS

MORNINGGLORY

WHEAT

SICKLEPOD

JOHNSONGRASS

NUTSEDGE

CORN

WILD BUCKWHEAT

BLACKGRASS

RAPE

BARLEY

GREEN FOXTAIL

LAMBSQUARTER

CHICKWEED

DOWNY BROME 250 40 90 100 90 100 100 80 80 90 90 100 70 100 40 100 80 90 60 100 80 100 80 80 100 100 90 30 90 100 80 90 90 80 80 90 70 90 70 100 20 90 40 50 90 70 100 50 80 100 100 80 0 80 90 70 90 50 40 40 60 60 90 10 90 30 80 30 90 40 100 30 60 90 100 40 4 0 0 0 0 100 L II WO 89/00991 WO 8900991PCT/US88/02459 230 TABLE B CMPD 62

ARATE=G/HA

POSTEMERGENCE

GIANT FOXTAIL

VELVETLEAF

SUGARBEETS

CRABGRASS,

TEAWEED

JIMSONWEED

RICE

COCKLEBUR

COTTON

SOYBEANS

BARNYARDGRASS

WILD OATS

MORNIJNGGLORY

WHEAT

SI CKLE POD

JOHNSONGRASS,

NUTSEDGE

CORN

WILD BUCKWHEAT

BLACKGRASS

RAPE

BARLEY

GREEN

FOXTAIL

LAMBSQUARTER.

CHICKWEED

DOWNY BROME 62 90 100 100 70 100 16.0 90 100 100 100 100 80 10&0 5*0 100 100 100 1.0 0 100 100 100 80 100 100 100 100 16 90 100 100 40.

100 100 60 100 100 100 100 60 100 40 100 100 100 100 100 90 100 70 100 90 100 100 4 1 50 100 100 30 90 100 50 100 100 100 100 40 100 20 70 90 100 100 100 60 100 30 80 80 .100 80 100 100 0 100 100

I

WO 89/00991 PCT/US88/02459 231 TABLE

B

CMPD 62 RATE=G/HA 250 62 16 4

PREEMERGENCE

GIANT FOXTAIL 100 60 50 VELVETLEAF 100 90 601 SUGARBEETS 100 100 90; CRABGRASS 100 90 70- TEAWEED 100 90 90 JIMSONWEED 100 100 90 RICE 100 80 70 COCKLEBUR 90 80 70 COTTON 90 90 501 SOYBEANS 90 70 50' BARNYARDGRASS 100 90 60 WILD OATS 80 70 60 MORNINGGLORY 100 100 90 WHEAT 90 70 60 SICKLEPOD 100 100 90 JOHNSONGRASS 100 90 40, NUTSEDGE 90 80 70' CORN 100 90 50 0 WILD BUCKWHEAT 100 90 80 BLACKGRASS 100 90 70 RAPE 100 100 100 BARLEY 90 90 70 GREEN FOXTAIL 100 100 90 S LAMBSQUARTER 100 100 100 CHICKWEED 100 100 100 100 DOWNY BROME 100 90 80 3 WO 89/00991 PCT/US88/02459 232 TABLE

B

CMPD 63 RATE=G/HA 62 16 4 1

POSTEMERGENCE

GIANT FOXTAIL 100 90 40 VELVETLEAF 100 10.0 100 SUGARBEETS 100 100 100 100 CRABGRASS 100 70 40 TEAWEED 100 100 100 JIMSONWEED 100 100 90 RICE 100 90 70 COCKLEBUR 100 100 100 COTTON 100 100 90 SOYBEANS 100 100 100 100 BARNYARDGRASS 100 100 100 WILD OATS 100 70 60 MORNINGGLORY 100 100 90 WHEAT 100 70 30 0 SICKLEPOD 100 100 80 JOHNSONGRASS 100 100 90 NUTSEDGE 100 100 100 CORN 100 100 90 WILD BUCKWHEAT 100 100 100 100 BLACKGRASS 100 100 70 RAPE 100 100 100 100 BARLEY 80 70 60 GREEN FOXTAIL 100 100 90 LAMBSQUARTER 100 90 70 CHICKWEED 100 100 100 DOWNY BROME 100 100 80 L WO 89/00991 PCT/US88/02459 233 TABLE

B

CMPD 63 RATE=G/HA 62 16 4 1

PREEMERGENCE

GIANT FOXTAIL 50 40 0 0 VELVETLEAF 80 8 0 60 SUGARBEETS 90 80 80 CRABGRASS 100 80 70 TEAWEED 90 90 80 JIMSONWEED 90 80 50 RICE 90 50 40 COCKLEBUR 90 80 70 COTTON 9G 60 40 SOYBEANS 80 60 20 BARNYARDGRASS 100 100 40 WILD OATS 60 50 50 MORNINGGLORY 100 90 70 WHEAT 80 70 40 SICKLEPOD 100 90 80 JOHNSONGRASS 90 60 30 0 NUTSEDGE 90 30 0 CORN 90 50 20 WILD BUCKWHEAT 90 90 BLACKGRASS 100 50 40 RAPE 100 90 90 BARLEY 90 80 40 GREFN FOXTAIL 100 90 30 0 LAMESQUARTER 100 100 100 CHICKWEED 100 90 DOWNY BROME 100 100 90 WO 89/00991 PCT/U588/02459 234 TABLE B CMPD 64 RATE=G/HA 62 16 4 1

POSTEMERGENCE

GIANT FOXTAIL 50 10 0 0 VELVETLEAF 100 100 90 SUGARBEETS 100 100 100 CRABGRASS 10 0 0 0 TEAWEED 100 90 JIMSONWEED 100 100 100 RICE 30 20 10 0 COCKLEBUR 100 100 100 COTTON 90 90 70 SOYBEANS 100 100 70 BARNYARDGRASS 90 50 30 WILD OATS 40 0 0 0 MORNINGGLORY 100 100 100 WHEAT 20 0 0 0 SICKLEPOD 100 70 50 0 JOHNSONGRASS 90 60 40 NUTSEDGE 100 100 100 COR~N 30 10 0 0 WILD BUCKWHEAT 100 100 100 100 BLAC~tGRASS 40 30 20 0 RAPE~ l00 100 100 100 BARbTEY 30 10 0 0 GREEN FOXTAIL 70 50 LAMBSQUARTER: 90 70 60 CHICKWEED 100 100 90 DOWNY EBROME 40 30 30 0 .jzD WO 89/0099 1 PCT/US88/02459 235 TABLE

B

CMPD 64 RATE=G/HA 250 62 16 4

PREEMERGENCE

GIANT FOXTAIL 40 0 0 0 VELVETLEAF 90 90 80 SUGARBEETS 100 9b 90 CRABGRASS 100 80 TEAWEED 90 90 80 JIMSONWEED 100 90 80 RICE 90 70 30 COCKLEBUR 90 70 70 COTTON 90 80 0 SOYBEANS 50 30 20 BARNYARDGRASS 80 40 20 0 WILD OATS 20 10 MOIRNINGGLORY 100 90 90 WHEAT 30 20 10 0 SICKLEPOD 100 80 JOHNSONGRASS 60 50 40 NUTSEDGE 100 100 90 CORN 70 20 10 0 WILD BUCKWHEAT 100 90 80 BLACKGRASS 70 60 30 0 RAPE 100 100 90 BARLEY 30 20 GREEN FOXTAIL 90 40 20 0 LAMBSQUARTER 100 100 100 CHICKWEED 100 100 100 DOWNY BROME 90 80 30 WO 89/00991 PCT/US88/02459 236 TABLE B CMPD RATE=G/HA 250 62 16 4

POSTEMERGENCE

GIANT FOXTAIL 100 90 20 0 VELVETLEAF 100 100 100 SUGARBEETS 100 100 100 100 CRABGRASS 60 40 0 0 TEAWEED 100 100 100 JIMSONWEED 100 100 100 100 RICE 40 30 10 0 1, COCKLEBUR 100 100 100 100 COTTON 100 100 90 SOYBEANS 100 100 100 100 BARNYARDGRASS 90 70 40 WILD OATS 30 10 10 0 MORNINGGLORY 100 100 100 100 WHEAT 10 10 0 0 SICKLEPOD 100 100 100 JOHNSONGRASS 60 50 30 0 NUTSEDGE 100 30 0 CORN 100 100 90 WILD BUCKWHEAT 100 100 100 100 BLACKGRASS 90 80 30 0 RAPE 100 100 100 100 BARLEY 40 20 10 0 S GREEN FOXTAIL 100 90 70 LAMBSQUARTER 100 100 80 CHICKWEED 100 100 100 100 DOWNY BROME 100 100 40 0

I

WO 89/00991 PCT/US88/02459 237 TABLE B CMPD RATE=G/HA 250 62 16 4 PREEMERG EN CE GIANT FOXTAIL 90 80 VELVETLEAF 100 90 70 SUGARBEETS 100 10 0 100 CRABGRASS 90 90 60 TEAWEED 100 100 90 4JIMSONWEED 100 100 90 RICE 70 40 10 0 COCKLEBUR 90 90 80 COTTON 90 80 70 SOYBEANS 100 90 50 BARNYARDGRASS 90 80 30 0 WILD OATS 50 40 30 MORNINGGLORY 100 10Q 90 WHEAT 10 0 0 0 SIQKLEPOD 100 100 90 JOHNSONGRASS 30 20 I0 0 NUTSEDGE 80 70 40 0 CORN 100 60 30 WILD BUCKWHEAT 100 100 100 BLACKGRASS 80 80 40 RAPE 100 100 90 BARLEY 60 40 20 0 GREEN FOXTAIL 100 90 50 LAMBSQUARTER 100 90 50 CHICKWEED 100 100 100 DOWNY BROME 70 40 30 wo 89/00991 PCT/US88/02459 TABLE F CMPD 66

RATE=G/HA

POSTEMERCENCF

GIA NT FOXTAglT V.'rLVETL EAF S £JGARBEETS

CRABGRASS

TEAWEED

JIMSONWEED

RICE

COCKLEBUR

COTTON

SOYBEANS

BARNYARDGRASS

WILD OATS

MORNINGGLORY

WHEAT

SICKLEPOD

JOHNSONGRASS

NUTSEDGE

CORN

WILD BUCKW44EAT

BLACKGRASS

RAPE

9ARLIEY G)R2N FOXTAIL LAMbSQUARTER CHICKW1EED DOW'1NY BROME 250 1,00 100 100 10 100 100 40 100 100 100 100 10 100 0 100 40 100 100 100 60 200 30 70 100 Q0 70 62 40 100 100 0 100 100 20 100 100 1'0 80 10 100 0 100 10 60 80Q 100 20 100 10 50 100 100 10 16 0 100 100 0 80 100 10 100 90 100 30 0 100 0 90 0 40 70 100 0 100 0 30 100 100 0 4 0 100 0 0 100 0 0 100 0 0 100 100 0 0 100 0 Li 1 WO 89/00991 PCT/US88/02459 239 TABLE B CMPD 66 RATE=G/HA 250 62 16 4

PREEMERGENCE

GIANT FOXTAIL 40 20 0 0 VELVETLEAF 100 91) 90 SUGARBEETS 100 100 100 CRABGRASS 90 80 30 0 TEAWEE) 100 90 70 JIMSONWE~ED 90 80 40 0 RICE 70 60 0 0 COCKLEBUR~ 90 80 80 COTTON 90 90 50 SOYBEANS 90 90 30 BARNYARI)GRA;-S 90 40 0 0 14ILD OATS 40 30 20 MORNINGGLORY 100 100 90 WHEAT 10 0 0 0 SICKLEPOD 100 90 50 4C JOHNSONGRASS 20 20 0 0 NUTSEDGE 80 50 0 CORN 100 80 20 WILD BUCKWHEAT 100 100 100 BLACKGRASS 60 30 20 0 RAPE 100 90 90 BARLEY 30 10 0 0 GREEN FOXTAIL 100 90 LAMBSQUARTER 100 90 N0 CHICKWEED 100 100 90 DOWNY BROKE 40 20 0 0 WO 89/00991 PeCT/US88/02459 240 TABLE B CMPD 67 RATE=G/HA 250 62 16 4

POSTEMERGENCE

GIANT FOXTAIL 10 0 0 0 VELVETLEAF 100 100 100 SUGARBEETS 100 100 100 100 CRABGRASS 20 0 0 0 TEAWEED 100 70 70 JIMSONWEED 100 100 80 RICE 60 40 10 0 COC2KLEBUR 100 100 100 /0 COTTON 90 90 80 SOYBEANS 100 100 100 100 BARNYARDGRASS 40 10 0 0 WILD OATS 20 0 0 0 MORNINGGLORY 100 90 70 WHEAT 0 0 0 0 SICKLEPOD 100 90 80 JOHNSONGRASS 40 30Q 30 0 NUTSEDGE 100 100 100 CORN 40 10 0 0 WILD BUCKWHEAT 100 100 100 100 BLACKGRASS 50 30 20 0 RAPE 100 100 100 100 BARLEY 20 0 0 0 GREEN FOXTAIL 30 0 0 0 LAM5SQUARTER 100 70 50 CHICKWEED 100 l00 100 DOWNY BROME 50 40 20 0 WO 89/00991 PCT/US88/02459 241 TABLE B CMPD 67 RATE=G/HA 250 62 16

PREEM'ERGENCE

GIANT FOXTAIL 0 0 0 VELVETLEAF 90 70 SUGARBEETS 100 90 CRABGRASS 40. 10 0 TEAWEED E80 70 JIMSONWEED 70 60 RICE 60 50 COCKLEBUR 80 70 COTTON 30 20 0 SOYBEANS 2Q 10 BARNYARDGRASS 110 10 0 WILD OATS 40 30 MORNINGGLORY 40 0 WHEAT 10 0 0 SICKLEPOD 80 70 JOHNSONGRASS 60 20 0 NUTSEDGE 9Q 90 CORN 100 0 WILD BUCKWHEAT 10C4 90 BLACKGRASS 100 40 0 RAPE 100 100 BARLEY 20 0 0 GREEN FOXTAIL 0 0 0 LAMB SQU4':'TER 90 90 CHICKWEED 100 100 DOWNY BROME 20 0 0 WO 89/00991 PC-./US88/02459 242 TABLE B CMPD 68 RATE=G/HA 250 62 16 4 P OSTEMERGENCE GIANT FOXTAIL 50 30 0 0 VELVETLEAF 100 100 100 SUGARBEETS 100 100 100 100 CRABGRASS 30 30 0 0 TEAWEED 100 90 50 JIMSONWEED 100 100 100 RICE 60 50 40 0 COCKLEBUR 100 100 80 COTTON 100 90 70 SOYBEANS 100 100 100 DARNYARDGRASS 100 80 40 0 WILD OATS 50 3.0 0 0 MORNINGGLORY 100 90 70 3 G WHEAT 20 10 0 0 SICKLEPOD 60 60 50 JOHNSONGRASS 90 50 NUTSEDGE 90 80 CORN 80 50 WILD BUCKWHEAT 100 100 90 BLACKGRASS 80 70 50 RAPE 100 100 100 100 BARLEY 30 10 0 GREEN FOXTAIL 60 40 20 0 LAMBSQUARTER 100 100 70 CHICKWEED 100 100 100 DOWNY BROME 80 70 70 WO 89/00991 PCT/US88/02459 243 TABLE B CMPD 68 RATE=G/HA 250 62 16

PREEMERGENCE

GIANT FOXTAIL 20 0 0 VELVETLEAF 50 4,0 *SUGARBEETS 90 90 *CRABGRASS 40 20 0 TEAWEED 90 70 JIMSONWEED 80 70 RICE 60 40 COCKLEBUR 90 50 0 COTTON 50 0 0 SOYB3EANS 20 10 BARNYARDGRASS 50 20 0 WILD OATS 60 50 MORNINGGLORY 80 70 WHEAT 140 10 0 SICKLEPOD 4G 0 JOHNSONGRASS 40 0 0 NUTSEDGE so 70 CORN 90 20 WILD BUCKWHEAT 100 90 BLACKGRASS 70 5o RAPE 100 90 BARLEY 60 30 GREEN FOXTAIL 40 0 0 LAMBSQUARTER 90 80 CHICKWEED 100 90 DOWNY BROME 70 30Q 0 WO 89/00991 PCT/US88/02459 244 TABLE B CMPD, 73 RATE=G/HA 62 16 4 1 P0 STEMERGENCE GIANT FOXTAIL 0 0 0 0 VELVETLEAF 90 70 50 SUGARBEETS 90 70 50 CRABGRASS 30 0 0 0 TEAWEED 50 30 0 0 JIMSONWEED 70 50 30 0 RICE 0 00 0 COCKLEBUR 90 70 50 COTTON 70 50 30 0 SOYBEANS 80 60 30 0 BARNYARDGRASS 0 0 0 0 WILD OATS 0 '0 0 0 MORNINGGLORY 80 70 50 WHEAT 0 0 0 0 SICKLEPOD 50 30 0 0 JOHNSONGRASS 0 0 0 0 NUTSEDGE 60 30 0 0 CORN 50 40 30 WILD BUCKWHEAT 80 70 50 BLACKGRASS 0 0 0 0 RAPE 100 80 50 BARLEY 0 0 0 0 GREEN FOXTAIL 0 0 0 0 CHEATGRASS 0 0 0 0 FIELD VIOLET 0 0 0 0 LAMBSQUARTER 50 30 0 0 WO 89/00991 PCT/US88/02459 245 TABLE B CMPD, 73 RATE=G/HA 250 62 16 4

PREEMERGENCE

GIANT FOXTAIL 50 30 0 0 VELVETLEAF 90 70 50 SUGARBEETS 90 70 50 CRABGRASS 60 30 0 0 TEAWEED 70 50 30 0 JIMSONWEED 80 50 30 0 RICE 60 30 0 0 COCKLEBUR 70 50 30 0 COTTON 40 20 0 0 SOYBEANS 50 30 0 0 BARNYARDGRASS 50 30 0 0 WILD OATS 50 0 0 0 MORNINGGLORY 70 50 30 0 WHEAT 0 0 0 0 SICKLEPOD 70 30 0 0 JOHNSONGRASS 30 0 0 0 NUTSEDGE 80 50 30 0 CORN 30 0 0 0 WILD BUCKWHEAT 90 70 s0 BLACKGRASS 60 30 0 0 RAPE 70 50 30 0 B3ARLEY 0 0 0 0 GREEN FOXTAIL 60 30 0 0 CHEATGRASS 60 30 0 0 LAMBSQUARTER 90 70 50 WO 89/00991 WO 8900991PCT/US88/02459 T~st C246 The Corn and Sorghum Herbicide Test included the following species in both the preemergence and postemergence evaluations: Category Crops Grasses Common Name Corn Soybean Sorghum Green foxtail Giant foxtail Johnsongrass Barnyardgrass Fall panicum Crabgrass Nut sedge Cocklebur DMorningglory Velvetleaf Jimnsonweed Lambsqua rters PigWeed Sma rtweed SPECIES Scientific Name Zea mays Glycine max Sorcihum bic.Qilo Setaria viridis Setaria faberii Sorgihum halecen Ecbnocloacrw- cal11i Panicum dichotomiflorum Digitan a sanciuinalis Cvcierus r-otundus Xa-nthium Pensylvanicum 1pomoea hederacea Abutilon theocihrasti Datura -stramonim Chenopodium album A~~tu erfej Polvcionum oerirrisq Broadleaves WO 89/00991 PCT/US88/02459 Postemerence 247 Postemergence plantings were grown in Sassafras sandy loam soil. Corn and soybeans were grown in separate 25 cm diameter containers. Sorghum and the seven grass weed species were grown in two 18 cm diameter containers, 4 species per container. The seven broadleaf weed species were also grown in two 18 cm diameter containers, 4 species in one container, 3 species in the second container. One iditional planting of corn in an 18 cm diameter container was made. The soil surface of this additional container of corn was covered with the absorbent, perlite, before spray treatment so that test chemicals would enter the plant only via the foliage. The plants were grown 10-21 days, dependent upon the species and then sprayed postemergence with the test chemicals dissolved in a nonphytotoxic solvent.

Preemergence Preemergence plantings were grown in fertilized Tama silt loam soil. These plantings are identical to those described in the postemergence section, with the exception of the corn planting having perlite covering the soil surface. These plantings were made the day of or the day before spraying the test chemicals dissolved in a nonphytotoxic solvent, EvaluatioQn Treated plants cid controls were maintained in the greenhouse for 2 to 4 weeks, Visual planting response ratings were made on a percentage scale of 0 to 100 in comprison with a control where 0 no injury, and 100 death. Response ratings are contained in Table C.

i. I i WO 89/00991 PCT/US88/02459 TABLE C CMPD 36 RATE GM/HA

POSTEMERGENCE

CORN

SOYBEANS

GREEN FOXTAIL GIANT FOXTAIL FALL PANICUM LARGE CRABGRASS

JOHNSONGRASS

SORGHUM

PURPLE NUTSEDGE

VELVETLEAF

COCKLEBUR

LADY SMARTWEED

LAMBSQUARTER

REDROOT PIGWEED IVY MORNINGLORY

JIMSONWEED

PERLITE CORN 125 40 100 0 0 0 0 35 25 70 100 100 100 100 100 100 100 25 64 32 16 8 4 2 20" 100 0 0 0 0 0 0 40 100 100 100 95 100 100 100 0 0 100 0 0 0 0 0 0 0 95 100 100 85 100 100 100 0 0 100 0 0 0 0 0 0 0 100 100 100 0 TABLE C CMPD 36 RATE GM/HA

PREEMERGENCE

CORN

SOYBEANS

GREEN FOXTAIL GIANT FOXTAIL FALL PANICUM LARGE CRABGRASS

BARNYARDGRASS

JOHNSONGRASS

SORGHUM

PURPLE NUTSEDGE

VELVETLEAF

COCKLEBUR

LADY SMARTWEED

LAMBSQUARTER

REDROOT PIGWEED IVY MORNINGLORY

JIMSONWEED

250 40 80 30 20 20 20 40 90 45 90 100 95 100 100 100 95 100 125 0 0 0 0 100 100 100 WO 89/00991 PCT/US88/02459 249 TABLE C CMPD 56 RATE GM/HA 125 64 32 16

POSTEMERGENCE

CORN 85 75 65 SOYBEANS 100 100 100 100 GREEN FOXTAIL 40 25 0 0 GIANT FOXTAIL 40 25 0 0 FALL PANICUM 45 25 0 0 LARGE CRABGRASS 0 0 0 0 BARNYARDGRASS 100 90 65 SJOHNSONGRASS 70 65 60 SORGHUM 90 85 70 PURPLE NUTSEDGE 100 100 70 VELVETLEAF 100 90 55 COCKLEBUR 100 80 65 LADY SMARTWEED 95 85 60 LAMBSQUARTER 55 25 0 0 REDROOT PIGWEED 100 100 95 IVY MORNINGLORY 50 20 0 0 JIMSONWEED 100 100 90 PERLITE CORN 70 60 55 TABLE C 20 CMPD 56 RATE GM/HA 250 125 64

PREEMERGENCE

CORN 0 0 0 SOYBEANS 40 30 0 GREEN FOXTAIL 20 0 0 GIANT FOXTAIL 20 0 0 FALL PANICUM 0 0 0 LARGE CRABGRASS 0 0 0 BARNYARDGRASS 0 0 0 JOHNSONGRASS 55 25 0 SORGHUM 0 0 0 PURPLE NUTSEDGE 0 0 0 VELVETLEAF 0 0 0 SCOCKLEBUR 0 0 0 LADY SMARTWEED 35 20 0 LAMBSQUARTER 40 30 0 REDROOT PIGWEED 60 35 0 IVY MORNINGLORY 0 0 0 JIMSONWEED 30 0 0 WO 89/00991 WO 89/099 1PCT/US88/02459 Weed species were planted 3 or 4 per diameter pot in Sassafras sandy loam (pH 6.8; 1% OM). Cotton was planted separately in the same sized pot. Postemergence plantings were made 12-16 days prior to ktreating so plants were in the 2- to 3-leaf stage (5-1Z cm tall), Preemergence plantings were made the (Jay before treating. Compounds were sprayed in a suitable nonphytotoxic solvent at 374 1/ha, then after 3 weeks of growth in a greenhouset plant responses were visually rated on a percent scale where 0 m no injury and 100 plant death. The following species were included: Depth 2 _,Common N-ae Cotton (Coker 315) Barnyardgrass Be rmdag ras s Broadleaf Slignalgras Crabgrass Fall panicun Goosegrass Johnsongrass Nutsedge Cocklebur Ivy leaf morninggiory Lambsquarters IPigweed Prickly sida PUrslane Sicklepod Smar tweed Velvetleaf Ground cherry The results ar~e shown La tLnN~me -Gossynium hirsutum Echlnochloa grMS-aagll1 Cynodon dactylon Brachiiaria Plptvo-hyvlla D i g-IAUianA i naA Panic um. .ibtQi o Sorghum halepense ~Perus rotundus Chenonodium alburj Arna ranthu1s retroflexus CypAn~~g a r i ao twf-1i Phvsalis heteronhvllA in Table Di

I

WO 89/0099 1 PCT/US88/02459 TABLE D CMPD 28 RATE GM/HA PRE EME R GEN CE

COTTON

REDROOT PIGWEED

LAMBSQUARTER

VELVETLEAF

PRICKLY SIDA

SICKLEPOD

COCKLEBUR

CMN PURSLANE IVY MORNINGLORY 0005 EG RAS S

BERMUDAGRASS

BARNYARDGRASS

jOHN SONG RASS FALL PAN ICUM LARGE CRABGRASS BRDLF SGNLGRASS PURPLE NUTSEDGE LADY SMARTWEED GROUND CHERRY 125 90 100 50 98 60 30 90 80 90 30 30 80 50 50 20 0 100 90Q 70 90 100 50 90 60 30 90 70 90 20 20 70 40 50 20 L00 90 60 32 100 0 0 0 0 0 0 WO 89/00991 PCT/US88/02459 Test E 252 Sixteen-cm-diameter Airlite plastic pots were partially filled with Tama silt loam soil and the soil saturated with water. Japonica and Indica rice seedlings at the 2.0 to 2.5 leaf stage were transplanted into 1/3 of the pots. Into another third of the pots were transplanted seedling or sprouted tubers of water plantain (Alisma trivale), Scripus (Scirpus paludosus), Cyperus (CY2yLP__r esculentus), and arrowhead (Sagittaria spp.), The remaining pots were planted with barnyardgrass (Echinochloa crus-galli) seeds and sprouted tubers of water chestnut (Eleochais spp,), These weeds all represent major rice weeds or genera of weeds important in rice. Three to four days after planting, the water level was raised to 3 cm (about 1200 l/pot) and maintained at this level throughout the test. Chemical treatments were applied directly to tha paddy water, within 24 hours of raising the water, after being formulated in a nonphytotoxic solvent, The pots were maintained in the greenhouse. Rates of application and plant response ratings made 21 days after treatment are summarized in Table E, WvO 89/00991 PCT/US88/02459 253 TABLE E CMPD 1 RATE-G/HA 16 8 4 2 BARNYARDGRASS 40 20 Q 0 WATERCHESTNUT 55 30. 0 0 ARROWHEAD 90 85 0 0 SCIRPUS 50 30 0 0 WATER PLAINTAIN 95 90 0 0 RICE JAPQN)'CA 65 30 10 0 RICE INDICA 20 0 0 0 TABLE E RATE=G/HA 125 64 32 1 8 BARNYARD'RASS 20 0 0 0 0 WATERCHE8TNUT 20 20 0 0 0 ARROWHEAD 90 80 65 0 0 SCIRPUS 0 0 0 0 Q YELLOW NUTSEDGE 30 0 0 0 0 WATER PLAINTAIN 85 70 65 0 0 RICE JAPONICA 20 0 0 0 0 RICE INDICA 20 0 0 0 0 TABLE E CM? D 8 RATE=G/HA 125 64 32 16 8 BARNYARDGRASS 80 75 50 0 0 WATERCHESTNUT 95 90 90 80 SCIRPUS 1100 100 100 100 YELLOW NUTSEDGE 90 8, 80 70 0 WATER PLAINTAIN 1.00 10f 98 95 RICE JAPONICA 75 Go 50 40 RICE INDICA 11 25 20 0 0 I~~W PCT/US88/02459 TABLE E CMPD 11

RATE=G/HA

BARNYARDGRASS

WATERCHiZSTNUT

SCIRPUS

YELLOW NUTSEDGE WATER PLAINTAIN RICE JAPONICA RICE INDICA 125 100 98 TABLE E CMPD 12

RATIE,=G/HA

IARNYARDGRASS

WATERCHESTNUT

SCIRPUS

YELLOW NUTSEDOE WATER PLAINTAIN RICE JAPONICA RICE INDICA TABLE E CMPD 13 RATE-G/liA

BARNYAROGRASS

WATERCHESTN"

SCIRPUS

YELLOW NUTSEl1E WATER PLA.INTA RICE JAPONICA RICE INDICA WO 89/00991 PCT/US8SS/02459 255 TABLE E CMPD 29 RATE=G/HA 250 125 64 32 16 8 4 BARNYARDGRASS 80 60 50 50 0 0 0 WATERCHESTNUT 75 65 60 30 0 0 0 ARROWHEAD 100 90 90 50 0 SCIRPUS 30 0 0 0 0 90 0 YELLOW NUTSEDGE 80 30 20 20 0 100 0 WATER PLAINTAIN 100 95 90 70 0 95 0 CMN ARROWHEAD 95 90 85 80 0 RICE JAPONICA 25 20 15 10 0 0 0 RICE INDICA 30 25 20 10 0 0 0 TABLE 0 CMPD RATE= /HA 125 64 32 16 8 BARNYARDGRASS 20 20 0 0 0 WATERCHESTNUT 0 0 0 0 0 ARROWHEAD 60 0 0 0 0 S(IRPUS 40 0 0 0 0 YELLOW NUTSEDGE 60 0 0 0 0 WATER PLAINTAIN 40 0 0 0 0 RICE JAPONICA 30 0 0 0 0 RICE INDICA 20 0 0 0 0 TABLE E CMPD 56 RATE=G/HA 125 64 32 16 8 BARNYARDGRASS 80 30 0 0 0 WATERCHESTNUT 95 85 75 0 0 ARROWHEAD 90 90 70 0 0 SCIRPUS 100 98 0 0 YELLOW NUTSEDGE 40 0 0 0 0 WATER PLAINTAIN 100 90 100 80 RICE JAPONICA 60 20 10 0 0 RICE INDICA 50 20 10 0 0 ~I Li i i WO 89/00991 WO 89OO99~PCT/US88/02459 256 TABLE E CMPD 61

RATE=G/HA

BARNYARDGRASS

WATERCHESTNUT

SCIRPUS

YELLOW NUTSEDGE WATER PLAINTAIN RICE JAPONICA RICE INDICA 64 70 80 100 100 100 55 20 32 50 8 0' 100 90 100 45 10 16 0 0 100 TABLE E CMPD 64 RATE =G/HA

BARNYARDGRASS

WATERCHESTNUT

SCIRPUS

YELLOW NUTSEDGE WATER PLAINTAIN RICE JAPONICA RICE INDICA 64 65 90 100 95 100 50 25 32 100 90 100 40 20 0 0 0 Izln~~~sl~~il- -I WO 89/00991 PCT/US88/02459 Test F 257 For the postemergence phase of the test, crop and weed species were planted in a Sassafras sandy loam soil (approximately 1% organic matter) one to three weeks before application so that they were present as young plants at the time of treatment.

Alterntively, for postemergence tests, plants were grown in a 50:50 mixture of commercially available potting mix and Sassafras soil. Plantings for the preemergence phase were made in a Tama silt loam soil (approximately 3% o:.ganic matter) the day before, or the day of treatment. Approximate planting depths were corn and soybeans 3 to 4 cm; morningglory, cocklebur, and nutsedge 2.5 to 3 cm; velvetleaf, sicklepot, and sesbania 2 cm; all other species cm.

The test chemicals were dissolved/suspended in a nonphytotoxic solvent in concentrations required to obtain the desired rate of application. The solutions or suspensions were then applied as soil/foliage sprays to the young plants (postemergence phase) and to the soil surfaces of the freshly planted containers (preemergence phase).

Application was made utilizing an automatic spray machine at a spray volume of 374 liters per hectare.

Immediately after treatment, the containers were transferred to a greenhouse and subsequently watered on a demand basis, taking care not to wet the foliage of the plants in the postemergence phase of the test.

The following species were included in the test: 1. -e L- i WO 89/00991 PCT/US88/Q1459

APPROXIMATE

GROWTH STAGE AT POST

APPLICATION

PLANT SPECIES SCIENTIFIC NAME :Lq~_Weeds: Ba rnyardgrass Giant foxtail Green foxtail Johnsongrass Fall panicum rn-tsedge Signaigrass Crabgrass Velvetleaf J ims onwe ed Hemp sesbania Sicklepod Cocklebur Ivyleaf morningglory Ladysthumb sma rtweed Pigweed Lambsquarters Teaweed black- 20 nightshade Echinochloa crus-aalli Setaria--faberi SEtaris viridis Sorghum halepense Panicum dichotorniflorurn Cyp.grus rotundus Brachiaria Platyphylla Dicgitaria sanciuiwk 1 i~a Abutilon theophrasi Datura sitramoniuqm Sesbania exaltata _C~a Qbtusifo_ije Xa~nthium penslvanigumn~ I P a moP.a h e' a Eo~lxnonum persicaria Amparianthuu retroflexus-a Ch~us\podium album Srlnurmim ntvcanthum 2-3 2-3 2-3 2-3 2-3 5-6 2-3 2-3 2--3 1-2 1st 1st 2nd leaves leaves le~aves leaves leaves leaves leaves leaves leaves true leaves true leaf true leaf true leaf 1-2 true leaves 3-4 4-5 4-5 2-3 2nrd leaves lenves leaves lea ves true leaf Corn (Funk G4 64 6) Soybeans (Williams) 2-3 leaves Gly-cine max 1st trifoliate Visual plant response ratings were made approximately two and four weeks after treatment for the post- and pre-emergence phases, respectively.

The ratings were made on a percentage scale of 0 to 200, where 0 =no injuryj and 100 -death of plants.

Plant response ratings are summarized in Table F.

WO 89/00991 PCT/US88/02459 259 TABLE F CMPD 28 RATE GM/H 250 125 64 32 16

PREEMERGENCE

SOYBEANS 40 0 0 0 0 CORN 20 10 10 0 0 VELVETLEAF 60 50 40 20 0 JIMSONWEED 70 70 40 0 0 *SICKLEPOD 40 20 0 0 0 HEMP SESBANIA 40 20 0 0 0 COCKLEBUR 75 50 30 0 0 IVY MORNINGLOPY 50 50 30 0 0 REDROOT PIGWEED 95 90 75 60 LAMBSQUARTER 100 80 60 50 PRICKLY SIDA 40 20 0 0 0 BARNYARDGRASS 50 20 0 0 0 GIANT FOXTAIL 20 0 0 0 0 GREEN FOXTAIL 0 0 0 0 0 JOHNSONGRASS 30 0 0 0 0 FALL PANICUM 40 20 0 0 0 LARGE CRABGRASS 0 0 0 0 0 BRDLF SGNLGRASS 0 0 0 0 0 PURPLE NUTSEDG8' 80 70 60 40 LADY SMARTWEED 85 75 60 40 BLACK NIGH-TSHAD 75 50 30 0 0 WO 89/00991 WO 8900991PCT/US88/02459 TABLE F CMPD 34 RATE GM/H

POSTEMERGENCE

SOYBEANS

CORN

VELVETLEAF

J IMSONWEED

SICKLEPOD

HEMP SESBANIA

COCK~LEBUR

IVY MORNINGLORY REDROOT PIGWEED LA4B SQUARTER PRICKLY SIDA

BARNYARDGRASS

GIANT FOXTAIL GREEN FOXTAIL JOHN SON GRAS S FALL PANICUM LARGE CRABGRASS BRDLF SGNLGRASS PURPLE NUTSEDGE BLACK NIGHTSHAD 125 64 32 16 8 A 20 40 80 80 50 98 100 100 98 50Q 0 50 30 30 50 ~30 0 50 80 95 0 30 70 60 30 90 100 100 90 30 0 40 0 0 30 0 0 30 70 85 0 50 50 50 70 70 100 80 20 0 30 0 0 0 0 0 0 60 80 0 0 0 100 0 0 0 0 0 0 0 0 0 containea in raoie u~.

WO 89/00991 PCT/US88/0249 The species below were planted.

Name Genus Species Size (cm), Blackgrass, Stage II Lambsquarters, Common Catchweed Beadstraw Russian Thistle Black Nightshade, Eastern Field Pennycress Ivyleaf Speedwell Field Speedwell, Common Field Pansy Algecurm.s-myosuroides Chenpodium album Gaiur rine Salsoa kali Solanum ni-grum Thlasni arvensea Veronica hederaefolia Veronica nersicA Viola arvensis 14 .0 4 .0 9 .0 Two days later, a second series were planted using the following species.

-Name n i qqnP rp-j iP~q 5size (cm) lb. Blackgrass, Stage I Wild Oat Stage IT Sugar Beet Oilseed Rape Kochia Mayweed, Scentless Annual Bluegrass Wild Buckwheat AlopecUrus myosuroilies Beta vulciari-s Brassica nap-us Kochia scovaria Matricaria inodora Poa nnua Polvcionum~ convolvulus 22.0 13.0 5 4 .0 Seven days following the first planting, a third pot was pr.epared with the following species.

Name Uointed Goatgrass Wild Oat Stage I Cheatgrass Winter Barley icv, Spring Ba~rley 1cv.

IN Annual Ryegrass Green Foxtail Winter Wheat 1cv.

Spring wheat Icv.

Downy Brome Genus.Species S i na~.~m Bromus. secalinuis Igri' Hordeum vulga-ca Klage Hordeum vlgar XoL ium multiflorum 12.0 15.0 a I0 18.0 24.0 ii .0 23.0 16.0 Centiurk' Era' Trlticum a iu B romuFL, tcr'.

IVY MORNINGLORY 95 90 60 35 0 JIMSONWEED 100 80 50 25 0 WO 89/00991 PCT/US88/02459 262 All postemergence plantings were grown in the greenhouse until herbicide application. Preemergence treaments were prepared immediately before herbicide application in the same manner as described for the postemergence treatments. Application of the herbicide was accomplished by first diluting the technical material in a nonphytotoxic solvent and applying over the surface of the plants and soil of all six components using a belt sprayer.

After treatment, all components were removed to the greenhouse where they were maintained for 21 days at temperatures of 19 0 C night and 30 C day with a 16-hour photoperiod and a relative humidity of 45 to percent. At this time, all species were rated using a visual scale of 0 representing no control and 100 representing complete control. Test results are summarized in Table G, REDROOT PIGWEED IVY MORNINGLORY J IMSONWEED WO 89/00991 PCT/US88/02459 TABLE G CMPD 1 RATE 0/HA

PREEMERGENCE

SPRING WHEAT WINTER WHEAT SPRING BARLEY WINTER BARLEY WILD OATS DOWNY B ROME CHEAT GRASS BLACKGRAS

S

ANN. BLUEGRASS ANNUAL RYEGRASS JOINT GOATGRASS GREEN FOXTAIL

RAPE

CTCHWD BEDSTRAW WILD BUCKWHEAT

KOCHIA

SNTLS MAYWEED BLACK NIGHTSHAD FIELD SPEEDWELL IVYLF SPEEDWELL

SUGARBEET

LAMBSQUARTER

FIELD PENNYCRES FIELD VIOLET 30 30 60 80 20 20 20 80 90 20 0 100 100 80 70 60 ~70 50 100 100 100 100 100 10 20 60 40 10 20 10 60 90 '10 0 50 100 70 70 60 90 60 so 90 100 90 100 90 8 0 0 0 0 0 0 100 100 m WO 89/ 00991 PGT/US88/02459 264 TABLE G CMPD 1 RATE G/HA 32 16 8 4 2

POSTEMERGENCE

SPRING WHEAT 20 0 0 0 WINTER WHEAT 10 0 0 0 0 SPRING BARLEY 10 0 0 0 0 WINTER BAR~LEY 30 20 10 10 0 WILD OATS 0 0 0 0 0 WILD OATS STG 2 0 0 0 0 0 DOWNY flROME 30 30 10 0 0 CHEAT GRASS 40 30 30 0 0 BLACKGRASS 50 40 20 20 0 BLACKGRASS STG2 40 40 30 30 0 ANN. BLUIEGRASS Q 0 0 Q 0 ANNUAL RYEcGRASS 10 0 00 0 JOINT GQATGRASS 0 0 0 0 0 GR~EEN FOXTAIL 0 0 0 00 RAPE 100 100 100 100 100 CTCHWD BEDSTRAW 90 60 40 20 0 WILD BUCK~WHEAT 70 60 40 40 KOCHIA 70 40 30 20 0 SNTLS MAYWEED 90 80 70 60 BLACK~ NIG1HTSHAD 60 50 50 40 3,Q FIELD SPEEDWELL 0 0 0 0 0 IVYLE SPEEDWELL 60 30 0 0 0 SUGARBEET 100 100 100 100 100 LAMESQUARTER 20 10 0 0 0 FIELD PENNYCRES 100 100 100 90 FIELD VIOLET 60 40 20 0 0 WO 89/0099 1 PL-T/US88/02459 TABLE G 265 CMPD RATE G/HA 64 32 16 8 4

PREEMERGENCE

SPRING WH-EAT 0 0 0 0 0 WINTER WHEAT 0 0 0 0 0 SPRTNG BARLEY 0 0 0 0 0 WINTER BARLEY 10 0 0 0 0 WILD OATS 0 0 0 0 0 DOWNY BROME 0 0 0 0 0 CHEAT GRASS 0 0 10 0 BLACKGRASS 30 10 0 0 0 ANN. BLUEGRASS 40 10 0 0 0 ANNUAL RYEGRASS 30 10 0 0 0 JOINT GOATGRASS 20 20 0 0 0 GREEN FOXTAIL 10 0 0 0 RAPE 80 8070 40 CTCHWD BEDSTRAW 70 60 40 0 0 WILD BUCK~WHEAT 90 70 50 30 0 KOCHIA 20 0 0 0 0 SNTLS MAYWEED 70 50 30 0 0 BLACK NIGHTSHAD 40 10 0 0 0 FIELD SFEEDWELL 30 30 0 0 0 IVYLF SPEEDWELL 100 80 70 40 SUGARBEFT 100 100 10Q 90 LAMBSQUARTVR 80 70 40 20 0 FIELD PENNYClRES 70 20 10 0 0 FIELD VIOLET 00 100 90 80 1.25 1.4 1.6 ZAXM.6lS 1 1dONW111fH1 DV2 1 j1.25 1.4 rr 72 i i! WO 89/00991 PCT/US88/02459 266 TABLE G CMPD RATE G/HA 64 32 16 8 4

POSTERERGENCE

SPRING WHEAT 0 0 0 0 0 WINTER WHEAT 0 0 0 0 0 SPRING BARLEY 0 0 0 0 0 WINTER BARLEY 0 0 0 0 0 WILD OATS 0 0 0 0 0 WILD OATS STG 2 10 0 0 0 0 DOWNY BROME 0 0 0 0 0 CHEAT GRASS 0 0 0 0 0 BLACKGRASS 0 0 0 0 0 BLACKGRASS STG2 30 20 0 0 0 ANN. BLUEGRASS 0 0 0 0 0 ANNUAL RYEGRASS 0 0 0 0 0 JOINT GOATGRASS 0 0 0 0 0 GREEN FOXTAIL 30 0 0 0 0 RAPE 100 100 100 90 CTCHWD BEDSTRAW 10 10 0 0 0 WILD BUCKWHEAT 80 80 60 40 KOCHIA 90 80 60 40 SNTLS MAYWEED 100 80 70 50 BLACK IIGHTSHAD 70 60 30 20 0 FIELD SPEEDWELL 20 0 0 0 0 IVYLF SPEEDWELL 0 0 0 0 SUGARBEET 100 100 100 70 LAMBSQUARTER 80 80 70 70 FIELD PENNYCRES 100 90 90 G0 FIELD VIOLET 30 20 0 0 0 WO 89/00991 PCT/US88/02459 TABLE G 267 CMPD 6 RATE 125 64 32 16

PREEMERGENCE

SPRING WHEAT 10 0 0 0 WINTER WHEAT 0 0 0 0 SPRING BARLEY 10 0 0 0 WINTER BARLEY 10 0 0 0 WILD OATS 20 0 0 0 DOWNY BROME 10 0 0 0 CHEAT GRASS 0 0 0 0 BLACKGRASS 40 10 10 0 ANN. BLUEGRASS 30 30 20 0 ANNUAL RYEGRASS 20 20 0 0 JOINT GOATGRASS 10 0 0 0 GREEN FOXTAIL 20 0 0 0 RAPE 100 100 100 CTCHWD BEDSTRAW 90 90 30 WILD BUCKWHEAT 100 100 90 KOCHIA 50 50 30 0 SNTLS MAYWEED 90 40 30 BLACK NIGHTSHAD 90 80 60 FIELD SPEEDWELL 40 30 20 0 IVYLF SPEEDWELL 100 100 60 SUGARBEET 100 100 100 100 LAMBSQUARTER 100 90 90 FIELD PENNYCRES 100 100 80 FIELD VIOLET 100 100 90 WO 89/00991 WO 8900991PCT/ US88/02459 TABLE G CMPD 6 RATE G/HA

POSTEMERGENCE

SPRING WHEAT WINTER WHEAT SPRING BARLEY WINTER BARLEY WILD OATS WILD OATS STG 2 DOWNY BROME CHEAT

GRASS

BLACKGRASS

BLACKGRASS STG2 ANN. BLUEGRAS ANNUAL RYEGRASS JOINT GOATGRASS GREEN FOXTAIL

RAPE

CTCHWD BEDSTRAW WILD BUCKWHEAT

KOCHIA

SNTLS MAYWEED BLACK NIGHTSHAD FIELD SPEEDWELL IVYLF SPEEDWELL

SUGARBEET

LP :BSQUARTER Flt LD PENNYCR2S FIELD VIOLET 125 0 0 0 0 0 0 10 0 0 0 0 0 0 20 100 80 100 70 100 80 110 70 100 100 100 90 64 .0 0 0 0 0 0 0 0 0 0 0 0 0 20 100 70 100 0 100 70 0 60 100 100 80 60 32 0 0 0 0 0 0 0 0 0 0 0 0 0 0 100 30 90 40 80 60 0 40 100 70 70 20 J 0 0 0 0 0 0 0 0 0 0 0 0 0 100 0 0 0 100 0 WO 89/00991 PCT/US88/02459 TABLE G CMPD 31 WO 89/00991 WO 8900991PCT/US88/ 02459 TABLE G CMPD 8 RATE G/HA

PREEMERGENCE

SPRING WHEAT WINTER WHEAT SPRING BARLEY WINTER BARLEY WILD OATS DOWNY BROME CHEAT GRASS ANN. BLUEGRASS ANNUAL RYEGRASS JOINT GOATGRASS G3REEN FOXTAIL

RAPE

CTCHWD BEDSTRAW WILD BUCKWHEAT

KOCHIA

SNTLS MAYWEED BLACK NIGHTSHAD FIELD SPEEDWELL IVYLF SPEEDWELL

SUGARBEET

LAMB SQUARTER

PENNYCRES

FIELD VIOLET 64 32 16 0 0 0 0 0 100 WO 89/00991 WO 89/00991P CT/U S88/0245 9 TABL~E i; cml8 RATE G/HA 125

POSTEMERGENCE

SPRING WHEAT WINTER WHEAT SPRING BARLEY WINTER BARLEY WILD OATS WILD OATS STG 2 DOWNY BROME CHEAT GRASS 50 BLACKGRASS 70 BLACKGRASS STG2 80 ANN. BLUEGRASS 20 ANNUAL RYEGRASS 20 JOINT GOATGRASS 40 GREEN FOXTAIL 70 RAPE 100 CTCHWD BEDSTRAW 90 WILD BUCKWHEAT 70 XOCHIA 10 SNTLS MAYWEED 100 BLACK NIGHTSHAD 60 FIELD SPEEDWELL 20 IVYLF SPEEDWELL 60 SUGARBEET 100 LANBSQUARTER 70 FIELD PENNYCRES 100 FIELD VIOLET 30 64 32 16 50 30 20 50 40 20 60 5vj 20 10 10 0 0 0 0 20 20 10 so 30 20 00 100 100 60 50 30 40 40 30 30 30 10 .00 100 90 40 30 30 0 0 0 10 0 0 '00 90 90 40 40 20 .00 100 100 0 0 0 0 0 0 0 0 100 0 0 0 0 100 0 1 WO 89/00991 PCT/US88/02459 TABLE G CMPD 9 RATE G/HA

PREEMERGENCE

SPRING WHEAT WINTER WHEAT SPRING BARLEY WINTER BARLEY WILD OATS DOWNY BROME CHEAT GRASS

BLACKGRASS

ANN. BLUEGRASS ANNUAL RYEGRASS JOINT GOATGRASS GREEN FOXTAIL

RAPE

CTCHWD BEDSTRAW WILD BUCKWHEAT

KOCHIA

SNTLS MAYWEED BLACK NIGHTSHAD FIELD SPEEDWELL IVYLF SPEEDWELL

SUGARBEET

LAMBSQUARTER

FIELD PENNYCRES LD VIOLET FIELD VIOLET 64 32 16 90 90 80 60 WO 89/00991 PCT/US88/02459 TABLE G CMPD 9 RATE GINA

POSTEMERGENCE

SPRING WHEAT WINTER WHEAT SPRING BARLEY WINTER BARLEY WILD OATS WILD OATS STG 2 DOWNY BROME

GRASS

BLACKGRASS

BLACKGRASS STG2 ANN. BLUEGRASS ANNUAL RYEGRASS JOINT GOATGRASS GREEN FOXTAIL

RAPE

CTCHWD BEDSTRAW WILD BUJCKWHEAT

KOCHIA

SNTLS MAYWEED BLA.ICK NIGHTSHAD FIELD SPEEDWELL IVYLF SPEEDWELL

LAMESQUARTER

FIELD PENNYCRES FIELD VIOLET 64 32 16 2 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0.

G

0 0 100 0 30 10 0 100 0 0 0 70 10 0 0 40 0 100 0 WO 89/00991 WO 8900991PCT,/US88/02459 TABLE G CMPD 11 RATE G/HA

PREEMERGENCE

SPRING WHEAT WINTER WHEAT SPRING BARLEY WINTER BARLEY WILD OATS DOWNY BROI4E CHEAT GRASS

BLACKGRASS

ANN. BLUEGRASS ANNUAL RYEGRASS JOINT GOATGRASS GREEN FOXTAIL

RAPE

CTCHWD BEDSTRAW WILD BUCKWHEAT

KOCHIA

SNTLS MAYWEED BLACK NIGHTSHAD FIELD SPEEDWELL IVYLF SPEEDWELL

SUGARBEET

LAMB SQUAflTER

PENNYCRES

FIELD VIOLET 64 32 16 WO 89/00991 WO 8900991PCT/US88/02459

I

TABLE G rMPD J11 RATE G/HA

POSTEMERGENCE

GRASS

BLACKGRASS

BLACKGRASS STG2 ANN. BLUElGRASS ANNUAL fYEGRASS JOINT GOATGRASS GREEN FOXTAIL

RAPE

CTCIIWD Bi8DSTRAW WILD BUCKWHEAT

KOCHIA

SNTLS M4AYWEED BLACK NIGHTSHAD FIELD SPEEDWELL IVYLF SPEEDWELL

LAMBSQUARTER

FIELD PENNYCRES FIELD VIOLET 64 32 16 WO 89/00991 WO 8900991PCT/US88/02459 TABLE G CMPD 12 RATE G/HA PFREEMERGEN(rE SPRING WHEAT WINTER WHEAT SPRING BARLEY WINTER LARLEY WILD OATS DOWNY BROME CHEAT GRASS

BLACKGRASS

ANN. BLUEGRASS ANNUAL RYEGRASS JOINT GOATGRASS GREEN FOXTAIL ALTEX RAPE CTC*{WD BEDSTRAW WILD BUCKWHEAT

KOCHIA

SNTLS MAYWEED BLACK NIGHTSHAD FIELD SPEEDWELL TVYLF SPEEDWELL

SUGARBEET

LAMBS QUARTrER FIELD FIENNYCRES FIELD VIOLET 64 32 16 0 o 0 0 0 o 0 0 o 0 0 o 0 0 .0 0 0 0 0 0 0 0 0 0 0 :Q 0 0 0 0 0 0 '0 100 0 0 0 WO 89/00991 WO 8900991PCT/US88/02459 TABLE G CmpD 12 RATE G/HA

POSTEMERGENCE

SPRING WHEAT WINTER WHEAT SPRING BARLEY WINTER BARLEY WILD OATS WILD OATS STG 2 DOWVNY BROME

GRASS

BLACKGRASS

BLACIKGRASS STG2 ANN. BLUEGRASS ANNUAL RYEGRASS JOINT GOATGRASS GREEN FOXTAIL ALTEX RAPE CTCHWD BEDSTRAW WILD BUCKWHEAT

KOCHIA

SNTLS MAYWEED BLACK~ NIGHTSHAD FIELD SPEEDWELL IVYLF SPEEDWELL S0ISUGARBEET

LAMBSQUARTER

FIELD PENNYCRES FIELD VIOL2T 64 32 16 0 0 0 0 0 0 0 0 0 0 20 20 0 0 0 00 100 100 100 80 80 50 50 90 90 80 80 7n 60 40 20 70 60 40 20 0 70 50 40 20 50 20 20 10 0 v 0' 60 30 100 100 100 50 40 10 S- WO 89/00991 WO 89/0091P CT/US 88/0 2459 277 TABLE G CMPD 13 RATE G/HA P RE EME RGEN CE SPRING WHEAT WINTER WHlEAT SPRING BARLEY WINTER BARLEY WILD OATS DOWNY BROME CHEAT GRASS KG RAS S ANN. BLUEGRASS ANNUAL RYEGRASS JOINT GOATGRASS GREEN FOXTAIL ALTEX RAPE CTCHWD BEDSTRAW WILD BUCrWHEAT JlOCHIA SNTLS MAYWEED BLACK NIGHTSHIAD FIELD SPEEDWELL IVYLF SPEEDWELL

SUGARBEET

LAM B SQU ARTE R

PENNYCRES

FIELD VIOLET 64 32 16 0 0 10 0 10 0 0 0 20 10 10 10 100 60 90 40 90 70 40 60 10 0 90 90 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 s0 0 o Q 0 0 0 0 0 7 0 0 0 WO 89/00991 WO 8900991PCT/L1S88/02459 TABLE G CMPD 13 RATE G/HA

POSTEMERGENCE

SPRING WHEAT WINTER WHEAT SPRING BARLEY WINTER BARLEY WILD OATS WILD OATS STG 2 DOWNY BROME CHEAT GRASS

BLACKGRASS

BLACI(GRASS STG2 ANN. BLUEGRASS ANNUAL RYEGRASS JOINT GOATGRASS GREEN FOXTAIL

RAPE

CTCHWD BEDSTRAW WILD BUCKWHEAT

KOCHIA

SNTLS MAYWEED BL.ACK~ NIGHTSHAD FIELD SPEEDWELL IVYLF SPEEDWELL StJGARBEET

LANESQUARTER

FIELD PENNYCRES FIELD VIOLET 125 0 0 0 0 0 0 0 0 0 0 0 0 20 20 100 90 70 80 100 80 20 0 100 90 100 10 64 32 16 8 4 0 0 0 0 0 0 0 0 0 0 0 0 0 0 100 60 40 20 70 50 0 0 100 90 100 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 100 0 0 0 100 0

J.

WO 89/00991 PCT/US88/02459 TABLE G CMPD 29 RATE GINA

PREEMERGENCE

BLACKGRASS

ANN. BLUEGRASS ANNUAL RYEGRASS JOINT GOATGRASS GREEN FOXTAIL

RAPE

CTCHWD BEDSTRAW WILD BUCKWHEAT

KOCHIA

SNTLS MM(WEED BLACK NIGHTSHAD FIELD SPEEDWELL IVYtLF SPEEDWELL

SUGARBEET

LAM'BSQUARTER

PENNYCRES

20 FIELD VIOLET 125 100 100 100 100 100 0 0 100 64 32 16 WO 89/00991, PCT/US88/02459 TABLE G CMPD 62 WO 89/ 00991 PCT/US88/02459 TABLE G CMPD 29 RATE G/HA

POSTEMERGENCE

SPRINq WHEAT WINTER WHEAT SPRING BARLEY WINTER BARLEY WILD OATS WILD OATS STG 2 DOWNY BROME CHEAT

GRASS

BLACKGRASS

flLACKGRASS STG2 ANN. BLUEGRASS ANNUAL RYEGRASS JOINT GOATGRASS GREEN FOXTAIL

RAPE

CTCHWV BEDSTRAW WILD 3UCKW~HEAT iNOCRTA SNTLS ?4AYWEED BLACK NIGHTSHAD FIELD SPEEDWELL IVYLF SPEEDWELL

SUGARBEET

LANBSQUARTER

FIELD PENNYCRES FIELD VIOLET 125 0 0 0 40 0 50 70 30 0 20 50 100 70 100 100 100 70 50 60 100 80 100 90 64 32 16 0 0 0 0 0 0 0 0 0 20 10 0 40 30 0 0 0 0 0 0 0 0 0 40 30 2 100 100 100 50 30 101 80 60 so 90 90 100 90 40 30 30 20 0 50 30 100 100 100 70 60 80 70 70 50 3 11 wo 89/0099 A WO 8900991PCT/US88/02459 TABLE G CJAdPD 31 RATE G/HA

PREEMERGENCE

BLACKGR".F

ANN. BLUCt:.-ASS ANNUAL RYEGRASS JOINT GOATGRASS GREEN FOXTAIL

RAPE

CTCHWD BEDSTRAW WILD BUCKWHEAT

NOCHIA

SNTLS MAYWEED BLACK NIGKTSHAD FIELD SPEEDWELL IVYLF SPEEDWELL SUGARBE2T LAM B SQU ARTE R

PENNYCRES

P'±ElJD VIOLET 64 32 16 40 20 0 50 40 70 60 50 40 30 20 80 80 80 00 WO 89/00991 WO 8900991PCT/US88/02459 282 TABLE G CMPD 31 RATE G/HA

POSTEMERGENCE

BLACKGRASS

BLACKGRASS STG2 ANN. BLUEGRASS ANNUAL RYEGRASS JOINT GOATGRASS GREEN FOXTAIL

RAPE

CTCHWD BEDSTRAW WILD BUCKWHEAT

KOCHIA

SNTLS MAYWEED BLACK NIGHTSHAD FIELD SPEEDWELL IVYLF SPEEDWELL SUGARS

SET

LAMBSQUARIEt% FIELD PENN'YC?,ES FIELD VIOLET 64 32 16 0 100 100 4 0 100 0 100 0

-A

WO 89/00991 PCT/US88/02459 TABLE G CMPD RA.TE G/HA PR EEM ER GEN CE SPRING WHEAT WINTER WHEAT SPaRING BARlLEY WINTER BARLEY WILD OATS DOWNY BROME CHEAT GRASS

BLACKGRASS

ANN. BLUEGRASS ANNUAL RYEGflASS JOINT GOATGRASS GREEN FOXTAIL

RAPE

CTCHWD BEDSTRAW WILD BUCKWH~EAT

KOCHIA

SNTLS MAYWEED BLACK' NIGHTSHAD FIELD SPEEDWELL IVYLF SP'EEDWELL

OEIGARSEET

LAN3SQUARTER

PENNYCRES

FIELD VIOLET 125 10 0 30 40 20 20 40 80 60 40 30 50 100 80 100 80 100 70 100 100 100 100 100 100 64 321.

0 0 0 10 0 0 20 20 50 20 0 10 100 70 70 40 70 40 90 100 100 80 90 70 8 0 0 0 0 0 0 0 0 0 0 100 100 100 so' ~I i' rr Irrrsl i~Warr~l rrrrrr~lrr~l l~ WO 89/00991 PCT/US88/02459 TABLE G CMPD RATE G/HA

POSTEMERGENCE

BLACKASS

BLACKGRASS STG2 BLACKGRASS STG2 ANN. BLUEGRASS ANNUAL RYEGRASS JOINT GOATGRASS GREEN FOXTAIL

RAPE

CTCHWD BEDSTRAW WILD BUCKWHEAT

KOCHIA

SNTLS MAYWEED BLACK NIGHTSHAD FIELD SPEEDWELL IVYLF SPEEDWELL

SUGARBEET

LAMBSQUARTER

FIELD PENNYCRES FIELD VIOLET 64 32 16 a 1. t y WO 89/00991 PCT/US88/02459 TABLE G CMPD 36 RATE G/HA

PREEMERGENCE,

BLACKGRASS

ANN. BLUEGRASS ANNUAL RYEGRASS JOINT GOATGRASS GREEN FOXTAIL

RAPE

CTCHWD BEDSTRAW WILD BUCK~WHEAT

KOCHIA

SNTLS MAYWEED BLACK NIGHTSHAD FIELD SPEEDWELL IVYLF SPEEDWELL

SUGARBEET

LAMBSQUARTER

PENNYCRES

FIELD VIOLET 64 32 16 0 0 0 0 100 100 100 100 100 100 rr~ lipi.

L~.

WO 8 )/00991 PCT/US88/02459 TABLE G CMPD 36 RATE G/HA POSTEM' RGENCE SPRING WHEAT WINTER WHEAT SPRING BARLEY WINTER BARLEY WILD OATS WILD OATS STG 2 DOWNY BROME CHEAT GRASS

BLACKGRASS

BLACKGRASS STG2 ANN. BLUEGRASS ANNUAL RYEGRASS JOINT GOATGRASS GREEN FOXTAIL

RAPE

CTCHWD BEDSTRAW WILD BUCKWHEAT

KOCHIL

SNTLS MAYWEED BLACK NIGHTSHAD FIELD SPEEDWELL IVYLF SPEEDWELL FIELD PENNYCRES FIELD VIOLET 64 32 16 0 0 r, 0 0 100 100 100 0 0 100 100 L~ U WO 89/00991 PCT/US88/02459 TABLE G CMPD RATE G/HA

PREEMERGENCE

BLACKGRASS

ANN. BLUEGRASS ANNUAL RYEGRASS JOINT GOATGRASS GREEN FOXTAIL

RAPE

CTCHWD BEDSTRAW WILD BUCKWHEAT

KOCHIA

SNTLS MAYWEED BLACK NIGHTSflAD FIELD SPEEDWELL IVYLF SPEEDWELL

SUGARBEET

L AM BSQU ARTER

PENNYCRES

FIELD VIOLET 125 0 0 30 30 30 40 60 60 60 10 60 100 80 100 90 100 70 80 100 100 90 100 100 64 32 16 0 0 0 0 100 100 WO 89/00991 PCTIUS88/02459 TABLE G CMPD RATE GINHA

POSTEMERGENCE

GRASS

BLACKGRASS

BLACKGRASS STG2 ANN. BLUEGRASS ANNUAL RYEGRASS JOINT GOATGRASS GREEN FOXTAIL

RAPE

CTCHWD BEDSTRAW WILD BUCKWHEAT

IKOCHIA

SN'TLS MAYWEED BLACK~ NIGHTSHAD RUSSIAN THISTLE FIELD SPEEDWELL IVYLF

SPEEDWELL

SUGARDEET

LAMBSCf"ARTER FIELD PENNYCRES FIELD VIOLET 64 32 16 0 0 0 0 0 0 0 0 60 70 20 0 0 10 100 60 90 100 100 70 1.00 100 100 100 100 90 100 4 0 0 0 0 0 0 0 0 0 0 0 0 0 0 100 100 4 r, 0 100 100 60 90 80 100 50 2.00 100 100 100 80 80 90 -i .I I -I IL- I ~I i 1; i I ulc; WO 89/00991 PCT/US88/02459 289 TABLE G CMPD 56 RATE G/HA

PREEMERGENCE

SBLACKGRASS

ANN. BLUEGRASS ANNUAL RYEGRASS JOINT GOATGRASS GREEN FOXTAIL

RAPE

CTCHWD BEDSTRAW WILD BUCKWHEAT

KOCHIA

SNTLS MAYWEED BLACK NIGHTSHAD RUSSIAN THISTLE FIELD SPEEDWELL IVYLF SPEEDWELL

SUGARBEET

LAMBSQUARTER

FIELD PENNYCRES FIELD VIOLET 125 60 50 20 40 20 80 80 60 70 20 10 60 100 60 80 60 80 100 100 70 70 100 90 90 20 64 32 40 30 10 Ib 20 20 70 80 60 60 0 0 50 100 50 80 30 70 100 100 40 60 90 70 90 0 0 0 0 0 0 100 loo 100 0 I i WO 89/00991 PCT/US88/02459 290 TABLE

G

CMPD 56 RATE G/HA 125 64 32

POSTEMERGENCE

SPRING WHEAT 30 10 WINTER WHEAT 30 10 SPRING BARLEY 10 10 WINTER BARLEY 20 i0 WILD OATS 30 10 WILD OATS STG 2 40 10 DOWNY BROME 60 60 CHEAT GRASS 90 70 BLACKGRASS 90 70 BLACKGRASS STG2 90 60 ANN. BLUEGRASS 50 0 ANNUAL RYEGRASS 20 0 0 JOINT GOATGRASS 70 30 GRE4N FOXTAIL 20 0 0 RAKE 100 100 100 CTCHWD BEDSTRAW 80 40 WILD BUCKWHEAT 60 40 KOCHIA 90 40 SNTLS MAYWEED 90 90 BLACK NIGHTSHAD 0 0 0 RUSSIAN THISTLE 100 100 100 FIELD SPEEDWELL 50 40 IVYLF SPEEDWELL 60 30 SUGARBEET 100 100 100 LAMBSQUARTER 60 50 FIELD PENNYCRES 100 100 FIELD VIOLET r 0 0 WO 39/00991 PCT/US88/02459 TABLE G 291 CMPD 61 RATE G/HA 32 16 8 4 2

PREEMERGENCE

SPRING WHEAT 20 10 0 0 0 WINTER WHEAT 40 30 10 0 0 SPRING BARLEY 40 30 10 0 0 WINTER BARLEY 20 10 0 0 0 WILD OATS 0 0 0 0 0 DOWNY BROME 30 10 0 0 0 CHEAT GRASS 80 60 60 40 BLACKGRASS 20 20 20 10 0 ANN, BLUEGRASS 30 20 20 10 0 ANNUAL RYEGRASS 30 30 20 0 0 JOINT GOATGRASS 30 30 10 0 0 GREEN FOXTAIL 70 40 20 0 0 RAPE 100 100 100 100 CTCHWD BEDSTRAW 100 80 60 50 WILD BUCKWHEAT 80 80 70 60 KOCHIA 70 50 30 0 0 SNTLS MAYWEED 100 100 100 90 BLACK NICHTSHAD 70 60 50 50 RUSSIAN THISTLE 60 30 20 0 0 FIELD SPEEDWELL 70 60 50 50 IVYLF SPEEDWELL 70 50 30 0 0 SUGARBEET 100 90 90 90 LAMBSQUARTER 90 90 80 80 FIELD PENNYCRES 100 90 80 70 FIELD VIOLET 80 60 60 50 i i WO 89/00991 8900991PCT/US88/02459 292 TABLE G CMPD 61 RATE G/HA 32 16 8 4 2

POSTEMERGENCE

SPRING WHEAT 0 0 0 0 0 WINTER WHEAT 10 10 0 0 0 SPRING BARLEY 0 0 0 0 0 WINTER BARLEY 20 20 10 0 0 WILD OATS 0 0 0 0 0 WILD OATS STG 2 0 0 0 0 0 DOWNY BROME 10 0 0 0 0 CHEAT GRASS 30 10 0 0 0 BLACKGRASS 0 0 0 0 0 BLACKGRASS STG2 30 30 0 0 0 ANN. BLUEGRASS 0 0 0 0 0 ANNUAL RYE.GRASS 0 0 0 0 0 JOINT GOATGRASS %0 0 0 0 0 GREEN FOXTAIL 20 2i 10 0 Q RAPE 100 100 100 100 CT.CHWD BEDSTRAW 80 80 50 10 0 WILD BUCKWHEAT 60 60 30 0 0 KOCHIA 70 60 60 50 SNTLS MAYWEED 100 100 100 100 BLACK NIGH-TSHAD 30 10 0 0 0 FIELD SPEEDWELL 30 30 30 0 0 IVYLF SPEEDWELL 30 30 20 0 0 SUGARBEET 100 100 100 100 LAMBSQUARTER 20 10 0 0 0 FIELD Pl1,NNYCRES 100 100 100 100 100 FIELD VIOLET 20 20 10 0 0 WO 89/00991 PCT/US88/02459 '63 TABLE G CMPD 62 RATE G/HA 8 4 2 1

PREEMERGENCE

SPRING WHEAT 10 0 0 0 WINTER WHEAT 20 1Q 0 0 SPRING BARLEY 40 40 30 0 WINTER BARLEY 10 0 0 0 WILD OATS 0 0 0 0 DOWNY BROME 0 0 0 0 CHEAT GRASS 30 10 0 0 BLACKGRASS 10 10 0 0 ANN. BLUEGRASS 30 10 0 0 ANNUAL RYEGRASS 30 10 0 0 JOINT GOATGRASS 20 10 0 0 GREEN F'QXTAlL 40 10 0 0 RAPE 100 100 100 CTCH-WD BEDSTRAW 20 20 0 0 WILD BUCKWHEAT 70 70 60 KOCHIA 60 20 10 0 SNTLS MAYWEED 100 90 80 BLACK NIGHTSHAD 70 40 30 RUSSIAN THI8TLE 80 80 50 FIELD SPEEDWELIL 70 60 30 IVYLF SPEEDWELL 70 30 10 0 SUGARBEET 100 100 70 IAMESQUARTER 90 90 80 FIELD PENNYCRES 100 90 60 FIELD VIOLET 50 40 20 2 WO 89/00991 FCT/US88/02459 294 TABLE

G

CMPD 62 RATE G/HA 8 4 2 1

POSTEMERGENCE

SPRING WHEAT 40 30 10 0 WINTER WHEAT 30 10 0 0 SPRING BARLEY 40 20 0 0 WINTER BARLEY 30 10 0 0 WILD OATS 0 0 0 0 WILD OATS STG 2 20 10 0 0 DOWNY BROME 0 0 0 0 S CHEAT GRASS 50 40 0 0 BLACKGRASS 0 0 0 0 BLACKGRASS STG2 40 10 0 0 ANN, BLUEGRASS 30 20 0 0 ANNUAL RYEGRASS 10 0 0 0 JOINT GOATGRASS 20 20 0 0 GREEN FOXTAIL 20 20 0 0 RAPE 100 100 100 CTCHWD BEDSTRAW 50 30 0 0 WILD BUCKWHEAT 60 30 20 0 KOCHIA 70 40 40 SNTLS MAYWEED 80 80 60 BLACK NIGHTSHAD 60 20 10 0 FIELD SPEEDWELL 20 0 0 0 IVYLF SPEEDWELL 30 10 0 0 SUGARBEET 100 100 90 LAMBSQUARTER 20 10 0 0 FIELD PENNYCRES 100 100 90 FIELD VIOLET 60 10 0 0 I i 89f002991 PCT/US88/02459 TABLE G CMPD 64 RATE G/HA

PREEMZRGENCE

125 64 32 16 8 4 2 1 SPRING WHEAT 50 30 10 WINTER WHEAT 40 20 20 SPRING BARLEY 60 60 50 WINTER BARLEY 70 60 60 WILD OATS 30 20 10 DOWNY BROME 30 10 10 CHEAT GRASS 80 60 50 BLACKGRASS 50 30 10 ANN. BLUEGRASS 70 60 30 ANNUAL RYEGRASS 70 40 40 JOINT GOATGRASS 40 30 30 GPEEN FOXTAIL 100 80 60 RAPE 100 100 100 CTCHWD BEDSTRAW 100 100 100 WILD BUCKWHEAT 100 90 90 KOCHIA 90 80 80 SNTLS MAYWEED 100 100 90 BLACK NIGHTSHAD 80 80 70 RUSSIAN THISTLE 100 90 80 FIELD SPEEDWELL 100 90 80 IVYLF SPEEDWELL 100 90 90 0 0 0 10 0 0 20 0 0 50 30 0 0 0 0 0 0 0 30 10 0 0 0 0 30 1.0 0 30 10 10 0 0 0 40 30 0 100 100 100 90 70 60 80 70 70 70 70 60 90 90 80 60 60 50 50 50 20 70 70 60 80 60 60 0 0 0 0 0 0 0 0 0 0 0 0 100 0 SUGARBEET 100 100 100 100 100 LAMBSQUARTER 100 100 100 80 80 FIEI,D PENNYCRES 100 100 100 90 80 FIELD VIOLET 90 80 70 70 60 r i -ir _r i I; I I wo 89/00991 PCT/US88/02459 TABLE G CMPD 64 RATE G/HA

POSTEMERGENCE

125 64 32 16 8 4 2 1 SPRING WHEAT 0 0 0 0 0 WINTER WHEAT 20 10 0 0 0 SPRING BARLEY 10 10 b 0 0 WINTER BARLEY 0 0 0 0 0 WILD OATS 0 0 0 0 0 WILD OATS STG 2 0 0 0 0 0 DOWNY BROME 10 0 0 0 0 CHEAT GRASS 30 20 0 0 0 BLACKGRASS 20 10 0 0 0 BLACKGRASS STG2 20 0 0 0 0 ANN. BLUEGRASS STG2 20 0 0 0 0 ANN. BLUAL RYEGRASS 0 0 0 0 0 ANNUAL RYEGRASS 0 0 0 0 0 JOINT GOATGRASS 40 10 0 0 0 GREEN FOXTAIL 30 30 10 0 0 RAPE 100 100 100 100 90 CTCHWD BEDSTRAW 100 100 70 70 50 WILD BUCKWHEAT 100 100 70 60 40 KOCHIA 80 80 60 60 50 SNTLS MAYWEED 100 100 100 70 50 BLACK NIGHTSHAD 40 30 20 20 10 FIELD SPEEDWELL 20 20 0 0 0 IVYLF SPEEDWELL 100 80 40 20 0 SUGARBEET 100 100 100 100 100 LAMBSQUARTER 70 40 20 20 0 FIELD PENNYCRES 100 100 100 100 100 FIELD VIOLET 30 10 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 90 20 40 40 30 0 0 0 100 0 100 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 100 0 I WO 89/00991 PCT/US88/02459 TABLE G CMPD RATE G/HA 125 64 32 16

PREEMERGENCE

SPRING WHEAT 10 0 0 0 WINTER WHEAT 20 10 0 0 SPRING BARLEY 70 50 30 20 WINTER BARLEY 70 60 30 30 WILD OATS 20 20 10 0 DOWNY BROME 50 20 10 0 CHEAT GRASS 60 40 30 0 S BLACKGRASS 90 90 80 80 ANN. BLUEGRASS 60 60 50 40 ANNUAL RYEGRASS 60 50 50 40 JOINT GOATGRASS 50 40 30 30 GREEN FOXTAIL 90 80 80 40 RAFE 100 100 100 90 CTCHWD BEDSTRAW 100 100 90 80 WILD BUCKWHEAT 100 90 90 90 KOCHIA 90 80 80 60 SNTLS MAYWEED 100 100 100 90 BLACK NIGHTSHAD 80 80 70 70 RUSSIAN THISTLE 90 90 90 70 FIELD SPEEDWELL 100 90 80 80 IVYLF SPEEDWELL 100 90 90 70 SUGARBEET 100 100 100 100 2 LAMBSQUARTER 100 100 90 90 FIELD PENNYCRES 100 100 100 90 FIELD VIOLET 100 100 100 100 8 4 2 1 0 0 0 0 0 0 0 40 40 40 20 30 90 80 80 60 90 60 70 80 70 100 80 90 100 4o lOO 0 0 0 0 0 0 0 40 20 20 10 10 80 60 70 40 70 50 60 70 50 100 60 9 1 90 90 0 0 0 0 0 0 0 0 0 0 0 0 230 PCT/US88/02459 WO 89/00991 298 TABLE G CMPD RATE G/HA 125 64

POSTEMERGENCE

SPRING WHEAT 0 0 WINTER WHEAT 0 0 SPRING BARLEY 10 10 WINTER BARLEY 20 10 WILD OATS 0 0 WILD OATS STG 2 0 0 DOWNY BROME 0 0 CHEAT GRASS 20 10 BLACKGRASS 40 20 BLACKGRASS STG2 80 60 ANN. BLUEGRASS 40 30 ANNUAL RYEGRASS 20 20 JOINT GOATGRASS 0 0 GREEN FOXTAIL 40 30 RAPE 100 100 CTCHWD BEDSTRAW 90 90 WILD BUCKWHEAT 90 80 KOCHIA 100 100 SNTLS MAYWEED 100 100 BLACK NIGHTSHAD 80 40 FIELD SPEEDWELL 80 60 IVYLF SPEEDWELL 80 50 SUGARBEET 100 100 LAMBSQUARTER 50 30 FIELD PENNYCRES 100 100 FIELD VIOLET 80 50 32 16 8 4 2 1 0 0 0 0 0 0 0 0 0 60 10 20 0 0 100 80 80 90 100 40 50 50 100 20 100 50 o0 0 0 0 0 0 0 0 0 0 50 0 0 0 0 100 80 70 70 100 40 30 30 100 10 100 40 o 0 0 0 0 0 0 0 0 0 10 0 0 0 0 100 30 30 60 90 10 10 0 100 0 100 20 o 0 0 0 0 0 0 0 0 0 0 0 0 0 0 100 0 0 0 0 100 0 o o0 o0 wo 89/00991 PCT/US88/02459 TABLE G CMPD 66 RATE G/HA 125 64 32

PREEMERGENCE

SPRING WHEAT 10 10 0 WINTER WHEAT 0 0 0 SPRING BARLEY 30 0 0 WINTER BARLEY 30 20 20 WILD OATS 20 20 10 DOWNY BROME 40 10 0 CHEAT GRASS 20 10 0 S BLACKGRASS 50 40 30 ANN. BLUEGRASS 40 40 30 ANNUAL RYEGRASS 30 20 20 JOINT GOATGRASS 10 10 0 GREEN FOXTAIL 60 50 30 RAPE 100 100 100 CTCHWD BEDSTRAW 90 90 90 WILD BUCKWHEAT 90 90 90 KOCHIA 50 50 20 SNTLS MAYWEED 90 90 90 BLACK NIGHTSHAD 70 50 40 RUSSIAN THISTLE 10 0 0 FIELD SPEEDWELL 60 60 50 IVYLF SPEEDWELL 90 70 70 SUGARBEET 100 100 100 LAMBSQUARTER 100 90 90 FIELD PENNYCRES 80 80 80 FIELD VIOLET 100 100 90 16 8 4 2 0 0 0 0 0 0 10 10 0 0 0 0 30 30 10 0 0 20 100 90 80 10 80 30 0 0 50 70 90 40 70 90 d..i I i WO 89/00991 PCT/US88/02459 300 TABLE G CMPD 66 RATE G/HA 125

POSTEMERGENCE

SPRING WHEAT 10 WINTER WHEAT 0 SPRING BARLEY 30 WINTER BARLEY 10 WILD OATS 0 WILD OATS STG 2 10 DOWNY BROME 0 S CHEAT GRASS 10 BLACKGRASS 30 BLACKGRASS STG2 20 ANN. BLUEGRASS 10 ANNUAL RYEGRASS 10 JOINT GOATGRASS 20 GREEN FOXTAIL 40 RAPE 100 CTCHWD BEDSTRAW 100 WILD BUCKWHEAT 90 KOCHIA 60 SNTLS MAYWEED 90 BLACK NIGHTSHAD 80 RUSSIAN THISTLE 50 FIELD SPEEDWELL 0 S IVYLF SPEEDWELL 70 SUGARBEET 100 LAMBSQUARTER 60 FIELD PENNYCRES 90 FIELD VIOLET 80 64 32 16 8 4 2 0 0 20 10 0 10 0 10 30 20 10 10 20 30 100 100 80 60 90 50 50 0 60 100 40 90 40 0 0 S0 0 10 10 0 0 0 0 0 0 0 0 0 10 10 0 10 0 0 10 0 10 0 .100 100 80 40 80 50 50 0 0 60 100 100 40 0 90 0 0

Claims

1. A compound having the formula w 11 JS0 2 NHCNA and herbicidally suitable salts thereof; wherein *440 WO 89/00991 PCT,'US88/O2459 What is claimed is: BA-B-77-A 1. A compound having I'th& formula -S 2 NHCNA J is selected f rom J-Z d~a Qi a -4 WO 89/0099 1 1'CT/US88/02459 302 54 3Q2 54 3 E- 5 43 6 2E- 2 R 1 A Q~N and Q 2 R 2 E is a single bond or -H- is -C(Tl)-N-O-Alk;, T' is selected from CN, F, Cl, Br, SCN, N 3 1 Cl tro C2 alkoxy, C1 to C 2 thioalkyl, NH(C 1 to C 2 alkyl), N(C 1 to C 2 alkyl) 2 N(OCHI)CI 3 and N(CH 2 3 or 4; WO 89/00991 PCT/US88/02459 303 Alk is selected from C1 to C 3 alkyl, optionally substituted with Cr4, OCH 3 SCH 3 or halogen; and CH 2 CH-CH 2 Q 2 is -C(T 2 )-N--O-Alk; T 2 is selected from H; C 1 to C 3 alkyl optionally substituted with CN, OCH 3 SCH 3 or halogen; cyclopropyl; F; Cl; Br; Cr4; SCN; N 3 C 1 to C 2 alkoxy; C 1 to C 2 thioalkyl; Nl-(C 1 to C2 alkyl); N(Cl to C 2 alkyl) 2 N(OCH 3 )CH 3 and r~ 2 3 o Rl is selected from H, CI, to C 3 alkyl, Cl to C 3 haloalkyl, halogen, Cr4, nitro, C 1 to C 3 alkoxy, C1 to C23 haloalkloxy, CI to C23 alkylthio, C1 to C23 alkylsulfinyl, C 1 to (23 alkylsulfonyl, SCF 2 Ht NH 2 NHCH 3 N(CH 3 2 Or C 1 to C2 alkyl substituted with one C1 to C 2 alkoxy, C 1 to C2 haloalkoxy, SH, SCH 3 Cr4 or OH; R 2 is selected from H, F, Cli Br, C1 to C alkyli C, to C 2 haloalkyl or C 1 to C 2 alkoxy; R 3 is selected from Hi, C1 to C 3 alkyl, C1 to C haloalkyl, C 3 to C24 alkenyl, (23 to C 4 alkynyl, CH 2 CN, phenyl and phenyl substituted by F, Cl, CH-3 or OCH 3 n is 0 or 1; b R is H or CU 3 W is 0 or S; A is selected from xx Nx y yy AA WO 89/00991 WO 8900991PCT/US88/02459 N x NO y 2 OCH 3 CH2 0 x3 and NC 4 Qz A2 X is selected from HO C 1 to C 4 j alkyl, C, to C 4 alko~y, C 1 to C 4 haloalkoxy, C 1 to C 4 haloalkyl, C, to C 4 thaloalkylthioO C 1 to C 4 a11kylthio, halogeno C 2 to CS a1)koxyalkyl, C 2 to CS 5 a1koxyalkoxy, amnino, C 1 to C 3 alkylandnot di(Cl to C 3 alkyl)amino or C 3 to C 5 cycloalkyl; WO 89/00991 PCT/US88/02459 305 Y is se ncted from C 1 to C 4 alkyl, C 1 to C 4 alkoxy, C 1 to C 4 haloalkoxy, C 1 to C 4 haloalkylthio, C 1 to C 4 alkylth..o, C 2 to C alkoxyalkyl, C 2 to C 5 alkoxyalkoxy, aminio, C 1 to C3 alkylamino, di(Cl to C 3 alkyl~amino, C3 to C 4 alkenyloxy, C 3 to C 4 alkynyloxy,, C 2 to alkylthioalkyl, C 1 to C 4 haloalkyl, C 2 to C 4 allkynyl, azido, cyano, C 2 to C alkylhu1'Lnylalkyl, C 2 to C a3I~ylsulifonylalkyl, CH0H Ca' 'L R L c c VC3 CH O, Cap-C (UH 2m, C R a2 c R a2 L2 and N(OCH 3 )CH 3 rn is 2 or 3; L, and L2 are independently 0 or S; Ra is H or C 1 to C 3 alkyl; Rb and R. are independently C 1 to C 3 alkyl; MorN Zis C or N; Yj'. 0 or CH 2 X, is CH 3 0CH 3 0C 2 H 5 or OCF 2 H; X 2 is CH- 3 CAM Or CH- 2 CF 3 Y2 is 0CH 3 0 2 5 SCSCM H or CH, 2 CH 3 X 3 is CH- 3 or 0CM 3 Y 3 is H- or CH 3 X4is CH- 3 0CH 3 0C 2 H 5 CH 2 0(CH 3 or CI,; and Y 4 is CM 3 0CM 3 0C 2 H 5 or Cl; provided that WO 89/00991 PC-TUS88/0)2459 306 i) when X is Cl, F, Br or I, then Z is CH and Y is OCH 3 0C 2 H 5 N(OCH 3 )CH 3 NHCH 3 N(CH 3 2 or OCF 2 H; ii) when X or Y is C 1 haloalkoxy, then Z is CH; iii) X 4 and Y4 are not simultaneously Cl; Z.v) when W is S, then R is H, A is A-i and Y is CH 3 OCH 3 0C 2 H 5 CH 2 OCH 3 C 2 H 5 CF 3 SCH 3 OCH 2 CH=CH 2 OCH 2 CE-CH, OCH 2 C1F 2 OCH 3 CH(OCH 3 or l,3-dioxolan-2-yl; v) when the total number of carbons of X and Y is greater than four, the number of carbon atoms of Q Ior Q is less than or equal to four; vi) when J is J-6, J-7, J-8 or J-9, and A is A-7, then Z, is CH; and vii) when J is J-6, J-7, J-8 or J-9, and A ills A-i, and X and Y are haloalkoxy or haloalkylthio, then T 2 is F, Cl, Br, CN, SCN, N 3 C 1 to C 2 alkoxy, C 1 to C 2 thioalkyl, NH(Cj tu C 2 alkyl), N(C 1 to C 2 alkyl) 2 N(OCH 3 )CH 3 or N(CH 2 3 or 4- 21 A compound according to Claim 1 wherein: E a single bond; and K~ is 0.

3. A compound according to Claim I wherein: E is, CH 2 or J is J-6; and W is 0. 307

4. A compound according to Claim 2 wherein: R' is selected from H, F, Cl, Br, CH CN, CH 3 OCH 3 SCH 3 or OCF 2 H; R 2 is selected from H, F, Cl, Br or CH3; R 3 is selected from H, C 1 to C 3 alkyl, phenyl, CH 2 CF 3 and CH 2 CFH=CH 2 X is selected from C 1 to C7. alkyl, C 1 to C 2 alkoxy, Cl, F, 'Br, 1, OCF 2 H, CH- 2 F, CF 3 OCH 2 CFI 2 F, OCH 2 CHF 2 OCH 2 CF 3 CH 2 Cl' cyClopropyL and CH 2 Br; Y is selected from H, CI to C 2 alkyl, C 1 I to C 2 alkoxy, CH 2 OCH 3 CH 2 OCH 2 CH 3 NHCU, NOHCH, (C 3 2 CF 3 SCH 3 OCH CH-.CH 2 OCH -CH, OCH CH OCH 3 9 0 S.. C L or H 3 C3 n n caeCt 2akl is 0 99seece fro CFH, OCI3r. SCH CF 1 ylpolorOF .9and Y is selected from CH, OC 3 ,,CH 2 0CH 3 tNlprplo CH n CH(OCH 3 2 WO 89/00991 PCI <US88/02459 308

6. A compound according to Claim 5 wherein: R is H; T 1 is selected from CN, Cl and C 1 to C 2 alkoxy; and T 2 is selected from cyclopropyl, Cl, alkoxy. A compound according J-5 and J-7 to J-13. H, C 1 to C 3 alkyl, CN and C 1 to C 2 to Claim 6 wherein 7. J is J-1 to A compound according to Claim 7 wherein J is J-1.

9. A compound according to Claim 7 wherein J is J-2. A compound according to Claim 7 wherein J is J-3.

11. A compound according to Claim 7 wherein J is J-4.

12. A compound according to Claim 7 wherein J is

13. is J-7. A compound according to Claim 7 wherein J i. -a- WO 89/00991 PCT/US88/02459 309

14. A compound according to Claim 7 wherein J is J-8. A compound according to Claim 7 wherein J is J-9.

16. is J-l0.

17. is J-11. A compound according to Claim 7 wherein J A compound according to Claim 7 wherein J 18, is J-12,

19. is J-13. A compound according to Claim 7 wherein J A compound according to Claim 7 wherein J A compound according to Claim 8: 2-lit li(4-chloro-6-methoxy-2--pyrimidinyl) amino Ic arbonyl Iamino I sulfonyl] -N-methoxy- benzenecarboximidoyl chloride#

21. A compound accordi~ng to Claim 8: (cyano) (methoxyimi no) met hyl rnethoxy-6 -met hyl-2-pyrimidinyl) amino I- carbonyllbenzenesulfonamide.

22. A compound according to Claim 8: N-Methoxy-2- lili(4-methoxy-6-methyl-., 3, triazin-2-yl) aminojcarbonyl] amino] sulfonyllbenzenecarboxciridoyl chloride, WO 89/00991 PCT/US88/02459 310

23. A he;bicidal composition comprising a compound according to any one of Claims 1 to 22 and an agriculturally suitable carrier therefor.

24. A herbicidal composition comprising a compound according to Claim 1, an agriculturally suitable carrier therefor and a compatible pesticide.

25. A method for controlling weeds comprising applying to the locus of the weed, preemergence or postemergence, a herbicidally effective amount of a compound according to one of Claims 1 to 22. INTERNATIONAL SEARCH REPORT International Application No PCT/US 88/02459 1. CLASSIFICATION OF SUBJECT MATTER (it several clasaiticxtlon symbols apply, Indicate all) According to International Patent Classification (IPC) or to both National Classification and IPC PC4 C 07 D 239/46; 239/52; 239/42; 251/16; 251/46; 251/52; 401/12; 409/12; 403/12; A 01 N 47/36 II. FIELDS SEARCHED Minimum Documentation Searc 'ed Classification System IClassitication Symbols IPC 4C 07 D 239/00; C 07 D 251/00; C 07 D 401/00; C 07 D 403/00 C 07 D 409/00 Documentation Searched other than Minimum Documentation to the Extent that such Documents are Included In the Fields Searched Ill, DOCUMENTS CONSIDERED TO KE RELEVANT'I Catat"ory Citation of Document, 11 with Indication, where appropriate, of the relevant passagesi 12 Relevant to Claim No, 13 X EP, A, 0205348 DU PONT DE NEMOURS 1,23 AND COMPANY) 17 rDecember 1986 see page 50, line 32; page 78, lines

71-77, claims A EP, A, 0164269 DU PONT DE NEMOURS 1,23 AND COMPANY) 11 December 1985 see claims A EP, A, 0164017 (BAYER AG) 11 December 1985~ 1,23 see claims A EP, A, 0159576 (BAYER AG) 30 October 1985 1,23 see claims Special categories of cited documesnts, 10 later document published after the international fling date document defining the gereorai state of the which Is not or priority date and not In conflict with the application but cosdrdt eof particulgr relevance cited to understand the principle or theory underlying the consiered o beInvention earier document Wu piublished on or tftisr the International IX" document of particular relevance;, the claimed inventiorn filing date cannot be considered novel or cannot be considered to document which may t'ow doubte on priority claim(s) or Involve on Inventive asp which Is cited to sstabllw) the pUlillcation date of another document of particular relevance*, the claimed Invention citation or othier special rae2on tao specified) cannot be considered to Involve en Inventive stop when the 110" document referring to an oral disclosure, use, exhibition or document is combined with one or more other such docu- other means ments, such combination being obvious to a person skilled document published prior to the International filing date but In the art. later than the priority date claimed document member of the same patent family IV, 'Dals of the Actual Completion of the International Search Date of Mailing of thes Internefional Seorof Report 19th October 1988 17. 11. 88 International Searching Authority sga to flo EU~ROPEAN PATENT OFFICE FR 9111FN Form PCT/ISA1210 (second sheet) IjorluAry ANNEX TO THE INTE RPNATIONAL SEARCH REPORT ON INTERNATIONAL PATENT APPLICATION NO. US 8802459 SA 23559 This annex lists the patent family members relating to the prent documents cited in the above-mentioned international search report. The members are as contained in the European Patent Office EDP ile on 0.4/i11/88 The European Patent office is in no way liable for these particulars which are merely given for the purpose or information. Patent document Publication Patent family blctn cited in search report date memnber(s) dt EP-A- 0205348 17-12-86 AU-A- 5859986 18-12-86 JP-A- 620164,57 24-01-87 US-A- 4678498 07-07-87 CA-A- 1236459 10-05-88 EP-A- 0164269 11-12-85 US-A- 4744816 17-05-88 EP-A- 0164017 11-12-85 OE-A- 3420769 05-12--85 JP-A- 61040273 26-02-86 US-A- 4638004 20-01-87 EP-A- 0159576 30-10-85 DE-A- 3413490 17-10-85 JP-A- 60228464 13-11-85 CA-A- 1217188 27-01-87 US-A- 4659366 21-04-87 a. C a. 0 For more details about this annex see OfTiclal Journal of the European Patent Ollice, No. 12/8Z